Welcome back to the Deep Dive. I hope you are
ready to swim because today we are opening a
file on a figure who, quite honestly, feels like
he is everywhere right now. Oh, everywhere. That's
not an exaggeration. You open your LinkedIn feed.
There he is. You walk into a corporate boardroom.
Someone is quoting him. You go on YouTube and
you see that, you know, that slightly grady video
of a guy in a suit with a flip chart and a cheap
marker just completely changing the way millions
of people think about business. It is genuinely
hard to exist in the modern professional world
without tripping over Simon Sinek. It really
is. He has become part of the cultural furniture
of leadership. Exactly. Yeah. And that is why
we need to talk about him. But here's the thing
that really triggered this specific deep dive
for me. OK. Usually when we cover these massive
business gurus, they fit a very specific, very
rigid mold. They're the ex -CEO of General Electric.
Right. The Wharton MBA. They're a tenured professor
of economics at Harvard. They're quantitative
analysts who crunched the numbers and, you know,
found the secret sauce. But Simon Sinek. He is
none of those things. No, he definitely breaks
the mold. He's an outlier in, I think, the best
possible way. And I think the best place to start
is with how he actually defines himself. Because
in the source material we have in front of us,
the biographical review, the publication history,
he doesn't call himself a management consultant.
Nope. He doesn't call himself a strategist. Right.
If you look at his own bio, the title he gives
himself is optimist. An optimist. With a capital
O. A capital O. It is a defined professional
title for him. It's on his business card. I think
so. And I think for a lot of people that might
sound a little, well, a little fluffy. Yeah,
a bit. It sounds like something you put in your
Instagram bio, not on your tax return. But our
mission today is to peel back that label and
look at the actual mechanics underneath. Because
Sinek isn't just selling good vibes. He has built
a massive global empire based on a very specific,
very rigorous way of looking at human behavior.
And that's the hook, right? We're going to dig
into the fact that his background isn't in business
at all. It's in anthropology. The absolute key
to understanding him. We're going to look at...
How a guy who's studied cultural rituals and
human tribes ends up advising the U .S. military,
the Rand Corporation, and some of the biggest
companies on Earth. It's a wild trajectory. And
we aren't going to shy away from the business
of being Simon Sinek either. No. We are going
to look at the evolution of his bibliography,
his institutional ties, and yes, even some of
the controversies that have popped up along the
way, specifically regarding government contracts.
It is a fascinating story. From a kid moving
across the globe to a global thought leader.
So let's start at the very beginning. Let's do
it. Because to understand the why guy, you have
to understand where he actually came from. And
where he came from isn't a simple answer. If
you look at his early biography, the geography
is all over the map. Literally. So, Simon Oliver
Sinek, born October 9th, 1973. In Wimbledon,
London, England. So he starts his life across
the pond. Right. A proper English start. But
he doesn't stay there. And this is the part that
really jumped out at me as we were prepping this.
His childhood map is just, it's incredibly erratic.
It's nomadic. He's born in Wimbledon. Then the
family moves to Johannesburg, South Africa. Right.
Then back to London. Then over to Hong Kong.
And then finally, they settle in the United States.
Just pause and think about that itinerary for
a second. We're talking about the 1970s and 80s
here. Yeah. These aren't just different cities.
They are entirely different universes culturally.
You have post -imperial Britain. You have South
Africa during the apartheid era. A very intense
place to be. Absolutely. Then you have Hong Kong,
which was this frenetic, high -energy British
colony on the edge of communist China. And then
you land in the suburbs of New Jersey. That is
a serious amount of cultural whiplash for a kid.
I can't even imagine. It is. But think about
what that does to a developing brain. When you
are the new kid that many times in that many
different environments, you never fully belong
to any of them. Right. You are always the outsider.
You are always the other. You're the third culture
kid. That's the term for it, isn't it? Exactly.
And when you are the outsider, you develop a
survival skill. Observation. You have to. You
have no choice. If you want to survive socially.
on a playground in Johannesburg and then a year
later on a playground in Hong Kong, you have
to figure out the rules fast. You have to watch.
Who's in charge here? Who is the leader here?
How do they show respect? What gets you punished?
