0:00:04 “Gentlemen, you have undertaken to cheat me.
0:00:07 I won’t sue for the laws too slow.
0:00:08 I’ll ruin you.”
0:00:11 Yours truly, Cornelius Vanderbilt.
0:00:14 And that quote is the embodiment of the man
0:00:17 we’re gonna talk about today, Cornelius Vanderbilt.
0:00:33 – Welcome to The Knowledge Project.
0:00:35 I’m your host, Shane Parrish.
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0:00:54 hand-edited transcripts, and so much more.
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0:01:05 – He began as a teenage ferry captain,
0:01:08 battling storms in New York Harbor for pennies.
0:01:11 From these humble beginnings, he clawed his way
0:01:15 to become America’s most feared and admired magnet.
0:01:18 Cornelius Vanderbilt didn’t just dominate one industry,
0:01:22 he conquered three: ferries, steamships, and railroads.
0:01:27 Rivals called him ruthless, passengers called him unstoppable.
0:01:29 But Vanderbilt didn’t just build businesses,
0:01:32 he rewrote the rules, laying the foundation
0:01:34 for the modern corporation.
0:01:36 This is his story.
0:01:38 If you think today’s tycoons are tough,
0:01:40 wait till you meet the Commodore.
0:01:43 Most of the research for this episode
0:01:46 came from reading “The First Tycoon” by TJ Stiles,
0:01:50 and “Tycoon’s War” by Stefan Dando Collins.
0:01:51 Remember to stick around at the end of the show
0:01:54 for my reflections and afterthoughts,
0:01:57 as well as the lessons you can learn from Vanderbilt.
0:02:01 If you want to read my highlights from “Tycoon’s War” or “The First Tycoon”,
0:02:05 you can sign up below fs.blog/membership.
0:02:09 Just look in the description for this podcast, you can find a link.
0:02:11 It’s time to listen and learn.
0:02:15 This podcast is for entertainment and informational purposes only.
0:02:23 It’s January 4th, 1877.
0:02:25 A winter wind cuts through New York City,
0:02:28 where a crowd gathers outside the Church of Strangers.
0:02:33 Inside, elites await the reading of Cornelius Vanderbilt’s will,
0:02:37 rumored to be worth $100 million.
0:02:40 One twentieth of all U.S. currency.
0:02:44 His legendary willpower and ruthless business tactics
0:02:47 had forced rivals to pay him to go away.
0:02:51 Now, the entire city wants to see how the man who once dominated ferries,
0:02:55 steamboats, and railroads chose to dispense his vast fortune.
0:03:00 His early life was filled with fistfights, high-speed steamboat duels,
0:03:04 engine explosions, and numerous near-death experiences.
0:03:09 His latter days with daredevil harness races and high-stakes financial confrontations
0:03:11 that even extended to the international scene.
0:03:17 By the time of his death, virtually every American had paid tribute to his treasury.
0:03:21 They had passed through his Grand Central Depot on 42nd Street,
0:03:25 crossed the bridges over the sunken tracks along 4th Avenue,
0:03:29 or traveled one of the countless ferries, steamboats, or railroads
0:03:31 he had controlled during his 60-year career.
0:03:35 Vanderbilt was the precursor to a class of men
0:03:38 who would wield power within the state so great
0:03:40 that it would rival the state itself.
0:03:45 Rockefeller, Carnegie, Mellon, Gould, Morgan,
0:03:49 all were just beginning their careers when Vanderbilt stood at his zenith.
0:03:52 They studied him and they followed his example,
0:03:55 though few would match his impact.
0:03:58 His admirers called him the finest example of the common man
0:04:00 rising through hard work and ability.
0:04:02 His critics, on the other hand, called him ruthless,
0:04:07 an unelected king who never pretended to rule for his people.
0:04:11 But Vanderbilt’s significance was more complex, more contradictory,
0:04:14 than either of his admirers or critics fully grasped.
0:04:20 His life spanned from the days of George Washington to those of John D. Rockefeller,
0:04:26 from a rural, agricultural, essentially colonial society in which the term businessman was unknown
0:04:31 to a corporate, industrial economy that would define America’s future.
0:04:39 Vanderbilt didn’t just experience that changing time period and watch as the American economy rose around him.
0:04:43 He was possibly the largest force at the time responsible for the building of it.
0:04:49 He was the trailblazer in the corporate world and reimagined what a corporation could do.
0:04:54 Now, to truly understand the Commodore and that world, we must go back to the beginning,
0:05:04 to Stanton Island, May 27th, 1794, when Phoebe Vanderbilt gave birth to her fourth child naming him Cornelius after his father,
0:05:07 Although they called the boy Cornelius.
0:05:20 The Vanderbilt’s descended from Jean Arsene Vanderbilt, who had come to the New World to farm generations earlier.
0:05:25 On Stanton Island, most of the original Dutch settlers led an inward-looking rural life.
0:05:30 Americans of British descent often viewed them with distaste.
0:05:39 As one traveler observed in the 1790s, nothing can exceed the state of indolence and ignorance in which these Dutchmen are described to live.
0:05:44 Many of them are supposed to live and die without having been five miles from their own houses.
0:05:51 But there was one distinctive feature of the rural Dutch that would profoundly shape young Cornelius Vanderbilt:
0:05:53 they farmed for profit.
0:05:58 While many English-speaking farmers in the region devoted much of their efforts to subsidence,
0:06:04 Dutch farming was market-oriented and derived its distinct characteristics from Dutch tradition.
0:06:09 The rural Dutch shared the commercial consciousness of their urban brethren.
0:06:14 They clattered their wagons into Albany, New Brunswick, and New York to sell their produce
0:06:16 with a savvy that became their custom.
0:06:21 When a cobbler refused to return a man’s shoes until he made full payment,
0:06:25 the frustrated customer wrote in his diary, “He is too Dutch by half.”
0:06:29 Young Cornelius was born into this tradition of commerce.
0:06:34 His parents created a household where, far earlier than in remote communities,
0:06:37 the marketplace strode right through the door every day.
0:06:43 While farmers living up the Hudson may make just one delivery of crops to riverside merchants,
0:06:49 in an entire year at harvest time, the Vanderbilt house pulsed constantly with buying and selling,
0:06:52 borrowing and lending, earnings and debt.
0:07:00 Cornelius’ father had built or bought a prerogar, a specialized two-masted vessel deployed by the
0:07:06 dutch for trading and began ferrying neighbors and their produce along the bay in Manhattan.
0:07:10 Phoebe, Cornelius’ mother, was equally entrepreneurial.
0:07:16 She was not only the family oracle one 19th century writer declared, she was the oracle of the neighborhood
0:07:20 whose advice was sought in all sorts of dilemmas and whose judgment had weight.
0:07:27 Court records show she lent money at commercial rates of interest and once even foreclosed on a
0:07:34 widow’s mortgage. The widow being her own daughter. Unlike most farmers, they actually lived within
0:07:40 sight of New York City, where from their Stanton Island home, they could literally see the mass of
0:07:43 ships in the harbor bringing goods and ideas from around the world.
0:07:50 The United States that Cornelius was born into was a very young nation.
0:07:56 Keep in mind that when Vanderbilt was born, George Washington was still early in his second term of the
0:08:03 presidency. Only five cities held more than 10,000 residents at this time and the percentage of the
0:08:09 the nation’s four million citizens who lived in towns of at least 2,500 people languished in the
0:08:15 single digits and would linger there for decades to come. Most Americans live scattered along the
0:08:19 Atlantic coast with only the bravest pioneers venturing west to the Appalachians.
0:08:26 By his early teens, Vanderbilt was totally drawn to the water, leaving the fields behind.
0:08:33 Accounts on this vary, but by the age of 16, he was running his own ferry that was either owned by
0:08:38 his parents or one that he purchased with a loan from them, promising to help pay the family’s $1,000
0:08:45 mortgage. His plan to do so? Operate the boat as a ferry between Stanton Island and the growing
0:08:52 Manhattan. The teenager launched himself into this venture with intensity, charging a shilling each
0:08:58 way, 12 and a half cents that accumulated with glacial slowness in a vessel that seated just 20
0:09:04 passengers. Vanderbilt discovered in those daily handfuls of silver, a hunger for money that would
0:09:11 shape his life from then on. What distinguished his small ferry service from the competition was
0:09:17 predictability. While other boatmen waited until their crafts filled to their capacity, the teenage
0:09:24 entrepreneur introduced something uncommon to the New York Harbor, a schedule. His ferry departed at fixed
0:09:29 times regardless of the passenger count, a self-imposed discipline that transformed water
0:09:36 transit from casual to reliable service, earning him loyalty and repeat business. This was an extension
0:09:41 of how he lived his life, with one contemporary at the time saying his life was regulated by self-imposed
0:09:50 rules, with a fixedness of purpose as invariable as the sun in its circuit. That reliability for service
0:09:56 extended to the winter months as well. When ice choked the harbor, he was often the only ferryman willing to
0:10:02 make the crossing. He studied the tides, winds and currents relentlessly and mastered the natural forces
0:10:10 that other boatmen merely accommodated. In simple terms, he worked harder. During the blinding storms,
0:10:15 when sleet and snow crashed across the bay, Pearl Street merchants would seek out the gangly team,
0:10:21 trusting him alone to deliver urgent messages to vessels anchored in the harbor, earning Vanderbilt
0:10:28 additional income. Not only was he reliable, in these months he was often the only option for
0:10:32 passengers. And although there was no recorded earnings from this time, presumably he could charge
0:10:39 a premium for his services. In fair weather, it was a different story and he competed aggressively on
0:10:44 price, undercutting established operators as a rule. If other ferrymen charged 18 cents,
0:10:50 Vanderbilt would charge 12. If they dropped to 10, he’d go to 8. This approach, price competition to
0:10:55 the point of driving out rivals, would become his signature strategy throughout his career, regardless
0:11:02 of scale or industry. It’s worth pausing here for a second to talk about this. Isidore Sharp,
0:11:08 the founder of the Four Seasons, said something that has long struck with me. He said, “Excellence is the
0:11:15 capacity to take pain.” One of the things that sets Vanderbilt and other outliers apart is their
0:11:22 willingness to tolerate pain. Most people have no capacity to endure pain, financial or psychological.
0:11:28 And if you can, you can gain a real advantage. It hurt Vanderbilt to cut prices, but it hurt his
0:11:33 competitors more and he knew it. It hurt Vanderbilt to run his service when he couldn’t see or the
0:11:40 weather was bad, but he knew it hurt his competitors so much they wouldn’t even operate. It’s hard
0:11:45 to compete with someone who can tolerate more pain than you. There’s over 500,000 small businesses in
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0:11:58 That’s why BCAA created One Size Doesn’t Fit All Insurance. It’s customizable based on your unique
0:12:03 needs. So whether you manage rental properties or paint pet portraits, you can protect your small
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0:12:17 radio to receive $50 off. Conditions apply. Okay, back to our story. Within a year, legend has it
0:12:22 that teenage Vanderbilt had not only paid off his loan, but had given his parents several hundred
0:12:28 dollars towards their mortgage. And it is here where we see Vanderbilt evolve from just a hard worker
0:12:34 into something much more. If his parents had taught him anything, it was that business thrived on
0:12:39 relationships. Though his hands grew calloused from twisting wooden tillers, the harbour brought him not
0:12:45 just physical strain, but valuable connections. As he accumulated his modest portion of the ferry’s
0:12:53 earnings through 1810, 1811, and 1812, Vanderbilt made a pivotal decision: to purchase shares in other
0:13:01 boats. Shares whose profits he deliberately kept separate from his family obligations. Vanderbilt transformed
0:13:07 himself from a mere labourer, somebody who worked harder than anyone else, into an investor, or to
0:13:12 put it plainly, a capitalist. His money was now making money for him, expanding his reach beyond
0:13:19 what only his two hands could accomplish in a day’s work. As war with Britain loomed and then erupted in
0:13:25 1812, these investments positioned him perfectly to capitalize on the shifting trade patterns. With a
0:13:31 British blockade due to the war forcing coastal shipping to rout through Stanton Island and overland
0:13:36 across New Jersey, Vanderbilt’s position between Manhattan and Stanton Island suddenly became
0:13:43 a commercial choke point and one where he could take advantage. By 1813, with war raging and his
0:13:50 reputation growing, Vanderbilt took two decisive steps towards independence. First, he commissioned his very
0:13:56 own custom-built ferry in New Jersey, funded by his carefully hoarded and growing savings. On Sundays,
0:14:02 he would sail up the Pasek River to inspect the boat’s progress accompanied by his cousin Sophia Johnson,
0:14:08 the woman who would become both his bride and his business partner in his life’s enterprise. The boat
0:14:13 represented his commercial ambitions, while the marriage his declaration of financial independence
0:14:30 and moved into a small house near the ferry dock. This wasn’t merely a personal milestone but a commercial
0:14:37 one, the final step in his evolution from wage-earning boatmen to an entrepreneurial force. By his early 20s,
0:14:43 he had expanded from a single ferry to multiple, including larger schooners used for coastal shipping.
0:14:48 The locals no longer called him Cornille. He was now widely known as Captain Vanderbilt.
0:14:57 The War of 1812 accelerated Vanderbilt’s rise. With military necessity came opportunity. In 1814,
0:15:03 as the United States stood on the brink of defeat with Washington captured and New York bracing for an attack,
0:15:08 one account says that Vanderbilt secured a lucrative military contract to carry supplies to the city’s
0:15:14 defensive fortifications. When asked why he won the bid, despite not offering the lowest price,
0:15:19 the military officer’s response crystallized Vanderbilt’s growing reputation. “Don’t you
0:15:25 know why we have given the contract to you? It’s because we want this business done and we know you’ll do it.”
0:15:31 Following the war’s end in 1815, Vanderbilt made a strategic decision that revealed his commercial
0:15:37 instincts. He moved his young wife from Stanton Island to 93 Broad Street in Manhattan, settling
0:15:44 into an artisan’s boarding house. The relocation placed him deliberately at the center of commerce
0:15:49 and information where newspapers published shipping schedules and commodity prices, where auctions
0:15:56 and exchanges operated daily and were reputations, the true currency of business in that era, were established
0:16:03 or broken. At his new home in Manhattan, Vanderbilt studied the city’s other merchants carefully. He noted that
0:16:08 despite the energy and innovations of artisans and small businessmen, New York’s wealthiest citizens were
0:16:16 primarily general merchants who traded in international cargoes of all types. When the government needed to sell war bonds,
0:16:22 it turned to merchant financers like John Astor. Vanderbilt internalized this lesson realizing that
0:16:29 the wealth he desired would require him to trade in cargoes and not just provide its transportation. He
0:16:35 would have to expand. With the war over, New York erupted in commercial activity and Vanderbilt jumped in
0:16:42 with both feet. His approach showed both boldness and shrewdness. Rather than remaining in the familiar
0:16:48 harbor waters, the now 20-year-old entrepreneur reached out to distant ports along the Atlantic coast.
0:16:53 More importantly, he began seeking partners with greater expertise and capital than he had.
0:16:59 He joined forces with his brother-in-law, John DeForest, an experienced mariner who commanded the schooner
0:17:04 Charlotte. Vanderbilt purchased a share in this vessel using it to transport goods between New York
0:17:10 and the Southern ports before eventually buying full ownership. Vanderbilt also partnered with
0:17:16 his father and others to finance even larger ferries suitable for open water. These vessels cost approximately
0:17:24 $750 each. With a small but growing fleet, Vanderbilt aggressively began seeking out market opportunities.
0:17:29 He raced competitors to Virginia’s oyster grounds, sailed up the Delaware River to purchase shad,
0:17:36 and ventured up to New Jersey’s Raritan River, hiring horsemen to spread word of his available fish.
0:17:42 His commercial operations extended to paying boatmen to meet incoming ships while he negotiated cargo sales
0:17:47 on South Street. His business practices here displayed the same forceful determination that
0:17:54 characterized his ferry operations. Court records from 1816 and 17 showed that Vanderbilt pursued debts through
0:18:00 legal channels, though judges frequently determined he had overstated what was owed. This commercial
0:18:07 aggressiveness served him in America’s rapidly changing economy. The post-war era brought dramatic
0:18:13 transformations to American commerce. Manufacturing, which had developed during wartime isolation, continued
0:18:19 expanding. Banking proliferated, especially in New York, and the number of American banks increased from
0:18:29 208 to 246 in 1815 alone, while currency in circulation jumped from 46 to 68 million. Vanderbilt’s rise
0:18:35 paralleled these developments completely as he sought opportunities in the growing domestic markets.
0:18:41 Transportation barriers remained a critical limitation in commerce in early America. In the
0:18:46 era before railroads, moving goods 30 miles on land could cost as much as shipping them across the
0:18:52 entire Atlantic Ocean. Even coast-wise shipping in small schooners had limited capacity. Meanwhile,
0:18:58 up-river journeys against currents could take days or prove impossible, and cargoes would often be lost or
0:19:04 damaged. The speed of transportation also limited the speed of information and thereby constrained long-distance
0:19:11 commerce and financial markets. America needed a transportation revolution, and it was coming.
0:19:17 In 1817, New York State began constructing the Erie Canal, which would connect the Great Lakes to the
0:19:23 Atlantic Ocean, while steamboats at the same time appeared on the Hudson River, offering transportation
0:19:31 independent of wind, muscle, or current. By December 1817, the 23-year-old Vanderbilt had substantial assets
0:19:36 now under his command. He was following the path of other successful merchants he had observed. He was a
0:19:42 maritime merchant rising through the ranks of America’s most vibrant port city, and specializing in cargo
0:19:47 trading. And he might well have made a fine living as just another successful merchant in
0:19:57 Manhattan if it were not for a chance encounter on November 24th, 1817.
0:20:05 On that November day, Vanderbilt turned at the sound of his name and saw a well-dressed 60-year-old
0:20:12 man looking at him with sharp, hard eyes. The man introduced himself as Thomas Gibbons, a staggeringly
0:20:18 rich rice planter from the state of Georgia, now residing in Elizabethtown, New Jersey. Empathetic and
0:20:23 direct, Gibbons explained that the captain of his steamboat had suddenly left my employ, creating what he
0:20:29 called my present embarrassment. He needed someone to take charge of the boat on this day, and I expect
0:20:35 for a few days to come. Would Vanderbilt do it? The vessel in question was named Stowdinger, nicknamed
0:20:41 the Mouse of the Mountain, or simply Mouse, as it was second-hand and a small craft, smaller at 47 feet
0:20:47 than even Vanderbilt’s own small boats. But there was one crucial difference between the mouse and Vanderbilt’s
0:20:55 own boats. It ran on steam. Vanderbilt understood that the steam engine was the most dramatic
0:21:01 technological breakthrough since the printing press. To move on water at will against the wind or current
0:21:07 was to transform a fundamental fact of life at this time. A practical education in the steamboat
0:21:13 business would be worth more than a few days of taking orders from someone else. The engagement with
0:21:17 Gibbons seemed to set him back a step in his own plans, which surprised his friends and acquaintances.
0:21:24 Vanderbilt aspired to be more and more, and he was using his own boats to embark on the only obvious
0:21:30 voyage to wealth that he could see, setting up as a general merchant. As he stepped aboard the mouse
0:21:35 and inspected its copper boiler, he kept his own boats plying between Stanton Island and Manhattan with
0:21:41 passengers and produce while his schooners nosed along coastal waters with cargoes of fish and woolens,
0:21:47 but it’s clear that he saw the advantages of this new connection. What he did not reckon on was how
0:21:52 well he would get on with Gibbons. “I always thought Thomas Gibbons a very strong-minded man,
0:21:58 the strongest I ever knew,” Vanderbilt said later. “I don’t believe any human could control him. He was
0:22:03 the man that could not be led. He could just as easily have been describing himself when he said that.”
0:22:08 There’s another reason that Vanderbilt may have chosen to run a steamboat for a few days,
0:22:13 and that was because of the excitement. Running a steamboat at the time would make him the focus of a
0:22:21 very interesting legal and business war that was the talk of the waterfront. In 1798, Chancellor Robert
0:22:27 Livingston, who was a powerful New York aristocrat, convinced his friends in the legislature to give him
0:22:34 a monopoly on steamboat ships in the New York state waters. In 1807, after partnering with inventor Robert
0:22:40 Fulton, they launched the first commercially successful steamboat service on the Hudson River. Not only did they
0:22:45 have a monopoly, the New York legislature went so far as to give them the right to seize steamboats that
0:22:52 entered the New York waters from other states. Enter Thomas Gibbons, the man who would hire Vanderbilt.
0:22:59 Cunning and commanding, Gibbons’ daughter dryly noted he had a peculiar and singular mode of doing business.
0:23:08 Gibbons was, in a word, intense. Perhaps an example will help illustrate this point. Once he became embroiled in a
0:23:14 dispute with his neighbor, a man named Aaron Ogden, what began as a fight over a leased peer escalated
0:23:20 when Ogden involved himself in Gibbons’ ongoing family disputes. Their conflict reached a breaking
0:23:28 point when Ogden had Gibbons arrested for an unpaid debt. For Gibbons, this had become an affair of honor,
0:23:35 and on July 25th, 1816, he stormed over to Ogden’s house, horsewhip in hand. He pounded on the door as
0:23:41 Ogden ran out the back and scrambled over a fence. Gibbons tacked up a challenge that read, “Sir, I
0:23:46 understand that you have interfered in a dispute between Miss Gibbons and myself. My friend General
0:23:52 Dayton will arrange with you the time and place of our meeting.” He later testified in court that if he had
0:23:56 found him at home he meant to have whipped him, within an inch of his life, in his own house,
0:24:02 for he knew he was a coward. Ogden, who had no intention of exchanging shots at Don,
0:24:08 had Gibbons arrested for trespass and for dueling. Gibbons decided to get revenge another way. He would
0:24:15 drive Ogden out of the steamboat business. There was just one problem. Ogden had become an ally of the
0:24:21 Livingston Fulton monopoly, receiving a license to operate his steamboat services between New Jersey
0:24:28 and New York. Taking on Ogden meant taking on the most powerful monopoly in New York State. When Gibbons
0:24:33 launched his steamboat service in defiance of that monopoly, he needed a ship captain who wouldn’t back
0:24:40 down under pressure. He needed someone with technical skill, physical courage, and a defiant nature. And he
0:24:45 found that man in Cornelius Vanderbilt. The Vanderbilt who stepped aboard the mouse
0:24:50 that November day was walking into a fight bigger than himself, which is saying something because he
0:24:57 was a very big man. The Livingston Fulton monopoly represented the old economic order. It was a system
0:25:04 where political power and economic privilege were inextricably linked. What began as a temporary job
0:25:09 for a few days quickly became a permanent position as Gibbons recognized Vanderbilt’s exceptional
0:25:14 abilities. Vanderbilt quickly mastered the technical aspects of steam, but more importantly,
0:25:20 he shared Gibbons’ combative nature and willingness to challenge authority. Indeed,
0:25:25 the authority that he was challenging was the remnants of what might have been the last aristocratic
0:25:31 generation in America, one that felt it in their inherited privilege to give themselves state-granted
0:25:37 monopolies as they saw fit. The monopoly holders did not take this challenge from Gibbons and his
0:25:43 steamboat captain lightly. They used every legal maneuver at their disposal to shut down the
0:25:48 operation. They had Vanderbilt arrested repeatedly, they tried to seize the mouse, and they even attempted
0:25:54 to bribe him to abandon Gibbons. But Vanderbilt remained loyal to Gibbons, partly because of their
0:25:59 shared temperament, but also because he recognized the larger principle that was at stake. The monopoly
0:26:05 wasn’t just unfair to competitors and customers, it was slowing the very adoption of steam technology
0:26:11 that could revolutionize transportation for everyone. Vanderbilt had grown up in a market-oriented
0:26:17 world and represented the new individualistic American citizen, one that was not guided by honor and
0:26:24 respecting others’ rights to a legal monopoly. When Ogden’s men physically blocked Vanderbilt from docking in
0:26:29 New York, he responded in kind, and as Gibbons’ case against the monopoly wound its way through the
0:26:35 courts, Vanderbilt took charge of the fight on the water. He developed a reputation for daring and
0:26:40 ingenuity. When monopoly agents came to arrest him, he would sometimes hide in the ship’s engine room, other
0:26:46 times he would simply outrun them, pushing the steamboat’s engines to their limits and relishing the fight.
0:26:52 The legal battle culminated in a landmark Supreme Court case called Gibbons versus Ogden.
0:26:57 And remember, this just started as a neighborly dispute, and now we’re in the Supreme Court.
0:27:03 In 1824, Chief Justice John Marshall ruled in Gibbons’ favor, striking down the New York steamboat
0:27:09 monopoly. The decision established that the federal Congress alone had the power to regulate interstate
0:27:14 commerce. This ruling affirmed that the federal government has the authority to regulate interstate
0:27:20 commerce and put a limit on state authority. The steamboat monopoly was dead. Vanderbilt and Gibbons
0:27:26 had won. The victory, however, came with a tragic footnote. Gibbons, Vanderbilt’s cantankerous mentor,
0:27:31 died shortly after the ruling, leaving Vanderbilt at a crossroads. Would he remain to manage
0:27:35 Gibbons’ steamboat line for his heirs, or would he strike out on his own?
0:27:42 After working for Gibbons’ son and heir William for a few years, Vanderbilt decided his apprenticeship was
0:27:48 over in 1829. He had mastered steam navigation, knew the business inside and out, and earned a
0:27:53 reputation as one of the country’s top steamboat operators. But it was time to become his own
0:27:59 master again. Launching his first independent steamboat venture on the busy New York-Philadelphia route,
0:28:04 he went head-to-head with his former employers. He named his vessel, fittingly, the Independents.
0:28:10 Vanderbilt’s business model was straightforward, echoing his teenage fairy days: better service,
0:28:15 lower prices. He cut fares dramatically from three dollars to just one dollar, forcing rivals to
0:28:21 match or lose customers. By upgrading food and accommodations and running on razor-thin margins
0:28:27 others couldn’t sustain, Vanderbilt gained an upper hand. He practically lived aboard his boats,
0:28:34 rarely seeing his wife and family fully committed to his ambitious vision. Critics accused him of ruinous
0:28:40 competition and cutthroat capitalism. The New York Times later described Vanderbilt accusing him of
0:28:46 pursuing competition for competition’s sake. During this era, many companies still operated under the
0:28:53 unspoken code of respecting each other’s territory. But Vanderbilt ignored this tradition entirely. Passengers
0:28:59 eagerly flocked to his boats, attracted by his unbeatable fares and dependable service. Competitors,
0:29:04 however, struggled to grasp his simple but revolutionary insight: increased volume could
0:29:10 more than offset slim or even negative profit margins. By drastically reducing prices, Vanderbilt
0:29:16 significantly boosted demand, a phenomenon economists now recognize as Jevons paradox, where improved
0:29:22 efficiency and reduced costs lead to greater overall consumption. And we’re going to get into this a
0:29:27 little later, but here’s a little foreshadowing for you. He would often get paid not to compete. So when
0:29:32 I say he’s operating at negative profit margins, it sounds like, well, that doesn’t work. But in effect,
0:29:38 what would happen is he does get paid not to compete. So it does work. Travel time between New York and
0:29:44 Philadelphia shrank dramatically to just 10 hours, driven by Vanderbilt’s obsession with speed. This
0:29:51 didn’t merely make the trip affordable, it made it exciting. What began as basic transportation soon
0:29:57 transformed into theatrical spectacle. The waters of Raritan Bay became an arena. It’s steamboats,
0:30:03 the gladiators, and the passengers saw themselves not just as travelers, but as active participants in a
0:30:09 thrilling competition that embodied the spirit of the age. They didn’t merely seek passage,
0:30:15 they craved victory and Vanderbilt was determined to deliver. Vanderbilt’s ship, the thistle, sliced
0:30:20 through the waters aggressively, mirroring its captain’s relentless spirit. To Vanderbilt this
0:30:27 battle wasn’t solely about profit or winning, it was about domination. This competitive drive defined
0:30:32 Vanderbilt’s character. Historical author Stephen Dando Collins notes that Vanderbilt was driven by two
0:30:39 things, making money and winning. He had an instatiable thirst for conquest, often temporarily
0:30:45 sacrificing profit to achieve victory. Once he triumphed though, Vanderbilt rarely lingered. Instead,
0:30:51 he swiftly sought out his next challenge. A more modern parallel to Vanderbilt’s relentless competitiveness
0:30:57 can be seen in athletes like Michael Jordan, who famously manufactured slights to fuel his competitive
0:31:02 edge. For many, including Vanderbilt, the impossible challenge wasn’t a bug,
0:31:07 it was the feature. Victory itself was less fulfilling than the next mountain to climb,
0:31:13 the next unwinnable fight. The Evening Post observed how the sport arising from boat racing
0:31:18 had captured public imagination. The New York-Philadelphia route attracted passionate fans who
0:31:24 cheered their champions. English actress Anne Royal described her boats as “our heroine” recounting
0:31:29 dramatically how the rival vessel drew up alongside somewhat boldly and sometimes had the presumption
0:31:35 to run ahead. Her account read less like a travel diary and more like a sports reporter’s play by
0:31:42 play. The races compressed time and space, combining speed, affordability, and spectacle to create new
0:31:49 markets. Vanderbilt applied what economists later termed price elasticity of demand, demonstrating that
0:31:56 transportation wasn’t a fixed need but one stimulated by accessibility and excitement. As fares dropped,
0:32:01 more people traveled reshaping commerce by enabling merchants to access distant markets rapidly and
0:32:08 allowing stock market speculators to profit from faster information flow. Leisure travel expanded, forcing
0:32:15 aristocrats to mingle with those who were considered social inferiors at the time. Vanderbilt’s competitive
0:32:21 success earned him the nickname Commodore, a title usually reserved for naval commanders. The irony wasn’t lost on
0:32:27 Vanderbilt who had begun his career challenging monopolies. Now he commanded a fleet himself.
0:32:33 Despite his ruthlessness in business, he lived pretty frugally with tremendous self-control and personal
0:32:40 expenditure, but none when pursuing competition and business expansion. The confrontation began
0:32:47 dramatically when three angry representatives from the Hudson River Steamboat Association stormed Vanderbilt’s office.
0:32:53 They accused him of secretly owning the Westchester, a steamboat running the Albany line at a scandalously
0:33:00 low fare of $2, undercutting the established $3 price. This powerful association was an alliance between
0:33:05 the Hudson River, North River, and Troy steamboat companies, and it had previously paid rival Robert
0:33:14 Stevens $80,000 to withdraw from competition for 10 years to secure their monopoly. Vanderbilt recognized this
0:33:19 this was a dangerous moment. He truthfully insisted that he no longer had ties to the Westchester,
0:33:25 and it even declined profitable offers to avoid involvement in any rivalry, but the monopoly leaders
0:33:33 didn’t believe him. War was inevitable. The ensuing Hudson River rate war exposed a striking contradiction
0:33:39 with Vanderbilt. When the monopoly retaliated by targeting one of his own profitable roots, Vanderbilt exploded with
0:33:47 fury. In a dramatic public declaration in the New York Evening Post. He positioned his people’s line as a
0:33:53 champion against the great triangular monopoly, appealing directly to public support. What Vanderbilt
0:34:01 conveniently omitted was his own history of enforcing monopolies without hesitation. Yet as the underdog,
0:34:06 Vanderbilt captivated public imagination. He deployed his ships with the Nimrod and the champion,
0:34:14 slashing fares at first to $1 and then an astonishingly low $0.50. With relentless intensity,
0:34:21 he expanded service-launching, aggressive advertising campaigns proclaiming “no monopoly” and winning public
0:34:27 acclaim at every dock. However, when spring thawed the Hudson River after winter, passengers found fares
0:34:34 back at $3 and Vanderbilt’s ships gone. Years later, a New York Herald investigation revealed he had been
0:34:44 paid off by the original monopoly, $100,000 plus an annual $5,000 fee to withdraw. Vanderbilt’s brutal but
0:34:51 effective strategy became clear: identify lucrative routes, wage devastating fair wars, use anti-monopolistic
0:34:58 rhetoric to rally public support and a bit of showmanship and demand large payoffs to end the
0:35:04 competition. This is something he would repeat over and over again. His focus shifted from steamboats to
0:35:10 the promising railroad, a safer and faster connection between New York and Boston, bypassing the notoriously
0:35:17 rough seas at Point Judith. Vanderbilt recognized the railroad’s potential immediately, later remarking
0:35:22 to its chief engineer, “There’s nothing like it. The first time I ever traveled on this Stonington, I made up my mind.”
0:35:36 In 1837, Cornelius Vanderbilt saw an opportunity marking his first significant step into railroads
0:35:43 with the financially troubled Stonington Railroad. Saddled with $2.6 million in debt, Vanderbilt realized
0:35:49 controlling travel along Long Island Sound required balancing both rail and steamboat operations.
0:35:55 At home, Vanderbilt’s relationship with his 16-year-old son William was strained by his demanding nature.
