WEBVTT

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Welcome back to the Deep Dive. I hope you are

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ready to swim because today we are opening a

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file on a figure who, quite honestly, feels like

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he is everywhere right now. Oh, everywhere. That's

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not an exaggeration. You open your LinkedIn feed.

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There he is. You walk into a corporate boardroom.

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Someone is quoting him. You go on YouTube and

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you see that, you know, that slightly grady video

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of a guy in a suit with a flip chart and a cheap

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marker just completely changing the way millions

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of people think about business. It is genuinely

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hard to exist in the modern professional world

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without tripping over Simon Sinek. It really

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is. He has become part of the cultural furniture

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of leadership. Exactly. Yeah. And that is why

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we need to talk about him. But here's the thing

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that really triggered this specific deep dive

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for me. OK. Usually when we cover these massive

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business gurus, they fit a very specific, very

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rigid mold. They're the ex -CEO of General Electric.

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Right. The Wharton MBA. They're a tenured professor

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of economics at Harvard. They're quantitative

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analysts who crunched the numbers and, you know,

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found the secret sauce. But Simon Sinek. He is

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none of those things. No, he definitely breaks

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the mold. He's an outlier in, I think, the best

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possible way. And I think the best place to start

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is with how he actually defines himself. Because

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in the source material we have in front of us,

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the biographical review, the publication history,

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he doesn't call himself a management consultant.

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Nope. He doesn't call himself a strategist. Right.

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If you look at his own bio, the title he gives

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himself is optimist. An optimist. With a capital

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O. A capital O. It is a defined professional

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title for him. It's on his business card. I think

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so. And I think for a lot of people that might

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sound a little, well, a little fluffy. Yeah,

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a bit. It sounds like something you put in your

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Instagram bio, not on your tax return. But our

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mission today is to peel back that label and

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look at the actual mechanics underneath. Because

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Sinek isn't just selling good vibes. He has built

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a massive global empire based on a very specific,

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very rigorous way of looking at human behavior.

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And that's the hook, right? We're going to dig

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into the fact that his background isn't in business

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at all. It's in anthropology. The absolute key

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to understanding him. We're going to look at...

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How a guy who's studied cultural rituals and

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human tribes ends up advising the U .S. military,

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the Rand Corporation, and some of the biggest

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companies on Earth. It's a wild trajectory. And

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we aren't going to shy away from the business

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of being Simon Sinek either. No. We are going

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to look at the evolution of his bibliography,

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his institutional ties, and yes, even some of

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the controversies that have popped up along the

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way, specifically regarding government contracts.

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It is a fascinating story. From a kid moving

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across the globe to a global thought leader.

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So let's start at the very beginning. Let's do

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it. Because to understand the why guy, you have

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to understand where he actually came from. And

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where he came from isn't a simple answer. If

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you look at his early biography, the geography

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is all over the map. Literally. So, Simon Oliver

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Sinek, born October 9th, 1973. In Wimbledon,

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London, England. So he starts his life across

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the pond. Right. A proper English start. But

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he doesn't stay there. And this is the part that

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really jumped out at me as we were prepping this.

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His childhood map is just, it's incredibly erratic.

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It's nomadic. He's born in Wimbledon. Then the

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family moves to Johannesburg, South Africa. Right.

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Then back to London. Then over to Hong Kong.

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And then finally, they settle in the United States.

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Just pause and think about that itinerary for

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a second. We're talking about the 1970s and 80s

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here. Yeah. These aren't just different cities.

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They are entirely different universes culturally.

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You have post -imperial Britain. You have South

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Africa during the apartheid era. A very intense

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place to be. Absolutely. Then you have Hong Kong,

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which was this frenetic, high -energy British

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colony on the edge of communist China. And then

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you land in the suburbs of New Jersey. That is

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a serious amount of cultural whiplash for a kid.

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I can't even imagine. It is. But think about

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what that does to a developing brain. When you

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are the new kid that many times in that many

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different environments, you never fully belong

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to any of them. Right. You are always the outsider.

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You are always the other. You're the third culture

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kid. That's the term for it, isn't it? Exactly.

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And when you are the outsider, you develop a

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survival skill. Observation. You have to. You

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have no choice. If you want to survive socially.

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on a playground in Johannesburg and then a year

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later on a playground in Hong Kong, you have

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to figure out the rules fast. You have to watch.

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Who's in charge here? Who is the leader here?

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How do they show respect? What gets you punished?

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What gets you rewarded? You have to decode the

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tribe just to get through lunch. Precisely. You

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become a watcher of human behavior by necessity.

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You learn to spot the patterns that the locals,

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the people who have lived there their whole lives,

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don't even see because they are too close to

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it. So in a way, his childhood forced him to

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become an amateur anthropologist before he even

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knew what the word meant. I don't think it is

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a coincidence at all, not one bit, that when

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he finally got to college, that is exactly what

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he chose to study. Let's look at the education

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path, because this is where the foundation is

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poured. He settles in the U .S., goes to high

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school in New Jersey, Northern Valley Regional

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High School at Demarest, specifically. Right.

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Go Norseman. Graduates in 1991. Mm -hmm. And

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then he heads to Brandeis University in Massachusetts.

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Now, if you are planning to become a massive

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business consultant, usually you'd expect this

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part of the story to be, and then he enrolled

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in the Wharton School of Business or he majored

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in economics. But he didn't. He earned a B .A.

