Conversation with Simon Sinek — Finding Your Why, Feeling Stuck, and Building Strong Leaders

Simon Sinek, a renowned leadership expert, author, and motivational speaker, joins Scott to discuss his visionary concept of “Start With Why,” along with insights on building strong teams, leadership, feeling stuck, and finding your purpose. Simon also gets Scott to open up about a meaningful memory of his mom. Follow Simon on Twitter, @simonsinek. P. S. Scott is on holiday, so we’ll be back with our business analysis and Algebra of Happiness in September! Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:01Scott Galloway?

  Support for the show comes from Northwest Registered Agent. Your business identity is everything that makes your business legitimate and professional. With Northwest Registered Agent, you don't just form a business, you start a complete foundation built for privacy, credibility, and growth. That includes registered agent service, a business address, operating agreement, domain, website, professional email, phone number, and built-in privacy. In other words, your home address, personal email, and phone number stay private. Don't pay hundreds or thousands of dollars for what you can get from Northwest for free. Visit northwestregisteredagent.com/profgfree and start using free resources to build something amazing. Get more with Northwest Registered Agent at northwestregisteredagent.com/profgfree.

• 0:48Scott Galloway?

  Episode 263. 263 is the area code serving Montreal. In 1963, zip codes were introduced to improve mail delivery efficiency, and the first push-up bra called the Wonder Bra was introduced in Canada. My son asked me, "What is a Canadian?" And I responded, "It's an unarmed American with health insurance."

• 1:11Scott Galloway?

  Go, go, go!

• 1:20Scott Galloway?

  Welcome to the 263rd episode of the Prop G Pod. The dog is still on vacation in Nantucket, leaning into his white privilege. Didn't want to like Nantucket. Didn't want to like it. I think of myself as more of like a Euro trash guy. And went to Nantucket, and it's lovely. Sambar in the middle of the Atlantic. What will I be doing this trip to Nantucket? No joke. Some awful scientist decided to start capturing great whites, for some reason, off the coast of Cape Cod. And then tags them. And that's the worst part. And now there's an app you can download. And you can see where these refrigerators with teeth are roaming. So my kids dress up as seals, go surfing, and then their paranoid neurotic father sits on the shore staring at

• 2:04Scott Galloway?

  a phone, looking at how there's some monster about 700 meters to the southeast. Anyways, that's my vacation in Antucket. What are you doing this summer? In today's episode, we're sharing our interview with Simon Sinek, a renowned leadership expert, author, and motivational speaker. We discussed with Simon his visionary concept of start with why, along with insights on building strong teams, leadership, feeling stuck, and purpose. One of the wonderful things about the business I'm in is I get to travel and I get to speak at different events. And there's sort of this speaking circuit where we see the same people, we see each other all the time. Tony Hawk, I see all the time. By the way, the skateboarder, lovely guy, was, I think, one of the greatest skateboarders in history. And he's just a really

• 2:47Scott Galloway?

  like soulful, decent man. He's on the speaking circuit. People love him. I see Gary Vee all the time. I like Gary. I think he's interesting. The thing, when I see Gary speak, that I'm always impressed by, he doesn't use slides. He just talks about kind of business lessons you can draw from platforms and social media. Who else do I see a lot? I see Adam Grant a lot. Adam Grant is basically me, but more credible and a better academic. I see Adam everywhere. He's my nemesis. I will, I will best you, Professor Grant. By the way, because I'm a narcissist, I typed into ChatGPT the other day, who are the most influential academics in America? And I was ahead of Adam Grant. That made my day. I showed it to my sons, and my sons are like, what are you doing? Typing into ChatGPT questions about yourself. Anyways, not a great moment. Not a great moment.

• 3:32Scott Galloway?

  Learning from my children. They're teaching me values. Anyways, I ran into, or I run into a lot, Simon, who is an outstanding speaker and talks a lot about what is your why. This is, of course, another, yet another guest where we turn everything to me, and it ends up being therapy about Scott. But I think this is a good conversation. Simon is a very interesting, soulful guy. Oh, true story, another true story. I'm in London having lunch with Simon, and I see someone busting a move for us. And I think, oh, it's a fan. It's a fan of the dogs. And this happened three times and all three times people came over and looked Simon in the eye and basically looked as if they were about to start weeping and told him how much

• 4:14Scott Galloway?

  their work meant to him. Anyways, Simon Sinek has changed a lot of lives, means a lot to a lot of people. Please enjoy our conversation with Simon Sinek. Simon, where does this podcast find you?

• 4:25Speaker 01

  I am back in Los Angeles.

• 4:27Scott Galloway?

  Back in LA. So Simon and I have become sort of friendly. We saw each other at, where were we? Oh, Summit at Sea and then

• 4:35Speaker 01

  Summit at Sea, yeah.

• 4:36Scott Galloway?

  And then in London. And so if I seem exceptionally casual, it's because I've decided we're good, good friends. So Simon, first and foremost, you're wearing a short sleeve shirt and you're jacked. Are you on testosterone? What is your workout routine?

• 4:48Speaker 01

  Inconsistent.

• 4:50Scott Galloway?

