The following is a conversation with Simon Sinek, author of several books, including "Start With Why," "Leaders Eat Last," and his latest, "The Infinite Game." He's one of the best communicators of what it takes to be a good leader, to inspire, and to build businesses that solve big, difficult challenges.

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So from my perspective of artificial intelligence and game theory in general, I'm a huge fan of. Finite games, from the broad philosophical sense, is something that in the robotics, artificial intelligence space, we know how to deal with. And then you describe the infinite game, which has no exact static rules, has no well-defined static objective, the players are known, unknown, they change, there's a dynamic element.

So this is something that applies to business, politics, life itself. So can you try to articulate the objective function here of the infinite game, or in the cliche, broad philosophical sense, what is the meaning of life? (Simon laughs) - Go for the start with the softballs. - Yep, easy question first.

- So James Kars was the philosopher who originally articulated this concept of finite and infinite games. And when I learned about it, it really challenged my view of how the world works, right? Because I think we all think about winning and being the best and being number one. But if you think about it, only in a finite game can that exist, a game that has fixed rules, agreed upon objectives, and known players like football or baseball.

There's always a beginning, middle and end. And if there's a winner, there has to be a loser. Infinite games, as Kars describes them, as you said, have known and unknown players, which means anyone can join. It has a changeable rules, which means you can play however you want. And the objective is to perpetuate the game, to stay in the game as long as possible.

In other words, there's no such thing as being number one or winning in a game that has no finish line. And what I learned is that when we try to win in a game that has no finish line, we try and be number, we try and be the best in a game that has no agreed upon objectives or agreed upon metrics or timeframes.

There's a few consistent and predictable outcomes. The decline of trust, the decline of cooperation, the decline of innovation. And I find this fascinating because so many of the ways that we run most organizations is with a finite mindset. - So trying to reduce the beautiful, complex thing that is life or what politics or business into something very narrow.

And in that process, the reductionist process, you lose something fundamental that makes the whole thing work in the longterm. So returning, I'm not going to let you off the hook easy. What is the meaning of life? So what is the objective function that is worthwhile to pursue? - Well, if you think about our tombstones, right?

They have the date we were born and the date we died. But really it's what we do with the gap in between. There's a poem called "The Dash." You know, it's the dash that matters. It's what we do between the time we're born and the time we die that gives our life meaning.

And if we live our lives with a finite mindset, which means to accumulate more power or money than anybody else, to outdo everyone else, to be number one, to be the best, we don't take any of us with us. We don't take any of it with us. We just die.

The people who get remembered, the way we want to be remembered is what kind of people we were, right? Devoted mother, loving father, what kind of person we were to other people. Jack Welch just died recently. And the Washington Post, when it wrote the headline for his obit, it wrote, "He pleased Wall Street and distressed employees." And that's his legacy.

A finite player who is obsessed with winning, who leaves behind a legacy of short-term gains for a few and distress for many. That's his legacy. And every single one of us gets the choice of the kind of legacy we want to have. Do we want to be remembered for our contributions or our detractions?

To live with a finite mindset, to live a career with a finite mindset, to be number one, be the best, be the most famous, you live a life like Jack Welch. To live a life of service, to see those around us rise, to contribute to our communities, to our organizations, to leave them in better shape than we found them, that's the kind of legacy most of us would like to have.

- So day-to-day, when you think about what is the fundamental goals, dreams, motivations of an infinite game, of seeing your life, your career as an infinite game, what does that look like? - I mean, I guess I'm sort of trying to stick on this personal ego, personal drive, the thing that, the fire, the reason we want to wake up in the morning and the reason we can't go to bed because we're so excited, what is that?

- So for me, it's about having a just cause. It's about a vision that's bigger than me, that my work gets to contribute to something larger than myself. That's what drives me every day. I wake up every morning with a vision of a world that does not yet exist, a world in which the vast majority of people wake up every single morning inspired, feel safe at work and return home fulfilled at the end of the day.

It is not the world we live in. And so that we still have work to do is the thing that drives me. I know what my underlying values are. I wake up to inspire people to do the things that inspire them. And these are the things that, these are the things that I, these are my go-tos, my touch points that inspire me to keep working.

