AI transcript
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0:00:07 You’ve heard the big hype around AI.
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0:00:27 All built into a single platform you can use right now.
0:00:29 That’s why the world works with ServiceNow.
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0:00:38 – I’m Anusa Ramonyan from Vox Media.
0:00:40 While I see them all around the city,
0:00:43 I’ve never ridden in an autonomous vehicle myself.
0:00:45 I do have some questions about the tech.
0:00:46 You may as well.
0:00:48 – Hello, from Waymo.
0:00:50 This experience may feel futuristic.
0:00:52 – This is so cool.
0:00:55 – Vox and Waymo teamed up for an in-depth study
0:00:57 about AV perception.
0:00:59 And what they found was that as people learned more
0:01:01 about Waymo, their interest in choosing one
0:01:04 over a human-driven vehicle almost doubled.
0:01:06 – Person approaching.
0:01:10 – Waymo can see 360 degrees and up to 300 meters away,
0:01:12 which helps it obey traffic laws
0:01:14 and get you where you’re going safely.
0:01:16 Swiss Re found that compared to human drivers,
0:01:20 Waymo reported 100% fewer injury claims
0:01:23 and 76% fewer property damage claims.
0:01:26 And speaking of safety, folks identifying as LGBTQIA
0:01:30 and non-binary showed the highest interest in AVs.
0:01:32 And women showed the greatest increase in interest
0:01:33 after learning more.
0:01:37 – Arriving shortly at your destination.
0:01:40 – So that actually felt totally normal.
0:01:42 AVs are here, and the more you know,
0:01:44 the more exciting this tech becomes.
0:01:46 You can learn more about Waymo,
0:01:48 the world’s most experienced driver,
0:01:50 by heading to Waymo.com.
0:01:53 – Episode 312, 312 is a year ago,
0:01:54 belonging to Chicago, Illinois.
0:01:57 In 1912, the Titanic hit an iceberg and sank.
0:02:01 And the Girl Scouts of the USA were founded.
0:02:03 Why do Girl Scout cookies taste so good?
0:02:05 Job labor.
0:02:09 Go, go, go!
0:02:12 (upbeat music)
0:02:19 – Welcome to the 312th episode of the Proxy Pot.
0:02:23 The dog is on vacation for the rest of August.
0:02:24 We’re gonna go to one of those dog farms
0:02:26 where I play with 30 other dogs,
0:02:27 roll around in deer urine.
0:02:30 You know, the usual, August, Augusto.
0:02:32 All month long on Thursdays,
0:02:34 you can expect conversations with blue flame thinkers,
0:02:37 innovators, professors, authors, and the like.
0:02:40 I didn’t write that, I would never say and the like.
0:02:42 Today, we’re sharing our interview with Nate Silver,
0:02:45 the founder of 538 and the New York Times bestselling author
0:02:47 of The Signal and the Noise.
0:02:50 He also writes the sub-stack, Silver Bulletin.
0:02:53 We discussed with Nate his latest book On the Edge,
0:02:55 The Art of Risking Everything.
0:02:56 I could write a book called On the Edge
0:03:00 about fucking depression, anxiety, and turning 50
0:03:02 and looking like you’re fucking 80 years old.
0:03:05 That’s what it would mean to be on the edge, Nate.
0:03:07 Anyway, we hear about the role of risk
0:03:10 in shaping modern life, his background in election forecasting,
0:03:14 and his thoughts on Kamala Harris’s VP pic.
0:03:17 Oh, that’s kinda, that’s what you call timely.
0:03:19 That’s why you come to the Prop G pod.
0:03:21 That’s why you come to the PGP, if you will.
0:03:24 We really enjoyed this conversation
0:03:26 and thank you, Will, as well.
0:03:30 Nate, where does this podcast find you?
0:03:31 – At home in New York, Manhattan.
0:03:33 – You live in the city, where do you live in the city?
0:03:35 – What would charityally be called Chelsea?
0:03:38 Kinda by Penn Station, Madison Square Garden, basically.
0:03:41 – So let’s talk about your new book On the Edge,
0:03:43 The Art of Risking Everything.
0:03:47 You investigate the river, the community of like-minded people
0:03:49 whose mastery of risk allows them to shape
0:03:52 and dominate so much of our modern world.
0:03:54 Can you explain what you mean by the river?
0:03:57 – So I have a very kind of geographic mind.
0:03:59 I like a good geographic memory
0:04:01 and I like looking at maps and things like that.
0:04:05 So I kinda wanted to create a metaphorical place
0:04:07 where a certain type of person lives.
0:04:09 And this type of person has two
0:04:10 basically defining characteristics.
0:04:12 One is that they’re super analytical.
0:04:16 They’re kind of in the moneyball, math nerd tradition
0:04:17 for the most part, so they’re playing poker
0:04:20 or founding companies or things like that.
0:04:25 The other is that they’re extremely insanely competitive,
0:04:28 which makes them really risk taking for the most part.
0:04:30 They wanna win, they wanna prove things to themselves
0:04:32 and other people.
0:04:34 They aren’t afraid to stand out.
0:04:37 They can be contrarian to the point of sometimes being
0:04:39 more than a bit annoying, I think.
0:04:42 But I kept finding the same personality type
0:04:43 in all the different fields that I cover.
0:04:46 I mean, I kind of started in the world of poker.
0:04:48 I actually have a background as a professional poker player.
0:04:51 But if you talk to people in Silicon Valley
0:04:56 or people trading crypto or people making sports bets
0:04:58 or even the effective altruists who we’ll talk to
0:05:01 a little bit later and the AI people,
0:05:04 they all have this kind of same competitive nerd
0:05:06 analytical personality in mind.
0:05:09 They speak the same language and it’s a small community.
0:05:14 The river is a community of mostly successful elites,
0:05:15 I guess you’d call them.
0:05:16 And you go to Silicon Valley,
0:05:18 it’s kind of a small world still.
0:05:21 It’s not sprawling through thousands of people.
0:05:24 The top VC firms might have a dozen partners or something,
0:05:25 but not hundreds.
0:05:29 And so there’s more community than I would have thought.
0:05:32 And you’ve seen that community have a rivalry more and more
0:05:34 with this other community that I call the village.
0:05:37 – And talk about the distinction between folks in the river
0:05:39 and folks in the village.
0:05:42 – Yeah, so the village is basically,
0:05:44 if you think of it as kind of New York, Boston, Washington,
0:05:45 maybe except for like Wall Street.
0:05:49 So it’s like government, media and academia.
0:05:52 So the kind of quintessential river village rather institutions
0:05:55 are like Harvard University and the New York times.
0:05:58 So it’s politically progressive for the most part.
0:06:02 As compared to the river, it’s much less analytical.
0:06:06 In fact, it’s very concerned about social status
0:06:07 and social appearances.
0:06:10 The ultimate punishment in the village
0:06:12 is to be ostracized or I suppose canceled.
0:06:15 That’s becoming a little bit outmoded.
0:06:17 And it’s risk averse.
0:06:18 It’s kind of neurotic.
0:06:20 It was much more cautious during COVID.
0:06:22 It’s afraid of offending people.
0:06:25 And there’s a rivalry between these two communities
0:06:27 increasingly when you see things like,
0:06:30 I guess it was last year, maybe in January,
0:06:32 when you see like hedge fund investors attacking
0:06:35 like university presidents who are speaking before Congress,
0:06:37 that’s an open conflict, I would say.
0:06:40 When you see people in Silicon Valley
0:06:41 kind of going more to war
0:06:44 with like the Democratic Party establishment,
0:06:46 we’re actually seeing this kind of play out more and more.
0:06:48 – I mean, I’m loosely the words that come into my mind
0:06:51 are kind of libertarian versus establishment.
0:06:52 Is that fair?
0:06:54 – I think the river would champion itself
0:06:57 as kind of lowercase L libertarian.
0:07:01 And would champion itself as being apolitical,
0:07:03 but of course it’s often hypocritical.
0:07:06 People go from being apolitical to being like Elon Musk,
0:07:10 or you’re very politically charged up on a lot of issues.
0:07:13 I mean, if you did a survey of the people I call riverians,
0:07:16 they’d probably be three to two Democratic
0:07:18 before Republicans still, or two to one maybe.
0:07:21 It’s, I mean, most communities of elites today
0:07:23 where you have high educational credentials
0:07:25 tend to be Democrats in the United States,
0:07:28 but it’s notably more varied than the village,
0:07:33 which is kind of uniformly 95% blue Democratic progressive.
0:07:36 – Talk about what you think are the key habits
0:07:38 of highly effective risk takers
0:07:39 that you talk about in your book.
0:07:41 – There’s a list of 13 of these in the book,
0:07:45 and they kind of fall somewhat into personality characteristics
0:07:48 and somewhat into psychological characteristics.
0:07:50 From a psychological standpoint,
0:07:53 some degree of detachment,
0:07:56 where you’re focused on process and not results.
0:07:59 If you play a poker hand, you can play the hand perfectly.
0:08:01 And if your opponent makes her flush draw,
0:08:04 you’re still gonna lose that hand a third of the time.
0:08:06 That process orientation, I think,
0:08:08 is counterintuitive for most people.
0:08:10 Personality wise, some of it does come down
0:08:14 to simply being willing to take risks and being courageous.
0:08:16 Maybe the single most important defining characteristic
0:08:20 is being cool under pressure in most walks of life.
0:08:23 Higher stakes moments vastly outweigh the day to day.
0:08:25 If you do make it deep in a poker tournament
0:08:27 playing for a million dollar first prize,
0:08:30 it’s more important by a factor of 1,000 X
0:08:33 than your Tuesday night beer league game, for example.
0:08:35 Learning how to handle pressure is important.
0:08:36 I mean, I did, like I said,
0:08:38 talk to mostly people who are doing
0:08:40 analytic math-oriented things.
0:08:44 But I also talked to an astronaut, an explorer,
0:08:46 a military commander, people like this.
0:08:49 And I heard some of those same things over and over.
0:08:51 One thing I heard a lot is don’t try to be a hero
0:08:52 when you’re under pressure,
0:08:54 when you’re like literally in outer space
0:08:57 and some red light is blinking.
0:09:01 Trusting the process, following protocol,
0:09:03 that kind of frees up bandwidth
0:09:05 for dealing with an emergency versus just like winging it.
0:09:08 So it’s a lot of preparation and experience
0:09:10 and coolness under fire.
0:09:12 – It’s interesting because, well,
0:09:15 the way I would try and translate that to entrepreneurship
0:09:19 is I don’t think I’d be nearly as good an entrepreneur now
0:09:20 as I was when I was a younger man.
0:09:22 Because when I was a younger man,
0:09:25 I had a bit of sociopathy in the sense that
0:09:27 it could be awful around me in my business
0:09:30 and we were running out of funding.
0:09:31 And I’d be stressed,
0:09:33 but I would still be able to sleep at night.
0:09:35 I just didn’t, I didn’t,
0:09:37 I was almost sort of sleepwalking through life and didn’t,
0:09:40 and now I’m too anxious.
0:09:42 I’m too kind of concerned about the downside.
0:09:45 Do you think there’s any truth in that?
0:09:46 – For sure.
0:09:49 I think it’s not a coincidence that more founders are younger,
0:09:50 although there’s probably some stereotyping
0:09:52 that takes place some of you sees.
0:09:54 Poker players are often younger too,
0:09:57 despite it being a game that it takes a lifetime to master.
0:10:00 That’s partly also a matter of physical fitness, I think.
0:10:03 But yeah, the ability to like shut out distractions
0:10:05 and be really focused is really hard
0:10:10 and maybe not entirely healthy sometimes either.
0:10:12 But yeah, as you gain more responsibilities, right?
0:10:15 So I played as I do most years,
0:10:17 I went to the World Series of Poker this year and played,
0:10:19 but it’s an election year.
0:10:20 I have this book coming out.
0:10:23 So there were like constant distractions
0:10:26 and it was in my best interest to manage those, right?
0:10:29 I can write newsletter posts and gain subscribers
0:10:32 or book interviews and publicity for the book.
0:10:34 But still, yeah, part of what comes with being an adult,
0:10:36 I think, is you have a little bit more to lose.
0:10:38 That can make you more risk-averse,
0:10:40 you have more responsibilities, and that can be okay.
0:10:43 But if you’re a VC trying to invest in a founder,
0:10:46 you want a founder who has kind of literally
0:10:50 insane single-minded focus, maybe for a period of 10 years,
0:10:52 whatever runway period that you have,
0:10:54 and that not be a younger person’s game.
0:10:58 – People thought people are risk takers and are successful,
0:11:00 are good at taking smart risks.
0:11:02 In other words, to a certain extent,
0:11:06 the risks they take, they do the analysis and go,
0:11:08 there’s a greater upside here that,
0:11:10 you know, a one in betting on a team
0:11:13 that has a 50 to one chance, you get 50 to one odd,
0:11:16 seems like crazy risk, but if you actually have done
0:11:18 the analysis and say the likelihood is more like 30 to one,
0:11:21 that’s a good risk, how would you coach young people
0:11:24 around how they approach risk?
0:11:26 – I think probably 90% of people,
0:11:28 of course, in your probability,
0:11:30 I think probably 90% of people could stand
0:11:34 to be more risk-taking, at least in terms of like
0:11:36 their career lives.