0:36:01 Frustrated by Billy’s passive demeanor, Vanderbilt placed him under Wall Street broker Daniel Drew,
0:36:08 forging an uneasy partnership. Drew accepted Billy as a clerk, but demanded a favor in return:
0:36:13 access to one of Vanderbilt’s new steamboats for his Hudson River operations. While they had once been
0:36:21 rivals, they had, at least for the time, transformed it into an uneasy partnership, each respecting the
0:36:25 other’s ruthlessness while never fully trusting one another. Vanderbilt faced
0:36:32 renewed competition on his Boston-to-Main steamboat route, responding with fierce public anti-monopoly
0:36:38 rhetoric. By now, his reputation alone often intimidated rivals into paying him off, instead
0:36:44 of competing. The transportation company, for instance, purchased Vanderbilt’s Lexington steamer
0:36:53 for $60,000 plus a $10,000 bonus, well above its real value, just to remove it from competition. Vanderbilt
0:37:00 skillfully recouped his investment while shifting his focus to railroads. Unlike steamboats, the Commodore
0:37:07 couldn’t easily compete with railways, so he needed a new strategy. In 1840, when the struggling Stonington
0:37:13 Railroad sought Vanderbilt’s help, he cryptically remarked, “If I owned the road, I’d know how to make
0:37:19 it profitable.” Though initially dismissed, Vanderbilt quietly joined the Long Island Railroad Board,
0:37:25 redirecting business away from the Stonington. Shareholders panicked at the high debt and reduced
0:37:32 traffic. Its stock plummeted, allowing Vanderbilt and his allies, including Drew, to secretly acquire a
0:37:39 controlling share. By 1847, Vanderbilt became president of the Stonington, the first stop toward railroad
0:37:47 dominance. By 1848, Vanderbilt had firmly established his transportation empire, becoming the monopoly he
0:37:53 once opposed. Though his methods contradicted his anti-monopoly rhetoric, Vanderbilt democratized
0:37:57 transportation, forever transforming the industry. And he was only just beginning.
0:38:06 In early 1848, far from Vanderbilt’s bustling New York, two men carried gold nuggets into an adobe
0:38:13 building in California, triggering one of history’s greatest economic frenzies: the California gold rush.
0:38:20 Vanderbilt’s eye was always drawn to major transportation routes. Now, watching tens of
0:38:26 thousands head to San Francisco each month, he saw a bigger opportunity than anything he’d tackled before.
0:38:33 This is why the Commodore went to see Secretary of State John M. Clayton with Joseph L. White,
0:38:38 a former politician who knew his way around Washington. Vanderbilt explained the situation
0:38:43 clearly. Without a transcontinental railroad, only a fraction of the Americans and European
0:38:48 immigrants rushing west could travel by covered wagon. The overland route was dangerous, passing
0:38:53 through hostile Native American territories and treacherous mountain ranges, often taking up to six
0:39:00 months. Hundreds died annually from accidents, exposure, starvation, or attacks. The alternative,
0:39:06 sailing around Cape Horn at the tip of South America was faster. Roughly 90 days, but expensive at around
0:39:14 $600 per passenger in the lowest class. “I can improve on that,” Vanderbilt told Clayton. “I can
0:39:20 make money at $300 by crossing through Nicaragua.” But Vanderbilt wasn’t primarily after passengers,
0:39:27 he wanted the lucrative U.S. mail contracts. Vanderbilt proposed to Clayton exclusive rights from the
0:39:32 Nicaraguan government to build a canal. In the meantime, he planned to operate steamships from New
0:39:38 York to Nicaragua and onward to San Francisco. Passengers would travel up the San Juan River,
0:39:43 cross Lake Nicaragua by steamship, and then journey the remaining 12 miles by mule.
0:39:50 Clayton favored Vanderbilt’s proposal as an American-built canal would exclude British
0:39:56 interests and expand American influence. White successfully secured an initial contract from
0:40:01 Nicaragua, but the company soon faced controversy when Britain protested, asserting control over
0:40:08 strategic points in Nicaragua. Despite a British blockade and international crisis, Vanderbilt pressed
0:40:15 forward, commissioning new ships, including the Prometheus, at 1,200 tons, the largest and fastest
0:40:22 of its kind at the time. In 1850, Vanderbilt traveled to London to secure critical British financing,
0:40:28 only to find the financial elite skeptical about the ambitious canal project. Matters worsened when a
0:40:33 scathing press report accused Vanderbilt’s enterprise of being an experiment in which a few
0:40:38 lawyers in Wall Street were the principal movers, their original purpose being to obtain a charter
0:40:45 and afterwards dispose of it at any good price. It was a low point in Vanderbilt’s career. Seen as
0:40:52 a fraud, he became determined to prove his critics wrong. In late 1850, undaunted by setbacks in London,
0:40:57 Vanderbilt shifted his focus from a challenging canal project toward a practical transportation route
0:41:04 across Nicaragua. Unlike the canal enterprise, which depended on numerous investors for the large capital
0:41:11 project, his new steamship line was his personal venture. The Prometheus became the first ocean-going
0:41:17 steamship entirely owned by one man. Vanderbilt’s assistant recalled, “When she started out there was
0:41:22 not a cent owing on her,” he remarking that he wanted her to go out on her own bottom.
0:41:31 In December 1850, Vanderbilt, now 57, boarded the Prometheus for his first of three crucial voyages
0:41:37 to Nicaragua. His journey was so secretive due to fears of alerting rivals that even his wife didn’t
0:41:44 know his whereabouts. Upon arrival, Vanderbilt found troubling news. His captain in Nicaragua, Colonel David
0:41:51 White, reported the steamer Orris wrecked on the rapids of the San Juan River, deeming the rapids impassable.
0:41:57 White’s repeated attempts with another steamer the director failed. Vanderbilt refused to accept defeat,
0:42:04 declaring, “I’m going up to the lake without any more fooling.” Taking command himself, he pushed the
0:42:12 little steamer through the rapids with brute force, defying his engineers’ warnings. Returning triumphantly
0:42:18 to New York, Vanderbilt boasted of the Prometheus’ unmatched speed and fuel efficiency. Ever the showman,
0:42:26 he even offered a $100,000 wager that no existing ship could surpass its performance. His innovative
0:42:31 walking-beam engine design, contrary to conventional wisdom, proved more efficient and lighter than
0:42:38 competitors’ side-lever engines. Despite significant challenges, George Law’s rival Panama route,
0:42:46 and Nicaraguan political instability, Vanderbilt established the Accessory Transit Company in
0:42:53 summer 1851. His Nicaragua transit route rapidly gained popularity thanks to his aggressive improvements,
0:42:59 competitive pricing, and sheer determination. He overcame logistical hurdles by building specialized
0:43:04 river boats, blasting through rapids, constructing a plank road, and adding more ocean-going ships.
0:43:11 Vanderbilt’s Nicaragua venture shows his remarkable ability to execute complex operations before
0:43:17 modern communications and management systems existed. Remember that this was over 170 years ago,
0:43:23 and he was coordinating ocean-going vessels, river steamboats, and overland transportation across
0:43:28 multiple countries, dealing with foreign governments and international rivals, all without telephones,
0:43:33 computers, or even telegraphs to much of his operation. It’s a reminder of how much business
0:43:40 success in this era depended on judgment, foresight, and an almost intuitive understanding of logistics.
0:43:47 In November 1851, Vanderbilt’s third Nicaragua voyage nearly ended disastrously when a British warship
0:43:54 fired warning shots, forcing him to pay a port fee. The incident triggered a diplomatic crisis resulting
0:43:59 in a formal apology from London. Once labeled a fraud, Vanderbilt was now hailed by the press,
0:44:06 which praised his indomitable resolution. Not just known for being rich, Vanderbilt was now becoming an
0:44:14 international sensation. By 1852, Vanderbilt’s Nicaraguan shipping route exploded with profits.
0:44:22 After a shipwreck near Mexico exposed his cold focus on revenue over rescue, tensions grew when his ex-partner
0:44:28 Joseph White faked British financing. Vanderbilt retaliated. He drove down Accessory Transit’s stock,
0:44:35 snapped it up cheap, then sold his fleet for $1.35 million, trapping short sellers and making a fortune.
0:44:42 Sensing his own mortality, the Commodore decided on a rare vacation in Europe, leaving trusted
0:44:47 associates in charge. Little did he know betrayal awaited while he was gone. He had never taken a
0:44:54 vacation before and he’d never take one again. His yacht, the North Star, was the largest and most
0:45:02 luxurious private vessel of its time, built at Vanderbilt’s own shipyard. At 270 feet and 2,500 tons with twin
0:45:08 walking beam engines of his own design, it featured opulent interiors decorated with rosewood furniture,
0:45:14 marble paneling, lace curtains, and ceilings adorned with paintings of American heroes.
0:45:22 Vanderbilt’s motivations for the voyage were multifaceted. After decades of relentless work, he genuinely wanted a
0:45:29 vacation. He also sought to repair strained family relationships by inviting extended family members.
0:45:34 Additionally, he viewed the trip as a chance to showcase American engineering prowess abroad.
0:45:40 As he told Senator Hamilton Fish: “I have a little pride as an American to sail over the
0:45:45 waters of England and France with such a vessel as will give credit to the enterprise of our country.”
0:45:52 Before departing, Vanderbilt carefully arranged his affairs. He removed Joseph White and his allies from
0:45:57 the Accessory Transit Company’s board, replacing them with trusted associates including Nelson
0:46:02 Robinson Robinson and Charles Morgan. However, while Vanderbilt toured Europe receiving widespread acclaim,
0:46:09 betrayal was brewing at home. Charles Morgan, whom Vanderbilt himself had appointed to the
0:46:16 Accessory Transit Board, secretly began buying up shares and aligned with Vanderbilt’s old enemy Joseph
0:46:23 White. In July 1853, they staged a coup electing themselves directors and removing Vanderbilt as the
0:46:29 company’s agent, cutting off his lucrative commissions by falsely claiming Vanderbilt was indebted to the company.
0:46:36 When Vanderbilt returned to New York in September 1853 aboard the North Star, he discovered the betrayal.
0:46:44 The Herald had already reported Morgan and White’s actions, noting ominously, “trouble is anticipated upon
0:46:50 the return of Commodore Vanderbilt.” This betrayal allegedly produced what has become one of the most famous
0:46:57 letters in American business history. Now listen to this: “Upon learning of Morgan and White’s treachery,
0:47:04 Vanderbilt supposedly penned these immortal words, ‘Gentlemen, you have undertaken to cheat me. I won’t
0:47:11 sue for the law is too slow. I’ll ruin you. Yours truly, Cornelius Vanderbilt.” The letter perfectly
0:47:19 capturing Vanderbilt’s fierce reputation, bias toward action, and blunt style is likely apocryphal.
0:47:24 Historians point out it first appeared decades later in Vanderbilt’s obituary without evidence
0:47:29 and the language used doesn’t match Vanderbilt’s usual correspondence. True or false, it captured the
0:47:36 essence of the man. Vanderbilt, known for frequent litigation since 1816, immediately filed lawsuits
0:47:42 against Morgan and White, contradicting the letter’s claim that he would not sue. The letter may be
0:47:48 myth, but Vanderbilt’s actual response was no less dramatic. He fired off a blistering public letter to
0:47:54 James Gordon Bennett, editor of the Herald, denouncing the cowardice which, in my absence in a foreign country,
0:48:01 dictated the columnist statement and calling it utterly false that he owed the company money. Far from eschewing
0:48:07 legal action, he concluded with this warning, “My rights against the company will be determined
0:48:13 in due time by the judgment of the legal tribunals.” When Morgan suggested arbitration but failed to
0:48:20 follow through, Vanderbilt escalated his retaliation with financial warfare. On January 5th, 1854,
0:48:27 he began aggressively short-selling accessory transit stock, selling thousands of shares he didn’t own
0:48:33 at $25, betting prices would collapse. Morgan, recognizing the threat, desperately bought stock
0:48:39 to maintain its price. The New York Times described the clash as a fierce contest of bull and bear,
0:48:44 pitting two seasoned, wealthy financiers against each other in a ruthless battle for control.
0:48:52 Vanderbilt doesn’t want to win, he wants to dominate. Twelve days later, Vanderbilt sprung his trap.
0:48:59 New line of steamships to San Francisco, announced the Times. While Morgan was busy buying transit stock,
0:49:05 Vanderbilt had been secretly refitting his luxury private yacht, the North Star, as a passenger liner
0:49:11 to compete directly with accessory transit. And of course, when he put it on the market,
0:49:17 the resulting fare war was unprecedented. Vanderbilt undercut the transit fare, slashing the price to
0:49:23 less than a third of the going rate. Passengers flocked to what became known as the independent
0:49:30 line, though conditions reflected the ruthless cost-cutting. The bloodletting extended beyond
0:49:37 Morgan and White. Pacific Mail and U.S. Mail steamship companies, which had long dominated the California
0:49:43 route, saw their revenues collapse as they tried to match Vanderbilt’s prices. All companies were
0:49:48 hemorrhaging money, even Vanderbilt. One of his partners who had come in on the business with him
0:49:54 actually went bankrupt, but Vanderbilt could take more pain than anyone else. By August 1854,
0:49:59 Morgan and his allies capitulated. They purchased Vanderbilt’s steamships for $800,000,
0:50:09 price far exceeding their original cost. Accessory Transit agreed to pay Vanderbilt an additional $115,000
0:50:15 for his claims of every sort. The companies quickly restored fares to their previous high levels:
0:50:24 $300 for first cabin, $250 for second, and $150 for steerage. But those who knew Vanderbilt’s history
0:50:30 remained skeptical of his promise to stay away from the California trade. After signing Morgan and his
0:50:37 allies breathed a sigh of relief. It was over. Or so they thought. In reality, it was just beginning.
0:50:51 In November 1855, Cornelius Vanderbilt orchestrated a stunning financial coup. While Morgan and his
0:50:56 allies thought the battle was over, the Commodore was buying his way back in and doing it at a discount.
0:51:04 Only, typical to him, people didn’t yet know it was him. Wall Street buzzed with news that mysterious brokers
0:51:11 were accumulating quantities of transit stock: 25,000 shares, nearly a third of all shares in existence.
0:51:18 Behind this movement, as such operations were called at the time, stood Vanderbilt and two unlikely allies:
0:51:24 Marshall Roberts of the U.S. Mail Steamship and William Aspinwall of Pacific Mail. These titans of shipping,
0:51:30 men who considered themselves Vanderbilt’s social superiors, had decided to place their fortunes in
0:51:38 his hand. Their plan was audacious: acquire accessory transit, get rid of Morgan and his allies, use Vanderbilt’s
0:51:44 cost-cutting expertise to make it profitable again, then consolidate it with U.S. Mail and create a monopoly
0:51:51 over all passenger traffic between New York and California. Roberts and Aspinwall would pocket
0:51:57 millions while Vanderbilt would rule the most vital transportation corridor in America. The Commodore,
0:52:02 who less than nine months earlier had publicly proclaimed his belief in unfettered trade and
0:52:10 unrestrained competition, was now plotting to establish the very monopoly he claimed to despise. And it’s not
0:52:14 like he was telling people what he was going to do. He was doing it through obfuscation,
0:52:21 through silence and misdirection. Little did he know that 3,500 miles away, a small man with intense
0:52:29 gray eyes was about to upend everything. On November 8th, soldiers executed General Corll,
0:52:35 a respected military commander in the central plaza of Granada, Nicaragua. The man behind his death was
0:52:40 William Walker, a slight, freckle-faced American whose penetrating gray eyes captivated everyone he
0:52:45 met. Though he looked more like a priest than a revolutionary, Walker had just seized control of
0:52:51 Nicaragua. Walker was a filibuster, not in the parliamentary sense of the word. He was a private
0:52:58 citizen leading armed invasions of foreign lands under the guise of patriotic expansion. Born in Nashville
0:53:05 and trained as a doctor and lawyer, he previously led a failed invasion of Mexico. Undeterred, Walker
0:53:11 arrived in Nicaragua in 1855 with only 56 men, initially hired as mercenaries to fight for the
0:53:18 liberal faction in Nicaragua’s civil war. His victory hinged on one brilliant maneuver:
0:53:24 commandeering an accessory transit steamboat on Lake Nicaragua and capturing the conservative
0:53:29 stronghold at Granada from behind. By taking prominent conservative families hostage,
0:53:36 Walker forced General Corll into surrender. Walker established a puppet government headed by Patricio
0:53:42 Rivas, a weak leader he easily controlled. Shortly after, Walker accused Corll of treason,
0:53:47 orchestrated a quick trial by his own men, and executed him publicly, consolidating his power.
0:53:53 Yet Walker knew his survival depended on reinforcements from the United States, making
0:53:59 him dangerously reliant on Vanderbilt’s accessory transit company, a company Vanderbilt was determined
0:54:05 to reclaim. Walker’s initial attempts to negotiate with transit executives Joseph White and Cornelius
0:54:12 Garrison failed. Enter Edmund Randolph, a Virginia aristocrat and friend of Walker who proposed a daring
0:54:19 conspiracy to Cornelius Garrison, transit San Francisco agent. Randolph intended to revoke the existing
0:54:26 charter and grant a new charter to himself, cutting Vanderbilt out entirely. After initial hesitation,
0:54:33 Garrison sent his son William to Nicaragua to secure Walker’s agreement. Walker enthusiastically accepted
0:54:39 Randolph’s scheme, providing legal justification for cancelling Transit’s charter. By late December,
0:54:44 Walker awarded the new transit rights to Randolph who immediately sold them to Garrison and Morgan.
0:54:48 In return, they promised Transports Walker reinforcements at no cost.
0:54:55 Meanwhile, Vanderbilt continued buying accessory transit stock, oblivious to the conspiracy forming
0:55:01 behind him. Walker represented a threat Vanderbilt had never faced, someone wielding an armed force
0:55:07 behind the reach of Vanderbilt’s usual tactics of financial warfare or intimidation. Vanderbilt was forced
0:55:10 to enter the dangerous realm of international intrigue.
0:55:17 Sylvana Spencer, a sailor known for his toughness and intimate knowledge of Nicaragua’s transit routes,
0:55:23 became Vanderbilt’s unlikely hero. Armed with Vanderbilt’s backing and $40,000, Spencer traveled to Costa Rica
0:55:32 and convinced President Juan Rafael Mora to help sever Walker’s supply lines. On December 23rd, 1856,
0:55:37 Spencer’s troops silently overtook the filibuster garrison at Hips Point and captured Walker’s steamboats
0:55:44 one by one, using Spencer’s expert knowledge to avoid suspicion. Spencer’s campaign culminated at San
0:55:49 Carlos, a strategic fortress where he secured a bloodless surrender, crippling Walker’s supply lines.
0:55:57 With his resources cut off, Walker’s position rapidly deteriorated. Following a prolonged siege,
0:56:05 Walker surrendered on May 1st, 1857 and was safely escorted from Nicaragua. But Walker didn’t abandon his
0:56:11 ambitions. In November, he attempted another invasion but was swiftly captured and forced to surrender by
0:56:17 the U.S. Navy. His final expedition ended tragically when the British forces captured him and delivered
0:56:23 him to the Honduran authorities, who executed him by firing squad on September 12th, 1860.
0:56:31 Vanderbilt’s enemies fell one by one. After breaking Walker, he turned his focus to exacting revenge on
0:56:38 Garrison and Morgan. When Garrison faced arrest in New York for alleged frauds exceeding half a million
0:56:43 dollars during his tenure as transit company agent, he attempted reconciliation with Vanderbilt.
0:56:47 Visiting Vanderbilt, Garrison proposed collaborating on the Walker grant.
0:56:53 Vanderbilt sternly refused, emphasizing his actions were solely for the benefit of transit
0:56:59 company and its shareholders, not for personal gain. Simultaneously, Vanderbilt intensified his
0:57:05 dominance of the California steamship traffic and boldly targeted the Atlantic shipping lanes.
0:57:11 On December 10th, 1855, thousands watched at Simpson’s shipyard as Vanderbilt launched the
0:57:19 largest steamship of its era, aptly named the Vanderbilt. At 335 feet long with massive 42-foot
0:57:27 diameter side wheels and five decks, it cost over $900,000, a clear demonstration of Vanderbilt’s wealth
0:57:31 and determination to defeat the heavily subsidized Collin and Canard lines.
0:57:38 The Vanderbilt’s maiden voyage in May 1857 was a stunning success, reaching England in
0:57:44 record time. Newspapers lauded its unprecedented speed and luxury, prompting Vanderbilt to aggressively
0:57:51 cut fares and strategically timed departures to undermine competitors. By 1860, the strategy had
0:57:58 dismantled the Collins Line, forcing it to sell off its ships. In 1860, Vanderbilt also achieved total
0:58:03 control of the California steamship traffic through an agreement with William Aspinwall,
0:58:07 dividing the business between Vanderbilt’s Atlantic and Pacific steamship company
0:58:14 on the Atlantic side and Pacific Mail on the Pacific side. Despite years spent dismantling monopolies
0:58:20 through fierce competition, Vanderbilt pragmatically created his own monopoly once victorious, stabilizing
0:58:26 fares and securing consistent profits. Vanderbilt’s influence was so immense that when the California
0:58:32 postal contract ended in 1860, he boldly refused to carry the mail, threatening communication between
0:58:39 coasts. This prompted President Buchanan’s personal intervention, promising Vanderbilt retroactive
0:58:42 payment from Congress to maintain essential services.
0:58:48 Even as Vanderbilt dominated ocean transportation, he began extending his reach into railroads. His
0:58:55 involvement with the New York and Harlem Railroad began in 1857 when he joined its board alongside his son-in-law,
0:59:01 Horace Clark and financier Daniel Drew. The company faced bankruptcy with large debts due amid the
0:59:09 panic of 1857. Vanderbilt’s code of honor distinguished him in a crisis. When Drew refused
0:59:15 to endorse the renewal of the railroad’s notes despite having accepted a commission, Vanderbilt confronted him
0:59:22 directly. Mr. Drew, Vanderbilt declared, are you going to sign all these acceptances? Not one of them,
0:59:28 Drew objected. Are you crazy? I’m going to sign all these and you are too, Vanderbilt insisted.
0:59:34 Where’s the money to come from to pay for it, Drew asked. You and I will pay for it if no one else does,
0:59:40 Vanderbilt replied firmly. I’ll do it if it takes the code off my back. I always honor my commitments.
0:59:47 Drew eventually signed, nearly in tears. Vanderbilt later recounted with satisfaction,
0:59:53 he did not dare cheat me. This incident highlighted Vanderbilt’s growing authority and strict adherence
0:59:57 to business commitments, qualities that would prove vital as he expanded further into railroads.
1:00:05 Drew would soon want revenge, but for the moment he waited. By 1860, Vanderbilt had achieved immense
1:00:11 influence, described by the Chicago Tribune as almost knightly power. He controlled the Atlantic steamship
1:00:17 traffic. He was the largest shareholder in Pacific mail and held prominent positions in New York’s Harlem and Erie
1:00:24 railroads. His estimated wealth of around 11 million likely made him America’s richest private citizen.
1:00:30 Vanderbilt represented something new in American business, a man whose wealth and power transcended the
1:00:37 categories of the past. Beyond historical analysis, men followed this demanding profane titan out of
1:00:45 genuine respect. When Captain Ludlow of the aerial died at sea during a fierce storm in December 1859,
1:00:49 his final words were, “Tell the Commodore I died at the post of duty.”
1:00:57 This loyalty reflected Vanderbilt’s core qualities. No one understood steamships better,
1:01:00 took greater personal risks, or was more committed to keeping his word.
1:01:06 As America entered the turbulent 1860s, Vanderbilt stood unmatched in power.
1:01:15 He was hated, admired, resented, yet always respected, even by his enemies.
1:01:25 As Cornelius Vanderbilt approached 70 in 1864, most men his age were considering retirement.
1:01:31 Vanderbilt, however, was not most men. He’s an outlier and he was planning his greatest conquest
1:01:38 yet. After decades dominating American waterways, the Commodore was now transforming himself into
1:01:45 the railroad king. The stakes were immense. In an era before automobiles, highways, or air travel,
1:01:51 railroads were essential to American commerce. The rail network represented far more than transportation.
1:01:57 It was, according to a contemporary observer, “the most tremendous and far-reaching engine of social
1:02:05 revolution which has ever either blessed or cursed the earth.” Just as steamboats had reshaped America
1:02:12 decades earlier, railways now dramatically altered geography, economy, and society. Cities like Chicago
1:02:21 grew exponentially, increasing from 43,000 people in 1850 to 400,000 people by 1870, driven primarily by its
1:02:32 the most critical rail corridor in America. Vanderbilt’s railroad empire began with
1:02:39 its purchase of the struggling New York and Harlem Railroad in 1863, a small line critics dismissed as
1:02:45 “the only good for wrapping paper.” Vanderbilt, however, saw potential where others saw failure,
1:02:51 aiming to create the only direct rail connection between New York City and the industrial heartland
1:02:57 of New England. Driven by pride and a relentless pursuit of efficiency, Vanderbilt acquired the Hudson River
1:03:06 Railroad in 1864, securing control over the only railways entering Manhattan. Yet, this is merely the starting point.
1:03:13 To access the lucrative Midwest markets, Vanderbilt needed cooperation from New York Central Railroad,
1:03:18 a major trunk line running from Albany to Buffalo. For three years, Vanderbilt patiently
1:03:24 negotiated with the Central’s presidents, Ernest Corning and then Dean Richmond. Frustrated by the
1:03:30 Central’s practice of diverting his railcars to competing steamboat lines, Vanderbilt repeatedly
1:03:37 voiced his complaints. Though Vanderbilt preferred diplomacy to confrontation, a proposed merger between
1:03:43 the railroads faced strong opposition. His lieutenant, Horace Clark, warned that such a move would shake the
1:03:51 state to its center, appearing as an attempt to strengthen railroad monopolies. In August 1866,
1:03:57 the landscape changed suddenly when Richmond died. Henry Keep, the Central’s new president, was a secret
1:04:05 strategic thinker openly hostile to Vanderbilt. Keep vowed privately to take revenge against Vanderbilt,
1:04:13 even if it cost him half his wealth. The breaking point came in December 1866, when Keep abruptly revoked
1:04:19 a hard-fought agreement to pay the Hudson $100,000 annually for handling the New York Central traffic
1:04:26 into New York City. So on December 29th, Vanderbilt met with Keep and his allies. William Vanderbilt
1:04:32 repeatedly questioned Keep asking, “Gentlemen, you have repudiated our contracts and disrupted our
1:04:39 established agreement. Do you have any alternative to propose?” Keep responded coldly, offering only minimal
1:04:44 compensation. After five hours of fruitless discussion, Vanderbilt drove Corning, a more
1:04:50 reasonable central director, to his hotel. “Mr. Corning, I’m very sorry we cannot get along together
1:04:56 in this manner,” Vanderbilt remarked. “I am too,” Corning replied. “If it was left to just you and me,
1:05:02 we could fix it in a little while. I believe we could,” the Commodore agreed. But this brief exchange
1:05:07 clarified for Vanderbilt that Corning had no real authority. Keep held all the power, making further
1:05:17 negotiations pointless. Soon after, Vanderbilt unleashed his most powerful weapon. On January 14th, 1867, the
1:05:23 boards of the Hudson River and Harlem Railroads voted to sever all ties with the New York Central Railroad.
1:05:29 They refused to accept any tickets or freight from the Central and halted all train crossings over the
1:05:37 Albany Bridge. This decision amounted to a declaration of economic war with immediate and severe consequences.
1:05:42 “It would place the New York Central Railroad in a position where it could no longer claim to be a
1:05:49 primary trunk line between New York and Buffalo,” explained William Vanderbilt. “Amid a fierce snowstorm that
1:05:55 paralyzed New York State, passengers were forced to cross the frozen Hudson River at Albany on foot or hire
1:06:01 sleighs for transportation. Freight shipments from the west piled up, and alternative railroad connections
1:06:08 dependent on unreliable ferry crossings due to severe weather failed to meet the demand.” Effectively,
1:06:13 what’s happened here is Vanderbilt has isolated New York City from the rest of the world. He literally
1:06:20 controls the ingress and egress through railroad lines, and he’s said no. The Brooklyn Eagle accused
1:06:25 Vanderbilt of placing the city under strict blockade, describing his actions as criminal and deserving,
1:06:31 exemplary punishment. When called before a legislative committee, Vanderbilt bluntly defended himself.
1:06:37 When you talk about legally, I suppose your next question will be why didn’t you prosecute them?
1:06:43 It is not according to my mode of doing things to bring a suit against a man that I have the power in
1:06:50 my own hands to punish. The law as I view it goes too slow for me when I have the remedy in my own hands.”
1:06:57 This was a striking display of private power overriding public interest. One man’s ability
1:07:04 to disrupt a major city’s commerce for personal corporate objectives. If you were to judge this
1:07:09 solely on its effectiveness, then you would conclude it worked and it worked quickly.
1:07:15 Keep quickly capitulated. On January 17th, he urgently telegraphed Corning what is to be done.
1:07:21 He handed full authority to settle the dispute to Corning and two other directors more inclined
1:07:28 towards compromise. The trio promptly visited Vanderbilt’s office to negotiate peace. One director
1:07:34 later acknowledged that Vanderbilt was the most eager to resolve the situation. On January 19th,
1:07:38 a new agreement was finalized. The Central Railroad promised to deliver as much freight to the Hudson
1:07:43 River Railroad as it received from them, ensuring no more empty cars returned from Albany. It also
1:07:51 agreed to cover a portion of the terminal expenses. Keep was publicly humiliated. John M. Davidson wrote
1:07:56 to Corning that Keep and Lockwood are large sellers. They flooded the market with stock. The swearing against
1:08:01 Keep by the stockholders is intent. They’re considering a meeting to demand his resignation.
1:08:07 So basically, Keep gets outmaneuvered by Vanderbilt. He dumps the shares. Davidson is telling us that
1:08:12 Keep and Lockwood are both just flooding the market with their shares. So the share price is sinking.
1:08:18 What Davidson did not yet realize, but Vanderbilt clearly saw, was the exceptional opportunity the
1:08:25 crisis presented. As Keep and his partner dump their shares, Vanderbilt starts acquiring them.
1:08:32 This marked a decisive shift in his tactics. After three years of diplomacy, he now aggressively moved
1:08:38 to secure ownership, taking advantage of Keep’s weakening position. By the Central’s annual meeting
1:08:45 in December 1867, Vanderbilt had acquired enough stock to seize control. His allies, including William
1:08:50 Clark and Schell, were elected to the board. Keep’s presidency ended, and when Corning nominated
1:08:57 Vanderbilt as president, the outcome was inevitable. In just four years, Vanderbilt had progressed from
1:09:03 controlling the modest Harlem Railroad to dominating one of America’s major rail networks.
1:09:10 The event underscores a critical lesson about leverage and power. Keep had mistakenly believed that his title
1:09:15 as president granted him control, but Vanderbilt understood that true power came from ownership.
1:09:22 Titles alone didn’t guarantee authority. CEOs holding little equity can be removed by boards or investors,
1:09:27 whereas those with controlling stakes can dictate strategy and vision despite opposition.
1:09:32 I just want to recap here for a second. Keep and Vanderbilt get into this fight.
1:09:37 So Vanderbilt effectively humiliates Keep. Keep dumps the shares, because he’s like,
1:09:43 he knows he’s getting ousted. So he starts dumping all his shares. Then Vanderbilt buys the shares. So the
1:09:49 shares at depressed prices. So he effectively causes the share price to lower, and then buys the shares and
1:09:56 takes control. This isn’t the first time he used this play bug. So with control of both the Hudson River and
1:10:02 New York Central Railroads, Vanderbilt revived his earlier proposal for consolidation. Persistent
1:10:07 conflicts between these interconnected lines had proven impossible to resolve through contractual
1:10:12 agreements alone. A merger would align their interests and eliminate structural inefficiencies.
1:10:19 So in 1869, Vanderbilt successfully secured legislation permitting the merger. The resulting
1:10:24 New York Central and Hudson River Railroad was among America’s largest enterprises, boasting a
1:10:30 capitalization of approximately $90 million in dominating the crucial transportation corridor from
1:10:36 New York to Buffalo. This consolidation represented more than just another business transaction.
1:10:43 It marked a fundamental transformation of American capitalism. Vanderbilt helped pioneer the concept
1:10:48 of the giant corporation distinct from the individual ownership or management. By merging older
1:10:54 railroad companies into a single entity focused on efficiency and profitability, he also shifted
1:11:01 their original public service missions. The concentration of economic power raised concerns.
1:11:06 It’s not a pleasant reflection, wrote Harper’s Weekly, that the great thoroughfare between the East
1:11:13 and the West is in the hands of the Vanderbilt family. Despite these anxieties, Vanderbilt’s consolidation
1:11:19 brought clear economic advantages. Resolving conflicts between the Central and Hudson River lines reduced delays,
1:11:23 reduced delays, simplified operations, and significantly lowered costs.
1:11:26 By 1870,
1:11:31 Cornelius Vanderbilt had fundamentally reshaped American business. In just four years, he transformed himself from
1:11:38 the Commodore of the Waterways into the Railroad King, building one of America’s most significant business empires.