What gets you rewarded? You have to decode the
tribe just to get through lunch. Precisely. You
become a watcher of human behavior by necessity.
You learn to spot the patterns that the locals,
the people who have lived there their whole lives,
don't even see because they are too close to
it. So in a way, his childhood forced him to
become an amateur anthropologist before he even
knew what the word meant. I don't think it is
a coincidence at all, not one bit, that when
he finally got to college, that is exactly what
he chose to study. Let's look at the education
path, because this is where the foundation is
poured. He settles in the U .S., goes to high
school in New Jersey, Northern Valley Regional
High School at Demarest, specifically. Right.
Go Norseman. Graduates in 1991. Mm -hmm. And
then he heads to Brandeis University in Massachusetts.
Now, if you are planning to become a massive
business consultant, usually you'd expect this
part of the story to be, and then he enrolled
in the Wharton School of Business or he majored
in economics. But he didn't. He earned a B .A.
in cultural anthropology. This, to me, is the
Rosetta Stone for his entire career. If you skip
this fact, you miss the entire point of Simon
Sinek. I agree completely because cultural anthropology
is not the study of spreadsheets. It isn't the
study of profit margins. It is the study of humans.
It is the study of why groups of people behave
the way they do. It looks at symbols, rituals,
social structures, hierarchies and myths. Right.
So for the listener who might not be familiar
with the field, an anthropologist looks at a
group, say a remote tribe in the Amazon and asks,
what holds this group together? Why do they trust
their leader? What are their taboos? All these
like. Invisible forces. Exactly. And Sinek's
genius was that he took that lens, that anthropological
lens, and he turned it on the modern corporation.
He realized that a company like Microsoft or
Apple or American Airlines isn't a machine. It's
a tribe. It's a group of primates trying to survive
and thrive together. So while other consultants
are looking at the P &L statement, Sinek is looking
for the rituals. He's looking for the signs of
safety. He is looking at the biology of belonging.
If you listen to his language, even today it
is very tribal. He talks about the circle of
safety. He talks about servant leadership. He
talks about trust as a biological reaction, not
a contractual obligation. That is pure anthroposophical.
It's straight out of the textbook. It explains
why his advice feels so different. It's not increase
efficiency by 10 percent. Yeah. It's make your
people feel safe so they can do their best work.
It's a completely different paradigm. It grounds
business and humanity. Yeah. But interestingly
enough, he didn't go straight from Brandeis to
the TED stage. He took a detour that I think
is equally important. Right. The law school era
or the almost lawyer era, I should say. The almost
lawyer era. Yeah. He studied law at City University
London. So back to London again. Back to London.
And even though he didn't become a practicing
barrister. This training is crucial. Why is that?
Law is about logic. It is about structure. It
is about taking a messy, complex set of facts
and organizing them into a coherent, persuasive
argument. Okay, I see. So you have the observer
from the anthropology side, the person who sees
the human patterns. Yes. And then you have the
advocate from the law side, the person who can
build a clear, logical case around what he's
seeing. And those two things combine to create
a very, very powerful communicator, someone who
can see a deep human truth and then structure
a logical, irrefutable argument around it. Which
leads us perfectly to his first real career,
advertising. The industry of persuasion. He worked
at some serious agencies, Euro, RSCG, and Ogilvy
& Mather in New York. Ogilvy? Yeah. These aren't
small shops. These are the giants of Madison
Avenue. And working at a place like Ogilvy implies
a few things. I mean, it's the Mad Men legacy,
right? Totally. You are trained to take a complex
product or a complex message and distill it down
to one simple emotional hook. You have to be
able to draw it on a napkin. You have to be able
to say it in a tagline. You aren't selling the
features of the car. You're selling the feeling
of the open road. Exactly. And if you look at
Sinek's most famous concept, the golden circle,
it is essentially a perfect piece of ad copy.
It is a diagram. It is visual. It is simple.
It is sticky. He took deep anthropological concepts
about human motivation and packaged them with
the slickness and clarity of a high -end ad executive.
Wow, that's a great connection. I hadn't thought
of it that way. It's the perfect marriage of
his skills. So he spends time in the ad world.
He learns the trade of messaging. He eventually
launches his own consultancy, Cynic Partners.