0:11:38 I’m not saying, oh, go do drugs or something like that,
0:11:39 that’s a personal choice.
0:11:41 You know, look, we have a lot of evolutionary training
0:11:44 where we don’t live in this kind of world of abundance
0:11:48 that we do now, where we don’t have as much of a safety net
0:11:50 if you fail, and where there was less of a war
0:11:52 for taking risks, you go out and get some infection
0:11:54 or something, and there’s no cure for it,
0:11:56 then you die, and now we’re in a world of abundance
0:12:00 and we can afford to think more in terms of expected value,
0:12:04 which means kind of, what is the outcome you get on average
0:12:05 when trying this thing?
0:12:07 ‘Cause there’s uncertainties in the world.
0:12:09 If you play poker, then some percentage of time
0:12:10 you’re gonna win the tournament,
0:12:12 more often than not, you bust out,
0:12:14 but are you making, or is it a plus EV,
0:12:16 positive expected value gamble on average?
0:12:19 Now, if you’re a founder and you’re making these
0:12:21 long, prolonged, 10-year bets,
0:12:22 then maybe it’s a little bit different, right?
0:12:24 I mean, the kind of brilliant thing
0:12:26 that venture capitalists do is they gather together
0:12:29 all these founders who are making long shot bets
0:12:30 with probably positive expected value,
0:12:33 but many of them will fail.
0:12:34 If you make enough of those bets,
0:12:36 then you’re kind of guaranteed
0:12:38 to do very well for yourself, right?
0:12:40 Enough of them will pay off in a,
0:12:43 you have a fund of 15 or 20 or 25 companies every year,
0:12:45 then sooner, and you have your pick of the litter,
0:12:47 you’re picking the best founders,
0:12:49 then that’s a very good business.
0:12:50 For a founder, it requires, I mean,
0:12:53 I think it literally does require more risk.
0:12:55 I mean, if you are any one founder,
0:12:57 your company may fail,
0:12:59 which is partly why, you know,
0:13:01 you get people like Elon Musk,
0:13:03 who like literally, if you read the,
0:13:07 the Isaacson book on him about Elon playing poker,
0:13:09 he would like literally just kind of go in,
0:13:12 go all in every hand until he’d lose
0:13:14 and he’d walk away from the table and do something else.
0:13:16 He’s not 10% group where he’s probably taking
0:13:19 on too much risk, I would think,
0:13:21 but these are often people that have chips on their shoulder
0:13:23 that almost have like an evolutionary
0:13:27 or genetic kind of propensity to take risk.
0:13:29 – Yeah, I wonder if they’re to a certain extent,
0:13:29 I’m not talking about Elon Musk,
0:13:33 but they have their addicts in the sense that
0:13:36 they take risk and the new kind of the new dopamine balance
0:13:41 after taking some risk is to have that rush
0:13:42 you have to take more risk.
0:13:45 I used to, I worked for a hedge fund manager
0:13:48 who at one point was the, I think the 50th
0:13:51 or the 70th wealthiest person
0:13:55 and he kept taking these just outsize crazy risks
0:13:57 until he ended up broke.
0:14:01 And he just has like almost a psychotic approach
0:14:05 or aggressive approach to risk.
0:14:07 I want to bring it down to entrepreneurship
0:14:10 because I’ve been an entrepreneur for most of my life
0:14:12 and it raised a lot of money from VCs.
0:14:14 And where I thought there was a bit of a disconnect
0:14:17 or dislocation between their interests and my interest
0:14:21 is that they would always encourage me as the CEO
0:14:23 or the founder of a company when I was going well
0:14:25 to go bigger, harder, bolder
0:14:29 because they’re looking for billion dollar exits
0:14:33 to pay for the 70 or 80% of their portfolio
0:14:35 that doesn’t even get its money back
0:14:38 and half of them that go to zero.
0:14:39 And they need those big pops.
0:14:43 And I was thought, okay, I don’t need to be a billionaire.
0:14:45 I need to have economic security
0:14:46 and this is where our interests diverge
0:14:48 because I used to advocate for
0:14:51 and usually would ultimately would win
0:14:53 for selling the company.
0:14:55 I sold my first company for 33 million.
0:14:56 Our investors were disappointed.
0:14:59 I sold my last company for 160 million
0:15:02 despite my investors tripling their money in 27 months.
0:15:04 They were disappointed
0:15:06 because I didn’t have a bunch of chips on the table.
0:15:09 I had one big chip on one number.
0:15:12 And so it creates a divergence of risk.
0:15:15 Can you talk a little bit about where, you know
0:15:17 are there other divergences, whether it’s an employee
0:15:19 and you’re, you know
0:15:22 of a company or an entrepreneur or founder and VCs
0:15:26 how do you want to be thinking about an approach to risk
0:15:28 based on where you are in an organization?
0:15:30 – No, Scott, I think that’s right.
0:15:33 And I think kind of VCs get the better side
0:15:37 of that VC founder interaction most of the time.
0:15:39 And it’s probably why they’re picking people
0:15:43 who have huge variants in their outcomes, right?
0:15:44 You’re not going to pick somebody
0:15:48 to run like a chain of three ice cream stores
0:15:49 in Boise, Idaho or something, right?
0:15:50 Where the upside is capped.
0:15:53 You want people that wind up on the extreme tails
0:15:54 because the thing you hear over and over and over again
0:15:56 from everyone in Silicon Valley is like
0:16:00 you can’t miss out on the 1000X X and your money opportunity.
0:16:03 You cannot let Mark Zuckerberg walk through the door.
0:16:05 So the downside of that is you sometimes get a Mark Zuckerberg
0:16:07 and sometimes you get a Sam Bakeman Fried
0:16:09 or Elizabeth Holmes or whatever else.
0:16:12 I mean, even in my own world, you know
0:16:15 I kind of run I guess my own content business
0:16:17 and realizing that it’s actually a much better business
0:16:19 where it’s smaller scale, right?
0:16:21 I keep more of the profit myself.
0:16:22 I don’t have a bunch of employees
0:16:26 whose marginal contribution can be debated, I suppose.
0:16:28 And so yeah, I found that when I’m smaller
0:16:31 I actually am happier and more successful financially
0:16:32 but the obsession with scale
0:16:34 especially in the media business
0:16:36 which is maybe its own special beast
0:16:38 but the obsession with scale makes sense
0:16:40 in most contexts from a VC standpoint
0:16:43 but may not be in the interest of the founder.
0:16:46 – In terms of your own personal life and risk taking
0:16:50 I’ve always bifurcated it and it may be incorrect
0:16:51 but again, just trying to reverse engineer this
0:16:54 into actionable advice for young people.
0:16:58 There was my risk profile before kids and then after kids
0:16:59 and I left investment banking
0:17:02 which on a risk adjusted basis was what I should have stuck
0:17:05 with but I wasn’t enjoying it and I wasn’t very good at it.
0:17:08 And then I moved home with my mom because I’m like
0:17:10 oh, I don’t know what I’m gonna do
0:17:12 and not knowing what you wanna do and quitting
0:17:15 doesn’t pay well so I moved back in with my mom
0:17:17 and I took risks and I applied to graduate school
0:17:20 started businesses, my first business
0:17:23 I didn’t have any money but my girlfriend was making money
0:17:26 so I could take that risk.
0:17:30 Once I had kids and I think this is the correct instinct
0:17:32 I’m like okay, shit just got real.
0:17:36 My, you know, me and my two sons can’t move back in
0:17:39 but my mom or it’s gonna be very uncomfortable
0:17:42 and it absolutely changed my risk profile.
0:17:44 A lot more anxiety, a lot more concern around risk
0:17:46 but I think that was the correct emotion.
0:17:50 Would you describe other seminal moments in your life
0:17:52 that you wanna think about risk before and after
0:17:54 and doesn’t this all add up to when you’re young
0:17:56 is the time to take risks?
0:17:59 – I think so, I mean, I don’t have kids
0:18:01 and so that’s like one more reason to kind of gamble
0:18:04 on your upside and not necessarily worry
0:18:06 about a secure paycheck, I don’t think.
0:18:08 Yeah, I think that heuristic is basically right
0:18:10 that when you’re younger you have more opportunity.
0:18:14 I mean, look, I think people sometimes set the bar too low
0:18:17 as far as life outcomes that they’re satisfied with
0:18:19 because my first job out of college
0:18:21 I had a consulting job, I was something called
0:18:23 a transfer pricing consultant
0:18:25 which is about as boring as it sounds like
0:18:28 and quit that to play online poker basically
0:18:29 where I was making more money
0:18:31 and to work for a internet startup
0:18:33 that wrote about baseball statistics.
0:18:38 So quitting a safe consulting job is a somewhat risky endeavor
0:18:39 but it proved to be a better decision
0:18:43 and I think people need to have a higher reserve price
0:18:44 to use a slightly technical term
0:18:47 for how they’re spending their time.
0:18:49 There’s also studies, I mean, Stephen Leavitt
0:18:51 of Freakonomics did a famous paper
0:18:55 where he would actually have people literally flip coins
0:18:56 to make major life decisions.
0:18:59 So should I move across the country or quit my job
0:19:01 or get divorced or get married
0:19:03 and found that when people flipped a coin
0:19:05 they told them to make a change
0:19:07 they wound up being happier on average.
0:19:09 The importance of quitting.
0:19:10 I don’t know if you had Annie Duke on the show
0:19:13 former poker player who now writes business books
0:19:15 wrote a book called quit.
0:19:18 Getting out of a bad situation while you can
0:19:23 or maybe half a move ahead is an underrated skill I think.
0:19:25 I think people are too willing to muddle through
0:19:27 not have a long enough time horizon
0:19:30 and wind up being mired in an unhappy place.
0:19:32 – I think that’s a great insight
0:19:33 and I just wanted to stop on that.
0:19:36 There’s this mythology from Donald Trump down
0:19:37 and like never give up.
0:19:39 Oh, there’s a time to give up.
0:19:41 I mean, absolutely.
0:19:42 There’s a time to leave.
0:19:44 And I would say that’s where a kitchen cabinet comes in
0:19:46 to advise you that, okay, you’re banging your head
0:19:47 against a wall.
0:19:49 You need to move on to different opportunities.
0:19:51 Several chapters of your book focus
0:19:54 on Sam Bankman Freed and the crypto world.
0:19:56 What do you think people miss about FTX
0:19:59 and Sam Bankman Freed and how it relates to risk?
0:20:03 – So he is certainly on the extreme right tail
0:20:05 of risk-taking where he literally said
0:20:08 in repeated interviews that if he could push a button
0:20:10 and gamble for the future of the universe
0:20:12 and either the universe is destroyed
0:20:15 or 51% of the time it winds up being twice as good
0:20:17 then it’s a positive expected value bet.
0:20:18 So he’d make it.
0:20:21 That’s a pretty insane way to look at life.
0:20:25 And I think people were too unwilling.
0:20:28 I think there was a little bit of a kind of boy genius myth
0:20:30 around Sam.
0:20:31 And there was a little bit of a bystander problem
0:20:34 where it seemed like all these people are vouching for him.
0:20:35 Therefore he must be smart
0:20:39 and therefore people weren’t willing to point out
0:20:41 sometimes crazy and kooky things that he was willing to say.
0:20:44 And it’s a little bit of a cult of personality,
0:20:46 the cult that the village or the river would think it avoids
0:20:48 that actually winds up having with founders
0:20:50 like SPF sometimes.
0:20:53 I think he was also not a very good risk assessor
0:20:55 despite thinking of himself as one.
0:20:59 I talked to a lawyer right as his criminal trial
0:21:01 and Manhattan was taking place.
0:21:04 And the lawyer said he should not take the stand.
0:21:08 He should cut his losses and try to minimize his sentence
0:21:10 at five to 10 years.
0:21:13 If he takes a stand, he’s for sure gonna hurt yourself,
0:21:17 which he did and he wound up getting like 20 years instead.
0:21:20 When I talked to Sam and Palo Alto six months before the trial,
0:21:24 I said, what if you were offered a two year plea deal,
0:21:27 two years and then some restrictions
0:21:28 on what you can do afterwards.
0:21:30 So kind of more than a slap on the wrist,
0:21:31 but not that much more.
0:21:33 And he said, I’d have to think about it, right?
0:21:35 So I mean, he was 10 X off
0:21:36 of what the realistic outcome was gonna be.
0:21:38 He got 20 years of course.
0:21:41 And I think, I think, look, as a poker player,
0:21:44 I’ve seen lots of people in the SPF typology.
0:21:49 So kind of smart, nerdy, maybe a little bit on the spectrum,
0:21:53 you know, neurotic, Adderall, whatever quick on his feet.
0:21:58 And not all of them are as smart as they’re cracked up to be.
0:22:01 So I think people needed to have more skepticism of him
0:22:04 both kind of before, during and after the bankruptcy.
0:22:06 – I would argue that’s a perfect example
0:22:10 of just ridiculously stupid risk-taking.
0:22:13 I can’t imagine how frustrated his lawyers must have been.
0:22:16 Like, okay, you are doing everything wrong here.
0:22:19 I’m curious, have you tried to relate some of your thoughts
0:22:21 and analysis around risk-taking
0:22:24 to people’s relationships or personal life?
0:22:25 You said you don’t have kids.