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in cultural anthropology. This, to me, is the

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Rosetta Stone for his entire career. If you skip

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this fact, you miss the entire point of Simon

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Sinek. I agree completely because cultural anthropology

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is not the study of spreadsheets. It isn't the

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study of profit margins. It is the study of humans.

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It is the study of why groups of people behave

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the way they do. It looks at symbols, rituals,

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social structures, hierarchies and myths. Right.

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So for the listener who might not be familiar

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with the field, an anthropologist looks at a

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group, say a remote tribe in the Amazon and asks,

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what holds this group together? Why do they trust

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their leader? What are their taboos? All these

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like. Invisible forces. Exactly. And Sinek's

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genius was that he took that lens, that anthropological

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lens, and he turned it on the modern corporation.

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He realized that a company like Microsoft or

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Apple or American Airlines isn't a machine. It's

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a tribe. It's a group of primates trying to survive

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and thrive together. So while other consultants

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are looking at the P &amp;L statement, Sinek is looking

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for the rituals. He's looking for the signs of

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safety. He is looking at the biology of belonging.

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If you listen to his language, even today it

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is very tribal. He talks about the circle of

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safety. He talks about servant leadership. He

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talks about trust as a biological reaction, not

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a contractual obligation. That is pure anthroposophical.

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It's straight out of the textbook. It explains

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why his advice feels so different. It's not increase

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efficiency by 10 percent. Yeah. It's make your

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people feel safe so they can do their best work.

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It's a completely different paradigm. It grounds

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business and humanity. Yeah. But interestingly

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enough, he didn't go straight from Brandeis to

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the TED stage. He took a detour that I think

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is equally important. Right. The law school era

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or the almost lawyer era, I should say. The almost

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lawyer era. Yeah. He studied law at City University

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London. So back to London again. Back to London.

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And even though he didn't become a practicing

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barrister. This training is crucial. Why is that?

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Law is about logic. It is about structure. It

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is about taking a messy, complex set of facts

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and organizing them into a coherent, persuasive

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argument. Okay, I see. So you have the observer

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from the anthropology side, the person who sees

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the human patterns. Yes. And then you have the

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advocate from the law side, the person who can

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build a clear, logical case around what he's

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seeing. And those two things combine to create

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a very, very powerful communicator, someone who

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can see a deep human truth and then structure

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a logical, irrefutable argument around it. Which

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leads us perfectly to his first real career,

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advertising. The industry of persuasion. He worked

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at some serious agencies, Euro, RSCG, and Ogilvy

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&amp; Mather in New York. Ogilvy? Yeah. These aren't

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small shops. These are the giants of Madison

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Avenue. And working at a place like Ogilvy implies

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a few things. I mean, it's the Mad Men legacy,

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right? Totally. You are trained to take a complex

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product or a complex message and distill it down

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to one simple emotional hook. You have to be

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able to draw it on a napkin. You have to be able

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to say it in a tagline. You aren't selling the

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features of the car. You're selling the feeling

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of the open road. Exactly. And if you look at

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Sinek's most famous concept, the golden circle,

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it is essentially a perfect piece of ad copy.

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It is a diagram. It is visual. It is simple.

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It is sticky. He took deep anthropological concepts

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about human motivation and packaged them with

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the slickness and clarity of a high -end ad executive.

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Wow, that's a great connection. I hadn't thought

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of it that way. It's the perfect marriage of

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his skills. So he spends time in the ad world.

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He learns the trade of messaging. He eventually

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launches his own consultancy, Cynic Partners.

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But the moment everything changes, the tipping

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point where he goes from guy with a consultancy

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to Simon Sinek is 2009. 2009, the year the why

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went global. He publishes the book, Start With

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Why, How Great Leaders Inspire Everyone to Take

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Action. And critically, he gives a TEDx talk.

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We have to pause on that TED Talk because the

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source material notes that this is one of the

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most viewed TED Talks of all time. We are talking

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tens of millions of views. It's staggering. And

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if you go back and watch it, it is strikingly

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low tech. Oh, it's not flashy at all. There are

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no bells and whistles. The audio is a little

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echoey. He's wearing a slightly ill -fitting

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suit. He doesn't have a PowerPoint. He doesn't

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have lasers. He has a flip chart and a Sharpie.

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And he drops the microphone at one point, doesn't

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he? Or the marker. Something clatters to the

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ground. Yes, it's very raw. But that rawness

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is part of why it worked. And we have to look

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at the context of 2009. Oh, absolutely. The Great

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Recession. The world had just fallen off a cliff.

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The global financial system had nearly collapsed.

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Trust in corporations was at absolute zero. People

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were angry. They were scared. They felt betrayed

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by their leaders. They felt that business was

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just about greed. And here comes this guy with

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a simple marker standing there saying, We are

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doing it all wrong. It's not about money. It's

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about why. The timing was just perfect. It was

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the exact message people needed to hear at that

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moment. It was a life raft. Let's break down

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that concept, the golden circle, because it is

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the foundation of everything else he does. Right.

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So for anyone listening, just visualize a target.

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Yeah. Three concentric circles. Like a dartboard.

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Exactly. The outside ring is what, the middle

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ring is how, and the center bullseye is why.

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Okay. Sinek argues that every single organization

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on the planet knows what they do. That's the

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easy part. We make computers. We sell legal services.

