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I wear an orange strap on my watch. I always have a flash of orange somewhere on me. It's not for you, it's for me. It's a reminder. Optimism. It's my job, right? And it's a reminder to me. These little things. I have the word inspire embroidered in some of my clothes. Yeah, it gets tucked into my jeans. Like you're not gonna see it. I see it when I get dressed in the morning. It's not there for you, it's there for me. So I'm surrounded by pictures on my desk, you know, things hanging in my home, things on my body. I've chosen orange. I've chosen the word optimism as a reminder to me of my job. To help me stay in balance.
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A
I Don't know what they called it.
B
There was like, I don't know, let me tell you, it doesn't even matter what they called it. Cause there was just this one beautiful standout line that for me, I obsessed. I think I watched it every day for months and months and months ahead of launching Good American. So this is going back quite a few years now. And it was. People don't buy what you do, they buy why you do it.
A
True.
B
And for people that maybe, you know, if you're not one of the millions and millions and millions of people that have viewed that video, will you just explain for me out the gate what you meant by that? Because today I want to spend most of the time talking about your personal why and a lot of time talking about what good leadership really looks like. But I'd love you just to surmise that for those that don't know you as well as I think I know you.
A
Yeah, I mean, it's a simple concept. People buy into what you believe. Loyalty, love, all of those things come from connecting with you, a person, with you, a brand. People buy things that are cheaper. You know, these are transactional relationships. We don't have any loyalty to those things. And what I learned was that all the most inspiring brands, all the most inspiring leaders, from Martin Luther King to Steve Jobs, every single one of them thinks, acts and communicates the exact same way. And it's the complete opposite to the rest of us, them personally, and in the case of Jobs, this company, most of us tell people what we do. We tell them what the product is, we tell them what the price is, we tell them what the value is, we tell them what the features and the benefits are. And we expect that that's going to drive a behavior. But if you look at the biology of how people actually make decisions, it's something not rational. It's something deeply, deeply emotional in the limbic part of our brain. Our limbic brain controls all of our decision making, all of our feelings, but it doesn't control language, which is why it's hard to put sometimes these things into words. And the great leaders and the great brands are able to capture that thing that why in words that sucks us in and draws us in and makes us want it, even if it's irrational, even if it's more expensive, even if we can buy something better somewhere else. And so it's a true statement. People don't buy what you do, they buy why you do it is a biologically true statement.
B
No, I think, honestly, you couldn't be more right about that. And I feel like so many people in that moment were like, why am I doing what I'm doing? We all then obsessed over it. But I think it was like, for me, it was like somebody turned the light on all of a sudden, made everything that I was doing made sense. And it made so many of the mistakes that I'd made and the businesses that perhaps weren't successful. I was like, damn, why wasn't this so blindingly obvious? What was it about? And again, because so many people obviously felt like me at that moment when they saw you say that so plainly. But why was that not part of how we think? Like, why was that such a pivotal moment for people when you said it like that? Was it just the simplicity in what you said or that we knew it to be true? What do you think?
A
Well, you.
B
You.
A
You were an executive making gut decisions.
B
Yeah, all the time.
A
And the. The best entrepreneurs make gut decisions. You ask all of them, what's your secret? They all say the same thing. I trust my gut. Right. The problem is that's not scalable because you're the only person that knows what's going on. And it's not something you can explain either. You'd be like, I don't know. It just feels right. Even though all of the empirical data says, do the other thing Right. And so that's difficult. And so, as I said before, the part of the brain that controls all of our decision making doesn't control language, which is why we say it feels right, because the part of our brain that makes decisions is also responsible for feelings, not language. And so when I said it, it immediately explained the experience you were having. Right. I can put it another way if you like. There's a little metaphor I use called the celery test. We're all constantly getting lots of advice from the Internet, from articles, from friends, dinner parties, whatever it is. And the problem is, which advice do you follow? So let's imagine you go to a dinner party and somebody says to you, you know what you need in this economy? You need to be buying M&MS. I'm telling you, M&MS. I made so much money with M and Ms. You got to get into M&Ms. Somebody else says to you, soy milk. I'm telling you, you gotta do soy milk. Somebody else sees you Kit Kats. Kit Kats are the best thing in the world. And somebody else says to you, celery. All perfectly good advice from all perfectly good sources, from all perfectly successful people. You go to the supermarket and the problem is, which advice do you follow? What products do you buy? So you buy all of it. You buy Kit Kats and M&Ms. And celery and rice milk. You may get some value out of some or all of these products. We don't really know. You spend a lot of time at the supermarket. You spend a lot of money at the supermarket, and that's it, right? And when you're standing in the queue, when you're standing in the line to check out, people can see what you bought. Nobody knows what you stand for. Nobody knows what you believe, because you bought everything. Now, let's imagine you know your why. Let's say your why is to always be healthy and only do the things that protect the health of your body. You get all the same good advice from all the same people. The difference is when you go to the supermarket, which are the only products.
B
You buy, you buy the celery.
A
Buy the celery and the rice milk. Those are the only ones that make sense. You spend less time, you spend less money. You're guaranteed to get value. You're standing in the line, and everyone can see that you only have celery and rice milk in your basket. And people can say, hey, I can see that you believe in being healthy. So do I. You just attracted a customer or an employee simply by making decisions because what you do reflects what you believe, right? But here's the best part. The minute I said the why, I asked you what we buy, you knew without me having to tell you. Now, me as the entrepreneur, I'm making gut decisions every day. I know we're only going to buy celery, even though I can't tell people because of all the advice. But the minute you put the why into words, anyone can make the right decisions. So that's what was the light bulb for so many people, which is by putting it into words, other people can make the right decisions, the decisions that you would have made, because they can now see what you see. They now believe what you believe.
B
And that's the beautiful thing, because I think when, again, you put it so beautifully, when they believe what you believe. And, you know, I've been lucky enough to be part of some brands that have done that very, very early on, right? That have gone out on a limb and been very, very, very clear about their beliefs. What's interesting about that, because in business, we're kind of, you know, constantly looking at the lifetime value of a customer. Like, what does this customer mean to us on day one when they purchase and what do they mean down the line? And every metric, when you actually matter to customers, when customers believe what you believe, the metrics completely go through. And so you're actually building a way more healthy business when you do that. But it's not easy to engineer. So I was endlessly. I mean, I've read probably everything that you've ever written, but my favorite book that you've written is Start with why. And there were so many reasons for that. But I loved that you took it into this kind of personal realm, because anybody who had been fascinated by this particular speech in this particular video then started going, well, what was my why? And that's what I did. I really went deep inside because I was like, I can figure it out for these businesses, but far harder to do it for myself. And I think that right now we're in a moment in time where there's so much insecurity in the world. There's such a lack of optimism. People question everything. We're sitting here at this moment where, you know, we talk. I feel like every conversation I have leads to this existential conversation around AI. And so my question to you is, really, how do people even begin to understand their own why? What do you do if you really don't know?
A
Well, there's a process. I mean, anybody can uncover their why. We are all the sum total of how we were raised. You are who you are because of the experiences you had growing up. And your personality was fully formed probably by your mid to late teens.
B
You think it's that late? Looking at my kids, sometimes I feel like it's even earlier.
A
I mean, you know, Piaget would say 13. The youngest person I did a Y discovery with was, I think, 16 or 17. But the rest of our lives offer us opportunity to live in balance or out of balance with who we are. Just because you are who you are doesn't mean you're living to. You're not necessarily making the decisions that show people who you are. Sometimes when we start chasing money and fame and our friends say, it's like, I don't know who you are anymore. Right. Well, that's because you are who you are.
B
I'm interested to understand how. How someone finds their why without blowing their life up. Right. Like, is it's again, for so many people. They might feel misalignment with their job. They might feel like they're out of living outside of their truth. But how do you do it if you just, you know, you're like, I have bills to pay. I'm Trying to live a regular life, but I just need to get closer to what.
A
Those are two different conversations.
B
Yeah. Tell me that.
A
Knowing your why and making decisions and choices that help you work to your natural best, that's a different conversation.
B
I want to have both of those.
A
Yeah. I mean, it's a journey, right? It's like, think of it like exercise, which is if you want to be healthy, you have to go to the gym, you have to eat right. You have to get enough sleep, you have to nurse your personal relationships. And once you achieve that, you have to keep doing it for the rest of your life. Like it's a journey. You're never perfectly healthy. These things wax and wane. They're affected by stress, they're affected by jet lag, they're affected by whatever, right? It's boredom, they're affected by laziness. And so it's the same thing. Once you know your why, the rest of your life is the pursuit of trying to keep it in balance. It's the same thing. It's not an achievement, it's a journey. But learning what your why is, which is the starting point. That's why the book is called Start with why. That's why college graduation is called Commencement. It's the first day of the rest of your life. It's not the end, it's the beginning. But I can get people to the starting line. I can't get them to the finish line. So the starting line. I'll give you a fun little exercise called the Friends Test. Do not do this with a spouse. Do not do this with a sibling. Do not do this with a parent. Those relationships are too close. Do this with a best friend. The kind of person who, if you call them at 3 o' clock in the morning, you know, they take your call. And you'd be there to take their call. Same thing, right?
B
I have a solid four of them, right?
