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

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1:04Go, go, go!

1:13Welcome 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. Sandbar 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.

1:50So my kids dress up as seals, go surfing, and then their paranoid neurotic father sits on the shore staring at a phone, looking at how there's some monster about 700 meters to the southeast. Anyways, that's my vacation in Nantucket. 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 discuss 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.

2:25And And there's sort of this speaking circuit where we see the same people or 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 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? I see Adam Grant a lot.

2:59Adam Grant is basically me, but more credible and a better academic. I see Adam everywhere. He's my nemesis. I was 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. My sons are like, what are you doing? and typing into chat GPT questions about yourself. Anyways, not a great moment, not a great moment. 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.

3:36This is, of course, 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 their work meant to him. Anyways, Simon Sinek has changed a lot of lives, means a lot to a lot of people.

4:12Please enjoy our conversation with Simon Sinek. Simon, where does this podcast find you? I am back in Los Angeles. 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 - Summit at Sea, yeah. 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? Inconsistent. 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.

4:51You're very generous. I think I was blessed with broad shoulders, which makes it appear that I am in better shape than I am. So you're not a big workout guy. Thank you, Scott. That's really nice. I go through phases where, 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. 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, I think it was 2009, it's become one of the most watched TED Talks of all time with 37 million views.

5:31By 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. 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?

6:07They 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. 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.

6:44And 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. How do you go about figuring out what your why is? 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 Y is fully formed probably by your mid to late teens.

7:17You 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 at 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. And what you very quickly discover are patterns. And if you can link those patterns together, you can articulate your why and, and your hows, which are the sort of your, your natural strengths or the environments in which you operate best.

7:55It 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? No, that's exactly how a why 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.

8:28So 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. 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. That's nice.

9:06You 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? 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 happened 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.

9:54And we don't get taught how to lead. So, you know, good leadership is actually, you know, 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 what are some examples if you're a manager and you want you're interested in demonstrating leadership what are some practical examples of that number one is is is uh is i think honesty you know uh 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.

10:42And 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 know a lot less about this than you do. I'm going to try and stay out of your way 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 here to tell you that you know more than I do, which is incredibly empowering for a team, 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.

11:16And 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 um and their their attitude is we know you're smart um 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 okay with that and and i just love that it 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.

12:00Isn't that more broadly great advice around relationships as well as leadership that I find with parenting, with relationships, so much of the time, the best response is just to listen? I mean, ask and answer, right? Like, this is where, for some reason, we've bifurcated our lives into, like, personal lives and professional lives. 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 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 the company.

12:39You'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. 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? 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 jobs on day one and legitimately we were idiots.

13:27like 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 where this younger generation that's coming up in a computerized internetted world they actually start day one of work with a skill set 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 a, it's a blessing and a curse, right? Like, like everything. The blessing is, wow, you start day one with a skill set that we need and don't have.

14:14Amazing. The downside is because they have a skills that other people don't have, it gives a false sense of, I know a lot. But there's still a lack of experience and there's still a need 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 two things which are wrong, which is offer too much deference to the younger generation because because they bring that skill set 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.

14:54And the answer is something in between. But I think that's a fascinating and modern dynamic that the previous generations just didn't have. They've developed a reputation, fairly or unfairly, for being a bit entitled. Do you agree with that? 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.

15:33I mean, these stories have become boring. 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 I, but it backfires. 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.

16:12That'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 increase what I'm making. Can we discuss the best way for me to do that? And that's a discussion and a negotiation. And I think it allows the person in leadership to feel included 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.

16:49And I think that's what good career management is as well, both up and down a chain of command. We'll be right back. Support for the show comes from Train Dreams, the new film from Netflix. Train Dreams is a film that stays with you. It's about a man standing alone against the backdrop of a changing America. What makes it powerful isn't the scale of a story, but its simplicity. It's a reminder that a life doesn't have to be big to be meaningful. That quiet endurance, grace, and decency are their own kind of heroism. In a world obsessed with progress, Train Dreams asks us to take pause and reflect on our relationship with loss, nature, and the need to belong.

17:28And maybe that's the modern journey, not domination or conquest, but learning how to live with change, grief, and tenderness without losing our sense of purpose. Train Dreams captures the tension between progress and preservation, between the machines that build our world and the nature that still defines it. In a time when we're all searching for purpose, Train Dreams feels timeless because the frontier isn't just a place, it's a state of being. Train Dreams, now playing only on Netflix.

18:01so 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 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 20s, early 30s, they 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.

18:34I look at what you do, and I mean this sincerely, I think 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. 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.

19:11You 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? 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 had a day off school. And, you know, he treated everybody the same. And 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.

19:58And 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 and and imparted that onto me and my sister which is you treat everybody like an executive and so that was that that served me very well throughout my career you know um 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.

20:38And, and they didn't help him out. You know, I saw it happen in front of me, you know, um, they were just like, sorry, you missed FedEx, you know? And with me, they'd be like, don't worry, Simon, we gotcha. So my career in advertising went well. Um, 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. They're like, well, one day I want to start my own business and they would hire me. And 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 um but uh 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 um and it was uh it was difficult i had a business partner who worked it worked for a couple years and then the relationship collapsed i i bought him out what was the business on it was a marketing consultancy variations on a theme and uh 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 had that false belief of how leadership works and, uh, life got really difficult.

21:58Um, and I went through, I think what can only be described as depression and, uh, thank goodness, uh, a friend of mine sort of had an intervention cause 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. Um, and I came clean and all of the energy that went into pretending that I was happier, 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.

22:33And I had a choice to make once I figured out this, it wasn't so much that I figured out my why it was like, I also figured out how to help other people find theirs. And I was doing it for my friends and my, 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 to people's living rooms. And the first decision I had to make was, do I put a TM on this thing called the Y, called the golden circle, and try and leverage it and monetize it as much as possible?

23:01And it was my first test of Y, right? Because my Y was to inspire people to do the things that inspire them. And I realized, no, I can't do that. And so if you go back and look, like there's no TM on the Y 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. Um, 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.

23:42And 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 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.

24:16I think that's a large part of it, you know, which is I try not to live on the successes of the past. The future is way more interesting to me. 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 at 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 if you don't have kids, it's the closest thing you have to kids.

24:51You conceive it, it looks, smells, and feels like you. And the failure is very public. And it rattles you to your core when it doesn't work out. And sometimes you've 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 down. When you're at that moment or when you were at that moment and you had this friend conduct an 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, have had 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.

25:34I 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 helped you get unstuck from a moment where you could have entered an actual downward spiral? There are two things, one that I learned in hindsight and one that I learned the hard way. Um, 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.