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We manufacture cars. Everyone knows the what.

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And some know how they do it. That's your value

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proposition. We have the best proprietary process.

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We use the finest materials. That's the how,

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the differentiator. But very, very few know.

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Why they do it. And by why, he doesn't mean to

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make a profit. That's a result. He's very clear

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on that. He means, what is your cause? What is

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your belief? Why does your organization exist

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in the first place? Why do you get out of bed

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in the morning? And why should anyone care? And

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his big argument is that most leaders communicate

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from the outside in. They start with the what?

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All the time. Here is our new car. It has great

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gas mileage and leather seats. Buy it. But the

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inspiring leaders. The ones who changed the world,

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the Apples, the Martin Luther King Jrs, the Wright

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brothers, they communicate from the inside out.

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They start with the why. The famous Apple example.

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Instead of, we make great computers, it's...

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It's everything we do, we believe in challenging

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the status quo. We believe in thinking differently.

00:12:14.000 --> 00:12:16.519
That's the why. Okay. The way we challenge the

00:12:16.519 --> 00:12:18.620
status quo is by making our products beautifully

00:12:18.620 --> 00:12:21.600
designed and simple to use. That's the how. And

00:12:21.600 --> 00:12:23.759
then... We just happen to make great computers.

00:12:23.779 --> 00:12:26.039
That's the what? Want to buy one? It's a total

00:12:26.039 --> 00:12:28.580
reversal. And it feels completely different.

00:12:28.779 --> 00:12:31.179
It feels like an invitation, not a sales pitch.

00:12:31.759 --> 00:12:33.779
And he connects this back to biology, right?

00:12:34.179 --> 00:12:36.460
This isn't just a linguistic trick. This is the

00:12:36.460 --> 00:12:39.440
anthropology coming back in a huge way. He argues

00:12:39.440 --> 00:12:42.720
that the why and the how correspond to the limbic

00:12:42.720 --> 00:12:44.919
brain. OK, the limbic brain. The part of the

00:12:44.919 --> 00:12:47.980
brain that controls feelings like trust and loyalty.

00:12:48.559 --> 00:12:50.840
It's also the part of the brain that has no capacity

00:12:50.840 --> 00:12:53.919
for language. Right. Which is why when you ask

00:12:53.919 --> 00:12:56.779
someone, why do you love your spouse? Yeah. They

00:12:56.779 --> 00:12:59.700
can't give you a bulleted list of reasons. They

00:12:59.700 --> 00:13:01.799
can't. They just say, I don't know, it just feels

00:13:01.799 --> 00:13:04.580
right. Exactly. That is the limbic brain speaking.

00:13:04.740 --> 00:13:07.279
That's your gut feeling. So if you want to influence

00:13:07.279 --> 00:13:10.419
behavior, if you want loyalty, you have to speak

00:13:10.419 --> 00:13:12.179
to the limbic brain. You have to speak to the

00:13:12.179 --> 00:13:14.360
why. But if you only talk about features and

00:13:14.360 --> 00:13:17.679
benefits, you were just talking to the neocortex.

00:13:17.879 --> 00:13:20.039
The rational brain. Yeah. You might get a transaction,

00:13:20.279 --> 00:13:22.440
but you won't get loyalty. People don't buy what

00:13:22.440 --> 00:13:25.110
you do. They buy why you do it. That concept

00:13:25.110 --> 00:13:27.490
just exploded. It resonated so deeply because

00:13:27.490 --> 00:13:30.049
I think people were starving for meaning in their

00:13:30.049 --> 00:13:32.809
work, especially after 2008. They were desperate

00:13:32.809 --> 00:13:34.649
for it. But what's interesting to me is that

00:13:34.649 --> 00:13:36.570
Sinek didn't stop there. He didn't just become

00:13:36.570 --> 00:13:39.370
the why guy and retire. No, his thinking evolved.

00:13:39.769 --> 00:13:42.009
And if you look at his bibliography chronologically,

00:13:42.250 --> 00:13:44.610
you can see him expanding the theory, building

00:13:44.610 --> 00:13:47.950
a whole universe around this one core idea. Let's

00:13:47.950 --> 00:13:49.610
walk through that library because it tells a

00:13:49.610 --> 00:13:52.870
story of its own. 2009 is start with why. Then

00:13:52.870 --> 00:13:56.299
we have a... Bit of a gap until 2014. And then

00:13:56.299 --> 00:13:58.860
he drops Leaders Eat Last. Leaders Eat Last.

00:13:59.039 --> 00:14:01.500
Why some teams pull together and others don't.

00:14:01.500 --> 00:14:03.799
Now look at the shift in focus. It's a different

00:14:03.799 --> 00:14:06.259
lens. The first book was about the individual

00:14:06.259 --> 00:14:09.860
leader or the brand how to inspire action outward.

