AI transcript
– What was that aha moment for you?
I see something the rest of the world doesn’t see yet.
– Yeah.
– Well, I mean–
– Simon Sinek, popular at 50 million views on it.
– My initial conclusion was,
the good partnerships, you love the partner
and they’re offering you the ability
to expand your vision.
Though it won’t be perfect, no relationship is,
you still love coming to work
because you feel like you’re still advancing
the greater good in building this business.
Those are the partnerships we should be pursuing.
Discomfort is one of those things
that to learn to be uncomfortable
is nobody who’s ever achieved anything in the world
did it smoothly.
We all came close to zero if not hitting zero first.
And when you’re coming up to a stranger,
can you help me get out of this?
My answer is always the same as,
why would I get into mud with a stranger?
– Right. – I don’t know you.
Go ask somebody who loves you.
It’s safer to be vulnerable with me
because I’m a stranger.
It’s hard to be vulnerable
with somebody who actually knows me.
I don’t know the three most important words
that a young entrepreneur can ever learn.
It’s your story, it’s also my story.
I thought I had to have every answer
and if I didn’t, I thought I had to pretend that I did.
Let me tell you, you are who you are
and the rest of your life is simply an opportunity
to live in balance with that wire.
I’ll show you another way to find your wire.
Which is, and this is.
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Happy Father’s Day.
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– Simon, thank you for joining me.
– Thanks for having me.
– So great to have you on.
I’ve been a fan from afar.
– Thank you.
– Watching what you’ve done over the years
and your content and preparation for this interview.
I had to go and just check the numbers
of how you’ve blown up over the years.
I mean, it’s insane, so 56 million views or so
on Start With Why.
Did you have any idea it was gonna be that big?
– I mean, of course not.
It’s winning the internet lottery.
I knew that the talk resonated
because it wasn’t the first time I gave it.
I’d been giving the long version of that talk
for a few years.
I knew the content was resonant with people.
I knew it was a different way of seeing the world.
But of course, I could never have known
that it would do what it did.
Combined with the fact that the audio quality
is terrible and the video quality is terrible
and it’s living proof that it slick comes second.
– Yeah, I look back on that.
It’s not even HD.
– That’s terrible.
– Yeah, my microphone breaks in the middle of my talk.
– Yeah.
There’s a handful of books that have really changed
my thinking, especially around entrepreneurship
and leadership, zero to one.
There’s a handful of ones where I’m just like,
oh wow, there was some great insight there that happened.
Where did this come from?
Where was that aha moment for you where you’re like,
I see something that the rest of the world doesn’t see yet.
– Like most of these ideas, they’re rarely an aha moment.
It’s more like evolutionary steps.
The realization after many steps and this was no different.
I came from an advertising and marketing background
and I was always curious why some marketing worked
and some marketing didn’t.
I wasn’t the creative teams ’cause I could have
the same creative team make good stuff and bad stuff.
And it wasn’t just the clients.
I had clients that made good stuff and bad stuff.
And so I looked at sort of the great marketing
that I admired and I recognized that there was a pattern
that it all started with why they did what they did.
And I articulated the concept way back then
just to explain why some marketing
worked and some marketing didn’t.
That’s all it was.
And the original model was why, what, how.
The definitions were the same as they are now,
but it was why, what, how.
And I used to use that.
I started my own business and I used to use that
as my sort of pitch, you know.
And it wasn’t until much later I went to an event
at this black tie affair and I was just sort of
coincidentally seated next to somebody whose dad
was a neuroscientist when we just started talking,
making small talk.
Yeah, and she was telling me about Neuroscience 101.
And I was curious about it and came back
and started like Googling like crazy.
And I realized this little model that I had discovered
and the neuroscience perfectly overlapped.
I hadn’t discovered why marketing worked,
I discovered why people do what they do.
So I reached out to a famous neuroscientist
named Peter Weibrow, who was the head
of the Semmel Institute at UCLA,
which is the largest neuroscience institute in the world.
I don’t know how I got hold of him, but I did.
And I basically said, I need you to look at this stuff.
I’m gonna say this is related to neuroscience.