A
You're ride and die, right? And ask them this question, why are we friends? And they're gonna look at you like you're crazy. Because again, the part of the brain that controls feelings doesn't control language. It's hard to put our feelings into words. But then, weirdly, you actually stop asking the question why? They're gonna look at you like you're nuts. And they're gonna be like, I don't know. No, they just can't put it into words. They do know. And then you stop asking the question why. You're like, okay, what specifically is it about me that I know? You'd Be there for me no matter what. And they're gonna hem and haw like, I don't know. And they're gonna start describing you. I don't know. You're honest, you're reliable, you're fun. And you play devil's advocate. You go, you have that from other people, too. What specifically is it about me that I know you'd be there for me? No matter that you'll always be there. And for some of them, it'll be stressful. Do not help them. Don't let anybody else help them. Let them go through the process. Play devil's advocate no matter what they say. You say, what specifically is about me? And eventually they'll give up. Eventually they'll stop trying to describe you and they'll start describing themselves. And this is what my friends said to me. They said, simon, I don't know. All I know is I don't even have to talk to you. I can just sit in the same room as you, and I feel inspired. And I got goosebumps. I'm getting them right now. Because what they put into words was the value I have in their life, the space that I fill. And the reason I had an emotional reaction, whether you well up with tears or you get goosebumps, is because it's tapping deep inside you what it is that you're supposed to give to the world, what you're supposed to give to people. And if you do this exercise with multiple friends, they will say similar, if not the exact same thing, because your value to the world is the space you fill in their lives, which is why we can have many friends, because you can't fill all the spaces. And so I know that. I know that my why is to inspire people to do the things that inspire them. And my job, my love, is to figure out the ways that I can do it as a brother, as a son, as a friend, as a leader, as a follower. Like, whatever my role is, that is my job. And I am in balance and at my best self. I am my most fulfilled. When I'm trying to do that again, it's a pursuit. It is not. I am not. I get it wrong all the time. I'm subjected to all the same stresses and strains as everybody else. My ego, my insecurities, fatigue. And these put me out of balance. But I at least can say, and then I can work through it and I can ask for help. I can also give myself grace because I am imperfect, as we all are. But when you know your why, when you know the starting point, then you can say, okay, my company fulfills this. They're not perfect at it, but I can help them. Or you can say, my company, they only care about shareholder value, they only care about profit. They don't care about anything else. They have no sense of purpose or cause. They're mercenaries. I don't belong here. Do I quit or do I, do I be the leader I wish I had? Do I create a little fiefdom of inspiration and fulfillment with the people around me? Because I can bring inspiration to the person to the left of me and the person to the right of me. And I can find intense joy and fulfillment in my team even if I don't align with my company. So quitting is an option always, but it's not always the only option. And that's one of the challenges I think young people have today, which is they think quitting is the only option if they're misaligned with the company. And the problem is 100%, the problem is you're going to be misaligned with the company, sometimes in part, but sometimes in whole. Because unfortunately, too many companies today are more finite, oriented, are more driven by the short term gains, the shareholder value, the money before the people, money at all costs. And so unfortunately that's too common. And so you're gonna struggle to find a really great, inspiring company. They exist, we love them, but they're few and far between, but there's not that many of them.
B
And so you set up.
A
But there's good, good people and good things and great teams in shitty companies all the time.
B
So what do you say to somebody that's in a position perhaps where they feel like they, let's say they go and they do your exercise and they understand what it is that their friends love about them. They understand the value they have in.
A
Their friends lives, as I would put.
B
It, the value they have in their friends lives. I know that everybody is dying to like stop the podcast and actually call up a friend. In fact, I mean, that's what everybody should do. They should pause, call a couple of friends and then come back and listen to the podcast.
A
The exercise won't fully answer the question, but it'll get you, it'll get you in the ballpark, it'll be actionable.
B
I love the way that, I mean, first of all, of course I've obviously done this, but I think it's so interesting that with your answer that you inspire your friends, that you've then built the career that you have, right? So this is really powerful stuff. If you take this in and you take it seriously, I mean, you've built an entire ecosystem, infrastructure, company way of being a branded Persona around your why. And it's really working for you in the way that I've seen it work. When a company has a why, I.
A
Would agree with you on every detail you said, but I'd push back on one.
B
Tell me.
A
Branded Persona.
B
Oh, go on.
A
This is who I am. I am the same on and off camera, you know.
B
Well, I don't think that if you have a branded Persona that it's necessarily manufactured or inauthentic.
A
Yeah.
B
I mean it from the way. And so let me say it better to you. There is no mistaking that you are a person that inspires. Like, if you hadn't told me that your friends think of you that way and you said to me, emma, what do you think? I would go, you're a super inspiring guy, Good inspiring guy.
A
That means I'm doing the work.
B
It's like I get you on Instagram and I'm just like, oh, my God, I feel so inspired. Like that there's not like, oh, what are we feeling today? It's like, that's what you were clearly born to do and it's what you are doing. And so I don't mean it in an inauthentic way. I'm just like, that's who you are.
A
But I think it's worth touching on only because I think there are too many people, especially in the sort of modern social media influencer world, that their idea of authenticity is like crying on camera. You know, that's not authenticity.
B
Don't even get me started.
A
That's not authenticity. Authenticity means. Authenticity means I say and do the things I actually believe. That's what authenticity means. Authentic doesn't mean just like speaking my truth. Like, that's.
B
No, it's not. It's the least vulnerable thing that you can do is to spy on camera.
A
And I have no problem with people building brands around themselves, obviously, but it should be driven by who you are and that you impact you want to have in the lives of people and the world you want to live in, that you're trying to build rather than tapping into some sort of zeitgeist, some sort of like, cultural thing. And then you're like, I'm going to be the voice of that. You know, that'll fall apart. That'll. At some point. At some point, the truth will show up. And we've seen it happen. Right? We saw it happen. I mean, two very notable Expressions of that were, I'd say, Tiger woods, you know, he wanted to be the good boy of golf. Turns out he was the bad boy of golf right now. He could have just been the bad boy of golf, and we would have loved him just the same. Bad boys in sports and we, like, you know, there they are. But Ellen is the other one, right? She told us she was this wonderful, lovely, kind, generous, sweet human being. Turns out, not so much. Not so much. And again, if David Letterman was a curmudgeon and a grump and every kind of everybody kind of knew he was kind of a.
B
No, we accepted, as long as you are basically it.
A
And he didn't lie about being a bit of a prick. He was a bit of a prick. He either liked you or didn't like you, you know, and so, meh. It's okay. It's like, we know what we're dealing with and we know who you are. And so the point being is, when I heard a branded Persona, what it sent me to was, like, Tiger woods and Ellen, which is. That's a branded Persona, which is. I'm gonna develop a brand, but I'm not gonna live that brand. I'm just gonna be that brand.
B
Well, because I think that in the culture, we are surrounded by so many more people. And what brand sells, right, like that they. That they curate something around themselves that has nothing to do with their purpose or with their why. And then they do a lot of work to put that idea forward. But I. My.
A
Or it's for public only.
B
Yeah, but my argument would be that when you. I mean, again, going to your best friends in the world and getting that information, right. It comes from a place of honesty and it comes from a place of truth, because hopefully that they're giving you that. And what you can do with that information is so powerful. And I look at you and I go, that's so interesting that you took that and you ran with it, and it's been so that it's really worked for you in such a way. And so for somebody that tries this at home, I'd like to understand, like, once you had that piece of information, like, what did you do with it, and why did you take it so to heart and decide that you would anchor everything else around that?
A
Well, I realized, first of all, it was a source of passion, right. This came at a time in my life where I'd lost my passion. And so I went through this exercise to regain my passion. It wasn't supposed to be. I wasn't supposed to Write books or do talks. None of those things were in any plan. I never thought I had a book in me, really. I have no desire to be a public speaker. Right. Still don't. I'm living proof that having a plan is hilarious, because nothing I'm doing was on any plan and continues not to be.
B
The difference was I can't even deal with that information. I'm the most planned person in the world.
A
So, I mean, I could probably benefit from a little more planning. But there was no, like, life goal. One day I'm going to write a book. Like, that wasn't. And when I wrote my first one, I'm like, all right, that's it. I'm done. And I wrote the second one. I'm like, all right, I'm done. The difference is the starting point. I didn't start with an end goal in mind. I started with a solid foundation. I have a thing that has value to me. I now feel inspired by this thing called the why. The first thing I'm going to do is I'm going to share it with the people I love. That's how it started.
B
Give me an example of that.
A
So this why concept, when I came up with it, was again, for me, was the first thing. It's like, you see a great movie or you read a great book, what do you do?
B
Share.
A
You tell your friends. You're like, oh, my God, you got to see this movie. Why did you do that? Why did you tell your friends that they have to see a movie? You're not the cruise director. You're not responsible for their social lives. Why would you tell a friend? They didn't ask. Oh, my God. You have to see this movie because you want to. Because you share. You want to share goodness with your friends. That's who we are. That's what it means to be a good friend. Right? Which is we give our friends recommendations. Why? So they'll have better lives. I did the same thing. I'm like, I gotta tell you this thing, it's so powerful. I gotta share it with you. And I would help my friends find their why. And my friends started finding renewed passion in their work. Some of them even started businesses. And they wanted to share it with their friends. So they called me and said, can you come to my apartment and tell my friends about this? And I said, sure. And I literally would stand in someone's living room and talk about this thing called the why. And we'd get one of those supermarket crudite things, you know, with the celery and the dip in the middle with a big plastic lid. Like, we'd buy one of those and put it on the table. And I would talk about this thing called the why. And some of their friends would, can you help me find my why? And I would help people for 100 bucks on the side. And it wasn't supposed to be a career, it was a side gig. But I found that it brought me such joy and it made me feel so myself that it's all I wanted to talk about. I'd go for meetings and people like, so what do you offer? And I wouldn't even, like, do the thing. I would just be like, okay, I gotta tell you this, I've got this. And I'd start drawing circles on napkins.