00:14:10.440 --> 00:14:12.659
This book is about the team. It's about the internal

00:14:12.659 --> 00:14:15.980
culture. How do you inspire action inward? The

00:14:15.980 --> 00:14:17.620
title itself is a great story. Where did that

00:14:17.620 --> 00:14:19.700
come from? It comes from a conversation he had

00:14:19.700 --> 00:14:22.120
with a Marine Corps general. He asked him, what

00:14:22.120 --> 00:14:24.240
makes the Marines so effective? Why are they

00:14:24.240 --> 00:14:26.340
so tight knit? Why would they risk their lives

00:14:26.340 --> 00:14:28.700
for each other? And the general simply said,

00:14:28.820 --> 00:14:32.159
officers eat last. It's a literal rule in the

00:14:32.159 --> 00:14:35.340
chow hall. It is. When the Marines line up for

00:14:35.340 --> 00:14:37.960
food, the most junior recruit eats first. The

00:14:37.960 --> 00:14:40.659
senior general eats last. And if the food runs

00:14:40.659 --> 00:14:44.159
out, the general goes hungry. Wow. That is a

00:14:44.159 --> 00:14:46.659
powerful symbol. It is the physical manifestation

00:14:46.659 --> 00:14:50.080
of leadership. It signals to the tribe, I will

00:14:50.080 --> 00:14:52.840
sacrifice my comfort for your survival. Your

00:14:52.840 --> 00:14:55.700
well -being comes before my own. And Sinek argues

00:14:55.700 --> 00:14:58.580
that this creates what he calls the circle of

00:14:58.580 --> 00:15:01.720
safety. Yes, the circle of safety. When we feel

00:15:01.720 --> 00:15:03.740
safe, when we know our leader has our back, our

00:15:03.740 --> 00:15:07.700
biology changes. Our cortisol levels drop. Cortisol

00:15:07.700 --> 00:15:10.370
is the stress hormone. The fight or flight chemical.

00:15:10.590 --> 00:15:12.889
Right. If you are constantly worried that your

00:15:12.889 --> 00:15:15.169
boss is going to fire you to save a nickel or

00:15:15.169 --> 00:15:16.909
throw you under the bus in a meeting to look

00:15:16.909 --> 00:15:19.269
good. Which happens all the time. You are dripping

00:15:19.269 --> 00:15:21.570
with cortisol. You are in fight or flight mode.

00:15:21.710 --> 00:15:24.049
You can't innovate. You can't trust. You are

00:15:24.049 --> 00:15:26.889
just trying to survive the day. But if the leader

00:15:26.889 --> 00:15:30.029
eats last, if they prove they are there to protect

00:15:30.029 --> 00:15:32.909
you, the cortisol drops and oxytocin kicks in.

00:15:32.990 --> 00:15:35.830
The bonding chemical. The love drug, they sometimes

00:15:35.830 --> 00:15:40.769
call it. It facilitates empathy. trust, generosity.

00:15:41.350 --> 00:15:44.149
And when that happens, the team naturally pulls

00:15:44.149 --> 00:15:46.570
together to face external threats instead of

00:15:46.570 --> 00:15:49.570
fighting each other internally. Sinek is basically

00:15:49.570 --> 00:15:53.230
telling modern CEOs that they are failing because

00:15:53.230 --> 00:15:56.230
they are ignoring our basic primate programming.

00:15:56.570 --> 00:15:58.450
Leaders Eat Last was a huge hit. It made the

00:15:58.450 --> 00:16:00.470
New York Times and Wall Street Journal bestseller

00:16:00.470 --> 00:16:03.210
lists. It cemented him as a management expert,

00:16:03.289 --> 00:16:05.690
not just a marketing guy. For sure. Then in 2016,

00:16:05.789 --> 00:16:08.370
we got a bit of a curveball. Together is Better,

00:16:08.529 --> 00:16:10.690
a little book of inspiration. A little book.

00:16:10.909 --> 00:16:12.730
This one feels different. It's illustrated. It's

00:16:12.730 --> 00:16:14.629
almost like a fable or a children's book for

00:16:14.629 --> 00:16:16.850
adults. It is, and it suggests a move toward

00:16:16.850 --> 00:16:19.269
accessibility. He wanted something that wasn't

00:16:19.269 --> 00:16:22.509
a dense 300 -page business book. He wanted something

00:16:22.509 --> 00:16:25.009
you could give to a graduate or leave on a desk

00:16:25.009 --> 00:16:27.730
in the office. It's the optimism brand distilled

00:16:27.730 --> 00:16:30.330
into a pure, shareable format. It's snackable

00:16:30.330 --> 00:16:33.370
content. And then in 2017, find your why. This

00:16:33.370 --> 00:16:35.429
was the necessary tactical follow -up. It was

00:16:35.429 --> 00:16:37.990
almost inevitable. Because after start with why,

00:16:38.250 --> 00:16:40.169
the number one question he must have gotten was,

00:16:40.370 --> 00:16:42.309
Okay, Simon, I get it. The why is important.

00:16:42.879 --> 00:16:45.320
But how do I find mine? Right. It's easy for

00:16:45.320 --> 00:16:47.940
Apple. They have Steve Jobs. But what if I'm

00:16:47.940 --> 00:16:50.320
a mid -level manager at a paper company? What's

00:16:50.320 --> 00:16:53.679
my grand, world -changing why? Exactly. So Find

00:16:53.679 --> 00:16:55.879
Your Why is a practical guide. It's a workbook.