I think of a career like an iceberg. If you have a vision for something, you're the only one who can see the iceberg underneath the ocean. But if you start working at it, a little bit shows up. And now a few other people can see what you imagine, be like, oh, right, yeah, no, I wanna help build that as well.

And if you have a lot of success, then you have a lot of iceberg and people can see this huge iceberg and they say, you've accomplished so much. But what I see is all the work still yet to be done. Yet I still see the huge iceberg underneath the ocean.

- And so the growth, you talk about momentum. So the incremental revealing of the iceberg is what drives you. - Well, it necessarily is incremental. What drives me is that, is the realization, is realizing the iceberg, bringing more of the iceberg from the unknown to the known, bringing more of the vision from the imagination to reality.

- And you have this fundamental vision of optimism. You call yourself an optimist. I mean, in this world, I have a sort of, I see myself a little bit as the main character from "The Idiot" by Dostoevsky, who is also kind of seen by society as a fool because he was optimistic.

So one, can you maybe articulate where that sense of optimism comes from and maybe also try to articulate your vision of the future where people are inspired, where optimism drives us? It's easy to forget that when you look at social media and so on, where toxicity and negativity can often get more likes, that optimism has a sort of a beauty to it.

And I do hope it's out there. So can you try to articulate that vision? - Yeah, so, I mean, for me, optimism and being an optimist is just seeing the silver lining in every cloud. Even in tragedy, it brings people together. And the question is, can we see that?

Can you see the beauty that is in everything? I don't think optimism is foolishness. I don't think optimism is blindness, though it probably involves some naivete, the belief that things will get better, the belief that we tend towards the good, even in times of struggle or bad. You can't sustain war, but you can sustain peace.

I think things that are stable are more sustainable, things that are optimistic are more sustainable than things that are chaotic. - So you see people as fundamentally good. I mean, some people may disagree that you can't sustain peace, you can't sustain war. - I mean, you don't have to, I think war is costly.

It involves life and money, and peace does not involve those things. It requires work. I'm not saying it doesn't require work, but it doesn't drain resources, I think, the same way that war does. - The people that would say that we will always have war, and I just talked to the historian of Stalin, would say that conflict and the desire for power and conflict is central to human nature.

- I concur. - But something in your words also, perhaps it's the naive aspect that I also share, is that you have an optimism that people are fundamentally good. - I'm an idealist, and I think idealism is good. I'm not a fool to believe that the ideals that I imagine can come true.

Of course, there'll never be world peace, but shouldn't we die trying? You know, I think that's the whole point. That's the whole point of vision. Vision should be idealistic, and it should be, for all practical purposes, impossible. But that doesn't mean we shouldn't try, and it's the milestones that we reach that take us closer to that ideal that make us feel that our life and our work have meaning, and we're contributing to something bigger than ourselves.

You know, just because it's impossible doesn't mean we shouldn't try. As I said, we're still moving the ball down the field. We're still making progress. Things are still getting better, even if we never get to that ideal state. So I think idealism is a good thing. - You know, in the word infinite game, one of the beautiful and tragic aspects of life, human life at least, at least from the biological perspective, is that it ends.

So sadly-- - To some people, yeah. - Fine, it's tragic to some people, or is it ends? - I think some people believe that it ends on the day you die, and some people think it continues on. - And there's a lot of different ways to think what continues on even looks like.

But let me drag it back to the personal. - Sure. - Which is, how do you think about your own mortality? Are you afraid of death? How do you think about your own death? - I definitely haven't accomplished everything I wanna contribute to. I would like more time on this earth to keep working towards that vision.

- Do you think about the fact that it ends for you? Are you cognizant of-- - Of course I'm cognizant of it. I mean, aren't we all? I don't dwell on it. I'm aware of it. I know that my life is finite, and I know that I have a certain amount of time left on this planet, and I'd like to make that time be valuable.

- Some people would think that ideas kind of allow you to have a certain kind of immortality. Maybe to linger on this kind of question, so first to push back on the, you said that everyone's cognizant of their mortality. There's a guy named Ernest Becker who would disagree that you basically say that most of human cognition is created by us trying to create an illusion and try to hide from ourselves the fact that we're gonna die, to try to think that it's all gonna go on forever.