B
You know, you love a circle.
A
You love a circle. I do love a circle. I do love a circle. I've seen the more people I told about it, the more people wanted it. Then somebody said, can you come talk to our company? And so. And somebody said, you should write a book. And I was like, I don't know how to write a book, you know? And I had a meeting with a publisher. I had a 29 minute meeting, and three days later, they offered me a book deal. It's not because I'm smarter than anybody else, and it's not because I had more connections. My connections emerged because the more that I started with why, the more I learned to speak about what my why was. People who believed what I believed said, there's somebody I need you to meet. I didn't know anybody in publishing. I met somebody who was inspired by whatever it is I was saying. She says, I need you to meet somebody. I met him because, sure, you know, I talked to him on the phone. Turns out he's an editor at a big publisher. He says, you need to meet my boss, who's the publisher. I went, okay. And so he made the meeting for me. My. My agent didn't do it. It was these. The more I talked about why the people who believed what I believed wanted me to meet people. Not for me. They don't care about me. It's because, like you said, I put what you were feeling into words. I helped you see something that you knew to be true. Now you had some clarity. And so I was giving them clarity and I was giving them words. And I was now the tool. They wanted to share me with other people for them, not for me. And so things started getting crazy quickly. And so, you know, start with why. And I just came out with the 15th I mean, it's embarrassing, but the 15th anniversary edition just came out.
B
That's crazy.
A
I know. And it was fun to edit. It was fun to edit because I was like, do I have to rewrite this thing? Is it still relevant? And I went through it and read it, and we'd, like, change the grammar, and, like, we put a couple of, like, one of the most common questions I got on the first edition, I wrote about TiVo. And, like, all the young people would be like, what's a TiVo? So I. Instead of taking the case out, I just went and explained what a TiVo is. So it was like I. I brought it into the modern era and made some explanations of things that I took for granted back when I wrote it. But the amazing thing about Putting out that 15th anniversary edition, it's 100% true. It's 100% relevant. Still true. Nothing's changed. Nothing has changed, which was super fun. But all of these opportunities came about because people who believed what I believed wanted me to meet somebody they thought that would help them. And I just kept saying, yes. My point is that Start with why book, which is now, you know, a decade and a half old, that's my bible. Like, that's how I live my life. And even though I don't talk about it as much anymore, it's in me. It's who I am. It's what I believe. And I gave away the entire game plan that I used to build a brand, to build a business, to work at scale, to bring these things to life in a compelling way that had relevance in other people's lives. And it's all in there. I learned to start with why. I learned to speak with why. I learned to think with why. I learned to make decisions with why. And I was obsessed with the law of diffusion of innovations, which is work with the early adopters, work with the people who believe what you believe, the majority of the people who just want what's in it for me, you know, if it doesn't work, will I get my money back?
B
You stay away.
A
I stay away from. And I allow other people to help me build and carry the message. And so literally, that is my blueprint for how I did everything.
B
And so all of these years later, you still believe exactly what you wrote, and it's still working.
A
100%. 100%. 100%.
B
And tell me this. When somebody finally discovers they why, let's say they go through this exercise and they figure out their why, is it like, you know, when you start a new habit do you drift off sometimes enough to find your way back to your. Why? I'm trying to understand. How do people constantly remind themselves it's about balance?
A
It's about balance. Right. Of course. Like, sometimes you spend a few months and you are unhealthy and you get into some bad habits or stress gets in the way or work gets in the way or whatever it is. Of course. And so, yeah, of course I veer from why. This is why I talk about balance, not about right or wrong. I talk about the work to stay in balance. Of course I fall out of balance. And so, like anybody who has any kind of belief structure, I surround myself with symbols. Right. If you're religious, very often you hang a religious icon in your home or in your doorway or around your neck, and it's a little reminder to you of the life you want to live. Or you put pictures of your family as a reminder of what's important to you. I wear an orange strap on my watch. I always have a flash of orange somewhere on me. It's not for you, it's for me. It's a reminder. Optimism. It's my job. Right. And it's a reminder to me, these little things. I have the word inspire embroidered in some of my clothes. You know, it's sometimes in the bottom part of the shirt, whatever you call it.
B
Yeah.
A
It gets tucked into my jeans. Like, you're not gonna see it. I see it when I get dressed in the morning. It's not there for you, it's there for me. So I'm surrounded by pictures on my desk, things hanging in my home, things on my body. You know, little flashes. I've chosen orange. I've chosen the word optimism as a reminder to me of my job to help me stay in balance. Do I get it wrong? Oh, my God. All the time, a million of times a day.
B
Give me another little practical tip for people that want to be constantly reminded of their purpose. Because I love that. Like, I look at you now, you've got the orange on your socks. You have the orange there. It's like, that would be a key thing to do. What else do you think that people.
A
You have to talk about it obsessively.
B
Obsessively. You've been talking about it for over 10 years.
A
Like, it's all I want to talk about. I love talking about ideas, but when I discovered why it's all I wanted to talk about. It's the only thing I wanted to talk about. And if you look at the progression in the things that I'VE written, the talks that I've given, the videos that I put out. There's a through line through all of it, from why to Leaders Eat Last to Infinite Game, to what I'm working on now about friendship, to the companies I've built, to the app that we're developing, to the training we've done. Because now we're training coaches on how to help their clients find their why. We're doing that now. So if you look at the through line through all of my work, it's about relationships, it's about people, it's why I'm writing about friendship now, the businesses that I've built, yes, it's about leadership and culture and all of that stuff. But reality, it's about about people getting along with people and people taking care of people. That's what it's about.
B
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A
Of course. I have solid foundation, I have more confidence, I have a calm, I have things that I can easily say no to.
B
It's a filter for you.
A
Yeah. I mean, I remember when I was getting going and I didn't know how to I had this idea and I didn't know what to do with it. I knew I didn't want to be a consultant, but that was the easy way to start. So I did start that way. And I would get advice from people who were much more successful than me, made much more money than me, and I was living. I Mean, I was really like, paycheck to paycheck. Like, it was. I was like. It was a. You know, it took a while, but it was fun. I mean, I wouldn't call them rough. They were, you know, austere maybe, but not rough, because it was fun. Without my why, the money was stressful with my why. I just was like, it's okay. It'll be fine. But I would get advice from people who are much more successful than me, and they would tell me to do things that were probably right, but it didn't feel right to me. And instead of me just going, that doesn't feel right. In the face of empirical evidence that they're more successful than me, I now had a filter to say, no, I'm not following their advice. I'm not doing it. And here's the reason why. Because it'll put me out of balance. It won't advance my cause. It's not what I want to pursue. And I'm willing to make money more slowly to do the right thing than make money quickly and do the wrong thing. And I ignored their advice, and things have gone just fine.
B
Yeah, it's really worked out. Who taught you to communicate so well?
A
Oh, that's one of the blessings of having adhd. I struggled as a student in school. I can't read very well.
B
Did you get diagnosis?
A
No. I only got diagnosed in my 30s. I mean, I can physically read. I can read fine, but I'm very bad. If you give me, like, a textbook and blocks of text, like, even now, if you send me a long email.
B
You'Re bad with textbooks.
A
Yeah, if you send me after all those books.
B
No, you can't be.
A
I've written more books than I've read.
B
Is that true?
A
That's a true statement. I used to carry a lot of shame that I struggled to read.
B
Same. I mean, I'm super dyslexic. I actually don't have a problem reading, but I carried a lot of shame around it and my inability to connect with text sometimes and to take information in quickly.
A
So I struggled to read. I can't learn from reading because my mind wanders. I can't.
B
So how do you learn? Oh, having a chat.
A
What I had to learn to do is I couldn't skip class because if I don't hear it, I'm not learning it. I can't just skip class and go read the book. It's not going to work. And I had to learn to ask questions of my friends and of my teachers. And then I Had to learn to say back what I think they're saying to me to prove that I understand it. Because if I can't say to them what I understand, then I'm going to fail the test. So I can't just ask them and they explain it to me and go, got it, Got it. And then I sit in front of the test. I'm a goner. Because we all think we understand until you're like, until you have to take the test and then you're done. And so I had to learn to process information that I was asking for, say it back in terms that I can understand, that they're affirming that, yes, I'm right and I'm accurate, then I have learned it. Now I can go take the test. So that wasn't some. I had to learn that or I would fail school. So you have a choice. Fail or find another way. Thank goodness I found another way. Now that's my superpower. I'm a great believer that the solutions we find to the challenges we have as kids become our strengths as adults.
B
Oh, I couldn't agree more.
A
And so, you know, this is a different conversation that, you know, you should have with better qualified people. But, you know, if we. If we help our kids solve every problem, what kind of strength will they have as adults?
B
Forget about it.
A
So different conversation. Struggle. Struggle. Struggles are good.
B
I would love to. It's a conversation I would love to have because I'm obsessed with, you know, like, I'm a figure it out parent.