00:16:55.980 --> 00:16:59.000
It has exercises and steps. It marks the shift

00:16:59.000 --> 00:17:02.559
from philosopher to trainer. He is giving people

00:17:02.559 --> 00:17:04.700
the shovel to do the digging themselves. It's

00:17:04.700 --> 00:17:06.420
the application. It's the application. And then

00:17:06.420 --> 00:17:09.059
the most recent major work in our source stack

00:17:09.059 --> 00:17:12.640
is 2019's The Infinite Game. And honestly, I

00:17:12.640 --> 00:17:15.039
think this is his most intellectually ambitious

00:17:15.039 --> 00:17:17.579
concept. I agree. This is where he steps out

00:17:17.579 --> 00:17:19.980
of just team dynamics and looks at macro strategy.

00:17:20.259 --> 00:17:22.460
This is him thinking on a much grander scale.

00:17:22.740 --> 00:17:25.099
Let's unpack the title. What is an infinite game?

00:17:25.319 --> 00:17:27.539
The concept comes from a scholar named James

00:17:27.539 --> 00:17:30.819
P. Kars. Sinek takes that academic idea and applies

00:17:30.819 --> 00:17:33.740
it to business and capitalism. Basically, there

00:17:33.740 --> 00:17:36.539
are two types of games, finite games and infinite

00:17:36.539 --> 00:17:39.579
games. A finite game is like football or chess.

00:17:40.029 --> 00:17:43.950
Right. Known players. Fixed rules. Agreed upon

00:17:43.950 --> 00:17:46.750
objective. There is a klong or a finish line.

00:17:46.950 --> 00:17:48.809
At the end of the game, someone has more points.

00:17:49.089 --> 00:17:52.930
They win, you lose. Game over. Simple. Very clear.

00:17:53.190 --> 00:17:55.910
But an infinite game has known and unknown players.

00:17:56.210 --> 00:17:58.829
The rules are changeable. And the objective is

00:17:58.829 --> 00:18:01.670
not to win, but to keep playing. To perpetuate

00:18:01.670 --> 00:18:04.579
the game. Like marriage. Or friendship. You don't

00:18:04.579 --> 00:18:06.779
win a marriage. Exactly. You don't win friendship.

00:18:07.039 --> 00:18:08.920
The goal is to keep the relationship healthy

00:18:08.920 --> 00:18:11.559
and strong so it continues. And Sinek argues

00:18:11.559 --> 00:18:14.579
that business is an infinite game. Yes. There

00:18:14.579 --> 00:18:16.640
is no such thing as winning business. You can't

00:18:16.640 --> 00:18:19.319
win global commerce. The game existed before

00:18:19.319 --> 00:18:22.359
your company and it will exist after. But the

00:18:22.359 --> 00:18:24.940
problem is most executives lead as if they are

00:18:24.940 --> 00:18:27.839
playing a finite game. They are obsessed with

00:18:27.839 --> 00:18:30.400
beating the competition this quarter, being number

00:18:30.400 --> 00:18:33.109
one. in their category and cynic says that mindset

00:18:33.109 --> 00:18:36.329
is destructive if you play a finite game trying

00:18:36.329 --> 00:18:38.170
to win the quarter in the middle of an infinite

00:18:38.170 --> 00:18:41.730
game business you make bad choices you cut r

00:18:41.730 --> 00:18:44.029
d to make your numbers look better you squeeze

00:18:44.029 --> 00:18:47.190
your employees on salaries and benefits you degrade

00:18:47.190 --> 00:18:49.849
your product quality just to hit a number you

00:18:49.849 --> 00:18:51.750
might win the quarter but you eventually run

00:18:51.750 --> 00:18:53.809
out of the will or the resources to keep playing

00:18:53.809 --> 00:18:56.369
you burn down the house to stay warm for a night

00:18:56.670 --> 00:18:59.089
Precisely. In the infinite game, the goal is

00:18:59.089 --> 00:19:01.930
resilience. The goal is to build an organization

00:19:01.930 --> 00:19:04.410
that can survive the ups and downs and outlast

00:19:04.410 --> 00:19:07.410
the others. It ties everything together. It does.

00:19:07.549 --> 00:19:10.950
You need a why to have the stamina for an infinite

00:19:10.950 --> 00:19:14.569
game. You need leaders eat last to have the team

00:19:14.569 --> 00:19:16.970
cohesion to weather the storms. And you need

00:19:16.970 --> 00:19:19.490
the infinite mindset to navigate the strategy.

00:19:19.809 --> 00:19:22.230
It's a very complete ecosystem of thought. He's

00:19:22.230 --> 00:19:24.829
really built a whole world. But speaking of ecosystems,

00:19:25.210 --> 00:19:27.670
we need to talk about the business Sinek has

00:19:27.670 --> 00:19:30.230
built around himself. Because he isn't just writing

00:19:30.230 --> 00:19:32.829
books in a cabin somewhere. Oh, no. He's running

00:19:32.829 --> 00:19:36.049
a machine. A well -oiled machine. And the sources

00:19:36.049 --> 00:19:38.130
give us a glimpse into how that machine is structured.

00:19:38.529 --> 00:19:42.710
First off, publishing. In November 2018, Publishers

00:19:42.710 --> 00:19:45.250
Weekly reported that Sinek started Optimism Press.

00:19:45.529 --> 00:19:48.250
Which is an imprint of Penguin Random House.

00:19:48.720 --> 00:19:51.279
That is a big deal. A really big deal. Having

00:19:51.279 --> 00:19:53.359
your own imprint means you aren't just an author.