- But the fact that we know that it doesn't. - Yes, but this mix of denial. I mean, I think the book's called "Denial of Death." It's this constant denial that we're running away from. In fact, some would argue that the inspiration, the incredible ideas you've put out there, your TED Talk has been seen by millions and millions of people, right?

It's just you trying to desperately fight the fact that you are biologically mortal. Your creative genius comes from the fact that you're trying to create ideas that live on long past you. - Well, that's very nice of you. I mean, I would like my ideas to live on beyond me because I think that is a good test that those ideas have value in the lives of others.

I think that's a good test that others would continue to talk about or share the ideas long after I'm gone, I think is perhaps the greatest compliment one can get for one's own work. But I don't think it's my awareness of my mortality that drives me to do it.

It's my desire to contribute that drives me to do it. - It's the optimist vision. It's the pleasure and the fulfillment you get from inspiring others. It's as pure as that. Let me ask, listen, I'm rushing. I'm trying to get you-- - You're good, you're good. I'm enjoying it.

- Get you into these dark areas. - You're good, I'm enjoying it. - Is the ego tied up into it somehow? So your name is extremely well known. If your name wasn't attached to it, do you think you would act differently? - I mean, for years, I hated that my name was attached to it.

I had a rule for years that I wouldn't have my face on the front page of the website. I had a fight with the publisher because I didn't want my name big on the book. I wanted it tiny on the book 'cause I kept telling them it's not about me, it's about the ideas.

They wanted to put my name on the top of my book. I refused. None of my books have my names on the top because I won't let them. They would like very much to put my name on the top of the book, but the idea has to be bigger than me.

I'm not bigger than the idea. - That's beautifully put. Do you think ego-- - But I also am aware that I've become, I've become recognized as the messenger. And even though I still think the message is bigger than me, I recognize that I have a responsibility as the messenger.

And whether I like it or not is irrelevant. I accept the responsibility. I am happy to do it. - I'm not sure how to phrase this, but there's a large part of the culture right now that emphasizes all the things that nobody disagrees with, which is health, sleep, diet, relaxation, meditation, vacation-- - That's true.

- Are really important. And there's no, you know, it's like, you can't really argue against that. In fact, people-- - Less sleep. - Less-- - I'm joking. - Yes, well, that's the thing. I often speak to the fact that passion and love for what you're doing and the two words hard work, especially in the engineering fields, are more important to prioritize than sleep.

Even though sleep is really important, your mind should be obsessed with the hard work, with the passion, and so on. And then I get some pushback, of course, from people. Would he make sense of that? Is that just me, the crazy Russian engineer, really pushing hard work? - Probably.

I think that's a short-term strategy. I think if you sacrifice your health for the work, at some point, it catches up with you. And at some point, it's like going, going, going, and you get sick. Your body will shut down for you if you refuse to take care of yourself.

You get sick, it's what happens. Sometimes, more severe illness than something that just slows you down. So I think taking, like getting sleep, I mean, there've been studies on this, that executives, for example, who get a full night's sleep and stop at a reasonable hour actually accomplish more, are more productive than people who work and burn the midnight oil because their brains are working better, because they're well-rested.

So, you know, working hard, yes, but wouldn't that work smart? I think that giving our minds and our bodies rest makes us more efficient. I think just driving, driving, driving, driving is a short-term strategy. - So but to push back on that a little bit, the annoying thing is you're like 100% right in terms of science, right?

But the thing is, it's because you're 100% right, that weak part of your mind uses that fact to convince you, like what, so, you know, I get all kinds of, my mind comes up with all kinds of excuses to try to convince me that I shouldn't be doing what I'm doing.

- To rationalize. - To rationalize. And so what I have a sense, I think what you said about executives and leaders is absolutely right, but there's the early days, the early days of madness and passion. - For sure. - Then I feel like emphasizing sleep, thinking about sleep as giving yourself a way out from the fact that those early days, especially, can be suffering.