But the moment everything changes, the tipping
point where he goes from guy with a consultancy
to Simon Sinek is 2009. 2009, the year the why
went global. He publishes the book, Start With
Why, How Great Leaders Inspire Everyone to Take
Action. And critically, he gives a TEDx talk.
We have to pause on that TED Talk because the
source material notes that this is one of the
most viewed TED Talks of all time. We are talking
tens of millions of views. It's staggering. And
if you go back and watch it, it is strikingly
low tech. Oh, it's not flashy at all. There are
no bells and whistles. The audio is a little
echoey. He's wearing a slightly ill -fitting
suit. He doesn't have a PowerPoint. He doesn't
have lasers. He has a flip chart and a Sharpie.
And he drops the microphone at one point, doesn't
he? Or the marker. Something clatters to the
ground. Yes, it's very raw. But that rawness
is part of why it worked. And we have to look
at the context of 2009. Oh, absolutely. The Great
Recession. The world had just fallen off a cliff.
The global financial system had nearly collapsed.
Trust in corporations was at absolute zero. People
were angry. They were scared. They felt betrayed
by their leaders. They felt that business was
just about greed. And here comes this guy with
a simple marker standing there saying, We are
doing it all wrong. It's not about money. It's
about why. The timing was just perfect. It was
the exact message people needed to hear at that
moment. It was a life raft. Let's break down
that concept, the golden circle, because it is
the foundation of everything else he does. Right.
So for anyone listening, just visualize a target.
Yeah. Three concentric circles. Like a dartboard.
Exactly. The outside ring is what, the middle
ring is how, and the center bullseye is why.
Okay. Sinek argues that every single organization
on the planet knows what they do. That's the
easy part. We make computers. We sell legal services.
We manufacture cars. Everyone knows the what.
And some know how they do it. That's your value
proposition. We have the best proprietary process.
We use the finest materials. That's the how,
the differentiator. But very, very few know.
Why they do it. And by why, he doesn't mean to
make a profit. That's a result. He's very clear
on that. He means, what is your cause? What is
your belief? Why does your organization exist
in the first place? Why do you get out of bed
in the morning? And why should anyone care? And
his big argument is that most leaders communicate
from the outside in. They start with the what?
All the time. Here is our new car. It has great
gas mileage and leather seats. Buy it. But the
inspiring leaders. The ones who changed the world,
the Apples, the Martin Luther King Jrs, the Wright
brothers, they communicate from the inside out.
They start with the why. The famous Apple example.
Instead of, we make great computers, it's...
It's everything we do, we believe in challenging
the status quo. We believe in thinking differently.
That's the why. Okay. The way we challenge the
status quo is by making our products beautifully
designed and simple to use. That's the how. And
then... We just happen to make great computers.
That's the what? Want to buy one? It's a total
reversal. And it feels completely different.
It feels like an invitation, not a sales pitch.
And he connects this back to biology, right?
This isn't just a linguistic trick. This is the
anthropology coming back in a huge way. He argues
that the why and the how correspond to the limbic
brain. OK, the limbic brain. The part of the
brain that controls feelings like trust and loyalty.
It's also the part of the brain that has no capacity
for language. Right. Which is why when you ask
someone, why do you love your spouse? Yeah. They
can't give you a bulleted list of reasons. They
can't. They just say, I don't know, it just feels
right. Exactly. That is the limbic brain speaking.
That's your gut feeling. So if you want to influence
behavior, if you want loyalty, you have to speak
to the limbic brain. You have to speak to the
why. But if you only talk about features and
benefits, you were just talking to the neocortex.
The rational brain. Yeah. You might get a transaction,
but you won't get loyalty. People don't buy what
you do. They buy why you do it. That concept
just exploded. It resonated so deeply because
I think people were starving for meaning in their
work, especially after 2008. They were desperate
for it. But what's interesting to me is that
Sinek didn't stop there. He didn't just become
the why guy and retire. No, his thinking evolved.
And if you look at his bibliography chronologically,
you can see him expanding the theory, building
a whole universe around this one core idea. Let's
walk through that library because it tells a
story of its own. 2009 is start with why. Then
we have a... Bit of a gap until 2014. And then
he drops Leaders Eat Last. Leaders Eat Last.