00:19:53.539 --> 00:19:57.619
You are a curator. You are a kingmaker. He is

00:19:57.619 --> 00:20:00.700
selecting other voices that align with his worldview

00:20:00.700 --> 00:20:03.500
to elevate under his brand. It's a huge expansion

00:20:03.500 --> 00:20:05.740
of influence. And then there's the optimism company.

00:20:05.819 --> 00:20:08.079
A digital learning platform. This is the scale

00:20:08.079 --> 00:20:11.960
play. Right. He realized he can't fly to every

00:20:11.960 --> 00:20:14.819
company in the world to give a speech. So he

00:20:14.819 --> 00:20:18.650
built a platform to train people digitally. It

00:20:18.650 --> 00:20:21.650
institutionalizes the optimist title. It turns

00:20:21.650 --> 00:20:24.490
it from a personal brand into a corporate entity.

00:20:24.789 --> 00:20:26.609
But what really caught my eye in the research,

00:20:26.730 --> 00:20:28.170
and this is where we get into the institutional

00:20:28.170 --> 00:20:31.470
ties section of our outline, is that he's not

00:20:31.470 --> 00:20:33.390
just operating in the corporate training world.

00:20:33.569 --> 00:20:36.589
He has some serious academic and policy credentials.

00:20:37.049 --> 00:20:39.470
This is a crucial distinction. There are a lot

00:20:39.470 --> 00:20:42.069
of motivational speakers out there, a lot. But

00:20:42.069 --> 00:20:44.089
very few of them are instructors at Columbia

00:20:44.089 --> 00:20:46.329
University. Right. He is an instructor of strategic

00:20:46.329 --> 00:20:49.069
communications at Columbia. That is Ivy League.

00:20:49.210 --> 00:20:52.309
That is serious academic weight. And even more

00:20:52.309 --> 00:20:55.349
significant, in my view, is his connection to

00:20:55.349 --> 00:20:58.710
the Rand Corporation. Yes. The Rand Corporation.

00:20:58.930 --> 00:21:01.930
For listeners who don't know, what is Rand? This

00:21:01.930 --> 00:21:04.950
isn't some fly -by -night consulting firm. No.

00:21:04.990 --> 00:21:08.009
Rand is a global policy think tank. They were

00:21:08.009 --> 00:21:10.269
originally formed to offer research and analysis

00:21:10.269 --> 00:21:12.549
to the U .S. Armed Forces after World War II.

00:21:12.789 --> 00:21:15.069
They deal with national security, international

00:21:15.069 --> 00:21:18.880
affairs, law, business, health. They are the

00:21:18.880 --> 00:21:21.380
heavy hitters of strategic thinking. The people

00:21:21.380 --> 00:21:23.559
who advise governments on incredibly complex

00:21:23.559 --> 00:21:26.839
issues. The very same. And Sinek is listed as

00:21:26.839 --> 00:21:29.660
an adjunct staff member. That validates his standing

00:21:29.660 --> 00:21:31.799
in a way that being a New York Times bestseller

00:21:31.799 --> 00:21:33.890
doesn't. Completely different kind of validation.

00:21:36.190 --> 00:21:46.150
It suggests that his ideas about leadership aren't

00:21:46.150 --> 00:21:48.829
just fluff. They have strategic utility. When

00:21:48.829 --> 00:21:50.730
you are talking about how to lead a military

00:21:50.730 --> 00:21:53.990
unit or a government agency, the stakes are different

00:21:53.990 --> 00:21:56.880
than selling sneakers. And Sinek has managed

00:21:56.880 --> 00:21:59.720
to bridge that gap. He speaks at the UN Global

00:21:59.720 --> 00:22:02.640
Compact Leaders Summit. He's in these rooms where

00:22:02.640 --> 00:22:05.259
global decisions are being discussed. Which makes

00:22:05.259 --> 00:22:07.319
the next part of our deep dive even more interesting.

00:22:07.720 --> 00:22:09.700
Because when you operate at that level, when

00:22:09.700 --> 00:22:11.700
you work with governments and massive institutions,

00:22:12.059 --> 00:22:15.789
things can get... I certainly can. The optics

00:22:15.789 --> 00:22:18.069
get very tricky. We need to talk about the ICEE

00:22:18.069 --> 00:22:20.910
controversy. This is a specific event reported

00:22:20.910 --> 00:22:24.490
in the sources, specifically around June 2018.

00:22:24.769 --> 00:22:26.990
Right. So June 2018, the Young Turks reported

00:22:26.990 --> 00:22:30.910
on a contract. The amount was $98 ,000. And the

00:22:30.910 --> 00:22:33.490
client was U .S. Immigration and Customs Enforcement,

00:22:33.609 --> 00:22:36.549
or ICEE. And the nature of the contract was for

00:22:36.549 --> 00:22:39.130
leadership training. Correct. It was a no -bid

00:22:39.130 --> 00:22:41.869
contract, and it is important to note the facilitation

00:22:41.869 --> 00:22:44.759
here. The training was provided by Ernst &amp; Young.