- As long, it's not sustainable. You know, it's not sustainable. Sure, if you're investing all that energy in something at the beginning to get it up and running, then at some point you're gonna have to slow down or your body will slow you down for you. Like you can choose or your body can choose.

I mean. - So, okay, so you don't think, from my perspective, it feels like people have gotten a little bit soft, but you're saying no. - No, I think that there seems evidence that working harder and later have taken a back seat. I think we have to be careful with the broad generalizations but I think if you go into the workplace, there are people who would complain that more people now than before, you know, look at their watches and say, oops, five o'clock, goodbye, right?

Now, is that a problem with the people? You're saying it's the people giving themselves excuses and people don't work hard, or is it the organizations aren't giving them something to believe in, something to be passionate about? We can't manufacture passion. You can't just tell someone, be passionate. You know, that's not how it works.

Passion's an output, not an input. Like if I believe in something and I want to contribute all that energy to do it, we call that passion. You know, working hard for something we love is passion. Working hard for something we don't care about is called stress, but we're working hard either way.

So I think the organizations bear some accountability and our leaders bear some accountability, which is if they're not offering a sense of purpose, if they're not offering us a sense of cause, if they're not telling us that our work is worth more than simply the money it makes, then yeah, I'm gonna come at five o'clock because I don't really care about making you money.

Remember, we live in a world right now where a lot of people, rather a few people, are getting rich on the hard work of others. And so I think when people look up and say, well, why would I do that? If you're not gonna look after me and then you're gonna lay me off at the end of the year because you missed your arbitrary projections, you know, you're gonna lay me off because you missed your arbitrary projections, then why would I offer my hard work and loyalty to you?

So I don't think we can immediately blame people for going soft. I think we can blame leaders for their inability or failure to offer their people something bigger than making a product or making money. - Yeah, so that's brilliant. And start with why, leaders you last, your books. You kind of, you basically talk about what it takes to be a good leader.

And so some of the blame should go on the leader, but how much of it is on finding your passion? How much is it on the individual? And allowing yourself to pursue that passion, pushing yourself to your limits to really take concrete steps along your path towards that passion.

- Yeah, there's mutual responsibility. There's mutual accountability. I mean, we're responsible as individuals to find the organizations and find the leaders that inspire us. And organizations are responsible for maintaining that flame and giving people who believe what they believed, you know, a chance to contribute. - Sort of to linger on it, have you by chance seen the movie "Whiplash"?

- Yes. - Again, maybe I'm romanticizing suffering. Again. - It's the Russian in you. - It's the Russian. - Yeah, the Russians love suffering. - But for people who haven't seen, it's the movie "Whiplash" as a drum instructor that pushes the drum musician to his limits to bring out the best in him.

And there's a toxic nature to it. There's suffering in it. Like you've worked with a lot of great leaders, a lot of great individuals. Is that toxic relationship as toxic as it appears in the movie? Or is that fundamental? I've seen that relationship, especially in the past with Olympic athletes, especially in athletics, extreme performers seem to do wonders.

It does wonders for me. There's some of my best relationships. Now I'm not representative of everyone, certainly. But some of my best relationships for mentee and mentor have been toxic from an external perspective. What do you make of that movie? What do you make of that kind of relationship?

- That's not my favorite movie. (laughing) - Okay, so you don't think that's a healthy, you don't think that kind of relationship is a great example of a great leader? - I think it's a short-term strategy. I mean, look, being hard on someone is not the same as toxicity.

If you go to the Marine Corps, a drill instructor will be very hard on their Marines. But still, even on the last day of bootcamp, they'll take their hat off and they'll become a human. But of all the drill instructors, the three or four main drill instructors assigned to a group of recruits, the one that they all want the respect of is the one that's the hardest on them.

That's true. And you hear, there's plenty of stories of people who wanna earn the respect of a hard parent or a hard teacher. But fundamental, that parent, that teacher, that drill instructor has to believe in that person, has to see potential in them. It's not a formula, which is if I'm hard on people, they'll do well, which is there has to still be love.

It has to be done with absolute love, and it has to be done responsibly. I mean, some people can take a little more pressure than others, but I think it's irresponsible to think of it as a formula, that if I'm just toxic at people, they will do well. It depends on their personalities, first of all.