I need this blessed.
Yes.
So I like went to his house for a weekend,
just basically talk nonstop.
And I came in on Sunday morning and he was like fidgety.
And I’m like, what’s the matter?
He goes, it doesn’t match the neuroscience.
I’m like, well, what do you mean?
He goes, you need to switch what and how.
I’m like, done.
Yeah.
Maybe came why, how, what?
Yeah.
The definitions are always the same,
but to match the neuroscience of how brain work,
that’s what it was.
And then I started to realize that this thing had power.
At a later point, it saved me because I lost my passion
for my own work and hit sort of a really dark period.
And I realized that I knew what I did.
I knew how I did it, but I didn’t know why.
So these things all sort of collided.
Personal depression plus my exploration here.
And it all sort of came together.
I have at least a half dozen friends right now
that have landed in what they thought
was gonna be their dream job.
It typically happens via an acquisition.
It’s a tech entrepreneur.
They get acquired by a big company.
They’re now inside the belly of the beast
of something large.
And they have a couple of sayings.
It’s like vest in peace.
Or it’s just like, you’re just vesting
and kind of showing up and quiet quitting, right?
Which I’m sure you’ve heard about.
What’s going wrong there?
What’s happening?
Why are they feeling this way?
You’re asking something that’s,
something that happens two or three steps prior.
Okay.
The number of young, idealistic entrepreneurs
who start businesses and ethics matter to them
and treating their people right matters to them
and culture matters and all the things
that I write and talk about matters to them.
And they build these beautiful businesses
and then they sell them to the highest bidder,
not to the company that believes in their values
and has to maintain the culture, the highest bidder.
Right.
And the company goes to shit.
They change the ingredients of the product
because they go for something cheaper, et cetera, et cetera,
et cetera, you go down the line.
And they can rationalize it because they cashed out big.
They can rationalize that, no, we did it right.
And they didn’t.
That’s, be honest, they didn’t.
Why not take a little less money and sell it
to the right company who believes in the values
rather than just sell it to the highest bidder?
And so if they’re stuck in a place
where they don’t wanna be there,
well, that was their choice.
Like they chose that partnership.
That’s like marrying somebody just ’cause they’re pretty.
Yeah.
Right?
And then complaining that my marriage isn’t working
and we don’t get along.
I’m like, yeah, I don’t know how many marriage advice for you.
It’s hard though too ’cause you have stakeholders, right?
Well, that is another thing.
It’s the same trauma, which is, you know,
so many entrepreneurs who are looking for capital,
they take the biggest capital
from the most famous venture capitalist,
not less capital from the right venture capitalist.
That’s right.
So they chose their own partners
and then they’re surprised whether partners
are applying massive amounts of pressure on them
to make decisions that they don’t wanna make.
Yeah.
I don’t have a lot of sympathy, you know?
And we have reached the point now
where, and I can’t remember the statistic,
it’s overwhelming.
It’s something like 80% of companies are, you know,
venture capital or private equity backed.
And so we used to mock the public markets
that the pressure exerted by Wall Street
would force CEOs to make decisions
they knew were bad for their companies.
And we’re now at a point where private companies
are basically functioning like public companies
where the external pressures are so great.
That’s right.
That the number of young, brilliant,
fantastic, talented CEOs getting fired from their own companies.
I have a friend who just got fired from her own company
because she didn’t have control of it.
Yeah.
And she couldn’t make decisions.
They fired her because she was trying
to do the quote unquote right thing and follow the vision.
And they wanted to do the thing that made it prettier
to sell in a short period.
There’s an element of like, you made your bed.
And so there’s even a degree of,
look, I’m not in their position,
but there’s even a degree of irresponsibility.
Yeah.
There’s no choice to take the deal.
And now you’re dissatisfied with the deal.
You have sort of sellers remorse.
And so you’re going to quiet quit because you’re pissed off.
I’m like, they didn’t do anything wrong.
Right.
You took the deal.
I think there’s some soul searching to be done
in business writ large,
which is who we take money from and who we sell to.
Yeah.
Because I think a lot of good companies
actually don’t survive the founders
because of who we sell them to.