  Inconsistent? I don't buy that. I know bodies. You work out. You work out, I would bet, two to three times a week and eat pretty well.

• 4:58Speaker 01

  You're very generous. I think I was blessed with broad shoulders, which makes it appear that I am in better shape than I am.

• 5:04Scott Galloway?

  So you're not a big workout guy?

• 5:06Speaker 01

  That's really nice. I work out. I go through phases where, like, like, like most people who have ADHD, everything in my life is in phases. I'm very into something and then I fall off the wagon, then I get back into it. So I'm sort of in the mid wagon stage.

• 5:22Scott Galloway?

  Mid wagon? Okay, so for those of you that don't know Simon, and most of you do, he's best known for popularizing the concept of why. In his first TED Talk, and I think it was 2009, it's become one of the most watched TED Talks of all time with 37 million views. By the way, I did a TED Talk and it got substantially fewer views. Anyways, Simon's books include Start With Why, Leaders Eat Last, Together Is Better, Find Your Why, and The Infinite Game. So can you break down this idea of why? What is your why? How do you discover your why? Just sort of riff on that for a minute.

• 5:57Speaker 01

  So the why is this deep-seated purpose, cause or belief that drives every one of us. It's based on the biology of human decision-making. So it's not something you, it's not up for debate. Think of it like gut decisions, right? You talk to the most successful people in the world. You say, what's your secret? They say, I always trusted my gut. Well, there is no part of your stomach that makes decisions. But it's a feeling and that feeling comes from the limbic brain, which is responsible for all of our feelings like trust and loyalty. But it's also responsible for all of our decision-making. We are not, as many people think, rational animals. The neocortex, our homo sapien brain, is responsible for rational and analytical thought, but actually is not responsible for decision-making.

• 6:41Speaker 01

  And so as much as we like to think that we're driven by rationality, we're not. And so to understand your why is to understand that deep-seated drive that every one of us has. And the thing that inspires us and drives us is different for everyone, which is why it's nice to know what your why is, because it can actually serve as a filter for decision-making and career decision-making and relationships and all that kind of stuff.

• 7:03Scott Galloway?

  How do you go about figuring out what your why is?

• 7:06Speaker 01

  So the why fundamentally is an origin story. It comes from our past. We are all the sum totals of how we were raised. You know, you are the way you are and I am the way I am because of the experiences that we had growing up as kids. And, you know, a why is fully formed probably by your mid to late teens. You are who you are. I am who I am. And the rest of our lives offer us opportunities to live in balance with who we actually are. It's how we're operating when we're at our natural best. So to discover one's why is basically to go backwards. It's to look at all of the times in our lives when we were our happiest or most inspired, the projects we worked on that we loved, things like that.

• 7:49Speaker 01

  And what you very quickly discover are patterns. And if you can link those patterns together, you can articulate your why and your hows, which are sort of your natural strengths or the environments in which you operate best.

• 8:02Scott Galloway?

  It sounds like you might be a fan of Nietzsche, who said, think of the moments where you were happiest and most rewarded, what was common about those moments, and then try and run a line through it and extend it around what you're going to do in the future. Am I making that up?

• 8:15Speaker 01

  No, that's exactly how a Y works. And that's exactly the process, which is to go backwards and find those moments. And even when I go back and ask people about their childhood, and sometimes they say, well, I didn't have a very happy childhood. It doesn't matter, because even in difficulty, you always find these amazing stories that come out. So one example, I was doing a Y discovery for a woman who grew up in a very abusive household, alcoholic father. And when her dad would go on a rampage, she would hide in the closet with her brother. And she's telling me the story of trauma, but she would always cover her brother. She would hold him and put her back to the closet door to protect him.

• 8:58Speaker 01

  And you realize that throughout her life and throughout her career, she's always been a protector. And where she finds joy is in offering others safety. And it was core to her, to who she is. And it was ultimately a very positive outcome.

• 9:12Scott Galloway?

  That's nice. You talk a lot about leadership. In one of your YouTube videos, you said that you think leadership is one of the most misunderstood subjects in business. What did you mean by that?

• 9:23Speaker 01

  So I think people think being the leader means being in charge, that you're number one, that you're, you know, you have to make all the decisions. And that's just not true. Leadership is the awesome responsibility to see those around us rise. It's not about being in charge, it's about taking care of those in our charge. And it's a skill, it's a learnable, practicable skill. Many people find themselves in a leadership position because they either started the company, so they just happen to be the leader, or that they were really good at doing something, so they kept getting promoted, to the point where they're now responsible for people who do the job they used to do. And we don't get taught how to lead.

• 10:04Speaker 01

  So, you know, good leadership is actually harder to come by. If you're lucky enough to have had a good leader in your life that you could model yourself after, that's an education. But like, somebody who's great at sales, for example, will get promoted to sales manager. But being a sales manager and being a salesperson are not the same skill set.

• 10:24Scott Galloway?

  What are some examples? If you're a manager and you're interested in demonstrating leadership, what are some practical examples of that?