Why some teams pull together and others don't.
Now look at the shift in focus. It's a different
lens. The first book was about the individual
leader or the brand how to inspire action outward.
This book is about the team. It's about the internal
culture. How do you inspire action inward? The
title itself is a great story. Where did that
come from? It comes from a conversation he had
with a Marine Corps general. He asked him, what
makes the Marines so effective? Why are they
so tight knit? Why would they risk their lives
for each other? And the general simply said,
officers eat last. It's a literal rule in the
chow hall. It is. When the Marines line up for
food, the most junior recruit eats first. The
senior general eats last. And if the food runs
out, the general goes hungry. Wow. That is a
powerful symbol. It is the physical manifestation
of leadership. It signals to the tribe, I will
sacrifice my comfort for your survival. Your
well -being comes before my own. And Sinek argues
that this creates what he calls the circle of
safety. Yes, the circle of safety. When we feel
safe, when we know our leader has our back, our
biology changes. Our cortisol levels drop. Cortisol
is the stress hormone. The fight or flight chemical.
Right. If you are constantly worried that your
boss is going to fire you to save a nickel or
throw you under the bus in a meeting to look
good. Which happens all the time. You are dripping
with cortisol. You are in fight or flight mode.
You can't innovate. You can't trust. You are
just trying to survive the day. But if the leader
eats last, if they prove they are there to protect
you, the cortisol drops and oxytocin kicks in.
The bonding chemical. The love drug, they sometimes
call it. It facilitates empathy. trust, generosity.
And when that happens, the team naturally pulls
together to face external threats instead of
fighting each other internally. Sinek is basically
telling modern CEOs that they are failing because
they are ignoring our basic primate programming.
Leaders Eat Last was a huge hit. It made the
New York Times and Wall Street Journal bestseller
lists. It cemented him as a management expert,
not just a marketing guy. For sure. Then in 2016,
we got a bit of a curveball. Together is Better,
a little book of inspiration. A little book.
This one feels different. It's illustrated. It's
almost like a fable or a children's book for
adults. It is, and it suggests a move toward
accessibility. He wanted something that wasn't
a dense 300 -page business book. He wanted something
you could give to a graduate or leave on a desk
in the office. It's the optimism brand distilled
into a pure, shareable format. It's snackable
content. And then in 2017, find your why. This
was the necessary tactical follow -up. It was
almost inevitable. Because after start with why,
the number one question he must have gotten was,
Okay, Simon, I get it. The why is important.
But how do I find mine? Right. It's easy for
Apple. They have Steve Jobs. But what if I'm
a mid -level manager at a paper company? What's
my grand, world -changing why? Exactly. So Find
Your Why is a practical guide. It's a workbook.
It has exercises and steps. It marks the shift
from philosopher to trainer. He is giving people
the shovel to do the digging themselves. It's
the application. It's the application. And then
the most recent major work in our source stack
is 2019's The Infinite Game. And honestly, I
think this is his most intellectually ambitious
concept. I agree. This is where he steps out
of just team dynamics and looks at macro strategy.
This is him thinking on a much grander scale.
Let's unpack the title. What is an infinite game?
The concept comes from a scholar named James
P. Kars. Sinek takes that academic idea and applies
it to business and capitalism. Basically, there
are two types of games, finite games and infinite
games. A finite game is like football or chess.
Right. Known players. Fixed rules. Agreed upon
objective. There is a klong or a finish line.
At the end of the game, someone has more points.
They win, you lose. Game over. Simple. Very clear.
But an infinite game has known and unknown players.
The rules are changeable. And the objective is
not to win, but to keep playing. To perpetuate
the game. Like marriage. Or friendship. You don't
win a marriage. Exactly. You don't win friendship.