I can almost count it like clockwork
because I’ve seen so many of these deals
and I know what it is.
It’s a three year vest.
When you sell the company,
they put golden handcuffs on you for three years
and you can almost just mark the date.
And then you see a founder being like,
I’m leaving and it’s of course
right at the three year anniversary, right?
And they’re out.
And then if they were holding it together
with any duct tape or whatever else,
like everything seems to fall apart from there.
Unfortunately.
Good partnerships.
You love the partner.
You love the buyer.
And they’re offering you some sort of ability
to expand your vision.
You couldn’t do yourself,
which is why you took the deal.
That’s right.
Fundamentally, you come to an arrangement
where even though you have a boss now
and you didn’t have one before,
that there’s a degree of independence you have
to build this brand, which is what they want as well.
And though it won’t be perfect, no relationship is,
you fundamentally still love coming to work
because you feel like you’re still advancing
the greater good in building this business.
Right.
So those are the partnerships we should be pursuing.
Yes.
Yeah, that makes a ton of sense.
It’s almost like feel for the fire at that point.
Like you’re joining forces with someone
to help you expand and grow a lot faster.
What about individuals that are,
I see as individual contributors to an organization
and I see some of these resumes
when I’m looking to hire, say an engineer,
and you see bouncing around.
You see bouncing around
between different employment opportunities.
What advice do you give them
and how do you help coach someone
through finding their why?
Well, there’s a couple of different questions there.
You and I, when we were younger,
even if we hated our job,
we would never dream of quitting in less than one year.
Oh, 100%.
We couldn’t.
It would look so bad.
And we all knew that if you did that,
it would destroy your resume.
Yes.
It would create a bad narrative
about what kind of employee you were.
And I mean, it would have to be pretty toxic
for you to leave it under a year, right?
And so we held our nose and we made it to a year.
And this predominantly younger generation,
though it’s not exclusive,
but predominantly younger generation
is very comfortable quitting quickly
and sometimes for not good reasons.
And I’ve seen it happen,
which is the young people who are so confrontation avoidant,
they’d rather quit than go through the discomfort
of asking for a raise, for example.
For every action, there’s an equal opposite reaction.
There’s a finite mindedness to it,
which is how do I solve the immediate problem in front of me
without considering the long-term impact of that decision?
I’m not for or against the decisions.
I’m saying consider the long-term impacts.
And I’ve been public about this,
and I’ve been criticized for it by young people,
which is flash forward five or six years
and you’ve had seven jobs, right?
And whether you’re bouncing
because you think they’re all toxic
or whether you’re bouncing
because you’re just dialing for dollars, whatever it is.
In five or six years,
the new employer is looking at you
and you’re a certain age now,
which means I expect a certain level of maturity
and accomplishment.
– Yes.
– You haven’t had it
because you haven’t gone through the shit.
– Right.
– You keep jumping shit.
So I don’t even know that you’re qualified
for the senior position you’re applying for
that somebody else with seven years experience
could apply for, number one.
And number two, if I’m given two resumes,
one with somebody who’s bouncing around
and one who’s had two jobs over seven years,
I’ll take the one with two
because I’m not gonna trust
that this person’s gonna stick around
after I’ve trained them up and got them all in.
We have a few years
before we start seeing the repercussions,
but the repercussions are coming.
And again, I’m not saying don’t quit.
I’m saying just be cognizant
that there are implications
and maybe be a little slower.
– Do you think the problem there
is that they’re picking the wrong profession
and wrong job from the get-go
or they don’t have the grit to stick it out
during the hard times?
You mentioned this confrontation avoidant.
Is it because they are like,
this makes me uncomfortable.
I can’t handle it.
I’m out.
Or did I just pick wrong right away?
I know we’re generalizing, but–
– I mean, who knows?
But this idea of dream jobs is a funny thing, right?
– Yeah.
– Ain’t no such thing, number one.
Every job is imperfect,
like every relationship is imperfect.
And we live in a world that idealizes
both relationships and jobs.