• 10:31Speaker 01

  Number one is, is, is, I think honesty. You know, I've, I, I, there's a, there's a leader I know who got promoted into position where he actually knew a lot less about the subject matter, put to lead a team that was in a category that he didn't know about. And instead of coming in and sort of like pissing on all the lampposts and making his mark, he walked in on his first day and said, look, I, I know a lot less about this than you do. I'm going to try and stay out of your way and, and let you do the job, teach me. And my job is to provide resources, give you top cover, learn a tremendous amount, but I'm, I'm here to tell you that you know more than I do, which is incredibly empowering for a team.

• 11:13Speaker 01

  As opposed to, I think, what a lot of leaders do, especially people in new leadership positions, which is they try to prove that they're worthy of the position to try and prove to their bosses that they made the right decision. And they sometimes speak too much, they make too many choices too quickly, too many decisions too quickly. You know, the company Chanel, they have a wonderful practice when they hire senior leaders, which is if you're hired as a senior leader, you're not allowed to speak in meetings for the first 90 days of your employment. And their, their attitude is, we know you're smart, we hired you, you don't have to prove it to us, and we would prefer that you shut up and learn. And the reason we say 90 days is because we expect you to have a long career here. So for you not to make decisions for the first three months of your employment, we're

• 11:58Speaker 01

  okay with that. And, and I just love that. By, by institutionalizing it, it takes the pressure off the person to feel like they have to speak up in every meeting to prove their value.

• 12:07Scott Galloway?

  Isn't that more broadly great advice around relationships as well as leadership? That I find with, with parenting, with relationships, so much of the time, the best response is just to listen.

• 12:21Speaker 01

  I, I mean, asked and answered, right? Like, this is where, for some reason, we've bifurcated our lives into like personalized and professionalized, but at the end of the day, we're managing relationships in different places. I mean, it's all human beings interacting with human beings. You know, we, we want to be able to make other people feel seen and heard and understood. And when they do, they're all in and will give us, give their best, both to the relationship or to, to the company.

• 12:46Scott Galloway?

  You've become sort of the go-to, or I don't know, the bridge between corporate leadership and Gen Z and millennials or the workforce. What, how would you distinguish or differentiate that generation as it relates to their values, how they approach work? And what advice do you have for corporations that want to be thoughtful, but also, you know, optimized for this new workforce?

• 13:14Speaker 01

  So I think there's something that we have to acknowledge that's completely different about this generation that, as far as I know, no previous generation has ever had. Which is when you and I started our careers and we and I graduated college, we showed up at our, our jobs on day one and legitimately, we were idiots. Like, we didn't know a thing. And so we had to defer to those who'd been working at the company longer so that we could learn. And, and that's sort of how we acted and that's how we were treated.

• 13:50Speaker 01

  Where this younger generation that's coming up in a computerized, interneted world, they actually start day one of work with a skillset that those in, who've been working longer either had to learn or don't have at all. So they actually start day one with skills. And it does, it has, it's sort of, it's a blessing and a curse, right? Like, like everything. The blessing is, wow, you start day one with a skillset that we need and don't have. Amazing. The downside is because they have a skillset that other people don't have, it gives a false sense of, I know a lot.

• 14:30Speaker 01

  But there's still a lack of experience and there's still a need to, to learn, obviously. It's just day one, you're just a freshman. And both are right and both are wrong kind of thing, you know? And I think that's part of the push me, pull you. So I think older generations, I've seen people in leadership do, do two things which are wrong, which is offer too much deference to the younger generation because they bring that skillset that they don't have or understand. Or no deference because they treat them as if they were idiots like they were on their first day of the job. And the answer is something in between. But I think that's, that's a fascinating and modern dynamic that the previous generations just didn't have.

• 15:09Scott Galloway?

  There's sort of a, they've developed a reputation fairly or unfairly for being a bit entitled. Do you agree with that?

• 15:16Speaker 01

  Yes, entitlement is a word that, you know, there are many words that are used to describe young generations that have been used for generations. But entitled is one that seems to have shown up relatively recently, you know, the past 20 or 20 years or so. And, you know, if you've worked with some people from the young generation, it certainly feels that way. I mean, these stories have become boring that they're so often used, you know, been working for four months at a company or eight months at a company and want, you know, double, double salary. And I love the, the appearance of confidence that goes with it, but, but it backfires.

• 16:00Speaker 01

  And I try and tell young people, it's not that you, it's not that you think you're worth more and it's okay to advocate for yourself, but how you advocate for yourself makes a difference. So, for example, coming in to your boss's office and say, I'd like 140% raise please because I think I'm worth it, is a very hard negotiation. That's not, that's not going to go well. You've given the other person no room. But rather to come in and say, hey, I've been working hard. I really like it here. I see myself staying here for a long time and I would like to get on a path to, to increase what I'm making. Can we discuss the best way for me to do that? And that's a discussion and a negotiation.

• 16:41Speaker 01

  And I think it, it allows the person in leadership to feel included in, in your professional growth, just like you want to feel included in your professional growth. It's not about the factual outcome. It's about making somebody else feel included in the process. And I think that's what good career management is as well, both up and down a chain of command.

• 17:02Speaker 02

  We'll be right back.

• 17:06Speaker 02

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• 17:35Scott Galloway?