That works for some, but not all. And second of all, it can't be done willy-nilly. It has to still be done with care and love. And sometimes you can get equal or better results without all of the toxicity. - I guess toxicity, on my part, was a really bad word to use.

But if we talk about what makes a good leader and just look at an example in particular, looking at Elon Musk, he's known to push people to their limits in a way that I think really challenges people in a way they've never been challenged before, to do the impossible.

But it can really break people. - And jobs was hard, and Amazon is hard. But the thing that's important is none of them lie about it. People ask me about Amazon all the time. Like, Jeff Bezos never lied about it. Even the ones who like Amazon don't last more than a couple of years before they burn out.

But when we're honest about the culture, then it gives people the opportunity who like to work in that kind of culture to choose to work in that kind of culture. As opposed to pretending and saying, "Oh no, this is all lovey-lovey here." And then you show up and it's the furthest thing from it.

So, I mean, I think the reputations of putting a lot of pressure on people to... Jobs was not an easy man to work for. He pushed people, but everyone who worked there was given the space to create and do things that they would not have been able to do anywhere else, and work at a level that they didn't work anywhere else.

And Jobs didn't have all the answers. I mean, he pushed his people to come up with answers. He wasn't just looking for people to execute his ideas. And people did. People accomplished more than they thought they were capable of, which is wonderful. - How do you... You're talking about the infinite game, and not thinking about too short term, and yet you see some of the most brilliant people in the world being pushed by Elon Musk to accomplish some of the most incredible things.

When we're talking about autopilot, when we're talking about some of the hardware engineering, they do some of the best work of their life, and then leave. How do you balance that in terms of what it takes to be a good leader, what it takes to accomplish great things in your life?

- Yeah, so I think there's a difference between someone who can get a lot out of people in the short term, and building an organization that can sustain beyond any individual. There's a difference. - When you say beyond any individual, you mean beyond, like if the leader dies? - Correct.

Like could Tesla continue to do what it's doing without Elon Musk? - And you're perhaps implying, which is a very interesting question, that it cannot. - I don't know. The argument you're making of this person who pushes everyone, arguably is not a repeatable model. Is Apple the same without Steve Jobs?

Or is it slowly moving in a different direction? Or has he established something that could be resurrected with the right leader? - That was his dream, I think, is to build an organization that lives on beyond him. At least I remember reading that somewhere. - I think that's what a lot of leaders desire, which is to create something that was bigger than them.

Most businesses, most entrepreneurial ventures could not pass the school bus test, which is if the founder was hit by a school bus, would everyone continue the business without them, or would they all just go find jobs? And the vast majority of companies would fail that test, especially in the entrepreneurial world, that if you take the inspired visionary leader away, the whole thing collapses.

So is that a business, or is that just a force of personality? And a lot of entrepreneurs face that reality, which is they have to be in every meeting, make every decision, come up with every idea, because if they don't, who will? And the question is, well, what have you done to build your bench?

Sometimes it's ego, the belief that only I can. Sometimes it's just things did so well for so long that just forgot. And sometimes it's a failure to build the training programs or hire the right people that could replace you, who are maybe smarter and better. And browbeating people is only one strategy.

I don't think it's necessarily the only strategy, nor is it always the best strategy. I think people get to choose the cultures they wanna work in. So this is why I think companies should be honest about the kind of culture that they've created. I heard a story about Apple where somebody came in from a big company, he had accomplished a lot and his ego was very large and he was going on about how he did this and he did that and he did this and he did that.

And somebody from Apple said, "We don't care what you've done. The question is, what are you gonna do?" And for somebody who wants to be pushed, that's the place you go, because you choose to be pushed. Now, we all wanna be pushed to some degree. Anybody who wants to accomplish anything in this world wants to be pushed to some degree, whether it's through self-pressure or external pressure or public pressure, whatever it is.

But I think this whole idea of one size fits all is a false narrative of how leadership works. But what all leadership requires is creating an environment in which people can work at their natural best. - But you have a sense that it's possible to create a business where it lives on beyond you.