And so when my relationship isn’t perfect
and my partner doesn’t do all the perfect things
and then I ban in that relationship
and I’m doing the same thing,
this job isn’t perfect and I have stress
and they want me to work late on a Thursday,
there’s a problem with pursuing the dream job
because it doesn’t exist.
Now, that’s not to say we should suffer either.
I believe you should have joy at work.
I believe you should be fulfilled by work.
I believe that you should be inspired
by the company you work for,
but you don’t have to like every day.
You can love your children,
you don’t have to like them every day.
You can love your job,
you don’t have to like it every day.
I think we confuse the two,
that there are days that I don’t like my job
and that’s the reason to quit.
But fundamentally, are you working in a place
where you feel seen, heard and understood?
Are you working in a place
that you feel like you’re growing as a human being,
that you actually are a better version of yourself
because you work here?
Are they pushing you and challenging you
to take on more responsibility
than maybe you even think you’re capable of?
And that’s uncomfortable.
And if you go back to Steve Jobs, for example,
and I know we herald him,
but he was pretty remarkable, right?
One of the things that Jobs did
is it was uncomfortable working at Apple.
And it wasn’t uncomfortable because he was mean,
although he wasn’t the nicest person in the world,
it’s because he saw potential in people
that they didn’t necessarily see in themselves.
And he pushed and pushed and pushed people.
And people who didn’t like being pushed, they quit.
But the people who were okay being pushed,
they all said I achieved more at this company
than I ever would have imagined.
Johnny Ive, this sort of middling designer,
Jobs sees something in him
that maybe he does or doesn’t even see in himself.
And he gets pushed and pushed and pushed and pushed.
He becomes one of the greatest designers
in modern history.
– I had a really long conversation with Tony Fidel
about this, working with Jobs.
And the growth comes from the discomfort.
– The growth comes from the discomfort.
I mean, look, there’s so many metaphors and analogies,
I love the one about the lobster.
– I haven’t heard the lobster one.
– So lobsters, the soft mass inside the shell
is what grows, that’s the origin.
The shell itself doesn’t grow.
It’s this hard thing that excretes out and hardens.
And as the lobster grows,
it starts to get very uncomfortable in its own shell
’cause it’s now bigger.
It’s like wearing clothes that are too small.
And only when it gets to that point,
does it then shed the shell and build a new one.
In other words, you can’t grow without being uncomfortable.
– Right, right.
Yeah, that’s so good.
– And that’s true.
I like to equate everything to personal relationships
because corporate relationships are relationships, right?
– Yeah.
– Which is every fight or uncomfortable situation
I ever had with my girlfriend.
Though I did not enjoy it,
though I wish we’d never had it.
Though sometimes I was to blame,
sometimes she was to blame,
more often than not, we were both to blame.
And when I say that just a quick aside,
usually in an argument,
we start accusing each other of who started it.
– Right.
– The reality is, yes,
absolutely somebody always started it
and the other person almost always poured gasoline.
– Yes.
– So you both have a culpability,
it doesn’t matter what started it,
you both made it worse.
– Right.
– Invariably, every uncomfortable conversation
or fight that we ever had,
though I hated every moment of it and so did she,
we ended up stronger and closer because of it.
– Yeah.
– Because there were lessons that were learned,
there were triggers that were realized,
there was language that was dissected.
And what we did was learn to fight,
not against each other, but against the problem.
– Mm-hmm.
– And I think it’s the same at work, right?
Which is when there’s pressure exerted,
is it me versus management?
Or is it management and me
versus whatever we’re trying to accomplish?
– Right.
– And good leaders know that
and good team members know that.
– Mm-hmm.
– It’s when it becomes adversarial,
us versus them.
– Yeah.
– And by the way, I blame leadership
as much as I blame employees.
Team members will go out for drinks and vent about work,
which I’m, by the way, totally healthy.
– Yeah.
– And I’m talking with that.
But sometimes narratives,
and especially in virtual and distributed workforces
where everybody’s wherever they are,
the rumor mills can spin out of control a lot quicker.
– Yes.
– And we blame management for what they did to us
or whatever.
But it happens at leadership as well.
The number of times I’ve sat in leadership groups,
including my own.
– Mm-hmm.
