AI transcript
0:00:05 Support for this episode comes from The Current. The Current podcast is back with an exciting
0:00:09 new season featuring marketing executives from the world’s most influential brands.
0:00:13 Tune in to hear what’s driving conversation in the fast-moving world of digital advertising.
0:00:17 The unique insights from brands is diverse as Hilton, Instacart, Moderna, Major League
0:00:22 Soccer, and more. And in this presidential election season, The Current explores when
0:00:26 a national political advertiser like the National Republican Senatorial Committee and
0:00:33 a major CPG brand like Hershey can learn from each other. Listen in and subscribe to The
0:00:40 Current at TheCurrent.com or wherever you get your podcasts.
0:00:43 Support for Prophety comes from Fiverr. Hiring top talent takes months, costing you time
0:00:49 and opportunities. Well, what if you could build your dream team today? With Fiverr Pro,
0:00:54 it’s possible it’s your all-in-one solution for premium freelance talent, offering hundreds
0:00:59 of categories to outsource complex projects. Immediately, their dedicated hiring experts
0:01:03 will help you find your perfect match. Plus, get access to project management tools, flexible
0:01:08 hiring options, and more so you can meet your hiring needs with ease. And the best part
0:01:13 is there are no hidden membership or subscription fees to get started. Visit pro.fiverr.com
0:01:19 to sign up and use code PROPHETY for 15% off any service.
0:01:23 Episode 315, 315 is the area code covering the North Central area of New York State. In
0:01:29 1915, the iconic Contour Coca-Cola bottle was patented. True story, I watched a documentary
0:01:33 on cocaine the other night and I’ve decided that from this point forward, I’ll do a little
0:01:38 blow before I watch anything. That’s right, my new viewing partner, White Girl Interrupted.
0:01:51 Go, go, go!
0:01:56 Welcome to the 315th episode of the PROPHETY pod. In today’s episode, we speak with Simon
0:02:01 Sinek, an international speaker and bestselling author of the books Start With Why, The Infinite
0:02:07 Game, and Find Your Why. I become friends with Simon. He’s one of my, like, speaking
0:02:12 thought leaders slash, I don’t know, friends, if you will. I met Simon or spent some time
0:02:17 with him at Summit at Sea, which I went on, I guess it was more than a year ago now, and
0:02:20 I had one of those moments with him that I will remember for the rest of my life. He
0:02:26 was in London and we were eating at Grangers, which is lovely, which is lovely. And when
0:02:30 I’m out in London, it’s usually twice a day, sometimes as much as five, sometimes as little
0:02:35 as zero. Someone will come up to me and say something nice. And someone locked eyes on
0:02:39 me, came over and I’m like, “Here it comes.” And they came up and said, “Your work is
0:02:43 just so meaningful. Thank you so much.” And I said, “Oh, that’s really nice of you.”
0:02:47 And he shook Simon’s hand and kind of laughed, but he would meant it for Simon, not for me.
0:02:52 And it was one of those moments where I realized what a fucking narcissist I am. Anyway, Simon,
0:02:57 and it happened again during the same lunch before Simon. He has a huge following and obviously
0:03:03 his content really resonates with people. All right, what’s happening? I’m back from the long
0:03:11 holiday. I take most of August off. I got a little distracted and that is my podcast partner on the
0:03:15 other podcast. I have another podcast if you didn’t know called Pivot. And it’s with this
0:03:20 little lady named Kara Swisher and we were invited to the Democratic National Convention.
0:03:26 So, got my ass to Chicago, interrupted my holiday only to find out my security clearance had not
0:03:30 been cleared. I mean, they let in, what’s that guy’s name? Charlie Kirk. They let in like every
0:03:35 Joey Bagadona influencer in the world. It’s like, if you had, I don’t know, over 800 followers on
0:03:40 Instagram, they let you in. But I found out when I landed there that my badge, my security clearance,
0:03:46 had not been approved. So, I immediately took to whatever it was, some social to bitch about it.
0:03:52 And the conjecture was why are you not being allowed into the United Arena? I started going
0:03:57 over my history. I have never been arrested, released a dog. I was held up at, I was imprisoned
0:04:01 at the Nobu Chicago waiting to get into the DNC. Generally, I found the DNC, I thought it was very
0:04:07 well orchestrated. Too long. Too long. It should be three days not four days. Generally, like a great
0:04:13 vibe. I went to the one in 1996. I’ve always been a bit of a political junkie. And I went knowing
0:04:18 nobody and I met this guy and we ended up sharing a room so we could, I was so broke when he was
0:04:23 broke too when we were both there, total tourists. And I think we lied about our names to get into
0:04:27 a bunch of parties. I got to see Al Gore dance at one of the parties. That was kind of the highlight.
0:04:33 Anyways, but I was at the Democratic Convention. What was it? I guess that was 28 years ago when
0:04:38 Clinton was renominated for his second term. I spent time in New York. By the way, New York’s
0:04:42 on fire. It’s just on fire. I don’t care what anyone says. I think New York right now is in a golden age.
0:04:47 That’s about it. I’m mostly just talking about, oh, I went to Nat Tuckett. That was wonderful.
0:04:51 Anyone who’s been there, it’s basically a sandbar in the middle of the Atlantic. It’s
0:04:56 absolutely gorgeous. The thing I love about it is my kids can roam free and get into trouble.
0:05:01 Although it’s such a bummer they keep finding all these great whites everywhere around there. So
0:05:07 I’m just a total mess when my kids go into the water. And then I ended with an idea to speaking
0:05:14 in Brazil. Oh my God, beef, beautiful people. And what I think is arguably the best hotel in the
0:05:21 world right now, the Rosewood, Sao Paulo, what is not to like about Brazil? Seriously. I mean,
0:05:25 it’s just such an amazing, I think it’s probably my favorite place to go, right? It’s actually
0:05:29 my favorite place to go. Yeah, that’s outside of the US. I absolutely love it there. And I went to
0:05:34 the XP conference, which had 50,000 people. It made me want to buy stock in Brazil or buy,
0:05:40 I don’t know, the ETF on the Bolsa or whatever. I think it’s such an impressive culture and people
0:05:46 work hard and love to play hard. The people and the dress there, I was especially impressed with
0:05:52 the dress. Now, granted, I saw a pretty limited slice between the Rosewood and the Soho since
0:05:56 Sao Paulo, but it really is an impressive culture and had a wonderful time there. Just so fucking
0:06:00 far. Is there anything you can do about that, Brazil? Just a little too far. And speaking of
0:06:06 which, on the 11-hour flight yesterday, which leaves at 4 p.m., which makes no fucking sense,
0:06:11 I totally loaded up on movies. I watched “The League” or “The Syndicate of Un-Gentlemanly Warfare,”
0:06:15 which is a Guy Ritchie film. I enjoy his films because they’re so beautiful. And he has beautiful
0:06:22 men and beautiful clothes. And then I watched, oh my God, “Saltburn.” Jesus Christ. I had to
0:06:28 stop it because it was just like too much for me. It was like a little too much for the dog to
0:06:33 handle. I just kind of put my head in between the pillows and was like, “Calm down, take me to
0:06:39 a park with a bunch of tennis balls.” Anyways, an outstanding, what do I call it, outstanding?
0:06:44 Great. Hovering between great and outstanding. But Jesus Christ, that shits a lot. And a real twist
0:06:50 at the end, kind of like a crime game level twist that I did not see coming. I did not see coming.
0:06:54 I can usually guess everything that’s happening in the movie. I’m the kind of jerk that in the
0:06:58 movie leans over to my partner and says, “Oh, you know, the butler did it or whatever.” But yeah,
0:07:03 I did not see that one coming. And then I watched “Napoleon.” “Napoleon” because I like war films.
0:07:08 I thought it was pretty interesting. I did not realize that Napoleon was so obsessed with Josephine.
0:07:12 I thought it was interesting. I would not want to live in France in late 19th century. It seemed
0:07:18 like a pretty violent place where everybody would have their time in the sun and then they cut their
0:07:25 heads off. But I love warfare. I’m interested in war history. Napoleon’s Bonaparte or Napoleon’s
0:07:30 Waterloo, if you will, or him venturing into Russia, started with 400,000 troops, returned
0:07:37 with 40,000, was exiled once, then came back. And his troops really embraced him and then exiled
0:07:41 twice. I just thought it was, I thought it was fascinating. Was it a great film? No. Ridley Scott
0:07:46 is just fun to watch because he gets so much, such big budgets. And the cinematography was so
0:07:50 incredible. And Joaquin Phoenix is obviously a fantastic character. Anyway, those are my
0:07:56 three films. So in order, salt burn, I would definitely see but brace yourself. Napoleon,
0:08:03 if you like war history and the League of Ungently Warfare, I’d say pass or wait till it’s
0:08:07 on Netflix or it’s already on Netflix. I just thought it was just okay. All right, enough about
0:08:13 our travels. We have some news to share here at PropG. Starting next week, we are launching another
0:08:19 podcast called “Raging Moderates.” It’s a PropG podcast co-hosted with our favorite political
0:08:25 gangster and rising star, Jessica Tarlov. If you don’t know Jessica, she is a co-host on the five,
0:08:29 Fox’s weeknight news program and plays a key role in special coverage for the networks.
0:08:35 Everything’s so polarizing. I think it myself is kind of, I don’t know, squarely in the middle.
0:08:38 And I love the term “Raging Moderates.” I said leading up to the election and if it works, maybe
0:08:43 after. Let’s try and explore all views of this using data. Essentially for business reasons,
0:08:48 we should not be doing politics because you just turn off people. Advertisers don’t like it,
0:08:52 but I can help it. I’m interested in it. I think it touches on everything, society, technology,
0:08:56 the economy. And I think it’s, if you want to understand America, if you want to understand
0:09:02 our economy, you need to have some basic rooting in politics. Plus, I just think it’ll be fun.
0:09:08 Anyways, so with that, we hope you enjoy “Raging Moderates.” Love that title. Love that. I came
0:09:13 up with that. I came up with that. A weekly podcast from the PropG universe. New episodes will be
0:09:20 right here on the feed every Tuesday to resist is futile. We’re fucking AOL in the 90s. You stick
0:09:30 your hand into a cereal box and you’re going to get the dog. We’ll be right back for our conversation
0:09:39 with Simon Sinek. Support for PropG comes from Netsuite. There’s no sure far way to predict what’s
0:09:43 coming next to your business. You can look at lots of graphs. You can listen to all of my podcasts.
0:09:48 You can even consult a high-price psychic, though I don’t recommend it. So how can you prepare for
0:09:52 anything when there are so many unknowns right around the corner? Smart businesses have gotten
0:09:56 themselves future ready with Netsuite by Oracle. Netsuite is a go-to business management suite
0:10:01 for almost 40,000 companies offering everything you need to stay on track, no matter what tomorrow
0:10:05 brings. Netsuite combines accounting, financial management, inventory, HR, and more into one
0:10:10 simple platform offering a single source of truth. Get real-time insights and data you can use to
0:10:15 make the right decisions faster than ever before. Don’t get caught looking backwards. Get ahead of
0:10:21 the curve and stay focused on what’s coming next with Netsuite by Oracle. Speaking of opportunity,
0:10:27 you can download the CFO’s guide to AI and Machine Learning at Netsuite.com/PROF. This guide is free
0:10:39 to you at Netsuite.com/PROF. That’s Netsuite.com/PROF. Support for this show comes from Betterment.
0:10:43 Do you want your money to be motivated? Do you want your money to rise and grind?
0:10:48 Do you think your money should get up and work? Don’t worry, Betterment is here to help.
0:10:52 Betterment is the automated investing and savings app that makes your money hustle.
0:10:56 Their automated technology is built to help maximize returns, meaning when you invest with
0:11:01 Betterment, your money can auto-adjust as you get closer to your goal. Rebalance if your portfolio
0:11:06 gets too far out of line and your dividends are automatically reinvested. That can increase the
0:11:11 potential for compound returns. In other words, your money is working like a dog while you can be
0:11:17 sleeping like one and snoring like one too. You’ll never picture your money this same way again.
0:11:21 Betterment, the automated investing and savings app that makes your money hustle.
0:11:26 Visit Betterment.com to get started. Investing involves risk. Performance is not guaranteed.
0:11:35 Support for Prop G comes from Mint Mobile. If you’re serious about keeping your budget in
0:11:40 check, your monthly expenses are one of the first places to look. And one thing a lot of us over
0:11:45 pay for is our phones, especially between all the hidden fees and other nonsense phone companies
0:11:51 throw at you, which is why Mint Mobile is doing things differently. When you switch to Mint Mobile,
0:11:55 you can get three months of premium wireless service for just 15 bucks a month. All of Mint
0:12:00 Mobile’s plans come with high-speed 5G data and unlimited talk and text. Plus, you don’t need
0:12:04 to worry about getting a new device or phone number. Just bring those with you over to your new
0:12:09 Mint Mobile plan. To get this new customer offer and your new three-month premium wireless plan
0:12:15 for just 15 bucks a month, you can go to Mint Mobile.com/PropG. That’s Mint Mobile.com/PropG.
0:12:22 You can cut your wireless bill at 15 bucks a month at Mint Mobile.com/PropG. $45 up from payment
0:12:27 required equivalent to $15 a month. New customers on first three month plan only. Speed slower above
0:12:33 40 gigabytes on unlimited plan. Additional taxes fees and restrictions apply. See Mint Mobile for details.
0:12:51 Welcome back. Here’s our conversation with Simon Sinek, an international speaker and best-selling
0:12:55 author of the books Start With Why, The Infinite Game, and Find Your Why.
0:13:00 Simon, where does this podcast find you? I am back home in Los Angeles.
0:13:06 So, let’s bust right into it. You describe yourself as an unshakable optimist, and I’m
0:13:11 a naturally pessimistic person. So, I’m curious, how do you maintain your optimism,
0:13:14 especially in challenging times, and what advice would you give to someone
0:13:19 who tends to be, like myself, kind of see the glasses half empty, if you will?
0:13:26 So, optimism doesn’t mean I’m naive nor blind, and it’s not blind positivity. It’s not looking at
0:13:32 a broken world and be like, “Everything’s fine. That’s not how I am. I’m quite cynical a lot of
0:13:37 the time.” But I generally believe that the world tends toward good, and I believe that even if we’re
0:13:42 in darkness, that if we come together and work together, we will get through this, and we will
0:13:46 come out better than we went in. So, it’s the undying belief that there’s a light at the end of the
0:13:52 tunnel. And you’re sort of known as the leadership guy or the why guy, I guess. Break down for you,
0:13:56 what is the definition or the key to effective leadership?