So if we look at now, if we just look at this current moment, I just recently talked to Jack Dorsey, CEO of Twitter, and he's under a lot of pressure now. I don't know if you're aware of the news that he's being pushed out as potentially as the CEO of Twitter, 'cause he's the CEO already of an incredibly successful company.

Plus he wants to go to Africa to live a few months in Africa to connect with the world that's outside of Silicon Valley. And sort of there's this idea, well, can Twitter live without Jack? - We'll find out. - But you have a general, as a student of great leadership, you have a general sense that it's possible.

- Yeah, of course it's possible. I mean, what Bill Gates built with Microsoft may not have survived Steve Ballmer if the company weren't so rich. But Satya Nardala is putting it back on track again. It's become a visionary company again. It's attracting great talent again. It went through a period where they couldn't get the best talent and the best talent was leaving.

Now people want to work for Microsoft again. Well, that's not because of pressure. Ballmer put more pressure on people mainly to hit numbers than anything else. That didn't work. - Yes. - Right? And so the question is, what kind of pressure are we putting on people? We're putting on pressure people to hit numbers or hit arbitrary deadlines, or putting on pressure on people because we believe that they can do better work.

And the work that we're trying to do is to advance a vision that's bigger than all of us. And if you're gonna put pressure on people, it better be for the right reason. Like if you're gonna put pressure on me, it better be for a worthwhile reason. If it's just to hit a goal, if it's just to hit some arbitrary date or some arbitrary number or make a stock price hit some target, you can keep it, I'm out of here.

But if you want to put pressure on me because we are brothers and sisters in arms, working to advance a cause bigger than ourselves, that we believe whatever we're gonna build will significantly contribute to the greater good of society, then go ahead, I'll take the pressure. And if you look at the apples and if you look at the Elon Musk's, the jobs in the Elon Musk, they fundamentally believe that what they were doing would improve society and it was for the good of humankind.

And so the pressure, in other words, what they were doing was more important, more valuable than any individual on the team. And so the pressure they put on people served a greater good. And so we looked to the left and we looked to the right to each other and said, we're in this together.

We accept this, we want this. But if it's just pressure to hit a number or make the widget move a little faster, and that's soul sucking. That's not passion, that's stress. And I think a lot of leaders confuse that making people work hard is not what makes them passionate.

Giving them something to believe in and work on is what drives passion. - And when you have that, then turning up the pressure only brings people together, drives them further. - If done the right way. - Done the right way. Speaking of pressure, I'm gonna give you 90 seconds to answer the last question, which is if I told you that tomorrow was your last day to live, we talked about mortality, sunrise to sunset, can you tell me, can you take me through the day?

What do you think that day would involve? You can't spend it with your family, I told you as well. - I would probably want to fill all of my senses with things that excite my senses. I'd want to look at beautiful art, I'd want to listen to beautiful music, I'd want to taste incredible food, I'd want to smell amazing tastes, I'd want to touch something that's beautiful to touch, I'd want all of my senses to just be consumed with things that I find beautiful.

- And you talked about this idea of, we don't do it often these days, of just listening to music, turning off all the devices and actually taking in and listening to music. So as an addendum, if we were to talk about music, what song would you be blasting in this last day you're alive?

Is it Led Zeppelin, what are we talking about? - No, no, there's probably gonna be a Beatles song in there, there'll definitely be some Beethoven in there. - The classics. - The classics. - Okay. - Yeah, exactly. - Thank you so much for talking today, thank you for making time for it.

Under pressure, we made it happen. - Yeah, it was great. - Thanks for listening to this conversation with Simon Sinek, and thank you to our sponsors, Cash App and Masterclass. Please consider supporting the podcast by downloading Cash App and using code LEXPODCAST, and signing up to Masterclass at masterclass.com/lex.

If you enjoy this podcast, subscribe on YouTube, review it with Five Stars on Apple Podcast, support it on Patreon, or simply connect with me on Twitter at Lex Friedman. And now, let me leave you with some words from Simon Sinek. There are only two ways to influence human behavior.

You can manipulate it, or you can inspire it. Thank you for listening, I hope to see you next time. (upbeat music) (upbeat music)