  Here's another benefit of Built membership. You also get access to what they call a neighborhood concierge. You can make restaurant reservations, book fitness classes and find new local spots, all while rewarding you and more than 45,000 merchant partners. It's simple. Being a renter and now owning a home feels a lot better with Built. You can download the Built app and join the membership for where you live at joinbuilt.com/prog. That's J O I N B I L T dot com slash prop G. Use our link so they know we sent you.

• 18:07Scott Galloway?

  So there's so few jobs or people I look at and I think I'd like to be that person and have that job. I know a lot of people in Hollywood and people think they want to be an actor or director. It's a shitty insecure industry is what I have found. I look at athletes and I think I'd never want a job that I got worse at as I got older. And these guys, they hit literally their late twenties, early thirties. They've become really bad at their job. And then most of them go through a pretty severe identity crisis around what do I do now that I'm no longer one of the top 10 footballers in the world? You're an exception. I look at what you do and I mean this sincerely. I think that what Simon has developed is super cool. You seem to be very passionate about what you're doing. You're relevant. Just a quick story.

• 18:50Scott Galloway?

  We were having lunch in London at Granger's, my favorite place, which is lovely. It's lovely. And this guy immediately caught eye contact with us, started walking over and I like stood up like, here comes a fan. I'm like, I'm so excited. He's like, oh my God, your work has meant so much to me. And he shook your hand. And I think it happened two or three times while we were at lunch. Zero for Scott and three times for Simon. You really, you're having a lot of impact, a lot of relevance. I know you make a very good living. I have trouble figuring out how you got to here because what you do is really unusual. Can you give us the Cliff Notes on from when you were at the ad agency to how you got to this point?

• 19:36Speaker 01

  So my ad career went well. You know, I learned from my dad, who I watched in business. You know, I remember he was an executive for a company. I would, you know, when I was a kid, I would go to work with him. You know, if I, if I had a day off school. And, you know, he treated everybody the same. And I, years and years and years later, I was giving a talk at a big company. And one of the executives came up to me and said, you know, you don't know this, but a million years ago, I used to work in the studio that the, you know, where your dad was an executive. And he says, we always remember that your dad was the only person that came down and talked to us. None of the other executives did. It made me really proud, you know, to hear that. But my dad imparted that unto me and my sister, which is you treat everybody like an executive.

• 20:18Speaker 01

  And so that was, that, that served me very well throughout my career. You know, I used to, you know, treat the mailroom guys in my ad agency the same as I treated everybody else. And the result was, when push came to shove, those guys helped me out. You know, those guys had my back. And I, and I saw it happen, like the, the young account executive who wanted to prove that he was tough would, you know, be abusive. And, and they didn't help him out, you know? I, I saw it happen in front of me, you know? They were just like, sorry, you missed FedEx, you know? And with me, they'd be like, don't worry, Simon, we got you. So my career in advertising went well. And there was an, I knew, I always knew that one day I wanted to start my own business. I used to say it in interviews, you know, this, I'm like, what do you want? I was an entry level.

• 21:03Speaker 01

  They're like, well, one day I want to start my own business and they would hire me. I always thought that was funny that you're hiring a kid who literally told you in the interview that I plan on leaving at some point. But that's what happened. There was an opportunity and I quit my job and I went and started my own business, thinking that I had a better mousetrap. It was also after September 11th, so I had a higher sense of cause as well. I think that September 11th did that to a lot of us. You know, I watched the buildings fall down from my office and thought, my God, my job is stupid, you know? And it was, it was difficult. I had a business partner who worked, it worked for a couple of years and then the relationship collapsed. I, I bought him out.

• 21:40Speaker 03

  What was the business on it?

• 21:41Speaker 01

  It was a marketing consultancy, Variations on a Theme. And, you know, after I bought him out, it was very hard for me to build the business by myself. We had great clients and we did great work, but I, I struggled to build the structure and I struggled to, I thought I had to make every decision and be in every meeting. I, I had that false belief of how leadership works. And life got really difficult. And I went through, I think what can only be described as depression. And thank goodness, a friend of mine sort of had an intervention because I was really good at lying, hiding and faking. I was really good at pretending that everything was fine. And a friend of mine came to me and said, something is very wrong. And I came clean. And all of the energy that went into pretending that I was happier,

• 22:26Speaker 01

  more successful and more in control than I really felt, went into finding a solution. And the solution that I found was this thing called the why. And I really, I discovered that my why was to inspire people to do the things that inspire them. And I had a choice to make. Once I figured out this, it wasn't so much that I figured out my why. It's like, I also figured out how to help other people find theirs. And I was doing it with my friends and I was doing it for my friends' friends for a hundred bucks on the side. And people would invite me to talk to their friends in their living room, which is how my speaking career started, you know, just talking people's living rooms. And the first decision I had to make was, do I put a TM on this thing called the why, called the golden circle, and try and leverage it and monetize it as much as possible? And it was my first test of why, right? Because my why was to inspire people to do the things that inspire them.