A
Struggle and challenge is a good thing.
B
Figure it out. And it's the best thing that you could ever do for anyone. I mean, I spent my whole life just working things out. Between the age of, I don't know, 7 and 15, it was like I was on my own. And actually, as you quite rightly say, my biggest strengths came out of those. Because you just didn't have a choice.
A
Of course, you didn't learn anything from when things went well. You know the story of Richard Branson, what his mom used to do?
B
No. Tell me.
A
His mum would drop him off three miles from home and say, see ya. And he would have to walk home and figure out how to get home. And she would say that it would take him hours. Cause he would stop and look at everything and want to, like, explore everything. It would take him hours to get home. No, clearly, don't do that in this. Not now. Not now.
B
Don't write for Richard in the, you.
A
Know, in the countryside. And then back in the. Whatever it was, the 50s or the 60s, whatever it was, you know. So, yeah, don't do that, don't do that. But the point is, is that this entrepreneur who's this renowned problem solver who has no fear, well, where do you think that came from? It's not genetic. No, it's because his mum, he was put in these difficult situations and he had a mum who pushed him and pushed him and pushed him. Our parents obviously play a huge role, but the situations we're in and when our kids struggle, instead of swooping in, being like, all right, what are you going to do? And I'll tell you, even as an adult, the best leader I ever had. His name is Peter Intimaggio. He was the big boss in the company I worked for. He wouldn't answer a single question. It was so annoying. I'd be like, peter, this happened, what should I do? He'd be like, I don't know, what do you think you should do? I think we should do this. He goes, well then you should try that, shouldn't you? Or I'd go to him like, peter, what should I do? He's like, what do you think we should do? If I knew, I wouldn't be asking you. He's like, well, you better come up with something. Like, the fricking bastard wouldn't answer a single question. But what he taught me was self reliance. What he taught me was to be more resourceful and ask more questions and go dig and then if you come up with something, try, try in a little bit to experiment, you know. But yeah, he wouldn't fix anything for me. It was annoying. So annoying.
B
Sounds so annoying. Just like me as a parajo.
A
Just tell me the answer, make my life easier. What do you go?
B
No. But it's incredible what comes out, you know, I, I think about this with my kids all the time because they come up with things that I could never, I would never have told them. And I'm like, wow. And it's so individual, right? The way my 11 year old approaches things and the way my 9 year old does, it couldn't be further apart. But in that is all the magic of who they are and where they're going to find their strength, where they're going to find, you know, all the great parts and the superpowers of them.
A
And as leaders we have to be careful. You and I both have big personalities, we have a lot of opinions, right?
B
I've heard that can be problematic sometimes.
A
And when we're in a meeting and somebody's talking about, should we do this. Or what can we do this? We say what we think and a whisper is a shout. And so even though it's a thought, it becomes a command or a decision. Or sometimes we do just say, oh, just make it this, just make it that. And it's usually because we do have opinions. And it's also because sometimes we give in to the pressure and the time, the timing of things.
B
Yes.
A
But in reality, and I have to be better at this, which is to say, well, what do you think? And defer and sometimes wait and sometimes allow things to maybe not be as efficient because I'm teaching other people how to make decisions like I was taught how to make decisions.
B
It's a great skill as a leader. And I want to talk to you so much about leadership because you've got such great insights to offer. But one of the things that I love, Simon, that you talk about so much is this idea of helping others. And you know, I started this show because I really want. This show is so much about becoming and being the best version of yourself. And you talk about the only way to do things is to do things together. You have this lovely quote, I don't want to kill it, but you say there's an entire section in the bookshop that's called self help and it should be called Help Others.
A
And there's no section called Help Others.
B
Yeah, there's no section called help.
A
That's 100% true. Yeah. Like we're obsessed with helping ourselves and I would like us to see obsess more with helping others. That is true.
B
So why do you think our goals should be in pursuit of something broader than just ourselves? How is that helpful?
A
Well, for better or for worse, we live in the world with other people. There's no getting away from it. And I don't know a single person has accomplished anything of note in their lives who did it alone. Some of them may take all the credit, but I still guarantee that somebody took a risk on them. Somebody made an introduction, you know, somebody said, you got this. Somebody gave them some money. Somebody in their hardest time said, I still believe in you a million percent.
B
That's why I had such a problem with the term self made, because I'm like, I haven't done anything.
A
No, I'm group made. I'm a group maid entrepreneur. Yeah, 100%. I mean, people took. I mean, like I told you, my publisher, I'm an unknown quantity with no followers, no TED Talk, no nothing. No big company, no track record, just an idiot.
B
Fucking good idea.
A
An Idiot with an idea. And he says, I'll give you a book deal. And I have no manuscript, no nothing. I mean, how can I not say thank you to that guy for taking. Because I talked to other publishers like, well, can you give us a 90 page proposal and tell us what your marketing plan is? And you know, don't get me wrong, I'm a publisher now and I like those things. But this person took a risk on me, so he's part of my success story. How can he not be my sister, who through thick and thin never left my side, how can she not be part of my success story? Right? And we work together now. It's not even my success story. It's our success story. And I said, I mean, I'm obsessive about it. My housekeeper in New York, I remember telling her, I remember, like, just so you know, you are part of all of this. I said to her, you don't know, like, when I come back from a business trip and I'm exhausted and I. And I'm tired and I walk into my apartment and you come once every two weeks and you're amazing. And I just want you to know you take so much pride in what you do. And I walk into my home because I left it a fricking pigsty. And I come home and you have no idea what that does for me to walk in and just be like, ah, you know. And I said, so the energy I have to go out and do it again in part comes from you and that you're taking care of me. And I mean that 100%. Like, I'm obsessed with, like all the people in my life who work with pride and work with love and who want to take care of me for no other reason than they kind of get a kick out of me. They are a part of the story. It's not just the people with the connections and the thing. Like this is somebody who and is 100% true. It's 100% true.
B
And you believe that true fulfillment can only come when your larger goals, your larger pursuit is in something like bigger than just you. You have to be helping others.
A
You have to be helping others. I mean, we, first of all, if you look at all of the things that we want in life, like, we want to be trusted and trusting. Right? Everybody wants that. Okay, well, here's some bad news for you. You don't build trust from people by offering them help. You build trust by asking for it. Giving someone the opportunity to serve, right, Is an act of service. A friend of mine.
B
Say that again for me, Simon. Giving somebody the opportunity to serve is an act of service. I think that's such an amazing framework because there would be so many people sitting, listening to this, thinking, how do I help someone? I have so little. But you're actually saying, and allow someone to help you.
A
Let someone in.
B
Being vulnerable, being open about what you need, letting someone in. Let someone in is an act of service in itself.
A
It is more than an act of service. It is an essential component of being human. We're social animals. We need each other. And people want to feel needed, people want to feel wanted, and people want to feel like they matter. Nobody will feel like that if you just go to them and go, you matter. Write it on your mirror in the morning. You matter. Right? Daily affirmations aren't going to do that. Okay? They're a salve. They'll feel good in the moment. And then you will say, 20 seconds. 20 seconds. They're a nice little hit, right? If you really want that feeling of value in the world to make you feel like you matter, give somebody else the opportunity that they matter. And the easiest way for somebody to feel like they matter is for you to tell them that you need their help, and their help will help you. And not because you want them to do a job, but because you are stuck and you don't know how to do that.
B
I love that so much because I think, especially for women, we feel constantly like we have to be there for everyone else. And that reframing to think that actually by being vulnerable, by asking for help, you're giving somebody else the honor of serving their purpose of being in.
A
That's true vulnerability.
B
Something else.
A
And I'll give you. And I'll. And we've distorted it. That's true vulnerability. I see it all the time. Like when I watch social media, I see somebody post a video.
B
The crying video.
A
The crying video. I just broke up with my boyfriend or girlfriend. I just. I'm struggling. And thank you guys for being there for me. You know, I don't know how many times they shot that. First of all, like, what take that was? But we'll put that aside.
B
Let's just, you know, it wasn't one.
A
Let's give them the benefit of.
B
Say we know it wasn't one.
A
Let's give them the benefit of the doubt that I'm far more generous.
B
Take fucking 15. She got it. She cried appropriately.
A
Let's go. Yeah, let's give her the benefit of the doubt that it was a one and done. And they're pouring their heart out about the pain they're in. And I just want to share this with you. And this is what I'm struggling with. And this is my day. And my question is, call a friend. Better sit with a friend and say every single word. You just sit on camera. Yes. And by the way, that's way more difficult. It is way more difficult to sit eye to eye with somebody or even on the phone, not a text, eye to eye with somebody and be like, I just broke up and I don't know what I'm doing and it hurts. It's easier to say when you're sitting by yourself in your room with a camera than it is to say to a friend and if you want to feel loved and if you want to give someone else the ability to love you and the feeling that they matter and the opportunity to serve, that's vulnerability. It happens privately.
B
But why has that become so very difficult? Why is it easier to cry alone and share with however many followers you've got than call a mate that really knows you?
A
Because I think there's distortion of the word vulnerable. Right. I think there's a difference between broadcasting your emotion. Brene Brown talks about this as well. There's a difference between broadcasting your emotions and being vulnerable. They are not the same thing. Vulnerability, another word for it. And I don't like the word because it's kind of lost its definition because it's so overused. A friend of mine doesn't use the word vulnerable. What she uses is the word available, which I really like. I want to be available. I want to make my emotions available to my friends to hear them. I want to be available to other people's opinions. I want to be available to the uncomfortable feeling of being helped. I want to be available that someone, that I make mistakes and someone knows how to help me. I like the term available. And I don't think that when we're posting online, we're that available. We're inaccessible. Were over there, like onto the next.