0:22:26 I don’t know if you’re in a partnership,
0:22:29 but have you thought about approach to risk
0:22:33 as it relates to relationships and outcomes?
0:22:36 – Yeah, I’ve been a long-term relationship, no kids.
0:22:37 I guess I’d say, frankly, not as much.
0:22:40 I mean, I’m trying to keep, it’s already a long book.
0:22:41 It’s like 500 pages.
0:22:43 So I’m trying to keep the scope of it somewhat narrow.
0:22:48 I think some of it does apply that people, you know,
0:22:52 probably are settle a little bit too easily sometimes.
0:22:55 I think the importance of what I call,
0:22:57 or not what I call the importance of optionality,
0:22:59 I think is really important in both business
0:23:01 and interpersonal affairs,
0:23:03 where are you walking down a hallway
0:23:06 where there are a lot of doors open, right?
0:23:08 It’s kind of a stupid analogy,
0:23:11 but, you know, I’ve lived in New York for 15 years now,
0:23:13 so my partner and I, we have a, you know,
0:23:14 pretty good group of friends.
0:23:16 And so let’s say you don’t have plans
0:23:19 on a Thursday night, well, there’s a whatever,
0:23:22 one in three chance that someone will text you and say,
0:23:24 “Hey, I just have made a reservation
0:23:25 “on this new dinner place,
0:23:28 “or you want to go to the Yankees game.”
0:23:30 Just these kind of cool opportunistic things.
0:23:32 Let’s go to an art gallery that you don’t have
0:23:35 if you haven’t facilitated different options in your life.
0:23:38 – We’ll use the word optionality.
0:23:40 You’re an analytics guy.
0:23:42 Do you think it makes sense to get married?
0:23:44 We’ll be right back.
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0:25:38 – I’m Anusa Brahmanyan from Vox Media.
0:25:39 While I see them all around the city,
0:25:42 I’ve never ridden in an autonomous vehicle myself.
0:25:44 I do have some questions about the tech.
0:25:45 You may as well.
0:25:48 – Hello, from Waymo.
0:25:50 This experience may feel futuristic.
0:25:51 – This is so cool.
0:25:54 – Vox and Waymo teamed up
0:25:56 for an in-depth study about AV perception.
0:25:57 And what they found was that,
0:25:59 as people learned more about Waymo,
0:26:01 their interest in choosing one
0:26:04 over a human-driven vehicle almost doubled.
0:26:05 – Person approaching.
0:26:09 – Waymo can see 360 degrees and up to 300 meters away,
0:26:11 which helps it obey traffic laws
0:26:13 and get you where you’re going safely.
0:26:16 Swiss Re found that, compared to human drivers,
0:26:19 Waymo reported 100% fewer injury claims
0:26:22 and 76% fewer property damage claims.
0:26:23 And speaking of safety,
0:26:27 folks identifying as LGBTQIA and non-binary
0:26:29 showed the highest interest in AVs
0:26:31 and women showed the greatest increase in interest
0:26:32 after learning more.
0:26:36 – Arriving shortly at your destination.
0:26:40 – So that actually felt totally normal.
0:26:41 AVs are here and the more you know,
0:26:44 the more exciting this tech becomes.
0:26:46 You can learn more about Waymo,
0:26:48 the world’s most experienced driver
0:26:49 by heading to Waymo.com.
0:26:54 – We’ll use the word optionality.
0:26:55 You’re an analytics guy.
0:26:58 Do you think it makes sense to get married?
0:27:01 – Probably for tax purposes and stuff like that.
0:27:02 I mean, there’s still,
0:27:04 probably my partner and I should think about it
0:27:05 at some point.
0:27:09 Yeah, I think there are still benefits
0:27:12 from being married in terms of just the way
0:27:13 the tax code tweets it and things like that,
0:27:16 which, you know, was like a very, very clinical answer.
0:27:19 You know, I do think sometimes commitment is also,
0:27:20 can also be a good thing.
0:27:23 I mean, I think there can be paradoxes of choice
0:27:25 where you have too many options.
0:27:28 That’s actually kind of one thing I worry about out there
0:27:29 in the world a little bit is that like,
0:27:30 if you’re somebody who’s really good
0:27:32 at taking advantage of optionality,
0:27:35 then the world’s kind of your oyster now, right?
0:27:38 Now you can work from home and have five different jobs,
0:27:39 which I kind of do now.
0:27:41 And it’s like, but it’s a lot to balance.
0:27:43 And if you’re under duress, right?
0:27:46 If you do have kids or an older relative
0:27:48 that you’re taking care of,
0:27:52 if you’re injured somehow or incapacitated somehow,
0:27:54 then it becomes a lot harder potentially.
0:27:57 So I wonder if it leads to like a little bit more of a,
0:27:59 even though like Scott, you might take advantage of it
0:28:01 or I might, I wonder if it leads to a little bit more
0:28:04 of like kind of a winner take all world.
0:28:06 – I think you see that on online dating.
0:28:09 It’s great to be, I mean,
0:28:11 there’s income inequality and I’m crazy in online dating.
0:28:15 My understanding is the top 10% of most attractive males,
0:28:18 if you will, to get 80% of the opportunities.
0:28:20 – Oh yeah, that wouldn’t surprise me one bit.
0:28:22 And then in some sense, I mean, look,
0:28:26 the capitalist internet driven economy
0:28:28 is extremely effective at delivering
0:28:30 whatever the efficient outcome is.
0:28:33 And mostly speaking, I am pro market,
0:28:34 but like we should think about situations
0:28:36 where the efficient outcome,
0:28:39 the market efficient outcome is like not serving
0:28:40 the greater good necessarily.
0:28:42 And that might eventually kind
0:28:45 of market correct itself somehow.
0:28:47 I’m not quite sure how I’ve been in the same relationship
0:28:49 for a long time now.
0:28:52 But yeah, that’s a great microcosm of it, I agree.
0:28:55 – So let’s shift to politics.
0:28:57 So Nate, who’s gonna win the election?
0:28:59 How’s that?
0:29:00 Let’s kick off there.
0:29:01 Who do you think’s gonna win?
0:29:04 – I can give you the honest dodge,
0:29:06 which is our model as of this morning we’re taping this.
0:29:08 It’s about literally about 50/50.
0:29:12 Joe Biden had been a pretty heavy underdog to Trump
0:29:14 and his position, in fact, was worsening in our model.
0:29:16 He was at about 25%.
0:29:17 I think it might have actually been high.
0:29:19 Given that he, his fundraising had dried up,
0:29:21 that he wasn’t really capable
0:29:22 of running a full-fledged campaign.
0:29:25 With Trump Harris, it’s a lot more even.
0:29:26 It’s important for Democrats to remember
0:29:30 that Democrats have a disadvantage in the electoral college.
0:29:32 So she is a favorite to win the popular vote.
0:29:34 She is ahead for right now
0:29:36 in most polls of the popular vote.
0:29:37 But the electoral college, Pennsylvania,
0:29:40 Wisconsin, Michigan, Georgia, et cetera,
0:29:42 is liable to be very close.
0:29:45 So yeah, I wouldn’t wanna wage her a lot of money
0:29:48 on this currently, but she has had momentum.
0:29:51 I mean, it’s been a pretty good rollout to her campaign.
0:29:55 And by the way, I mean, this was an example
0:29:58 of smart risk-taking from Democrats, right?
0:30:01 Is pushing Biden aside?
0:30:02 And they did push him aside.
0:30:04 I don’t buy this rhetoric at like Biden,
0:30:06 but evidently decided to resign.
0:30:09 I mean, Nancy Pelosi and Chuck Schumer were,
0:30:09 yeah, it was kicked out.
0:30:11 They were pulling every lever they could.
0:30:14 And that’s bold from a party
0:30:17 that’s often kind of triangulating and risk averse.
0:30:21 And so credit to them for giving themselves a 50/50 coin flip
0:30:24 instead of personally, I think, very likely lost with Biden.
0:30:26 Now they have a real chance.
0:30:28 – Speaking of sort of triangulating
0:30:30 and taking the less risky choice,
0:30:32 I was really hoping and thought it would have been
0:30:35 a great move to choose Governor Shapiro as the VP.
0:30:37 And they’ve picked Governor Tim Waltz.
0:30:40 So by the way, I think Briggs Greg sort of like dad energy.
0:30:41 And my guess is they’re banking
0:30:45 that he has regional appeal across the border states.
0:30:47 What are your thoughts on the VP pick?
0:30:49 And do you think it, I mean, at the end of the day,
0:30:54 my guess is that we always tend to overestimate
0:30:55 the impact it’s gonna have.
0:30:57 But what do you think of the Waltz pick relative
0:31:01 to kind of risk-taking and moving her chances up or down?
0:31:05 – No, I’m 100% aligned with that take of your Scott.
0:31:06 I think Josh Shapiro is a star talent
0:31:10 and he’s demonstrated empirically his popularity
0:31:12 in the most important swing state, Pennsylvania.
0:31:13 And Pennsylvania, by the way,
0:31:15 it’s a swing state for a reason, which it has,
0:31:18 it has urban areas, it has some diversity,
0:31:21 it has rural areas, it has suburbs around Philly
0:31:23 and Pittsburgh, obviously.
0:31:25 So he has like an actual demonstrated
0:31:27 empirical track record.
0:31:28 And you know, look, I think Tim Waltz
0:31:31 is a pretty good pick in a vacuum.
0:31:33 But I did think it was a little bit risk averse.
0:31:37 If she was a 70/30 favorite or an 80/20 favorite,
0:31:39 that’s what I thought it might have been right choice.
0:31:41 That’s when it’s like a do no harm choice.
0:31:43 I do think because she’s been moving up,
0:31:47 I mean, I think she maybe overrates the importance
0:31:50 of short-term momentum as opposed to in the long term,
0:31:52 it’s really gonna be nice to have someone
0:31:57 who can lock up Pennsylvania and its 19 electoral votes.
0:32:00 And someone who kind of really gets moderate,
0:32:02 it’s excited because actually the Democratic base
0:32:04 isn’t as large as it once was.
0:32:05 And if you look at the voter registration numbers,
0:32:08 and it’s more even now than it used to be.
0:32:11 And a tie goes to Republicans in Electoral College.
0:32:14 So I don’t think it’s a terrible choice.
0:32:16 I think I give like a B minus C plus.
0:32:18 But I think there was like a slightly riskier
0:32:21 but higher expected value option in Shapiro
0:32:23 that she declined.
0:32:26 – So the Trump campaign calls you,
0:32:27 and then the Harris campaign calls you
0:32:29 and asks for your advice on the two or three things
0:32:32 that you would do in terms of messaging or tactics
0:32:35 to improve their likelihood of a good outcomes.
0:32:37 First do Trump, they call you Nate,
0:32:39 what are your thoughts on what we should be doing
0:32:41 more or less of?
0:32:46 – I’d say lay off the anything involving
0:32:48 race, gender, sexuality.
0:32:51 I think that’s the Trump campaign at its worst
0:32:53 and the temptation to do that with, you know,
0:32:56 black Indian American women as the other nominee,
0:32:57 it must be tempting, you know,
0:32:59 I think Trump has continued to pivot to the center
0:33:03 on abortion to some degree, of course, you know,
0:33:05 his party was happy about Roe v. Wade being overturned,
0:33:07 but he’s tried to downplay that.
0:33:09 And I think in general, moderation is smart.
0:33:12 And I think kind of, you know, focusing,
0:33:14 I think the two big liabilities for Democrats,
0:33:17 maybe three actually, immigration is one.
0:33:18 I still think the economy is potentially
0:33:23 a big liability for Harris and Democrats.
0:33:26 It’s good by some measures, not as good by other measures.
0:33:29 We are, of course, are facing a lot of volatility recently
0:33:31 in the stock market who knows will be up and down
0:33:34 on the day that people are listening to this
0:33:38 and focusing a little bit too on tying Harris to Biden
0:33:40 because Trump was beating Biden by four points
0:33:41 or something like that in national polls
0:33:44 by the time that Biden quit the race,
0:33:46 that she’s been the vice president,
0:33:49 that you don’t get like a race board
0:33:51 once you’ve been the vice president for four years
0:33:53 that you kind of own that track record,
0:33:56 maybe even owns the fact that like Biden’s health
0:33:58 and fitness are things that the White House
0:34:00 has not been entirely straightforward about.
0:34:02 So those seem like it’s pretty basic stuff,
0:34:05 but you know, tax the center, avoid creepy race stuff
0:34:09 and focus on the problem she inherits from Joe Biden.
0:34:10 – Now do Harris.
0:34:12 – Go back in time and pick Shapiro,
0:34:14 but I guess it’s too late for that now.
0:34:17 Like I think they have otherwise run a pretty good campaign.
0:34:21 They have kind of unapologetically triangulated
0:34:23 to the center a little bit more.
0:34:26 They have tried out some new arguments,
0:34:29 this argument about calling Republicans weird, for example.
0:34:32 I’m not sure it’s fantastic and objectively speaking,
0:34:34 kind of most people who are into politics
0:34:36 are pretty weird by the Democrat or Republican,
0:34:39 but it’s a new look and I think she appreciates
0:34:41 or her campaign team appreciates
0:34:44 how much young voters in particular
0:34:45 were tired of the same playbook
0:34:47 for three elections in a row, right?