1:11:44 Vanderbilt’s railroad consolidation mirrored broader economic trends, the emergence of large
1:11:50 corporate enterprises, increasingly abstract ownership structures, and concentrated economic power.
1:11:56 He demonstrated both the benefits and the risks of this new corporate model. His railroad empire achieved
1:12:03 economies of scale that lowered transportation costs and boosted economic growth. However, his blockade of New York
1:12:09 raised troubling concerns about the extent of private influence within a democratic society.
1:12:16 As Vanderbilt, now 75, surveyed his empire, he saw a nation transformed, not merely by railroads,
1:12:20 but by the corporate structures he pioneered to build and manage them.
1:12:27 William Lloyd Garrison had envisioned that improved communication and connections would unify societies,
1:12:29 promoting common values and shared prosperity.
1:12:36 Vanderbilt indeed united distant regions with iron rails, but the legacy of his work was not
1:12:40 democracy or equality. It was the modern corporation itself.
1:12:52 A statue of Cornelius Vanderbilt stands at the entrance of New York City’s Grand Central Terminal,
1:12:58 overlooking Park Avenue South and the empire that he created. The infrastructure he built remains essential,
1:13:05 even as the original corporation and dynasty established has faded. Yet, as Vanderbilt’s railroad
1:13:10 directors noted after his death, this work will go on, though the master workman is gone.
1:13:17 Cornelius Vanderbilt is often portrayed as a ruthless Robert Barron, but the reality is more nuanced. He
1:13:23 embodied fascinating contradictions, a fierce competitor who preferred diplomacy, a tough negotiator who
1:13:29 carefully balanced aggression with patience. His railroad empire consolidating the Harlem, Hudson River,
1:13:36 and New York Central railroads was built only after repeated attempts at peaceful negotiation failed.
1:13:42 Vanderbilt’s mergers produced a corporate giant from Manhattan to Lake Erie, ushering in bureaucracy,
1:13:49 delegation, and unprecedented efficiency. By his death, he reportedly held one-ninth or one-twentieth,
1:13:53 depending on how you count it, of all U.S. currencies, sparking debate over his wealth,
1:14:00 democracy, and the unsettling power of massive corporations. America had entered its era of great
1:14:07 fortunes, and Vanderbilt had led the way. Vanderbilt’s legacy is nearly entirely heroic nor villainous,
1:14:12 but reflects America’s shift from rural merchants and farmers to corporate industrialism. He was an
1:14:19 individualist who built institutions, a practical navigator who pioneered an abstract economy. He was
1:14:25 at the forefront of the industrial revolution. His relentless drive and continual reinvention
1:14:33 defined not just his life but also the nation’s transition into modern times. As his railroad directors
1:14:38 aptly summarized Vanderbilt’s greatest monument was the lasting framework he established. The work will go
1:14:48 on, though the master workman is gone.
1:14:54 All right, I want to cover a few reflections before we get into the lessons that you can take away from
1:15:01 this. This guy is such a badass. He’s done so many things. So there’s so many points in this story,
1:15:06 like this is a skeleton of his life. We missed a whole bunch of things. I’m going to tell you a few
1:15:11 of them. But each of these things could be their own episodes, like each of these little battles on
1:15:18 the seas or the Nicaragua thing or the railroad battles. Like this is crazy. We didn’t even cover
1:15:24 the Erie battle with Jay Gould and Daniel Drew comes back for that one. And we just didn’t have time
1:15:28 because I want to keep these reasonably short. So we’ll cover some of this more in the future. But I
1:15:34 wanted to give you a sketch of the person and some of the things you can learn from him. Now we didn’t
1:15:41 have time to get into this either. But Vanderbilt was not a role model as a parent or partner. I mean,
1:15:47 he applied a lot of the same tactics that he championed in business. He applied at home and
1:15:52 they had a much different result. Instead of leading to success, it led to disaster.
1:15:57 Another fascinating angle to this that we’ll maybe cover in another episode in the future is
1:16:04 how his heirs managed to squander the world’s largest fortune in only a few generations. It’s a
1:16:11 story that involves New York society, royalty, lavish parties, wives trying to one up each other,
1:16:16 legal battles and so much more. Interestingly, Anderson Cooper wrote a book on this and he
1:16:23 would know because he is after all a Vanderbilt. You can take your learning to the next level for
1:16:28 these two. Like one of the things that people email me and they’re like, what book did you use? So we
1:16:34 highlight the books we used for this. It was Tycoon’s War and we used the first tycoon. We also put my
1:16:39 highlights into the repository that you can access. So if you’re a member at Farnham Street, if you go
1:16:45 to fs.blog/membership, you can actually search all my highlights from all the books and all the episodes
1:16:51 and see what I underline when I was reading the book. Okay, I want to get into some of the lessons that we
1:16:58 can take away from Vanderbilt and how we can use them and maybe apply them in life. So the first lesson
1:17:03 is ride the wave. When a better technology came along, Vanderbilt jumped on it. He went from
1:17:08 various to steamships to railroads without trying to cling to the past. The guy did not think about
1:17:13 sunk costs. He went all in and I admire that about him. A lot of people would have been trying to
1:17:20 sort of walk that line between both, but not Vanderbilt. He went all in. Two, patience. He didn’t need
1:17:25 quick wins. He wasn’t looking for validation from other people. He’d rather take a temporary loss if it
1:17:31 meant owning the market later. He would always do what was in the long-term interests of himself and not
1:17:36 the short-term interests. Which leads me to three, which is his ability to take pain. Physical
1:17:41 pain from powering through blizzards when no other ferry captain would. Financial pain from slashing
1:17:48 prices to zero profit and sometimes at a loss just to drive out rivals. Psychological pain threatening to
1:17:53 block rail traffic to and from New York City and then doing it. And he survived all these scenarios and
1:17:59 crushed everyone else. The man could take more pain than almost anybody I’ve studied.
1:18:05 Four, control. Vanderbilt wasn’t really interested in being a passive shareholder. He wanted control
1:18:09 or nothing. He didn’t want to sit on the sidelines and watch somebody else do it. He wanted to lead.
1:18:15 Five, showmanship. It’s easy to root for the underdog and Vanderbilt often positioned himself that way
1:18:20 against a big monopoly. Then once he beat them, he essentially became the monopoly. But by that point,
1:18:26 he already had public sympathy on his side. And he was also a bit of a showman too. Whether racing
1:18:33 steamboats or blocking the rails, he made business feel like high drama. And that’s part of why his legend
1:18:37 endures today. He was always the talk of the town, even when he was the one pulling the strings behind
1:18:45 the scenes. Six, go all in. If you cross Vanderbilt, it wasn’t enough for him to beat you. He wanted to
1:18:52 finish you financially or otherwise. He didn’t just win, he dominated. Seven, positioning. Vanderbilt operated
1:18:59 with very little leverage so he could always take advantage of his rivals’ misfortunes. He also would cause
1:19:03 poor positioning in other people. He knew when people were selling or buying, he would often force
1:19:08 them to sell and he would short the stock. They would sell, it would drive down the price and then
1:19:13 he’d buy it back and he’d either take control. He was always in a position to capitalize on the
1:19:20 circumstances that forced other people into bad hands. Eight, move in silence. Yes, he might say I’m
1:19:26 going to ruin you, but he rarely telegraphed how he’d do it. He made clandestine stock purchases,
1:19:32 he turned enemies into allies and he pulled off secret deals. By the time rivals realized it was
1:19:38 too late. Nine, make money. Vanderbilt made money in many ways. It reminds me of a quote by John D.
1:19:43 Rockefeller who said, “I have ways of making money that you know nothing of.” Vanderbilt made money on
1:19:49 competing. He made money from not competing. He made money from monopolizing and he understood where the
1:19:53 real money was, like the lucrative mail contracts from New York to San Francisco.
1:19:59 And that’s the lessons you can take away from this. Thank you for listening and tune in next time.
1:20:17 Thanks for listening and learning with us. For a complete list of episodes, show notes,
1:20:23 transcripts, transcripts, and more, go to fs.blog/podcast or just Google the Knowledge Project.
1:20:27 The Farnham Street blog is also where you can learn more about my new book,
1:20:33 Clear Thinking: Turning Ordinary Moments into Extraordinary Results. It’s a transformative
1:20:40 guide that hands you the tools to master your fate, sharpen your decision-making, and set yourself up for
1:21:00 unparalleled success. Learn more at fs.blog/clear. Until next time.

0:00:03 The fundamentals of investing hasn’t changed at all.
0:00:08 Buying great things or great businesses, holding for long periods of time, earning cash returns.
0:00:11 What’s changed is the environment around it.
0:00:14 The whole backbone of the world is changing.
0:00:21 Behind your phone or your computer, you can have this podcast on your cell phone and go for a run in the morning.
0:00:31 How that gets delivered to you is data center storing it, fiber delivering it to you, going to a tower and bringing it down to your phone wireless.
0:00:37 And all of that needs enormous amounts of infrastructure, and all of that is built by private enterprise.
0:00:46 50% of the backbone of what we own today did not exist as an asset class for investment 20 years ago.
0:00:49 Well, you have over a trillion dollars in management now.
0:00:51 It sounds like a lot of money.
0:00:53 It is a lot of money.
0:00:54 It’s a trillion dollars.
0:00:58 But it’s not that much when you do what we do.
0:01:08 Welcome to The Knowledge Project.
0:01:10 I’m your host, Shane Parrish.
0:01:16 In a world where knowledge is powered, this podcast is your toolkit for mastering the best of what other people have already figured out.
0:01:26 If you want to take your learning to the next level, consider joining our membership program at fs.blog.com.
0:01:38 As a member, you’ll get my personal reflections at the end of every episode, early access to episodes, no ads, including this, exclusive content, hand-edited transcripts, and so much more.
0:01:41 Check out the link in the show notes for more.
0:01:45 Most investors see markets as a race to outperform every quarter.
0:01:49 Our guest today, however, sees them as a marathon measured in decades.
0:01:59 As CEO of Brookfield Asset Management, he’s quietly spent decades building a trillion-dollar business, investing patiently in the invisible machinery of the global economy.
0:02:13 While others chase short-term returns, Flat position Brookfield to capitalize on massive global shifts from digitalization and low-carbon energy to a reshaped global supply chain, years before they appeared on anyone else’s radar.
0:02:22 In this rare public conversation, it’s only the second podcast he’s ever done, Flat reveals not just what he invests in, but how he thinks.
0:02:35 From spotting trends early to structuring deals for resilience across economic cycles to placing big, bold bets that compound steadily over time, he offers a masterclass in patient, disciplined investing.
0:02:50 Whether you’re allocating capital, building a business, or simply navigating uncertainty, you’ll learn how one of today’s most influential but private investors sees around economic corners and why his ability to ignore short-term noise might be his greatest competitive advantage of all.
0:03:02 I want to start with how investing has changed over the past 23 years, I think, since you’ve been CEO.
0:03:06 Look, on the first level, I’d say it hasn’t changed at all.
0:03:17 What investing is about is to buying great things or great businesses, holding for long periods of time, earning cash returns, and that hasn’t changed at all.
0:03:21 So, the fundamentals of investing are exactly the way they were before.
0:03:24 What’s changed is the environment around it.
0:03:27 And I mentioned a couple things.
0:03:31 First one is many businesses are publicly traded.
0:03:40 And the indexing and passive investing has changed the publicly traded market for investments.
0:03:44 It’s very different than the actual investments.
0:03:46 The investments are still the same, and what we do is still the same.
0:03:53 How they trade in the market and whether they’re included in indexes has changed how they trade in the public markets.
0:03:58 So, I think that is probably the fundamental biggest thing.
0:04:14 The second thing, and this is, I’d say maybe the most simple way to say it is, 50% of the things that we invest in today did not exist as an investment asset class for investors like us 20 years ago.
0:04:16 50%.
0:04:19 And we invest in the backbone of the global economy.
0:04:20 Like, these are simple things.
0:04:22 We deliver your water in the morning.
0:04:25 We toll the road you drive on in the afternoon.
0:04:29 We deliver your power to your house.
0:04:34 We, the data center that powers your phone, we own.
0:04:38 Those are all really backbone things.
0:04:39 So, what we do is backbone.
0:04:43 This is not innovative venture capital that we’re doing.
0:04:51 But 50% of the backbone of what we own today did not exist as an asset class for investment 20 years ago.
0:05:01 What percentage of that would you say is new things versus governments maybe privatizing some of the services they used to deliver?
0:05:06 When we started in infrastructure 25 years ago, we were among the first.
0:05:10 We thought that it would be governments privatizing.
0:05:12 And to some extent, it is.
0:05:15 And it’s not, they’re not privatizing because they have a hard time selling assets.
0:05:19 What they do is they’re just not investing.
0:05:20 Therefore, private enterprise takes it up.
0:05:29 But the biggest area of investment today is really just the whole backbone of the world is changing.
0:05:37 So, the digitization of the whole world behind your phone or your computer.
0:05:42 As you know, laptops didn’t exist before.
0:05:43 The internet didn’t exist before.
0:05:45 Cell phones didn’t exist before.
0:05:50 Today, you can have this podcast on your cell phone and go for a run in the morning.
0:06:01 How that gets delivered to you is data center storing it, fiber delivering it to you, going to a tower and bringing it down to your phone wireless.
0:06:05 And all of that needs enormous amounts of infrastructure.
0:06:08 And all of that is built by private enterprise.
0:06:16 Virtually every, in fact, not virtually, all of that is delivered to you as an individual.
0:06:21 And this is 8 billion people in the world getting that delivered to them in various forms.
0:06:23 It’s all delivered by private money.
0:06:25 And that’s what’s changed.
0:06:29 It’s before, historically, that was built out by governments.
0:06:33 Today, it’s being built out by private enterprise.
0:06:37 You know, to use an example, we own all of the telecom towers.
0:06:41 Not all, but we own a very substantial portion of the telecom towers in India.
0:06:49 They deliver all the phone and wireless infrastructure to many individuals in India.
0:06:52 And that was originally built by Reliance Industries, GEO.
0:07:01 We bought it from them and we support their and other telecom companies’ activities through those telecom towers.
0:07:04 And historically, that would have been built by government.
0:07:08 But it was, that’s built by private enterprise.
0:07:14 Let’s go back to the rise of passive, maybe versus historically more active investing.
0:07:15 What implications do you see?
0:07:17 What opportunities are created?
0:07:24 Look, in everything, when I say there’s a problem, there’s always an opportunity.
0:07:27 And I think that’s the Chinese symbol, right?
0:07:28 Problem and opportunity.
0:07:33 For some companies, smaller, midsize, don’t fit indexes.
0:07:42 They will be lost within public markets investing because active investors may not be investing in those sectors anymore.
0:07:45 And if you don’t fit the indexes, you have no buyers.
0:07:59 Increasingly, though, what it’s doing is that it’s creating a large disparity in some securities at points in time between the price of them in the market and the value of the underlying assets.
0:08:04 Back to, you asked me first question, what has changed in the investing world?
0:08:05 And I said nothing.
0:08:07 That’s related to value.
0:08:13 What’s changed is the price of some things trades up and down.
0:08:22 If over the last 18, 24 months, if you’ve been one of the big technology stocks in the world, everyone needed or wanted to buy you in the indexes.
0:08:25 And therefore, their multiples traded very high.
0:08:34 But if you were something that didn’t neatly fit the indexes, it traded at a low price.
0:08:38 The opportunities are that we can take those companies private.
0:08:42 So, we took a large container shipping company private.
0:08:46 It had one analyst and nobody following it.
0:08:48 It fit in no indexes.
0:08:50 It was a $6 billion company.
0:08:52 And we took it private.
0:08:54 And it’s been an exceptional investment.
0:09:05 So, we continue to, I’d say, capitalize on opportunities where we understand the value and the price is not trading at that in the markets.
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0:09:13 It’s about having the right systems behind it.
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0:10:39 If you want to get something done right, you need the right system.
0:10:42 Our team learned firsthand when shipping out my books.
0:10:43 It sounds simple.
0:10:44 Print a label.
0:10:45 Send a package.
0:10:49 But when you’re handling orders at scale, the complexity adds up fast.
0:10:51 That’s why I use ShipStation.
0:10:56 You can focus on other parts of your business because you never have to worry about shipping and fulfillment.
0:11:00 Again, with ShipStation, help eliminate the busy work.
0:11:04 Instead of jumping between platforms, I manage everything in one place.
0:11:11 It automatically finds the best rates, prints labels, in a click, and tracks shipments without thinking about it.
0:11:14 ShipStation lets me focus on what actually matters.
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0:11:59 What can you do with a private company that you can’t do with a public company?
0:12:04 Well, firstly, you don’t have to look at what the price is versus the value.
0:12:07 You just know what the value is and you run it for what it is.
0:12:18 But secondly, we can operate differently, finance differently, invest for the future, and run a business like somebody should just run it.
0:12:28 If you and I owned a business privately, we wouldn’t care about whether the stock went up or down tomorrow morning.
0:12:29 We just run our business.
0:12:30 Cash flow comes out.
0:12:34 We decide, should we divin it out to ourselves to use together?
0:12:36 Or should we keep it in the business and invest?
0:12:45 And that’s really the difference is all you look at is the fundamentals of your business if you’re private.
0:12:56 And if you’re public, people tend to get distracted by the trading price of the security when it’s not really relevant.
0:13:03 Some businesses need access to capital and have to raise capital and therefore their price is important.
0:13:09 But most businesses that are listed don’t need access to capital.
0:13:15 They’re only listed because they’re large and they happen to be just – they need owners and therefore they’re in the public markets.
0:13:22 They’re never issuing equity and therefore the price of the security in the market really doesn’t matter.
0:13:35 And in fact, it’s a distraction, which is why when people often ask me what happened with the alternatives industry and why did it grow the extent that it grew over the last 25 years?
0:13:51 And it’s really grown that way because private assets are – the fundamentals are exactly perfectly matched to the fundamentals of what institutional investors want to have in their portfolios.
0:14:00 And maybe even more importantly, by owning them privately, they don’t have to have the distraction of the public market.
0:14:07 They don’t have to get confused that you and I bought a telecom tower business.
0:14:10 It generates a 6% yield.
0:14:13 It grows at 4% every year.
0:14:17 And we don’t have to invest much cash flow into it.
0:14:18 So, it’s free cash flow.
0:14:26 And if it’s privately owned, it’s just – we just watch the cash flow and keep growing and try to enhance the business and grow it.
0:14:27 And that’s what we do privately.
0:14:36 If it trades in the public market and today it’s worth $20 and tomorrow because of whatever happens in the markets, it’s worth $10, nothing changed in the business.
0:14:43 And that distraction is what causes people issues.
0:14:45 They sometimes make rash decisions.
0:14:55 And I’d say that’s maybe the biggest enhancement to long-term investors by having private assets.
0:14:58 I take it you’re not an efficient market hypothesis person.
0:15:01 You know, I – no.
0:15:02 The answer is no.
0:15:07 The markets are never efficient.
0:15:13 In fact, very seldom do they ever trade at the actual value of securities.
0:15:18 Most of the time, they trade above or below.
0:15:21 Very seldom do they trade at the value.
0:15:23 But yes, I guess there are many theories in life.
0:15:34 Let’s talk about some of the trends going on in the world today that you see from your aperture that you think have a long runway that we’re maybe just beginning on or maybe in the middle endings on.
0:15:44 So we generally have three sort of themes that we invest around or – we have a few themes we invest around at all points in time.
0:15:44 Today we have three.
0:15:56 The first one is just the digitalization of everything and the amount of capital that’s being invested behind that digitalization.
0:16:18 And really what it is is there are many, many, many, many, many trillions of dollars going into the movement of information into the cloud, onto your phone, and just the digitalization of everything behind it.
0:16:34 And that has been enhanced, increased, enhanced, by artificial intelligence and the networks being set up now to harness artificial intelligence.
0:16:42 And maybe the most simplest way to explain it is everyone thinks of artificial intelligence as chat GPT.
0:16:48 I’m going to get it to write my cooking class memorandum.
0:16:58 But really what the – where the money is going to be made is the application of artificial intelligence into business.
0:17:14 And simply stated that’s taking processes in service and industrial businesses and making them more efficient by using advanced robotics who have learned how to make –
0:17:20 how to run those processes from models run on artificial intelligence.
0:17:23 And we’re in the very, very early stages of that.
0:17:36 But from an infrastructure standpoint, the amount of money being put behind this is in amounts which have almost never been seen invested before.
0:17:40 So that’s sort of the first theme we have of investment.
0:17:50 And it both affects our operating businesses because we’re now applying artificial intelligence in our business to make them better and they’ll be more productive.
0:17:59 And we’re also investing and supporting many of the technology companies with their funding for the re-digitalization of the world.
0:18:08 Let’s spend a few minutes on digitalization before we move on in the sense of there’s vast data centers being created today.
0:18:20 I would love to hear your thinking on whether that investment is going to be where winners are accrued or re-overinvesting as we typically do in booms and busts.
0:18:27 And then walk me through sort of like how you see winners emerging in this from end to end, right?
0:18:32 You generate energy, you lease data centers, you – walk me through how you see that.
0:18:38 So there’s no straight line in investing to success.
0:18:43 And usually at points in time, people will lose money because they get overexcited.
0:18:51 But there’s – we’re in a period of time where this is a major, major build out of what’s going on.
0:19:00 The clear winners in this AI revolution are going to be the major technology companies.
0:19:01 That’s sort of easy.
0:19:03 They’re very sophisticated.
0:19:05 They have large balance sheets and capital to deploy.
0:19:12 They’ve already developed models and they’re going to be very, very – they’re going to win.
0:19:13 They’re going to win.
0:19:14 And they have the data.
0:19:15 And they have enormous amounts of data.
0:19:18 So all of – they’re going to win.
0:19:19 That’s easy.
0:19:28 Like I’m not sure there’s anything that I would – that’s helpful to anyone listening to this if I tell you, oh, you should buy Google.
0:19:32 These are going to be great companies and they’re going to continue to be great.
0:19:45 The winners that are unknown today are the companies that are going to figure out how to apply artificial intelligence into their businesses and make them better.
0:19:53 And there are many businesses today where you cannot get people to operate the businesses.
0:19:55 There just aren’t enough people.
0:20:12 And if you can, therefore, deploy robotics into businesses and shrink the amount of labor you need or there are plants that are being operated in Asia that had high dollar value.
0:20:13 That’s why they went there.
0:20:16 But the reason – high dollar value products.
0:20:18 But they went there because there was high labor component.
0:20:28 If you can shrink the labor component, many of those plants can come back to where the demand is, specifically, I’d say, the United States.
0:20:41 So, the unknown winners are going to be the companies that can apply artificial intelligence into their businesses and make them more efficient and more profitable.
0:20:45 And I think those that do it will win.
0:20:46 Those that don’t, some will fall behind.
0:20:53 But the productivity advances we see over the next 20 years probably will be unprecedented for a period of time.
0:20:59 Certainly, we haven’t seen it for a long time in business across America.
0:21:06 Is there anybody you’re tracking externally that you would never acquire, that you admire how they’re applying sort of technology?
0:21:09 You know, we’re in the early, early stages of this.
0:21:12 And so, we’re trying to learn from everybody.
0:21:14 We’re talking to many.
0:21:22 We, of course, given our scale, we have access to very significant resources and we can talk to most people.
0:21:24 So, we talk to all the technology greats.
0:21:27 We deal with all of them fundamentally in our business.
0:21:35 In addition to that, we’re continuing to learn and apply these technologies within our business.
0:21:54 And what I can tell you is the early learnings of our business, some of our industrial businesses are, and why I say the things I just said to you, is that the early learnings are that the advancement of productivity is very, very significant.
0:21:57 And you see that in your battery.
0:21:59 Like, you guys make half the batteries in the world, don’t you?
0:22:04 Look, we make just under half of the car batteries.
0:22:04 Yeah.
0:22:10 I mean, we make the little car battery that starts your car, you know, when you get up in the morning, it doesn’t start, and you have to go get a new one.
0:22:11 So, that normally-
0:22:12 Happens all the time.
0:22:13 Half of those-
0:22:13 In winter.
0:22:15 Half of those will come from us.
0:22:15 Yeah.
0:22:17 That are out there.
0:22:20 And it’s an amazing business.
0:22:25 And we continue to re-you know, we’re always trying to optimize businesses.
0:22:39 Our job is to invest in businesses and make them better so that they will grow greater amounts of cash flow so we can continue to invest in the businesses and provide dividends to our owners.
0:22:55 And so, as we try to make these better, we’re applying artificial intelligence into all our businesses, including that battery business, which is, and why it’s a perfect one for these type of applications is we have 25,000 people in 20 plants.
0:23:03 We do very repetitive process, and as a result, and we have $9 billion of costs within the business.
0:23:13 If you can improve those by 30%, that’s a lot of money to the bottom line, and it can be very significant for the company.
0:23:18 Is there another example that stands out about how you’re applying AI to the businesses that you control?
0:23:31 You know, every single business we have, we have a healthcare business where we have, we approve your healthcare in the United States.
0:23:41 If you need a back surgery and you need authorization from your insurance company to do it, we take the phone call from you, and we approve it online.
0:23:49 We approve your $150,000 operation or not, and our agents do that.
0:23:57 And today, the amount of information we can put up when you call in is incredible, even from two years ago is incredible.
0:24:06 And that just helps us make better decisions quicker and serve our clients who are the healthcare companies better.
0:24:08 And, but it’s everywhere.
0:24:19 You know, the putting, we’re, you know, we’re applying these type of things in all the businesses, but we’re in the, we’re in the first inning of this.
0:24:26 So it’s, um, anybody that has started should start, uh, be, and it’s not too late.
0:24:29 We’re in the early innings of the application of this.
0:24:31 It’s exciting to see where it’s going.
0:24:33 So we have a trend of digitalization.
0:24:35 What other big trends do you see?
0:24:42 The second one is that there is a transition of the world to low carbon energy.
0:24:49 And, uh, and I say it that way because what, what’s really important here is we just have less carbon out there.
0:25:06 And, and, but what’s, what’s even more important today is that solar and wind, which is where we’re, um, which is what’s filling the gap, are the lowest cost energy sources for power in the world, in most countries today.
0:25:16 And why that’s really important is it doesn’t matter whether you choose to have less carbon or no, don’t care about less carbon.
0:25:19 What you do choose is to pay less for your power.
0:25:24 And, uh, and that, that, that’s the, the simple economics are today.
0:25:28 If you go to somebody and say, do you want to pay more for your power?
0:25:32 They will say, they will say, no, I don’t want to pay more for the power.
0:25:33 I’d rather pay less.
0:25:38 And, and as a result of it, the lowest cost power in most countries of the world is solar and wind.
0:25:40 Therefore, you’re going to choose solar and wind.
0:25:45 So it’s inexorable that we’re going to build out most, more solar and wind in the world.
0:25:52 Um, in the United States today, there’s no doubt we’re drilling more oil, which is, remember, oil is not used in power.
0:25:58 Oil is used for basically cars, chemicals, and, um, planes.
0:26:04 They, it goes into jet engine fuel, goes into car engine fuel, and it goes into chemicals.
0:26:06 And that has nothing to do with power.
0:26:08 Uh, oil is not used for power.
0:26:14 Natural gas is, and a natural gas is one of the great assets the United States has.
0:26:17 Um, it’s going to export it for a long time.
0:26:19 It’s going to use a lot of it in America.
0:26:24 Eventually batteries and nuclear will be the base load and it won’t be natural gas,
0:26:29 but it’s being shipped elsewhere in the world.
0:26:36 And where it’s going to is needed for base load because they, they, um, they, they need that,
0:26:43 that base load power or it’s replacing coal, which is hugely beneficial to the world.
0:26:52 So, natural gas is an incredibly important bridge fuel in America and long-term fuel in many other places in the world.
0:26:59 So, the LNG market, uh, in the United States is extremely important and very lucrative for a long period of time.
0:27:01 So, let me make sure I understand this.
0:27:09 So, wind and solar, low cost, and then gas is sort of the base load when there’s no wind or solar because we don’t yet have the batteries to time shift?
0:27:16 Well, you know, we have, we have base load capacity in the U.S., which is nuclear, um, that will continue to grow.
0:27:19 We can talk about nuclear if we have time later.
0:27:28 Um, what’s happening, uh, in, in grids is that you need something to stabilize the grids and to store when,
0:27:38 because remember, solar, the sun only shines during the day, it’s usually dark at night, and wind actually, usually only blows at night.
0:27:50 But you normally don’t have, the, the, um, incidents of both together are not always the case, and you have to have something to bridge one of those.
0:28:11 And, uh, increasingly, in past, nuclear’s done that, and gas has done that, increasingly battery storage, uh, at scale, distributed, will help both with trends, transmission bottlenecks, but also with the, um, the two offsetting, uh, amounts.
0:28:16 How do you see the trend with, like, data centers in terms of electrical use?
0:28:21 Do you see that continuing to be, because these take a long time to permit, to get into place?
0:28:24 Or do you see that reducing, uh, in time?
0:28:34 So, so the reason why, uh, one of your questions earlier, which I really didn’t answer, was, um, our data centers, are we, like, are we going to get in trouble with the amount of money that’s going into data centers?
0:28:41 And the answer is no, and it’s largely because it takes a long time to permit a data center.
0:28:42 Mm-hmm.
0:28:53 You need to find power to power the data center, and the needs of the technology companies are very significant, and on top of that, energy usage everywhere is going up.
0:29:08 And as a result of that, it just takes time to bring sites on, and most sites today that are available to be built are already contracted to somebody for the next 20 years.
0:29:29 So, um, we’re in a, we’re at a, a point in time where it’s, it’s, we’re now trying to entitle new sites, and we’re, because of our vast real estate business, our vast power business, our vast data center business, we’re as skilled and as, um, integrated as they are to entitle new sites.
0:29:50 But it takes time, and, um, we’ve got some really exciting large sites coming, but these most, the earliest big one that’s going to come on that’s brand new that we’re entitling will, and even though it has enormous advantages because of, it already has power, it’ll be years away.
0:29:56 And so, you’re, like, all your risk is, you’re de-risked because you’re not doing it unless it’s contracted out, is that?
0:29:58 Generally, yes.
0:30:13 We’re not, uh, we don’t, we’ve, we’ve, in the past, we never have, and, uh, I don’t think we, um, we need to take risk on that, and therefore it’s like, when we build an office building, you know, you’re, you, you let it to a bunch of tenants, then you build it for them.
0:30:19 And, uh, you don’t have to take the risk on that, in particular in these, because of the, um, demand for it.
0:30:22 And what’s the third trend that you see?
0:30:38 So, so the, the third trend that we, um, identified a long time ago, and I’d say it’s, uh, changed even more, but is more relevant today than ever, which is just the de-globalization of industry.
0:30:46 And I, or I’d call it the re-industrialization of countries because of what’s going on in the world.
0:30:48 And, uh, that started with COVID.
0:31:08 It started with, um, uh, the Asia West issues, which, as you can imagine, that one has only, um, the, the, uh, since we coined that four years ago, five years ago, it’s only increased given what’s been going on.
0:31:22 Um, but increasingly many companies are moving, uh, industrial capacity back to Western markets where on balance they can, um, make sense of putting plants there.
0:31:28 And part of it’s for supply chain, pharmaceuticals, uh, need, now need to be next.
0:31:38 Some of it needs to be next to customer, um, because they get caught during COVID that all of a sudden all my manufacturing’s in China.
0:31:39 How do I get it here?
0:31:41 It can’t get out of China.
0:31:59 So increasingly those type of things, um, but, but also with tariffs and with other things, um, you’re going to, uh, relocate manufacturing capacity back to, to other markets and, and be low, more local.
0:32:15 Um, and, um, what I would say is things, many things went to Asia and a lot of them will stay there and the Asian markets will be fine with this because they’ve, they’ve now matured to the point where they are service economies in themselves.
0:32:29 But, um, many products that have been developed there will move back to America because the labor components with robotics coming in are becoming less and less and less.
0:32:36 So the reason for them to be in Asia is, um, less there today than it’s ever been.
0:32:47 And on top of that, if there happens to be a tariff long, if there is a tariff longer term, then, um, then it’s even going to quicken that process up.
0:32:57 What do you see as the second order, either opportunities or challenges to that sort of call it repatriation of manufacturing?
0:33:01 Look, I think China, it’s a, it’s an economy in itself today.
0:33:03 It’s 1.5 billion people.
0:33:05 They’re getting richer every day.
0:33:08 They’re turning into a consumer service society.
0:33:11 There’s not that much of manufacturing that’s relevant to them.
0:33:17 I think they will, they will do extremely well as a country, uh, on their own.
0:33:29 But there are some countries in the world where they haven’t yet transformed themselves to be service economies and they’re reliant on jobs that were from outsourced manufacturing.
0:33:37 And if you can do that closer to consumer, those, um, countries may have some issues.
0:33:43 On balance for Western countries, I’ll just take the U.S.
0:33:50 As an example, you’re bringing some jobs back, maybe not as many as left before to make the product.
0:33:52 But if that product comes back, you’ve actually added jobs.
0:34:06 And, uh, and that’s very positive, which sort of leads to the long-term story of America, which is the long-term story of America is extremely strong because, um, the U.S.