B
Onto the next, you know.
A
And look, don't get me wrong, when people post these things, it does help people feel seen and heard. I'm not debating partially.
B
I mean, I guess there is a.
A
I'm not debating that there isn't value in some of it. But the thing that I'm questioning is, are we actually, again, is it a short term thing? Because at the end of the day, we have to do the work ourselves. Right? That's why I say start with why. I'll give you A great starting point. I will give you an amazing. I will guide you, I will coach you, and I will get you to the starting line.
B
But the race, you gotta do yourself.
A
But you gotta run the race yourself. I'll cheer you from the sidelines. I'll hand you a glass of water now and then. Every now and then, if your ankle hurts, I'll give you some. You know, I'll give you something that'll help your ankle. But it's your race to run. Like, the coach stands on the sideline, the coach doesn't play. So I think we forget that part, which is, at some point you gotta get in the race. And at some point you're gonna get tired, and at some point you're gonna get demotivated. And at some point you wanna give up. And at some point you think you're weak. And at some point you trip over and again. It's unbelievably helpful to having people cheering from the sidelines to know that we're not alone. I ran the New York City Marathon many years ago. Friends of mine who had done it told me to do something which was kind of corny, but I did it. I wrote my name on my shirt. Just in electrical tape.
B
I love that.
A
I just, in electrical tape, wrote my.
B
Name so we could all cheer for you.
A
But people would cheer my name as I run back. And it made a difference. People screamed my name as I ran past, and it mattered. Yeah, right? Yeah. It was an amazing.
B
On the sidelines and whoever's name you see, you're like, come on, Michael.
A
Like, it's an amazing. But I can tell you from the.
B
Receiving end, it's amazing.
A
It's. All of a sudden you feel like they're cheering for you. Clearly, they're not.
B
But I was.
A
Well, then, come on. But maybe they were. Maybe they were. Maybe I shouldn't be so cynical. You know, they saw my name and they cheered for me, you know, and so it's only reinforcing the point that we've said, which is this is a group effort. We need each other. But you have to let people in to help you to make it a group.
B
Yeah.
A
It's only you if you're the only. If you're only if you're always the helper. That's martyrdom. That is not helping.
B
That's different.
A
That is different.
B
So you say that fulfillment comes from service. What does that look like for somebody, you know, someone who's just going through life every day, Someone who's not necessarily leading a team or a company, but still really wants to make a difference.
A
Do you have a colleague?
B
Yes.
A
Yeah. You can be the most junior person in the world. Right. And the most entry level. You're just graduated school and you got your first job and sitting next to you is the other kid who started yesterday. Look after them, take care of them. You good.
B
That's being in service.
A
Of course, service is uncomfortably simple. It's worrying about the person to the left and the person to the right.
B
It's basic stuff.
A
It's very simple things. It's very basic stuff. It's the person to the left, it's the person to the right, it's that. A friend of mine who's a general in the Marine Corps, he says his test for leadership and I would argue as a test for service, is that when you ask somebody how they're doing, you actually care about the answer as opposed to how are you? Good. Good.
B
Maybe not.
A
We ask the question to be polite. But if somebody's like, ah, it's been a rough day to be like, I can't right now, then don't ask the question. It's okay not to ask the question. But if you're going to ask, do you actually care about the answer? And that's his test for leader. Leadership. And I would argue that somebody who chooses a life of service is what I would call a leader. That's what a leader is. You choose. Leadership is the acceptance of the awesome responsibility. Awesome by all its definitions, it's amazing, but it's also big. It's the acceptance of the awesome responsibility to see those around us rise. That's what leadership is. It sounds like being a parent. It's true. You've accepted the awesome responsibility to see these little people rise and become the best versions of themselves. Sounds like a good leader at work. Sounds like a good entry level job. I'm going to make sure that you you good, you're good, we're good, you know, It's a relationship.
B
It's a relationship, you know.
A
And my definition of a friendship, my definition of a successful romantic relationship, my definition of a successful corporate culture, my definition of a community is all the same definition. A relationship is two people who we agree to see each other rise. A community is a group of people who agree to help each other rise. A successful romantic relationship is two people who agree to help each other rise.
B
What a beautiful definition.
A
Actually, I'd even take it easy. Step further. It's the agreement to see each other grow more than rise. A community is a group of People who agree to grow together. A strong corporate culture is a group of people who agree to grow together. A good romantic relationship is two people who agree to grow together. A successful friendship is two people who agree to grow together. There are different definitions of how you do that. Right? And that's why we need all those relationships. And there are different ways you do that. But you and I both know this. Which is the most successful friendships. I have the best corporate cultures I've ever worked for, the best romantic relationships I've ever had. That whether those relationships succeeded or failed, I am a better version of myself because of the relationship, not in spite of it.
B
Yes, no doubt and no doubt.
A
And they would say the same, that it didn't work for whatever reason. But I am grateful. I am a better version of me. And to build a corporate culture and be a leader where every single one of us shows up to help each other grow and be the best versions of ourselves. So when you show up in that entry day, it's so hard because we want to prove we're worthy. When we prove that they made the right choice to hire us. We want to prove that we're promotable and prove that we're great and. And not. Or. And do the exact same thing for the people sitting next to us. I want to help you be the best version of you. I want to help you be the best version of you. And that means I can't do the work for you. I can't swoop in and solve all the problems. But I can stand on the sidelines and I can be there to sit and load when you need me to.
B
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A
Oh, simple. Most people think being the leader is being in charge. That's what they think. Incorrect. Being a leader means you take care of those in your charge. Being a leader, as I said, is the acceptance of the awesome responsibility to see those around you rise, whether you have formal rank or not. You and I both know lots of people who are very, very senior who people do as they say because they have authority, but nobody trusts them, nobody likes them, nobody would quit a job for them to follow them. And you and I both know people who may or may not have that much formal authority, but people trust them and love them and would follow them anywhere and if they left A group of people would follow and go with them. That's leadership. Leadership is. Is an act of service. And when people feel like you have their back and you want to see them succeed, they will reward you with love and loyalty. That's what happens.
B
Do you think that great leaders can exist in bad corporate culture?
A
Yeah, of course. Yeah, of course.
B
And what do you do about that? If you feel like you are a leader that has your team's back, that has. Is there to look after everyone around you and to see people rise around you, but you're in a bit of a shitty culture, what is that? What do you do?
A
So, for the. So, I mean, kind of talking about middle management, I mean, middle management's the most difficult job in a company for so many reasons. One, we don't train people how to lead. We just, you know, like, oh, you're good at your job now. You're a leader. You're a manager. Congratulations. Right? And my friend Bob Chapman, you know, he's right about this, which is we should stop using the term manager. Nobody wakes up in the morning to be managed. Nobody wants to be managed. We want to be led. Be my leader, not my manager. Right? You can't lead a company. You can run a company, but you can only lead people. Being a leader is a relationship. So what people get wrong is they think they're a leader when they've been anointed with a title or a rank. All that means is you've achieved some level of accomplishment and somebody has sought fit to. To bring you up in the ranks. You may or may not be a good leader, but you fit whatever promotion standard the company has set. Leadership is a choice. First and foremost, being a parent. You're technically a parent if you have a child, but you become a parent when you raise a child. So, yeah, the biggest mistake people make is you're not a leader simply because you have a rank or a title. Leadership is a choice, and it's a lot of work. It's the choice to see another person rise and grow and that you're gonna be a part of that journey.
B
Do you think that. And have you seen in your past horrible leaders that actually can change their style of leadership and become. Because I'm sure that there are so many people here that work for what they would consider a manager and not a leader?
A
Yeah.
B
So what do you do in that? Physician.
A
So, again, one of the core principles of being a good leader is empathy. So let us not assume that because somebody's a bad leader that they're a bad person. I went for a walk with a friend of mine. She goes, I need your advice. I said, go ahead. She goes, my boss is a horrible person. She's a horrible person. I said, oh, my God. Does she. Does she abuse her. Her dog? She goes, what? I said, did she come home and kick the dog? She goes, no. I'm like, is she. Is she a horrible mother? She goes, no. I said, okay, so we don't know that she's a horrible person. She might be, but we don't know.
B
That she's so frustrated.
A
All we know. All we know is she's a horrible person.
B
She's like, she's horrible. Okay?
A
All we know is that she's a horrible leader. That's all we know, right? And maybe she's a horrible leader because she's had terrible role models that the people who. She. Who got promoted in front of her stabbed people in the back. So she followed them, and it kept working. So maybe she had bad role models. Maybe she had a bad incentive structure at the company she worked for. Maybe she's painfully insecure. Maybe she's responding incredibly badly to the insane amount of pressure that's on her from up above, which we have no idea. We don't know if somebody's yelling at her because of the stock price. We don't know. All we know is that she's showing up badly. So the part of it is like, yeah, we work for some bad leaders, but they're not necessarily bad people. And that's a huge distinction. Because by recognizing someone's a bad leader, I can say, okay, they haven't learned. They're under pressure. They're peter. Principled out. They shouldn't have the job. They're insecure. They're afraid. Okay, I'm going to adjust the way I speak because I know that I'm going to adjust the way I interact with them because I know that I'm going to give some grace, because I know that. And what you are doing is becoming the leader you wish you had. That's what's happening.