• 23:11Speaker 01

  And I realized, no, I can't do that. And so if you go back and look, like, there's no TM on the why or the golden circle on purpose. Because if I put a TM on it, I'm the only person who can do it. And there's no scale. And I wanted people to to spread the idea. I wanted people to steal the idea. I wanted people to use the idea. So I think that's a large part of it. I guess the way I would describe the way I've managed my career is like an iceberg, which is when I was starting out and, you know, I was talking about what I imagined, you know, it's like a tiny little bit of tiny little bit of iceberg sticking above the ocean and only a few people can see what you believe. And those are your first clients. Those are your first, you know, employees, the people who like, they see something in you that nobody else sees. And as you have

• 23:55Speaker 01

  a little bit of success, a little more iceberg pops up. And people can say, oh, it's amazing what you're doing. And I would always say, tip of the iceberg, because I saw all the work that had to be done that was beneath the ocean. And that metaphor has stuck with me my whole career, where no matter what I've achieved, and no matter what I've put out into the world, I'm actually not focused on what's above the ocean, which is all the tangible stuff that everybody else sees. I'm more focused on all the work that still has to be done. I think that's a large part of it, you know, which is I, I try not to live on the successes of the past. The future is way more interesting to me.

• 24:30Scott Galloway?

  So let's go back to your small business that wasn't working out, and then the intervention by the friend. And I think it's important to, I want to double click on that, because people romanticize entrepreneurship. We actually have very similar backgrounds. I started a brand strategy consultancy called Profit about the same time. And what they don't see is that the majority of businesses don't work out. And it's soul crushing, because it's, it's, if you don't have kids, it's the closest thing you have to kids. You conceive it, it looks, smells and feels like you. And the failure is very public. And it's just, it rattles you to your core when it doesn't work out. And sometimes you borrowed money from friends and family, and you've convinced these good people to come to work with you who buy into you and your vision, and you just feel like you're letting everybody

• 25:14Scott Galloway?

  down. When you're at that moment, or when you were at that moment, and you had this friend conducting intervention, you decided to do something different. In terms of your own emotions, and managing your own disappointment, and what you refer to as, it sounds like mild depression. What advice would you give other people who are struggling about a business? It's not working out, like just in terms of their own mental wellness? What did you learn helps to get you kind of unstuck? I have a lot of friends, super successful in their first venture. Their second venture, just through sheer odds almost, doesn't work and they get stuck. They just can't, they can't get off the mat, if you will. What, what helped you get unstuck from a moment where you could have entered a, an actual downward spiral?

• 25:57Speaker 01

  There are two things, one that I learned in hindsight and one that I learned the hard way. The first is, um, learning to say, I don't know, or I need help. You know, I think when you're, when you, when you start the business, you know, we get really good at having an answer for every question. You know, you, you learn this in a sales pitch, you know, everything the client says, you got an answer. And saying, I don't know, is, you know, we perceive as death or weakness, which is just not true. You know, part of lying, hiding and faking was that I knew every answer and I knew what, what, what was happening. And if somebody said you're, you know, you haven't won a client in four months, I'd be like, I'd talk about some strategic nonsense bullshit, you know?

• 26:40Speaker 01

  And I think to say, um, I don't know, or I'm struggling, or I need help and ask a friend or ask somebody and tell somebody. It turns out we're surrounded by people who love us and want to help us. They just didn't think we needed the help because we had all the answers and we didn't ask. Or, or worse, we pushed them away when they offered. And so, um, I was forced to accept help because A, my friend intervened and B, I, I was at least prescient enough to realize that if I didn't accept it, I probably would have gone out of business.

• 27:14Scott Galloway?

  So let's talk about Cynic, Inc., you as a business. I think a lot of people look at what you do and think, I'd like to do that. And obviously it takes a long time. What is the business and how do you break it down? Is it, do you get the majority of revenue from speaking, from books, from media? And by the way, I'm happy to talk about, I talk very transparently about how we make money. But I think a lot of people look at you and are fascinated, but think, what is that business? How does he actually pay his rent?

• 27:41Speaker 01

  So yes, speaking does contribute a lot. You know, the business that I'm building with my two partners with Hen and Sarah, the optimism company, is also growing, which I'm very proud of. And what is that, Simon? Optimism company is the company devoted to selling human skills. It's online learning all for human skills. You know, MasterClass can teach you tennis and how to direct a film. And we're like sort of MasterClass, but just for human skills, super focused. But I, you know, I'm, I make a lot less money than people think I make. I mean, I'm doing fine. I'm not complaining. But you know, if you compare me to you or to any of the folks in our category,

• 28:23Speaker 01

  I'm probably the smallest earner of all of us. And the real, the reason is, is I'm, it's never been a driver for me. The money has always been, quite frankly, accidental. It's the accidental byproduct of pursuing something larger than myself. And I'll give myself one compliment, you know, which is I was okay with setting goals that I knew that I would struggle to measure in any kind of short time. So for example, people set annual financial goals and they work very hard to make them and they feel like they succeeded if they hit them and they feel like they failed when they missed them, which to me is funny.