0:14:01 I think leadership is an incredibly misunderstood subject. I shouldn’t really
0:14:09 have to write books about it. I visited rural Kenya recently and met some people who we would
0:14:16 describe as poor. And one of the mamas, she organized a women’s empowerment group where
0:14:19 they sort of help each other out, and she was telling us how she does it and how she
0:14:24 overcomes some of the challenges. And literally, she was telling me stuff that I’ve written about.
0:14:29 In other words, she’s a brilliant natural leader, and she doesn’t do it out of some sort of
0:14:33 philosophical construct. She does it because it’s practical and it works. And if people are
0:14:38 seen and heard and taken care of and feel like they can trust each other, they’ll take risks,
0:14:43 they’ll open up, they help each other. For me, leadership is the awesome responsibility to see
0:14:48 those around us rise. And what we can do when we’re in a position of leadership, whether it’s
0:14:52 formal or informal, rank does not mean that you’re a leader. It just means you have authority.
0:14:57 But if you’re in a position of formal or informal leadership, that you look to the left and look
0:15:01 to the right and say, “What can I do to support?” You’ve often talked about the distinction between
0:15:05 natural born leaders and leadership developed as a skill, and you’ve said that you think it can be
0:15:10 developed. If someone is young, I think I want to have developed those leadership skills. What are
0:15:17 some exercises for doing that? I mean, first of all, I don’t believe leaders are born. I think that
0:15:21 some people have an education when they’re younger. They have a coach, they have a parent,
0:15:26 they have a guardian, somebody in their life, a teacher who does something right. They model
0:15:30 some themselves after that person, and they seem to learn it younger, or they have some trials and
0:15:35 tribulations, and they learn to overcome and rely on other people, whatever it is. But even
0:15:40 some of the great leaders that we admire, if you look back, whether it’s Steve Jobs or Mahatma Gandhi,
0:15:45 you see that they were learning and they didn’t get it right a lot of the time, especially when
0:15:50 they were younger. They learned those skills. For me, fundamentally, the single best thing
0:15:58 a young person can do is really learn to be a friend, learn to put away a device, and learn how
0:16:04 to engage with another human being, learn how to be there for someone, learn how to accept help
0:16:09 when it’s offered, learn how to ask for help, and all of these pretty fundamental things about
0:16:15 adolescence. When we’re very, very young, the only thing we want or need is the approval of our
0:16:19 parents. Look, daddy, look what I made. Watch me jump over the step, and then we give them positive
0:16:23 reinforcement, and all that serotonin flows, and it feels really good. And literally, nobody else
0:16:29 matters except mom and dad’s approval. That’s it. When we reach adolescence and all the hormones
0:16:36 start flowing, we make this change, this conversion where we now crave the approval of our friends
0:16:43 and our peers. Very stressful for us, very frustrating for our parents who are watching
0:16:48 us change. Really essential for a human being to learn to acculturate for the wider group outside
0:16:53 of their immediate family. And so it should be natural that we learn to ask for help from friends
0:16:58 and learn to give help to our friends. So to be a great leader, learn friendship.
0:17:03 You’ve equated it to being a parent that is leadership. What did you mean by that?
0:17:09 Well, you don’t get to choose your kids, but you love your kids and you want to raise them to be
0:17:14 the best that they can be. You don’t often get to choose your team if you’re promoted into position
0:17:22 of leadership, but you still get to celebrate them and try your best to help raise them to be the
0:17:27 best that they can be. And there are a lot of similarities and a lot of things that you can
0:17:32 learn about leadership you can learn from parenting books. For example, affirming a child’s feelings.
0:17:36 You know, dad, I’m sad. No, you’re not. It’s fine. It’s good. What do you have to be sad about? Your
0:17:43 life is great. That’s bad parenting. You want to affirm the kids feelings. Same at work, you know,
0:17:47 to talk people out of their feelings makes them feel unseen and unheard. Good leadership overlaps
0:17:52 a lot with good parenting because it’s interaction with other human beings working to see them build
0:17:57 confidence and be the best that they can be. And sometimes we have to be patient to let them try
0:18:02 again. What do you think the biggest mistake that leaders or managers make? I mean, you mean you
0:18:07 talk about management versus leaders. Nobody wakes up in the morning to be managed. Nobody says,
0:18:12 “I’d like to be managed, please.” But we would all like to be led. And I think what you’re doing is
0:18:16 highlighting the problem. A lot of leaders act like managers. You can manage a process, you can
0:18:21 manage a company, but you can’t manage people. You can lead people. And I think when we start
0:18:29 managing people as if they are a process, things start to break down. And I think another very,
0:18:35 very, very common mistake that newly minted leaders make is they believe that their intelligence
0:18:41 or capacity or their ability to give answers to every question is what gives them their credibility
0:18:46 to lead. And so you’ll see a lot of leaders lying, hiding and faking. They won’t admit if they don’t
0:18:50 know something. They won’t say, “I don’t know.” They won’t ask for help because they fear that
0:18:55 undermines their credibility, which is completely false. We get a lot of questions about mentorship.
0:18:59 So I’ll turn the question to you. What advice would you give someone who’s looking for a mentor?
0:19:05 How do they go about finding a mentor? So when my career was just sort of getting going,
0:19:12 I was introduced to this guy named Ron Bruder. Ron, a very, very accomplished entrepreneur,
0:19:18 really successful. And he was charming and lovely and super helpful and wonderful in our meeting.
0:19:24 And about a week or two later, I called Ron, who’s a very busy man, and he took my call.
0:19:29 And a few weeks later, I called him again. I needed some advice. And he took my call again.
0:19:34 And at some point, we went out for lunch. And eventually, this sort of mentor-mentee relationship
0:19:40 evolved. And I thought of him as my mentor. And I remember we became quite close. And I remember
0:19:45 I was leaving his house one day, and I used the M word for the first time. And I put my arm around
0:19:49 him as I was saying goodbye. And I said, “You know, Ron, I’m glad you’re my mentor.” And he said
0:19:55 something back I didn’t expect. He said, “And I’m glad you’re mine.” And this is what I think
0:20:01 great mentor relationships are, which is it’s both of us are mentors and both of us are mentees.
0:20:05 Somebody who’s had more experience is still learning about the world from somebody who’s
0:20:09 asking for help. However, I think they do evolve like friendships. I don’t think you can go up
0:20:13 to some random person and say, “Will you be my mentor?” Just as you can’t go up to some random
0:20:18 person on the street and say, “Will you be my friend?” It’s a relationship. And for me, the
0:20:23 definition of a mentor is someone who always has time for you. And it can’t be one-sided. You
0:20:26 can’t simply just because someone’s accomplished and you’re not, you can’t just go up to them
0:20:31 and think they’re an asshole because they don’t want to mentor you, just like you can’t think
0:20:34 someone’s an asshole because they don’t want to be your friend. It’s a relationship. And there’s
0:20:39 a lot of sacrifice that comes with it. What I love about mentorship is a mentor is not a champion.
0:20:46 I think people mistake them. Like in a company, you can have champions who can go to bat for you
0:20:50 and put in a good word for you. You can get that promotion. And the best mentors are not in your
0:20:55 chain of command. They’re either outside of your department or even better outside of the company.
0:20:59 And the only thing they care about is you and your growth. And there’s nothing they can do to
0:21:05 interact, intervene. It’s a very pure relationship where you both learn, you both give, and you
0:21:10 show up for each other. Yeah, it’s interesting. I really have had a lot of mentors, but I’ve
0:21:15 never ever asked anyone to be my mentor. I’ve asked for help. Or I said, “Can we grab coffee?”
0:21:19 And like you said, the relationship, the relationship evolves.
0:21:25 Talk about the tension between self-actualization and putting a group’s needs first. You write
0:21:29 a lot about this. Does that tie into what you’ve spoken about regarding leadership?
0:21:39 I mean, you’re hitting a nerve for me. Mas loves hierarchy of needs. That’s self-actualizations
0:21:47 at the top. Mas left me with a bit of a mistake, which is if you look at the hierarchy of needs,
0:21:51 at the bottom, the most basic need he articulates as food and shelter.
0:22:02 And the third rung up is relationships. Now, I’ve never heard of anybody dying by suicide
0:22:06 because they were hungry. I’ve heard of people dying by suicide because they were lonely.
0:22:11 In other words, it seems to be inconsistent with reality that food and shelter would come
0:22:19 number one, but not entirely. Basically, being human is a paradox. Every moment of every single day,
0:22:23 you and I are both individuals, we’re ourselves, but we’re also members of groups. We’re members
0:22:30 of teams, churches, families, whatever it is. And we are confronted with little and big decisions
0:22:34 on a regular basis. Do I put myself first at the sacrifice of one of the groups? Or do I put
0:22:39 the group first at the sacrifice of myself? And people debate this. You always put yourself first
0:22:42 because you can’t help the group unless you’re healthy. You always put the group first because
0:22:45 they won’t be there for you unless you take care of them. And the answer is you’re both right
0:22:50 and you’re both wrong. It’s a paradox, and it’s difficult, and it’s messy. And so Mas love only
0:22:57 considered us as individuals. As individuals, if we lived like great white sharks, 100% correct,
0:23:03 number one would be food and shelter. But as members of groups, it’s different,
0:23:08 and there’s new ones. And so it’s this constant battle between the two. And the thought of living
0:23:13 an entire life to get to the top of a pyramid called self-actualization, where we look down at all
0:23:21 the unactualized people, seems antisocial versus shared actualization, which is raising the team,
0:23:28 raising the company, raising the society, raising the nation. That to me seems more pro-social.
0:23:35 And so good leaders, I think, are doing that. They recognize the paradox. They struggle with
0:23:42 the paradox. But at the same time, they work tirelessly to bring the group that we all rise
0:23:45 together to share an actualization, that we all are working to something bigger than ourselves.
0:23:52 I saw you on the Diary of CEO podcast, and you spoke about people struggling to make friends.
0:23:57 Can you say more about why you think modern society makes it so difficult for people to
0:24:04 develop deep, meaningful relationships? I mean, there’s a host of reasons. No one reason
0:24:09 is the reason. I mean, it’s easy to blame cell phones and social media, and they definitely
0:24:13 play a role, and I think they definitely exaggerate it. I don’t think they’re the sole cause.
0:24:17 Parenting is a big part of it as well. I mean, you and I have gone to restaurants,
0:24:23 and you look over to the table next door, and the parents have slapped an iPhone or an iPad in front
0:24:28 of their little children because they don’t want noisy kids at dinner. They could have brought
0:24:34 colored pencils, and so parenting is a large part of it as well. You see this in education
0:24:38 reform. You talk to teachers or superintendents. They’re all in favor of education reform. Even
0:24:43 the students are up for it. It’s the parents who are often the most resistant because I want you
0:24:49 to reform education, but just don’t experiment on my kids. Cell phones are the same. Schools
0:24:53 want to get rid of them. It’s the parents who are put pressure to say absolutely not, you may not.
0:25:04 I think it’s dramatically exaggerated by the devices, but I also think it’s the
0:25:11 whole thing. Our society, and this goes back a few decades, we’ve over-indexed on rugged
0:25:18 individualism, where it’s all about you, your strength, and we don’t value as much team
0:25:25 celebration, team effort. We did this, not I did this. I don’t know if you ever saw Elizabeth
0:25:32 Gilbert’s TED Talk, but it was magical, and it was hugely helpful to me. She talks about the concept
0:25:40 of genius, and then the pre-renaissance. A genius was a daemon, a spirit that lived in the walls,
0:25:47 and if you did something great, people would say of you, you had your genius. Your genius was with
0:25:51 you, so you couldn’t take full credit for your accomplishments. If you failed, people would say,
0:25:56 “Oh, I’m sorry, I guess your genius wasn’t with you.” You couldn’t take full credit, but you never
0:26:01 had to beat yourself up if it didn’t go so well either. At some point in the renaissance,
0:26:07 having your genius became being the genius. Now, if you accomplish something great, people said of
0:26:12 you, “You are a genius, and now you’re labeled and straddled with that stress for the rest of your
0:26:17 life, and the fear of not being the genius anymore becomes part of the identity, which I think is
0:26:23 part of the failure.” But I think what we’ve done is it’s all part of the package of this over-indexing
0:26:29 on this rugged individualism, especially in America, where we’ve heroized CEOs, and we’ve heroized these
0:26:34 individuals who none of them accomplished their stuff by themselves, but we don’t celebrate the
0:26:41 team, the group, as much. I think it’s acidal. I think it’s part of one of the unfortunate side
0:26:49 effects of Jack Welch and Milton Friedman economics of the ’80s and ’90s, which we’re trying to undo
0:26:55 over the course of these years. Yeah, I think it’s also not uniquely American phenomena, but American
0:27:00 phenomenon. That is, we like to think we live in a meritocracy, and anyone can be anything,
0:27:06 and that’s a very nice aspirational bumper sticker. But if you believe that, the dark side of that is,
0:27:11 well, if it’s truly a meritocracy, and anyone could do anything, then if you don’t end up wealthy,
0:27:16 and in a position of influence, you fucked up. I mean, I know you know this, and I know this.
0:27:20 A lot of our success is not our fault. At the same time, when we screw up, a lot of that is not
0:27:25 your fault. But it feels very American to put pressure on people that if you don’t end up in a
0:27:35 certain position, it’s on you, brother. I completely agree. I mean, I’ve always tried to live with the
0:27:50 formula, the notion that success is the zero sum of effort, talent, and luck. And you want to
0:27:55 get keep those things somewhat, they’re imperfect, and they sort of go like this, but at some point,
0:28:02 they lead to one. So for example, if you win the lottery, no effort, no talent, pure luck, not
0:28:08 stable. If you work really, really hard, but you’ve got no talent, you had no luck, you’re
0:28:12 not going to succeed either. And it’s just really frustrating. And if you have talent that you don’t
0:28:17 capitalize on, again, and so I think you and I both recognize that we’ve tried to steer in our
0:28:23 careers in a direction where we’re more likely to do better than not. Like if I’m really good at math,
0:28:29 I should probably point myself in a direction where math is needed. And if I’m, you know,
0:28:35 maybe not be a football player if I have no athletic ability, no matter what my dreams are,
0:28:39 you know, so we try and point ourselves, we have an unfair advantage because of our natural gifts,
0:28:45 work hard and hope that things work out, you know, you cross your fingers a little bit and
0:28:52 it happens. I’m not the most disciplined person in the world. I have seriously bad ADHD, which means
0:28:57 I struggle to read books. People think I’m really well read. I’m not. I’ve written more books than
0:29:04 I’ve read. And yet I found ways to navigate these things rather than make them bowls and chains.