00:22:44.960 --> 00:22:47.000
So let's break this down factually, just based

00:22:47.000 --> 00:22:49.160
on what's in the sources. Ernst &amp; Young is a

00:22:49.160 --> 00:22:51.380
massive professional services network, one of

00:22:51.380 --> 00:22:53.440
the big four. They do consulting, accounting,

00:22:53.680 --> 00:22:56.170
everything. Yes. And typically, large government

00:22:56.170 --> 00:22:59.730
agencies like ICE have standing multi -year,

00:22:59.869 --> 00:23:02.490
multi -million dollar contracts with firms like

00:23:02.490 --> 00:23:05.029
Ernst &amp; Young to provide all sorts of training

00:23:05.029 --> 00:23:07.809
and services. So Sinek's involvement was likely

00:23:07.809 --> 00:23:10.730
part of a broader package. It was likely a specific

00:23:10.730 --> 00:23:13.230
request fulfilled through that existing channel.

00:23:13.490 --> 00:23:16.250
It's not necessarily Simon Sinek knocking on

00:23:16.250 --> 00:23:18.789
ICE's door saying, hire me. It's more likely

00:23:18.789 --> 00:23:21.569
ICE telling Ernst &amp; Young. We want leadership

00:23:21.569 --> 00:23:23.849
training. Get us the Y guy. But the headline,

00:23:24.130 --> 00:23:28.990
$98 ,000 contract with IC. That lands differently

00:23:28.990 --> 00:23:31.450
depending on the political climate. And 2018

00:23:31.450 --> 00:23:34.470
was a very, very heated time regarding immigration

00:23:34.470 --> 00:23:37.009
policy in the U .S. It was. The family separation

00:23:37.009 --> 00:23:39.230
policy was miniature news. And this highlights

00:23:39.230 --> 00:23:41.289
the tension we mentioned earlier. When you position

00:23:41.289 --> 00:23:43.289
yourself as a leadership expert and your mission

00:23:43.289 --> 00:23:45.190
is to help leaders inspire action and create

00:23:45.190 --> 00:23:48.529
safety, who do you work with? Right. Do you only

00:23:48.529 --> 00:23:50.769
train leaders of organizations you agree with

00:23:50.769 --> 00:23:53.529
politically? Or do you believe that every organization

00:23:53.529 --> 00:23:56.109
needs better leadership? That is the central

00:23:56.109 --> 00:23:58.329
question. From a strictly professional standpoint,

00:23:58.750 --> 00:24:01.529
leadership training is a service. It is a commodity.

00:24:02.230 --> 00:24:05.029
Corporations buy it, nonprofits buy it, and yes,

00:24:05.250 --> 00:24:07.650
government agencies, including law enforcement

00:24:07.650 --> 00:24:10.690
and border control, buy it. They have managers

00:24:10.690 --> 00:24:13.250
and teams just like anyone else. And arguably,

00:24:13.390 --> 00:24:15.829
one could say that agencies with high -stress,

00:24:15.910 --> 00:24:18.690
high -stakes environments need concepts like

00:24:18.690 --> 00:24:21.890
leadership and circle of safety more than anyone.

00:24:22.250 --> 00:24:24.490
That is one perspective. If you believe in the

00:24:24.490 --> 00:24:27.470
leaders eat last philosophy, that leaders should

00:24:27.470 --> 00:24:29.650
protect their people and create a moral circle,

00:24:29.829 --> 00:24:32.410
then teaching that to a government agency could

00:24:32.410 --> 00:24:34.609
be seen as an attempt to improve the culture

00:24:34.609 --> 00:24:36.930
from within. But on the flip side, from another

00:24:36.930 --> 00:24:39.470
perspective, taking the money can be seen as

00:24:39.470 --> 00:24:42.430
an endorsement or at least a normalization of

00:24:42.430 --> 00:24:44.970
the agency itself and its policies at the time.

00:24:45.329 --> 00:24:47.950
Precisely. And that is why it became a news story.

00:24:48.440 --> 00:24:50.599
When you are a public figure preaching optimism

00:24:50.599 --> 00:24:53.079
and why, your client list becomes a statement

00:24:53.079 --> 00:24:54.819
of its own whether you intend it to be or not.

00:24:55.039 --> 00:24:56.859
It's a fascinating case study in the business

00:24:56.859 --> 00:24:59.160
of philosophy. You can have these pure ideals,

00:24:59.319 --> 00:25:01.359
but when they hit the real world of government

00:25:01.359 --> 00:25:04.019
contracting, it gets messy. The lines get blurred.

00:25:04.259 --> 00:25:06.720
It does. And yet, looking at the source material,

00:25:07.019 --> 00:25:09.700
this didn't seem to derail his career. He continued

00:25:09.700 --> 00:25:11.900
to publish, continued to speak, continued to

00:25:11.900 --> 00:25:14.380
build the optimism company. Which suggests that

00:25:14.380 --> 00:25:17.220
his core audience, the people playing the infinite

00:25:17.220 --> 00:25:20.369
game, Maybe he saw it as just another move on

00:25:20.369 --> 00:25:22.710
the board. Or maybe they separated the teacher

00:25:22.710 --> 00:25:25.369
from the student. Or perhaps they recognize that

00:25:25.369 --> 00:25:28.150
the message of human -centric leadership is universal,

00:25:28.289 --> 00:25:30.589
even if the application of it happens in controversial

00:25:30.589 --> 00:25:33.789
spaces. So we have covered the globetrotting

00:25:33.789 --> 00:25:36.769
childhood, the anthropology degree that changed

00:25:36.769 --> 00:25:40.089
everything, the ad agency days, the viral TED

00:25:40.089 --> 00:25:43.329
talk, the whole library of books, and the institutional

00:25:43.329 --> 00:25:46.529
clout. It is quite a resume, a very unconventional

00:25:46.529 --> 00:25:49.170
one. When you look at it all together. What is

00:25:49.170 --> 00:25:51.269
the through line for you? What connects the kid

00:25:51.269 --> 00:25:53.529
in Johannesburg to the instructor at Columbia?