• 29:08Speaker 01

  You know, I think of building my business more like trying to get into shape. Like I have to exercise, I have to eat right, I have to do all these things that are very hard to do all the time. You know, they go in and out, like you have to be good at sales, you have to be good at marketing, you have to be good at leadership, you have to have good product development, you have to good, you know, you can't do all those things perfectly all the time. You just have to accept that. It's a constant, constant, constant striving, just like being healthy, sleeping, exercising, relationships, it's constant striving. So number one is that, that I'll never be perfect at it, I'll just have to keep working on everything and there's always a ball being dropped. Okay, I'm cool with that. And number two is I don't know how long it takes to get into shape. Like, I know that if I work out every day, 100% it's gonna work. I just don't know when, and neither does any doctor.

• 29:52Speaker 01

  And I accepted that for my career. Like, once I realized starting with Y was a thing, once I realized the law of diffusion was a thing, I was dogged about it and practiced it, and I knew it would work. I just didn't know when, and I was OK with that. One of the reasons every business doesn't follow these ideas is very simple, which is, I cannot tell you with certainty that they will work in the arbitrary timeframes you've picked to hit your goals. Momentum and trending mattered more to me than arbitrary numbers. I just wanted to see that it was growing. I didn't actually have any numbers to hit. I've learned not to compare my success to others, and I've learned to try to outdo myself rather than other people.

• 30:35Speaker 01

  And I think that that focus on what's beneath the ocean, on that iceberg, and not worrying about everybody else, and being OK with the fact that as long as I have momentum, it doesn't matter if I had any absolutes, any arbitrary numbers, is the thing. And it's, you know, I don't want to die with the biggest bank account. That's not my ambition. My ambition is to leave this world in better shape than I found it. You know, I think that folks like Jack Welch and Milton Friedman and the adherence to their philosophies have done tremendous damage to capitalism.

• 31:15Speaker 01

  And in so doing damage to capitalism, have done damage to our economy and our lives. You know, the fact that mass layoffs on an annualized basis to manage the books is a thing is because of the adherence to their philosophies. Prior to the 1980s, using mass layoffs to balance the books just didn't exist in the United States. And the capitalism that made America great, the capitalism that contributed to the wealth of a nation, the capitalism that created a huge middle class and let them enjoy the spoils of the nation by investing in the stock market, that's not the capitalism we have now. And so I want to undo everything Jack Welch did, and I can't do it alone. And I want to lie on my deathbed, regardless of what's in my bank account, and say, yeah, I had something to do with that.

• 32:00Scott Galloway?

  So we share the same publisher. And, and I had dinner with her a few weeks ago and she said that Scott, the only person that you're, that you're closest to in terms of what you've built and how you approach business is Simon Sinek. And I said that you and I had actually become friendly and had spent some time together. But, and I'm not proud of this. I, I don't have the nobility you have. My, my first priority for the majority of my life has been economic security, which is a more palatable way of saying I wanted to make a lot of money. And I'm trying to figure out what the fork in the road is because we're, we're actually pretty similar. Our career path, the way we make a living. I think a lot of fundamentally the goals we have are just very, very similar.

• 32:43Scott Galloway?

  Books, podcasts, you know, starting in marketing. We, we run into each other on the speaking circuit. We literally like bump into each other, leaving or getting on the stage. And I'm trying to figure out what went right with you or what went wrong with me. And so I'll ask a few questions. Did you grow up with money?

• 33:03Speaker 01

  We grew up upper middle class. So, so we never went without. It wasn't luxurious, but we never went without. But I think more importantly is my parents instilled in us the value of money. We didn't have easy come, easy go. Like if you wanted something, there were things that were too expensive for your birthday. You just couldn't have them. So put that fantasy aside. If there were things that we wanted that were considered unreasonable, we were expected to save up half and then my parents would match it. And if you broke something, then that's it. It's broken. It wasn't just immediately replaced. And we were taught to look after the things that we had. So I'm, we, we were taught the value of money. And, and we also, you know, I lived a different life than most because my dad was an expat. And so we grew up, I lived on four continents by the age of 10 years old,

• 33:48Speaker 01

  which is pretty dynamic. Let me, let me ask you a question if I may. Can you tell me a job that you had, a project that you worked on, something throughout your career, it doesn't matter when, it doesn't even matter if it was commercially successful, that you absolutely loved being a part of? Like inspiration flowed? And if everything that you did for the rest of your life was like this one thing, you'd be the happiest person alive?

• 34:14Scott Galloway?

  When I write about my emotions and I write fearlessly and sometimes unfortunately that involves alcohol, it's really strange. When I think probably the best posts I've ever written, and this is a symptom of an alcoholic, I've written at two in the morning and I've had a couple of drinks and I write fearlessly about my relationship with my mother or how I feel about my sons or what I, you know, the relation, the emotions I felt when I lost my dog, the troubled relationship I have with my father. That stuff resonates. I'm still, I'm addicted to other people's affirmation, but it evokes such an emotionally powerful response from people. And there's something about the written word. I don't

• 34:58Scott Galloway?

  know if you feel this way. It's like I've done big talks, so have you. I've done, you know, I've kind of had podcasts and clips on TikTok of our all that shit. When I write something that moves people and I hear from them, I think this is why I'm here. And that-

• 35:14Speaker 01

  Is there something, is there some, is there something specific that, that stands out? Like of all those, all that writing you did, is there one that stands out like this? This is the one that if everything was like this one, game over. I'm, I'm, I'm the happiest person alive.