0:34:50 In 2016, younger voters wanted Bernie,
0:34:51 but it was, oh, you have to hold your nose
0:34:52 and vote for Hillary.
0:34:54 In 2020, they want to Bernie again.
0:34:55 Oh, it’s a pandemic.
0:34:57 You have to hold your nose and vote for Donald Trump, right?
0:35:00 In 2024, no primary process at all.
0:35:04 And, you know, and Democrats were asking way too much
0:35:06 of voters, I think to like, to ignore the fact
0:35:10 that Biden had clearly lost a step or two or three or four,
0:35:12 and it just wasn’t working at all.
0:35:15 And he was losing support among core demographic groups,
0:35:17 like young voters, especially, you know,
0:35:19 younger voters, black voters, Hispanic voters,
0:35:21 Asian-American voters of color.
0:35:24 So I think she’s been pretty smart so far.
0:35:27 Apart from the VP pick, I give her, you know,
0:35:30 a good grade for the first two or three weeks of the campaign.
0:35:31 – So I agree.
0:35:33 I thought Shapiro was a shillin’.
0:35:36 I just looked at all of these boxes he checked,
0:35:39 including, you know, being this incredibly popular governor
0:35:41 that would have delivered whatever it is,
0:35:44 the 19 delegates in a swing state.
0:35:46 Have you done any, my guess is they looked,
0:35:50 they’re hoping that Waltz has that type of appeal
0:35:52 across the region that he helps,
0:35:56 he helps their case in, in Wisconsin and Michigan.
0:35:58 Have you seen any analysis around
0:36:00 whether his popularity in Minnesota,
0:36:02 his cross-border and his regional?
0:36:03 – I tend to doubt it.
0:36:06 I mean, remember, like Wisconsin and Minnesota
0:36:09 are big rivals in football and hockey and things like that.
0:36:14 And even the home state VP effects are fairly small.
0:36:17 I mean, look, I want to read more reporting
0:36:19 on why Shapiro wasn’t chosen.
0:36:22 If they did a bad job of managing the internal process,
0:36:25 then it is like, I think a little bit more worrisome
0:36:26 for Harris, ’cause it certainly seemed
0:36:28 like that was the direction she was leaning.
0:36:31 She scheduled a rally in Pennsylvania
0:36:32 at one point on betting markets.
0:36:35 Shapiro was up to like an 80 or 90% favorite.
0:36:37 So, you know, if they got cold feet,
0:36:40 then I want to, I want to learn more about that.
0:36:41 ‘Cause if you do get cold feet,
0:36:44 I mean, there might have been like better ways
0:36:45 of framing that decision.
0:36:48 I mean, maybe say that Shapiro has some ailing family member
0:36:51 he has to attend to or wants to focus on 2028
0:36:52 or something like that.
0:36:55 But it was pretty strange to like tease
0:36:58 at this kind of obvious-seeming bolder choice
0:37:01 and then kind of losing at the altar.
0:37:03 I think maybe that is a little bit worrisome
0:37:05 for how they managed that, but we don’t know.
0:37:08 I mean, there could have been like a vetting issue.
0:37:11 They also moved up in the polls
0:37:12 with the course of making the pick.
0:37:14 So, they’re a little bit ahead of Trump,
0:37:15 so a little bit behind that might’ve made them
0:37:17 more risk-avers and that’s a bit more rational.
0:37:20 But yeah, it was, you know,
0:37:23 it’s somewhere between it’s fine
0:37:24 and maybe a more major mistake
0:37:25 depending on the reasons behind it.
0:37:27 And, you know, given the timing of the show,
0:37:30 I haven’t had reasons to read much reporting yet
0:37:32 about exactly why she made this move.
0:37:35 We’ll be right back.
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0:40:02 for a small shipping company.
0:40:06 The recruiter said all I needed to do was send $500
0:40:10 to cover mandatory software training and job was mine.
0:40:13 – Scams are happening like this more and more
0:40:16 because of the change in technology.
0:40:18 The sky’s the limit on scams.
0:40:20 – So says Deborah Baxley,
0:40:24 a mobile payments and FinTech consultant of over 20 years.
0:40:27 – Never be pushed into a sense of urgency.
0:40:30 Always sit back, think twice.
0:40:32 If something seems too good to be true
0:40:35 or a little bit weird, think about it.
0:40:37 – But there are steps you could take
0:40:38 to help protect yourself.
0:40:41 – You should never give out any, what we call PII
0:40:44 in the industry, personal identifying information,
0:40:46 which includes everything from your mailing address,
0:40:48 your social security number,
0:40:50 any kind of banking information.
0:40:51 – Encountering a crime like this
0:40:56 can be a little disorienting, stranger than fiction even,
0:41:00 almost like you’re in a TV show.
0:41:04 – Come in Safe Squad, we got a 10-3.
0:41:06 – That’s why Safe Squad was made,
0:41:08 the hottest new fictional crime drama
0:41:11 all about how to protect yourself from financial crimes.
0:41:13 – Copy that dispatch, we’re on it.
0:41:19 Remember, never send money online
0:41:22 to people you don’t already know and trust.
0:41:24 – Learn how you can spot the signs of a scam
0:41:26 so you don’t have to call the Safe Squad
0:41:31 by visiting www.box.com/safesquadHQ.
0:41:34 (upbeat music)
0:41:37 – So now you’re one of those guys
0:41:39 who I imagine are listeners,
0:41:41 a lot of young people listen to the pod
0:41:43 who look at your career and think,
0:41:46 “Wow, you shaped a really cool career for yourself.”
0:41:48 Give us a little bit of the origin story
0:41:51 about how you got to where you are.
0:41:53 What do you think the most positive influences
0:41:55 and decisions you made and maybe some of the mistakes
0:41:57 you made because you’ve carved out
0:42:00 a really interesting seat for yourself.
0:42:01 – I appreciate that, Scott.
0:42:03 I mean, I think, look, I think I also got lucky
0:42:05 in a lot of different ways where
0:42:09 I quit my consulting job in 2004 to play poker,
0:42:11 mostly internet poker.
0:42:13 – Were you one of these guys in Costa Rica
0:42:15 that was just online all day long
0:42:16 trying to take advantage of idiots like me
0:42:19 that occasionally play online poker?
0:42:21 – I was living in Chicago, not Costa Rica.
0:42:22 I should probably have played more, right?
0:42:24 I probably should have played like around the clock
0:42:27 ’cause it was a bubble more than a boom.
0:42:28 There were so many new players
0:42:30 that like you were just printing money.
0:42:32 Probably had an expected value of, I don’t know,
0:42:34 150 or 200 bucks an hour,
0:42:35 which is very hard to achieve
0:42:39 when you’re like in your 20s or something.
0:42:40 So I probably should have played even more hours
0:42:42 and grinded even more out.
0:42:44 But what happened instead is that in 2006,
0:42:47 the US Congress passed a law
0:42:49 that basically banned payment processing
0:42:50 to poker sites online.
0:42:53 So basically caused the games to get much worse.
0:42:56 Now you had to have a shady workaround
0:42:57 to deposit your money.
0:43:01 And so some of the weaker players left the game and so,
0:43:05 but that actually sparked my interest in politics.
0:43:08 And it’s 2008, I’m living in Chicago.
0:43:10 There’s a youngish guy named Barack Obama
0:43:12 who went to, not went to,
0:43:14 taught at my university, University of Chicago,
0:43:15 who’s running for president.
0:43:18 Meanwhile, this is kind of five years after Moneyball
0:43:20 and it’s a time for the moneyballization of everything.
0:43:23 So, you know, had time for, with my poker career,
0:43:25 having dried up, I had time for something else
0:43:28 and started 538.
0:43:31 And so there was a lot of luck and a lot of serendipity.
0:43:33 But, you know, but you look,
0:43:34 doing something you’re passionate about
0:43:36 and where your incentives are aligned,
0:43:40 I become like, like literally like free access productive.
0:43:43 I think, you know, I mean, like, I get a lot done
0:43:45 over the course of a day or course of a week.
0:43:46 And like, it’s not like I’m, you know,
0:43:48 I’m not necessarily working 24/7.
0:43:52 I leave time for socializing and things like that.
0:43:53 But kind of owning your own work project.
0:43:55 And by the way, I mean, the biggest mistake I think I made
0:43:58 was going and having 538 be attached
0:44:02 to like a giant corporation called the Walt Disney Company
0:44:03 for 10 years.
0:44:07 They were offering a guaranteed paycheck,
0:44:08 but no actual business plan,
0:44:12 no actual incentive compensation or anything like that.
0:44:13 And I did work really hard for them
0:44:17 for probably the first eight and a half out of those 10 years.
0:44:18 But now that I’m back on my own
0:44:21 and have a newsletter subscription business
0:44:25 and have my own podcast and do some consulting on the side,
0:44:28 you know, it turns out that actually I’m doing
0:44:30 a lot better financially than they were paying me
0:44:33 because the incentives are there and because like, you know,
0:44:35 I kind of own my own image and work product.
0:44:37 And it’s just way more,
0:44:38 it’s way more of my speed
0:44:40 to be a little bit more entrepreneurial.
0:44:43 I’m not quite sure what I was expecting to get
0:44:45 out of the big kind of corporate experience.
0:44:48 – And just as we wrap up here,
0:44:50 given what you know about, you know,
0:44:53 you write about politics, you write about technology,
0:44:55 your advice to someone just coming out of school
0:44:57 or a younger person, where do you think,
0:44:59 when you look at different industries,
0:45:01 do you think that someone who’s risk aggressive
0:45:04 in this industry could do very well
0:45:06 or sort of advice to your 25 year old self,
0:45:09 what would those industries or those jobs be?
0:45:11 – I think being differentiated,
0:45:14 maybe that’s a slightly too generic piece of advice,
0:45:17 but, you know, finding things that you’re passionate about
0:45:20 and things that you do like uniquely well, right?
0:45:22 You know, if you can be the best person ever writing
0:45:25 about, you know, women’s curling or something like that,
0:45:27 then it probably won’t be a career for you,
0:45:29 but you at least positively differentiate yourself.
0:45:31 One of the smartest things I did for the book, by the way,
0:45:34 is just kind of talking to smart people a lot.
0:45:36 So, you know, having good conversations,
0:45:37 but I think we’re in a world now
0:45:40 where particularly with the rise of AI,
0:45:43 and I’m kind of a, you know, I’m not like a AI doomer.
0:45:45 I’m also not an AI is going to conquer everything person.
0:45:48 I’m kind of uncertain about it,
0:45:50 but I think that will increase the premium
0:45:52 on not being average,
0:45:55 ’cause the AI will give you like a very good
0:45:57 above average version of average, if that makes sense, right?
0:46:00 It can kind of synthesize all the text on the internet
0:46:02 and put it together in a way that’s a little bit dry
0:46:05 and boring, but, you know, plausibly pretty good.
0:46:08 And so, do you kind of provide like a unique vector,
0:46:11 I guess, in the world that can’t be replicated anywhere else?
0:46:13 I think that’s a valuable skill.
0:46:14 – Yeah, I like what you said there.
0:46:18 I’ve always found that the specific crowds of the general
0:46:20 and commit to owning something,
0:46:22 like you said, women’s curling, commit to being,
0:46:23 you might think that’s too niche,
0:46:25 but if you’re the best in the world at covering it,
0:46:27 then eventually you’ll start covering ice skating
0:46:29 or something or people will want to have your,
0:46:32 know your take on different things.
0:46:34 Nate Silver is the founder of 538
0:46:36 and the author of the New York Times bestselling book,
0:46:38 The Signal and the Noise.
0:46:41 He also writes the sub-stack, Silver Bulletin.
0:46:42 His latest book, On the Edge,
0:46:45 The Art of Risking Everything, is out now.
0:46:49 He joins us from his home in Chelsea, adjacent.
0:46:51 Nate, I really enjoyed this conversation
0:46:53 and congrats on your success.
0:46:54 – Thanks so much, Scott.
0:46:55 It was great.
0:46:55 Talk to you soon.
0:46:58 (upbeat music)
0:47:04 – This episode was produced by Caroline Shagren.
0:47:06 Jennifer Sanchez is our associate producer
0:47:08 and Drew Burroughs is our technical director.
0:47:09 Thank you for listening to The Property Pod
0:47:11 from the Vox Media Podcast Network.
0:47:13 We will catch you on Saturday
0:47:15 for No Mercy, No Malice as read by George Hahn.
0:47:18 And please follow our Property Markets Pod
0:47:20 wherever you get your pods for new episodes
0:47:22 every Monday and Thursday.
0:47:25 – Thanks to Huntress for their support.
0:47:27 Keeping your data safe is important.
0:47:29 However, if you’re a small business owner,
0:47:31 then protecting the information of yourself,
0:47:34 your company and your workers is vital.
0:47:36 In comes Huntress.
0:47:39 Huntress is where fully managed cybersecurity
0:47:41 meets human expertise.
0:47:44 They offer a revolutionary approach to manage security.
0:47:46 That isn’t all about tech.
0:47:49 It’s about real people providing real defense.
0:47:51 When threats arise or issues occur,
0:47:53 their team of seasoned cyber experts
0:47:58 is ready 24 hours a day, 365 days a year for support.