0:29:10 My sense is you also have a pretty authentic voice, but it’s not easy to manage. I’ve mostly
0:29:16 been able to screen out feedback from social media, mostly, but some of it gets so angry and so
0:29:21 vile. Sometimes it’s difficult to screen out. What do you do to manage and try and maintain
0:29:27 that authenticity without, you know, getting upset all the time and all the shit we get online?
0:29:32 Yeah, I work very hard not to be political. Like I don’t give to candidates. I don’t endorse
0:29:38 candidates. I won’t go to fundraisers. I believe in bipartisanship. So I’ve spoken at Republican
0:29:42 congressional off-sites. I’ve spoken to Democratic congressional off-sites and I give them the same
0:29:48 message because I want unity. So if I preached bipartisanship and picked aside publicly,
0:29:55 then I’d be full of it. So one part is, is I believe that the work that we do is bigger than
0:30:01 politics. And so I try and play at that level. And who I vote for is my business, registered
0:30:07 independent. And I also, in terms of like, because the overwhelming pressure, especially when anything
0:30:13 happens socially, the overwhelming pressure from friends and fans alike to weigh in, it is sometimes
0:30:21 well, high stress, high pressure. My rule has always been that I will, that I will only say
0:30:25 something publicly if I believe that I can be additive. And if it takes me a week to come up
0:30:31 with something that’s additive, then I’m going to wait a week. And it’s very hard to resist the
0:30:40 pressure, but I don’t want to simply add to noise simply because a certain base wants me to join
0:30:46 their side. My rule is it has to be additive. It has to be additive. And by the way, sometimes
0:30:52 I have nothing to say that’s additive. And so I will sometimes be conspicuously quiet. I only
0:30:59 want to contribute, not just, not just virtue signal. It’s funny. I actually thought about you
0:31:04 because in an unusual context, when all these videos emerge, JD Van saying that the world is
0:31:12 being run by these lonely, hateful people without children who have cats. I’m one of them. I thought
0:31:18 of you. I thought, Simon has never been married. It doesn’t have kids. I know you really value
0:31:22 your relationship with your nieces and nephews. And my sense of you is you have a lot of friends
0:31:28 and a good support network. Do you get lonely? Do you feel like you’re judged sometimes for not
0:31:33 going the traditional route in terms of relationships and kids? 100%. So those are two
0:31:42 different questions. I’ll deal with the second one first. So I have a friend who was in a very,
0:31:51 very dysfunctional 16-year relationship. He had, it was just chaotic and dysfunctional. And she’s
0:31:55 been out of it for a few years, but she’ll freely admit that she probably should have been in it
0:31:59 for a year. And she always felt that she could fix him and save him. I don’t know what it was,
0:32:05 16 years of a committed monogamous relationship. I’ve never been married.
0:32:13 My longest relationship was three years. And the world judges me. When I go on dates, like,
0:32:18 women will say to me, “What’s wrong with you?” Some of my friendships are better and closer and
0:32:24 more loving than a lot of marriages or monogamous relationships. And certainly, the life that I
0:32:28 live and the friends that I have are better than that relationship. But why is it that society
0:32:33 says that she’s healthier and I’m unhealthy or she’s correct and there’s something wrong with me?
0:32:38 When people say, “Why haven’t you been married?” I might say, “Isn’t it obvious I haven’t met the
0:32:44 right person yet?” Like, “Isn’t that obvious?” For whatever reasons, I think we’re starting,
0:32:49 we’re in a time now where people are becoming more open to different types of relationships,
0:32:55 that people can be in union without a marriage, raise a family without the marriage. And society,
0:33:00 for the most part, says, “So long as you’re good parents and so long as you’re doing right by each
0:33:05 other and the kids, have at it.” You don’t necessarily need the religious or the legal
0:33:11 document to have the family. And society is more open to that than it used to be. And so,
0:33:19 I’m hoping that society starts to recognize that having fulfilling friendships, having fulfilling
0:33:23 relationships, and by the way, many people would say that the only difference between a close
0:33:27 friendship and a marriage is you can have sex with your spouse. But it turns out you can do
0:33:33 that with friends too. You can be very fulfilled. So, I think you’re right. I absolutely have been
0:33:40 judged my whole life. And the older I get, the judgment is even harsher. And yes, like any human
0:33:45 being, I get lonely. I get lonely. People in relationships get lonely. But yes, of course,
0:33:52 I get lonely. But this is why I love my niece and nephew so much, is because I don’t have my own
0:34:01 kids. They have a little bit of my DNA. And I get to give love to these aspiring magical little kids,
0:34:05 not a little anymore. And I get to impart everything that I’ve learned and who I am
0:34:10 in a way that a parent can’t. I can get away with stuff as an uncle that a parent can’t,
0:34:16 which I know contributes to their lives. And I love that. And they’re both at camp right now,
0:34:20 and I miss them desperately. You know this. You know this. When you had kids that profoundly
0:34:28 changed everything about the way you viewed your life. And I see how you bring your son
0:34:31 with you. So, I’ve just been watching your Instagram and how you bring your son on your
0:34:35 business trip. And you bring your son to games. And you know, you’re trying to give him the
0:34:42 craziest experiences that he can have. And what an amazing thing that, like it’s an amazing thing
0:34:48 to live an amazing life. It’s even more amazing to share it. And define amazing however you want.
0:34:52 But to go on an adventure with a person, I find vastly more fulfilling than going on an adventure
0:35:02 alone. We’ll be right back. Support for PropG comes from LinkedIn. As a B2B marketer,
0:35:06 you know how noisy the ad space can be. If your message isn’t targeted to the right audience,
0:35:11 it just disappears into the noise. With LinkedIn ads, you can work with precision and reach the
0:35:16 professionals who are more likely to find your ad relevant. With LinkedIn’s targeting capabilities,
0:35:21 you can reach them by job title, industry, company and more. You’ll have direct access to and build
0:35:27 relationships with decision makers. That’s a billion members, 130 million decision makers
0:35:31 and 10 million C level executives. You’ll also be able to drive results with targeting and
0:35:37 measurement tools built specifically for B2B. In technology, LinkedIn generated two to five times
0:35:42 higher return on ad spend than any other social media platforms. And 79% of B2B content marketers
0:35:47 said LinkedIn produced the best results for paid media. Start converting your B2B audience
0:35:51 into high quality leads today. We’ll even give you $100 credit on your next campaign.
0:35:58 But a LinkedIn.com/Scott to claim your credit. That’s LinkedIn.com/Scott. Terms and conditions
0:36:07 apply. LinkedIn, the place to be, to be. Support for this podcast comes from Huntress. Keeping
0:36:12 your data safe is important. However, if you’re a small business owner, then protecting the information
0:36:18 of yourself, your company and your workers is vital. And comes Huntress. Huntress is where
0:36:23 fully managed cybersecurity meets human expertise. They offer a revolutionary approach to managed
0:36:28 security that isn’t all about tech. It’s about real people providing real defense. When threats
0:36:33 arise or issues occur, their team of seasoned cyber experts is ready 24 hours a day, 365 days a
0:36:39 year for support. Visit huntress.com/propg to start a free trial or learn more.
0:36:46 A Spotify, no matter the type of small business you own, upgrading your lighting or refrigeration
0:36:51 can save you energy and money on your electricity bills. And we’ve got you covered with incentives
0:36:55 to reduce the upfront costs. Visit bcihider.com/incentives to learn more.
0:37:03 I’ve gotten to know you a little bit. And what’s interesting is we’re, we’re actually quite similar
0:37:08 in terms of our profession. And I think I’ve achieved you more so, but achieved certain levels
0:37:12 of success and thought leadership, whatever the hell you want to call it. But what really struck
0:37:17 me was one of the major differences on the, on the front end, I think people say, oh, they’re
0:37:22 similar doing the same thing the same way. You’re really about kind of ideas and impacting people.
0:37:27 And whenever I start to talk about business or we share business ideas or talk about money,
0:37:32 your eyes glaze over. And for me, and I’m not, I’m, I’m not proud of this.
0:37:37 Money is like right up there for me or business or like building successful business that I can
0:37:43 monetize. And as I’ve gotten older, I’ve got much better at sharing it. But you’re, you really are
0:37:48 about the ideas. I’m more about the ideas for me are really interesting and I love it. But it’s
0:37:54 a means to, I want to build a robust business. And, and I thought was just so we’re built much
0:37:59 differently that way. Any thoughts? I mean, you’re right. You, you like the money and the success
0:38:05 and the ideas are the means to that. And I’m the opposite, which is I like the ideas and the
0:38:12 business, if the ideas are good, then the business will follow as for me, the, the, the value that
0:38:17 other people put on, on the things that I put out in the world are proof that the, the ideas have
0:38:22 value. Jesus, I sound awful. I, we’ve got to cut this out. That’s like, your rap is so much better
0:38:28 than mine. And then that, that is such a better way. Did you know, no, I, and I’ll tell you why
0:38:37 I disagree with you is you’re honest. Like if, like if investment banks took their stupid purpose
0:38:41 statements down about how they want to help the world or share something or build economies,
0:38:47 which is complete nonsense. And if CEOs of a lot of companies simply said, look,
0:38:53 we’re just here to make cash. I want to get rich. I want the people around me to get rich.
0:38:58 These shareholders want to get rich. We’re going to help them get rich. And we’re going to try and
0:39:03 make a great product for you in order to get rich. I had actually be, that’s what they’re doing.
0:39:07 We all know that’s what they’re doing. They’re just lying to us and saying that other things are
0:39:14 more important. And so the honesty, quite frankly, means that I know what I’m getting and I know how
0:39:20 to invest. And I know how to, I know what level of trust or what barriers or what to believe.
0:39:25 And so, because right now it’s so hard to know what to believe because everybody’s bullshitting us.
0:39:32 And so I find your attitude so refreshing. And you and I are tortured by different things.
0:39:38 And we’re tortured by the, probably the thing that we put second. Like I’m, I’m tortured
0:39:43 that I’m not good at the structure stuff. And like, and you, you sort of say, you know,
0:39:46 you’re more successful than me in terms of this thought leadership, which I don’t even see.
0:39:54 I mean, you’re, you’re, your game is so good. And I, I’m like, I, even though when we first met,
0:40:02 we, I remember when we first met and I was like, okay, it’s kind of a little bit grumpy,
0:40:09 definitely pessimistic where I’m optimistic. I like him. I respect his work, friendship, maybe,
0:40:13 right? And the more I’ve gotten to know you, and we don’t know each other well, but we’ve
0:40:19 hung out a couple of times. I really, I really love spending time with you because I see us as
0:40:25 yin and yang. And I see us as, as actually trying to do the same thing. You have a bigger heart than
0:40:31 you give yourself credit. And you’re, you have a lot more warmth and kindness than you give yourself
0:40:36 credit. I’m probably better at the shit that I beat myself up about them, you know, than I
0:40:41 realize or that I give myself credit for. And you and I make each other uncomfortable because my
0:40:45 strengths are your weaknesses and your weakness, and your strengths are my weaknesses. And that’s
0:40:52 the discomfort, which is spending time with you just reminds me what I suck at. And I’m sort of
0:40:56 having a minor love affair with you and your work. Like when I see you pop up on my Instagram,
0:41:00 constantly, by the way, well done. To resist this futile. I’m AOL in the 90s.
0:41:06 Constantly. Whatever your algorithm, you nailed it. Like I, I actually had to mute you just for
0:41:14 a week just to have a breath. You know, your stuff is getting better. You’re clearer. And I just,
0:41:20 I sit quietly and go, fuck, that’s good. I love how we turn my interviews into me, but back to you.
0:41:25 Well, I’ll share something about me and I, I want, I want you to respond. You said something that was
0:41:29 really interesting. And that is you’re kind of a function of what’s tortured you. I grew up with
0:41:36 real economic anxiety. So it’s just a, it’s a ghost and a demon or, you know, a monkey on my
0:41:41 back. I just can’t shake. I’m always thinking about money. I’m very, very worried about being poor
0:41:47 again. And it’s hugely motivating, but also anxiety driven. And that is sort of my,
0:41:52 I don’t know if it’s my cross to bear, but it plays too big a role in my life.
0:41:57 What do you think it, it tortures you and where does it come from?
0:42:04 So what I know about the concept of why this, which is this thing, this deep seated inspiring
0:42:08 thing inside all of us, one of the things that I’ve learned about it is the thing you give to
0:42:11 the world, the thing you have, that gives you valuing in the world and to your friends and your
0:42:17 relationships is also the thing you need the most. And so it makes perfect sense to me in this balanced
0:42:22 equation of this thing you crave is this thing you fear, you know, that makes perfect sense to
0:42:28 me and that you grew up without means you’re afraid of having going back there. My torture is
0:42:37 I really, really bad ADHD in a time where it was never diagnosed. You know, I was just considered
0:42:43 a hyperactive. My parents, by modern standards, did a lot of the wrong things. I don’t fault them
0:42:50 for it. There was no, there was no, you know, they, they did the best they could with a hyperactive
0:42:55 kid who couldn’t focus and didn’t do schoolwork. I mean, what are you supposed to do? Do your
0:43:00 homework and I didn’t do it. And I’m like, I don’t, you know, and so, you know, I, I’m, I really
0:43:07 struggle to build structure and business is nothing more than structure. That’s what it is. And I
0:43:13 carry like when I talk to people who are brilliant operators and some of my, some CEO, entrepreneur
0:43:17 friends who just, I watch the structures that they’ve built. Now, are they operating, you know,
0:43:22 are they changing the world? Are they contributing to society? No. But my goodness, they built these
0:43:27 remarkable, and I get so insecure because for them it comes so easily. And for me, I really struggle
0:43:34 with it. And I’m to the point where I just stay quiet in those meetings when people like talk about
0:43:39 finance in front of me and they use all the financing jargon or an investment jargon and
0:43:43 they just assume I know it all because I’m at a point in my career where I guess others do.
0:43:49 I literally just have to go quiet out of sheer embarrassment. And so I carry a lot of discomfort
0:43:59 that I really don’t understand money. I don’t understand it. I’m not good at it. And any money
0:44:09 that I’ve made was an accident. And I see people who are contributing to society less work less
0:44:15 hard on the work that they do. And I see them make way more. And I’m not mad at that, but it
0:44:22 makes me feel like, come on, fucker, like up your game, you know. And I feel insecure in the worst
0:44:27 of times. And the best of times, I surround myself with people who are really good at it.