– Where we label someone dumb or lazy.
– Mm-hmm.
– Or inconsiderate or one foot out the door.
And we make jokes about,
ugh, here we go again.
We’re entitled or just go down the list.
And we label them.
We create a narrative about them.
And now we treat them that way.
– Mm-hmm.
– And though they may not know our narrative,
they know that they’re being treated a certain way.
– Mm-hmm.
– And so one of the things that is imperative
in any leadership team,
which is when one person finds themselves venting
about somebody where it’s creating a narrative
about another human being,
it’s imperative that somebody else on the leadership team
interrupt that narrative.
– Mm-hmm.
– And say, they could be lazy.
True, that’s definitely a possibility.
Or they’re overwhelmed.
– Right.
– Or we haven’t given them good instruction.
Or they’re struggling at home.
– Yeah, I was gonna say,
they’re going through something that we don’t know about.
There’s a list of things.
And so we treat them with empathy
and maybe check in on them.
I expect leadership to go first
’cause they should know better.
But whether it’s in a group of team members
about each other, more about management,
management about team members.
And again, I hold the leaders to a higher level
of accountability and if they act appropriately,
the team will act appropriately.
But we have to interrupt each other
with these kinds of narrative.
Discomfort is one of those things where
it’s good to be transparent about discomfort.
And it starts, again, leaders set the tone.
– Because it’s disarming.
– When you lie, hide and fake.
When you pretend that you got it all figured out.
People will think you got it all figured out.
And so they will pile on more and push you more
and give you more and expect more
because you said everything’s good.
And that’s when it becomes overwhelming
and that’s when you start blaming management
for mistreating you.
But hold on, right?
Whereas I’m a great believer
in just being totally transparent about discomfort.
And sometimes it’s real
and sometimes it’s perceived, for example.
And I had it happen recently.
One of my team members, she’s wonderful,
we’re a distributed workforce
so we don’t get a lot of face time, right?
So she’s never had a lot of one-on-one time with me.
You know, I see her corporate off-sites and stuff like that
and I see her on Zoom all the time.
But she’s never had one-on-one time with me.
And so we brought her out to LA
to have a one-day hackathon with me.
She’s young, she’s in her early mid-20s junior employee.
And she came clean.
She said, “I just need to tell you,
“I was really nervous about today.
“I don’t get us a lot of face time with you
“and I want to make sure I do right.”
And I got really prepared, but I’m really nervous.
And giving me that information was magical
because if she had come in all like ego and everything,
I would have ripped her writing apart
a lot more aggressively because she’s good.
But now I could just be like a little softer
or it’s a, “You’re doing great.
“I can just reinforce.”
‘Cause I know she’s feeling a little intimidated or fragile.
So saying, “I’m really excited about this project.
“I’m really excited about this new responsibility.
“If you’ve given me, I’m a little uncomfortable
“because I’ve never had this amount of responsibility.
“I really don’t want to screw it up
“and I want to do right by you
“and I do want to do right by me.”
And I don’t want to fail.
And simply just saying that means that a good leader
will be like, “Got it, I’m here, you’re good.”
And you feel supported in that discomfort.
– Yes, right?
– Uncomfortable isn’t the problem.
It’s feeling alone and uncomfortable.
It’s the problem.
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– A good leader can see the signs.
Virtual makes it much more difficult.
Yeah, working in a distributed workforce
makes it much easier to hide, lie and fake.
Body language doesn’t come across as easily.
Somebody’s a little bit fidgety, you can’t really see.
Doesn’t really show up on a Zoom call.
But I think discomfort is one of those things
that to learn to be uncomfortable
is probably the single greatest asset you could ever,
you know this, ’cause nobody’s ever achieved anything
in the world did it smoothly.
We all came close to zero if not hitting zero first,
all of us.
And Lionel Richie talks about this.
When he was younger, he had crippling,
debilitating stage fright.
Lionel Richie.
– Yeah.
– And he says there’s two types of people in this world.
Nobody has the absence of fear.
The two types of people in the world
are those who have fear and they take a step back
and there are those who have fear
and take the step forward.
And I always took the step forward.
– Yeah.