0:48:02 Visit huntress.com/vox to start a free trial
0:48:03 or learn more.
0:48:06 (upbeat music)
0:00:05 the AI platform for business transformation.
0:00:07 You’ve heard the big hype around AI.
0:00:09 The truth is AI is only as powerful
0:00:11 as the platform it’s built into.
0:00:13 ServiceNow is the platform that puts AI
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0:00:24 to make customers happier.
0:00:27 All built into a single platform you can use right now.
0:00:29 That’s why the world works with ServiceNow.
0:00:33 Visit servicenow.com/aiforpeople to learn more.
0:00:38 – I’m Anusa Ramonyan from Vox Media.
0:00:40 While I see them all around the city,
0:00:43 I’ve never ridden in an autonomous vehicle myself.
0:00:45 I do have some questions about the tech.
0:00:46 You may as well.
0:00:48 – Hello, from Waymo.
0:00:50 This experience may feel futuristic.
0:00:52 – This is so cool.
0:00:55 – Vox and Waymo teamed up for an in-depth study
0:00:57 about AV perception.
0:00:59 And what they found was that as people learned more
0:01:01 about Waymo, their interest in choosing one
0:01:04 over a human-driven vehicle almost doubled.
0:01:06 – Person approaching.
0:01:10 – Waymo can see 360 degrees and up to 300 meters away,
0:01:12 which helps it obey traffic laws
0:01:14 and get you where you’re going safely.
0:01:16 Swiss Re found that compared to human drivers,
0:01:20 Waymo reported 100% fewer injury claims
0:01:23 and 76% fewer property damage claims.
0:01:26 And speaking of safety, folks identifying as LGBTQIA
0:01:30 and non-binary showed the highest interest in AVs.
0:01:32 And women showed the greatest increase in interest
0:01:33 after learning more.
0:01:37 – Arriving shortly at your destination.
0:01:40 – So that actually felt totally normal.
0:01:42 AVs are here, and the more you know,
0:01:44 the more exciting this tech becomes.
0:01:46 You can learn more about Waymo,
0:01:48 the world’s most experienced driver,
0:01:50 by heading to Waymo.com.
0:01:53 – Episode 312, 312 is a year ago,
0:01:54 belonging to Chicago, Illinois.
0:01:57 In 1912, the Titanic hit an iceberg and sank.
0:02:01 And the Girl Scouts of the USA were founded.
0:02:03 Why do Girl Scout cookies taste so good?
0:02:05 Job labor.
0:02:09 Go, go, go!
0:02:12 (upbeat music)
0:02:19 – Welcome to the 312th episode of the Proxy Pot.
0:02:23 The dog is on vacation for the rest of August.
0:02:24 We’re gonna go to one of those dog farms
0:02:26 where I play with 30 other dogs,
0:02:27 roll around in deer urine.
0:02:30 You know, the usual, August, Augusto.
0:02:32 All month long on Thursdays,
0:02:34 you can expect conversations with blue flame thinkers,
0:02:37 innovators, professors, authors, and the like.
0:02:40 I didn’t write that, I would never say and the like.
0:02:42 Today, we’re sharing our interview with Nate Silver,
0:02:45 the founder of 538 and the New York Times bestselling author
0:02:47 of The Signal and the Noise.
0:02:50 He also writes the sub-stack, Silver Bulletin.
0:02:53 We discussed with Nate his latest book On the Edge,
0:02:55 The Art of Risking Everything.
0:02:56 I could write a book called On the Edge
0:03:00 about fucking depression, anxiety, and turning 50
0:03:02 and looking like you’re fucking 80 years old.
0:03:05 That’s what it would mean to be on the edge, Nate.
0:03:07 Anyway, we hear about the role of risk
0:03:10 in shaping modern life, his background in election forecasting,
0:03:14 and his thoughts on Kamala Harris’s VP pic.
0:03:17 Oh, that’s kinda, that’s what you call timely.
0:03:19 That’s why you come to the Prop G pod.
0:03:21 That’s why you come to the PGP, if you will.
0:03:24 We really enjoyed this conversation
0:03:26 and thank you, Will, as well.
0:03:30 Nate, where does this podcast find you?
0:03:31 – At home in New York, Manhattan.
0:03:33 – You live in the city, where do you live in the city?
0:03:35 – What would charityally be called Chelsea?
0:03:38 Kinda by Penn Station, Madison Square Garden, basically.
0:03:41 – So let’s talk about your new book On the Edge,
0:03:43 The Art of Risking Everything.
0:03:47 You investigate the river, the community of like-minded people
0:03:49 whose mastery of risk allows them to shape
0:03:52 and dominate so much of our modern world.
0:03:54 Can you explain what you mean by the river?
0:03:57 – So I have a very kind of geographic mind.
0:03:59 I like a good geographic memory
0:04:01 and I like looking at maps and things like that.
0:04:05 So I kinda wanted to create a metaphorical place
0:04:07 where a certain type of person lives.
0:04:09 And this type of person has two
0:04:10 basically defining characteristics.
0:04:12 One is that they’re super analytical.
0:04:16 They’re kind of in the moneyball, math nerd tradition
0:04:17 for the most part, so they’re playing poker
0:04:20 or founding companies or things like that.
0:04:25 The other is that they’re extremely insanely competitive,
0:04:28 which makes them really risk taking for the most part.
0:04:30 They wanna win, they wanna prove things to themselves
0:04:32 and other people.
0:04:34 They aren’t afraid to stand out.
0:04:37 They can be contrarian to the point of sometimes being
0:04:39 more than a bit annoying, I think.
0:04:42 But I kept finding the same personality type
0:04:43 in all the different fields that I cover.
0:04:46 I mean, I kind of started in the world of poker.
0:04:48 I actually have a background as a professional poker player.
0:04:51 But if you talk to people in Silicon Valley
0:04:56 or people trading crypto or people making sports bets
0:04:58 or even the effective altruists who we’ll talk to
0:05:01 a little bit later and the AI people,
0:05:04 they all have this kind of same competitive nerd
0:05:06 analytical personality in mind.
0:05:09 They speak the same language and it’s a small community.
0:05:14 The river is a community of mostly successful elites,
0:05:15 I guess you’d call them.
0:05:16 And you go to Silicon Valley,
0:05:18 it’s kind of a small world still.
0:05:21 It’s not sprawling through thousands of people.
0:05:24 The top VC firms might have a dozen partners or something,
0:05:25 but not hundreds.
0:05:29 And so there’s more community than I would have thought.
0:05:32 And you’ve seen that community have a rivalry more and more
0:05:34 with this other community that I call the village.
0:05:37 – And talk about the distinction between folks in the river
0:05:39 and folks in the village.
0:05:42 – Yeah, so the village is basically,
0:05:44 if you think of it as kind of New York, Boston, Washington,
0:05:45 maybe except for like Wall Street.
0:05:49 So it’s like government, media and academia.
0:05:52 So the kind of quintessential river village rather institutions
0:05:55 are like Harvard University and the New York times.
0:05:58 So it’s politically progressive for the most part.
0:06:02 As compared to the river, it’s much less analytical.
0:06:06 In fact, it’s very concerned about social status
0:06:07 and social appearances.
0:06:10 The ultimate punishment in the village
0:06:12 is to be ostracized or I suppose canceled.
0:06:15 That’s becoming a little bit outmoded.
0:06:17 And it’s risk averse.
0:06:18 It’s kind of neurotic.
0:06:20 It was much more cautious during COVID.
0:06:22 It’s afraid of offending people.
0:06:25 And there’s a rivalry between these two communities
0:06:27 increasingly when you see things like,
0:06:30 I guess it was last year, maybe in January,
0:06:32 when you see like hedge fund investors attacking
0:06:35 like university presidents who are speaking before Congress,
0:06:37 that’s an open conflict, I would say.
0:06:40 When you see people in Silicon Valley
0:06:41 kind of going more to war
0:06:44 with like the Democratic Party establishment,
0:06:46 we’re actually seeing this kind of play out more and more.
0:06:48 – I mean, I’m loosely the words that come into my mind
0:06:51 are kind of libertarian versus establishment.
0:06:52 Is that fair?
0:06:54 – I think the river would champion itself
0:06:57 as kind of lowercase L libertarian.
0:07:01 And would champion itself as being apolitical,
0:07:03 but of course it’s often hypocritical.
0:07:06 People go from being apolitical to being like Elon Musk,
0:07:10 or you’re very politically charged up on a lot of issues.
0:07:13 I mean, if you did a survey of the people I call riverians,
0:07:16 they’d probably be three to two Democratic
0:07:18 before Republicans still, or two to one maybe.
0:07:21 It’s, I mean, most communities of elites today
0:07:23 where you have high educational credentials
0:07:25 tend to be Democrats in the United States,
0:07:28 but it’s notably more varied than the village,
0:07:33 which is kind of uniformly 95% blue Democratic progressive.
0:07:36 – Talk about what you think are the key habits
0:07:38 of highly effective risk takers
0:07:39 that you talk about in your book.
0:07:41 – There’s a list of 13 of these in the book,
0:07:45 and they kind of fall somewhat into personality characteristics
0:07:48 and somewhat into psychological characteristics.
0:07:50 From a psychological standpoint,
0:07:53 some degree of detachment,
0:07:56 where you’re focused on process and not results.
0:07:59 If you play a poker hand, you can play the hand perfectly.
0:08:01 And if your opponent makes her flush draw,
0:08:04 you’re still gonna lose that hand a third of the time.
0:08:06 That process orientation, I think,
0:08:08 is counterintuitive for most people.
0:08:10 Personality wise, some of it does come down
0:08:14 to simply being willing to take risks and being courageous.
0:08:16 Maybe the single most important defining characteristic
0:08:20 is being cool under pressure in most walks of life.
0:08:23 Higher stakes moments vastly outweigh the day to day.
0:08:25 If you do make it deep in a poker tournament
0:08:27 playing for a million dollar first prize,
0:08:30 it’s more important by a factor of 1,000 X
0:08:33 than your Tuesday night beer league game, for example.
0:08:35 Learning how to handle pressure is important.
0:08:36 I mean, I did, like I said,
0:08:38 talk to mostly people who are doing
0:08:40 analytic math-oriented things.
0:08:44 But I also talked to an astronaut, an explorer,
0:08:46 a military commander, people like this.
0:08:49 And I heard some of those same things over and over.
0:08:51 One thing I heard a lot is don’t try to be a hero
0:08:52 when you’re under pressure,
0:08:54 when you’re like literally in outer space
0:08:57 and some red light is blinking.
0:09:01 Trusting the process, following protocol,
0:09:03 that kind of frees up bandwidth
0:09:05 for dealing with an emergency versus just like winging it.
0:09:08 So it’s a lot of preparation and experience
0:09:10 and coolness under fire.
0:09:12 – It’s interesting because, well,
0:09:15 the way I would try and translate that to entrepreneurship
0:09:19 is I don’t think I’d be nearly as good an entrepreneur now
0:09:20 as I was when I was a younger man.
0:09:22 Because when I was a younger man,
0:09:25 I had a bit of sociopathy in the sense that
0:09:27 it could be awful around me in my business
0:09:30 and we were running out of funding.
0:09:31 And I’d be stressed,
0:09:33 but I would still be able to sleep at night.
0:09:35 I just didn’t, I didn’t,
0:09:37 I was almost sort of sleepwalking through life and didn’t,
0:09:40 and now I’m too anxious.
0:09:42 I’m too kind of concerned about the downside.
0:09:45 Do you think there’s any truth in that?
0:09:46 – For sure.
0:09:49 I think it’s not a coincidence that more founders are younger,
0:09:50 although there’s probably some stereotyping
0:09:52 that takes place some of you sees.
0:09:54 Poker players are often younger too,
0:09:57 despite it being a game that it takes a lifetime to master.
0:10:00 That’s partly also a matter of physical fitness, I think.
0:10:03 But yeah, the ability to like shut out distractions
0:10:05 and be really focused is really hard
0:10:10 and maybe not entirely healthy sometimes either.
0:10:12 But yeah, as you gain more responsibilities, right?
0:10:15 So I played as I do most years,
0:10:17 I went to the World Series of Poker this year and played,
0:10:19 but it’s an election year.
0:10:20 I have this book coming out.
0:10:23 So there were like constant distractions
0:10:26 and it was in my best interest to manage those, right?
0:10:29 I can write newsletter posts and gain subscribers
0:10:32 or book interviews and publicity for the book.
0:10:34 But still, yeah, part of what comes with being an adult,
0:10:36 I think, is you have a little bit more to lose.
0:10:38 That can make you more risk-averse,
0:10:40 you have more responsibilities, and that can be okay.
0:10:43 But if you’re a VC trying to invest in a founder,
0:10:46 you want a founder who has kind of literally
0:10:50 insane single-minded focus, maybe for a period of 10 years,
0:10:52 whatever runway period that you have,
0:10:54 and that not be a younger person’s game.
0:10:58 – People thought people are risk takers and are successful,
0:11:00 are good at taking smart risks.
0:11:02 In other words, to a certain extent,
0:11:06 the risks they take, they do the analysis and go,
0:11:08 there’s a greater upside here that,
0:11:10 you know, a one in betting on a team
0:11:13 that has a 50 to one chance, you get 50 to one odd,
0:11:16 seems like crazy risk, but if you actually have done
0:11:18 the analysis and say the likelihood is more like 30 to one,
0:11:21 that’s a good risk, how would you coach young people
0:11:24 around how they approach risk?