0:44:35 I ask advice, I’ve called you for things that are probably remedial, but to me, they’re advanced.
0:44:40 And just learn to get over the discomfort of asking for help
0:44:43 from people who I fear will judge me because they know so much more than I do.
0:44:48 Yeah, I think what you just described, though, having a lack of financial literacy,
0:44:58 I think you’re describing 97% of America. And I want to be clear. I’ve been wealthy three times.
0:45:02 And the reason why it’s been three times is because twice I lost it all because I was not
0:45:09 financially smart. I could have held on to my wealth. And instead, I was bought into this kind
0:45:16 of VC, fomented zeitgeist of go all in on something. And if you really, if you persevere and never
0:45:20 give up, I should have given up. I should have sold my stock or diversified. Instead, I was going
0:45:27 like 120% in on things. And then some things out of your control, some things in my control,
0:45:32 I just screwed up. But, you know, when the dot bomb implosion happened, I got broke again.
0:45:35 When the great financial recession came along, because I hadn’t been smarter and diversified,
0:45:40 I got broke again. And I think some of the, I hear some embarrassment or self-consciousness
0:45:45 in your voice, I think it’s especially prevalent among men, because they assume if you’re successful,
0:45:51 that you’re not really successful in America as a man, unless you’re financially extraordinarily
0:45:57 successful, and that you just accidentally wake up and get money, right? We’re supposed to be
0:46:01 you know, we’re supposed to wake up and accidentally have, you know, a five o’clock
0:46:06 shadow, a deep voice, a desire to procreate and be just really good at money. Otherwise,
0:46:10 we’re really not men. Do you think that in America, I wonder if one of the things that
0:46:17 creates loneliness among men is that we’re not, we’re so evaluated now, I think women are so
0:46:22 disproportionately evaluated on their aesthetics, but at the same time, men are so disproportionately
0:46:27 evaluated on their professional and financial viability. Do you think it creates more separation
0:46:30 and loneliness that men don’t have these kind of conversations or they feel embarrassed to have
0:46:36 these conversations? That’s such a good question, right? You know, sort of, as you talked about,
0:46:42 which is, you know, what are people posting on Instagram? All social media is marketing. And
0:46:46 if you’re not marketing, you’re not using it, right? Like, whether you’re marketing yourself or
0:46:50 something, it’s, that’s just what it is. All social media is marketing. And so, it’s fun to watch,
0:46:55 as you said, sort of how people market themselves. So, how women market themselves tends to skew
0:47:02 beauty, you know, and how men market themselves tends to skew wealth, you know, standing in front
0:47:08 of the Ferrari, the rented Ferrari. And I think you’re, I think you’re right. And just like we,
0:47:12 and there’s a, and to your point, there’s a lot of conversation about the dangers of social media
0:47:20 for women about creating unrealistic expectations of beauty, especially for young girls, and that
0:47:25 there’s no conversation about the unhealthiness of social media creating unhealthy expectations
0:47:30 for young men and boys. We don’t have that conversation at all. I think you’re 100% right.
0:47:38 And you and I have both talked about this, you know, the dangers of a lonely man, you know, you,
0:47:44 you know, show me, go to the Middle East with, you know, 25% unemployment in a shame-based society,
0:47:48 you’re a virgin and you’re living at home, you know, show me, show me somebody who’s committed
0:47:53 a mass homicide. And I’ll show you somebody that’s generally a lonely man.
0:48:00 Just as we wrap up here, I’ve had this whole wrap about if there’s one enduring skill that you’d
0:48:05 want to accrete to your children, it would be storytelling. That is the key to success across
0:48:10 almost every industry or real success. At the end of the day, you and I make a living storytelling.
0:48:15 And you’re, you’re outstanding at it. You know, I’m one of the, I don’t know,
0:48:19 30 million people that saw your kind of TED Talk that sort of, I don’t know if it made you famous,
0:48:23 but definitely took you to a new level without trying to be trying to be as
0:48:30 immodest as possible. What have you done? And what are your practices and hacks such that you can
0:48:36 maintain sort of your elite, you know, elite athlete status as a storyteller?
0:48:42 Thank you for that. Can I tell a story? I’ll be here all week, try the veal.
0:48:46 It was a former Undersecretary of Defense who was giving a speech at a large conference,
0:48:51 1,000 people, whatever. And while he’s giving his remarks, he takes a sip of from his coffee
0:48:56 that he’s holding in the Styrofoam cup and he smiles and he interrupts his own presentation.
0:49:01 And he says, you know, last year I spoke at this exact same conference, except last year I was
0:49:06 still the Undersecretary. And last year they flew me here business class. There was somebody waiting
0:49:10 for me at the airport to take me to the hotel. I got to the hotel. Somebody had already checked
0:49:13 me in. They just gave me my key. I came down in the morning. There was somebody waiting for me
0:49:18 in the lobby. They brought me to the same venue. They took me in the back entrance. They took me
0:49:23 into the green room and they handed me a cup of coffee and a beautiful ceramic cup. He says,
0:49:27 “I’m no longer the Undersecretary. I flew her coach. I took a taxi to the hotel. I checked
0:49:31 myself in. This morning I came down and took another taxi to the venue. I came through the front
0:49:36 entrance, found my way backstage. And when I asked somebody, “Do you have any coffee?” They pointed
0:49:41 to the coffee machine in the corner and I poured myself a cup of coffee in this year’s Styrofoam
0:49:46 cup. He says, “The lesson is the ceramic cup was never meant for me. I deserve a Styrofoam cup.”
0:49:54 I’ve tried to remember that. That it’s okay to enjoy the ceramic cups. It’s okay to
0:50:01 think about the ceramic cups. One ceramic cups. But at the end of the day, remember that it’s not
0:50:06 being given to me. It’s giving to the position I held in this moment. And when I move on,
0:50:11 they’ll just give it to the next person. It was never meant for me. And I think what that does
0:50:17 are two things. It reminds me where I come from, what I’m entitled to, and it also helps me live
0:50:23 in absolute gratitude. That anything that I get, all the ceramic cups I get to enjoy, I am grateful
0:50:29 for every one of them and think I deserve none of them. And so when you ask me sort of like what
0:50:36 helps me stay true as a storyteller, I think it’s very simple, which is I don’t view myself as an
0:50:41 expert. I view myself as a student. I generally think of myself as an idiot. I’m just more comfortable
0:50:49 with the idea of admitting it these days. And I really like learning. And so the stories I tell
0:50:54 are not actually for your benefit. The stories I tell are to help me make sense of the world.
0:51:00 And the stories I tell help me understand complex things. And if I’m going to explain something
0:51:04 to you, the best way I know how to do it is by telling the story that helped me understand it.
0:51:10 Last question. In five years, kind of first things that come to your mind,
0:51:16 if you’re sitting here in five years and the following one or two things that happened to you,
0:51:20 and that was success, what are those things? What boxes are you still looking to check?
0:51:31 I’m very sorry. I can’t answer the question. I’m living proof that having a plan means nothing.
0:51:37 My entire career was, I would never want to be a public speaker. I never wanted to write a single
0:51:43 book, let alone five. Like nothing I’ve done in my career was in the plan. My plan was thrown out
0:51:51 ages ago. I had one. It didn’t go that way. And so to me, the folly of a plan, it’s like
0:51:58 planning how many miles, it’s like planning which highway you’re going to take and how many miles
0:52:03 you want to drive per day, but not knowing the destination. It’s like figuring out these way
0:52:07 points. Like in three days, what city will you be at if you’re driving across countries? Like,
0:52:13 which direction am I going in? And my focus tends to be so far over the horizon to a
0:52:20 vision, an unrealizable idealistic vision, and the path that I take, I’m agnostic.
0:52:25 And so you’re asking me to tell you what the way point will be. I could tell you something,
0:52:33 and I can guarantee you it won’t happen. So I’m just trying to find the most efficient and fun path
0:52:39 to that crazy, far away place that I know I’ll never get to. And that’s
0:52:42 unnerving and more fun.
0:52:47 Wasn’t it Eisenhower that said plans are useless, but planning is invaluable?
0:52:56 And I think that’s true. I believe in backup plans. I believe in alternative routes. Like if
0:53:02 this one’s blocked, I’m going to go that direction for my career. I believe in going slowly in the
0:53:06 right direction versus speeding off in the wrong direction. So when companies talk about growth at
0:53:14 all costs, I’m like, for what reason? And I’m okay knowing that other people are driving faster
0:53:19 than me, because I know at some point they’ll hit a road. Not that I’m in competing against them.
0:53:23 I just know this from experience. When I was young in my career, I used to go to a guy.
0:53:29 He was very successful. He did similar things as me. He made a ton of money. I made none.
0:53:34 And he would say stupid shit like, I’m not getting out of bed for more than $25,000.
0:53:39 I won’t even get out of bed. And I was like, oh, shit, I do stuff for free all the time because
0:53:44 I really want to talk to somebody or meet somebody or sounds like fun. And he basically
0:53:49 spent most of the time I went to him for advice calling me stupid. Well, I can guarantee you’ve
0:53:55 never heard of him. And my career has faster passed him. And it’s not a competition and
0:54:02 there’s no gloating. For me, the lesson is I’d rather play the slow, steady game than the fast
0:54:08 game where I can show off to everybody. And understand how I think about my career. No
0:54:12 matter how much success I have, however you want to define it, I always think I’m still at the
0:54:17 tip of the iceberg because there’s so much more work to do. And I think focusing on what’s beneath
0:54:21 the ocean, I think keeps you humble and keeps you focused on all the work that has to be done.
0:54:25 But you’re asking me to tell you how much iceberg is going to be above the ocean and I couldn’t
0:54:30 tell you. Simon Sinek is an international speaker and bestselling author of the books,
0:54:37 Start With Why, The Infinite Game and Finder Why. He’s also the founder of The Optimism Company,
0:54:41 which provides programs for leadership development. He joins us from his home in Los
0:54:46 Angeles. Simon, I always enjoy spending time with you. We are so, you’re the most different person
0:54:51 I know that is the same person. And I think that’s what I enjoy so much about spending time with
0:54:57 you is we’re so similar from an exterior standpoint. And you just come at stuff from such a different
0:55:02 perspective as was me and it really illuminates. You just pointed something out to me that
0:55:07 it was sort of puncturing and that is sometimes I think when I’m advising people and I draw my own
0:55:12 experiences in, I think sometimes I’m boasting rather than just helping and I want to be more
0:55:18 cognizant of that. Anyways, brother, it’s always great to speak to you and congrats on everything.
0:55:24 Thanks. And I’m loving getting to know you. I really am. You know, you snuck up on me.
0:55:29 Go on. Like when I see your shit everywhere, legit, I smile like a proud parent. I’m like,
0:55:36 yeah, man, go, you know. And I just, I’m really, I can’t wait to come back to London and spend
0:55:38 more time with you, but properly. I appreciate that.
0:55:55 Out of happiness. I’ve been thinking a lot about grief. This was a rough weekend for me as I’m
0:56:03 sure it was for a lot of people. The news of the hostages being murdered by Hamas in Gaza, specifically
0:56:11 the story of a 23-year-old American Israeli Hirsch Goldberg, Pauline, who was wounded and
0:56:17 abducted by Hamas during the Nova Music Festival Massacre. He was held hostage for almost 11 months
0:56:23 until his body was recovered from Rafa in the Gaza Strip on the 31st of August, 2024. And I’ve
0:56:30 been thinking a lot about why that specific situation has inspired so much collective grieving,
0:56:38 given there’s spent so much death and destruction, both obviously among those killed on October 7th
0:56:43 and those taken hostage, but also so much grief and so much death and destruction
0:56:52 registered by people in Gaza. Why is this young man’s death so rattling? And I think it’s for a
0:57:01 few reasons. One, you can relate to it or they put a face on it. I saw the parents speak at the
0:57:08 Democratic National Convention and just seeing the grief, just so, just the just profound sadness and
0:57:15 anxiety on their parents’ faces. Any parent just looks at them and immediately kind of understands
0:57:20 or comes close to that horror and it puts a face on it. Whereas when we see news,
0:57:25 it just seems somewhat a little bit remote or distant, if you will. So I think it’s putting a
0:57:31 face on it. The story of parents obviously is very a gripping one. If you’re a parent, you just feel
0:57:42 such immense sadness. And I think what it does though, it informs your life. And that is what
0:57:46 you hoped for. And what I’ve tried to do last night, I was a real funk to try and get out of it,
0:57:53 was I thought, okay, the reason I have these fears, the reason I’m so worried about grieving is one,
0:57:57 anthropologically, it makes me a better father. It makes me think about protecting them. I’ve already
0:58:04 called my son today. It does make you a better, it does attach you to them. That fear of potentially
0:58:07 experiencing that grief, putting a face on it obviously from a current standpoint.
0:58:14 But also, as I think about this, it really is a function of the blessings you have. The
0:58:18 grief you feel is because you were put in a position where you were able to attach to others
0:58:22 and you were able to experience what is the most important thing in life and that is deep and
0:58:28 meaningful relationships. And some, I hope all of you listening out there, I would wish for all
0:58:33 of you a lot of joy and deep and meaningful relationships that don’t register grief, but
0:58:38 present the possibility of grief, which is nothing again, but receipts for love and means that you
0:58:44 have people in your life that you care a great deal about. This episode was produced by Caroline
0:58:48 Shagren. Jennifer Sanchez is our associate producer and Drew Burroughs is our technical
0:58:53 director. Thank you for listening to the PropG Pod from the Vox Media Podcast Network. We will
0:58:58 catch you on Saturday for No Mercy, No Malice as read by George Hahn. And please follow our
0:59:02 PropG Markets Pod. That’s right, the PropG Markets Pod, wherever you get your pods for the new
0:59:17 episodes every Monday and Thursday. Woohoo! Ka-ching! Mo money! Light up the rail. I want some Bolivian
0:59:23 marching powder. Where’s the, where’s the Dom Peragnon? I want some channel. I want for some bursace.
0:00:09 new season featuring marketing executives from the world’s most influential brands.
0:00:13 Tune in to hear what’s driving conversation in the fast-moving world of digital advertising.