– Courage isn’t the absence of fear.
It’s being afraid and leaning into it.
And so to be uncomfortable and step forward
is perhaps the single greatest thing you can ever learn.
And what you discover is you’re surrounded
by people who wanna help you.
– Yes.
– 100%.
– Which is the most amazing thing to discover.
– This is one of my biggest mistakes.
You know, when I was in my early 20s
and I had my first startup,
I was pleasantly surprised in that it was my first go,
it was dig and it was the first social news app
and it exploded to tens of millions of users in six months.
– Yeah.
– And I was afraid. – That’s uncomfortable.
– Oh my God.
Well, here I am, college dropout, moved to the valley.
I was so intimidated by everyone around me,
the VCs I was getting introduced to, everyone else.
And I was scared to raise my hand
and say, “I don’t know the answer to this.”
Because everyone was looking to me as like someone
that had created something new and exciting.
And it wasn’t until actually two years into the company
where it was really strange.
It was a very small period of time
where dig was bigger, traffic-wise than Facebook.
And so Mark came to my office, Zuckerberg.
And he just asked a thousand questions.
And he was really probing me on so many different things
and admitting so many things that he just didn’t know.
And I was like, “Wow, I need to be more like this.”
– Exactly.
– Because here I am operating in this silo,
afraid, ashamed, and it’s not doing me any good.
I’m actually doing more harm to my business.
And once you have that unlock
and you realize it’s a massive strength
to have vulnerability and to raise your hand
and say, “I don’t know the answer to this.”
It’s a huge, huge unlock.
– I don’t know is the three most important words
any young entrepreneur can ever wear.
It’s your story, it’s also my story.
I had a small business and I was chief cook and bottle washer.
And I started having employees
and I had to be in every meeting
and I had to make every decision.
I thought I had to have every answer.
And if I didn’t, I thought I had to pretend that I did.
And A, the business doesn’t do well with that model.
But B, it’s crippling, like depression set in.
– Oh, 100%.
– Because you feel so alone in the hiding.
And it wasn’t until I learned to say,
“I don’t know or can you help me?”
Or learn to accept help when it’s offered.
The amount of help we’re offered on a daily basis
if you just counted it’s tons to say, “I’ll take that.”
And it is humiliating by the way.
Like I have some very successful friends
and they asked me what I’m going through
and I’ll talk about the stuff that I’m stuck with
or don’t know.
And these are very successful people
that I want to look good in front of.
The amazing thing is by being open to them,
the amount that they are there for me,
like that day of humiliation
was the greatest investment I ever made.
And I think that’s what you need to think of it is.
Like it’s an investment which is,
when you make an investment, you pay money, it hurts.
You take it out of your bank account,
it was a high number and it was a low number.
And you’re like, “Oh, this works.”
It’s an investment.
And sometimes it pays off.
I can’t say that it pays off all the time.
Sometimes it’s just humiliated.
– Yeah, right.
But that’s okay.
– And that’s okay.
– What was your personal story?
What was that moment you mentioned
where you didn’t want to go to work anymore?
And then how did you dig yourself out of that?
– Not ironically, I didn’t do it alone.
I reached a point where
I didn’t have the skillset to build the business.
I’d reached a certain level of growth
that I could achieve by myself
and needing to let go and not be in every meeting
and not make every decision.
That’s a critical point
because you literally can’t grow beyond a certain point
of if only one person can make all the major decisions.
I couldn’t let go.
And so I couldn’t grow, which means frustration.
Did not build systems, did not ask for help.
Ego was out of check.
And I don’t mean like, I thought I was everything.
I mean, I was pretending that I was everything.
And depression set in.
Didn’t want to wake up.
Didn’t find the joy in business ownership anymore.
And was really good at lying, hiding, faking.
I could pretend that I was happier, more in control
and more successful than I felt.
And by the way, so good that nobody could tell.
I mean, I was phenomenal.
And one friend could see through the armor.
One friend came to me and said something’s not right.
I don’t know what it is, but something feels off.
And for whatever reason,
probably ’cause she is really good at making a safe space.
I started to open up.
And she didn’t try and fix anything.