0:34:18 today has, uh, energy, capital, and technology dominance, energy, capital, and technology dominance.
0:34:22 There’s nobody in the world that has a technology businesses that the U.S. has.
0:34:26 There’s nothing in the world that has the capital markets the U.S. has.
0:34:42 And, um, the U.S. just by nature has dominance, nature and some hard work has dominance in oil, in gas, in solar, and in wind, and it has dominance in nuclear.
0:34:49 And those five things together give it energy dominance in the world for a long, long period of time.
0:35:07 And, um, so I think those three, those three things are going to make, on top of one of the greatest GDPs in the world, an entrepreneurial class, manufacturing moving back, at least to some extent, a lot or to some extent.
0:35:10 On balance, it’s going to be positive for, for growth.
0:35:15 Um, the U.S. has a pretty good runway going forward.
0:35:26 It sounds like you think we’re at an inflection point for productivity and some of the, the job losses will be offset by sort of the remanufacturing, uh, coming back to the U.S.
0:35:32 How, how do you, where do you think we are in that, like that game, I guess?
0:35:35 There is no straight line in anything.
0:35:39 Everyone always thinks that, uh, somebody says something and it’s going to happen tomorrow morning.
0:35:48 Usually, usually it happens, uh, in greater amounts, but it takes longer periods of time and takes slower than you think it would happen.
0:35:52 Um, I, I would say we’re in the early stages of all of this.
0:35:56 Uh, we’re seeing, going to see productivity advances and nobody just flips a switch.
0:35:59 Thing is, nobody ever flips a switch.
0:36:03 These are incremental changes over very long periods of time.
0:36:23 But it’s, what it means is that, is that the application of greater intelligence into businesses is going to, um, make business better, more efficient, more productive, and, um, and better, better, better for the world, frankly.
0:36:27 Um, that, that, that just makes us all, uh, smarter.
0:36:28 You mentioned real estate.
0:36:33 How has that changed over the past, I would say 10, but specifically five years?
0:36:43 You know, again, I would say, uh, over the past, uh, 25, 30 years, 10 years, five years, um, these things always just evolve.
0:36:56 And, uh, you know, industrial capacity used to be just used for manufacturing, storage of goods, and today it’s used for transportation of many goods that are delivered to homes.
0:37:02 So industrial has changed, enormously changed as a business over the past 10 years.
0:37:10 Retail has changed because people used to do all their shopping, uh, uh, in stores.
0:37:17 Today, what they do is they do very bespoke shopping in stores and they want experiences in stores.
0:37:21 But if you want to buy paper towels, you usually don’t go to the mall.
0:37:23 You just order it online.
0:37:32 And, um, but, but if you want to have a meal and you want to go and try on a shirt or pair of pants or have some fun for the afternoon, you go to the mall.
0:37:41 And that’s, that’s what’s changed is that commodity goods, if you own commodity, if you want almost today commodity anything, it’s bad.
0:37:43 If you own commodity office, bad.
0:37:45 If you own commodity retail, bad.
0:37:47 If you own commodity industrial, bad.
0:37:49 In fact, if you own commodity hotels, bad.
0:37:58 Um, if you, what’s great today is all of those things in the top 25%.
0:38:05 And our, our view always has been buy the best, uh, own the best, buy the best, continue to reinvest into the best.
0:38:07 And so our real estate is among the best in the world.
0:38:14 Um, and we continue to, um, experience some, some great numbers.
0:38:26 Uh, look over the last five years because of COVID and because other things, and because interest rates went up by 400, 500 base points, um, all of that disrupted the real estate market.
0:38:31 But the, the worst is, uh, behind us by far.
0:38:37 We’re looking in the real view mirror by, by, um, uh, what happened in real estate.
0:38:43 And in fact, this time the fundamentals are actually pretty good in most things.
0:38:52 Um, it’s just, there are some people that have, uh, capital structures that aren’t built for these financing markets.
0:38:59 Uh, and therefore they have to put capital in to be able to deleverage or whatever they have to do or, or somebody else will take over the asset.
0:39:05 Um, but that’s not a, a huge issue across the world.
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0:41:09 Maybe spend a few minutes and sort of like take me behind the scenes in how you think about risk and how you think about interest rates and how you think about debt when it comes to assets.
0:41:19 Our fundamental thesis of investing is that you should put a prudent amount of debt on assets that can withstand markets.
0:41:24 If you can, then you should fix it because you know your cost.
0:41:33 And from time to time, if you got it wrong, you put a little more, make sure you have a little more money around to put it in and support your asset.
0:41:39 So, we’ve always conservatively financed our businesses and assets.
0:41:45 All of our financing is asset by asset by asset by asset or business by business by business by business.
0:41:54 So, any debt that we accumulate onto our consolidated balance sheet is just the accumulation of a whole bunch of single asset financings.
0:42:04 And it’s not that we ever want to or think that we will give back assets or not live up.
0:42:13 In fact, our reputation is with our lenders is that we’re one of the best sponsors in the world to borrow, lend money to because we support our businesses.
0:42:21 But buying, having asset by asset by asset by asset financing allows you to just deal with the situation one by one by one.
0:42:27 And its duration, I mean, they’re spread over long, long periods of time.
0:42:36 And with interest rates, I think the most important thing to remember is we don’t borrow the treasury rate.
0:42:38 Only the government borrows at treasury rates.
0:42:44 And what we borrow at is treasury rate plus spread.
0:42:44 Yeah.
0:42:53 And historically, spreads were 200 basis points and interest rates were 300 basis points and therefore you borrow it at five.
0:42:58 And when COVID hit, interest rate, the treasury rate went to zero.
0:42:59 Yeah.
0:43:06 And what the borrower, most of the lenders said to us is, meh, I’m not going to lend you at 200 over and give you three.
0:43:10 I’m widening that out to 350.
0:43:15 So I’ll give you five or four and a half.
0:43:21 And therefore, before we were borrowing at five and in COVID, we were borrowing at four and a half.
0:43:25 So when people say, oh, geez, you got all this financing in COVID.
0:43:36 Yes, maybe some people did and some people got very low rates because rates were zero and they might have borrowed at two at an extreme point in time,
0:43:37 but not very much.
0:43:40 And most of it, lenders just widened the spread out.
0:43:43 Today, base rates are high.
0:43:44 We’re back to five.
0:43:45 Guess what?
0:43:49 Spreads are the lowest they’ve ever been in history.
0:43:55 We just did a 30-year Brookfield Corporation financing.
0:44:02 So we’re borrowing money for 30 years fixed for that time period and is 125 over.
0:44:10 So spreads, basically all in coupons are important.
0:44:20 And that’s really important to remember about investing in real assets, real estate, but also infrastructure, renewables, et cetera.
0:44:25 What distortions do you see by sort of like historically low interest rates?
0:44:27 And even by today’s standards, you mentioned they went up.
0:44:32 They have gone up quite a bit, but historically, they’re still well below average.
0:44:33 Yeah.
0:44:43 Look, I think that maybe is the most important point to note here is that interest rates aren’t that high.
0:44:48 They’re higher than they were because interest rates went to zero.
0:44:52 And for a number of years after the financial crisis, they were close to zero.
0:44:57 And now they’re actually in a relatively normal range.
0:45:04 I’m sure we’re going to see another 50, 100 base points off of the short rates.
0:45:10 And we’re going to settle into just a regular range of rates.
0:45:19 But these rates are actually pretty normal and for our business, very constructive.
0:45:25 And the things that we can do and we’re refinancing it because the coupons aren’t that much different than what they were before.
0:45:42 People, we talked about sort of dislocations providing opportunities and, you know, maybe spend a few minutes walking me through how you think of positioning to manage the recycle, but not only maintain your assets, but also take advantage of dislocations in the market.
0:45:52 So the first thing one has to do when there are dislocations in the market is make sure that you were prepared for it.
0:45:59 So the one thing you should do always when times are really good is ensure that you’re preparing for the down markets that’s coming.
0:46:06 The ones that don’t usually aren’t successful in the fullness of time.
0:46:13 But if you are prepared, the first order of business is let’s double down and make sure that we’re fully prepared.
0:46:25 But then secondly, and I’d say coming out of recessions or cycles, coming out of the bottom, what’s most important is just have everything you have intact.
0:46:27 Do not lose anything.
0:46:33 Do not lose too much and keep going because there’ll be many people who will have lost stuff.
0:46:43 What’s even better to enhance the business is at that point in time as the market’s starting to recover.
0:46:56 And once you’re comfortable, we’ve taken care of all the things within our business that you can then invest capital into new businesses at that point in time.
0:47:08 That’s the difference between the great winners and long-term investing and those that are just in the middle.
0:47:12 You have almost, well, you have over a trillion dollars in management now.
0:47:17 How do you fend off the pressure to deploy that money?
0:47:20 It sounds like a lot of money.
0:47:22 It is a lot of money.
0:47:23 It sounds like a lot of money.
0:47:25 It’s a trillion dollars.
0:47:28 But it’s not that much when you do what we do.
0:47:36 A couple of years ago, we bought Deutsche Telekom, half a Deutsche Telekom, telecom tower business in Germany and Austria.
0:47:38 It’s a $20 billion transaction.
0:47:42 We’re building for Microsoft $13 billion of power plants.
0:47:50 We’re building with Intel a $32 billion fabrication plant in Arizona.
0:47:52 You know, I can go through the list.
0:48:00 These are large transactions that consume significant amounts of capital that earn excellent long-term returns.
0:48:09 And I’ve just used that to say we’ve been doing this a long time.
0:48:24 What we promise our investors and our clients is that we will take moderate amounts of risk, not no risk, but moderate amounts of risk, and earn good returns over long periods of time.
0:48:26 We won’t shoot the lights out.
0:48:29 You’re not going to get 45% returns every year.
0:48:32 And we’re not trying for that.
0:48:38 But average returns over an above average period of time equal outstanding returns.
0:48:39 And that’s the point.
0:48:46 The point is, our parent companies earn 19% annualized returns for 30 years.
0:48:52 When you compound up, which doesn’t sound like very much, 19% returns annualized for 30 years.
0:48:56 Like, just when you say that in that line, it doesn’t sound like that much.
0:49:03 But I think that’s a million dollars became almost $200 million over that period of time, or $1,000 became $200,000.
0:49:04 It’s a lot.
0:49:14 And so the point is, success in investing isn’t about making a lot of money in a short period of time.
0:49:21 What it’s really about is earning reasonable returns over very long periods of time.
0:49:23 And look, that’s Berkshire Hathaway.
0:49:34 Berkshire Hathaway is successful because they have been able to deploy capital at reasonable rounds of turn over very long periods of time.
0:49:39 And that’s the success of long-term investing.
0:49:41 Is that a company you look up to?
0:49:46 Look, they’ve done an incredible job in their business over a very long period of time.
0:49:48 Maybe you mentioned over 30 years.
0:49:53 Walk me through a little bit of the history of Brookfield and then the future, where we’re going.
0:49:56 So we started as an operating business.
0:49:59 We just invested for ourselves.
0:50:05 We had the businesses that we basically have today.
0:50:14 Infrastructure, real estate, renewables, and industrial service, we call private equity today, businesses, and credit lending.
0:50:15 Those were our five businesses.
0:50:17 We did it for ourselves and we lent money.
0:50:39 And 25 years ago, we decided that we could take those skills we had and turn them into a business to be able to manage some of our money and some of our institutional or other clients’ money and offer alternatives into those funds.
0:50:45 When it started, nobody wanted to invest with us because they didn’t really understand alternatives.
0:50:49 And today, that’s turned into a trillion-dollar business.
0:51:02 It’s been extremely successful, largely because these products are ideal for institutional and retail clients to invest into.
0:51:11 And the past 25 years has been about institutional and this comment is not meant to say that they won’t be investing.
0:51:20 But their increase from going from zero to some of them are at 30%, 40%, 50% alternatives.
0:51:24 When you go from zero to 50%, you can’t go to 100%.
0:51:27 So, a lot of them are at their numbers.
0:51:36 But what’s happening today and to your question of the future is that the same phenomena is now happening in retail.
0:51:38 Retail being individuals.
0:51:41 401ks in the U.S. are going to open up to alternatives.
0:51:45 I think plans around the world will open up to alternatives.
0:51:50 Alternatives are ideal products for retail as well.
0:51:56 In fact, they’re almost more ideal because you’re saving for your retirement.
0:52:06 And what better to have in there than a product that earns a reasonable return over a very long period of time and can compound.
0:52:21 And so, the future of our asset management business is really about that, the opening up of retail and continued growth of retail wealth with our products.
0:52:27 Doing the same things that we do for institutions, exact same.
0:52:34 But now, just opening up in different types of products that are suited or tailored for individuals.
0:52:36 What does that mean?
0:52:40 Maybe walk me through it because, you know, I’ve always thought you’ve had these available to people.
0:52:43 I could go buy Brookfield Infrastructure on the public market.
0:52:47 You can buy it in the public market that fits in a stock portfolio.
0:52:55 But to date, we haven’t offered you a product for your 401k in the private market.
0:52:56 Okay.
0:53:05 That was open to you to say, do you want to buy infrastructure with us and just own a bunch of data centers and different things like that?
0:53:22 We happen to have a couple of listed ones that are very unique, but what people want is private assets within their portfolios, and that’s going to increase, I’d say, exponentially over the next 20 years.
0:53:27 So, retail is sort of the future, but another big area that you’re investing in is insurance.
0:53:32 Maybe walk me through some of the opportunities you see over the next 20 or 30 years in insurance.
0:53:44 Yeah, so outside of our asset management business, we decided to take a portion of our capital and put it into insurance five years ago.
0:53:57 It was a fortuitous time because we bought some excellent insurance companies at a point in time where they weren’t doing very well because interest rates were extremely low and they weren’t earning very high returns on their capital.
0:54:01 Fast forward four years later, the companies are doing extremely well.
0:54:05 We’re making $2 billion a year of cash flow within the business.
0:54:11 And insurance for us is, I’d say the following.
0:54:19 Firstly, and maybe just to go back, our goal was get in the insurance business, not because we wanted to be in insurance.
0:54:31 What our goal is, is our clients come to us because they want our investment skills.
0:54:40 What we have is a very unique offering, is a bunch of investment skills that can create products for long-term investors.
0:54:52 Our insurance company now, being $120 billion of assets, is a perfect long-term investor into all of the things we do for our asset management business.
0:55:14 We have a special expertise to be able to offer because we have greater access or greater comfort with all the investment products to be able to put into the insurance companies than most other groups out there.
0:55:18 Maybe there’s a few others like us, but not very many.
0:55:21 And therefore, we have a special benefit for that.
0:55:26 So, we’ve chosen annuities in the United States largely.
0:55:29 So far, we’ve now just got licensed in the United Kingdom.
0:55:32 Why annuities?
0:55:33 What appeals to you about that?
0:55:36 It’s just because they’re low-risk liabilities.
0:55:40 We’re not taking on high risk on the liability side.
0:55:46 Our goal originally in getting into this was don’t take risk on the liabilities, earn our money on the asset side.
0:55:53 And we have this unique ability to earn excess returns on the asset side.
0:56:10 And our goal was put very significant amounts of capital and overcapitalize the businesses, which allows us to do things on the asset side of the balance sheet, which is very different than many insurance companies.
0:56:11 Like what?
0:56:14 You know, we can own real estate to a greater extent.
0:56:16 We can own alternatives to a greater extent.
0:56:18 We can own infrastructure to a greater extent.
0:56:24 We can own high-yield bonds as opposed to just fixed income on the market.
0:56:29 All the things that we do for our clients, we can put them in the insurance company.
0:56:34 And they may take more capital, but we’ve overcapitalized the company.
0:56:36 So, we started with $4 billion.
0:56:44 We’ve increased the capital, I think, to $16, $17 billion of book equity within the business.
0:56:46 We continue to overcapitalize.
0:56:57 But on top of that, we have another $150 billion of capital up top that if we need more money, we’ll put it into the insurance companies to ensure they’re healthy and better than any that are out there.
0:57:08 And we have an excellent relationship with the regulators and explain all these things to them and are very transparent with all the transactions we do with them.
0:57:30 And we happen to have some very unique things that we can do because, you know, for example, if we own an office building and somebody owns the other half and they want to sell and we know that’s a really cheap price they’re going to sell at, that’s a great real estate investment for our insurance company.
0:57:36 Very seldom do people have that opportunity with our knowledge and access to opportunities.
0:57:40 So, it’s a pretty unique offering.
0:57:43 And that’s what we bring to the table.
0:57:48 Do you think you’ll get out of annuity, well, stay in annuities but expand into other businesses?
0:57:57 I’m imagining short duration stuff is probably a property and casualty doesn’t lend itself to that type of investing, but maybe reinsurance or?
0:58:03 Yeah, look, I would say we wanted to start, this is a 25-year venture.
0:58:04 We’re five years in.
0:58:10 We wanted to start to make sure that we knew what we were doing.
0:58:13 We met all our regulators.
0:58:14 We earned their respect.
0:58:21 And we could operate and figure out what were all the risks.
0:58:23 We’ve been in it five years.
0:58:24 We’re very comfortable.
0:58:36 Over time, we may branch out into other types of other products that we can understand that fit our skill set.
0:58:39 And that’s really what’s important to us.
0:58:47 So, first, we’re expanding internationally writing annuities or pension risk transfer annuities, which are both are very similar.
0:59:03 So, instead of going out of our comfort zone on the type of liability, what we’re doing today is we’re expanding to the UK, which is a big pension risk transfer market.
0:59:06 And that’s just a different way to expand.
0:59:09 Are the pension risks defined benefit or defined contribution?
0:59:19 These are pension risk transfer means, which happens in the US, Canada, and the UK largely, those three places in the world.
0:59:27 What it means is that if there’s a corporation that has a defined benefit plan that wants to get it off their balance sheet.
0:59:31 So, they have a $10 billion plan.
0:59:33 There’s 10 billion assets, 10 billion liabilities.
0:59:37 They can commute that plan to us and we can, our insurance company can take it.
0:59:40 So, they’re no longer on the hook for the plan.
0:59:44 They’re no longer at risk on the assets or the liabilities.
0:59:46 We’ve assumed that risk.
0:59:48 We will now pay their pensioners.
0:59:55 And they gave us the assets to earn over time, hopefully, the amount of money to pay all their pensioners.
0:59:57 And if not, we’re on the hook for it, not them.
1:00:03 Can you spend a few minutes walking me through the machinery of Brookfield and why you’ve structured it the way you have?
1:00:05 Look, I would just say –
1:00:11 I’ll preface this with like one of the criticisms from the outside in is that it’s super complicated.
1:00:14 There’s a lot of different entities and moving parts.
1:00:15 How do you think through that?
1:00:22 So, I would just say that, yes, there are probably more pieces of Brookfield.
1:00:36 First-hand launch, I might disagree first by saying there are many companies in the world that are large like us and they have as many pieces as we do.
1:00:38 That’s the first point.
1:00:40 So, I’m not sure that’s actually a true statement.
1:00:46 But I’ll take your points at face value.
1:00:53 And I would just say each one of the pieces we’ve set up has been highly thought through and contributes a lot to the business.
1:00:57 These are not random things we’ve done.
1:01:03 They’re very specific and they contribute enormous value in the long term to the company.
1:01:12 And because of that, we have to explain them more to maybe – sometimes have to explain them more to investors.
1:01:24 But for our friends, they understand exactly why those pieces are there and what they do for us and what each accomplishes.
1:01:34 In the short term, we could wave a wand and get rid of all those, as you denote, complicated parts.
1:01:36 We could wave a wand and get rid of them all.
1:01:40 In the long term, it would be bad for shareholders.
1:01:43 Less returns would be earned.
1:01:47 We would be more at financial risk.
1:02:00 We would have – we have the maximum amount of flexibility within our structure to be able to go through, deal with opportunities, risks, and everything that’s out there.
1:02:09 So, I just – I – look, we can always do better on explaining the pieces and we try all the time.
1:02:14 And it’s incredibly – our reputation is incredibly important to us.
1:02:24 So, when people criticize us about our structure, our different things that are there, we try to double down and make sure we explain it all to people.
1:02:32 But what I – I would just say that each of those pieces is really important and contribute a lot to the business.
1:02:39 Hypothetically, if you were to all put it under one umbrella, how would that change the opportunity set available to you?
1:02:44 It would just mean dilution to some shareholder.
1:02:50 And, for example, we spun off our asset management business two years ago.
1:02:59 There’s a whole group of U.S. investors, largely, that buy asset management businesses that only want to be invested in asset management.
1:03:03 They don’t want to own assets that we own.
1:03:05 They don’t want to be invested in insurance.
1:03:07 They don’t want to do all the other things we do.
1:03:21 They don’t want to change – like our parent company, Brookfield Corporation, it has changed in 35 years in many different ways in many different times for the benefit of all of us.
1:03:27 But you need to trust us when we’re changing.
1:03:36 Brookfield Asset Management is a pure play asset management business that’s asset light that will probably never be anything different.
1:03:40 You can trust us for that and that’s what it is.
1:03:50 So, they’re just different audiences and it just allows us to have a security which is tailored to that audience.
1:04:04 And if we want to offer it to somebody in the public markets or to another alternative manager we want to merge in or something, it gives us the opportunity to do that and not have to deal with all the other issues that we have.
1:04:09 Well, what about your insurance business or what about your investments or what are you going to do next?
1:04:13 And it just allows us to do that.
1:04:16 So, I don’t – we could do it.
1:04:20 It just would take away a lot of the great benefits we have in the organization.
1:04:28 If you put your investor Bruce hat on, which of the businesses do you think is the best positioned for the next 15 years?
1:04:29 And I’m not asking returns.
1:04:33 I just mean which business do you think is the best competitively positioned?
1:04:35 I just think they’re all different.
1:04:37 They’re all totally different.
1:04:44 Everything we invest into has enormous opportunity going forward as long as we execute properly.
1:04:47 But they’re – each one of them is different.
1:04:50 I get excited.
1:05:00 I could get excited about having all of my net worth in every single one of them and they’re all pretty exciting going forward.
1:05:03 Maybe spend a few minutes on talent and people.
1:05:10 Brookfield is known to take really big bets with what from the outside looking in would be young people.
1:05:14 What do you see in people that gives you the confidence to take bets in them?
1:05:20 How do you build a culture where meritocracy rises and people can take big bets?
1:05:26 So we’ve always had the view that – well, firstly, we’re an extreme meritocracy.
1:05:28 This is a partnership.
1:05:30 It’s a partnership of individuals.
1:05:39 When we leave the partnership, our shares that if you’re an owner or controller of the partnership, they go away.
1:05:41 They go on to somebody else.
1:05:47 So nobody’s family will ever be part of this partnership.
1:05:48 It’s a meritocracy.
1:06:10 Second, we’ve always had the view that a cross between wise, older people and smart, aggressive, young people both give you the gravitas to deal with situations which you need a little history.
1:06:18 But also allow you to be – allow you to know more about what’s going on today.
1:06:26 I’m positive our 30-year-olds today in the business know more about technology than I do because they’ve grown up with it differently.
1:06:38 It allows us to be faster, better, quicker to every new trend in the world and what’s going on out there.
1:06:47 And it also, I’d say, creates a culture where people want to be here and get ahead because they know they can.
1:07:04 And so I – look, we brought to the partners and to our senior people three years ago, we brought Connor Teske forward as the next person that will be the CEO of the asset management business.
1:07:10 That was internally vetted.
1:07:20 It was then externally vetted and today we’re in the process of him continuing to meet clients and investors and all those kind of things.
1:07:23 And I think he’s 37 years old today.
1:07:31 He’s incredibly passionate, talented, and he’ll bring through a whole new group of people within the company.
1:07:38 And re-energizing businesses is what makes them better and different.
1:07:42 Walk me through some of those meetings where you’re making a big investment decision.
1:07:43 What goes on behind the scenes?
1:07:45 How do you quantify risk?
1:07:46 Where do you spend your time on deals?
1:07:53 Our investment process is we only invest in things that we deal with and know.
1:07:58 We have people on the ground and our knowledge of the business.
1:08:07 And we’re – our investment committees are normally only focused on downside protection.
1:08:10 Upside will always take care of itself.
1:08:17 And whether you shoot for 16%, 22%, 29%, 18%, none of those matter.
1:08:19 They’re all great.
1:08:23 What’s really important is what are the risks?
1:08:25 What can go wrong?
1:08:27 How bad could it get?
1:08:31 And how do we deal with it if that happens?
1:08:39 And so we spend virtually all of our time on downside protection at our investment committees and that’s all that’s important to us.
1:08:41 When you’re wrong, where are you typically wrong?
1:08:44 And you haven’t been wrong a lot.
1:08:44 No, no.
1:08:45 Look, we make mistakes.
1:08:47 We try to make small mistakes.
1:08:48 I’d say that’s it.
1:08:51 When we’re wrong, where are we wrong?
1:09:15 We’re wrong in increment – in small ways which aren’t – you don’t know about them very much because in the last 35 years, we’ve been right generally on the large things and nothing has been irreparably harmful.
1:09:26 And that’s because the things we do are small, incremental, and when we make mistakes, we make them along the way.
1:09:37 And we encourage people to keep learning and growing because if you don’t make some mistakes, you never advance, but do not make big mistakes.
1:09:42 And I’d say that’s the biggest thing we try to impress across the organization.
1:09:44 You mentioned the investment committee.
1:09:52 I just wonder, behind the scenes, are investment decisions signed off by one person or is it a committee that signs off?
1:09:56 And if it’s a committee, how do you hold people accountable or responsible for those?
1:10:08 So our – usually what happens is some transaction came into the company some way or we had an idea and we don’t talk to somebody and a transaction came about.
1:10:13 It’s then approved by – it’s approved by today because we have these vast businesses.
1:10:25 It’s approved in the business, but then we have one committee that – it’s almost like an allocation committee up top because we want to know how many – across the organization, we want to know how many transactions are happening at any one point in time.
1:10:29 So we’re not compromising, like you said, how could you make a mistake?
1:10:37 If everybody made a massive transaction at the same point in time, what we’re probably betting on is a cycle.
1:10:40 And you may not want that.
1:10:42 And if you do, you better knowingly do it.
1:11:00 And so in addition to all the deals being approved down below where accountability comes from, we have an oversight committee that approves everything that goes on in the organization, which includes six or eight of us.
1:11:10 And that approves everything really just to be a final governor over the entire organization.
1:11:19 Are there patterns to cycles that you notice in advance of them happening where you’re like, we’re at the first inning or we’re at the late stages?
1:11:21 What are the signs that you look for?
1:11:33 I would just say that cycles are never the same, but they sort of rhyme and they look similar.
1:11:41 So the one thing of having wise older guys around, I’ll consider myself that today.
1:11:47 I used to be a young, unwise individual.
1:11:49 I’ll try to consider myself.
1:11:51 I know I’m old, just not sure I’m wise.
1:12:09 But some of the reason for having the wiser individual around is having the elongated knowledge of what goes on in cycles and what goes on in periods.
1:12:11 And we’ve seen this before, is helpful.
1:12:17 Sometimes it’s a hindrance, but sometimes it’s very helpful for context.
1:12:35 And therefore, that’s what makes great organizations, I think, in our view, is that you have the combination of the tenacity and passion to make investments and be successful,
1:12:53 tempered by the knowledge and skills of past and what’s gone wrong to be able to bring together risk management and drive to succeed.
1:13:07 I’m curious, like, how would you pass that on to somebody in your organization or me if you were to sort of hear the things I look for or don’t look for?
1:13:14 You know, I would say, in general, we don’t do training, quote, unquote.
1:13:20 But every day, every single person in this organization is learning.
1:13:24 And it’s a learned by osmosis process.
1:13:29 We have open plan in the place, including myself, never had an office.
1:13:33 And people talk to one another.
1:13:36 And it’s very interactive.
1:13:43 And therefore, while I started off by saying we don’t train anybody, we train them every single day.
1:13:46 And it’s just different than sending people to school.
1:13:48 Do you do, like, postmortems after an investment?
1:13:49 And what’s the key?
1:13:51 Oh, yeah, especially the bad ones.
1:13:53 What goes into those?
1:13:54 Like, walk me through that.
1:13:55 Take me behind the scenes.
1:14:04 We try to look at, look, the successful ones, you can usually identify and know what happened.
1:14:10 The unsuccessful ones are harder to identify what happened.
1:14:15 But often there are reasons why.
1:14:17 And it either comes down to execution.
1:14:20 You didn’t execute properly.
1:14:25 You had, you mistimed the market.
1:14:30 Or you just made a bad, bad, flawed investment decision.
1:14:32 And those are the worst.
1:14:33 You mistimed the market.
1:14:35 Nah, you know, it’s okay.
1:14:42 But making flawed investment decisions is really bad.
1:14:46 Is that where you’ve got the business strength wrong?
1:14:48 The competitive dynamics wrong?
1:14:49 You don’t understand?
1:14:59 I just, sometimes it’s, we’re, sometimes we’re pushing out into areas which are adjunct to what we do and we probably shouldn’t have.
1:15:00 We really didn’t know what we were doing.
1:15:03 Not often does it happen, but once in a while.
1:15:13 How much of your investment decision, you focus on the downside, but how much of it is like we’re modeling it the next five years and then we’re tracking to that model?
1:15:22 The only thing I tell you about a model that’s produced in an investment committee is it will never be exactly what happens.
1:15:34 But I’d say if you get the, we’re trying to get the trends right, is really what it is, is in investing, it’s can you get the trend right?
1:15:46 And I would say most of our investing is we’re trying to get the price right for value and therefore often we’re buying at a discount to what we think is the value of something.
1:15:53 And therefore, that’s an important thing to note.
1:15:56 How do you think about the geopolitical risk?
1:16:08 We invest in backbone infrastructure largely and even our private equity businesses are backbone infrastructure type businesses.
1:16:23 Therefore, what’s important for us is to go to good countries with good people that you can operate with the standards we operate with and that those countries respect rule of law and will over time be good places to invest.
1:16:26 We don’t really sell over borders.
1:16:40 So, in the United States, where we are, we own data centers and telecom towers and real estate and industrial facilities and all of the things that we own in the U.S.
1:16:42 and we make batteries and we, etc.
1:16:46 All of those are consumed by individuals or companies in the United States.
1:16:47 They’re not shipped.
1:16:49 We make power.
1:16:51 It’s used within state.
1:16:58 Politics don’t really matter to us.
1:16:59 You know, they do in the margin.
1:17:06 But on balance, as long as you invest in a good country, you’re going to be fine.
1:17:09 And by good, I’m assuming you mean stable, rule of law.
1:17:11 How do you think you’re good?
1:17:16 Good means for us it has to be large enough to be able to invest.
1:17:19 Like we can’t have small countries just not because they’re not good.
1:17:20 They’re not a good place to invest.
1:17:21 It’s just not meaningful to us.
1:17:36 When you have a trillion dollars things, the benefit or the drawback is that you can’t go to a little country.
1:17:39 Like we just, we can’t invest a hundred million dollars.
1:17:40 It’s not relevant to us.
1:17:43 So we need large places.
1:17:50 We’d like them to have, we need to operate with the standards that we operate globally with.
1:17:55 We need to be, we’d like to have large GDP.
1:17:56 We’d like to have it growing.
1:18:04 And we’d like to have a currency that’s relatively, it doesn’t have to grow better than everyone else.
1:18:05 It just has to stay consistent.
1:18:07 If it’s highly volatile, not good.
1:18:10 If it goes down over the long periods of time, bad.
1:18:17 So we’d, we’d rather pick countries with those, those factors.
1:18:20 And, but it all comes down to price.
1:18:28 Like some, some have all that and then you, you, you invest when you can.
1:18:30 But, but for us, we have to have people on the ground.
1:18:32 So we pick those countries very methodically.
1:18:33 We put people on the ground.
1:18:38 We invest from time to time, new investments when we find the opportunities.
1:18:41 But we don’t randomly go to countries.
1:18:43 Like this is not a random business.
1:18:44 This is hard work.
1:18:50 Therefore, we have to be in country, be able to action an opportunity when it comes.
1:18:54 And therefore, if we’re not in a country and somebody calls us with an opportunity,
1:18:57 we just say, sorry, we’re not set up to do that.
1:18:58 Can’t, no can do.
1:19:03 It seems like part of your secret sauce is not only doing that in advance, but also
1:19:08 you seem to prove the model before you take outside investors into it.
1:19:13 You know, like I would say we have a large amount of capital ourself.
1:19:15 We’ve always invested ourself.
1:19:19 We want to make mistakes with our own money first, not with others.
1:19:24 Our reputation with our clients is the only thing we have.
1:19:27 And, and that’s really important to us.
1:19:30 And, and we try to incrementally grow to prices.
1:19:35 For example, we, we have a massive platform in the United States.
1:19:37 So we started insurance in the United States.
1:19:43 Now we’re going to the UK to do the same thing we did in the United States.
1:19:47 And we just got licensed to do that.
1:19:52 But it’s, um, we now have all the experience we have from the United States.
1:19:55 We probably couldn’t have started there.
1:19:56 Right.
1:19:59 Because we just didn’t have the same presence there as we had here.