0:11:26 – I think probably 90% of people,
0:11:28 of course, in your probability,
0:11:30 I think probably 90% of people could stand
0:11:34 to be more risk-taking, at least in terms of like
0:11:36 their career lives.
0:11:38 I’m not saying, oh, go do drugs or something like that,
0:11:39 that’s a personal choice.
0:11:41 You know, look, we have a lot of evolutionary training
0:11:44 where we don’t live in this kind of world of abundance
0:11:48 that we do now, where we don’t have as much of a safety net
0:11:50 if you fail, and where there was less of a war
0:11:52 for taking risks, you go out and get some infection
0:11:54 or something, and there’s no cure for it,
0:11:56 then you die, and now we’re in a world of abundance
0:12:00 and we can afford to think more in terms of expected value,
0:12:04 which means kind of, what is the outcome you get on average
0:12:05 when trying this thing?
0:12:07 ‘Cause there’s uncertainties in the world.
0:12:09 If you play poker, then some percentage of time
0:12:10 you’re gonna win the tournament,
0:12:12 more often than not, you bust out,
0:12:14 but are you making, or is it a plus EV,
0:12:16 positive expected value gamble on average?
0:12:19 Now, if you’re a founder and you’re making these
0:12:21 long, prolonged, 10-year bets,
0:12:22 then maybe it’s a little bit different, right?
0:12:24 I mean, the kind of brilliant thing
0:12:26 that venture capitalists do is they gather together
0:12:29 all these founders who are making long shot bets
0:12:30 with probably positive expected value,
0:12:33 but many of them will fail.
0:12:34 If you make enough of those bets,
0:12:36 then you’re kind of guaranteed
0:12:38 to do very well for yourself, right?
0:12:40 Enough of them will pay off in a,
0:12:43 you have a fund of 15 or 20 or 25 companies every year,
0:12:45 then sooner, and you have your pick of the litter,
0:12:47 you’re picking the best founders,
0:12:49 then that’s a very good business.
0:12:50 For a founder, it requires, I mean,
0:12:53 I think it literally does require more risk.
0:12:55 I mean, if you are any one founder,
0:12:57 your company may fail,
0:12:59 which is partly why, you know,
0:13:01 you get people like Elon Musk,
0:13:03 who like literally, if you read the,
0:13:07 the Isaacson book on him about Elon playing poker,
0:13:09 he would like literally just kind of go in,
0:13:12 go all in every hand until he’d lose
0:13:14 and he’d walk away from the table and do something else.
0:13:16 He’s not 10% group where he’s probably taking
0:13:19 on too much risk, I would think,
0:13:21 but these are often people that have chips on their shoulder
0:13:23 that almost have like an evolutionary
0:13:27 or genetic kind of propensity to take risk.
0:13:29 – Yeah, I wonder if they’re to a certain extent,
0:13:29 I’m not talking about Elon Musk,
0:13:33 but they have their addicts in the sense that
0:13:36 they take risk and the new kind of the new dopamine balance
0:13:41 after taking some risk is to have that rush
0:13:42 you have to take more risk.
0:13:45 I used to, I worked for a hedge fund manager
0:13:48 who at one point was the, I think the 50th
0:13:51 or the 70th wealthiest person
0:13:55 and he kept taking these just outsize crazy risks
0:13:57 until he ended up broke.
0:14:01 And he just has like almost a psychotic approach
0:14:05 or aggressive approach to risk.
0:14:07 I want to bring it down to entrepreneurship
0:14:10 because I’ve been an entrepreneur for most of my life
0:14:12 and it raised a lot of money from VCs.
0:14:14 And where I thought there was a bit of a disconnect
0:14:17 or dislocation between their interests and my interest
0:14:21 is that they would always encourage me as the CEO
0:14:23 or the founder of a company when I was going well
0:14:25 to go bigger, harder, bolder
0:14:29 because they’re looking for billion dollar exits
0:14:33 to pay for the 70 or 80% of their portfolio
0:14:35 that doesn’t even get its money back
0:14:38 and half of them that go to zero.
0:14:39 And they need those big pops.
0:14:43 And I was thought, okay, I don’t need to be a billionaire.
0:14:45 I need to have economic security
0:14:46 and this is where our interests diverge
0:14:48 because I used to advocate for
0:14:51 and usually would ultimately would win
0:14:53 for selling the company.
0:14:55 I sold my first company for 33 million.
0:14:56 Our investors were disappointed.
0:14:59 I sold my last company for 160 million
0:15:02 despite my investors tripling their money in 27 months.
0:15:04 They were disappointed
0:15:06 because I didn’t have a bunch of chips on the table.
0:15:09 I had one big chip on one number.
0:15:12 And so it creates a divergence of risk.
0:15:15 Can you talk a little bit about where, you know
0:15:17 are there other divergences, whether it’s an employee
0:15:19 and you’re, you know
0:15:22 of a company or an entrepreneur or founder and VCs
0:15:26 how do you want to be thinking about an approach to risk
0:15:28 based on where you are in an organization?
0:15:30 – No, Scott, I think that’s right.
0:15:33 And I think kind of VCs get the better side
0:15:37 of that VC founder interaction most of the time.
0:15:39 And it’s probably why they’re picking people
0:15:43 who have huge variants in their outcomes, right?
0:15:44 You’re not going to pick somebody
0:15:48 to run like a chain of three ice cream stores
0:15:49 in Boise, Idaho or something, right?
0:15:50 Where the upside is capped.
0:15:53 You want people that wind up on the extreme tails
0:15:54 because the thing you hear over and over and over again
0:15:56 from everyone in Silicon Valley is like
0:16:00 you can’t miss out on the 1000X X and your money opportunity.
0:16:03 You cannot let Mark Zuckerberg walk through the door.
0:16:05 So the downside of that is you sometimes get a Mark Zuckerberg
0:16:07 and sometimes you get a Sam Bakeman Fried
0:16:09 or Elizabeth Holmes or whatever else.
0:16:12 I mean, even in my own world, you know
0:16:15 I kind of run I guess my own content business
0:16:17 and realizing that it’s actually a much better business
0:16:19 where it’s smaller scale, right?
0:16:21 I keep more of the profit myself.
0:16:22 I don’t have a bunch of employees
0:16:26 whose marginal contribution can be debated, I suppose.
0:16:28 And so yeah, I found that when I’m smaller
0:16:31 I actually am happier and more successful financially
0:16:32 but the obsession with scale
0:16:34 especially in the media business
0:16:36 which is maybe its own special beast
0:16:38 but the obsession with scale makes sense
0:16:40 in most contexts from a VC standpoint
0:16:43 but may not be in the interest of the founder.
0:16:46 – In terms of your own personal life and risk taking
0:16:50 I’ve always bifurcated it and it may be incorrect
0:16:51 but again, just trying to reverse engineer this
0:16:54 into actionable advice for young people.
0:16:58 There was my risk profile before kids and then after kids
0:16:59 and I left investment banking
0:17:02 which on a risk adjusted basis was what I should have stuck
0:17:05 with but I wasn’t enjoying it and I wasn’t very good at it.
0:17:08 And then I moved home with my mom because I’m like
0:17:10 oh, I don’t know what I’m gonna do
0:17:12 and not knowing what you wanna do and quitting
0:17:15 doesn’t pay well so I moved back in with my mom
0:17:17 and I took risks and I applied to graduate school
0:17:20 started businesses, my first business
0:17:23 I didn’t have any money but my girlfriend was making money
0:17:26 so I could take that risk.
0:17:30 Once I had kids and I think this is the correct instinct
0:17:32 I’m like okay, shit just got real.
0:17:36 My, you know, me and my two sons can’t move back in
0:17:39 but my mom or it’s gonna be very uncomfortable
0:17:42 and it absolutely changed my risk profile.
0:17:44 A lot more anxiety, a lot more concern around risk
0:17:46 but I think that was the correct emotion.
0:17:50 Would you describe other seminal moments in your life
0:17:52 that you wanna think about risk before and after
0:17:54 and doesn’t this all add up to when you’re young
0:17:56 is the time to take risks?
0:17:59 – I think so, I mean, I don’t have kids
0:18:01 and so that’s like one more reason to kind of gamble
0:18:04 on your upside and not necessarily worry
0:18:06 about a secure paycheck, I don’t think.
0:18:08 Yeah, I think that heuristic is basically right
0:18:10 that when you’re younger you have more opportunity.
0:18:14 I mean, look, I think people sometimes set the bar too low
0:18:17 as far as life outcomes that they’re satisfied with
0:18:19 because my first job out of college
0:18:21 I had a consulting job, I was something called
0:18:23 a transfer pricing consultant
0:18:25 which is about as boring as it sounds like
0:18:28 and quit that to play online poker basically
0:18:29 where I was making more money
0:18:31 and to work for a internet startup
0:18:33 that wrote about baseball statistics.
0:18:38 So quitting a safe consulting job is a somewhat risky endeavor
0:18:39 but it proved to be a better decision
0:18:43 and I think people need to have a higher reserve price
0:18:44 to use a slightly technical term
0:18:47 for how they’re spending their time.
0:18:49 There’s also studies, I mean, Stephen Leavitt
0:18:51 of Freakonomics did a famous paper
0:18:55 where he would actually have people literally flip coins
0:18:56 to make major life decisions.
0:18:59 So should I move across the country or quit my job
0:19:01 or get divorced or get married
0:19:03 and found that when people flipped a coin
0:19:05 they told them to make a change
0:19:07 they wound up being happier on average.
0:19:09 The importance of quitting.
0:19:10 I don’t know if you had Annie Duke on the show
0:19:13 former poker player who now writes business books
0:19:15 wrote a book called quit.
0:19:18 Getting out of a bad situation while you can
0:19:23 or maybe half a move ahead is an underrated skill I think.
0:19:25 I think people are too willing to muddle through
0:19:27 not have a long enough time horizon
0:19:30 and wind up being mired in an unhappy place.
0:19:32 – I think that’s a great insight
0:19:33 and I just wanted to stop on that.
0:19:36 There’s this mythology from Donald Trump down
0:19:37 and like never give up.
0:19:39 Oh, there’s a time to give up.
0:19:41 I mean, absolutely.
0:19:42 There’s a time to leave.
0:19:44 And I would say that’s where a kitchen cabinet comes in
0:19:46 to advise you that, okay, you’re banging your head
0:19:47 against a wall.
0:19:49 You need to move on to different opportunities.
0:19:51 Several chapters of your book focus
0:19:54 on Sam Bankman Freed and the crypto world.
0:19:56 What do you think people miss about FTX
0:19:59 and Sam Bankman Freed and how it relates to risk?
0:20:03 – So he is certainly on the extreme right tail
0:20:05 of risk-taking where he literally said
0:20:08 in repeated interviews that if he could push a button
0:20:10 and gamble for the future of the universe
0:20:12 and either the universe is destroyed
0:20:15 or 51% of the time it winds up being twice as good
0:20:17 then it’s a positive expected value bet.
0:20:18 So he’d make it.
0:20:21 That’s a pretty insane way to look at life.
0:20:25 And I think people were too unwilling.
0:20:28 I think there was a little bit of a kind of boy genius myth
0:20:30 around Sam.
0:20:31 And there was a little bit of a bystander problem
0:20:34 where it seemed like all these people are vouching for him.
0:20:35 Therefore he must be smart
0:20:39 and therefore people weren’t willing to point out
0:20:41 sometimes crazy and kooky things that he was willing to say.
0:20:44 And it’s a little bit of a cult of personality,
0:20:46 the cult that the village or the river would think it avoids
0:20:48 that actually winds up having with founders
0:20:50 like SPF sometimes.
0:20:53 I think he was also not a very good risk assessor
0:20:55 despite thinking of himself as one.
0:20:59 I talked to a lawyer right as his criminal trial
0:21:01 and Manhattan was taking place.
0:21:04 And the lawyer said he should not take the stand.
0:21:08 He should cut his losses and try to minimize his sentence
0:21:10 at five to 10 years.
0:21:13 If he takes a stand, he’s for sure gonna hurt yourself,
0:21:17 which he did and he wound up getting like 20 years instead.
0:21:20 When I talked to Sam and Palo Alto six months before the trial,
0:21:24 I said, what if you were offered a two year plea deal,
0:21:27 two years and then some restrictions
0:21:28 on what you can do afterwards.
0:21:30 So kind of more than a slap on the wrist,
0:21:31 but not that much more.
0:21:33 And he said, I’d have to think about it, right?
0:21:35 So I mean, he was 10 X off
0:21:36 of what the realistic outcome was gonna be.
0:21:38 He got 20 years of course.
0:21:41 And I think, I think, look, as a poker player,
0:21:44 I’ve seen lots of people in the SPF typology.
0:21:49 So kind of smart, nerdy, maybe a little bit on the spectrum,
0:21:53 you know, neurotic, Adderall, whatever quick on his feet.
0:21:58 And not all of them are as smart as they’re cracked up to be.
0:22:01 So I think people needed to have more skepticism of him
0:22:04 both kind of before, during and after the bankruptcy.