0:00:17 The unique insights from brands is diverse as Hilton, Instacart, Moderna, Major League
0:00:22 Soccer, and more. And in this presidential election season, The Current explores when
0:00:26 a national political advertiser like the National Republican Senatorial Committee and
0:00:33 a major CPG brand like Hershey can learn from each other. Listen in and subscribe to The
0:00:40 Current at TheCurrent.com or wherever you get your podcasts.
0:00:43 Support for Prophety comes from Fiverr. Hiring top talent takes months, costing you time
0:00:49 and opportunities. Well, what if you could build your dream team today? With Fiverr Pro,
0:00:54 it’s possible it’s your all-in-one solution for premium freelance talent, offering hundreds
0:00:59 of categories to outsource complex projects. Immediately, their dedicated hiring experts
0:01:03 will help you find your perfect match. Plus, get access to project management tools, flexible
0:01:08 hiring options, and more so you can meet your hiring needs with ease. And the best part
0:01:13 is there are no hidden membership or subscription fees to get started. Visit pro.fiverr.com
0:01:19 to sign up and use code PROPHETY for 15% off any service.
0:01:23 Episode 315, 315 is the area code covering the North Central area of New York State. In
0:01:29 1915, the iconic Contour Coca-Cola bottle was patented. True story, I watched a documentary
0:01:33 on cocaine the other night and I’ve decided that from this point forward, I’ll do a little
0:01:38 blow before I watch anything. That’s right, my new viewing partner, White Girl Interrupted.
0:01:51 Go, go, go!
0:01:56 Welcome to the 315th episode of the PROPHETY pod. In today’s episode, we speak with Simon
0:02:01 Sinek, an international speaker and bestselling author of the books Start With Why, The Infinite
0:02:07 Game, and Find Your Why. I become friends with Simon. He’s one of my, like, speaking
0:02:12 thought leaders slash, I don’t know, friends, if you will. I met Simon or spent some time
0:02:17 with him at Summit at Sea, which I went on, I guess it was more than a year ago now, and
0:02:20 I had one of those moments with him that I will remember for the rest of my life. He
0:02:26 was in London and we were eating at Grangers, which is lovely, which is lovely. And when
0:02:30 I’m out in London, it’s usually twice a day, sometimes as much as five, sometimes as little
0:02:35 as zero. Someone will come up to me and say something nice. And someone locked eyes on
0:02:39 me, came over and I’m like, “Here it comes.” And they came up and said, “Your work is
0:02:43 just so meaningful. Thank you so much.” And I said, “Oh, that’s really nice of you.”
0:02:47 And he shook Simon’s hand and kind of laughed, but he would meant it for Simon, not for me.
0:02:52 And it was one of those moments where I realized what a fucking narcissist I am. Anyway, Simon,
0:02:57 and it happened again during the same lunch before Simon. He has a huge following and obviously
0:03:03 his content really resonates with people. All right, what’s happening? I’m back from the long
0:03:11 holiday. I take most of August off. I got a little distracted and that is my podcast partner on the
0:03:15 other podcast. I have another podcast if you didn’t know called Pivot. And it’s with this
0:03:20 little lady named Kara Swisher and we were invited to the Democratic National Convention.
0:03:26 So, got my ass to Chicago, interrupted my holiday only to find out my security clearance had not
0:03:30 been cleared. I mean, they let in, what’s that guy’s name? Charlie Kirk. They let in like every
0:03:35 Joey Bagadona influencer in the world. It’s like, if you had, I don’t know, over 800 followers on
0:03:40 Instagram, they let you in. But I found out when I landed there that my badge, my security clearance,
0:03:46 had not been approved. So, I immediately took to whatever it was, some social to bitch about it.
0:03:52 And the conjecture was why are you not being allowed into the United Arena? I started going
0:03:57 over my history. I have never been arrested, released a dog. I was held up at, I was imprisoned
0:04:01 at the Nobu Chicago waiting to get into the DNC. Generally, I found the DNC, I thought it was very
0:04:07 well orchestrated. Too long. Too long. It should be three days not four days. Generally, like a great
0:04:13 vibe. I went to the one in 1996. I’ve always been a bit of a political junkie. And I went knowing
0:04:18 nobody and I met this guy and we ended up sharing a room so we could, I was so broke when he was
0:04:23 broke too when we were both there, total tourists. And I think we lied about our names to get into
0:04:27 a bunch of parties. I got to see Al Gore dance at one of the parties. That was kind of the highlight.
0:04:33 Anyways, but I was at the Democratic Convention. What was it? I guess that was 28 years ago when
0:04:38 Clinton was renominated for his second term. I spent time in New York. By the way, New York’s
0:04:42 on fire. It’s just on fire. I don’t care what anyone says. I think New York right now is in a golden age.
0:04:47 That’s about it. I’m mostly just talking about, oh, I went to Nat Tuckett. That was wonderful.
0:04:51 Anyone who’s been there, it’s basically a sandbar in the middle of the Atlantic. It’s
0:04:56 absolutely gorgeous. The thing I love about it is my kids can roam free and get into trouble.
0:05:01 Although it’s such a bummer they keep finding all these great whites everywhere around there. So
0:05:07 I’m just a total mess when my kids go into the water. And then I ended with an idea to speaking
0:05:14 in Brazil. Oh my God, beef, beautiful people. And what I think is arguably the best hotel in the
0:05:21 world right now, the Rosewood, Sao Paulo, what is not to like about Brazil? Seriously. I mean,
0:05:25 it’s just such an amazing, I think it’s probably my favorite place to go, right? It’s actually
0:05:29 my favorite place to go. Yeah, that’s outside of the US. I absolutely love it there. And I went to
0:05:34 the XP conference, which had 50,000 people. It made me want to buy stock in Brazil or buy,
0:05:40 I don’t know, the ETF on the Bolsa or whatever. I think it’s such an impressive culture and people
0:05:46 work hard and love to play hard. The people and the dress there, I was especially impressed with
0:05:52 the dress. Now, granted, I saw a pretty limited slice between the Rosewood and the Soho since
0:05:56 Sao Paulo, but it really is an impressive culture and had a wonderful time there. Just so fucking
0:06:00 far. Is there anything you can do about that, Brazil? Just a little too far. And speaking of
0:06:06 which, on the 11-hour flight yesterday, which leaves at 4 p.m., which makes no fucking sense,
0:06:11 I totally loaded up on movies. I watched “The League” or “The Syndicate of Un-Gentlemanly Warfare,”
0:06:15 which is a Guy Ritchie film. I enjoy his films because they’re so beautiful. And he has beautiful
0:06:22 men and beautiful clothes. And then I watched, oh my God, “Saltburn.” Jesus Christ. I had to
0:06:28 stop it because it was just like too much for me. It was like a little too much for the dog to
0:06:33 handle. I just kind of put my head in between the pillows and was like, “Calm down, take me to
0:06:39 a park with a bunch of tennis balls.” Anyways, an outstanding, what do I call it, outstanding?
0:06:44 Great. Hovering between great and outstanding. But Jesus Christ, that shits a lot. And a real twist
0:06:50 at the end, kind of like a crime game level twist that I did not see coming. I did not see coming.
0:06:54 I can usually guess everything that’s happening in the movie. I’m the kind of jerk that in the
0:06:58 movie leans over to my partner and says, “Oh, you know, the butler did it or whatever.” But yeah,
0:07:03 I did not see that one coming. And then I watched “Napoleon.” “Napoleon” because I like war films.
0:07:08 I thought it was pretty interesting. I did not realize that Napoleon was so obsessed with Josephine.
0:07:12 I thought it was interesting. I would not want to live in France in late 19th century. It seemed
0:07:18 like a pretty violent place where everybody would have their time in the sun and then they cut their
0:07:25 heads off. But I love warfare. I’m interested in war history. Napoleon’s Bonaparte or Napoleon’s
0:07:30 Waterloo, if you will, or him venturing into Russia, started with 400,000 troops, returned
0:07:37 with 40,000, was exiled once, then came back. And his troops really embraced him and then exiled
0:07:41 twice. I just thought it was, I thought it was fascinating. Was it a great film? No. Ridley Scott
0:07:46 is just fun to watch because he gets so much, such big budgets. And the cinematography was so
0:07:50 incredible. And Joaquin Phoenix is obviously a fantastic character. Anyway, those are my
0:07:56 three films. So in order, salt burn, I would definitely see but brace yourself. Napoleon,
0:08:03 if you like war history and the League of Ungently Warfare, I’d say pass or wait till it’s
0:08:07 on Netflix or it’s already on Netflix. I just thought it was just okay. All right, enough about
0:08:13 our travels. We have some news to share here at PropG. Starting next week, we are launching another
0:08:19 podcast called “Raging Moderates.” It’s a PropG podcast co-hosted with our favorite political
0:08:25 gangster and rising star, Jessica Tarlov. If you don’t know Jessica, she is a co-host on the five,
0:08:29 Fox’s weeknight news program and plays a key role in special coverage for the networks.
0:08:35 Everything’s so polarizing. I think it myself is kind of, I don’t know, squarely in the middle.
0:08:38 And I love the term “Raging Moderates.” I said leading up to the election and if it works, maybe
0:08:43 after. Let’s try and explore all views of this using data. Essentially for business reasons,
0:08:48 we should not be doing politics because you just turn off people. Advertisers don’t like it,
0:08:52 but I can help it. I’m interested in it. I think it touches on everything, society, technology,
0:08:56 the economy. And I think it’s, if you want to understand America, if you want to understand
0:09:02 our economy, you need to have some basic rooting in politics. Plus, I just think it’ll be fun.
0:09:08 Anyways, so with that, we hope you enjoy “Raging Moderates.” Love that title. Love that. I came
0:09:13 up with that. I came up with that. A weekly podcast from the PropG universe. New episodes will be
0:09:20 right here on the feed every Tuesday to resist is futile. We’re fucking AOL in the 90s. You stick
0:09:30 your hand into a cereal box and you’re going to get the dog. We’ll be right back for our conversation
0:09:39 with Simon Sinek. Support for PropG comes from Netsuite. There’s no sure far way to predict what’s
0:09:43 coming next to your business. You can look at lots of graphs. You can listen to all of my podcasts.
0:09:48 You can even consult a high-price psychic, though I don’t recommend it. So how can you prepare for
0:09:52 anything when there are so many unknowns right around the corner? Smart businesses have gotten
0:09:56 themselves future ready with Netsuite by Oracle. Netsuite is a go-to business management suite
0:10:01 for almost 40,000 companies offering everything you need to stay on track, no matter what tomorrow
0:10:05 brings. Netsuite combines accounting, financial management, inventory, HR, and more into one
0:10:10 simple platform offering a single source of truth. Get real-time insights and data you can use to
0:10:15 make the right decisions faster than ever before. Don’t get caught looking backwards. Get ahead of
0:10:21 the curve and stay focused on what’s coming next with Netsuite by Oracle. Speaking of opportunity,
0:10:27 you can download the CFO’s guide to AI and Machine Learning at Netsuite.com/PROF. This guide is free
0:10:39 to you at Netsuite.com/PROF. That’s Netsuite.com/PROF. Support for this show comes from Betterment.
0:10:43 Do you want your money to be motivated? Do you want your money to rise and grind?
0:10:48 Do you think your money should get up and work? Don’t worry, Betterment is here to help.
0:10:52 Betterment is the automated investing and savings app that makes your money hustle.
0:10:56 Their automated technology is built to help maximize returns, meaning when you invest with
0:11:01 Betterment, your money can auto-adjust as you get closer to your goal. Rebalance if your portfolio
0:11:06 gets too far out of line and your dividends are automatically reinvested. That can increase the
0:11:11 potential for compound returns. In other words, your money is working like a dog while you can be
0:11:17 sleeping like one and snoring like one too. You’ll never picture your money this same way again.
0:11:21 Betterment, the automated investing and savings app that makes your money hustle.
0:11:26 Visit Betterment.com to get started. Investing involves risk. Performance is not guaranteed.
0:11:35 Support for Prop G comes from Mint Mobile. If you’re serious about keeping your budget in
0:11:40 check, your monthly expenses are one of the first places to look. And one thing a lot of us over
0:11:45 pay for is our phones, especially between all the hidden fees and other nonsense phone companies
0:11:51 throw at you, which is why Mint Mobile is doing things differently. When you switch to Mint Mobile,
0:11:55 you can get three months of premium wireless service for just 15 bucks a month. All of Mint
0:12:00 Mobile’s plans come with high-speed 5G data and unlimited talk and text. Plus, you don’t need
0:12:04 to worry about getting a new device or phone number. Just bring those with you over to your new
0:12:09 Mint Mobile plan. To get this new customer offer and your new three-month premium wireless plan
0:12:15 for just 15 bucks a month, you can go to Mint Mobile.com/PropG. That’s Mint Mobile.com/PropG.
0:12:22 You can cut your wireless bill at 15 bucks a month at Mint Mobile.com/PropG. $45 up from payment
0:12:27 required equivalent to $15 a month. New customers on first three month plan only. Speed slower above
0:12:33 40 gigabytes on unlimited plan. Additional taxes fees and restrictions apply. See Mint Mobile for details.
0:12:51 Welcome back. Here’s our conversation with Simon Sinek, an international speaker and best-selling
0:12:55 author of the books Start With Why, The Infinite Game, and Find Your Why.
0:13:00 Simon, where does this podcast find you? I am back home in Los Angeles.
0:13:06 So, let’s bust right into it. You describe yourself as an unshakable optimist, and I’m
0:13:11 a naturally pessimistic person. So, I’m curious, how do you maintain your optimism,
0:13:14 especially in challenging times, and what advice would you give to someone
0:13:19 who tends to be, like myself, kind of see the glasses half empty, if you will?
0:13:26 So, optimism doesn’t mean I’m naive nor blind, and it’s not blind positivity. It’s not looking at
0:13:32 a broken world and be like, “Everything’s fine. That’s not how I am. I’m quite cynical a lot of
0:13:37 the time.” But I generally believe that the world tends toward good, and I believe that even if we’re
0:13:42 in darkness, that if we come together and work together, we will get through this, and we will
0:13:46 come out better than we went in. So, it’s the undying belief that there’s a light at the end of the
0:13:52 tunnel. And you’re sort of known as the leadership guy or the why guy, I guess. Break down for you,
0:13:56 what is the definition or the key to effective leadership?
0:14:01 I think leadership is an incredibly misunderstood subject. I shouldn’t really
0:14:09 have to write books about it. I visited rural Kenya recently and met some people who we would
0:14:16 describe as poor. And one of the mamas, she organized a women’s empowerment group where
0:14:19 they sort of help each other out, and she was telling us how she does it and how she
0:14:24 overcomes some of the challenges. And literally, she was telling me stuff that I’ve written about.