1:20:05 And we always end these interviews with the same question, which is, what is success for you?
1:20:16 Brookfield, uh, is one of the great investment, uh, management groups in the world today.
1:20:31 And 20 years from today, success is that it is, um, bigger, broader, um, more relevant to clients, uh, and continues to do exactly what it does today for everybody.
1:20:35 And earn, earn reasonable returns with, with downside risk protected.
1:20:41 And if we can do that, we’ll have felt success, uh, of all of this.
1:20:50 Thanks for listening and learning with us.
1:20:58 The Farnham Street blog is where you can learn more about my new book, clear thinking, turning ordinary moments into extraordinary results.
1:21:07 It’s a transformative guide that hands you the tools to master your fate, sharpen your decision-making and set yourself up for unparalleled success.
1:21:12 Learn more at fs.blog slash clear until next time.

0:00:05 – Your dating app profile is sort of like your billboard.
0:00:08 You are telling a story about who you are.
0:00:09 Am I ready to date?
0:00:10 Who should I date?
0:00:11 Should I keep dating this person?
0:00:12 Should we move in together?
0:00:13 Should we get married?
0:00:16 Each of these is a pivotal point in your life.
0:00:19 The thing that we think makes us unlovable
0:00:22 is often what makes somebody feel comfortable around us.
0:00:24 But if we truly feel like we’re unlovable,
0:00:26 we never open up and give somebody the chance
0:00:28 to see that for themselves.
0:00:29 The sooner you learn how to date,
0:00:31 the sooner you can stop dating,
0:00:34 it’s not about gathering information,
0:00:36 it’s about having an experience with them.
0:00:39 Imagine that you spend 50 years with someone.
0:00:44 The day that you meet is .0055% of your total time with them.
0:00:47 You have to shoot your shot.
0:00:49 You have to approach people in public.
0:00:51 You have to take a risk.
0:01:05 You have to approach people in public.
0:01:07 Welcome to The Knowledge Project.
0:01:09 I’m your host, Shane Parrish.
0:01:11 If you want to take your learning to the next level,
0:01:15 consider joining our membership program at fs.blog/membership.
0:01:20 As a member, you’ll get my personal reflections at the end of every episode.
0:01:29 Early access to episodes, no ads including this, exclusive content, hand edited transcripts, and so much more.
0:01:31 Check out the link in the show notes for more.
0:01:39 Today’s episode is all about rethinking modern relationships from first dates to breakups and everything in between.
0:01:46 My guest is Logan Urie, a behavioral scientist, dating coach, and the director of relationship science at Hinge.
0:01:54 She’s the best-selling author of How Not to Die Alone and a leading expert in how we form, maintain, and end relationships.
0:02:01 Logan challenges some of our biggest myths about dating, including the idea that you need to wait for the spark.
0:02:10 Instead, she shares what really matters in a long-term partner, someone you’re genuinely interested in, who makes you feel good, and who brings out the best in you.
0:02:21 We cover how to approach dating apps and first dates with the right mindset, why clear communication is everything, and how to navigate a difficult conversation in love and beyond.
0:02:25 I’ve got to be honest, I feel a bit vulnerable putting this conversation out there.
0:02:34 I share more about my personal life and mindset than I have before, but I’m hoping someone out there can relate and feel less alone in their journey to find a partner.
0:02:44 So whether you’re looking for that partner, trying to strengthen your relationship, or just hoping to better connect with the people in your life, this conversation is filled with insights to help get you there.
0:02:47 It’s time to listen and learn.
0:02:54 I want to start at the beginning, which would be a first date.
0:02:54 Great.
0:03:02 You’ve reframed this from, I want to find my soulmate, to do I want to spend more time with this person?
0:03:03 Walk me through that.
0:03:07 A lot of people on a first date put so much pressure on themselves.
0:03:10 They’re really thinking about, could I spend the rest of my life with this person?
0:03:11 I’m really busy.
0:03:13 Would I want to see them again?
0:03:18 I’m going to treat this like a job interview where I ask them, what’s your five-year plan?
0:03:19 And what did you study in college?
0:03:23 And really interviewing this person for the role of spouse.
0:03:27 And then, of course, people don’t feel any spark or any excitement.
0:03:35 And so I like to take the pressure off of a first date and say, this is really an opportunity to have an experience with somebody else, to have some fun.
0:03:38 And then if you have a good time, you can see them again.
0:03:43 And you don’t have to overthink it and think, is this person who I want to spend the rest of my life with?
0:03:47 So I’ve been guilty of this in terms of the spark.
0:03:52 You know, you walk away from a first date and you’re like, yeah, they’re a nice person, but maybe they’re boring.
0:03:56 Or you didn’t feel that instant romantic connection.
0:03:58 And what do you think about the spark?
0:04:00 I mean, we all look for the spark.
0:04:02 Yeah, so the spark is very exciting.
0:04:06 Who doesn’t want to have that feeling of fireworks and instant chemistry with someone?
0:04:11 But through the work I’ve done, I’ve actually come to see the spark as a bit of my nemesis.
0:04:16 Because I have coaching clients who say to me, Logan, I went out with this guy.
0:04:17 He was great.
0:04:18 We had a good time.
0:04:20 Oh, I’m not going to see him again.
0:04:22 Like, what are you talking about?
0:04:24 And they say, I just didn’t feel the spark.
0:04:32 And so in our culture, people have come to expect that if you don’t have that instant feeling, then it must not be your person.
0:04:37 And instead, I teach my coaching clients about the three myths of the spark.
0:04:42 So the first myth is that if you don’t have the spark, then it can’t grow.
0:04:43 And that’s absolutely not true.
0:04:47 So we know from research that only 11% of people feel love at first sight.
0:04:52 And that means many people are getting to know someone over time.
0:04:53 Maybe they live in the same apartment building.
0:04:55 They work in the same place.
0:04:58 And that attraction and appreciation grows over time.
0:04:59 So the spark can definitely grow.
0:05:04 The second myth is that if you feel the spark, it’s definitely a good thing.
0:05:10 And actually, sometimes certain people give us the spark because we actually don’t know how they feel about us.
0:05:14 So sort of that hot, cold feeling makes us wonder, does he like me?
0:05:15 Does he not like me?
0:05:22 And through that, we end up feeling what we think of as butterflies or chemistry, but it’s actually anxiety.
0:05:25 And it’s actually alarm bells in our head going off.
0:05:26 Do they like me?
0:05:27 Do they not like me?
0:05:27 Am I accepted?
0:05:35 And so sometimes it’s actually a sign of either the person giving you a hot, cold feeling or it can be somebody who’s a narcissist.
0:05:44 I’ve also found that let’s say I go to an event and I talk to some of my girlfriends later and I’ll say, oh, I really like that guy.
0:05:45 We really hit it off.
0:05:47 And then they’re like, wait, I really hit it off with that guy.
0:05:54 And we realized we all had what felt like unique connections to this person, but they were actually just really sparky.
0:05:57 And I imagine you meet a lot of people through doing this that are really sparky.
0:06:02 And so certain people just give off that spark and it’s not about your dynamic with them.
0:06:04 It’s about who they are.
0:06:08 And then the third myth is that if you have a spark, the relationship is viable.
0:06:10 We also know that that’s not true.
0:06:15 Just because you met the right way doesn’t mean that it’s the right relationship.
0:06:19 And so you can have a very sparky beginning, but it can fizzle out quickly.
0:06:24 And you shouldn’t stay in the relationship because you had a really good we met story.
0:06:29 And so my antidote to the spark is going after the slow burn.
0:06:35 And the slow burn is somebody who you like them more and more as you get to know them.
0:06:43 They may not be instantly the most charismatic person that you’ve ever met, but they’re really a quality person and they really grow on you.
0:06:50 And not because you’re settling, but because you’re looking for love in a different package than you originally thought.
0:06:54 You’re not just looking for the life of the party person that’s immediately as charismatic.
0:06:58 And so I feel like I’m married to a slow burn.
0:07:00 I met my husband in college.
0:07:03 We met again at Google a number of years later.
0:07:07 And now we’ve been together for almost 10 years.
0:07:13 And so he’s somebody where I really feel like as I got to know him more and more, I liked him more and more.
0:07:16 And so I really encourage people to go after the slow burn.
0:07:24 But wait a second, because what ends up happening in this is like you go out on a date and you’re like, maybe, maybe not.
0:07:30 And back in, you know, 1950, you’d have that, maybe, maybe, it was good enough to go out on again.
0:07:32 And then you’d see the person again.
0:07:38 But now you go home and you pick up your app and you open Hinge, you open whatever app you’re using.
0:07:43 And you had a average, but maybe slightly above average date that could be a slow burn.
0:07:48 And now you got 16 new messages from all these people who are more exciting.
0:07:55 And how do you do a slow burn in that case when all of these people, oh, like, look at this person.
0:07:55 They’re hot.
0:07:58 Oh, they want to text me and they want to see me.
0:08:03 And, you know, this guy or girl that I just went out with is like, oh, they set something up next week.
0:08:04 But that’s the slow burn.
0:08:06 How do you date in this environment?
0:08:11 Yes, so when I wrote my book, I have a chapter called Make the Second Date the Default.
0:08:14 And this was influenced by one of my mentors, Dan Ariely.
0:08:27 And the idea here was that if you go on a first date and you think about it as I’m going to be evaluating you the whole time and you’re going to either win a second date or not, it puts you in this evaluative mindset.
0:08:36 Instead, I want people to be in this experiential mindset where they’re asking themselves how the moment feels for them if they’re connecting with the person.
0:08:46 And so in the book, I say assume that every first date you go on, you’ll go on a second date and that will help you identify the slow burns more and to really take the pressure off the first date.
0:08:51 Well, since the book has come out, I feel like that advice is not that realistic.
0:08:52 People are busy.
0:08:57 People sometimes feel like I had no connection with that person.
0:08:59 I’m not going to go on a second date with them.
0:09:01 So I have changed my advice since the book came out.
0:09:08 And instead of thinking about it as Make the Second Date the Default, my go-to advice here is really to do the post-date aid.
0:09:21 So the post-date aid is a series of questions that I came up with for a client who was having a hard time deciding if she wanted to see someone again and also somebody who was having a hard time spotting the slow burn.
0:09:28 So when you finish the date, you look at this, you can have a screenshot on your phone or, you know, memorize the questions.
0:09:32 And they ask you things like, how did I feel in my body during the date?
0:09:33 Did I feel stiff?
0:09:35 Did I feel relaxed?
0:09:38 Did this person make me laugh?
0:09:39 Did this person make me feel heard?
0:09:42 Did I feel curious about the person?
0:09:46 And probably the most important one, what side of me did they bring out?
0:09:52 Because whatever side of you you are with that person is who you’ll be for a big majority of your life if you end up with that person.
0:09:59 And so the post-date aid is a great way to see if it was really a dud and you were 0% interested, forget it.
0:10:00 Don’t go on the second date.
0:10:09 But if there was maybe not the most charisma that you’ve ever encountered or there’s been people that you’ve been more attracted to in the past, it’s fine to acknowledge that.
0:10:16 But to think there was a seed of something that was planted that I’d like to give another chance to.
0:10:22 And so the post-date aid is a great way to see when there’s potential and to really spot those slow burn people.
0:10:26 Talk to me a little bit more about what side they brought out in you.
0:10:33 I’ve never thought of it that way, but looking back through some of my dates through this lens, I’m like, oh, I was defensive.
0:10:35 I was confrontational.
0:10:38 I was – yeah, go through that a little bit more.
0:10:44 Yeah, I’m glad that you’re double-clicking into that because it’s really something that I think about in a lot of areas of my life.
0:10:50 So when I was just making this career shift into the work that I do now, I met with a lot of different people to learn from them.
0:10:55 And I’m not going to say her name, but there was one person in particular that whenever I met with her,
0:11:00 I would just come home and sort of collapse into the couch and want to watch TV for the next few hours.
0:11:02 I was like, what’s going on with me?
0:11:12 And I was like, there’s something about the way that she communicates that makes me feel really small and anxious and like I don’t know what I’m doing and not good enough.
0:11:17 There was just something about the words that she used or the questions that she was asking.
0:11:22 And so that’s a platonic situation or, you know, it’s about career.
0:11:27 But in that moment, I understood I don’t really enjoy being around this person because she brings out a side of me that’s insecure.
0:11:31 Then I think about my friend Michaela, who’s one of my favorite people in the world.
0:11:34 When I’m around her, she laughs a lot.
0:11:35 She makes me feel hilarious.
0:11:39 We want to stay up all night talking because she makes me feel creative and generative.
0:11:47 And so I really will do whatever I can to be in the same room as her because she brings out a side of myself that I love.
0:11:53 And so when people are dating, especially as they get older, their checklists of what they think they need get longer and longer.
0:12:03 So that checklist might look like must be financially independent, must own their own home, must be this tall, must want exactly this lifestyle.
0:12:10 And so when they go into that date, they are really looking at those things, which are often who that person is on paper.
0:12:14 And then they ignore how they feel around that person.
0:12:19 Because, sure, you need some basic biographical data to decide if you want to go out with someone or not.
0:12:25 But once you’re on that date, it’s really about paying attention to who am I around them.
0:12:26 I love that.
0:12:28 And that applies to all areas of your life.
0:12:34 Is it your job in that moment to dissect why you’re having that response?
0:12:39 Or is it to just, I just don’t want to be around this person and that’s okay?
0:12:43 I mean, my cheeky answer would be it’s my job as your dating coach to tell you that.
0:12:49 But no, I think that in life, it really is great to dig into things like that.
0:13:00 So it might be, I’m just remembering this story where like early on when I shifted into doing the dating and relationship stuff, I met up with this guy and I thought it was like a peer-to-peer conversation.
0:13:04 And when I got there, he kind of leaned back and said, so what can I do for you?
0:13:11 And it was like that one statement kind of created a power dynamic, which was like, I have power and I can help you.
0:13:13 And I remember it really threw me off.
0:13:23 And so when I went home and I didn’t feel good and I reflected on it, I was like, oh, like maybe our expectations weren’t the same going into it or the person who did the intro didn’t set us up for success.
0:13:33 And so I made changes so that in the future when I had an intro like that, I was clear with the person introducing us, you know, what our goals were, things like that.
0:13:41 Or I find that if I’m really tired and I pushed myself to go to an event, I may not have a good time there because I don’t have energy to give.
0:13:56 And so I think for everyone, being more in touch with who you are, how you show up in different situations, what personality traits trigger you to feel more anxious or insecure, all of that is data that just helps you be a happier person.
0:14:04 And so something that I really promote people do is date like a scientist, which is this idea of have hypotheses.
0:14:10 So a hypothesis could be, I need to date somebody with a graduate degree, but then test that hypothesis.
0:14:21 Maybe what you actually care about is intellectual curiosity and somebody who listens to the knowledge project, not somebody who has a master’s degree or a PhD.
0:14:29 And so really having a hypothesis, testing it, and then being willing to be willing to be proven right or wrong.
0:14:41 I think if we all live like a scientist and date like a scientist, we learn so much about ourselves, we push ourselves, and we actually wind up in a much happier place than if we just follow all the assumptions in our head.
0:14:52 I want to double-click on the date like a scientist thing a little bit, and maybe I’ll bring an anonymous friend into this who runs a business, very successful, very ambitious, very wealthy.
0:15:01 In theory, he checks all these boxes that women would want, but in reality, I mean, his saying is they don’t want what comes with that.
0:15:08 Is that, what do you mean by dating like a scientist in the checklist, and maybe I’m loosely working around this.
0:15:25 Yeah, so I would say a majority of my clients at this point are sort of more powerful male CEOs, and I feel like it is interesting to just hear, you know, women are excited about what they have access to, but then they may not understand that this person works 18 hours a day.
0:15:36 Or that maybe this person has a chip on their shoulder because when they weren’t successful, they felt like they didn’t get a lot of attention, and so I feel like the unique problems of that situation are something that I’ve dealt with.
0:15:38 So just breaking down date like a scientist.
0:15:46 When I work with people in my coaching, in my courses, people walk in with assumptions of what they need.
0:15:55 So it might be, I need to date somebody who’s six feet or taller because I’m a taller woman, and that’s what makes me feel feminine.
0:16:02 So then I might say to them, hey, in the United States, only 14% of men are six feet or taller.
0:16:07 So now you are eliminating 86% of the male population.
0:16:10 You’ve been actively dating for 12 years.
0:16:12 This has not worked out for you so far.
0:16:18 Why don’t you change your filter on the dating apps, be willing to date somebody who’s shorter, and see.
0:16:24 Maybe what you actually care about is somebody who’s confident where your height doesn’t feel like a factor.
0:16:32 Maybe you’ll end up with somebody a lot shorter than you, and this is what happened to a man and a woman that I know, because it’s not about how tall the guy is.
0:16:34 It’s about how they make you feel.
0:16:48 And so her dating like a scientist moment would be changing her filters on the app, dating some men who are shorter, seeing if she can feel attracted to them and attractive with them, and then understanding it wasn’t height that was the deal breaker.
0:16:53 It was confidence or how attracted she was to them and how attractive they made her.
0:16:56 That six feet thing is like such a killer.
0:16:59 I’m like 5’11 and three quarters.
0:17:00 It’s like, what do you do?
0:17:02 Do you say six feet or do you do 5’11?
0:17:05 In which case, every woman has this like six feet.
0:17:07 The height thing is really interesting.
0:17:20 So I would say over the last few years, the posts of mine that have gone the most viral are reels where I’ve posted about this stat because in the comments, you have a lot of women saying, well, guys lie about their height anyway.
0:17:24 And then guys say things like, yeah, you should change the height filter.
0:17:28 And then women say, well, you filter based on weight.
0:17:32 And so anyway, it’s just really interesting to see how much this bothers people.
0:17:45 And I wish that I could kind of shout from the rooftops to everyone and say, imagine that you were in a bar and you were sitting next to somebody and you’re both sitting on stools and you have a 45-minute conversation that is incredible.
0:17:46 It’s deep.
0:17:47 It’s soulful.
0:17:48 It’s mind-blowing.
0:17:53 And at the end of the date, the guy stands up and he’s 5’7.
0:17:56 Are you telling me that you’re not giving him your number now?
0:18:03 No, of course you’re going to give him your number because you just saw who this person was and what an incredible connection you had.
0:18:06 And in that moment, you’re not thinking height first.
0:18:08 You’re thinking connection first.
0:18:17 And I really want people to change their framework and to understand, yes, the filters exist, but you are filtering out so many great potential connections.
0:18:27 Why not date like a scientist, see if these things that you think are deal-breakers are really deal-breakers when most of the time they’re not and move them to the pet peeves or nice-to-have column.
0:18:31 It strikes me as a difference between how we used to date and how we date now.
0:18:34 So we used to date in a way that like a guy would call on you.
0:18:36 You might not know him well.
0:18:37 You might have friends.
0:18:41 You might have met through your parents or something, but you don’t know much about him.
0:18:43 And then you spend time with him.
0:18:47 So your first impressions, but now we’re filtering before you even get to that point.
0:18:50 We’re filtering based on a dating profile.
0:18:51 We’re filtering based on pictures.
0:18:53 We’re filtering based on politics.
0:18:55 We’re filtering based on all of these things.
0:18:58 I want to come back to the spark thing.
0:19:00 Is there a difference between the spark and lust?
0:19:06 I’ve thought about this a lot because, you know, when you write a book, you’re writing it alone.
0:19:08 Maybe a few people read it and your editor reads it.
0:19:12 And then when it’s out into the world, you really get to see what takes off with people.
0:19:17 And so I would say a few things have taken off and one of them is this concept of fuck the spark.
0:19:26 And so people have really strong reactions when I say that because they feel like, oh, Logan’s telling me I shouldn’t be attracted to the person or it doesn’t matter.
0:19:27 Logan’s telling me to settle.
0:19:33 Wait, I said fuck the spark and then I met someone I wasn’t interested in and I dated them for six months and it didn’t work out.
0:19:37 And so I really want to talk about what the spark is.
0:19:45 The spark is a huge emphasis on instant chemistry and instant connection versus allowing it to grow over time.
0:19:48 I would say that lust is about attraction.
0:19:52 And a lot of times, you know, I want to have sex with this person.
0:19:54 I hope this person wants to have sex with me.
0:19:59 And I think being sexually attracted to someone is, of course, something that you should look for in a relationship.
0:20:07 But it’s slightly different from the spark, which is this overall feeling of like when I meet someone, I want to be around them more and more.
0:20:14 And the big message I’m trying to get across here is that that feeling of chemistry can grow over time.
0:20:21 What should a first date look like to maximize information gathering or connection, I guess?
0:20:26 Yeah, you know, I will even push on that question and say, I don’t think it’s about information gathering.
0:20:29 Imagine that you spend 50 years with someone.
0:20:35 The day that you meet is 0.0055% of your total time with them.
0:20:39 And so it’s not about gathering information.
0:20:41 It’s about having an experience with them.
0:20:48 So one thing that I’ve done through my research is look at people who are consistently getting asked on second or third dates.
0:20:52 Look at people who people really are drawn to.
0:20:55 And when I talk to these people, it’s not what you might think.
0:20:56 They’re the tallest people.
0:20:57 They’re the hottest people.
0:20:59 It’s often that they’re very fun.
0:21:12 They meet up with you on a date and they tell you a funny story or they have a silly interaction with the bartender or they tell you about what happened at work that day and the funny situation that they got into.
0:21:15 There’s something about them that’s very vibrant and lively.
0:21:21 And when people are around them, they feel like they are also having an experience.
0:21:22 They’re not just exchanging information.
0:21:31 And so I think if we think that a first date is really about I need to leave and know your biography, that’s not really fun for either person.
0:21:38 If it instead shifts to what I was talking about, our first date is about seeing how does it feel to be around the person?
0:21:40 What side of me do they bring out?
0:21:42 Those dates end up being so much more successful.
0:21:49 Because even if they don’t lead to a relationship, they lead to you knowing how would it feel to be with this person.
0:21:50 I like that a lot.
0:21:57 What are the indicators that I should be looking for on a date that would lead to emotional connection?
0:22:05 So one thing that I’ve looked at a lot is this idea of what matters more and less than we think for long-term relationship success.
0:22:11 So a lot of the things that people think matter more than they do include things like looks and money.
0:22:13 So, of course, looks matters.
0:22:15 We just talked about lust.
0:22:17 You want to feel attracted to the person.
0:22:26 But I wouldn’t give anyone the advice of try to date or marry the hottest person that you’ve ever met or the person maybe who you’ve had the hottest sex with in your life.
0:22:41 And so if you think about some of the most beautiful celebrities in the world, there are often people kind of known to humanity who have cheated on them.
0:22:51 And so it’s like if even these people that are considered the most attractive by cultural standards are being cheated on, there’s this idea that people adapt over time to somebody’s looks.
0:22:55 And even if someone’s really attractive, we’ll get used to that over time.
0:22:57 The same thing is true with money.
0:23:00 I know this amount of money has changed over the last few years.
0:23:04 But, you know, they used to say happiness doesn’t change over $75,000.
0:23:06 Now I think they’ve raised it.
0:23:09 But it’s this idea that whatever amount of money you have, you get used to.
0:23:13 A few more things that matter less than people think they do.
0:23:16 So people think, we need to have all the same hobbies.
0:23:19 If I love wine, I want someone who loves wine too.
0:23:22 And you don’t actually have to share the same hobbies.
0:23:28 You just need to support the other person’s hobbies and have them support yours so that you can continue investing in that hobby.
0:23:31 And you don’t have to have the same personality.
0:23:34 Sometimes people will say, I have a big personality.
0:23:35 I love to go out.
0:23:37 I want to find a woman who does the same thing.
0:23:39 And I’m like, no way.
0:23:44 Two of you in a room, two of you at a dinner party, two of you in a relationship, that’s way too much.
0:23:47 I want you to find somebody who grounds you.
0:23:51 And it’s often about being complimentary versus being the same.
0:23:55 So that was really the category of matters less than we think it does.
0:23:58 For the things that matter more than people think they do.
0:24:00 So the first one is loyalty.
0:24:03 Really, is this somebody who will stick by you?
0:24:06 Of course, that’s a hard thing to find out on a first date.
0:24:15 But one proxy for that that I found is asking people about old friendships, people who have friendships from different phases of their life.
0:24:16 Do they hang on to people?
0:24:18 Or when they move, do they let those go?
0:24:21 Or are they social climbing and always trying to trade up?
0:24:25 So does this person keep friends from different phases of their lives?
0:24:27 Another one is emotional stability.
0:24:30 And that’s also hard to figure out on a first date.
0:24:33 But how does this person deal with adversity?
0:24:36 How does this person deal with frustrations?
0:24:41 Are they somebody who can sort of pause and think before they react?
0:24:45 Another one is the ability to make hard decisions together.
0:24:49 So early in dating, you’re maybe not making a lot of hard decisions together.
0:24:52 But pay attention to how you talk about things.
0:24:58 Like if one person wants to meet up near their house and the other person wants to meet up near their house, are you debating it?
0:24:59 Are you compromising it?
0:25:01 Are they listening to your needs?
0:25:06 There’s so many ways to really perceive who someone is if you’re actually looking for these things.
0:25:14 And then the one that I’ve been talking about, which is what side of you they bring out, and really thinking about the dynamic itself.
0:25:22 And that understanding that a relationship is not about two instruments on their own, but it’s about the music that you’re making together.
0:25:30 And really paying attention to almost this third object of the dynamic between the two of you, as opposed to just who that person is on their own.
0:25:36 I had a friend who made this comment, well, we just adjust to what we have.
0:25:41 And then we kind of like we are human, so we yearn for something different than what we have.
0:25:46 Yeah, my husband is very scientific, and he’s worked in a lot of different labs.
0:25:58 And when we first started dating early on, he said some quote to me, or he was telling me about some study, which is like there’s a male rat in a cage, and they put in a female rat.
0:26:03 And at first they have sex, but over time the male rat gets sick of having sex with that female rat.
0:26:12 But then if you keep replacing the rat with new female rats, that male rat will have sex with those female rats until it literally passes out from exhaustion.
0:26:17 And so it’s just this idea of, yes, a lot of what is sexually exciting to people is novelty.
0:26:26 And so instead of being disappointed or frustrated by that in a monogamous long-term relationship, you can just think about the fact that I acknowledge that that will happen.
0:26:34 And so I’m not going to spend all of my, you know, partner choosing coins just on looks because that’s not a good long-term strategy.
0:26:40 Do you think we’ve sort of broken dating in a way where, I mean, I’ve been on dates with people.
0:26:43 We all know people who are, I wish people would come up to me and ask me out.
0:26:45 I wish I didn’t have to use a dating app.
0:26:53 And my defense of, you know, thinking immediately in this is like society has taught guys not to approach women anymore.
0:26:54 What’s your reaction to that?
0:26:59 This is something that I’m thinking about a lot, specifically with Gen Z and Gen Alpha.
0:27:07 So I was recently speaking to somebody, she’s a 16-year-old entrepreneur, and she’s trying to deliver help for teen daters.
0:27:12 And she said by far the number one thing that she gets questions about is how to deal with rejection.
0:27:31 And so I am genuinely concerned that because of different societal factors, because of people who maybe lost out on some social skills during the pandemic, because of people who live a lot of their lives online, there is not that rejection resilience that many of us need in life.
0:27:36 So if you want your dream job, you need to go out there, get a lot of no’s, and go after it.
0:27:40 You don’t just sit at home waiting for a LinkedIn recruiter to message you about your dream job.
0:27:42 That doesn’t happen.
0:27:43 You have to make it happen.
0:27:48 And the same thing is true with dating, is that you have to shoot your shot.
0:27:49 You have to approach people in public.
0:27:51 You have to take a risk.
0:27:59 And so I’m encountering a lot of people who are very afraid of rejection and are not taking those risks.
0:28:01 And I think that it’s leading to fewer relationships.
0:28:04 I’m a make it happen kind of person.
0:28:04 I can tell.
0:28:11 In work and in life, I also know that that can come off as aggressive or assertive.
0:28:13 How do you deal with that?
0:28:14 That’s interesting.
0:28:17 So what’s a scenario that you feel like could come across the wrong way?
0:28:23 Well, make it happen is like you have a great first date or something, and then you’re instantly like on to the next date.
0:28:25 You know, you’re like, I want to see you again.
0:28:26 How about tomorrow?
0:28:29 And then the other person, I don’t know.
0:28:34 Like, I feel like we’re just in a society now where, you know, you’re supposed to wait till tomorrow almost.
0:28:37 And I hate personally waiting.
0:28:39 I’m sure there’s other people out there like me, too.
0:28:41 Where it’s like, no, you’re in charge.
0:28:42 You have agency.
0:28:44 And you can make the world happen.
0:28:53 I love this question because I think it speaks to a really real phenomenon where people are experiencing excitement about somebody, but they feel like they need to hold it back to seem cool.
0:28:57 And so I love to talk to people about attachment theory.
0:28:59 Has that come up on your podcast before?
0:29:00 No, let’s go into it.
0:29:00 Okay.
0:29:06 So attachment theory is something in the world of relationship science that’s truly backed by the research.
0:29:11 It’s something that first came about around 60 years ago with someone named John Bowlby.
0:29:17 And this research was originally done with children to see their attachments to their primary caregiver.
0:29:21 But now we have an entire field of adult attachment specifically around relationships.
0:29:25 And so there are people who are anxiously attached.
0:29:31 What happens for them is their story of love is that I’m going to chase you.
0:29:33 I have to convince you to like me.
0:29:34 You might pull away.
0:29:42 And we’re going to have this chase dynamic and that I’m constantly worried that you’re not going to be interested in me and you’re going to disappear.
0:29:49 So how those people show up in relationships, and I know because I really was one of these daters, is if you don’t hear back from somebody, you start spiraling.
0:29:50 They met somebody else.
0:29:51 They don’t like me anymore.
0:29:54 You send a bunch of texts to try to reconnect with them.
0:30:01 And you’re often just in this danger zone where you’re not being the person that you want to be because you’re trying to have this reconnection moment.
0:30:03 You think somebody is going to pull away.
0:30:05 Then there’s people who are avoid and attached.
0:30:08 They sort of have the opposite experience.
0:30:11 Their version of love is I’m going to be smothered.
0:30:12 I’m going to lose my independence.
0:30:17 And when they get too close to somebody, they are the ones pulling away.
0:30:20 So they’re the ones, you know, great sleepover on a Saturday night.
0:30:21 Sunday morning, they wake up.
0:30:22 The person hasn’t left.
0:30:25 And they’re like, damn, should I call her an Uber?
0:30:26 Oh, my God.
0:30:26 That’s me.
0:30:27 That’s you?
0:30:27 Yeah.
0:30:30 You have that feeling of like, I need my space.
0:30:32 Well, I need my space and I don’t want to get hurt.
0:30:34 There’s like an element of vulnerability.
0:30:35 Absolutely.
0:30:37 What you’re talking about is complete true.
0:30:40 It’s not that those people don’t want to be in intimate connection.
0:30:45 It’s that the fear of being smothered or the fear of being hurt causes them to pull away.
0:30:48 I’m going to reject you before you reject me.
0:31:01 And so for those avoidant attached people who think that they’re going to be smothered, and then for the anxiously attached people who think they’re going to be abandoned, what ends up happening is they often date each other and they reinforce this idea.
0:31:03 So I think that love is a chase.
0:31:05 You think that love is being smothered.
0:31:07 So when I go after you, you pull away.
0:31:09 That reinforces mine and that reinforces yours.
0:31:16 And anxious, attached, and avoidant people keep dating each other in this anxious, avoidant loop that leaves both people feeling pretty unhappy.
0:31:20 But there’s a third type of securely attached people.
0:31:26 And these are people who have a healthy relationship with independence and with intimacy.
0:31:30 I want to be close to you, but I also respect and need my alone time.
0:31:39 And so often the way that people get out of the anxious, avoidant loop is they either become more secure themselves or they date someone who’s secure.
0:31:50 And so that’s what happened for me after, you know, 10 years of chasing after different people, being rejected, being disappointed, thinking, well, if only I could prove my value, then this guy would like me.
0:31:59 Instead, when I dated somebody who was secure, it broke a lot of those patterns, and we formed what I feel like is my first really healthy relationship.
0:32:09 What happens is 50% of the population is secure, which sounds like a good thing, but those people are so good at being in relationships that they often get snatched up and you have the anxious and avoidant people dating each other.
0:32:18 But in the example that you described, it can actually be very secure for somebody to follow up after a date and say, hey, I really enjoyed getting to know you.
0:32:19 I’d love to see you again.
0:32:21 When are you free?
0:32:29 And in that moment, somebody who’s used to dating somebody who’s avoidant might be like, whoa, they’re coming on too strong or that’s so obvious.
0:32:30 They’re so obviously interested.
0:32:31 That’s boring.
0:32:41 But a ton of the work that I do is training people to identify secure partners and to reestablish them in their heads, not as boring, but as secure.
0:32:54 So sometimes that person who pulls away is exciting, that sparky feeling because you don’t know if they like you or not, but instead really honoring the person who says, I like you.
0:32:55 I’m interested.
0:32:56 When can I see you again?