0:22:06 – I would argue that’s a perfect example
0:22:10 of just ridiculously stupid risk-taking.
0:22:13 I can’t imagine how frustrated his lawyers must have been.
0:22:16 Like, okay, you are doing everything wrong here.
0:22:19 I’m curious, have you tried to relate some of your thoughts
0:22:21 and analysis around risk-taking
0:22:24 to people’s relationships or personal life?
0:22:25 You said you don’t have kids.
0:22:26 I don’t know if you’re in a partnership,
0:22:29 but have you thought about approach to risk
0:22:33 as it relates to relationships and outcomes?
0:22:36 – Yeah, I’ve been a long-term relationship, no kids.
0:22:37 I guess I’d say, frankly, not as much.
0:22:40 I mean, I’m trying to keep, it’s already a long book.
0:22:41 It’s like 500 pages.
0:22:43 So I’m trying to keep the scope of it somewhat narrow.
0:22:48 I think some of it does apply that people, you know,
0:22:52 probably are settle a little bit too easily sometimes.
0:22:55 I think the importance of what I call,
0:22:57 or not what I call the importance of optionality,
0:22:59 I think is really important in both business
0:23:01 and interpersonal affairs,
0:23:03 where are you walking down a hallway
0:23:06 where there are a lot of doors open, right?
0:23:08 It’s kind of a stupid analogy,
0:23:11 but, you know, I’ve lived in New York for 15 years now,
0:23:13 so my partner and I, we have a, you know,
0:23:14 pretty good group of friends.
0:23:16 And so let’s say you don’t have plans
0:23:19 on a Thursday night, well, there’s a whatever,
0:23:22 one in three chance that someone will text you and say,
0:23:24 “Hey, I just have made a reservation
0:23:25 “on this new dinner place,
0:23:28 “or you want to go to the Yankees game.”
0:23:30 Just these kind of cool opportunistic things.
0:23:32 Let’s go to an art gallery that you don’t have
0:23:35 if you haven’t facilitated different options in your life.
0:23:38 – We’ll use the word optionality.
0:23:40 You’re an analytics guy.
0:23:42 Do you think it makes sense to get married?
0:23:44 We’ll be right back.
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0:25:38 – I’m Anusa Brahmanyan from Vox Media.
0:25:39 While I see them all around the city,
0:25:42 I’ve never ridden in an autonomous vehicle myself.
0:25:44 I do have some questions about the tech.
0:25:45 You may as well.
0:25:48 – Hello, from Waymo.
0:25:50 This experience may feel futuristic.
0:25:51 – This is so cool.
0:25:54 – Vox and Waymo teamed up
0:25:56 for an in-depth study about AV perception.
0:25:57 And what they found was that,
0:25:59 as people learned more about Waymo,
0:26:01 their interest in choosing one
0:26:04 over a human-driven vehicle almost doubled.
0:26:05 – Person approaching.
0:26:09 – Waymo can see 360 degrees and up to 300 meters away,
0:26:11 which helps it obey traffic laws
0:26:13 and get you where you’re going safely.
0:26:16 Swiss Re found that, compared to human drivers,
0:26:19 Waymo reported 100% fewer injury claims
0:26:22 and 76% fewer property damage claims.
0:26:23 And speaking of safety,
0:26:27 folks identifying as LGBTQIA and non-binary
0:26:29 showed the highest interest in AVs
0:26:31 and women showed the greatest increase in interest
0:26:32 after learning more.
0:26:36 – Arriving shortly at your destination.
0:26:40 – So that actually felt totally normal.
0:26:41 AVs are here and the more you know,
0:26:44 the more exciting this tech becomes.
0:26:46 You can learn more about Waymo,
0:26:48 the world’s most experienced driver
0:26:49 by heading to Waymo.com.
0:26:54 – We’ll use the word optionality.
0:26:55 You’re an analytics guy.
0:26:58 Do you think it makes sense to get married?
0:27:01 – Probably for tax purposes and stuff like that.
0:27:02 I mean, there’s still,
0:27:04 probably my partner and I should think about it
0:27:05 at some point.
0:27:09 Yeah, I think there are still benefits
0:27:12 from being married in terms of just the way
0:27:13 the tax code tweets it and things like that,
0:27:16 which, you know, was like a very, very clinical answer.
0:27:19 You know, I do think sometimes commitment is also,
0:27:20 can also be a good thing.
0:27:23 I mean, I think there can be paradoxes of choice
0:27:25 where you have too many options.
0:27:28 That’s actually kind of one thing I worry about out there
0:27:29 in the world a little bit is that like,
0:27:30 if you’re somebody who’s really good
0:27:32 at taking advantage of optionality,
0:27:35 then the world’s kind of your oyster now, right?
0:27:38 Now you can work from home and have five different jobs,
0:27:39 which I kind of do now.
0:27:41 And it’s like, but it’s a lot to balance.
0:27:43 And if you’re under duress, right?
0:27:46 If you do have kids or an older relative
0:27:48 that you’re taking care of,
0:27:52 if you’re injured somehow or incapacitated somehow,
0:27:54 then it becomes a lot harder potentially.
0:27:57 So I wonder if it leads to like a little bit more of a,
0:27:59 even though like Scott, you might take advantage of it
0:28:01 or I might, I wonder if it leads to a little bit more
0:28:04 of like kind of a winner take all world.
0:28:06 – I think you see that on online dating.
0:28:09 It’s great to be, I mean,
0:28:11 there’s income inequality and I’m crazy in online dating.
0:28:15 My understanding is the top 10% of most attractive males,
0:28:18 if you will, to get 80% of the opportunities.
0:28:20 – Oh yeah, that wouldn’t surprise me one bit.
0:28:22 And then in some sense, I mean, look,
0:28:26 the capitalist internet driven economy
0:28:28 is extremely effective at delivering
0:28:30 whatever the efficient outcome is.
0:28:33 And mostly speaking, I am pro market,
0:28:34 but like we should think about situations
0:28:36 where the efficient outcome,
0:28:39 the market efficient outcome is like not serving
0:28:40 the greater good necessarily.
0:28:42 And that might eventually kind
0:28:45 of market correct itself somehow.
0:28:47 I’m not quite sure how I’ve been in the same relationship
0:28:49 for a long time now.
0:28:52 But yeah, that’s a great microcosm of it, I agree.
0:28:55 – So let’s shift to politics.
0:28:57 So Nate, who’s gonna win the election?
0:28:59 How’s that?
0:29:00 Let’s kick off there.
0:29:01 Who do you think’s gonna win?
0:29:04 – I can give you the honest dodge,
0:29:06 which is our model as of this morning we’re taping this.
0:29:08 It’s about literally about 50/50.
0:29:12 Joe Biden had been a pretty heavy underdog to Trump
0:29:14 and his position, in fact, was worsening in our model.
0:29:16 He was at about 25%.
0:29:17 I think it might have actually been high.
0:29:19 Given that he, his fundraising had dried up,
0:29:21 that he wasn’t really capable
0:29:22 of running a full-fledged campaign.
0:29:25 With Trump Harris, it’s a lot more even.
0:29:26 It’s important for Democrats to remember
0:29:30 that Democrats have a disadvantage in the electoral college.
0:29:32 So she is a favorite to win the popular vote.
0:29:34 She is ahead for right now
0:29:36 in most polls of the popular vote.
0:29:37 But the electoral college, Pennsylvania,
0:29:40 Wisconsin, Michigan, Georgia, et cetera,
0:29:42 is liable to be very close.
0:29:45 So yeah, I wouldn’t wanna wage her a lot of money
0:29:48 on this currently, but she has had momentum.
0:29:51 I mean, it’s been a pretty good rollout to her campaign.
0:29:55 And by the way, I mean, this was an example
0:29:58 of smart risk-taking from Democrats, right?
0:30:01 Is pushing Biden aside?
0:30:02 And they did push him aside.
0:30:04 I don’t buy this rhetoric at like Biden,
0:30:06 but evidently decided to resign.
0:30:09 I mean, Nancy Pelosi and Chuck Schumer were,
0:30:09 yeah, it was kicked out.
0:30:11 They were pulling every lever they could.
0:30:14 And that’s bold from a party
0:30:17 that’s often kind of triangulating and risk averse.
0:30:21 And so credit to them for giving themselves a 50/50 coin flip
0:30:24 instead of personally, I think, very likely lost with Biden.
0:30:26 Now they have a real chance.
0:30:28 – Speaking of sort of triangulating
0:30:30 and taking the less risky choice,
0:30:32 I was really hoping and thought it would have been
0:30:35 a great move to choose Governor Shapiro as the VP.
0:30:37 And they’ve picked Governor Tim Waltz.
0:30:40 So by the way, I think Briggs Greg sort of like dad energy.
0:30:41 And my guess is they’re banking
0:30:45 that he has regional appeal across the border states.
0:30:47 What are your thoughts on the VP pick?
0:30:49 And do you think it, I mean, at the end of the day,
0:30:54 my guess is that we always tend to overestimate
0:30:55 the impact it’s gonna have.
0:30:57 But what do you think of the Waltz pick relative
0:31:01 to kind of risk-taking and moving her chances up or down?
0:31:05 – No, I’m 100% aligned with that take of your Scott.
0:31:06 I think Josh Shapiro is a star talent
0:31:10 and he’s demonstrated empirically his popularity
0:31:12 in the most important swing state, Pennsylvania.
0:31:13 And Pennsylvania, by the way,
0:31:15 it’s a swing state for a reason, which it has,
0:31:18 it has urban areas, it has some diversity,
0:31:21 it has rural areas, it has suburbs around Philly
0:31:23 and Pittsburgh, obviously.
0:31:25 So he has like an actual demonstrated
0:31:27 empirical track record.
0:31:28 And you know, look, I think Tim Waltz
0:31:31 is a pretty good pick in a vacuum.
0:31:33 But I did think it was a little bit risk averse.
0:31:37 If she was a 70/30 favorite or an 80/20 favorite,
0:31:39 that’s what I thought it might have been right choice.
0:31:41 That’s when it’s like a do no harm choice.
0:31:43 I do think because she’s been moving up,
0:31:47 I mean, I think she maybe overrates the importance
0:31:50 of short-term momentum as opposed to in the long term,
0:31:52 it’s really gonna be nice to have someone
0:31:57 who can lock up Pennsylvania and its 19 electoral votes.
0:32:00 And someone who kind of really gets moderate,
0:32:02 it’s excited because actually the Democratic base
0:32:04 isn’t as large as it once was.
0:32:05 And if you look at the voter registration numbers,
0:32:08 and it’s more even now than it used to be.
0:32:11 And a tie goes to Republicans in Electoral College.
0:32:14 So I don’t think it’s a terrible choice.
0:32:16 I think I give like a B minus C plus.
0:32:18 But I think there was like a slightly riskier
0:32:21 but higher expected value option in Shapiro
0:32:23 that she declined.
0:32:26 – So the Trump campaign calls you,
0:32:27 and then the Harris campaign calls you
0:32:29 and asks for your advice on the two or three things
0:32:32 that you would do in terms of messaging or tactics
0:32:35 to improve their likelihood of a good outcomes.
0:32:37 First do Trump, they call you Nate,
0:32:39 what are your thoughts on what we should be doing
0:32:41 more or less of?
0:32:46 – I’d say lay off the anything involving
0:32:48 race, gender, sexuality.
0:32:51 I think that’s the Trump campaign at its worst
0:32:53 and the temptation to do that with, you know,
0:32:56 black Indian American women as the other nominee,
0:32:57 it must be tempting, you know,
0:32:59 I think Trump has continued to pivot to the center
0:33:03 on abortion to some degree, of course, you know,
0:33:05 his party was happy about Roe v. Wade being overturned,
0:33:07 but he’s tried to downplay that.
0:33:09 And I think in general, moderation is smart.
0:33:12 And I think kind of, you know, focusing,
0:33:14 I think the two big liabilities for Democrats,
0:33:17 maybe three actually, immigration is one.
0:33:18 I still think the economy is potentially
0:33:23 a big liability for Harris and Democrats.
0:33:26 It’s good by some measures, not as good by other measures.
0:33:29 We are, of course, are facing a lot of volatility recently
0:33:31 in the stock market who knows will be up and down
0:33:34 on the day that people are listening to this
0:33:38 and focusing a little bit too on tying Harris to Biden
0:33:40 because Trump was beating Biden by four points
0:33:41 or something like that in national polls
0:33:44 by the time that Biden quit the race,
0:33:46 that she’s been the vice president,
0:33:49 that you don’t get like a race board
0:33:51 once you’ve been the vice president for four years
0:33:53 that you kind of own that track record,
0:33:56 maybe even owns the fact that like Biden’s health
0:33:58 and fitness are things that the White House
0:34:00 has not been entirely straightforward about.
0:34:02 So those seem like it’s pretty basic stuff,
0:34:05 but you know, tax the center, avoid creepy race stuff
0:34:09 and focus on the problem she inherits from Joe Biden.
0:34:10 – Now do Harris.
0:34:12 – Go back in time and pick Shapiro,
0:34:14 but I guess it’s too late for that now.
0:34:17 Like I think they have otherwise run a pretty good campaign.
0:34:21 They have kind of unapologetically triangulated
0:34:23 to the center a little bit more.