B
Exactly. What do you say to people in a position of leadership? That if you were to give three simple things to become a better leader, what should you do?
A
I'll answer the question.
B
Go on.
A
But it comes.
B
Why do you laugh? I want to know why you laugh.
A
What are the three simple things that I have to do to be healthy? I wish I could tell you that I know you need to exercise. I know you need to.
B
I know you got to go to sleep. You Got to eat well, you got to exercise.
A
But those are not three simple things. Those are three monumental things.
B
They are monumental.
A
Tell me three monumental things that I have to do to be a better leader.
B
Tell me. Give me the free monumental.
A
Sure, I can give you those things.
B
You need to do.
A
Three monumental things you have to do to be a better leader. In no particular order, all of them are about human skills, okay? Because remember, we've learned hard skills to do our jobs. What we've been neglecting are the human skills I need to be. And being a leader is a human enterprise. You're responsible for the lives of other human beings, which means you have to be a better listener. And I don't mean hearing words, listening for meaning, listening for feelings, active listening. If you're really good at active listening, at the end of it, you're exhausted because it's really hard to be present and put your own attention aside for a second, your own opinions aside, to learn what somebody else is going through. So active listening is a huge one. Another one is you have to be a student of leadership. Every parent reads books about parenting, reads articles about parenting, talks to their other friends who are parents, and talks to their own parents about how to be a parent. You are a constant student of the thing you're trying to be, right? So you have to elect to be a student of leadership. You have to read the books, you have to read the articles, you have to watch the talks. You have to have conversations about it constantly. I go out with friends who are unbelievable. They've done amazing things, they held amazing positions. You know what? We talk about leadership. We talk about the struggles we have, the politics and the difficulty and the person. We compare notes. We give each other ideas constantly. I write books on leadership, and I still consider myself a student of leadership. I am not an expert. I'm a student, right? So number one.
B
Well, you have to be. Because the people you're leading are always changing.
A
And everyone's different.
B
They're always changing.
A
And challenges are different, and culture is different and politics are different, and generations are different.
B
Generations are different and generations are different.
A
And generations are different. And if you're leading based on what you learned 20 years ago, you're out.
B
You're out, you're out. Forget about it.
A
It's like you kids in your rock and roll. It's like you're done, it's over.
B
Of course, there's nothing like running a company for 20 years.
A
No, it's all. All the rules are changing now. The basic human principles are the Same people want to know that they matter. People want to know that their work matters. People want to know that they're valued and valuable. People want to feel trusted and trusting. People want to feel seen, heard and understood. Those things are universal across cultures, cross generations. Nothing has changed there. So the things that I'm telling you about, listening, I'm talking about being the student because you have to keep up to date on all the things. And then the third one is pretty much everything else. You heard what I just said, which is people want to feel like they matter and their work matters. People want to feel like they're trusted and trusting. People want to feel seen, heard and understood. Do you have the skills to do those things? Listening, empathy, how to resolve conflict, how to have difficult conversations, how to do recognition and reward. It's not simply by just giving people bonuses. Right. And so do all those things that make people feel seen, heard and understood like they matter. You're on your. You're doing great. To being a leader or a friend.
B
Or a parent or just a good person.
A
Or a good person. Like. And the reason these things I say.
B
Simple because again, a lot of those things would come so naturally.
A
Simple but not easy. To me, simple but not easy.
B
You know, it's just.
A
Yeah, simple but not easy.
B
Do you think that there are born leaders like that? People are just born that way and they're going to be excellent leaders?
A
No.
B
Why not?
A
No. It goes back to the why. It's how they were raised. Some of them seem to be born leaders because they were lucky enough to have a coach or a parent or an experience when they were young. Or hardship that they had to learn to cope with that gave them those skills at a much earlier age than the rest of us. And they show up a little later on and you're like, whoa, born leader. Not born leader. Mahatma Gandhi was a failed lawyer in the UK who failed the bar. Okay. He was working to be a lawyer.
B
No idea.
A
Was working to be a lawyer. And he moved to South Africa because I think. I don't remember. It was easier, right? Became a lawyer there, saw the injustices and the racism there, and it changed him. It gave him an opportunity to be the leader he didn't think he was going to be. You go look at early videos of Steve Jobs, this remarkable orator, this remarkable leader. He's bumbling, he's fumbling, he's useless, he's insecure, he's self doubting. There's some videos on YouTube of him doing early interviews.
B
I've seen him.
A
And they happen to have the camera rolling before the camera. And he literally feels sick. He says, I feel sick. I think I have to go throw up, you know?
B
Oh, shit. That's crazy.
A
He learned it.
B
Yeah, he learned it.
A
He got the reps. He got the reps. It's like the first day of the gym, you're a week and it hurts. And you don't want to go back. And you can't walk for two days because you did legs. And you're like, I can't even work out because my muscles don't work. And once the pain goes away for whatever stupid reason, you go back and then you do it again and it hurts. And you're embarrassed because you've got these rinky dink little weights and everybody's looking at you as they're lifting big weights. And so you're humiliated. And you go back and you look in the mirror and you don't like what you see, and you go back, and all of the empirical evidence is telling you, so, stop, stop. You're humiliated. You're weak. It hurts. And you go back. That's why they're made and not born, is they keep going back over and over again. But why would they keep going back? It's because they believe that it's worth it. And this is where purpose and cause comes in, which is, there's something bigger than me that I think is worth it. It's bigger than me. I think it's worth going back over and over again. The pain has to feel worth it.
B
So what question do you wish business leaders would ask themselves more?
A
What question do I wish business leaders would ask themselves more?
B
They rarely do.
A
Yeah, what more can I learn?
B
What more can I learn?
A
You know, I'm very cynical of the business leaders who say, I think I know what I'm doing. And I'm like, okay, not gonna work out.
B
No. I feel like in general, in every part of our lives, you have to constantly be in learning mode. Like, you're never done.
A
And here's the problem with what more can I learn? Here's the problem with the question. It's a loaded question, right? Which is I don't know. Which means I have to be curious, which means I have to get 360 reviews for somebody to show me my blind spots because I don't know what I don't know.
B
You still seek those out even now?
A
Oh, my God, yes. Oh, my God, yes. And I have recurring ones which are the really frustrating ones. I'm like, I know. I knew it. And I did it again, you know.
B
For sure, because even you, you're never done learning about this. Well, even you that's written, like three bestselling books about this and speak so beautifully and articulately about it. And somebody that we all sit here and tune in to listen to, like, even you, doesn't have it totally down 100% correct.
A
All I'm doing is running my race. And instead of having the pain and frustration and lessons and realizations in my mind, I'm broadcasting them. Okay, this hurts right now at this point of this mile. Oh, I learned. Here's a technique that helps you get through the pain at mile 12. That's all I'm doing.
B
If you said it like that, we'd all know.
A
It's just because it's. I'm just. I'm simply writing books authority.
B
I mean, we were all like, okay, write it down.
A
I mean, you know, it works. Simon said, you know, strong opinions, loosely held. But, I mean, I'm in the race, too. I'm not on the sidelines. I don't have it all figured out.
B
He's part of the. Your allure that we are very, very clear that we are. That we're learning with you, that you are talking to us in a way where you're not the know it all good. It's like you. You're coming to us with the problems and with the scenarios and the situations. And I think that people do want to unlearn, you know, bad habits, toxic behaviors. People do sit in their organizations and say, okay, I'm here. What do I do next? And that's why I've loved following you for so long. Do you think that you can undo a toxic culture? If somebody is. If a leader has a team in a toxic culture, what do they start to do? They start to ask themselves questions like, should I be in this company? Should I just quit? Can I undo it? Is it worth my time? What do you say to people?
A
Make the implicit explicit. Take the thing that everybody knows to be true and put it on the table. And I've done it in my organization as the leader. But you can do it at any level, right? Which is, hey, folks, this is not a fun place to work. I'm not enjoying it, and I can't believe I'm the only one. I know that we are gossipy. That's not good. I know that we don't trust each other. That's not good. I know some things that we could probably do to make it better. I don't know where to start, but I do know that it's not good for us. And nobody wants to work in a place like this. So we have a couple choices. We can ignore it and just chip away at it and be passive aggressive, or we can raise our hands and say, you know what, I got to work here. Might as well try and make it a bit better. That's it. I'm not asking anything, I'm not telling anything. I'm just making the implicit explanation. I'm just saying how I feel.
B
What happens when you do that, Simon?
A
So there's a few things that happen. Don't expect immediate results. Number one, right? What it does is it makes weirdly people feel seen and heard, right? Because people will say, be like, you're right. I feel that about this place too. Okay, now you have a partner in camaraderie and potential supporter, right? Not everybody's going to want to help because some of them benefit from that culture. They know how to work those politics. So they're gonna be resistant. That's gonna happen too. They might double down on difficult. Right? That'll happen too. But if you get a critical mass of people, like, let's do it for each other. Yeah.
B
Cause there's always people that say, that doesn't exist here.
A
That doesn't exist. You silence the bullies. But making the implicit explicit is a very difficult and very powerful tool. Difficult because it's. Nobody wants to say it. No leader wants to admit that their culture's crap in front of everybody.