0:33:01 And so the slight tweak that I would have to yours is not, I like you, can I see you tomorrow?
0:33:06 That does kind of feel a little bit intense, but being clear about like, hey, that was a really great date.
0:33:07 I feel like we really connected.
0:33:09 I’d love to see you again.
0:33:13 And then like working together to come up with the next date.
0:33:20 And a lot of dating that people miss is that it’s about matching somebody’s momentum and matching somebody’s speed.
0:33:25 So it’s a dance where I take a step forward and then you need to take a step forward.
0:33:29 If I take 10 steps forward, you might feel overwhelmed and take a step back.
0:33:32 So just paying attention to, are you always the one reaching out?
0:33:34 Are you always the one making plans?
0:33:39 There needs to be momentum matching for the speed to feel right to both people.
0:33:44 So last year, I realized something was getting in the way of myself.
0:33:47 What sparked this in our conversation was freedom.
0:33:54 And so I decided to do therapy for the first time as my adult life as a single person.
0:33:58 I did marriage counseling as well before my divorce.
0:34:05 But it was so fascinating to me because one of the things that led to this was I wouldn’t accept compliments from people.
0:34:13 The minute somebody started to say something positive, my brain would turn off and I would instantly move to the groceries.
0:34:14 What’s next in the conversation?
0:34:16 I’d stop listening.
0:34:29 And what came out of this is that compliments in my body, I had somehow associated compliments with power over me because at some point they were taken away.
0:34:33 And so it was like, I’ll compliment you as long as you do what I want.
0:34:36 And then all of a sudden, and so I would associate these things.
0:34:41 And so I developed this really strong aversion to people having power over me.
0:34:59 And so loss of freedom is a great example of like how that manifests itself in dating where it’s like, no, like that’s really hard in dating context because I default to the state of I want to continue to do the things that I’m doing in the way I’m continuing to do them.
0:35:06 And that makes it really hard to find somebody and build a life together and adapt to each other.
0:35:08 That’s super interesting.
0:35:22 So for the compliments, was it that you grew up in a home where there was a strong sense of external validation if you did the right thing and then you felt like you constantly had to please someone and the compliments were a sign that you were doing the right thing.
0:35:25 But then they could be taken away if you didn’t do the right thing.
0:35:27 I don’t quite know.
0:35:29 A lot of people remember a ton about their childhood.
0:35:30 Yeah.
0:35:30 I don’t.
0:35:34 I remember certain moments and like not a lot before grade eight, to be honest with you.
0:35:38 And I was like, I got into a ton of trouble as a kid.
0:35:39 I was a bit of a misfit.
0:35:44 But the thing that I learned at a very young age was just not to pay attention to them.
0:35:50 See, because that could also be a positive thing where you have an internal locus of control that’s not looking to other people.
0:35:54 Like even my daughter is one and she started doing this toy.
0:36:00 Maybe you remember it where it’s like, you know, there’s a stick and then you put the different round things on top of it.
0:36:04 And when she does it, every time she puts one on, she claps and she doesn’t even smile.
0:36:07 She just thinks that that’s part of how the toy works.
0:36:10 You put it on and then you clap for yourself because when she does it, we clap for her.
0:36:18 I was like, she’s a brand new human in the world and she’s already learning that she’s doing things for external validation.
0:36:23 Or it’s the clapping to me is really bothering me where I’m like, we’re not going to clap anymore.
0:36:28 We cannot reward her for every single thing because then she will be doing it for us and not for herself.
0:36:33 And so it’s so interesting that compliments shut you down.
0:36:34 Well, they used to.
0:36:37 I’ve done much better since then at sort of being vulnerable.
0:36:39 Like I never wanted to be vulnerable.
0:36:49 I would get to this point and this goes back to the attachment styles is I needed to feel like somebody else couldn’t hurt me or take something away because I’m giving them power over me in a way.
0:36:50 Power to hurt me.
0:36:51 I don’t know.
0:36:52 I’m messed up.
0:36:53 If you’re listening to this, like.
0:37:09 I’m just going to push this topic because I think it’s so interesting, but on my first date with my husband, he told me that when people tease him or troll him or it actually makes him feel very close to them because something inside of him was like, oh, I’m a piece of shit.
0:37:15 So if somebody like, if somebody sort of like calls that out, it makes him feel known.
0:37:16 And like, I don’t know.
0:37:17 It’s like you see me.
0:37:36 Yeah, so I don’t know that that happens all the time, but like it is something that I’ve seen with certain people who are maybe more powerful or dominant is that when somebody actually calls them out on stuff, it makes them feel like, oh, I can trust that person because they see my flaws and they know from the beginning what my flaws are.
0:37:40 I don’t have to put up a front of seeming perfect all the time and then disappointing them.
0:37:48 Like this is a whole rabbit hole of like, I don’t want to let somebody in because if they knew the real me, then they would reject me.
0:37:49 Yeah, totally.
0:37:53 If you saw all of me, then you wouldn’t, I’m not lovable is effectively what you’re.
0:37:59 That is such a big part of the work that I do is this idea of people come to me and they think I’m undateable.
0:38:00 Yeah.
0:38:01 Do you feel that way?
0:38:03 Generally, yeah.
0:38:04 You feel undateable.
0:38:05 Well, I feel unlovable.
0:38:06 Like I do feel like.
0:38:07 Yeah, let’s use those words synonymously.
0:38:17 If somebody saw all of me and could see my inner monologue and just had like full access to me, then they wouldn’t love me, of course.
0:38:21 I think that’s extremely common and it has different ways that it comes up.
0:38:25 So some people say to me, you know, I have a chronic illness.
0:38:26 I’m unlovable.
0:38:28 I have an STI.
0:38:29 I’m unlovable.
0:38:30 I’ve never been in a relationship.
0:38:31 I’m unlovable.
0:38:33 I’ve been in too many relationships.
0:38:33 I’m unlovable.
0:38:39 And so many people have this inner narrative around how if somebody really, really knew them, they wouldn’t love them.
0:38:47 And what’s so hard for people to understand is like it’s often that vulnerability and that imperfection that connects people.
0:38:51 Because I think about friends of mine or people I know who come across as perfect.
0:38:56 And I’m like, you have such a glossy exterior that there’s nothing for me to grab onto.
0:39:06 Actually need cracks in the wall to grasp onto and to have a connection with you and to feel like I can be my full imperfect self.
0:39:12 And so it’s like the thing that we think makes us unlovable is often what makes somebody feel comfortable around us.
0:39:18 But if we truly feel like we’re unlovable, we never open up and give somebody the chance to see that for themselves.
0:39:25 I want to come back to sort of dating just a little bit and profiles, like how you end up on a first date.
0:39:31 One thing that I think everybody does these days is they Google the other person.
0:39:35 And for whatever reason, I mean, people think this doesn’t happen.
0:39:36 I don’t know why.
0:39:41 Like you can upload photos from dating websites and find out who the person is fairly easily.
0:39:44 How does that work for you and against you?
0:39:46 It’s so interesting.
0:39:58 So there’s research on the brain that shows when our brain gets an incomplete picture of something, we fill in the gaps in a way that makes it more positive.
0:40:03 So have you ever seen a black and white photo of yourself and think, oh, I look pretty good in that?
0:40:05 I’ve never seen a photo of myself where I think I look pretty good.
0:40:12 Okay, well, take a photo of yourself and make it black and white and you might be like, huh, I’m looking pretty good there.
0:40:19 And the point is that by taking out the color and actually some of the information, our brain fills in the gap and it actually often looks more attractive than it does.
0:40:22 The same thing happens on dating app profiles.
0:40:27 So if somebody says, I love music, our brains fill in the gap and think, oh, they love music.
0:40:28 You know, I really like hip hop.
0:40:30 I bet they like the same music that I do.
0:40:34 And with this incomplete picture, we start building up this fantasy in our head.
0:40:45 And that’s why people get into this really bad situation where they start talking to somebody and they’re almost pen palling and having all these text conversations and building up this fantasy.
0:40:50 And by the time they meet in person, that person’s great, but they’re not the fantasy you had in your head.
0:40:54 And so you reject them because they’re different from who you thought they were.
0:40:58 And that’s why it’s so important that people get to the date faster.
0:41:06 Honestly, meet on Hinge and a few days later, we’ve actually found that the sweet spot is after three days of chatting, just say, hey, I always walk my dog at 6 p.m.
0:41:10 Can I give you a phone call or do you want to FaceTime for a few minutes tonight?
0:41:23 And instead of turning the digital courtship phase into this weeks-long thing, make it much shorter, get on the phone, get on FaceTime, see if you have a connection, and then meet up in person as quickly as possible.
0:41:35 And so I actually think the point is to learn who the person is by talking to them directly versus either having your brain fill in the gaps or doing all this external research that might be incorrect or outdated.
0:41:38 So two rabbit holes I want to go down here.
0:41:39 Well, actually, one comment.
0:41:42 It’s interesting that you said we fill in our own gaps.
0:41:48 Matthew Dix, who’s like the Olympic storytelling champion of the world effectively, was on the podcast.
0:41:55 And one of the things that you said that just triggered this is when he was describing, he’s like, I describe but vaguely.
0:41:57 So everybody sees their own thing.
0:42:06 If I say kitchen floor, I don’t describe like green linoleum tiles because the minute I say that, people might have a hard time picturing it.
0:42:09 But everybody knows what their kitchen floor is.
0:42:12 So he used this example of I’m in the back of my school.
0:42:14 My back is up against the wall.
0:42:20 And he’s like, it doesn’t matter what my school looks like because everybody has this own image of their school.
0:42:22 And I don’t know why, but I connected those two things.
0:42:25 Just to comment on that, like, I definitely want to listen to that episode.
0:42:27 Was it an episode you recorded with him?
0:42:27 Yes.
0:42:31 Because I’d love to learn from that because, you know, a big part of my job is communicating.
0:42:37 And it’s so true that stories are really the filing system of our brain.
0:42:37 Totally.
0:42:41 And I was thinking last night about the story of the boy who cried wolf.
0:42:51 And I was like, it’s so smart that we teach kids fables because if somebody had sat me down and said, if you raise a lot of false alarms when it’s a real alarm, no one’s going to listen.
0:42:53 Like, I wouldn’t remember it.
0:42:54 But the boy who cried wolf, it’s so memorable.
0:43:01 It’s like that’s why we have these oral storytelling traditions and even, like, you know, why the Bible is the greatest meme of all time.
0:43:03 People really remember these stories.
0:43:13 And so that is a good tip that I’m going to use, which is, you know, you want to be speaking about visuals, but maybe vague enough details that people can insert their own version of the kitchen floor.
0:43:14 I love that.
0:43:17 You should listen to the episode I did with Becky Kennedy, too.
0:43:22 She talks about how she made up stories to teach her kids lessons.
0:43:23 That’s really cool.
0:43:24 Which it is so powerful.
0:43:26 It’s such a power because we remember stories.
0:43:27 We don’t remember facts.
0:43:27 Not at all.
0:43:27 We don’t remember digits.
0:43:31 And that’s actually part of dating advice that I give people.
0:43:35 So, you know, I have people who come in who are amazing communicators, really charming.
0:43:39 They just kind of have a few things holding them back from connecting, and we work on that.
0:43:42 I have other people who come in who have never been on a date in their life.
0:43:47 From that starting point, we really have to start talking about, like, how do you have a good conversation?
0:43:54 And so one of the key ideas there, you basically just said these words, is share stories, not facts.
0:43:56 And so what’s an example of that?
0:43:58 Well, a fact would be that you have a younger brother.
0:44:03 A story would be your younger brother lives across the country from you.
0:44:04 You haven’t met your niece yet.
0:44:08 You feel sad about the lack of connection with that person.
0:44:12 And one of your resolutions is to really get closer to your brother.
0:44:20 And so I think oftentimes when people are less experienced with first date conversations, they share the facts about their lives.
0:44:22 And it’s not memorable and it’s boring.
0:44:29 And really think about the emotions and the feelings and the stories behind those facts because that’s what a good conversation is.
0:44:34 Walk me through a little bit more about good conversations on a first date.
0:44:47 I think a lot of people tend to just have this list of questions almost that they’re like, it doesn’t quite feel like an interview, but it kind of feels like an interview on the same token.
0:44:48 How do you get out of that?
0:44:49 Okay, let’s think of examples.
0:44:55 So I think a bad question would be, what did you study in college?
0:44:59 I think then you’re just finding out about a fact about somebody about their major.
0:45:08 I think a good question would be something like, oh, you just told me that your job was a marketing manager for this tech company.
0:45:11 Like, how is that different from what you thought it would be?
0:45:16 Or can you see yourself doing that for a long time?
0:45:18 Or like, what changes would you want to make to it?
0:45:19 And that one might be a little interviewee.
0:45:27 But I think the point is that if you go on a first date and you’re information seeking, then what you will get is facts.
0:45:32 If you go on a date and you’re connection seeking, then what you will get are stories.
0:45:33 I like that.
0:45:35 That’s a good way to do it.
0:45:39 One of the things you brought up was having a phone call first.
0:45:41 Is that like the recommended protocol?
0:45:41 Yeah.
0:45:47 So before the pandemic, I did not like the idea of video dates or phone calls before a first date.
0:45:51 To me, it triggered this idea of like a tech job and a phone screen.
0:45:55 Like that 15-minute call with the Google recruiter to see if you’re crazy or not.
0:46:01 And I felt like it was going to create too much of a feeling of, okay, I saw who you were.
0:46:02 I’m not interested in you.
0:46:03 I’m out.
0:46:07 But during the pandemic, that was the only way that people could really date for a while.
0:46:12 And so there was this proliferation of video chats or phone dates.
0:46:18 And I actually felt like they were a great technique for people to just see, can we hold a conversation?
0:46:19 Are they who they say they are?
0:46:23 It makes people feel more safe before meeting up for the first time.
0:46:33 It helps people who are really busy, like executives or single parents, feel like, is this somebody who I want to get a babysitter for in order to meet up with them?
0:46:36 And so now I actually think that it’s a really helpful technique for a lot of people.
0:46:38 And what do you cover on that call?
0:46:39 Like say it’s 15 minutes.
0:46:45 Like you’re just trying to get a feel for the person, like the awkwardness or like what do you?
0:46:51 Yeah, you know, I think that you could start the conversation and just start talking about your day.
0:47:00 So, for example, I like to tell people about this concept of in media res, which is a Latin term that means in the middle of things.
0:47:11 So a play might open up in the middle of a battle scene and then it sort of zooms out and later you find out who’s in the battle, why are they in the battle, what’s going on.
0:47:14 But it really just captures your attention right away.
0:47:22 And so you could enter a date or a phone call and say, hey, I’m Logan, this is where I live, this is what I do.
0:47:24 I’m like, I’m already asleep just talking about this.
0:47:35 But instead, if you walk in there and you say, so my sister called me this weekend and she’s having this issue at work and she told me this, but I thought that she was handling it the wrong way.
0:47:36 What do you think about that?
0:47:43 It’s like, boom, we’re friends, we’re having an experience, I’m hearing how you think, I’m hearing if you give good advice, I’m learning about you.
0:47:49 I’m not trying to glean information from you and facts about your life.
0:47:52 I’m truly trying to get to know you as a person and how you think.
0:48:01 And I feel like for me as someone who’s been with my partner for 10 years, who has a new baby, so much of my life is how my partner thinks.
0:48:03 That influences my life.
0:48:05 That influences the decisions we make together.
0:48:07 It influences whether or not I trust him.
0:48:21 So I really think just creating these conversational dynamics where we’re expressing ourselves, we’re responding to situations, we’re not just repeating the same tape in our head that we press play on in every boring first date.
0:48:26 That, to me, is so much more fun and provides such deeper information.
0:48:27 No, I love that.
0:48:32 I want to, like, also come back, we’re sort of in a rabbit hole here a little bit, to attachment.
0:48:40 You know, I feel like I’ve taken steps individually towards more secure and away from avoidant attachment.
0:48:52 What are the things that we can do, short of finding a partner who’s safe and secure, that reinforces the best in us and gives us patience and tolerance for the worst in us?
0:48:56 What are the things that people can do individually to put themselves in a better place?
0:49:01 And, you know, you don’t have to make that leap overnight, but what are the steps that we can take to get to a better place?
0:49:11 Right. So people do tend to have one attachment style, and it’s a mixture of genetics and how they were raised, but around 25% of people are able to shift their attachment over time.
0:49:15 So if you are insecurely attached, there is hope.
0:49:19 It’s not just, oh, I need to find one of those securely attached people that’s already in a relationship.
0:49:26 So for people who are anxiously attached, it’s really important to understand triggers for you.
0:49:33 So a trigger for somebody who’s anxiously attached might be, I text the person I’m seeing all day, but I just sent them a meme.
0:49:35 They usually respond to that right away.
0:49:37 They haven’t responded in four hours.
0:49:37 Okay.
0:49:39 So a trigger was not hearing back from somebody.
0:49:50 What usually happens in that moment is you sort of go down into the danger zone, and you start, you know, texting them a bunch of times.
0:49:51 Hey, what happened?
0:49:52 Or you spiral in your head.
0:49:54 They don’t like me anymore.
0:49:55 They met somebody else.
0:49:58 When I said this thing two days ago, they thought it was super weird, and they’re pulling back.
0:50:07 And then they sort of do these behaviors to try to reconnect with the person, which can really turn the other person off.
0:50:14 And so instead, set yourself up for success by not getting to the danger zone in the first place.
0:50:19 So when you feel like, oh, no, they didn’t respond to my text, what are other things you could do?
0:50:24 So you could text a friend and distract yourself with the conversation with them.
0:50:28 You could even tell a friend, oh, this is what I’m feeling, and, you know, make me feel better about it.
0:50:29 Give me a pep talk.
0:50:30 You can give yourself a pep talk.
0:50:33 There’s this concept called disconfirming evidence.
0:50:38 So basically explaining to yourself, no, they just have a busy day.
0:50:39 They’re at that conference.
0:50:41 They told me that they weren’t going to be in touch.
0:50:43 Why am I jumping to conclusions?
0:50:45 Let me just wait and see what happens.
0:50:52 And so there’s different things that you can do to sort of catch yourself before you start doing those protest behavior things,
0:50:55 like sending a million texts or calling them and then turning your phone off.
0:50:58 For avoid and attach people, it’s the same thing.
0:51:04 The danger zone is when you feel really overcome by them and that you’re losing your independence,
0:51:07 and you might notice strategies that happen for you.
0:51:09 So with anxiously attached people, it’s activating strategies,
0:51:13 and with avoid and attach people, it’s deactivating strategies.
0:51:16 So in your head, you start thinking, oh, they’re not really that cute.
0:51:20 I’m not interested in them, or I can’t believe she pronounced that word that way.
0:51:20 She must not be that smart.
0:51:23 So it’s almost like you’re giving yourself a reason why you don’t like them to push away.
0:51:25 I wonder if you ever do that.
0:51:26 Oh, totally.
0:51:26 Yeah.
0:51:33 And so instead, what to do in those moments is to really realize that you need space and just ask for it.
0:51:37 So for example, if you have that Saturday night sleepover and Sunday you want your space,
0:51:40 you can just say, I had so much fun last night.
0:51:44 I actually have a big project at work tomorrow that I was going to spend the majority of today on.
0:51:47 Let’s make plans for seeing each other later this week.
0:51:51 So you are creating that space for yourself.
0:51:55 You’re not assuming that they are a mind reader and they know that you don’t want to spend the day together,
0:51:58 but you’re basically stopping the problem before it starts.
0:51:59 I want to come back.
0:52:00 You said texting.
0:52:03 What are the rules around texting and dating?
0:52:04 What do you think the rules are?
0:52:05 I don’t know.
0:52:06 What are they?
0:52:07 Do you think you’re a good texter?
0:52:09 No, I don’t think so.
0:52:12 What do you think you could work on in your texting?
0:52:13 With anybody?
0:52:15 Or in dating, if you’re actively dating.
0:52:19 Just communicating better, I think.
0:52:22 I’m of an era where I don’t pick up the phone.
0:52:22 Okay.
0:52:28 And so, like, I think I’ve answered, like, five phone calls in the past, like, two years.
0:52:28 Really?
0:52:29 And they’re all from my mom.
0:52:30 We’ve had a phone call.
0:52:30 I know.
0:52:31 Was that shocking?
0:52:33 You know, unless it’s scheduled.
0:52:35 Like, if it’s unscheduled.
0:52:35 True, true.
0:52:37 I just don’t really answer the phone.
0:52:43 And I try to communicate over text, but sometimes nuance doesn’t come across.
0:52:48 I’m a visual person, so, like, when I make a joke, I usually, like, do something funny
0:52:49 with my face.
0:52:49 Yeah.
0:52:53 But over text, that can come off as, like, very dry or cold.
0:52:56 Because there’s no emotion attached to it.
0:52:57 No emoji sometimes.
0:53:01 It’s just, like, a dry, almost sense of humor or very pointed.
0:53:03 Are you a voice note guy?
0:53:04 Sometimes.
0:53:06 I do feel like that helps with sense of humor.
0:53:07 Yeah, totally.
0:53:08 So, it gets better.
0:53:09 But, like, what are the rules around text?
0:53:09 Yeah.
0:53:14 Like, and by rules, I mean, like, okay, if you’ve sent two texts and you haven’t got a reply,
0:53:16 like, are you, you got to wait?
0:53:17 Is it, like, there’s three?
0:53:18 Is it five?
0:53:19 Is it six?
0:53:21 Is it one for one at the start?
0:53:23 Like, what is the etiquette around this?
0:53:27 So, one of my favorite projects I’ve done over the last five years was a big Gen Z research
0:53:34 project at Hinge, where I followed this group of international Gen Z daters for around six months.
0:53:38 And one of the things that came out of it was this idea of digital body language.
0:53:41 The fact that we talk a lot about body language, right?
0:53:43 I’m sure this is something that you’ve thought about in your own life.
0:53:47 So, if I’m sitting forward, I am really interested in what you’re saying.
0:53:49 If I’m leaning back, I might feel defensive.
0:53:51 Am I averting my eyes?
0:53:56 And that your brain is subconsciously interpreting that as whether I’m a threat or whether I’m
0:53:57 interested in you.
0:54:04 And so, there’s a ton of digital body language, these unspoken cues as to my intentions.
0:54:09 And so, the hard part about digital body language is we don’t all interpret it the same way.
0:54:16 So, through this research, there was a woman, I remember, who said, if somebody says K instead
0:54:18 of O-K, then she thinks they’re mad at them.
0:54:23 And she’s like, specifically, I want them to say O-K-A-Y-Y-Y-Y.
0:54:26 Which is like, who would know that that’s what she wants?
0:54:27 But a K seems rude to her.
0:54:29 Oh, it’s just like, sure.
0:54:29 Sure.
0:54:31 If you say sure to somebody, oh my God.
0:54:34 If my sister says, got it, I’m like having a mini panic attack.
0:54:35 Yeah.
0:54:36 Because I’m like, you don’t got it.
0:54:37 You’re mad at me.
0:54:39 You’re just giving up on this conversation.
0:54:41 So, I think we all have versions of that.
0:54:47 But we did do research at Hinge looking at what are the most commonly agreed upon parts
0:54:48 of digital body language.
0:54:51 So, one of them is that actually the double text is okay.
0:54:56 So, if I text you and, you know, we’re early dating and I say, hey, I’d love to hear about
0:54:58 that show you were talking about.
0:54:58 How was it?
0:55:00 And then you don’t respond.
0:55:02 I might feel like, oh, he’s not interested.
0:55:04 I can never send another text.
0:55:08 But sending one more text that either like follows up on it or says like, hey, do you want to
0:55:09 go out this week?
0:55:10 People don’t mind that.
0:55:13 People are busy and they understand that sometimes messages get mixed.
0:55:21 Another one is one word answers are seen as very rude or curt or the person’s not interested.
0:55:27 So, if our text messages look like a lot of blue and a little bit of gray, there’s probably
0:55:28 a problem there.
0:55:32 And so, making sure that our messages seem pretty equal.
0:55:35 This is kind of going back to the idea of I take a step forward, you take a step forward.
0:55:37 Building the momentum together.
0:55:44 The other thing that comes up around text messages and might surprise people how often people talk
0:55:45 to me about texting.
0:55:50 But a common thing that somebody might say is, I hate texting.
0:55:52 I have a job where I keep my phone in my pocket.
0:55:53 I love deep work.
0:55:56 How can I tell somebody that I am interested in them?
0:55:58 I just don’t like texting.
0:56:03 Or the opposite, which is, I really love spending time with this guy in person, but he’s terrible
0:56:04 over text.
0:56:09 And so, the way that I’ve thought about it is, I think that you need to understand as a
0:56:14 person the maximum amount of text that you’re willing to give and the minimum that you’re
0:56:15 willing to take.
0:56:21 And if the minimum that you need is not within somebody’s maximum, you may not be a fit.
0:56:25 And it sounds so crazy because it’s like you’re really not going to date someone because of
0:56:26 your texting styles.
0:56:30 But look, that’s how a lot of people talk for a lot of the day.
0:56:36 And like, as parents, as busy people, it’s like, I’m texting with my husband more than
0:56:38 I’m really talking to him every single day.
0:56:43 And so, you need to have some overlap in your minimum and their maximum.
0:56:48 And so, you know, kind of a long-winded way of saying, I do think that texting styles are
0:56:51 really important since that’s such a big part of digital courtship.
0:56:57 And it’s really good to express to somebody what your texting style is and to maybe give
0:56:57 them a heads up.
0:57:03 Like, in the past, I found that sometimes people can’t read my tone over text just to
0:57:03 let you know.
0:57:08 Like, I’m not the biggest texter, but I will do my best to call you or just to make plans
0:57:10 and don’t read too much into my texting.
0:57:13 Okay, let’s come back to mind reading because you said that.
0:57:19 And I’ve always had the opinion, I would say until maybe the last year, that if somebody
0:57:25 knew me and liked me and wanted to be in my life, that they would be able to read my
0:57:27 mind and know exactly what I was thinking.
0:57:33 Talk to me about how that gets in the way in relationships and how we can be more comfortable
0:57:37 just telling our partner or prospective partner what we want.
0:57:42 It’s so funny because one of my closest friends in the world is a professional mentalist or
0:57:42 a mind reader.
0:57:45 And we lived together as roommates for a number of years.
0:57:49 And it’s just, I love the concept of mind reading.
0:57:51 And people would say, oh, you live with David.
0:57:52 Like, what’s it like?
0:57:54 Is he always reading your mind?
0:57:58 And I would say, if he was always reading my mind, he would unload the dishwasher a lot
0:57:59 more often.
0:58:05 And so I just think it’s so funny how there’s this sense of, well, we’re close and you know
0:58:07 me, so you must know what I want.
0:58:11 And that’s something that I’ve personally worked on a lot in my life.
0:58:17 So I’ve found that with a lot of my female friends, they get frustrated that their husbands
0:58:20 or partners didn’t give them what they wanted for their birthday of, why didn’t they know
0:58:21 I wanted a surprise party?
0:58:26 And what I’d say to them is, it’s much more important to get what you want than to have
0:58:30 the person guess what you want and then not get it right and be disappointed.
0:58:37 So I feel like I try to be really explicit with my husband and say like, hey, like for
0:58:39 Mother’s Day, like this is what would be a really great day for me.
0:58:44 And like, it’s not like he always delivers on that, but I’m kind of sharing what matters
0:58:44 to me.
0:58:51 Or I have friends, one guy is an economist and they have a pretty complicated system, but it’s
0:58:54 basically like when one of the people in the couple invites the other person to an event
0:58:59 at their work, they’ll basically say how much it matters to them on a scale of, you
0:59:03 know, zero to a hundred to basically say this invite, I care about it, 90 out of a hundred,
0:59:04 please come.
0:59:06 Or I care about it, 10 out of a hundred.
0:59:07 If you don’t come, it doesn’t matter.
0:59:14 And so I just think that if people get over this kind of romanticized idea of if you really
0:59:19 knew me, you’d know what I want into what I think is much more romantic, which is I feel
0:59:23 safe enough to tell you what I want and I hope that you’ll be able to honor it to the best
0:59:23 of your ability.
0:59:29 I have a theory that the people who expect unconsciously other people to be able to read
0:59:34 their mind, they do that because they’re very good at reading other people’s minds, but not
0:59:35 actually reading their mind.
0:59:41 They’re just, they tend to be maybe more thoughtful or they pay attention to a lot more nuance or
0:59:41 details.
0:59:42 Do you think that’s true?
0:59:45 I haven’t thought about that before, but it resonates with me.
0:59:52 Something that I’m working on with my business coach is I make a lot of assumptions about what
0:59:57 people want and then I get really nervous about saying something that I think will disappoint
0:59:59 them and then I just avoid the conversation.
1:00:03 But the feedback that I’m getting from my coach and from these people that I’m dealing with is
1:00:06 you’re actually getting wrong what I want.
1:00:10 And so by not having the conversation with me, you’re making decisions on my behalf.
1:00:15 And if you actually just told me what was going on, we could come to a happy medium about
1:00:15 it.
1:00:20 But because you think you know what I want and then you want to avoid discomfort for me,
1:00:21 you’re not even bringing it up.
1:00:26 And so I think for me, the work that I’m doing there is to have uncomfortable conversations
1:00:30 sooner instead of saying, well, I’m so good at knowing what everyone wants.
1:00:35 I must be right and instead being more curious and asking them what’s going on.
1:00:38 It’s kind of like a kind versus nice thing, right?
1:00:43 Like a kind person will tell you you have spinach on your teeth, but a nice person won’t.
1:00:45 Oh, I haven’t heard of that, but I do like that.
1:00:49 And I absolutely resonate with that where I always want to be the person who’s telling somebody
1:00:50 that there’s food in their teeth.
1:00:56 And rather than finding that it embarrasses people, I find that especially like a first meeting that
1:01:01 it really makes them feel closer to me because it’s like they feel comfortable enough to tell
1:01:03 me the slightly embarrassing thing.
1:01:05 Therefore, I am safe with them.
1:01:06 Yeah, I like that a lot.
1:01:12 I want to come to priorities in terms of life and dating, especially post, I don’t know, 30.
1:01:14 A lot of people are divorced.
1:01:15 Maybe they have kids.
1:01:17 Not in San Francisco.
1:01:19 I mean, fewer and fewer people have kids.
1:01:24 I just feel like it’s like, you know, in San Francisco, 30 and single and dating is kind
1:01:25 of the norm.
1:01:30 OK, so but I mean, you’re at a point in your life where you have a lot of competing
1:01:30 priorities.
1:01:36 You could make an argument at the risk of offending people that having kids younger is better because
1:01:40 you learn to be less selfish and that’s better for society.
1:01:42 And all of a sudden, the world’s not about you.
1:01:47 But if you go through your 20s, you can also make an argument that you tend to be more focused
1:01:53 on your career and you have priorities and dating has to fit into those priorities.
1:01:56 But it’s not the number one thing anymore.
1:01:57 How do you think about priorities in dating?
1:02:02 So many of the people that I work with are very career oriented.
1:02:06 These maximizers who are trying to strategize their way through life.
1:02:10 And oftentimes they come to me when they have been prioritizing their career for the last
1:02:15 12 years and then are like, oh, wait, I’m not where I want to be relationship wise.
1:02:21 And that’s why when I do get the opportunity to speak to younger people, I really encourage them start
1:02:22 prioritizing dating when you’re younger.
1:02:25 You have a more flexible lifestyle.
1:02:30 You have a bigger population of single people to choose from.
1:02:35 And, you know, in the last few years, as there’s been more and more layoffs, I feel like a lot
1:02:40 of people have had the reality check of this company that I dedicated 10 years of my life
1:02:44 to and that I missed a lot of dates because I had to travel for my job.
1:02:45 Guess what?
1:02:48 We were not in a long-term relationship.
1:02:52 We were in a 10-year-long relationship and now I’m single and I don’t want to be.
1:02:56 And so sometimes when I talk to people, it’s not just what do you want to add to your plate
1:03:01 a day to week, it’s what are you willing to take away from your plate in order to make time for that.
1:03:06 And so work is such a compelling system, right?
1:03:08 If I work harder, I get promoted.
1:03:10 If I get promoted, I make more money.
1:03:16 If I make more money, I get to have a nicer apartment and my mom gets to brag about me.
1:03:17 I get to update my LinkedIn.
1:03:24 It’s like it’s the perfect gamified system to find self-worth through achievement.
1:03:25 And dating is a lot harder.
1:03:27 There’s a lot of constant rejection.
1:03:29 It costs time.
1:03:29 It costs money.
1:03:31 It might take away from that gamified career.
1:03:38 And so I love to help people understand that the sooner you learn how to date, the sooner
1:03:39 you can stop dating.
1:03:43 And why not do that when you’re younger and there’s a larger pool of people to date?
1:03:48 Is there an age difference that it becomes too much?
1:03:54 You probably see everything at Hinge from like the 60-year-olds going for the 20-year-olds
1:03:56 to everything in between.
1:04:00 What’s an appropriate age gap that people should be looking for?
1:04:08 Most of my research has been with Gen Z and millennial daters who are sort of dating for their first
1:04:11 marriage or dating to have kids, depending on the situation.