0:34:26 They have tried out some new arguments,
0:34:29 this argument about calling Republicans weird, for example.
0:34:32 I’m not sure it’s fantastic and objectively speaking,
0:34:34 kind of most people who are into politics
0:34:36 are pretty weird by the Democrat or Republican,
0:34:39 but it’s a new look and I think she appreciates
0:34:41 or her campaign team appreciates
0:34:44 how much young voters in particular
0:34:45 were tired of the same playbook
0:34:47 for three elections in a row, right?
0:34:50 In 2016, younger voters wanted Bernie,
0:34:51 but it was, oh, you have to hold your nose
0:34:52 and vote for Hillary.
0:34:54 In 2020, they want to Bernie again.
0:34:55 Oh, it’s a pandemic.
0:34:57 You have to hold your nose and vote for Donald Trump, right?
0:35:00 In 2024, no primary process at all.
0:35:04 And, you know, and Democrats were asking way too much
0:35:06 of voters, I think to like, to ignore the fact
0:35:10 that Biden had clearly lost a step or two or three or four,
0:35:12 and it just wasn’t working at all.
0:35:15 And he was losing support among core demographic groups,
0:35:17 like young voters, especially, you know,
0:35:19 younger voters, black voters, Hispanic voters,
0:35:21 Asian-American voters of color.
0:35:24 So I think she’s been pretty smart so far.
0:35:27 Apart from the VP pick, I give her, you know,
0:35:30 a good grade for the first two or three weeks of the campaign.
0:35:31 – So I agree.
0:35:33 I thought Shapiro was a shillin’.
0:35:36 I just looked at all of these boxes he checked,
0:35:39 including, you know, being this incredibly popular governor
0:35:41 that would have delivered whatever it is,
0:35:44 the 19 delegates in a swing state.
0:35:46 Have you done any, my guess is they looked,
0:35:50 they’re hoping that Waltz has that type of appeal
0:35:52 across the region that he helps,
0:35:56 he helps their case in, in Wisconsin and Michigan.
0:35:58 Have you seen any analysis around
0:36:00 whether his popularity in Minnesota,
0:36:02 his cross-border and his regional?
0:36:03 – I tend to doubt it.
0:36:06 I mean, remember, like Wisconsin and Minnesota
0:36:09 are big rivals in football and hockey and things like that.
0:36:14 And even the home state VP effects are fairly small.
0:36:17 I mean, look, I want to read more reporting
0:36:19 on why Shapiro wasn’t chosen.
0:36:22 If they did a bad job of managing the internal process,
0:36:25 then it is like, I think a little bit more worrisome
0:36:26 for Harris, ’cause it certainly seemed
0:36:28 like that was the direction she was leaning.
0:36:31 She scheduled a rally in Pennsylvania
0:36:32 at one point on betting markets.
0:36:35 Shapiro was up to like an 80 or 90% favorite.
0:36:37 So, you know, if they got cold feet,
0:36:40 then I want to, I want to learn more about that.
0:36:41 ‘Cause if you do get cold feet,
0:36:44 I mean, there might have been like better ways
0:36:45 of framing that decision.
0:36:48 I mean, maybe say that Shapiro has some ailing family member
0:36:51 he has to attend to or wants to focus on 2028
0:36:52 or something like that.
0:36:55 But it was pretty strange to like tease
0:36:58 at this kind of obvious-seeming bolder choice
0:37:01 and then kind of losing at the altar.
0:37:03 I think maybe that is a little bit worrisome
0:37:05 for how they managed that, but we don’t know.
0:37:08 I mean, there could have been like a vetting issue.
0:37:11 They also moved up in the polls
0:37:12 with the course of making the pick.
0:37:14 So, they’re a little bit ahead of Trump,
0:37:15 so a little bit behind that might’ve made them
0:37:17 more risk-avers and that’s a bit more rational.
0:37:20 But yeah, it was, you know,
0:37:23 it’s somewhere between it’s fine
0:37:24 and maybe a more major mistake
0:37:25 depending on the reasons behind it.
0:37:27 And, you know, given the timing of the show,
0:37:30 I haven’t had reasons to read much reporting yet
0:37:32 about exactly why she made this move.
0:37:35 We’ll be right back.
0:37:39 Support for Prop G comes from Babel.
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0:39:54 – This is advertiser content from Zell.
0:39:59 – So I’m on this job listing site
0:40:01 and I get a message from a recruiter
0:40:02 for a small shipping company.
0:40:06 The recruiter said all I needed to do was send $500
0:40:10 to cover mandatory software training and job was mine.
0:40:13 – Scams are happening like this more and more
0:40:16 because of the change in technology.
0:40:18 The sky’s the limit on scams.
0:40:20 – So says Deborah Baxley,
0:40:24 a mobile payments and FinTech consultant of over 20 years.
0:40:27 – Never be pushed into a sense of urgency.
0:40:30 Always sit back, think twice.
0:40:32 If something seems too good to be true
0:40:35 or a little bit weird, think about it.
0:40:37 – But there are steps you could take
0:40:38 to help protect yourself.
0:40:41 – You should never give out any, what we call PII
0:40:44 in the industry, personal identifying information,
0:40:46 which includes everything from your mailing address,
0:40:48 your social security number,
0:40:50 any kind of banking information.
0:40:51 – Encountering a crime like this
0:40:56 can be a little disorienting, stranger than fiction even,
0:41:00 almost like you’re in a TV show.
0:41:04 – Come in Safe Squad, we got a 10-3.
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0:41:19 Remember, never send money online
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0:41:31 by visiting www.box.com/safesquadHQ.
0:41:34 (upbeat music)
0:41:37 – So now you’re one of those guys
0:41:39 who I imagine are listeners,
0:41:41 a lot of young people listen to the pod
0:41:43 who look at your career and think,
0:41:46 “Wow, you shaped a really cool career for yourself.”
0:41:48 Give us a little bit of the origin story
0:41:51 about how you got to where you are.
0:41:53 What do you think the most positive influences
0:41:55 and decisions you made and maybe some of the mistakes
0:41:57 you made because you’ve carved out
0:42:00 a really interesting seat for yourself.
0:42:01 – I appreciate that, Scott.
0:42:03 I mean, I think, look, I think I also got lucky
0:42:05 in a lot of different ways where
0:42:09 I quit my consulting job in 2004 to play poker,
0:42:11 mostly internet poker.
0:42:13 – Were you one of these guys in Costa Rica
0:42:15 that was just online all day long
0:42:16 trying to take advantage of idiots like me
0:42:19 that occasionally play online poker?
0:42:21 – I was living in Chicago, not Costa Rica.
0:42:22 I should probably have played more, right?
0:42:24 I probably should have played like around the clock
0:42:27 ’cause it was a bubble more than a boom.
0:42:28 There were so many new players
0:42:30 that like you were just printing money.
0:42:32 Probably had an expected value of, I don’t know,
0:42:34 150 or 200 bucks an hour,
0:42:35 which is very hard to achieve
0:42:39 when you’re like in your 20s or something.
0:42:40 So I probably should have played even more hours
0:42:42 and grinded even more out.
0:42:44 But what happened instead is that in 2006,
0:42:47 the US Congress passed a law
0:42:49 that basically banned payment processing
0:42:50 to poker sites online.
0:42:53 So basically caused the games to get much worse.
0:42:56 Now you had to have a shady workaround
0:42:57 to deposit your money.
0:43:01 And so some of the weaker players left the game and so,
0:43:05 but that actually sparked my interest in politics.
0:43:08 And it’s 2008, I’m living in Chicago.
0:43:10 There’s a youngish guy named Barack Obama
0:43:12 who went to, not went to,
0:43:14 taught at my university, University of Chicago,
0:43:15 who’s running for president.
0:43:18 Meanwhile, this is kind of five years after Moneyball
0:43:20 and it’s a time for the moneyballization of everything.
0:43:23 So, you know, had time for, with my poker career,
0:43:25 having dried up, I had time for something else
0:43:28 and started 538.
0:43:31 And so there was a lot of luck and a lot of serendipity.
0:43:33 But, you know, but you look,
0:43:34 doing something you’re passionate about
0:43:36 and where your incentives are aligned,
0:43:40 I become like, like literally like free access productive.
0:43:43 I think, you know, I mean, like, I get a lot done
0:43:45 over the course of a day or course of a week.
0:43:46 And like, it’s not like I’m, you know,
0:43:48 I’m not necessarily working 24/7.
0:43:52 I leave time for socializing and things like that.
0:43:53 But kind of owning your own work project.
0:43:55 And by the way, I mean, the biggest mistake I think I made
0:43:58 was going and having 538 be attached
0:44:02 to like a giant corporation called the Walt Disney Company
0:44:03 for 10 years.
0:44:07 They were offering a guaranteed paycheck,
0:44:08 but no actual business plan,
0:44:12 no actual incentive compensation or anything like that.
0:44:13 And I did work really hard for them
0:44:17 for probably the first eight and a half out of those 10 years.
0:44:18 But now that I’m back on my own
0:44:21 and have a newsletter subscription business
0:44:25 and have my own podcast and do some consulting on the side,
0:44:28 you know, it turns out that actually I’m doing
0:44:30 a lot better financially than they were paying me
0:44:33 because the incentives are there and because like, you know,
0:44:35 I kind of own my own image and work product.
0:44:37 And it’s just way more,
0:44:38 it’s way more of my speed
0:44:40 to be a little bit more entrepreneurial.
0:44:43 I’m not quite sure what I was expecting to get
0:44:45 out of the big kind of corporate experience.
0:44:48 – And just as we wrap up here,
0:44:50 given what you know about, you know,
0:44:53 you write about politics, you write about technology,
0:44:55 your advice to someone just coming out of school
0:44:57 or a younger person, where do you think,
0:44:59 when you look at different industries,
0:45:01 do you think that someone who’s risk aggressive
0:45:04 in this industry could do very well
0:45:06 or sort of advice to your 25 year old self,
0:45:09 what would those industries or those jobs be?
0:45:11 – I think being differentiated,
0:45:14 maybe that’s a slightly too generic piece of advice,
0:45:17 but, you know, finding things that you’re passionate about
0:45:20 and things that you do like uniquely well, right?
0:45:22 You know, if you can be the best person ever writing
0:45:25 about, you know, women’s curling or something like that,
0:45:27 then it probably won’t be a career for you,
0:45:29 but you at least positively differentiate yourself.
0:45:31 One of the smartest things I did for the book, by the way,
0:45:34 is just kind of talking to smart people a lot.
0:45:36 So, you know, having good conversations,
0:45:37 but I think we’re in a world now
0:45:40 where particularly with the rise of AI,
0:45:43 and I’m kind of a, you know, I’m not like a AI doomer.
0:45:45 I’m also not an AI is going to conquer everything person.
0:45:48 I’m kind of uncertain about it,
0:45:50 but I think that will increase the premium
0:45:52 on not being average,
0:45:55 ’cause the AI will give you like a very good
0:45:57 above average version of average, if that makes sense, right?
0:46:00 It can kind of synthesize all the text on the internet
0:46:02 and put it together in a way that’s a little bit dry
0:46:05 and boring, but, you know, plausibly pretty good.
0:46:08 And so, do you kind of provide like a unique vector,
0:46:11 I guess, in the world that can’t be replicated anywhere else?
0:46:13 I think that’s a valuable skill.
0:46:14 – Yeah, I like what you said there.
0:46:18 I’ve always found that the specific crowds of the general
0:46:20 and commit to owning something,
0:46:22 like you said, women’s curling, commit to being,
0:46:23 you might think that’s too niche,
0:46:25 but if you’re the best in the world at covering it,
0:46:27 then eventually you’ll start covering ice skating
0:46:29 or something or people will want to have your,
0:46:32 know your take on different things.
0:46:34 Nate Silver is the founder of 538
0:46:36 and the author of the New York Times bestselling book,
0:46:38 The Signal and the Noise.
0:46:41 He also writes the sub-stack, Silver Bulletin.
0:46:42 His latest book, On the Edge,
0:46:45 The Art of Risking Everything, is out now.
0:46:49 He joins us from his home in Chelsea, adjacent.
0:46:51 Nate, I really enjoyed this conversation
0:46:53 and congrats on your success.
0:46:54 – Thanks so much, Scott.
0:46:55 It was great.
0:46:55 Talk to you soon.
0:46:58 (upbeat music)
0:47:04 – This episode was produced by Caroline Shagren.
0:47:06 Jennifer Sanchez is our associate producer
0:47:08 and Drew Burroughs is our technical director.
0:47:09 Thank you for listening to The Property Pod
0:47:11 from the Vox Media Podcast Network.
0:47:13 We will catch you on Saturday
0:47:15 for No Mercy, No Malice as read by George Hahn.
0:47:18 And please follow our Property Markets Pod
0:47:20 wherever you get your pods for new episodes
0:47:22 every Monday and Thursday.
0:47:25 – Thanks to Huntress for their support.
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0:48:06 (upbeat music)
Nate Silver, the founder of FiveThirtyEight and Substack writer of “Silver Bulletin,” joins Scott to discuss his latest book, “ON THE EDGE: The Art of Risking Everything.” We hear about the role of risk in shaping modern life, his background in election forecasting, and his thoughts on Kamala Harris’s VP pick. Follow Nate, @NateSilver538.
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