B
No. Cause that's you putting your hands up, saying, I've fucked up here, I've done something wrong to get us into this situation.
A
And that's the other part.
B
And I need you lot.
A
But that's the other part, which is accountability. You make this culture awful. No, no, no, no. I recognize I'm a part of the problem here.
B
I'm a part of it.
A
And I recognize I've done made many mistakes and I'm on my own journey. But at the end. But it's like a personal relationship, right? Which is when you're, you know, you know this from. If you have a successful romantic relationship or even a successful friendship, you know, when you have a fight, it can't be me versus you.
B
Never.
A
It has to be you and me versus the problem. And it takes the leader, and it can be either one at any time to sometimes have the self awareness in the moment of anger and heat to interrupt what's happening. And I remember I was fighting with my girlfriend. This is how the Fight went, here's what I did right, and here's what you did wrong. And her response was, here's what I did right, and here's what you did wrong.
B
Now, that can go on for a while.
A
And this was going on for a while, and I realized this was going nowhere, and I realized we were trying to be right and make the other person wrong. Fortunately, in that moment, at the wherewithal to interrupt and say, this is not gonna work. I need to change the rules of this fight. And I said, here are the new rules of the fight. I'm gonna tell you what I did wrong, and I'm gonna tell you what you did right. I'll go first. And I said, here's what I got wrong, and here's what you got right. And she goes, yeah, well, here's what I got wrong, and here's what you got right. And in 30 seconds, we realize we're both trying to.
B
Yeah.
A
And it was us versus the problem. But the leader is the. We call you leader not because you're at the top. We call you leader because you went first. First towards the unknown and first towards the danger. The first person to say this is this. This not. This place sucks to work. No, no, no, no. This place can be a better place.
B
To work a million percent, right? But also, you have to be the first to rise up, right? The first one that comes up above the fray and says, here's what I'm seeing. Are you feeling too.
A
And here's how I feel.
B
Are you feeling what I'm feeling right now? And can we all get on?
A
And I'm not making anybody wrong. I'm not making anybody wrong.
B
Just is what it is, right?
A
It is what it is. I'm gonna tell you how I feel because my feelings are always valid. You can disagree with me if I make conclusions. And so the leader isn't the person who's in charge. The leader is the person with the courage to go first into the unknown, into the danger, the first to put their neck out to protect everybody else. We call you leader because you went first.
B
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A
Easy, easy, easy. It's courage. And I think you can't have courage without integrity. I think those two are inextricably linked. I think courage and integrity the courage to speak truth, to power. The courage to be honest about my own failings. The courage to make the implicit explicit. The courage to change. The courage to change the rules of the argument so that it's you and me versus the problem, not me versus you. The courage to change the narrative when we label a colleague lazy, stupid, arrogant and say, well, maybe they're just insecure, or maybe they're struggling, or maybe we put them in the wrong job, or maybe they don't know the rules like they could be stupid, lazy or arrogant. But there could be other things, too. The courage to do all those things and the integrity. Courage takes integrity and integrity takes courage. You can't separate the two. I don't think you can have one without the other. I don't know which one comes first, but I know that when you practice one, you get the other. When you practice courage, you get integrity. When you get integrity, you get courage.
B
So you just gotta practice and you get.
A
Yeah, and courage without integrity is bluster, foolhardy, pigheaded. It can be mistaken for courage. Because real courage. Real courage, like I said to me, real courage is the willingness to run towards danger, to protect others.
B
Well, and also there is that piece just going back to what you said about vulnerability, Right. Because you have to be vulnerable and be willing to see, or be willing for other people to see your vulnerability to be truly courageous.
A
It's also to be believed. If you present yourself as perfect all the time and having all the answers, it backfires. One, nobody believes you because nobody has all the answers and knows everything. That's number one. Number two, you make other people feel insecure because they don't have all the answers and they don't have any and they have doubts. So they see you always confident and always with the answer. So, oh my God, it must be me. So the ones with a lot of self confidence will not believe you. And the ones that have any cracks in their self confidence, their insecurities will exaggerate. And so if you pretend to know all the answers, it may be the single biggest mistake that leaders make, which is I have to know all the answers and I have to present confidence at every moment. That's how I have my credibility.
B
That's the single biggest mistake, I think.
A
So the opposite is true. You get more credibility to be like, look, here's a huge fricking problem and I have no clue what it's start. And I think people mistake being vulnerable with not having confidence. Because vulnerable sounds weak. That's why I like the term available. It doesn't sound weak. Right?
B
Yeah. I guess in a corporate culture you'd much rather use available. Well, this is something I'm fascinated about by you because you've orientated your life around this idea of optimism now, right? You have the podcast, you have your company. Like, what does that actually backpack?
A
The coffee? I have. I have the press. I have a publishing house. You have your own imprint. My own imprint.
B
Which is incredible.
A
Yeah. Optimism Press. Thank you. Optimism Press, which is in partnership with Penguin Random.
B
Well, you can tell me a little bit about that? Like, why optimism right now?
A
Oh, really?
B
Yeah. No, I wouldn't. Because, listen, I can sit here and make up my own reasons. I want to hear it from you.
A
I love it when people say to me, simon, in these times, optimism, like, yes. Do you want me to have optimism when everybody's feeling great? I mean, like, what? No. Optimism is important all the time. And I think you're right. You started this podcast by saying we are living in a period right now where there is a distinct lack of optimism. I think that's 100% true. Okay. Why is there a distinct lack of optimism? We talk about the rising epidemic of insecurity and loneliness and anxiety and depression and in the worst cases, suicide. Those are all a lack of optimism too. I would argue that the reason we're suffering a lack of optimism is because we have no sense of belonging to. And you can see people desperately looking for something. You see it in the politics. On the left, it might be sort of Palestine or anti Israel. On the right, it might be anti vax or anti mask or whatever the thing is. And they're grasping onto anything that gives them a sense of cause or belonging. And it has all the trappings of it. It feels like it. You have community camaraderie. You're around people, they're all rah, rah. We all have each other's backs.
B
We're together.
A
We're together. But for the fact that we don't know where you're going. We don't know what you stand for. I know what you stand against, definitely know that. But I don't know what you stand for. And if you get your way, then what? If you get your way, where are you going? What's the vision? What's the world you're trying to build? Right. And so I have no problem with articulating something that's standing in the way of my vision. But when you label an enemy or an anti with no sense of vision, it has the feelings of belonging, but it's not belonging because it'll go away. And then you'll have to grasp onto something else. And the next thing, and the next thing, and we're seeing it happen.
B
That's it.
A
We're seeing it happen on the left, we're seeing it happen on the right. We've changed what the cancel culture looks like. And then we're all in on the next thing. We're all in on that until we're all in on the next thing. Because if you truly have purpose and cause it's your whole, whole life for that one thing that you believe in. And it's not the thing you're against, it's the thing you're for. It's the. I imagine a world. I have a dream. I believe.
B
What do you believe?
A
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. That is the world that I imagine. There are many things standing in the way. Existing business practices, old fashioned leadership styles, the way that we run our company, shareholder supremacy, short termism. These things are standing in the way of the vision that I have, which is why I've committed myself to one of the things we have to overcome, which is the leadership challenge and the way we build corporate culture. I want people to feel happy at work. It's a Trojan horse, right? The reason I picked work is because that's where all the people are. During the Great depression, there was 25% unemployment. What I hear is 75% still have a job. If you want to get people, get them at work. So if I can teach people the human skills of listening and empathy and how to resolve conflict and how to have difficult conversations and how to see each other as human and how to change narratives, and I can teach all that at work. Why? Because it makes work better and it makes corporate culture better and it makes all those things better and you make more money. Blah, blah, blah, Great. And then you go home and you know how to talk to your kids better. You know how to listen to your spouse better. You know how to deal with stress better. You know how to talk to your neighbors. You know to have difficult conversations at the Thanksgiving table with your crazy uncle who you disagree with, but it doesn't trigger anybody. And you know how to keep peace and you know how to make people feel seen and heard and understood and the world gets better. It is a Trojan horse. All of my books, I'm a philosopher. I write philosophy books cleverly disguised as business books. But at the end of the day, what I care most about is the human relationship. And so why? Optimism. It's the core of a successful human relationship. The reason I work hard in this I talk to my favorite couples, like the romantic couples that I see who I envy. I want a relationship like theirs. And I have a small list. I know who they are. I ask them, what's your secret? They all say the same thing. It's hard work and we do the work. Why is that? The Recipe for successful relationships. Because human relationships are hard and cats are naturally good at being cats. They don't have to study. Unfortunately, being human, we're not naturally good at it. We're actually naturally pretty crappy at it.
B
You have to work at it, right?
A
Being a good human and being a good partner and being a good colleague and being a good leader and being a good follower, it all takes work. And the question is, are you willing to do the work? The only reason you're willing to do the work is because it's worth it. It has to feel worth it. And so when you're in a romantic relationship with a person you love and who loves you, why is it worth doing the work? Because this person matters to me. I matter to this person. This person makes me feel seen and heard. I get the honor of helping them feel seen and heard. I feel like I matter. I get the honor of making helping them feel like they matter. I'm growing as a person. I get the honor of helping them grow. I'm going to keep doing it. And the minute you say it's not worth it anymore, then. Then have that conversation. Question the relationship, question the job, question the collegial relationship, question the friendship. Absolutely. Have those conversations. Have that feedback session. We have feedback sessions at work. Why don't we have feedback sessions with our friends? When our marriages are in trouble, when our romantic relationship is in trouble, we get couples therapy. How come we don't get friends therapy? How come we're not working hard to.