1:04:14 That covers up to maybe 50, right?
1:04:19 Like, I mean, they’re younger, but their partner, the person that they’re looking for, might be older.
1:04:20 Potentially.
1:04:24 But what I was going to say is, you know, I did this Netflix show, The Later Daters, and
1:04:26 that was where I worked with people 55 plus.
1:04:30 And so that was sort of my first exposure to that age group.
1:04:36 And it was really interesting to see the different age differences and if people were dating somebody
1:04:38 at the same life stage as them.
1:04:43 And so I think what came up a lot on the show and in the kind of coaching conversations that
1:04:48 maybe didn’t make it onto the show was that sometimes if you look younger, you might go
1:04:49 on a date with somebody younger.
1:04:51 And that feels really good from an ego perspective.
1:04:53 But then you’re just in a different life stage.
1:04:57 And so I think what really matters is, do you have the same values?
1:05:00 Do you like spending time the same way?
1:05:04 You know, if you’re retired and you can travel and the other person is hustling and building
1:05:09 their business, then maybe you just aren’t a good match because you’re not going to be spending
1:05:11 the majority of your time together.
1:05:15 And so I think instead of like, you know, one of those funny calculations, like I don’t even
1:05:18 remember it, but it’s something like half of your age minus seven.
1:05:20 Like, I don’t believe in any rules like that.
1:05:22 I think people mature at different rates.
1:05:23 People have different life experiences.
1:05:28 But instead, really tuning into, am I dating this person because they’re younger and hotter
1:05:29 and an ego boost?
1:05:33 Or do I actually feel like this is somebody I want to partner with in life?
1:05:36 Okay, so we go on a first date.
1:05:36 We’re not interested.
1:05:37 What do we say?
1:05:43 We say in a text, probably, and not ghosting,
1:05:47 hey, it was really great to meet you.
1:05:52 It was so fun to hear about your podcast and the cool people that you’re interviewing this
1:05:52 year.
1:05:57 I don’t think we’re a romantic match, but it was great meeting you.
1:05:59 I don’t owe you feedback.
1:06:04 I don’t need to get into a long conversation about what you did right or wrong.
1:06:07 I’m acknowledging you that you’re a person.
1:06:09 We had an experience together, and I don’t want to move forward.
1:06:11 And that’s it.
1:06:11 You just leave it there.
1:06:12 Yeah.
1:06:16 I think the most important thing, kind of going back to your word of kindness, is to
1:06:17 be kind but firm.
1:06:21 So if you write back and say, I really don’t think I was my best self.
1:06:22 You know, I was kind of jet lagged.
1:06:23 I want to see you again.
1:06:26 You know, maybe that’s not what feels right for me.
1:06:28 And so I can respond or not respond.
1:06:33 But I feel like I did my duty by saying to you, I met you.
1:06:34 We had an experience.
1:06:35 I’m not interested.
1:06:40 And what’s so hard about ghosting, and it truly has become more and more common over,
1:06:46 say, the last five years that I’ve been tracking it, is that it leads people in this ambiguity.
1:06:50 Oh, maybe he likes me, but he just is busy and he hasn’t gotten back to me.
1:06:53 So I’m not going to get back to this person in case this person wants to see me.
1:06:59 And so in the research that I did on this at Hinge, what we found is that 86% of people
1:07:03 say, when it comes to rejection, I’d rather you tell me.
1:07:05 It hurts, but I want to know.
1:07:09 So you have this problem where people want the facts.
1:07:11 They want the truth so that they can move on.
1:07:15 But then the other people don’t share the truth because they say, oh, I don’t want
1:07:16 to hurt their feelings.
1:07:20 But you’re actually hurting them more by not being upfront from the beginning about how you
1:07:21 feel.
1:07:23 Do you block the person after you send this text?
1:07:26 I don’t think that’s necessary.
1:07:27 Do you block the person?
1:07:29 Well, I don’t know.
1:07:30 We’re going to come back to this maybe later.
1:07:31 Actually, let’s dive into this now.
1:07:33 A lot of people text their exes.
1:07:34 Yeah.
1:07:35 Is that healthy?
1:07:44 In general, the research shows that moving on from your ex is the best way to find a new
1:07:50 relationship because when we keep all of these doors open, it actually prevents us from finding
1:07:51 a new door to open.
1:07:55 And so if you have these five people from your past that you sleep with when you’re in a certain
1:07:58 city or you wonder, oh, maybe I should get back together with her.
1:08:01 I’ll keep her on the back burner, what we call like orbiting.
1:08:05 It can actually prevent you from focusing and finding somebody new.
1:08:08 And I even find this is especially true with sex.
1:08:13 So if you are somebody who craves a lot of sex, but you occasionally sleep with your exes,
1:08:18 you almost don’t have the motivation to find somebody new to be in a partnership with because
1:08:21 you’re getting some of those needs met by other people.
1:08:26 And what if you actually were dating in a different way where you’re like, I’m going to focus all
1:08:32 of my time, energy, really even life force on a new person because that’s aligned with
1:08:35 my goals versus just getting some of those needs met in the short term.
1:08:37 Well, let’s double click on that again.
1:08:41 So if your needs are getting met outside of a relationship, then there’s no incentive to
1:08:42 be in a relationship.
1:08:43 Is that what I…
1:08:48 You know, living in the Bay Area, there is such a big community of people who are polyamorous
1:08:49 or in open relationships.
1:08:53 And I’m personally not in one of those, but I see a lot of value in it.
1:09:02 I think that with the divorce rate being at 40% to 50% over the last 40 years, we’ve really
1:09:06 seen that this one-size-fits-all version of marriage doesn’t work for most people.
1:09:11 So if you have a product and 50% of people are returning it, then maybe you need to rework
1:09:11 that product.
1:09:16 So anyone who’s rethinking the structure of marriage, I am a fan of.
1:09:19 So relationship fluidity, all those things I think are great.
1:09:25 And so in a polyamorous relationship, you might have somebody where you have more of a sexual
1:09:27 relationship with them, somebody where you have more of an intellectual connection with
1:09:28 them.
1:09:29 There’s so many different ways of doing it.
1:09:34 And so I wouldn’t say that you need to get all of your needs met by one person and you
1:09:39 should not get those needs met by other people because I believe in these open relationship
1:09:39 structures.
1:09:44 But what I’m saying here is when you’re single and you have limited time and you really want
1:09:49 to find someone, ask yourself, is this ongoing relationship with my ex something that’s pushing
1:09:51 me forward or pulling me backwards?
1:09:56 And if the answer is that it’s pulling you backwards, then I would cut ties for the time being and really
1:09:59 focus on the next person that you could have a relationship with.
1:10:00 Interesting.
1:10:08 I have a friend who’s a GP and she’s mentioned in the past that one of the biggest reasons
1:10:13 that people come into our office for antidepressants is because they’re in an open relationship.
1:10:14 Really?
1:10:20 And they don’t want their partner to know that it’s causing them all this anxiety or all of
1:10:21 this.
1:10:23 And I don’t know if that’s true or not.
1:10:25 I mean, I’m personally not a fan of them.
1:10:25 Okay.
1:10:27 But I respect people.
1:10:29 Yeah, I do feel like your body language changed a little bit when I brought it up.
1:10:31 Oh, interesting on the body language.
1:10:33 But I’m all for people doing whatever they want to do.
1:10:34 Yeah.
1:10:38 You know, as long as everybody’s a consenting adult, like I’m in favor of it.
1:10:38 You’re not breaking the laws.
1:10:39 You’re not hurting people.
1:10:41 And everybody’s aware of the situation.
1:10:42 That’s fine.
1:10:47 I do wonder like what emotional toll it takes on people over time.
1:10:49 I’m very far from an expert on polyamory.
1:10:54 But I’m just thinking about one of my friends who’s very proudly polyamorous and kind of I
1:10:59 can hear her in my head sort of being like that person may not be a good fit for an open
1:11:00 relationship.
1:11:01 And why are they in one?
1:11:05 Because in an ideal world, there’s this concept of compersion.
1:11:06 Have you heard of that?
1:11:10 It’s a word that means I get pleasure when you get pleasure.
1:11:16 So like kind of the first polyamorous couple that I got to know about 10 years ago, I remember
1:11:22 the guy describing to me, oh, tonight my wife has a date with her boyfriend and I’m really
1:11:23 excited for her.
1:11:28 And like my anxious brain, my jealous brain was like, I cannot relate to that on any level.
1:11:29 That is a nightmare.
1:11:31 That’s instantly where my brain went.
1:11:31 Right.
1:11:36 And I think I’m just way too jealous and anxious and insecure of a person to really be a good
1:11:43 fit for an open relationship because I think that the part of my brain that would be thinking
1:11:44 about, am I going to be rejected?
1:11:45 Am I going to be abandoned?
1:11:51 Would just be so loud in my head that it would overcome any pleasure that I might get from having
1:11:54 my own relationships outside the marriage.
1:11:57 For other people, they are truly not there.
1:11:58 That’s not where the brains are.
1:12:05 I know people very intimately who feel like I’m so happy when my partner gets this other
1:12:06 need met.
1:12:09 Or maybe it’s like, I’m really busy at work right now and I’m not feeling that sexual.
1:12:12 I’m so happy that my partner has this outlet.
1:12:17 And so that story about the GP, I would say that doesn’t resonate with the experiences that
1:12:17 I’ve heard.
1:12:22 And it kind of goes back to why is that person in an open relationship in the first place?
1:12:25 Is it because they think that that’s the only way their partner should stay?
1:12:30 And probably instead of talking to the GP about it or maybe in addition, they should talk to
1:12:36 their partners and say, either this isn’t working for me or we need to change the stipulations
1:12:40 of this because it’s currently causing me more pain than it is pleasure.
1:12:45 Just thinking out loud, I wonder if it would feed the side of me that doesn’t feel enough
1:12:47 or doesn’t feel lovable.
1:12:51 And so it would just cause like this endless torment in my head.
1:12:54 That’s what I think it would feel like for me.
1:13:01 But I find polyamory really endlessly fascinating because it’s basically alerting me to a different
1:13:02 brain chemistry.
1:13:02 Totally.
1:13:06 And it’s sort of like in our society, we’ve accepted extroverts and introverts.
1:13:10 So like I know that I could be in a terrible mood and then go to a party and then have the
1:13:11 time of my life.
1:13:14 And it’s like, why was that party bringing me so much energy?
1:13:16 Well, I’m extremely extroverted.
1:13:17 For my husband, it’s the opposite.
1:13:23 So why can’t we all think there are people for whom compersion is possible and amazing
1:13:24 for them?
1:13:29 It’s okay that I’m not like that instead of this assumption that for everyone, they would
1:13:31 have the same experience around it.
1:13:36 And the other term that you mentioned that I’ve never heard of before is orbiting.
1:13:37 What does that mean?
1:13:38 Okay.
1:13:43 So orbiting is a term that a reporter from Mashable, Anna Iovine, came up with.
1:13:48 And it’s about this idea of keeping a bunch of people or several people in orbit around
1:13:51 you sort of to increase your opportunities.
1:13:56 So you’re sort of not committing to any of them, but they’re all there sort of on your bench
1:13:58 as people that you could interact with.
1:14:02 And instead of keeping all of these balls in the air, sorry, I’m like totally mixing metaphors
1:14:03 here.
1:14:08 It’s much better to commit to somebody, see how the relationship goes, then decide if
1:14:13 you want to stay in the relationship or not, and then move on versus feeling like, well,
1:14:18 the more possibilities I have, the more freedom I have, the more chances of success I have.
1:14:24 Actually, success comes from committing to something, seeing if it works, and then moving on if it
1:14:24 doesn’t.
1:14:28 There’s so many parallels between that and business, right?
1:14:32 Where, you know, a lot of people just tend to dabble in all of these different projects
1:14:37 and they don’t actually get things done versus people who commit to a project, focus on it
1:14:39 and make it a priority.
1:14:43 There’s a great concept from Dan Gilbert of Harvard called changeability.
1:14:50 So we often crave the ability to change our minds because it makes us feel more free.
1:14:55 So in this experiment that he ran on the Harvard campus, he had a bunch of students take a
1:14:56 photography workshop.
1:15:01 And one of the weekends that students took the workshop, they would get a call at the
1:15:05 end of the weekend and say, hey, we’re actually going to have an art show in London in a few
1:15:05 weeks.
1:15:11 Pick one of your pictures from this weekend of taking pictures, and that’s going to be sent
1:15:11 to London.
1:15:14 And they didn’t have the opportunity to change their mind.
1:15:19 In a different scenario, they would call the students and say, pick one of the pieces to
1:15:23 be sent to this art show in London, and I’m going to call you in a few days and see if
1:15:23 you want to change your mind.
1:15:27 Most of the time, people didn’t change their mind about the photos.
1:15:33 But when you ask people in which situation they were more satisfied, the people who didn’t
1:15:38 have the chance to change their mind were actually more satisfied because they made a commitment
1:15:41 and they immediately rationalized it and they felt good about it.
1:15:46 When you can change your mind, you start wondering, well, that picture is a little sharper,
1:15:50 but this one’s a little more original, and maybe people in London will like this one
1:15:50 more.
1:15:54 And so you sort of start making this pro-con list in your head that actually works against
1:15:57 you because you start doubting your original answer.
1:16:02 But this comes back to almost what we were talking about earlier in dating multiple people and
1:16:03 having all these options available.
1:16:07 And you’re sort of like, oh, I’m making these choices all over again every day.
1:16:08 Absolutely.
1:16:10 And that’s something that Hinge is thinking about.
1:16:14 So my favorite feature that’s come out in a long time is this thing that came out last
1:16:16 year called Your Turn Limits.
1:16:20 And basically, the idea is that people were thinking, I want to get as many matches as
1:16:20 possible.
1:16:24 I really want to get this ego boost from attention and see how many people will like me.
1:16:27 And instead, it’s about connection over attention.
1:16:33 So now, if you have eight conversations where you owe somebody a response, you cannot match with
1:16:36 anyone else until you respond to one of those people.
1:16:41 So either you close out the conversation and show that you’re not interested or you keep
1:16:42 the conversation going with them.
1:16:47 And I was with my cousin over Christmas and he was like, oh, Logan, like this feature is
1:16:47 so challenging.
1:16:49 Like, I’m just trying to meet some new people.
1:16:51 And I’m like, dude, look at your matches.
1:16:52 Who are these women?
1:16:53 Do you like them?
1:16:55 Then ask them out on a date.
1:17:00 And I think that in general, the brain just has such a natural tendency to want options and
1:17:03 choices when in reality, limiting those options or going through things
1:17:06 one at a time makes it much easier to make a choice.
1:17:11 And so I think in the age of dating apps, having this your turn limits feature is actually
1:17:17 a really smart way to kind of nudge people towards making decisions instead of endlessly
1:17:18 trying to match.
1:17:24 And then once you’ve had a date with somebody, what does the science say about whether you
1:17:28 should, should I be dating three people at once for a first date or should I date one
1:17:31 person and then be like, oh, I kind of like this person.
1:17:35 I’m going to like pause the app or like hide my profile or whatever it is.
1:17:37 I found that it does differ by person.
1:17:40 So there are people out there that are really anxiously attached.
1:17:43 And when they meet someone, their brain goes into, I need to lock it down.
1:17:44 I don’t want to date anymore.
1:17:45 So I just want to date them.
1:17:47 So how can I become exclusive with them?
1:17:51 And for those people, sometimes having multiple people that they’re seeing in the beginning
1:17:56 is actually a way to sort of ease some of that and just makes it a little bit easier for them
1:18:00 to be a bit more relaxed and have a bit more of an abundance mindset.
1:18:04 There are other people for whom seeing multiple people at the same time in the beginning either
1:18:08 feels immoral or uncomfortable or just too exhausting.
1:18:13 And so I would say for the person, really explore what are the patterns that have held you back in
1:18:18 the past, what feels hard for you, what makes you feel like you’re dating successfully,
1:18:20 and then do what’s right for you.
1:18:24 While, of course, keeping in mind things like making it clear to someone if you’re not exclusive
1:18:25 or if you’re not sexually exclusive.
1:18:30 How do you have that conversation on maybe your first date or your second date?
1:18:34 Do you just ask outright, like, hey, are you dating other people?
1:18:35 Like, how do you bring that up?
1:18:40 I would say that in modern dating, it’s sort of assumed that you’re not exclusive
1:18:42 until you have the conversation.
1:18:47 And that pain can come from somebody making an assumption, well, oh, we’ve been dating for six
1:18:48 months, we must be exclusive.
1:18:51 Oh, we’ve had sex, we must be exclusive.
1:18:56 And there is a lot of heartbreak that happens when people don’t have that explicit conversation.
1:19:02 So in life, in relationships, in dating, I am such a big fan of just checking in with the
1:19:07 person because there’s really this natural tendency, kind of going back to mind reading
1:19:12 of, well, if I really like you, then we must think the same way and be on the same page.
1:19:16 And when you bring it up, you’re afraid, well, what if I find out information that makes me
1:19:17 sad, then I’ll be sad.
1:19:22 It’s like, no, that information is power and you need the data to make an informed decision
1:19:23 for yourself.
1:19:28 And if you find out information that’s disappointing, yes, it hurts, but now you can decide if that’s
1:19:29 the right person for you or not.
1:19:33 What are women not getting from men and men not getting from women?
1:19:37 That’s a question that I’m going to be researching more this year.
1:19:38 So stay tuned.
1:19:39 But it’s really on my mind.
1:19:40 What’s your intuition?
1:19:49 I don’t know if it’s gender specific things where there’s a lack of connection or just maybe
1:19:55 cultural things going on where, you know, there’s big differences in religious institution
1:19:57 attendance or political divergence.
1:20:04 But when I think about the issues in dating, I tend to focus less on what is this gender
1:20:05 or that gender think.
1:20:09 And I tend to focus more on patterns of behavior or blind spots that people have.
1:20:14 And so, of course, there’s going to be different advice that I give to a woman in her late 30s
1:20:17 who wants to have biological children versus a guy in his 20s.
1:20:20 Like those conversations sound different and they have different timelines.
1:20:25 I think so much of the work that I do is really about helping people understand who
1:20:28 they are, understanding these patterns, holding them back.
1:20:30 And those are sort of universal things.
1:20:34 But I am interested in what’s happening in dating right now.
1:20:39 And I am sort of at the beginning of a research project that will dig more into sort of what
1:20:41 are certain groups not understanding about other groups.
1:20:46 What makes somebody good at dating and maybe bad at being a partner?
1:20:48 And then the opposite.
1:20:51 What makes somebody bad at dating but like good at being a partner?
1:20:53 What do you think you are?
1:20:57 I think I’m terrible at dating but good at being a partner.
1:21:00 What do you think makes you bad at dating?
1:21:03 I get bored.
1:21:10 The opportunity cost of being on a first date is incredibly high.
1:21:11 Okay.
1:21:12 So going back to priorities.
1:21:13 Yeah, yeah, yeah, yeah.
1:21:15 Like if you think about my priorities, it’s sort of like the kids.
1:21:16 Okay.
1:21:17 And then work.
1:21:20 And those two things matter a lot to me.
1:21:24 And between those two things, it doesn’t leave a lot of time for anything else.
1:21:28 And the difference between running a business and working for somebody else often is I could
1:21:31 be working and earning money like you at 6 p.m., right?
1:21:35 So if I’m on a date or something with somebody, then there’s all these things.
1:21:37 And you start thinking about that.
1:21:43 And then you just get caught up in your day sometimes and you’re extremely focused, which
1:21:46 is part of what makes people successful is extreme focus.
1:21:50 And then I think, and I don’t know if I’m right or wrong, correct me on this.
1:21:55 If you come home to a person, I value connection.
1:21:56 I value that time.
1:22:02 But it’s really hard to make that time in your day versus it exists naturally because
1:22:05 you’re coming home, you’re going to bed, you’re cleaning the kitchen together, you’re
1:22:09 making dinner together, you’re doing these things together, which becomes a natural part
1:22:12 of your day versus I’m not going to text you.
1:22:15 And I’m like with the kids and I’m making dinner and I’m not going to.
1:22:15 Yeah.
1:22:17 And so by that time, it’s 9 p.m.
1:22:19 And I don’t know about everybody else, but 9 p.m.
1:22:20 I’m pretty much ready for bed.
1:22:23 You know, maybe 10, I can go up till.
1:22:25 But how does that work?
1:22:27 And maybe this is the wrong way to think about it.
1:22:27 I don’t know.
1:22:32 It’s very interesting that you said you’re good at being in a relationship, but sort
1:22:34 of not as good as getting into one.
1:22:35 Yeah.
1:22:40 And it sounds like once somebody has jumped through the hoops necessary to kind of make
1:22:44 it into the top priorities in your life, you will give them the time and attention.
1:22:50 But you find that hard to do in the early stages where maybe they haven’t earned that spot yet.
1:22:50 Totally.
1:22:51 So.
1:22:55 I mean, that’s a bit more extreme than I would word it, but I think you’re generally
1:22:56 on the right track.
1:23:00 And so what are your long-term goals in dating and relationships?
1:23:02 I want to be in a relationship.
1:23:02 Yeah.
1:23:07 You know, I want to be happy and I want a life post my kids.
1:23:12 Like right now, one of the things that’s top of mind for me or has been for a while is sort
1:23:14 of the kids.
1:23:15 They’re 14 and 15.
1:23:20 The path to them going to university is very clear.
1:23:21 And then what?
1:23:23 I have a great, amazing group of friends.
1:23:26 I’m very close with my family.
1:23:27 I have a very full life.
1:23:28 But then what?
1:23:31 They move out and now I’m alone.
1:23:37 The reason why I asked you what your long-term goals are, are that if you’re really clear
1:23:41 on your goal, I think it helps you prioritize your life differently.
1:23:48 So it’s like for the next five years, as you have kids at home, it’s very clear what your
1:23:49 evenings look like.
1:23:49 Totally.
1:23:52 So what happens when you don’t have any kids at home?
1:23:54 Do you then suddenly start dating?
1:23:55 And then do you feel behind?
1:23:58 Do you feel like I’m a little rusty on my dating skills?
1:24:00 I don’t know what kind of person I like.
1:24:03 I actually wanted to have more kids, but now I feel like I’ve aged out of that.
1:24:09 And so by getting super clear on your long-term goals for you, for anyone else, I feel like
1:24:11 it helps you make those adjustments in your life.
1:24:19 And so if you told me, I want to run a marathon, but I don’t have time to train, then I would
1:24:21 say, I don’t really think you want to run a marathon.
1:24:22 Totally.
1:24:24 Or you’re not going to run a marathon this year.
1:24:29 But if you said, I really want to run a marathon and I’m willing to lose an hour of sleep every
1:24:36 night or be slightly worse at my job or even have a few fewer hours a week with my kids,
1:24:39 and I would say it sounds like this is something that you’re willing to do.
1:24:43 And so instead of thinking, this is something that will happen in the future, I think it
1:24:48 does look like making, sacrifice is too strong a word, but making adjustments now to how you
1:24:55 spend your time so that you are getting close enough to somebody to even decide if you want
1:24:56 to be in a relationship with them.
1:24:58 Dating is a bit of a show though.
1:25:00 Like you put on your best face, right?
1:25:01 You might’ve had a bad day at work.
1:25:06 You sit down and all of a sudden you just want to be in your sweatpants at home watching
1:25:07 trashy TV.
1:25:10 But you’re doing something that you don’t want to do.
1:25:14 And so like, not not want to do, but you’re putting on a bit of a mask, right?
1:25:16 You’re hiding part of yourself through dating.
1:25:22 And I feel like it might be better if people just saw all the different sides of you rather
1:25:24 than this pretend little dance.
1:25:25 So what would that look like?
1:25:27 I don’t know.
1:25:28 Like you’re the expert.
1:25:36 No, but why I’m pushing you on that point is like, your job right now is flying to different
1:25:40 locations to have deep one-on-one conversations with somebody.
1:25:42 Isn’t that a little bit of a show?
1:25:44 Isn’t it a little bit like a first date?
1:25:45 It’s like, I’m meeting a stranger.
1:25:47 I want to have a connection with them.
1:25:48 I want to have an experience.
1:25:51 There’s cameras here, but I don’t think we’re thinking about the cameras.
1:25:56 I think we’re thinking about the fact that we are getting to know each other, exchanging
1:25:56 information.
1:25:59 And that’s why I prefer to do them in person.
1:25:59 Right, me too.
1:26:03 So my assumption is that like, you must enjoy this if you’ve built a life around it.
1:26:08 How can you reframe dating to be something where it’s like, I get to meet somebody, have
1:26:13 an experience with them, go deep, have thoughts I’ve never had before because we’re playing a
1:26:18 conversational game of ping pong and I’m having a good time.
1:26:21 Whereas right now it sounds like the frame is, dating is draining.
1:26:23 Dating is time away from my kids.
1:26:29 Dating is I can’t be in my sweatpants as opposed to reframing it to this is aligned with my goals
1:26:30 and I can actually make it fun.
1:26:34 Maybe the way to think about this is I feel broken in a lot of ways, right?
1:26:39 And this is part of the reason I went to therapy last summer and spent a lot of time.
1:26:41 I did immersive therapy, which is kind of crazy.
1:26:42 Oh, tell me about it.
1:26:46 I spent like 10 hours a day with this woman who like flew to Ottawa.
1:26:47 Cool.
1:26:48 And we walked.
1:26:50 We walked like 20 miles a day.
1:26:50 This is like my dream.
1:26:52 For five days.
1:26:53 Oh my God.
1:26:53 That’s healthy.
1:26:54 That sounds great.
1:26:57 And by the end of the day, she’s like totally energized and I’m like, oh my God, I’m ready
1:26:58 for sleep, right?
1:27:00 Okay, this is a new modality that I need to pursue.
1:27:01 It was amazing.
1:27:02 It was the best thing ever.
1:27:06 I didn’t want to do this like every two weeks thing and I definitely didn’t want to do therapy
1:27:06 over Zoom.
1:27:07 I love this.
1:27:13 So I hired this world-class therapist, flew to Ottawa, and spent like four or five days with
1:27:13 her.
1:27:14 Incredible.
1:27:15 Totally immersed.
1:27:20 And I figured, you know, from my point of view, the worst thing is like she knocks on the door,
1:27:21 we don’t get along.
1:27:26 I’ve already paid for the week, you know, it’s sort of like just go home and I’ll do
1:27:26 work or whatever.
1:27:28 But we really hit it off.
1:27:34 And part of what came out of this is, I don’t know, maybe I’m alone in this, but I feel like
1:27:39 when I get broken up with where a relationship doesn’t work out, I feel like I’m constantly
1:27:41 telling my friends, oh, it didn’t work out.
1:27:46 And then there’s a part of me on the inside that just feels like I’m broken.
1:27:48 What’s your reaction to that?
1:27:50 That you are so not alone.
1:27:52 Rejection sucks.
1:27:57 Having somebody spend time with you, evaluate you, and tell you that you’re not what they
1:27:59 want is so painful.
1:28:03 And I think that if you apply for a job and you don’t get it, it’s, oh, I wasn’t right
1:28:06 for the position and they had an internal candidate.
1:28:07 It’s just one slice of your life.
1:28:13 There’s something uniquely painful about rejection in dating because it’s like, I’ve met you and
1:28:14 I don’t want you.
1:28:20 And so I’m just validating that I think many, many, many people find this whole process very
1:28:25 painful, especially people who’ve been dating 10, 15 years and are just like, my body, my soul,
1:28:27 I can’t go through this anymore.
1:28:29 So I just have a lot of empathy for that.
1:28:35 But what is so interesting about the conversation that we’re having is you sort of started with,
1:28:41 it’s hard for me to make time for dating when I think what’s actually going on is it’s very
1:28:43 painful for me to feel rejected.
1:28:45 So I don’t want to subject myself to that.
1:28:50 And so the time is an excuse for a much deeper thing that you’re experiencing.
1:28:52 There’s definitely an element of that.
1:28:54 I feel broken even when I break up with somebody.
1:28:56 Do you know what I mean?
1:29:02 Like, I feel like maybe I pushed them away or did something to like cause the fracture and then,
1:29:06 you know, eventually manned up and called off the relationship or something.
1:29:11 But then I walk away from that feeling like I’m like, why did I do that?
1:29:14 So what’s the story in your head?
1:29:18 I mean, it comes back to vulnerability at a point, right?
1:29:23 Like, I think you get to a point in any relationship where you have to make a decision.
1:29:27 And for me, it’s more binary maybe than other people.
1:29:31 And that decision is, do I trust this person to not hurt me?
1:29:37 And for whatever reason, post-divorce, that’s been really hard for me to get to that point.
1:29:39 And then trust somebody.
1:29:44 So when I have got to that point and I do overcome it, it hasn’t worked out.
1:29:45 And so it’s like, oh, gosh.
1:29:48 So you did these five days of immersive therapy.
1:29:49 Oh, yeah.
1:29:55 What are you currently doing to kind of heal that inner wound, which is I am broken?
1:30:04 Because if your analysis is that until you feel less broken, both when you break up with someone and when they break up with you,
1:30:06 I think you’re not going to be able to connect with someone.
1:30:10 Walk me through how you made your decision about your husband.
1:30:13 Because that was not a love at first sight.
1:30:13 Yeah.
1:30:15 That was a slow burn.
1:30:22 How do you decide between falling into a relationship with inertia and choosing to be in a relationship?
1:30:26 Thank you for indulging me and letting me talk about my husband, who I love so much.
1:30:34 And it’s so cliche, but I feel like I love him way more now than I did in our first year, our second year.
1:30:36 Our lives are just so much more enmeshed.
1:30:41 And so my husband and I met in college.
1:30:44 And we only know this because we became Facebook friends at the time.
1:30:48 So I have this vague memory of sitting next to him in the dining hall.
1:30:49 And we had a mutual friend.
1:30:53 And he wrote on my Facebook wall, which back in the day, you know, maybe he was flirting or maybe he wasn’t.
1:30:57 And then we met again at Google.
1:31:01 And I saw him on a dating app.
1:31:04 And I looked at his photos.
1:31:07 I can just remember exactly where I was, exactly what the photos looked like.
1:31:08 And I swiped left.
1:31:13 I said no, because from his pictures, he just looked like this unsmiling bro.
1:31:18 They were sort of all from this like one hiking trip and maybe one wedding he went to.
1:31:19 Wasn’t smiling in any of them.
1:31:24 And I was just like, oh, this guy’s like wearing tank tops and a backwards hat, like not for me.
1:31:32 And I like that part of the story because I think it shows like how quickly we make judgments and how incorrect a lot of those judgments are.
1:31:42 So then some period of time later, I held this lunch at Google, which was people who had gone to our college who worked at Google.
1:31:46 And, you know, in retrospect, I think I was expanding my network.
1:31:48 I was doing it for the interns from our school.
1:31:52 But it was also a way of just like meeting more people and maybe meeting more potential partners.
1:31:56 And so I sat next to my then husband at this lunch.
1:32:03 And I was talking about how I was trying to learn the statistical programming language of R and how it was very hard.
1:32:08 And he said, oh, I just dropped out of a math PhD program where I wrote R every day.
1:32:11 I will tutor you in it.
1:32:17 And now that I know this person extremely well, I feel like that was out of character for him.
1:32:19 He was totally like hitting on you.
1:32:23 Like I think he must have been, but that’s not like what either of our versions of it are.
1:32:24 He didn’t like-
1:32:25 It’s not how it felt.
1:32:27 It’s not how it felt, but it’s so interesting.
1:32:38 It’s like even using my language of what side of you does the person bring out, I feel like in that moment, I brought out a generous side of him that he maybe doesn’t always access.
1:32:42 My husband is not the person going through the world asking people if he can do them favors.
1:32:49 And I don’t know if it even was romantic for him or a feeling of like, I want to be around this person more or like, I’m lonely.
1:32:51 I just dropped out of a PhD program.
1:32:52 I want to make new friends.
1:33:00 And so over the next year, we did have these R tutoring sessions and I remember them so well.
1:33:06 And I remember these like celebratory moments where I’d figure things out and he was a good tutor and it really put him in a good light, right?
1:33:07 Like he’s just so smart.
1:33:09 It was a chance for him to chime.
1:33:16 At the same time, there was this guy that I had met at Burning Man who I was obsessed with and definitely pursuing.
1:33:23 And every textbook example of anxious attachment was coming true for me.
1:33:26 So it was like he would pull away, so I would chase him more.
1:33:33 He rejected me, so I thought, how can I prove to him that I’m worthy of his love?
1:33:37 This guy who I was obsessed with, I had a mutual friend with him.
1:33:44 We were sort of in the same extended group of friends and somebody who knew the guy that I was chasing, you know, was just witnessing how in pain I was and was like, hey, like this isn’t working out.
1:33:56 And so I started seeing this dating coach and it was so helpful because a lot of what we did was kind of pull back the curtain.
1:34:04 And so I started to understand when she asked me, the person who you’re going to end up with, how do you want them to make you feel?
1:34:07 And so a lot of that stuff was I want to feel desired.
1:34:08 I want to feel smart.
1:34:10 I want to feel cared for.