The goal is to keep the relationship healthy
and strong so it continues. And Sinek argues
that business is an infinite game. Yes. There
is no such thing as winning business. You can't
win global commerce. The game existed before
your company and it will exist after. But the
problem is most executives lead as if they are
playing a finite game. They are obsessed with
beating the competition this quarter, being number
one. in their category and cynic says that mindset
is destructive if you play a finite game trying
to win the quarter in the middle of an infinite
game business you make bad choices you cut r
d to make your numbers look better you squeeze
your employees on salaries and benefits you degrade
your product quality just to hit a number you
might win the quarter but you eventually run
out of the will or the resources to keep playing
you burn down the house to stay warm for a night
Precisely. In the infinite game, the goal is
resilience. The goal is to build an organization
that can survive the ups and downs and outlast
the others. It ties everything together. It does.
You need a why to have the stamina for an infinite
game. You need leaders eat last to have the team
cohesion to weather the storms. And you need
the infinite mindset to navigate the strategy.
It's a very complete ecosystem of thought. He's
really built a whole world. But speaking of ecosystems,
we need to talk about the business Sinek has
built around himself. Because he isn't just writing
books in a cabin somewhere. Oh, no. He's running
a machine. A well -oiled machine. And the sources
give us a glimpse into how that machine is structured.
First off, publishing. In November 2018, Publishers
Weekly reported that Sinek started Optimism Press.
Which is an imprint of Penguin Random House.
That is a big deal. A really big deal. Having
your own imprint means you aren't just an author.
You are a curator. You are a kingmaker. He is
selecting other voices that align with his worldview
to elevate under his brand. It's a huge expansion
of influence. And then there's the optimism company.
A digital learning platform. This is the scale
play. Right. He realized he can't fly to every
company in the world to give a speech. So he
built a platform to train people digitally. It
institutionalizes the optimist title. It turns
it from a personal brand into a corporate entity.
But what really caught my eye in the research,
and this is where we get into the institutional
ties section of our outline, is that he's not
just operating in the corporate training world.
He has some serious academic and policy credentials.
This is a crucial distinction. There are a lot
of motivational speakers out there, a lot. But
very few of them are instructors at Columbia
University. Right. He is an instructor of strategic
communications at Columbia. That is Ivy League.
That is serious academic weight. And even more
significant, in my view, is his connection to
the Rand Corporation. Yes. The Rand Corporation.
For listeners who don't know, what is Rand? This
isn't some fly -by -night consulting firm. No.
Rand is a global policy think tank. They were
originally formed to offer research and analysis
to the U .S. Armed Forces after World War II.
They deal with national security, international
affairs, law, business, health. They are the
heavy hitters of strategic thinking. The people
who advise governments on incredibly complex
issues. The very same. And Sinek is listed as
an adjunct staff member. That validates his standing
in a way that being a New York Times bestseller
doesn't. Completely different kind of validation.
It suggests that his ideas about leadership aren't
just fluff. They have strategic utility. When
you are talking about how to lead a military
unit or a government agency, the stakes are different
than selling sneakers. And Sinek has managed
to bridge that gap. He speaks at the UN Global
Compact Leaders Summit. He's in these rooms where
global decisions are being discussed. Which makes
the next part of our deep dive even more interesting.
Because when you operate at that level, when
you work with governments and massive institutions,
things can get... I certainly can. The optics
get very tricky. We need to talk about the ICEE
controversy. This is a specific event reported
in the sources, specifically around June 2018.
Right. So June 2018, the Young Turks reported
on a contract. The amount was $98 ,000. And the
client was U .S. Immigration and Customs Enforcement,
or ICEE. And the nature of the contract was for
leadership training. Correct. It was a no -bid
contract, and it is important to note the facilitation
here. The training was provided by Ernst & Young.
So let's break this down factually, just based
on what's in the sources. Ernst & Young is a
massive professional services network, one of
the big four. They do consulting, accounting,
everything. Yes. And typically, large government
agencies like ICE have standing multi -year,
multi -million dollar contracts with firms like
Ernst & Young to provide all sorts of training
and services. So Sinek's involvement was likely
part of a broader package. It was likely a specific
request fulfilled through that existing channel.
It's not necessarily Simon Sinek knocking on
ICE's door saying, hire me. It's more likely
ICE telling Ernst & Young. We want leadership
training. Get us the Y guy. But the headline,
$98 ,000 contract with IC. That lands differently
depending on the political climate. And 2018
was a very, very heated time regarding immigration
policy in the U .S. It was. The family separation
policy was miniature news. And this highlights
the tension we mentioned earlier. When you position
yourself as a leadership expert and your mission
is to help leaders inspire action and create
safety, who do you work with? Right. Do you only
train leaders of organizations you agree with
politically? Or do you believe that every organization
needs better leadership? That is the central
question. From a strictly professional standpoint,
leadership training is a service. It is a commodity.