00:25:53.710 --> 00:25:56.390
For me, it is the role of the observer. The observer.

00:25:56.569 --> 00:25:58.710
Yes. Whether he was a kid trying to figure out

00:25:58.710 --> 00:26:01.490
the rules of a new school in a new country or

00:26:01.490 --> 00:26:04.289
an anthropologist studying a culture or a consultant

00:26:04.289 --> 00:26:07.289
studying a corporation, Sinek has always been

00:26:07.289 --> 00:26:09.390
the one standing slightly outside the circle

00:26:09.390 --> 00:26:12.589
looking in. And pointing out the patterns that

00:26:12.589 --> 00:26:14.930
the people inside the circle can't see. Exactly.

00:26:15.009 --> 00:26:16.970
The people inside are too busy. They're too busy

00:26:16.970 --> 00:26:19.549
playing the finite game. They're too busy worrying

00:26:19.549 --> 00:26:21.849
about the quarterly earnings or the daily metrics.

00:26:22.349 --> 00:26:24.549
Cynics stands outside and says, wait a minute.

00:26:24.650 --> 00:26:27.309
Look at the biology. Look at the trust. Look

00:26:27.309 --> 00:26:30.470
at the why he simplifies the complexity of human

00:26:30.470 --> 00:26:33.230
behavior into something we can actually understand

00:26:33.230 --> 00:26:36.589
and use. He creates a map. The golden circle

00:26:36.589 --> 00:26:39.230
is a map. The circle of safety is a map. The

00:26:39.230 --> 00:26:41.970
infinite game is a map. He is a cartographer

00:26:41.970 --> 00:26:44.349
of leadership. That is a great way to put it.

00:26:44.589 --> 00:26:46.910
A cartographer of leadership. And that ties back

00:26:46.910 --> 00:26:49.890
to why he calls himself an optimist. An optimist

00:26:49.890 --> 00:26:52.829
isn't someone who ignores reality. An optimist

00:26:52.829 --> 00:26:55.309
is someone who sees a path forward, is someone

00:26:55.309 --> 00:26:57.609
who believes that if we understand the rules

00:26:57.609 --> 00:27:00.390
of the game, the real rules, the human rules,

00:27:00.569 --> 00:27:02.829
we can build organizations that actually work

00:27:02.829 --> 00:27:05.109
for people. And that is a message that clearly

00:27:05.109 --> 00:27:07.869
resonates whether you are running a startup or

00:27:07.869 --> 00:27:10.390
a superpower. Before we wrap up, I want to leave

00:27:10.390 --> 00:27:12.369
our listener with a thought. We talked about

00:27:12.369 --> 00:27:15.039
the infinite game. The idea that you're not playing

00:27:15.039 --> 00:27:17.500
to win. You're playing to keep playing. Yes.

00:27:18.200 --> 00:27:22.140
A really powerful idea. So, listener, here is

00:27:22.140 --> 00:27:25.160
the question for you today. If Cynic's philosophy

00:27:25.160 --> 00:27:28.119
is about the long haul playing for the infinite

00:27:28.119 --> 00:27:30.779
game rather than the short -term win, how does

00:27:30.779 --> 00:27:33.019
that apply to your own career right now? It is

00:27:33.019 --> 00:27:35.519
a vital question. A tough one to answer, honestly,

00:27:35.599 --> 00:27:38.880
sometimes. Are you making decisions today just

00:27:38.880 --> 00:27:42.380
to win the week? To get the promotion? to beat

00:27:42.380 --> 00:27:44.920
the guy in the next cubicle? Or are you making

00:27:44.920 --> 00:27:46.920
decisions that allow you to stay in the game?

00:27:47.599 --> 00:27:49.839
Are you building the relationships and the reputation

00:27:49.839 --> 00:27:52.220
that will matter 10 years from now? Are you focused

00:27:52.220 --> 00:27:54.400
on the score or are you focused on the purpose?

00:27:54.700 --> 00:27:57.440
Because the score resets every quarter. The purpose

00:27:57.440 --> 00:27:59.980
endures. That is the takeaway. Stop looking at

00:27:59.980 --> 00:28:02.039
the scoreboard and start looking at the horizon.

00:28:02.339 --> 00:28:04.859
And remember, understanding your own why is the

00:28:04.859 --> 00:28:06.819
first step to staying on that path. It's the

00:28:06.819 --> 00:28:09.599
fuel for the infinite game. This has been a fascinating

00:28:09.599 --> 00:28:12.390
deep dive. From Wimbledon to the world stage,

00:28:12.769 --> 00:28:16.609
Simon Sinek's journey is a master class in observation

00:28:16.609 --> 00:28:20.130
and communication. It truly is. A lesson in finding

00:28:20.130 --> 00:28:22.210
your niche. Thanks for diving in with us. We

00:28:22.210 --> 00:28:24.089
will catch you on the next one. Keep asking why.

00:28:24.250 --> 00:28:26.430
And keep playing the infinite game. See you next

00:28:26.430 --> 00:28:26.650
time.