• 35:27Scott Galloway?

  Well, for the most professional, I mean, I'm going to be clear, like making a lot of money and having economic security and being able to make a lot of money, spend a lot of money, give a lot of money away. It sounds crass. It's hugely rewarding for me. Hugely rewarding. And, and I had no money most of my life. And so that is really important to me. And having kids, it really weighs on me, my economic kind of obligation to them. But the, the, the actual work that has been most rewarding for me, and I'm going to put the question back to you in terms of specifics. I wrote about moving in with my mother who was dying and tips for people who are taking care of a dying parent. I wrote about the passing of my dog and how it was a marker for, the reason I was grieving so much about

• 36:11Scott Galloway?

  it was a marker for the fact I wouldn't have kids at that young age any longer. So those types of posts where I can be fearless. And I try to write as if no one's going to read it, but my sons and my objective is I want my sons to understand me because I'm a fairly intense, sometimes angry person and I, I, I don't make as much light in the house as I'd like. And so I want them to understand some of that's, some of those things about me. Those are the moments I feel most- I feel most rewarded in the context of doing something professionally. And quite frankly, it's the stuff that resonates with people. I can talk about disruption or technology and I'm, I'm good at what I do. I have good business insights, but the stuff that really moves people is when you're fearless about your emotions.

• 36:53Scott Galloway?

  The reality is the opportunity, just from a marketing standpoint that I've discovered, is for a straight white dude to talk about his emotions. Very few of us do in a very open way, but that's where I'm at. That's when I think, okay, I'm, I'm here for a reason. I'm doing what I'm supposed to do. So I'll turn it back to you. What, what are the specific?

• 37:10Speaker 01

  One more question. Tell me an early, specific, something I can relive with you. A happy childhood memory, not like we went to my grandparents every weekend. Something specific that I can relive with you. Early, specific, happy childhood memory.

• 37:23Scott Galloway?

  Oh, I remember like my dad got me into fitness, running on the beach with my dad. That was kind of the only thing we shared. He wasn't a very emotive, you know, didn't express a lot of emotion.

• 37:33Speaker 01

  You did that a few times. Is there, is there something that stands out? Like one particular, specific experience of any sorts?

• 37:40Scott Galloway?

  Yeah, so the thing that stands out, and it wasn't a childhood memory, but when my mom was first diagnosed with cancer and she was at my graduation and I was the commencement speaker and I looked up and I saw my mom waving her arms.

• 37:53Speaker 01

  So of all the amazing things that happened in your childhood, what's, what's about that one that stands out? Why do you want to talk about that one right now?

• 38:03Scott Galloway?

  Well, just saying someone, you grew up with two parents, right?

• 38:07Speaker 01

  Yeah.

• 38:09Scott Galloway?

  My mom was literally it for me.

• 38:13Scott Galloway?

  And to see just like this, this unbridled joy and pride.

• 38:25Scott Galloway?

  Couldn't contain herself was waving her arms.

• 38:30Scott Galloway?

  That'll be with me, that's my life.

• 38:34Speaker 01

  Thank you for sharing that.

• 38:37Speaker 01

  That story is very, very similar to the professional things that give you the intense joy.

• 38:46Speaker 01

  Where, I mean, I'm gonna cry now too. Like, I mean, your purpose, Scott, I mean, is clear. You are become your mother, which is for all of your very open struggles. And in your mother's case, it was extreme. It was cancer. In your case, it's, it's, you know, being a curmudgeon or being maybe an unhealthy relationship with alcohol. You know, like you talk about these things very openly and well, let's just chalk it all up to struggle. That in those moments, the times that you find great joy is to put your struggle aside and be in the audience and cheer others on and tell them, you know, be there to support them. And like when you write the posts about moving in with your dying mother,

• 39:31Speaker 01

  or you write the posts about how to deal with your dog that's dying. What you're, what you're doing, you're celebrating other people. What you're doing is, is, is taking everything that you have and using it for others. Like putting your struggles aside. And I, I think you are become your mother. Like you will find great joy when, when somebody else has, is struggling with something or achieving something and you will be there waving no matter what you're going through. And that's even what you said, what you wanted to do for your kids, you know?

• 40:04Speaker 01

  I will also say that the thing that you give to the world is also the thing that you need the most. And you talk about your unhealthy need for affirmation, public affirmation. It's because you really need your mom in the audience waving you on and just cheering you on, just to remind you that you're, you're doing good. But it doesn't stop there. It's so that you have the energy to do it for others.

• 40:27Scott Galloway?

  So as usual, I've masterfully turned this to me. I want you to share, Simon, what, what, what business activity or moments professionally have been most meaningful for you?

• 40:40Speaker 01

  I, I am inspired when other people come alive. And so the, the,

• 40:49Speaker 01

  The thoughts that are popping into my head are,

• 40:54Speaker 01

  when I was writing Leaders Eat Last, it was the most difficult thing I've ever done in my life. It was such a complicated subject. Every single chapter could have been its own book. And you know, Start With Why was like something like 68,000 words, something like that, where I sat down to write Leaders Eat Last and I wrote 150,000 words and was just getting started. And it just was endless and I couldn't organize all that information. It was impossible to organize. And I realized like sort of at the beginning of the project, I couldn't understand why all these social scientists and biologists that I was interviewing, why none of them had written this book yet? Why none of them had simply taken the biology of human decision making and the chemicals that control our emotions and overlaid it on corporate culture? It's because it was impossible to organize.