Corporations buy it, nonprofits buy it, and yes,
government agencies, including law enforcement
and border control, buy it. They have managers
and teams just like anyone else. And arguably,
one could say that agencies with high -stress,
high -stakes environments need concepts like
leadership and circle of safety more than anyone.
That is one perspective. If you believe in the
leaders eat last philosophy, that leaders should
protect their people and create a moral circle,
then teaching that to a government agency could
be seen as an attempt to improve the culture
from within. But on the flip side, from another
perspective, taking the money can be seen as
an endorsement or at least a normalization of
the agency itself and its policies at the time.
Precisely. And that is why it became a news story.
When you are a public figure preaching optimism
and why, your client list becomes a statement
of its own whether you intend it to be or not.
It's a fascinating case study in the business
of philosophy. You can have these pure ideals,
but when they hit the real world of government
contracting, it gets messy. The lines get blurred.
It does. And yet, looking at the source material,
this didn't seem to derail his career. He continued
to publish, continued to speak, continued to
build the optimism company. Which suggests that
his core audience, the people playing the infinite
game, Maybe he saw it as just another move on
the board. Or maybe they separated the teacher
from the student. Or perhaps they recognize that
the message of human -centric leadership is universal,
even if the application of it happens in controversial
spaces. So we have covered the globetrotting
childhood, the anthropology degree that changed
everything, the ad agency days, the viral TED
talk, the whole library of books, and the institutional
clout. It is quite a resume, a very unconventional
one. When you look at it all together. What is
the through line for you? What connects the kid
in Johannesburg to the instructor at Columbia?
For me, it is the role of the observer. The observer.
Yes. Whether he was a kid trying to figure out
the rules of a new school in a new country or
an anthropologist studying a culture or a consultant
studying a corporation, Sinek has always been
the one standing slightly outside the circle
looking in. And pointing out the patterns that
the people inside the circle can't see. Exactly.
The people inside are too busy. They're too busy
playing the finite game. They're too busy worrying
about the quarterly earnings or the daily metrics.
Cynics stands outside and says, wait a minute.
Look at the biology. Look at the trust. Look
at the why he simplifies the complexity of human
behavior into something we can actually understand
and use. He creates a map. The golden circle
is a map. The circle of safety is a map. The
infinite game is a map. He is a cartographer
of leadership. That is a great way to put it.
A cartographer of leadership. And that ties back
to why he calls himself an optimist. An optimist
isn't someone who ignores reality. An optimist
is someone who sees a path forward, is someone
who believes that if we understand the rules
of the game, the real rules, the human rules,
we can build organizations that actually work
for people. And that is a message that clearly
resonates whether you are running a startup or
a superpower. Before we wrap up, I want to leave
our listener with a thought. We talked about
the infinite game. The idea that you're not playing
to win. You're playing to keep playing. Yes.
A really powerful idea. So, listener, here is
the question for you today. If Cynic's philosophy
is about the long haul playing for the infinite
game rather than the short -term win, how does
that apply to your own career right now? It is
a vital question. A tough one to answer, honestly,
sometimes. Are you making decisions today just
to win the week? To get the promotion? to beat
the guy in the next cubicle? Or are you making
decisions that allow you to stay in the game?
Are you building the relationships and the reputation
that will matter 10 years from now? Are you focused
on the score or are you focused on the purpose?
Because the score resets every quarter. The purpose
endures. That is the takeaway. Stop looking at
the scoreboard and start looking at the horizon.
And remember, understanding your own why is the
first step to staying on that path. It's the
fuel for the infinite game. This has been a fascinating
deep dive. From Wimbledon to the world stage,
Simon Sinek's journey is a master class in observation
and communication. It truly is. A lesson in finding
your niche. Thanks for diving in with us. We
will catch you on the next one. Keep asking why.
And keep playing the infinite game. See you next
time.