1:34:13 And how does this guy from Burning Man make you feel?
1:34:14 Well, he makes me feel anxious.
1:34:17 He makes me feel not good enough.
1:34:19 He makes me feel not attractive enough.
1:34:26 And it’s like in continuing to pursue him, I was continuing to pursue those feelings that felt really bad.
1:34:31 She said, well, do you know any guys, have you ever dated anyone who makes you feel this way that you want to feel?
1:34:35 And this guy from work popped up in my head.
1:34:37 I was like, wow, those tutoring sessions are really fun.
1:34:41 And we’ve gotten closer and now we have lunch at work.
1:34:44 And sometimes I call him after my dates with other people.
1:34:47 But why am I not dating him?
1:34:54 And so pretty quickly, you know, being a goal-oriented person, I was kind of like, hey, I don’t have plans this Friday night.
1:34:57 Like, you know, dot, dot, dot, you should ask me out.
1:35:01 And we quickly went on a first date and, you know, a number of dates.
1:35:06 And now we’ve been together for almost 10 years.
1:35:12 And I just feel like on paper there were some reasons why we wouldn’t have worked.
1:35:20 So, for example, like at the time I was very into Burning Man and he not only didn’t go but he would say, I don’t really trust anyone who goes to Burning Man.
1:35:21 Well, guess what?
1:35:23 We went to Burning Man together multiple times.
1:35:35 It’s like I felt like the deepest parts of us that were connected, so sort of same sense of humor, which is a huge part of a relationship, mutual intellectual respect, really trusting each other deeply.
1:35:39 Like, those things were there from the beginning and have continued to grow.
1:35:43 And we still have parts of our lives where we’re not the same.
1:35:44 He’s vegan and I’m not.
1:35:47 I like traveling a lot more than he does.
1:35:52 But we’ve built a life where the Venn diagram of the middle is super strong.
1:35:59 And we each also have the parts of our lives that are separate and we’re not trying to be 100% merged.
1:36:02 What was the transition from friendship to dating?
1:36:03 Was it seamless or was it awkward?
1:36:16 You know, I think in my head it’s so mythologized that, like, I don’t know if I can give you a truly honest answer, but I think it was kind of pouring gasoline onto, like, the chemistry that we already had.
1:36:20 Yeah, so it was, like, it was really exciting.
1:36:24 I mean, it felt so exciting, like, especially, you know, we’ve worked, both worked at Google.
1:36:26 It’s this big company with thousands of people.
1:36:36 So I would go to his cafe instead of my cafe and, like, hope that I would see him or, like, you know, I would, what did we call it back in the day, like, G-chat him, like, on the shuttle.
1:36:44 Like, there was just so much excitement in the beginning around, like, wow, like, I have a lot of chemistry with this person and we’re going to take that friend chemistry
1:36:47 and see if there’s something romantic there.
1:36:50 And it was not smooth sailing all the way.
1:36:59 Like, there was definitely a moment a few years later where I kind of blew up my life where I left this steady job that I had at Airbnb and I moved to New York for a few months to do this TED program.
1:37:02 And just a lot of changes were happening.
1:37:06 And we definitely hit a moment of, like, we’re either going to break up or get engaged.
1:37:10 And we navigated that moment and, you know, clearly—
1:37:11 How did you navigate that moment?
1:37:16 That is, like, such a decision where there’s a fork in the road.
1:37:16 Absolutely.
1:37:17 You’re in a relationship.
1:37:17 Yeah.
1:37:20 You have a lot of sunk cost in a relationship.
1:37:22 How did you make that decision?
1:37:29 I think people often assume that relationships are smooth sailing and that you just keep dating until you’re married.
1:37:48 But as somebody who does these, like, breakup consultations and has really talked to a lot of people over the years, that idea of break up or get engaged is pretty common because it’s like we either keep going and it escalates to marriage soon or there’s no marriage at the end of this, in which case we should break up because we both want to find other people to marry.
1:37:54 And so I think just, like, normalizing that that happens or that people put ultimatums or deadlines on things.
1:37:55 I actually think that’s happening all the time.
1:38:01 For us, it was a lot of conversations about things that we wanted long term.
1:38:07 So, for example, one of the conversations that we had was I said, like, here are three values of mine.
1:38:11 I really like travel and I want to travel more with you.
1:38:18 I want you to get to know my friends better because my friends are so important to me and I want those people to really know you and vice versa.
1:38:24 And I probably want to live in community at some point and I want to know if you would be open to that.
1:38:31 And now, six or seven years after that conversation, it’s like we’ve done a ton of international travel together.
1:38:38 Most of my closest friends are his closest friends and we lived in this amazing communal environment for two and a half years during the pandemic.
1:38:41 And so my husband is super stubborn.
1:38:42 He’s super independent.
1:38:44 It’s not that he changed himself.
1:38:51 It’s that he understood things that were important to me and he was able to give them to me in a way that felt genuine.
1:38:58 And there’s plenty of things that I’ve done over the years such as, you know, I’m not vegan but, like, there’s not a lot of meat in our home.
1:39:02 And, like, I’m closer to that or we’re currently raising our daughter to be vegan.
1:39:10 And so I just feel like we just kept finding that our values were aligned and that we loved hanging out together.
1:39:13 And, like, I can’t even emphasize enough this idea of mutual trust.
1:39:19 Like, it’s almost annoying to think about it but it’s like I think my husband’s right most of the time.
1:39:21 And I think he’s right about really big issues.
1:39:32 And so I feel so lucky that I have this person as my decision-maker partner where I can really say, like, I have this opportunity.
1:39:33 This is how far away it is.
1:39:35 Do you think I should do it?
1:39:42 And when we talk through it at the end of the conversation, like, I either agree with him or he’s helped me come to the right decision for myself.
1:39:48 And when people have partners where they don’t really trust or admire or respect them, like, I couldn’t be in that relationship.
1:39:52 And so I think that as parents, you’re just constantly making decisions.
1:40:03 And that’s why I feel even closer to him than ever before because I’m like we’re really basically partners in this big class project and it’s been really fun.
1:40:03 That’s awesome.
1:40:12 Do you agree with the time boxing or the ultimatum, I guess, as you called it or sort of like these points where you artificially create this?
1:40:18 One point for people who are not younger and maybe dating again is do you meet the kids?
1:40:27 Yeah, so I think that the ultimatum, I mean, that term is even loaded at this point because there’s like this Netflix show about the ultimatum.
1:40:32 And I think when people hear that, they probably have a negative assumption of somebody being like, if you don’t propose by the end of the year, we’re breaking up.
1:40:34 Like, that doesn’t sound collaborative to me.
1:40:40 But I actually do think that decision points are very important in life and in relationships.
1:40:45 So there’s this great research about, you know, people eating cookies.
1:40:52 So, like, in one part of the experiment, people just eat cookies in a sleeve and they just eat the whole sleeve of cookies until it’s over.
1:40:54 And then they’re like, damn, I just ate a lot of cookies.
1:41:00 In another part of the experiment, in between every few cookies are these colored pieces of wax paper.
1:41:05 And when you get to the piece of colored wax paper, you think like, do I want to keep going or not?
1:41:10 And it creates a decision point that makes you consciously decide, do I go forward or not?
1:41:14 And so I think that relationships do offer these decision points.
1:41:16 Do we want to be exclusive?
1:41:18 Do we want to move in together?
1:41:19 Do we want to get married?
1:41:21 Do we want to have kids?
1:41:25 And each of those is an opportunity to check in with the other person.
1:41:37 And so sometimes creating that by saying, hey, let’s go away for a weekend and talk about our future, you’re really shining a light on an important topic that impacts both of you.
1:41:42 And so maybe I’ll take back the word ultimatum and instead say, I want people to make conscious choices.
1:41:47 I want them to be deciding, not sliding through relationship transitions.
1:41:56 How do you have those hard conversations in a secure way where a lot of people might interpret them as like, oh, no, the relationship’s over.
1:41:57 They close up.
1:41:58 They get defensive.
1:42:03 How do you structure them in a way where both people stay open and they’re trying to solve the problem together?
1:42:08 It’s like we have a problem or we have a decision point, but we’re both on the same side of the table.
1:42:14 How do we deal with this versus the perception that one person might have that, oh, God, it’s over.
1:42:16 I’m going to start protecting myself.
1:42:20 And the minute they do that, it becomes almost a self-fulfilling prophecy.
1:42:23 So there’s definitely people who are more experts on this than I am.
1:42:36 Like a lot of people love Marshall Rosenberg who wrote Nonviolent Communication or even I think some of the work by different negotiation experts is really helpful because you say, how can we solve this together?
1:42:40 So I would really encourage people to seek out those resources.
1:42:47 But some of the things that I can say are really approaching things from being a team.
1:42:51 So we as a team are thinking about our financial future.
1:42:57 And this is, you know, I don’t know if you know Ramit Sethi, but sort of some of Ramit’s work where it’s like, what is our rich life?
1:43:02 Let’s sit down together and have a fun, generative conversation around our rich life.
1:43:08 And isn’t that fun to think about what we could achieve together versus, hey, I save a lot more money than you do.
1:43:10 I don’t want your debts to be mine.
1:43:11 It’s like we’re adversaries.
1:43:18 And so how can you come at it from a place of we get to do this really exciting thing of design our lives together.
1:43:24 Let’s have a conversation about it versus this is a negotiation where one of us wins and the other loses.
1:43:28 There’s no one size fits all, but how do you – money is a great point, right?
1:43:36 But like how do you have those conversations when maybe there’s a huge income gap or do you have a joint account or do you have separate accounts?
1:43:37 And how does that work?
1:43:41 Does having a large income gap correlate to problems in a relationship?
1:43:45 I truly do pull on Ramit’s work for a lot of this stuff.
1:43:51 You know, he has this great podcast where he interviews couples and money and he has a new book, Money for Couples.
1:43:57 And I just did a newsletter with him where it was about how to have the first money conversation.
1:44:01 And some of the key tips are things like it’s the first conversation.
1:44:03 It’s not the only conversation.
1:44:08 So maybe it’s just where you open up and you talk about what does money mean to you?
1:44:10 What was your family’s relationship with money?
1:44:13 When you think about money, what feelings does it evoke?
1:44:24 And so just having a conversation where more people are sharing versus having a conversation that needs to come to a specific outcome like, well, I make two times what you make, so I should pay two times the rent.
1:44:28 It’s like you don’t have to get into all the tactical stuff right away.
1:44:42 I think approaching it as the first of one of many conversations is a really healthy idea because I just went to this event that Ramit had and he said a lot of times people don’t even know what somebody else makes or how much money they have.
1:44:47 You know, until something like having a kid or, you know, buying a house.
1:44:53 And it’s like we should be having conversations about sex, money, spirituality, children a lot earlier.
1:45:02 I like that politics has become very divisive in the last, I don’t know, 10 years, let’s say.
1:45:06 What’s the difference between having different political views and a deal breaker?
1:45:12 It’s been so interesting in the 10 years of doing this to see how this has changed.
1:45:25 So 10 years ago, I did an event with Christian Rutter, one of the founders of OKCupid, and we talked about this question that they have on an OKCupid survey of, you know, do you care about politics?
1:45:33 And what he told me at the time was it was way less important if the person had the same political views as you as if they cared about politics or not.
1:45:44 And now, fast forward to this year, I would say that’s no longer the case, that people really do care about political views because it’s moved into the category of values.
1:45:50 And so people are really thinking about if we share political views, that’s a proxy for do we share values.
1:45:55 And so for a lot of people, it’s as important or more important to them than something like religion.
1:46:02 And so at the end of the day, it’s about understanding what really matters to you in your life, what really matters to you in a partner.
1:46:07 And if politics are something that’s at the top of that list, I think that that’s a legitimate deal breaker.
1:46:08 Interesting.
1:46:13 I remember being on a date right before COVID and politics came up and I was like, oh, I’m moderate.
1:46:17 And she instantly replied, oh, so you can’t make up your mind.
1:46:18 Oh, that’s interesting.
1:46:21 And I was like, whoa, that’s not what I said.
1:46:25 I was like, I’m just sort of like center, you know, I’m not extreme.
1:46:26 I’m not extreme left.
1:46:27 I’m not extreme right.
1:46:28 I’m policy based.
1:46:29 I’m not party based.
1:46:35 And it turned into this like really interesting discussion about politics.
1:46:38 But it was clear from her point of view that that was never going to work.
1:46:42 Did that change how you presented your political views on future dates?
1:46:48 Yeah, I was more hesitant to sort of bring them up because it could be such a contentious point.
1:46:53 But maybe you should bring them up earlier if you know it’s going to be a source of contention.
1:47:00 But I always think like, let’s avoid some of the more nasty stuff, at least in the first like few dates.
1:47:07 And then get into more understanding the person and how they approach life versus what do you think of abortion?
1:47:08 What do you think of politics?
1:47:10 What do you think of X, Y, Z?
1:47:13 Because then you’re just, you’re almost looking for an argument, right?
1:47:18 Yeah, you know, I think it depends on how important those things are to you.
1:47:25 So if somebody said, I’m Muslim, I really want to raise my kids to be Muslim, talking about that on a first date feels completely fair.
1:47:26 Totally.
1:47:31 So if you feel the same way about your political views, then I’m totally fine with somebody talking about that on a first date.
1:47:35 I don’t think it’s, let’s debate the role taxes play in America.
1:47:40 And it sounds like to you, having political views in common isn’t as important.
1:47:42 So I could see you talking about it later.
1:47:43 But it’s also shocking.
1:47:47 Like I had a Jewish woman once on a date ask me if I would convert.
1:47:48 And I’m like, it’s a first date.
1:47:50 Like, wow, I don’t know.
1:47:52 I’ve never thought about this, you know?
1:47:53 Yeah, but then when you-
1:47:54 But that’s important to you.
1:47:56 But then what did you think?
1:47:57 What did you say?
1:47:58 Exactly what I just said.
1:47:59 Like, I don’t know.
1:48:00 I’ve never thought about that.
1:48:04 I understand from you bringing it up so early that it’s like clearly important to you.
1:48:08 You know, that’s a really interesting one because I could see it going a few ways.
1:48:13 So I could see it being where the guy, not just you, but in general, is like, that’s way too forward.
1:48:14 That’s way too intense.
1:48:19 The truth is that if I was in love with somebody, I might consider it.
1:48:22 But being asked on the first date, it makes me so turned off that I’m not interested.
1:48:24 That is a much better response.
1:48:25 But I could see, no, no, no.
1:48:29 But I could see another argument in which the person says like, oh, you know what?
1:48:35 Actually, being Catholic is just such a big part of my family that like I just cannot ever see that.
1:48:38 And then the woman gets the information that she needs.
1:48:42 And so I think a lot of times it’s about how you bring things up.
1:48:46 You don’t want to paint somebody in a corner where they feel like there’s a wrong answer.
1:48:51 You want to sort of share and model and make them feel safe saying whatever’s true to them.
1:48:56 And so, for example, she could have said something like, you know, I’ve been dating for a while.
1:49:02 And the older I get, the more I realize my Jewish identity is really important to me.
1:49:05 And I grew up celebrating the holidays.
1:49:07 I really want to celebrate the holidays with my kids.
1:49:10 How important is your religion to you?
1:49:16 Then you get a chance to talk about your experience versus feeling like there’s a right answer.
1:49:18 Like what would you say to that question on a date?
1:49:24 I like your response, which is, you know, if I was in love with somebody, I don’t think it would really matter.
1:49:28 I haven’t thought about it at this point because I haven’t reached that point with somebody.
1:49:32 But it wouldn’t be a – I don’t think it would be a deal breaker for me.
1:49:32 But I don’t know.
1:49:34 Like I haven’t got to that point.
1:49:39 I think that’s a great answer because she can either say, eh, that’s wishy-washy.
1:49:40 I think that’s probably a no.
1:49:41 That’s not good enough.
1:49:42 Or, okay, he’s open to it.
1:49:46 Religion is not something where he has his own conflicting thing that he’s attached to.
1:49:53 And so in most of these situations, I feel like we think so much about like the strategy and the response and the right thing.
1:50:10 It’s like what if we just prioritize communication skills that allow people to ask questions that are true for them and listen to someone’s answer and have a conversation around it instead of like some AI resume reviewer that’s basically saying, well, they didn’t have the right keywords.
1:50:12 I’m not going to pass them on to the recruiter.
1:50:13 I like that approach.
1:50:20 Is it a red flag if a guy’s best friend is a girl or a girl’s best friend is a guy?
1:50:22 I don’t care about any of that stuff.
1:50:23 No, I knew you were going to say that.
1:50:24 But like statistically has that –
1:50:24 But like do you?
1:50:28 No, but I’m just wondering like what does the science say behind that?
1:50:30 I haven’t seen science behind that.
1:50:39 But just in my own relationship, I feel like a lot of my closest friends are men and the fact that, you know, just two days ago, I spent like a lot of the day with one of my close male friends.
1:50:43 And my husband was like, oh, I’m so glad that you’re getting to see David.
1:50:46 Like make sure you like ask him about this and that.
1:50:47 Like I want the update.
1:50:51 And it’s like it’s so attractive to me that he’s so confident.
1:50:53 But you hang out together, right?
1:50:54 Sometimes.
1:50:54 This is a person.
1:50:59 But like I have plenty of male friends that he’s not particularly close to.
1:51:06 And from the beginning, I think he’s just understood like Logan is a social creature with a lot of deep friendships.
1:51:18 And some of them are men and there’s this concept called other significant others, which is this idea that it came from research from Eli Finkel and Elaine Chung at Northwestern.
1:51:26 And you basically say to a couple, you know, who are the different people that you go to in your lives for different things, whether it’s like talking about TV shows, talking about baseball, career advice.
1:51:33 And couples that have longer lists of the individual people they go to tend to have these happier, more successful relationships.
1:51:40 Because instead of putting all the pressure on getting their needs met from one person, they actually have this network that they lean on.
1:51:49 And so my husband and I really invest in this idea of other significant others to the point where our WhatsApp channel with 30 of our friends is called OSOs.
1:51:52 And this is truly something that we in our community embody.
1:52:04 And so I think that when my husband knows I’m having brunch with Mike, he’s thinking, oh, Mike and Logan are just like these creative animals that literally have brunch with post-it notes and a notebook.
1:52:08 And like they’re just going to jam out in a way that Logan and I don’t.
1:52:11 And he feels like that makes Logan happy and makes our relationship stronger.
1:52:12 He doesn’t feel threatened.
1:52:14 And I think that that’s hard.
1:52:17 A lot of people do feel threatened or they do feel jealous.
1:52:25 But the more you can do in your own life to feel confident in yourself and your relationship, people just are drawn to that sort of confidence.
1:52:27 And it’s better for both partners.
1:52:31 Tell me more about this OSO WhatsApp group.
1:52:31 Yeah.
1:52:34 And like how it’s used and how it started.
1:52:36 I mentioned communal living.
1:52:41 So I have these friends named Kristen and Phil who are very visionary people.
1:52:47 And they are people that are truly living their values and thinking like many steps ahead of most people.
1:52:56 So in their 20s or maybe it was their early 30s when they were dating, they lived in this communal house that they ran in San Francisco where it was about like nine people in a house.
1:53:04 They would have dinner together and there was a lot of, you know, shared activities and close relationships.
1:53:06 And none of this is sexual.
1:53:09 This is not like – I don’t know if sometimes people’s heads jump to like orgies.
1:53:09 That’s really not the vibe.
1:53:11 My mind did not get that.
1:53:11 Okay, good.
1:53:19 The vibe is really like people who come home from work and like want to have an interesting dinner conversation with somebody else and like eat the like rice pilaf that they made.
1:53:25 So then they said, well, you know, we’re getting to be in our mid-30s and people are going to start having kids soon.
1:53:27 Well, this house is not going to work for kids.
1:53:34 So they bought a piece of property and they said, we’re going to turn this into the next phase where if people want to have kids, they can have kids.
1:53:37 And in the beginning, everyone is like this piece of land sucks.
1:53:39 This is like close to the highway and close to BART.
1:53:44 But like over the years, everyone flocked there including my husband and me.
1:53:50 So during the pandemic, when my husband was going through cancer treatment, that’s where we wanted to live.
1:53:56 We wanted to live with people, with a community of support, with these other significant others.
1:54:03 And so we really had just this group of people who were either old friends or new friends to rely on.
1:54:06 And this place now has five kids.
1:54:08 It’s soon going to have eight kids.
1:54:15 And people are just truly living in a pretty radical way, which is why do you have to have a concrete house with just you and your partner and your kid?
1:54:20 Why do all your resources have to go towards making one dinner and doing all the dishes?
1:54:23 What if you only had to cook every 14 days?
1:54:27 What if you could pull your resources and have a hot tub, a cold plunge, a sauna?
1:54:32 Like that stuff is doable when people live in this alternative environment.
1:54:36 It’s incredible because we tend to do that in Western world.
1:54:40 As we get older, once we retire, we go to a communal level.
1:54:40 Truly, yeah.
1:54:47 And, you know, there’s plenty of jokes there about like, you know, a millennial retirement community or I think someone’s called like a rave for introverts.
1:54:48 They have a lot of funny names for it.
1:54:54 But the point is that this is a group of people who have decided life is better when you’re living with your friends.
1:54:57 They’re not optimizing for the maximum square footage.
1:55:00 They’re not maximizing for the toniest neighborhood.
1:55:07 They’re really saying, I feel happy when I see a friend in the middle of the day without social coordination.
1:55:10 I feel happy when I have an interesting dinner conversation.
1:55:12 I love being able to host friends here.
1:55:21 And now having children there, people just feel like, oh, well, I never had to hire a babysitter because like I’ll watch this parent’s kid or they’ll watch my kids.
1:55:23 And like I no longer live there.
1:55:27 I live like in a house like 10-minute walk away.
1:55:32 But I truly feel like the people who are there are way less stressed than the average parent that I know.
1:55:35 I think that that’s true even if you’re not living in that community.
1:55:39 I mean, as a single parent, it takes a village to raise your children.
1:55:43 And having that help and social support network, easily accessible.
1:55:47 And I like how you mentioned uncoordinated kind of social events.
1:55:47 Totally.
1:55:51 I remember I used to live in the neighborhood of a lot of my close friends.
1:55:51 Yeah.
1:55:52 And then I moved.
1:55:52 Yeah.
1:55:58 And I missed those impromptu sort of wines or walk-bys or stuff.
1:55:59 Now it requires more coordination.
1:56:04 So there’s a lot of research that shows that people are happier if they live within a five-minute walk of their friends.
1:56:09 So Phil, one of the guys who started this community, he’s now built an entire company around this premise.
1:56:11 And the company is called Live Near Friends.
1:56:16 And it’s basically either how can you buy property with a friend or near a friend or even like rent something nearby.
1:56:28 It’s basically like instead of making your housing based on your commute or, you know, your favorite coffee shop, like why are we not centering our relationships?
1:56:28 Yeah.
1:56:29 I like that.
1:56:33 I think often it comes down to commute or cost, right?
1:56:44 We often trade off money to live farther away from the city, increasing our commute so that we can get a bigger house or I don’t know what the variables are because I don’t resonate with that.
1:56:46 So we’re in a relationship.
1:56:54 What are the questions that we should be asking ourselves as we decide whether we want to commit to this person for the rest of our lives?
1:56:56 Yeah, this is really hard.
1:57:02 I mean, the reason why I love that I have a background in behavioral science is that it’s really about,
1:57:05 the science of decision making.
1:57:08 And so much of a relationship is, am I ready to date?
1:57:09 Who should I date?
1:57:10 Should I keep dating this person?
1:57:11 Should we move in together?
1:57:12 Should we get married?
1:57:15 And so each of these is a pivotal point in your life.
1:57:19 And so the first thing I would say is just having a lot of honest conversations.
1:57:30 So before my husband and I got married, we did—there’s a great book called Eight Dates by the Gottmans, who are sort of the kings and queens of relationship science and really research-backed.
1:57:34 And in the book, there’s a series of dates that you should go on to get to know your partner.
1:57:36 And so there’s conversations about money.
1:57:38 There’s conversations around family.
1:57:41 There’s conversations about hopes and dreams in the future.
1:57:48 And I did all of the dates with my husband sort of as this, like, project where I was blogging about it.
1:57:59 But I’m really glad I had that container that forced me to do the dates because we got so much out of them that I think really did lead us to get engaged and kind of build a life together.
1:58:08 And so I think that the questions differ per person, but a lot of it is just sitting down and think about, like, what does our life look in the future—look like in the future?
1:58:10 Like, do you plan on working?
1:58:11 What are your values?
1:58:12 Do you want to have kids?
1:58:15 What are things from your childhood that you really want to repeat?
1:58:18 What are things about your childhood that you want to do the opposite of?
1:58:22 And I think sometimes when we’re so in love with someone, we just assume we’re on the same page.
1:58:32 And so just kind of echoing our earlier sentiment that I think it’s about having these intentional conversations to decide, is this somebody who I could really build a life with?
1:58:37 The other key thing is to understand that people often think, am I making the right choice?
1:58:42 There’s not really such thing as the right choice.
1:58:43 I don’t believe in soulmates.
1:58:51 It’s—I think that you could have many great relationships with many great people, and you get to decide, is this the person that I want to do it with?
1:58:56 And so, of course, you can think about the lives that you didn’t live and all the other stories that you could have written.
1:59:01 But instead, I think think about the fact that this is a story that I am excited to write.
1:59:04 Your husband sounds like an awesome man.
1:59:04 He’s great.
1:59:08 How do we end that relationship if we decide it’s not for us?
1:59:09 But we’ve been in the relationship.
1:59:15 So it’s not after a first date, but maybe we’ve been dating three months or six months, and we’ve reached one of these points.
1:59:16 We’ve had these conversations.
1:59:19 Now, how do we respectfully break up?
1:59:19 Okay.
1:59:22 We talked today about how painful rejection is.
1:59:32 And so I think the first guiding principle for breaking up with someone really should be empathy and just understanding and really imagining how painful it is to be broken up with in most situations.
1:59:35 And so a few things to keep in mind.
1:59:44 So one of them is there’s this rule kind of in corporate America that if you’re going to lay somebody off or give them a bad performance review, it shouldn’t be the first time that they’ve gotten that feedback.
1:59:51 So I think it’s much more fair to let somebody know throughout the relationship if something isn’t working.
2:00:03 I think it’s so painful for people when somebody breaks up with them and says, you know, you love going to restaurants and city culture, and I love camping and skiing, but since we’ve been dating, I haven’t gotten to do any of those things.
2:00:04 And then the person’s like, what?
2:00:06 You never brought that up once.
2:00:08 Like, of course we could have made time for that.
2:00:10 Why were you keeping that from me?
2:00:16 And so I think just understanding that as things are happening and coming up, share them with your partner so that you can tackle them together.
2:00:21 Maybe it comes to the same outcome of breaking up, but don’t kind of hide all of that.
2:00:23 Until the moment that you break up with them.
2:00:27 Another thing to keep in mind is I don’t think it’s the opportunity to give somebody feedback.
2:00:30 I think that can be very painful for somebody.
2:00:34 So sometimes in a breakup scenario, the person will be like, tell me what I did wrong.
2:00:35 Tell me when you fell out of love with me.
2:00:44 I don’t find that that’s helpful unless there’s something really specific like, I constantly felt like you were breaking plans with me or, you know, something that they can change.
2:00:45 You were unreliable.
2:00:46 You were unreliable.
2:00:49 But a lot of times it’s like you just weren’t a match.
2:00:54 And whatever you say to them is really going to stick in their mind and they’re going to go over it a million times.
2:00:56 So I just sort of find that that’s unhelpful.
2:00:58 There’s also this idea.
2:00:59 Do you know Hélène de Botton?
2:01:01 His work.
2:01:11 So he has this concept of like the nice breakup person where it’s like I’ll keep being in touch with you after the breakup because it makes me feel like I’m a nice person, which makes me feel better.
2:01:16 But it’s actually really about respecting your boundaries, which is like it’s probably better for you if we’re not as in touch.
2:01:26 And so really letting you define that or not trying to sort of assuage my own guilt by like being in touch with you all the time, which actually makes things harder for you.
2:01:37 So I have a conversation guide in my book for how to have a breakup conversation, which has a lot of things about like preparing for it in advance.
2:01:39 So when are you going to have this conversation?
2:01:43 You know, if somebody has a big presentation on Monday, like don’t do it Sunday night.
2:01:48 Is this person able to get in touch with some friends or family to support them afterwards?
2:02:00 So just really trying to soften the difficulty of the situation by setting them up to get support from other people, sharing with them kind of how you’re feeling but not giving feedback.
2:02:07 And then I think honestly not having sex with them and giving them space to honor the fact that this is challenging and they need to move on.
2:02:08 I like that.
2:02:10 I’d be remiss if I didn’t ask about dating profiles.
2:02:15 What are the tips that people, the most common things that people get wrong?
2:02:16 Yeah.
2:02:20 So I’ve done a ton of research on this and I can tell you some of the main tips.
2:02:25 So your dating app profile is sort of like your billboard.
2:02:32 And if you were buying a billboard, let’s say on the one-on-one in San Francisco, like you would, of course, think a lot about what you’re going to put on it.
2:02:35 And I think people should give the same amount of attention to their Hinge profile.
2:02:39 So, for example, you are telling a story about who you are.
2:02:47 So let’s say that you have a side of yourself that loves anime and there’s a side of yourself that’s passionate about baseball.
2:02:51 If all of your pictures are from Comic-Con, I’m not going to see that.
2:02:55 So really, I like to teach people this concept of your three big things.
2:02:58 What are three big things about yourself that you want to express in your profile?
2:03:03 And then make sure that through your prompts and through your photos, you’re getting those things across.
2:03:07 Another thing is having a mixture of humor and vulnerability.
2:03:11 You don’t want to be all jokes and you don’t want to be all super serious.
2:03:13 You want to show people different sides of yourself.
2:03:17 You also don’t want to fall into these dating app cliches.
2:03:22 So there’s this one on Hinge, like I’m overly competitive about everything.
2:03:24 And people have seen that all the time.
2:03:27 So like at best, they sort of just ignore it.
2:03:28 And at worst, they’re like, oh, cliche.
2:03:30 Like I’m not interested in that person.
2:03:39 There’s actually a new feature that just came out on Hinge called prompt feedback, which uses AI to kind of give you personalized private feedback on your prompt responses.
2:03:43 So like if you give a one word answer or it’s cliche, it’ll say like, dig a little bit deeper.
2:03:45 You know, what are you overly competitive about?
2:03:48 So hopefully that’s going to kind of raise all profiles.
2:03:55 Other do’s and don’ts, you know, don’t have one of those where’s Waldo photos where we can’t tell which one you are.
2:03:56 People don’t like that.
2:03:59 In general, selfies perform worse.
2:04:05 If you have sunglasses or filters or you’re wearing ski goggles, it’s really hard to tell what you look like.
2:04:08 So just like make it easy for the person to tell what you look like.
2:04:15 Have a photo of, you know, a clear headshot, photo of your full body, photo of you doing something that you love.
2:04:21 And then a photo with friends and family, but not so many that we can’t tell which one is you.
2:04:30 But in general, it’s really about using it as an opportunity to share who you are, what you’re looking for, and what kind of person you want to meet.
2:04:31 Should you smile?
2:04:32 Smile’s good.
2:04:34 Should you have a pet?
2:04:36 If you have a pet, sure.
2:04:38 But, you know, I think that when people…
2:04:41 You know what came to mind there is like Tim Ferriss did this thing.
2:04:47 I think I remember this correctly where he tested like 8,000 photos or something crazy.
2:04:51 And the one that was most successful was him like carrying a cat on the cover.
2:04:55 I have seen over the years different research about people with cats, people with dogs.
2:04:59 When I hear those things, I’m just like, do you have a fucking cat or dog?
2:05:02 Like if it’s really important to you, put it in there.
2:05:04 But like don’t dog bait somebody.
2:05:06 If you don’t…
2:05:06 I just made that up.
2:05:11 But it’s like if you have a friend with a cute dog, like putting the dog in your picture, it’s like that’s not representative.
2:05:15 It’s like show us authentically what spending time with you would be like.
2:05:22 So if you once went on a hike, but you actually spent every Saturday night playing board games, take a picture of board game night.
2:05:24 Don’t show that one hiking photo.
2:05:32 And so I think the dog or cat thing kind of fits into that overall advice of authentically show us who you are.
2:05:34 And if that involves your dog, great.
2:05:38 But if not, like don’t take 8,000 pictures, some of which have a stranger’s dog in them.
2:05:42 I always end on the same question, which is what is success for you?
2:05:48 Success for me is balance.
2:05:53 Feeling like I’m not forsaking my health for the sake of career.
2:05:57 Not feeling like I’m forsaking my husband for the sake of our daughter.
2:06:01 Not feeling like I’m forsaking my family for the sake of my friends.
2:06:07 And really just knowing my priorities and having that reflected in how I spend my time.
2:06:09 Thank you so much.
2:06:11 This was an awesome conversation.
2:06:11 Thanks for having me.
2:06:12 I really enjoyed it.
2:06:15 Thank you for listening and learning with me.
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