0:14:29 In other words, she’s a brilliant natural leader, and she doesn’t do it out of some sort of
0:14:33 philosophical construct. She does it because it’s practical and it works. And if people are
0:14:38 seen and heard and taken care of and feel like they can trust each other, they’ll take risks,
0:14:43 they’ll open up, they help each other. For me, leadership is the awesome responsibility to see
0:14:48 those around us rise. And what we can do when we’re in a position of leadership, whether it’s
0:14:52 formal or informal, rank does not mean that you’re a leader. It just means you have authority.
0:14:57 But if you’re in a position of formal or informal leadership, that you look to the left and look
0:15:01 to the right and say, “What can I do to support?” You’ve often talked about the distinction between
0:15:05 natural born leaders and leadership developed as a skill, and you’ve said that you think it can be
0:15:10 developed. If someone is young, I think I want to have developed those leadership skills. What are
0:15:17 some exercises for doing that? I mean, first of all, I don’t believe leaders are born. I think that
0:15:21 some people have an education when they’re younger. They have a coach, they have a parent,
0:15:26 they have a guardian, somebody in their life, a teacher who does something right. They model
0:15:30 some themselves after that person, and they seem to learn it younger, or they have some trials and
0:15:35 tribulations, and they learn to overcome and rely on other people, whatever it is. But even
0:15:40 some of the great leaders that we admire, if you look back, whether it’s Steve Jobs or Mahatma Gandhi,
0:15:45 you see that they were learning and they didn’t get it right a lot of the time, especially when
0:15:50 they were younger. They learned those skills. For me, fundamentally, the single best thing
0:15:58 a young person can do is really learn to be a friend, learn to put away a device, and learn how
0:16:04 to engage with another human being, learn how to be there for someone, learn how to accept help
0:16:09 when it’s offered, learn how to ask for help, and all of these pretty fundamental things about
0:16:15 adolescence. When we’re very, very young, the only thing we want or need is the approval of our
0:16:19 parents. Look, daddy, look what I made. Watch me jump over the step, and then we give them positive
0:16:23 reinforcement, and all that serotonin flows, and it feels really good. And literally, nobody else
0:16:29 matters except mom and dad’s approval. That’s it. When we reach adolescence and all the hormones
0:16:36 start flowing, we make this change, this conversion where we now crave the approval of our friends
0:16:43 and our peers. Very stressful for us, very frustrating for our parents who are watching
0:16:48 us change. Really essential for a human being to learn to acculturate for the wider group outside
0:16:53 of their immediate family. And so it should be natural that we learn to ask for help from friends
0:16:58 and learn to give help to our friends. So to be a great leader, learn friendship.
0:17:03 You’ve equated it to being a parent that is leadership. What did you mean by that?
0:17:09 Well, you don’t get to choose your kids, but you love your kids and you want to raise them to be
0:17:14 the best that they can be. You don’t often get to choose your team if you’re promoted into position
0:17:22 of leadership, but you still get to celebrate them and try your best to help raise them to be the
0:17:27 best that they can be. And there are a lot of similarities and a lot of things that you can
0:17:32 learn about leadership you can learn from parenting books. For example, affirming a child’s feelings.
0:17:36 You know, dad, I’m sad. No, you’re not. It’s fine. It’s good. What do you have to be sad about? Your
0:17:43 life is great. That’s bad parenting. You want to affirm the kids feelings. Same at work, you know,
0:17:47 to talk people out of their feelings makes them feel unseen and unheard. Good leadership overlaps
0:17:52 a lot with good parenting because it’s interaction with other human beings working to see them build
0:17:57 confidence and be the best that they can be. And sometimes we have to be patient to let them try
0:18:02 again. What do you think the biggest mistake that leaders or managers make? I mean, you mean you
0:18:07 talk about management versus leaders. Nobody wakes up in the morning to be managed. Nobody says,
0:18:12 “I’d like to be managed, please.” But we would all like to be led. And I think what you’re doing is
0:18:16 highlighting the problem. A lot of leaders act like managers. You can manage a process, you can
0:18:21 manage a company, but you can’t manage people. You can lead people. And I think when we start
0:18:29 managing people as if they are a process, things start to break down. And I think another very,
0:18:35 very, very common mistake that newly minted leaders make is they believe that their intelligence
0:18:41 or capacity or their ability to give answers to every question is what gives them their credibility
0:18:46 to lead. And so you’ll see a lot of leaders lying, hiding and faking. They won’t admit if they don’t
0:18:50 know something. They won’t say, “I don’t know.” They won’t ask for help because they fear that
0:18:55 undermines their credibility, which is completely false. We get a lot of questions about mentorship.
0:18:59 So I’ll turn the question to you. What advice would you give someone who’s looking for a mentor?
0:19:05 How do they go about finding a mentor? So when my career was just sort of getting going,
0:19:12 I was introduced to this guy named Ron Bruder. Ron, a very, very accomplished entrepreneur,
0:19:18 really successful. And he was charming and lovely and super helpful and wonderful in our meeting.
0:19:24 And about a week or two later, I called Ron, who’s a very busy man, and he took my call.
0:19:29 And a few weeks later, I called him again. I needed some advice. And he took my call again.
0:19:34 And at some point, we went out for lunch. And eventually, this sort of mentor-mentee relationship
0:19:40 evolved. And I thought of him as my mentor. And I remember we became quite close. And I remember
0:19:45 I was leaving his house one day, and I used the M word for the first time. And I put my arm around
0:19:49 him as I was saying goodbye. And I said, “You know, Ron, I’m glad you’re my mentor.” And he said
0:19:55 something back I didn’t expect. He said, “And I’m glad you’re mine.” And this is what I think
0:20:01 great mentor relationships are, which is it’s both of us are mentors and both of us are mentees.
0:20:05 Somebody who’s had more experience is still learning about the world from somebody who’s
0:20:09 asking for help. However, I think they do evolve like friendships. I don’t think you can go up
0:20:13 to some random person and say, “Will you be my mentor?” Just as you can’t go up to some random
0:20:18 person on the street and say, “Will you be my friend?” It’s a relationship. And for me, the
0:20:23 definition of a mentor is someone who always has time for you. And it can’t be one-sided. You
0:20:26 can’t simply just because someone’s accomplished and you’re not, you can’t just go up to them
0:20:31 and think they’re an asshole because they don’t want to mentor you, just like you can’t think
0:20:34 someone’s an asshole because they don’t want to be your friend. It’s a relationship. And there’s
0:20:39 a lot of sacrifice that comes with it. What I love about mentorship is a mentor is not a champion.
0:20:46 I think people mistake them. Like in a company, you can have champions who can go to bat for you
0:20:50 and put in a good word for you. You can get that promotion. And the best mentors are not in your
0:20:55 chain of command. They’re either outside of your department or even better outside of the company.
0:20:59 And the only thing they care about is you and your growth. And there’s nothing they can do to
0:21:05 interact, intervene. It’s a very pure relationship where you both learn, you both give, and you
0:21:10 show up for each other. Yeah, it’s interesting. I really have had a lot of mentors, but I’ve
0:21:15 never ever asked anyone to be my mentor. I’ve asked for help. Or I said, “Can we grab coffee?”
0:21:19 And like you said, the relationship, the relationship evolves.
0:21:25 Talk about the tension between self-actualization and putting a group’s needs first. You write
0:21:29 a lot about this. Does that tie into what you’ve spoken about regarding leadership?
0:21:39 I mean, you’re hitting a nerve for me. Mas loves hierarchy of needs. That’s self-actualizations
0:21:47 at the top. Mas left me with a bit of a mistake, which is if you look at the hierarchy of needs,
0:21:51 at the bottom, the most basic need he articulates as food and shelter.
0:22:02 And the third rung up is relationships. Now, I’ve never heard of anybody dying by suicide
0:22:06 because they were hungry. I’ve heard of people dying by suicide because they were lonely.
0:22:11 In other words, it seems to be inconsistent with reality that food and shelter would come
0:22:19 number one, but not entirely. Basically, being human is a paradox. Every moment of every single day,
0:22:23 you and I are both individuals, we’re ourselves, but we’re also members of groups. We’re members
0:22:30 of teams, churches, families, whatever it is. And we are confronted with little and big decisions
0:22:34 on a regular basis. Do I put myself first at the sacrifice of one of the groups? Or do I put
0:22:39 the group first at the sacrifice of myself? And people debate this. You always put yourself first
0:22:42 because you can’t help the group unless you’re healthy. You always put the group first because
0:22:45 they won’t be there for you unless you take care of them. And the answer is you’re both right
0:22:50 and you’re both wrong. It’s a paradox, and it’s difficult, and it’s messy. And so Mas love only
0:22:57 considered us as individuals. As individuals, if we lived like great white sharks, 100% correct,
0:23:03 number one would be food and shelter. But as members of groups, it’s different,
0:23:08 and there’s new ones. And so it’s this constant battle between the two. And the thought of living
0:23:13 an entire life to get to the top of a pyramid called self-actualization, where we look down at all
0:23:21 the unactualized people, seems antisocial versus shared actualization, which is raising the team,
0:23:28 raising the company, raising the society, raising the nation. That to me seems more pro-social.
0:23:35 And so good leaders, I think, are doing that. They recognize the paradox. They struggle with
0:23:42 the paradox. But at the same time, they work tirelessly to bring the group that we all rise
0:23:45 together to share an actualization, that we all are working to something bigger than ourselves.
0:23:52 I saw you on the Diary of CEO podcast, and you spoke about people struggling to make friends.
0:23:57 Can you say more about why you think modern society makes it so difficult for people to
0:24:04 develop deep, meaningful relationships? I mean, there’s a host of reasons. No one reason
0:24:09 is the reason. I mean, it’s easy to blame cell phones and social media, and they definitely
0:24:13 play a role, and I think they definitely exaggerate it. I don’t think they’re the sole cause.
0:24:17 Parenting is a big part of it as well. I mean, you and I have gone to restaurants,
0:24:23 and you look over to the table next door, and the parents have slapped an iPhone or an iPad in front
0:24:28 of their little children because they don’t want noisy kids at dinner. They could have brought
0:24:34 colored pencils, and so parenting is a large part of it as well. You see this in education
0:24:38 reform. You talk to teachers or superintendents. They’re all in favor of education reform. Even
0:24:43 the students are up for it. It’s the parents who are often the most resistant because I want you
0:24:49 to reform education, but just don’t experiment on my kids. Cell phones are the same. Schools
0:24:53 want to get rid of them. It’s the parents who are put pressure to say absolutely not, you may not.
0:25:04 I think it’s dramatically exaggerated by the devices, but I also think it’s the
0:25:11 whole thing. Our society, and this goes back a few decades, we’ve over-indexed on rugged
0:25:18 individualism, where it’s all about you, your strength, and we don’t value as much team
0:25:25 celebration, team effort. We did this, not I did this. I don’t know if you ever saw Elizabeth
0:25:32 Gilbert’s TED Talk, but it was magical, and it was hugely helpful to me. She talks about the concept
0:25:40 of genius, and then the pre-renaissance. A genius was a daemon, a spirit that lived in the walls,
0:25:47 and if you did something great, people would say of you, you had your genius. Your genius was with
0:25:51 you, so you couldn’t take full credit for your accomplishments. If you failed, people would say,
0:25:56 “Oh, I’m sorry, I guess your genius wasn’t with you.” You couldn’t take full credit, but you never
0:26:01 had to beat yourself up if it didn’t go so well either. At some point in the renaissance,
0:26:07 having your genius became being the genius. Now, if you accomplish something great, people said of
0:26:12 you, “You are a genius, and now you’re labeled and straddled with that stress for the rest of your
0:26:17 life, and the fear of not being the genius anymore becomes part of the identity, which I think is
0:26:23 part of the failure.” But I think what we’ve done is it’s all part of the package of this over-indexing
0:26:29 on this rugged individualism, especially in America, where we’ve heroized CEOs, and we’ve heroized these
0:26:34 individuals who none of them accomplished their stuff by themselves, but we don’t celebrate the
0:26:41 team, the group, as much. I think it’s acidal. I think it’s part of one of the unfortunate side
0:26:49 effects of Jack Welch and Milton Friedman economics of the ’80s and ’90s, which we’re trying to undo
0:26:55 over the course of these years. Yeah, I think it’s also not uniquely American phenomena, but American
0:27:00 phenomenon. That is, we like to think we live in a meritocracy, and anyone can be anything,
0:27:06 and that’s a very nice aspirational bumper sticker. But if you believe that, the dark side of that is,
0:27:11 well, if it’s truly a meritocracy, and anyone could do anything, then if you don’t end up wealthy,
0:27:16 and in a position of influence, you fucked up. I mean, I know you know this, and I know this.
0:27:20 A lot of our success is not our fault. At the same time, when we screw up, a lot of that is not
0:27:25 your fault. But it feels very American to put pressure on people that if you don’t end up in a
0:27:35 certain position, it’s on you, brother. I completely agree. I mean, I’ve always tried to live with the
0:27:50 formula, the notion that success is the zero sum of effort, talent, and luck. And you want to
0:27:55 get keep those things somewhat, they’re imperfect, and they sort of go like this, but at some point,
0:28:02 they lead to one. So for example, if you win the lottery, no effort, no talent, pure luck, not
0:28:08 stable. If you work really, really hard, but you’ve got no talent, you had no luck, you’re
0:28:12 not going to succeed either. And it’s just really frustrating. And if you have talent that you don’t
0:28:17 capitalize on, again, and so I think you and I both recognize that we’ve tried to steer in our
0:28:23 careers in a direction where we’re more likely to do better than not. Like if I’m really good at math,
0:28:29 I should probably point myself in a direction where math is needed. And if I’m, you know,
0:28:35 maybe not be a football player if I have no athletic ability, no matter what my dreams are,
0:28:39 you know, so we try and point ourselves, we have an unfair advantage because of our natural gifts,
0:28:45 work hard and hope that things work out, you know, you cross your fingers a little bit and
0:28:52 it happens. I’m not the most disciplined person in the world. I have seriously bad ADHD, which means
0:28:57 I struggle to read books. People think I’m really well read. I’m not. I’ve written more books than
0:29:04 I’ve read. And yet I found ways to navigate these things rather than make them bowls and chains.