B
Make our relationship pursuit around friendship? Yeah, much needed.
A
But it's all comes down to human relationship. I have a clear vision of where I want to go. I can see the things standing in the way. And I'm in pursuit of something noble and good for all people. Not for some people, but for all people. For as many people as want it. That's why I said vast majority. I'm not so foolhardy that I can think. I can help everyone. Right?
B
Thank you, Simon. I love speaking to you and you ended just on the perfect note. Okay, so a couple of rapid fire questions for you, Simon. An easy one. What's the first thing you do when you wake up?
A
I do the crossword puzzle.
B
That's so old school and lovely. In a newspaper or on an iPad.
A
On my phone.
B
On your phone. Okay. What's the last thing you do before you go to bed at night?
A
The crossword puzzle.
B
Really?
A
If it's a Friday. Yeah. If it's a Monday, I'm done in 10 minutes on a, you know, I'm done in 10 minutes in the morning. But I forgot, to be honest. I don't really meditate in the traditional way, but I like making my brain think a little bit at the beginning and the end of the day. And I'm not on text, and I don't care what's happening in the world. It's just a way for me to just disconnect and focus. And it's your meditation. It's a source of meditation almost every day.
B
You find it hard to meditate?
A
No, I like meditation.
B
You like meditation. Okay, just checking. What's a book that changed your life? Start with Why? I mean, that was a pretty good one for you.
A
I mean, yeah, I haven't read a full book that changed my life, but there are pieces of books that have changed my life. Man's Search for Meaning, obviously. And Finite and Infinite Games by Jim Carse, who put me on the path to write my book, the Infinite Game. I was so inspired by his truth that I wanted to build on it. It's a funny question, like, what book changed my life? Yeah, the writing of Start with why definitely changed my life. 100%.
B
Yeah, that's a big, perfectly good answer.
A
Yeah, it's funny.
B
What are you currently aspiring to in your life professionally?
A
I want to really. There's multiple things. You know, I'm looking for all the ways to bring the vision to life in new ways. And. And the businesses that I'm building are my way of asking for help. Right? So I'm building this. This training company called Y School, where we're teaching personal coaches, executive coaches, learning and development people, and companies to help individuals find their why. I'm asking for help to get as many people to help learn their why as possible, because I can't do it alone. So if I build a company that gives that exact way, I do it to other people. Holy cow. Right? The app that we're building right now is my way of saying, I have this vision of the world as it could be, but I can't do the work. I need you to be the leaders in the companies. I need you guys to help me. I need to build an army. I'll teach you some skills. I'll give you some guidance. And so all of our whole learning platform on our website is designed to give people those human skills so that they can join me to change the world into one that could be. I need people to go change their companies. I can't do it for them. I need people in the race with me. So I'm trying to train people to practice running and get in the race with me. So that's happening. The friendship book that I'm writing is because we underestimate the importance of friends in our lives. And if you want to have a successful romantic relationship and you want to have a successful career, you better have some good friends who love you and care about you. And the thing is, there's so much written about leadership. There's an entire industry about leadership. There's an entire industry about romance and finding partners, and yet there is so little about how to be a friend. And so I'm trying to start that industry. I want lots of books about friendship. I want lots of apps and lots of companies about friendship.
B
You are so right. How have I never read a book about friends?
A
Because there's barely anything on the topic. And if you ask people, are you a good friend? Most people say yes. And if you peel the onion just one layer, most of us are pretty shitty friends. Most of us. Like, would you cancel in a friend for a meeting or would you cancel in a meeting for a friend? Oh, but my friend would understand. Okay, so do you get a divorce after one bad fight with your spouse? No, of course not. You work through it. Would you end a friendship after one bad fight? I've done that shit. Whoops. You know, and for some reason, we have a lower standard for our friends. And yet, if you want to have a successful career and you want to have a successful romantic relationship, those things come and go. Your friends are the only stable thing through all of it. You better look after your friends and learn how to be a good friend and learn how to serve your friends by giving them the honor to serve you.
B
We're waiting for this next book.
A
So all of my work, our company, our training program, all of it, all of it is me asking people, inviting people to join me in common cause as we learn to build this world that feels inspired, safe, and fulfilled.
B
It's amazing. All right, I have one last question for you. What is something that you valued when you were starting out that you no longer value?
A
I don't need to be right anymore. I don't need to be the one who is right. I'm okay if somebody else's is right and they have a better solution, better answer, I'll do what they said. I don't need to be a hero. I don't need to be right. I don't need to be in charge. I don't need any of those things. As long as we have momentum and the work's getting done. I'll lead, I'll follow. I don't care. I'll follow your idea, Follow my idea, I don't care. As long as it moves us in the common direction I'm in.
B
Fantastic. Thank you so much Simon.
A
Thanks for having me.
B
What a pleasure. If you're loving this podcast, be sure to click Follow on your favorite listening platform. While you're there, give us a review and a five star rating and share an episode you loved with few a friend who'd be so grateful? Aspire with Emma Greed is presented by Audacy. I'm your host, Emma Greed. Our executive producers are Corrine Gilliatt Fisher, Derek Brown and me. Our executive producers from Audacy are Maddy Sprung Kaiser, Leah Reese Dennis, Asha Saluda, Lauren Legrasso and Jenna Weiss Berman. Stephen Key is our senior producer. Sound design and engineering by Bill Schultz. Angela Peluso is our booker. Original music by Charles Black Video production by Evan Cox, Kirk Courtney, Andrew Steele, Carlos Delgado and Arnie Agassi. Social media by Olivia Homan Special thanks to Brittany Smith, Sydney Ford, My teams at the lead company and WME Maura Curran, Josephina Francis, Hilary Schuff, Eric Donnelly, Kate Hutchinson, Rose, Tim Meikol, Sean Cherry and Lauren Vieira. If you have questions for me, you can DM me at Aspire with Emma Greed. Greed is spelled G R E D e. That's Aspire A S P I R E with Emma Greed. Or you can submit a question to me on my website emagreed me.
Episode Summary: Simon Sinek: Don’t Be a Toxic Leader
Date: January 27, 2026
Host: Emma Grede | Guest: Simon Sinek
Simon Sinek joins Emma Grede for a deeply insightful conversation on “why” — the purpose that underpins success, leadership, and fulfillment. The episode explores finding personal and organizational purpose, the biology behind decision-making, practical strategies for self-alignment, the true essence of leadership, and fostering cultures of service over self. The tone is authentic, lively, and self-reflective, with both Simon and Emma sharing personal anecdotes, challenges, and actionable exercises.
[03:03] Simon Sinek’s Central Principle:
“People don’t buy what you do, they buy why you do it. …It’s a biologically true statement.”
— Simon Sinek (03:03)
[07:44] The Celery Test:
“If you know your why is to always be healthy…you buy the celery. And everyone can see that you only have celery and rice milk. …You just attracted a customer or an employee simply by making decisions because what you do reflects what you believe.”
— Simon Sinek (07:44)
[12:42] The Friends Test:
“Ask your best friend: Why are we friends? …Eventually they’ll give up describing you and start describing themselves. …What they put into words was the value I have in their life, the space that I fill.”
— Simon Sinek (12:42)
[15:41] On Living Your Why & Deciding When to Change Jobs
[29:30] Using Reminders for Self-Alignment:
“I wear an orange strap on my watch… the word inspire embroidered in some of my clothes. …It’s not for you, it’s for me. …I’ve chosen orange. I’ve chosen the word optimism as a reminder to me of my job to help me stay in balance.”
— Simon Sinek (29:30)
[56:35] Defining Leadership:
“Most people think being the leader is being in charge. Incorrect. Being a leader means you take care of those in your charge.”
— Simon Sinek (56:35)
[57:54] On Bad Cultures & Middle Management:
“Middle management’s the most difficult job. …We don’t train people how to lead, we just, oh, you’re good at your job, now you’re a manager. …Nobody wakes up to be managed. We want to be led.”
— Simon Sinek (57:54)
[63:53] Three Monumental Things for Better Leadership:
Notable Quote:
“People want to feel seen, heard and understood like they matter. You're doing great to being a leader or a friend.”
— Simon Sinek (64:38)
[40:05] “Help Others” over “Self-Help:”
“We’re obsessed with helping ourselves, and I would like us to see obsess more with helping others.”
— Simon Sinek (40:05)
“Giving someone the opportunity to serve, right, is an act of service.”
— Simon Sinek (43:15)
[51:20] Everyday Service:
“Service is uncomfortably simple. …It’s worrying about the person to the left and the person to the right.”
— Simon Sinek (50:21)
[19:21]
“Authenticity means I say and do the things I actually believe. …Their idea of authenticity is like crying on camera. You know, that’s not authenticity.”
— Simon Sinek (19:21)
[76:38]
“It’s courage. And I think you can’t have courage without integrity. …The courage to make the implicit explicit. The courage to change the narrative... The courage to do all those things and the integrity. …I don’t think you can have one without the other.”
— Simon Sinek (76:38)
Simon Sinek’s approach and wisdom can help anyone—leader or otherwise—find direction, foster meaningful relationships, and become a force for positive change in any context.