• 41:38Speaker 01

  And it, it, it beat me. Like I couldn't figure that book out. And so I decided to quit. And I remember walking away from my desk about eight or nine o'clock at night and I went for a walk on the streets of New York at night, literally to go through the checklist of quitting. And I knew I had to call the publisher and say, I can't do this book, which means I have to give my advance back because I'm in breach of contract. So, okay, check, I'll have that conversation. I knew that I would have to tell all the people who've been helping me and supporting me and helping with research that I wouldn't be able to do it. I knew I had to have to announce publicly, this book that I'd been touting would not be coming. So I'd suffer public humiliation, but I would get over it and so would they.

• 42:23Speaker 01

  You know, and sort of rationalize that it was fine. Like, you know, 10,000 books come out per year. Nobody's going to miss this one. You know, I just went through the rationalizing that it was okay to quit. And literally was going through the checklist of quitting and preparing myself for it. And I'm not sure the reason why, but I called a friend of mine, who at the time was in the Air Force Special Forces. And I called him and he picked up the phone and I don't even think I said hello. I think I just asked a question. I said, what do you do when you can't complete the mission? And as is his nature, he started telling a story. He's, he told a story, he used to be a helicopter pilot. And he told a story about a mission in Afghanistan where all of the intelligence

• 43:05Speaker 01

  showed that the air defenses were so great that it was an absolute suicide mission. And it wasn't like a kill Hitler mission where we're going to kill Hitler, but we're all going to die. This was like, we're all going to die and the mission will fail. Like, we're not even going to be able to get there. And so it's actually just a complete suicide mission for no value whatsoever. And they're preparing their helicopter for this mission. And his, his wingman turns to him and says, what do we do? Like, we've got wives, we've got kids, like, what do we do? Do we refuse to go? Like, what do we do? And my friend said to his partner, this is what we signed up for. We go. And, um, obviously the mission was scrapped, cooler heads prevailed.

• 43:50Speaker 01

  And then my friend said to me, you know, is this book more or less powerful than Start With Why? And I said to him, so far the research has been profound in my life and had a greater impact on me than Start With Why? He said, okay, funny story then. He said, before I met you, I was disillusioned with the air force and I wanted to quit. And I read this kooky little book called Start With Why, and it completely re-inspired me and invigorated me. And I stayed in the air force and I've never been happier. So if you're telling me that this book is more powerful than the first one, he says, you have to write this book. You have no choice. He says, this is what you signed up for, you have no choice. Now, he wasn't just telling me you have to do it because you have a contract. What he was saying was, this is what you signed up for, you have no choice, and I will go with you.

• 44:32Speaker 01

  Just like he said to his wingman, this is what we signed up for and we go. And so I turned around and went back to my desk and finished writing that book and figured it out. And I did so because I didn't feel alone anymore. And I felt like the mission was more important than me. That has been a recurring theme, the things that can make me cry, you know, whether my own experiences or if I see, you know, videos on social media are the ones where the chips are down. And somebody comes together in partnership to help somebody overcome something and to make them feel not alone and struggle. That has been, that has been powerful for me. And that really stands out. And, and if I can be that person for other people,

• 45:17Speaker 01

  I would be the happiest person alive.

• 45:19Scott Galloway?

  Simon Sinek is a bestselling author and an international speaker through his popular TED Talk on the concept of why. Simon has become a leading voice in transforming company culture and creating a better working world. As a trained ethnographer, he has discovered remarkable patterns in how great leaders and organizations think, act and communicate. He joins us from the City of Angels. Simon, I enjoyed this so much and I think you're so good at what you do. You are literally, you know, I'll kind of finish where I started. You're one of the few people I look at and think, yeah, I'd like to be him. So thanks for, thanks for your time today.

• 45:53Speaker 01

  Scott, it's a, it's a pleasure and you know, the feeling's mutual. You're, you're so good at the things that I'm bad at. That I, I, I really would love to learn from you. And I really look forward to seeing you when you are in town.

• 46:08Scott Galloway?

  All right, brother. Thanks again.

• 46:09Speaker 01

  Thanks, man. I really appreciate it.

• 46:15Scott Galloway?

  This episode was produced by Caroline Shaver. Jennifer Sanchez is our associate producer and Drew Burrows is our technical director. Thank you for listening to the Prop G Pod from the Vox Media Podcast Network. We will catch you on Saturday for No Mercy, No Malice, as read by George Hahn, and on Monday with our weekly market show.

• 46:42Speaker 01

  So I, very simply, I imagine a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do.

• 46:53Scott Galloway?

  So edible.

• 46:53Speaker 01

  It's not the world we live in.

• 46:56Scott Galloway?

  Sorry, God knows us. Keep going. Vision of the world, inspired every morning. Go ahead.

• 47:00Speaker 03

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