0:29:10 My sense is you also have a pretty authentic voice, but it’s not easy to manage. I’ve mostly
0:29:16 been able to screen out feedback from social media, mostly, but some of it gets so angry and so
0:29:21 vile. Sometimes it’s difficult to screen out. What do you do to manage and try and maintain
0:29:27 that authenticity without, you know, getting upset all the time and all the shit we get online?
0:29:32 Yeah, I work very hard not to be political. Like I don’t give to candidates. I don’t endorse
0:29:38 candidates. I won’t go to fundraisers. I believe in bipartisanship. So I’ve spoken at Republican
0:29:42 congressional off-sites. I’ve spoken to Democratic congressional off-sites and I give them the same
0:29:48 message because I want unity. So if I preached bipartisanship and picked aside publicly,
0:29:55 then I’d be full of it. So one part is, is I believe that the work that we do is bigger than
0:30:01 politics. And so I try and play at that level. And who I vote for is my business, registered
0:30:07 independent. And I also, in terms of like, because the overwhelming pressure, especially when anything
0:30:13 happens socially, the overwhelming pressure from friends and fans alike to weigh in, it is sometimes
0:30:21 well, high stress, high pressure. My rule has always been that I will, that I will only say
0:30:25 something publicly if I believe that I can be additive. And if it takes me a week to come up
0:30:31 with something that’s additive, then I’m going to wait a week. And it’s very hard to resist the
0:30:40 pressure, but I don’t want to simply add to noise simply because a certain base wants me to join
0:30:46 their side. My rule is it has to be additive. It has to be additive. And by the way, sometimes
0:30:52 I have nothing to say that’s additive. And so I will sometimes be conspicuously quiet. I only
0:30:59 want to contribute, not just, not just virtue signal. It’s funny. I actually thought about you
0:31:04 because in an unusual context, when all these videos emerge, JD Van saying that the world is
0:31:12 being run by these lonely, hateful people without children who have cats. I’m one of them. I thought
0:31:18 of you. I thought, Simon has never been married. It doesn’t have kids. I know you really value
0:31:22 your relationship with your nieces and nephews. And my sense of you is you have a lot of friends
0:31:28 and a good support network. Do you get lonely? Do you feel like you’re judged sometimes for not
0:31:33 going the traditional route in terms of relationships and kids? 100%. So those are two
0:31:42 different questions. I’ll deal with the second one first. So I have a friend who was in a very,
0:31:51 very dysfunctional 16-year relationship. He had, it was just chaotic and dysfunctional. And she’s
0:31:55 been out of it for a few years, but she’ll freely admit that she probably should have been in it
0:31:59 for a year. And she always felt that she could fix him and save him. I don’t know what it was,
0:32:05 16 years of a committed monogamous relationship. I’ve never been married.
0:32:13 My longest relationship was three years. And the world judges me. When I go on dates, like,
0:32:18 women will say to me, “What’s wrong with you?” Some of my friendships are better and closer and
0:32:24 more loving than a lot of marriages or monogamous relationships. And certainly, the life that I
0:32:28 live and the friends that I have are better than that relationship. But why is it that society
0:32:33 says that she’s healthier and I’m unhealthy or she’s correct and there’s something wrong with me?
0:32:38 When people say, “Why haven’t you been married?” I might say, “Isn’t it obvious I haven’t met the
0:32:44 right person yet?” Like, “Isn’t that obvious?” For whatever reasons, I think we’re starting,
0:32:49 we’re in a time now where people are becoming more open to different types of relationships,
0:32:55 that people can be in union without a marriage, raise a family without the marriage. And society,
0:33:00 for the most part, says, “So long as you’re good parents and so long as you’re doing right by each
0:33:05 other and the kids, have at it.” You don’t necessarily need the religious or the legal
0:33:11 document to have the family. And society is more open to that than it used to be. And so,
0:33:19 I’m hoping that society starts to recognize that having fulfilling friendships, having fulfilling
0:33:23 relationships, and by the way, many people would say that the only difference between a close
0:33:27 friendship and a marriage is you can have sex with your spouse. But it turns out you can do
0:33:33 that with friends too. You can be very fulfilled. So, I think you’re right. I absolutely have been
0:33:40 judged my whole life. And the older I get, the judgment is even harsher. And yes, like any human
0:33:45 being, I get lonely. I get lonely. People in relationships get lonely. But yes, of course,
0:33:52 I get lonely. But this is why I love my niece and nephew so much, is because I don’t have my own
0:34:01 kids. They have a little bit of my DNA. And I get to give love to these aspiring magical little kids,
0:34:05 not a little anymore. And I get to impart everything that I’ve learned and who I am
0:34:10 in a way that a parent can’t. I can get away with stuff as an uncle that a parent can’t,
0:34:16 which I know contributes to their lives. And I love that. And they’re both at camp right now,
0:34:20 and I miss them desperately. You know this. You know this. When you had kids that profoundly
0:34:28 changed everything about the way you viewed your life. And I see how you bring your son
0:34:31 with you. So, I’ve just been watching your Instagram and how you bring your son on your
0:34:35 business trip. And you bring your son to games. And you know, you’re trying to give him the
0:34:42 craziest experiences that he can have. And what an amazing thing that, like it’s an amazing thing
0:34:48 to live an amazing life. It’s even more amazing to share it. And define amazing however you want.
0:34:52 But to go on an adventure with a person, I find vastly more fulfilling than going on an adventure
0:35:02 alone. We’ll be right back. Support for PropG comes from LinkedIn. As a B2B marketer,
0:35:06 you know how noisy the ad space can be. If your message isn’t targeted to the right audience,
0:35:11 it just disappears into the noise. With LinkedIn ads, you can work with precision and reach the
0:35:16 professionals who are more likely to find your ad relevant. With LinkedIn’s targeting capabilities,
0:35:21 you can reach them by job title, industry, company and more. You’ll have direct access to and build
0:35:27 relationships with decision makers. That’s a billion members, 130 million decision makers
0:35:31 and 10 million C level executives. You’ll also be able to drive results with targeting and
0:35:37 measurement tools built specifically for B2B. In technology, LinkedIn generated two to five times
0:35:42 higher return on ad spend than any other social media platforms. And 79% of B2B content marketers
0:35:47 said LinkedIn produced the best results for paid media. Start converting your B2B audience
0:35:51 into high quality leads today. We’ll even give you $100 credit on your next campaign.
0:35:58 But a LinkedIn.com/Scott to claim your credit. That’s LinkedIn.com/Scott. Terms and conditions
0:36:07 apply. LinkedIn, the place to be, to be. Support for this podcast comes from Huntress. Keeping
0:36:12 your data safe is important. However, if you’re a small business owner, then protecting the information
0:36:18 of yourself, your company and your workers is vital. And comes Huntress. Huntress is where
0:36:23 fully managed cybersecurity meets human expertise. They offer a revolutionary approach to managed
0:36:28 security that isn’t all about tech. It’s about real people providing real defense. When threats
0:36:33 arise or issues occur, their team of seasoned cyber experts is ready 24 hours a day, 365 days a
0:36:39 year for support. Visit huntress.com/propg to start a free trial or learn more.
0:36:46 A Spotify, no matter the type of small business you own, upgrading your lighting or refrigeration
0:36:51 can save you energy and money on your electricity bills. And we’ve got you covered with incentives
0:36:55 to reduce the upfront costs. Visit bcihider.com/incentives to learn more.
0:37:03 I’ve gotten to know you a little bit. And what’s interesting is we’re, we’re actually quite similar
0:37:08 in terms of our profession. And I think I’ve achieved you more so, but achieved certain levels
0:37:12 of success and thought leadership, whatever the hell you want to call it. But what really struck
0:37:17 me was one of the major differences on the, on the front end, I think people say, oh, they’re
0:37:22 similar doing the same thing the same way. You’re really about kind of ideas and impacting people.
0:37:27 And whenever I start to talk about business or we share business ideas or talk about money,
0:37:32 your eyes glaze over. And for me, and I’m not, I’m, I’m not proud of this.
0:37:37 Money is like right up there for me or business or like building successful business that I can
0:37:43 monetize. And as I’ve gotten older, I’ve got much better at sharing it. But you’re, you really are
0:37:48 about the ideas. I’m more about the ideas for me are really interesting and I love it. But it’s
0:37:54 a means to, I want to build a robust business. And, and I thought was just so we’re built much
0:37:59 differently that way. Any thoughts? I mean, you’re right. You, you like the money and the success
0:38:05 and the ideas are the means to that. And I’m the opposite, which is I like the ideas and the
0:38:12 business, if the ideas are good, then the business will follow as for me, the, the, the value that
0:38:17 other people put on, on the things that I put out in the world are proof that the, the ideas have
0:38:22 value. Jesus, I sound awful. I, we’ve got to cut this out. That’s like, your rap is so much better
0:38:28 than mine. And then that, that is such a better way. Did you know, no, I, and I’ll tell you why
0:38:37 I disagree with you is you’re honest. Like if, like if investment banks took their stupid purpose
0:38:41 statements down about how they want to help the world or share something or build economies,
0:38:47 which is complete nonsense. And if CEOs of a lot of companies simply said, look,
0:38:53 we’re just here to make cash. I want to get rich. I want the people around me to get rich.
0:38:58 These shareholders want to get rich. We’re going to help them get rich. And we’re going to try and
0:39:03 make a great product for you in order to get rich. I had actually be, that’s what they’re doing.
0:39:07 We all know that’s what they’re doing. They’re just lying to us and saying that other things are
0:39:14 more important. And so the honesty, quite frankly, means that I know what I’m getting and I know how
0:39:20 to invest. And I know how to, I know what level of trust or what barriers or what to believe.
0:39:25 And so, because right now it’s so hard to know what to believe because everybody’s bullshitting us.
0:39:32 And so I find your attitude so refreshing. And you and I are tortured by different things.
0:39:38 And we’re tortured by the, probably the thing that we put second. Like I’m, I’m tortured
0:39:43 that I’m not good at the structure stuff. And like, and you, you sort of say, you know,
0:39:46 you’re more successful than me in terms of this thought leadership, which I don’t even see.
0:39:54 I mean, you’re, you’re, your game is so good. And I, I’m like, I, even though when we first met,
0:40:02 we, I remember when we first met and I was like, okay, it’s kind of a little bit grumpy,
0:40:09 definitely pessimistic where I’m optimistic. I like him. I respect his work, friendship, maybe,
0:40:13 right? And the more I’ve gotten to know you, and we don’t know each other well, but we’ve
0:40:19 hung out a couple of times. I really, I really love spending time with you because I see us as
0:40:25 yin and yang. And I see us as, as actually trying to do the same thing. You have a bigger heart than
0:40:31 you give yourself credit. And you’re, you have a lot more warmth and kindness than you give yourself
0:40:36 credit. I’m probably better at the shit that I beat myself up about them, you know, than I
0:40:41 realize or that I give myself credit for. And you and I make each other uncomfortable because my
0:40:45 strengths are your weaknesses and your weakness, and your strengths are my weaknesses. And that’s
0:40:52 the discomfort, which is spending time with you just reminds me what I suck at. And I’m sort of
0:40:56 having a minor love affair with you and your work. Like when I see you pop up on my Instagram,
0:41:00 constantly, by the way, well done. To resist this futile. I’m AOL in the 90s.
0:41:06 Constantly. Whatever your algorithm, you nailed it. Like I, I actually had to mute you just for
0:41:14 a week just to have a breath. You know, your stuff is getting better. You’re clearer. And I just,
0:41:20 I sit quietly and go, fuck, that’s good. I love how we turn my interviews into me, but back to you.
0:41:25 Well, I’ll share something about me and I, I want, I want you to respond. You said something that was
0:41:29 really interesting. And that is you’re kind of a function of what’s tortured you. I grew up with
0:41:36 real economic anxiety. So it’s just a, it’s a ghost and a demon or, you know, a monkey on my
0:41:41 back. I just can’t shake. I’m always thinking about money. I’m very, very worried about being poor
0:41:47 again. And it’s hugely motivating, but also anxiety driven. And that is sort of my,
0:41:52 I don’t know if it’s my cross to bear, but it plays too big a role in my life.
0:41:57 What do you think it, it tortures you and where does it come from?
0:42:04 So what I know about the concept of why this, which is this thing, this deep seated inspiring
0:42:08 thing inside all of us, one of the things that I’ve learned about it is the thing you give to
0:42:11 the world, the thing you have, that gives you valuing in the world and to your friends and your
0:42:17 relationships is also the thing you need the most. And so it makes perfect sense to me in this balanced
0:42:22 equation of this thing you crave is this thing you fear, you know, that makes perfect sense to
0:42:28 me and that you grew up without means you’re afraid of having going back there. My torture is
0:42:37 I really, really bad ADHD in a time where it was never diagnosed. You know, I was just considered
0:42:43 a hyperactive. My parents, by modern standards, did a lot of the wrong things. I don’t fault them
0:42:50 for it. There was no, there was no, you know, they, they did the best they could with a hyperactive
0:42:55 kid who couldn’t focus and didn’t do schoolwork. I mean, what are you supposed to do? Do your
0:43:00 homework and I didn’t do it. And I’m like, I don’t, you know, and so, you know, I, I’m, I really
0:43:07 struggle to build structure and business is nothing more than structure. That’s what it is. And I
0:43:13 carry like when I talk to people who are brilliant operators and some of my, some CEO, entrepreneur
0:43:17 friends who just, I watch the structures that they’ve built. Now, are they operating, you know,
0:43:22 are they changing the world? Are they contributing to society? No. But my goodness, they built these
0:43:27 remarkable, and I get so insecure because for them it comes so easily. And for me, I really struggle
0:43:34 with it. And I’m to the point where I just stay quiet in those meetings when people like talk about
0:43:39 finance in front of me and they use all the financing jargon or an investment jargon and
0:43:43 they just assume I know it all because I’m at a point in my career where I guess others do.
0:43:49 I literally just have to go quiet out of sheer embarrassment. And so I carry a lot of discomfort
0:43:59 that I really don’t understand money. I don’t understand it. I’m not good at it. And any money
0:44:09 that I’ve made was an accident. And I see people who are contributing to society less work less
0:44:15 hard on the work that they do. And I see them make way more. And I’m not mad at that, but it
0:44:22 makes me feel like, come on, fucker, like up your game, you know. And I feel insecure in the worst
0:44:27 of times. And the best of times, I surround myself with people who are really good at it.
0:44:35 I ask advice, I’ve called you for things that are probably remedial, but to me, they’re advanced.
0:44:40 And just learn to get over the discomfort of asking for help
0:44:43 from people who I fear will judge me because they know so much more than I do.
0:44:48 Yeah, I think what you just described, though, having a lack of financial literacy,
0:44:58 I think you’re describing 97% of America. And I want to be clear. I’ve been wealthy three times.
0:45:02 And the reason why it’s been three times is because twice I lost it all because I was not
0:45:09 financially smart. I could have held on to my wealth. And instead, I was bought into this kind
0:45:16 of VC, fomented zeitgeist of go all in on something. And if you really, if you persevere and never
0:45:20 give up, I should have given up. I should have sold my stock or diversified. Instead, I was going
0:45:27 like 120% in on things. And then some things out of your control, some things in my control,
0:45:32 I just screwed up. But, you know, when the dot bomb implosion happened, I got broke again.
0:45:35 When the great financial recession came along, because I hadn’t been smarter and diversified,
0:45:40 I got broke again. And I think some of the, I hear some embarrassment or self-consciousness
0:45:45 in your voice, I think it’s especially prevalent among men, because they assume if you’re successful,
0:45:51 that you’re not really successful in America as a man, unless you’re financially extraordinarily
0:45:57 successful, and that you just accidentally wake up and get money, right? We’re supposed to be
0:46:01 you know, we’re supposed to wake up and accidentally have, you know, a five o’clock
0:46:06 shadow, a deep voice, a desire to procreate and be just really good at money. Otherwise,
0:46:10 we’re really not men. Do you think that in America, I wonder if one of the things that
0:46:17 creates loneliness among men is that we’re not, we’re so evaluated now, I think women are so
0:46:22 disproportionately evaluated on their aesthetics, but at the same time, men are so disproportionately
0:46:27 evaluated on their professional and financial viability. Do you think it creates more separation
0:46:30 and loneliness that men don’t have these kind of conversations or they feel embarrassed to have
0:46:36 these conversations? That’s such a good question, right? You know, sort of, as you talked about,
0:46:42 which is, you know, what are people posting on Instagram? All social media is marketing. And
0:46:46 if you’re not marketing, you’re not using it, right? Like, whether you’re marketing yourself or
0:46:50 something, it’s, that’s just what it is. All social media is marketing. And so, it’s fun to watch,
0:46:55 as you said, sort of how people market themselves. So, how women market themselves tends to skew
0:47:02 beauty, you know, and how men market themselves tends to skew wealth, you know, standing in front
0:47:08 of the Ferrari, the rented Ferrari. And I think you’re, I think you’re right. And just like we,
0:47:12 and there’s a, and to your point, there’s a lot of conversation about the dangers of social media
0:47:20 for women about creating unrealistic expectations of beauty, especially for young girls, and that
0:47:25 there’s no conversation about the unhealthiness of social media creating unhealthy expectations
0:47:30 for young men and boys. We don’t have that conversation at all. I think you’re 100% right.
0:47:38 And you and I have both talked about this, you know, the dangers of a lonely man, you know, you,
0:47:44 you know, show me, go to the Middle East with, you know, 25% unemployment in a shame-based society,
0:47:48 you’re a virgin and you’re living at home, you know, show me, show me somebody who’s committed
0:47:53 a mass homicide. And I’ll show you somebody that’s generally a lonely man.
0:48:00 Just as we wrap up here, I’ve had this whole wrap about if there’s one enduring skill that you’d
0:48:05 want to accrete to your children, it would be storytelling. That is the key to success across
0:48:10 almost every industry or real success. At the end of the day, you and I make a living storytelling.
0:48:15 And you’re, you’re outstanding at it. You know, I’m one of the, I don’t know,
0:48:19 30 million people that saw your kind of TED Talk that sort of, I don’t know if it made you famous,
0:48:23 but definitely took you to a new level without trying to be trying to be as
0:48:30 immodest as possible. What have you done? And what are your practices and hacks such that you can
0:48:36 maintain sort of your elite, you know, elite athlete status as a storyteller?
0:48:42 Thank you for that. Can I tell a story? I’ll be here all week, try the veal.
0:48:46 It was a former Undersecretary of Defense who was giving a speech at a large conference,
0:48:51 1,000 people, whatever. And while he’s giving his remarks, he takes a sip of from his coffee
0:48:56 that he’s holding in the Styrofoam cup and he smiles and he interrupts his own presentation.
0:49:01 And he says, you know, last year I spoke at this exact same conference, except last year I was
0:49:06 still the Undersecretary. And last year they flew me here business class. There was somebody waiting
0:49:10 for me at the airport to take me to the hotel. I got to the hotel. Somebody had already checked
0:49:13 me in. They just gave me my key. I came down in the morning. There was somebody waiting for me
0:49:18 in the lobby. They brought me to the same venue. They took me in the back entrance. They took me
0:49:23 into the green room and they handed me a cup of coffee and a beautiful ceramic cup. He says,
0:49:27 “I’m no longer the Undersecretary. I flew her coach. I took a taxi to the hotel. I checked
0:49:31 myself in. This morning I came down and took another taxi to the venue. I came through the front
0:49:36 entrance, found my way backstage. And when I asked somebody, “Do you have any coffee?” They pointed
0:49:41 to the coffee machine in the corner and I poured myself a cup of coffee in this year’s Styrofoam
0:49:46 cup. He says, “The lesson is the ceramic cup was never meant for me. I deserve a Styrofoam cup.”
0:49:54 I’ve tried to remember that. That it’s okay to enjoy the ceramic cups. It’s okay to
0:50:01 think about the ceramic cups. One ceramic cups. But at the end of the day, remember that it’s not
0:50:06 being given to me. It’s giving to the position I held in this moment. And when I move on,
0:50:11 they’ll just give it to the next person. It was never meant for me. And I think what that does
0:50:17 are two things. It reminds me where I come from, what I’m entitled to, and it also helps me live
0:50:23 in absolute gratitude. That anything that I get, all the ceramic cups I get to enjoy, I am grateful
0:50:29 for every one of them and think I deserve none of them. And so when you ask me sort of like what
0:50:36 helps me stay true as a storyteller, I think it’s very simple, which is I don’t view myself as an
0:50:41 expert. I view myself as a student. I generally think of myself as an idiot. I’m just more comfortable
0:50:49 with the idea of admitting it these days. And I really like learning. And so the stories I tell
0:50:54 are not actually for your benefit. The stories I tell are to help me make sense of the world.
0:51:00 And the stories I tell help me understand complex things. And if I’m going to explain something
0:51:04 to you, the best way I know how to do it is by telling the story that helped me understand it.
0:51:10 Last question. In five years, kind of first things that come to your mind,
0:51:16 if you’re sitting here in five years and the following one or two things that happened to you,
0:51:20 and that was success, what are those things? What boxes are you still looking to check?
0:51:31 I’m very sorry. I can’t answer the question. I’m living proof that having a plan means nothing.
0:51:37 My entire career was, I would never want to be a public speaker. I never wanted to write a single
0:51:43 book, let alone five. Like nothing I’ve done in my career was in the plan. My plan was thrown out
0:51:51 ages ago. I had one. It didn’t go that way. And so to me, the folly of a plan, it’s like
0:51:58 planning how many miles, it’s like planning which highway you’re going to take and how many miles
0:52:03 you want to drive per day, but not knowing the destination. It’s like figuring out these way
0:52:07 points. Like in three days, what city will you be at if you’re driving across countries? Like,
0:52:13 which direction am I going in? And my focus tends to be so far over the horizon to a
0:52:20 vision, an unrealizable idealistic vision, and the path that I take, I’m agnostic.
0:52:25 And so you’re asking me to tell you what the way point will be. I could tell you something,
0:52:33 and I can guarantee you it won’t happen. So I’m just trying to find the most efficient and fun path
0:52:39 to that crazy, far away place that I know I’ll never get to. And that’s
0:52:42 unnerving and more fun.
0:52:47 Wasn’t it Eisenhower that said plans are useless, but planning is invaluable?
0:52:56 And I think that’s true. I believe in backup plans. I believe in alternative routes. Like if
0:53:02 this one’s blocked, I’m going to go that direction for my career. I believe in going slowly in the
0:53:06 right direction versus speeding off in the wrong direction. So when companies talk about growth at
0:53:14 all costs, I’m like, for what reason? And I’m okay knowing that other people are driving faster
0:53:19 than me, because I know at some point they’ll hit a road. Not that I’m in competing against them.
0:53:23 I just know this from experience. When I was young in my career, I used to go to a guy.
0:53:29 He was very successful. He did similar things as me. He made a ton of money. I made none.
0:53:34 And he would say stupid shit like, I’m not getting out of bed for more than $25,000.
0:53:39 I won’t even get out of bed. And I was like, oh, shit, I do stuff for free all the time because
0:53:44 I really want to talk to somebody or meet somebody or sounds like fun. And he basically
0:53:49 spent most of the time I went to him for advice calling me stupid. Well, I can guarantee you’ve
0:53:55 never heard of him. And my career has faster passed him. And it’s not a competition and
0:54:02 there’s no gloating. For me, the lesson is I’d rather play the slow, steady game than the fast
0:54:08 game where I can show off to everybody. And understand how I think about my career. No
0:54:12 matter how much success I have, however you want to define it, I always think I’m still at the
0:54:17 tip of the iceberg because there’s so much more work to do. And I think focusing on what’s beneath
0:54:21 the ocean, I think keeps you humble and keeps you focused on all the work that has to be done.
0:54:25 But you’re asking me to tell you how much iceberg is going to be above the ocean and I couldn’t
0:54:30 tell you. Simon Sinek is an international speaker and bestselling author of the books,
0:54:37 Start With Why, The Infinite Game and Finder Why. He’s also the founder of The Optimism Company,
0:54:41 which provides programs for leadership development. He joins us from his home in Los
0:54:46 Angeles. Simon, I always enjoy spending time with you. We are so, you’re the most different person
0:54:51 I know that is the same person. And I think that’s what I enjoy so much about spending time with
0:54:57 you is we’re so similar from an exterior standpoint. And you just come at stuff from such a different
0:55:02 perspective as was me and it really illuminates. You just pointed something out to me that
0:55:07 it was sort of puncturing and that is sometimes I think when I’m advising people and I draw my own
0:55:12 experiences in, I think sometimes I’m boasting rather than just helping and I want to be more
0:55:18 cognizant of that. Anyways, brother, it’s always great to speak to you and congrats on everything.
0:55:24 Thanks. And I’m loving getting to know you. I really am. You know, you snuck up on me.
0:55:29 Go on. Like when I see your shit everywhere, legit, I smile like a proud parent. I’m like,
0:55:36 yeah, man, go, you know. And I just, I’m really, I can’t wait to come back to London and spend
0:55:38 more time with you, but properly. I appreciate that.
0:55:55 Out of happiness. I’ve been thinking a lot about grief. This was a rough weekend for me as I’m
0:56:03 sure it was for a lot of people. The news of the hostages being murdered by Hamas in Gaza, specifically
0:56:11 the story of a 23-year-old American Israeli Hirsch Goldberg, Pauline, who was wounded and
0:56:17 abducted by Hamas during the Nova Music Festival Massacre. He was held hostage for almost 11 months
0:56:23 until his body was recovered from Rafa in the Gaza Strip on the 31st of August, 2024. And I’ve
0:56:30 been thinking a lot about why that specific situation has inspired so much collective grieving,
0:56:38 given there’s spent so much death and destruction, both obviously among those killed on October 7th
0:56:43 and those taken hostage, but also so much grief and so much death and destruction
0:56:52 registered by people in Gaza. Why is this young man’s death so rattling? And I think it’s for a
0:57:01 few reasons. One, you can relate to it or they put a face on it. I saw the parents speak at the
0:57:08 Democratic National Convention and just seeing the grief, just so, just the just profound sadness and
0:57:15 anxiety on their parents’ faces. Any parent just looks at them and immediately kind of understands
0:57:20 or comes close to that horror and it puts a face on it. Whereas when we see news,
0:57:25 it just seems somewhat a little bit remote or distant, if you will. So I think it’s putting a
0:57:31 face on it. The story of parents obviously is very a gripping one. If you’re a parent, you just feel
0:57:42 such immense sadness. And I think what it does though, it informs your life. And that is what
0:57:46 you hoped for. And what I’ve tried to do last night, I was a real funk to try and get out of it,
0:57:53 was I thought, okay, the reason I have these fears, the reason I’m so worried about grieving is one,
0:57:57 anthropologically, it makes me a better father. It makes me think about protecting them. I’ve already
0:58:04 called my son today. It does make you a better, it does attach you to them. That fear of potentially
0:58:07 experiencing that grief, putting a face on it obviously from a current standpoint.
0:58:14 But also, as I think about this, it really is a function of the blessings you have. The
0:58:18 grief you feel is because you were put in a position where you were able to attach to others
0:58:22 and you were able to experience what is the most important thing in life and that is deep and
0:58:28 meaningful relationships. And some, I hope all of you listening out there, I would wish for all
0:58:33 of you a lot of joy and deep and meaningful relationships that don’t register grief, but
0:58:38 present the possibility of grief, which is nothing again, but receipts for love and means that you
0:58:44 have people in your life that you care a great deal about. This episode was produced by Caroline
0:58:48 Shagren. Jennifer Sanchez is our associate producer and Drew Burroughs is our technical
0:58:53 director. Thank you for listening to the PropG Pod from the Vox Media Podcast Network. We will
0:58:58 catch you on Saturday for No Mercy, No Malice as read by George Hahn. And please follow our
0:59:02 PropG Markets Pod. That’s right, the PropG Markets Pod, wherever you get your pods for the new
0:59:17 episodes every Monday and Thursday. Woohoo! Ka-ching! Mo money! Light up the rail. I want some Bolivian
0:59:23 marching powder. Where’s the, where’s the Dom Peragnon? I want some channel. I want for some bursace.
The Dawg is back!
Scott opens with what he’s been up to the past month and shares some exciting news from Prof G Media.
We’re then joined by Simon Sinek, an international speaker and best-selling author of the books “Start With Why,” “The Infinite Game,” and “Find Your Why.” Simon discusses all things leadership, mentorship, and the struggles men face in building meaningful relationships. We also get into Simon’s personal life, including his career journey, the demons he wrestles with, and his hacks for mastering the art of storytelling. @simonsinek.
Subscribe to No Mercy / No Malice
Buy “The Algebra of Wealth,” out now.
Follow the podcast across socials @profgpod:
Learn more about your ad choices. Visit podcastchoices.com/adchoices