She didn’t have suggestions.
She simply let me be vulnerable.
And it’s not the act of being vulnerable per se.
It’s the act of not feeling alone in that vulnerability.
And that she could hold space for me so effectively.
I now had the courage to take all that energy
that I was using to lie, hide, and fake.
And I could take that energy to find a solution
to my malaise.
And the solution that I found was sitting right in front
of me the whole time, which is this thing
that I called the golden circle.
And that’s when I made the realization
that I knew what I did.
I knew how I did it, but I didn’t know why.
And that was the reason that I was stuck.
‘Cause I had no sense of purpose, cause, or belief.
And I became obsessed with understanding my why.
I learned my why, but more important,
I learned how to help others find theirs.
And I helped my friends find their ways.
Just because I wanted, it’s like you see a great movie.
You tell your friends to go see it.
No other reason, right?
There’s excitement.
And my friends, they quit their jobs
and started their own businesses,
or they found renewed joy in the jobs that they had.
To the same levels that I was experiencing, way higher.
And they asked me to talk to their friends.
And I would go to someone’s apartment in New York City
and stand in the living room
and talk about this thing called the why
and help people find their why for $100 on the side.
And my career took a weird turn completely by accident.
It was all organic.
But the point to the question was,
it was one person who held space.
We forget that we are social animals
and our very ability to survive
requires the help of other people.
If you fall asleep, you need someone
to watch for wild animals.
We just know good by ourselves.
We can’t solve complex problems by ourselves.
But in groups who are remarkable,
human beings hunted woolly mammoths.
– Yeah.
– No other animal could take down a woolly mammoth.
But we frail, weak human beings could.
Because the asset that we have that is our superpower
is our ability to cooperate.
And if you know that and you remember that,
that no human being can survive or thrive alone,
that we are fundamentally social animals,
you have to learn to ask for help
and you have to learn to offer it.
And that’s what I did.
That’s where I learned that lesson.
– One of the things that you said that struck me
is, and this is the mistake I make with my wife a lot,
I’ll admit it publicly,
is that I go into problem solving mode.
She’s got an issue and rather than just sit there
and hold space and have some empathy
for what she’s going through
and how something lands on her.
I’m like, let’s fix this.
And I’m like throwing out solutions and all this.
And then that’s not always the best.
– Men are particularly bad at it.
Men are usually in solution, not exclusively,
but tends to skew that way.
– That’s correct.
That is not a good idea.
And there’s a great video on YouTube
called It’s Not About the Nail.
Everybody can go look it up.
It’s one that has a bazillion views.
It’s many years old,
but it basically sums it up absolutely perfectly.
And by the way, you’re the same.
When you have a problem and somebody says,
well, why don’t you do this?
You end up being defensive and fighting with them
because you don’t actually want them to solve the problem.
You just want to feel safe in your stuckness.
And when somebody comes to you and says,
I’m struggling, just go tell me more.
What else?
By the way, you know how to do this
because you read all the books to do it with your children.
And when they say, daddy, I’m afraid.
That’s okay, you can be afraid.
But daddy this and you’re like, that’s okay.
You don’t try and fix their fear.
You hold space for their fear.
When they’re nervous,
you don’t try and fix their nervousness.
You don’t have to be nervous.
Don’t be nervous.
We’ve learned that that’s a terrible thing to do
with children.
You go, oh, I know it’s scary.
You affirm the feelings.
Well, why did you stop doing that
just because somebody is an adult?
Like you still have to affirm their feelings.
– It’s a great point.
– Honey, I’m nervous.
Honey, I’m scared.
Honey, I’m confused.
Honey, I’m angry.
– Yeah.
My girlfriend and I were,
she said something about something
and I had done something that upset her.
And I basically was like, well, that’s ridiculous.
And clearly I didn’t mean to.
How can you say that I did that?
Of course I didn’t do that on purpose.
– Right.
– You know, I’m full on defense mode.
I’m in full on like, it’s not really gaslighting,
but it’s a form of gaslighting,
which is like, I’m saying,
you can’t feel that way about that, right?
And after many rounds, I finally said,
if I were in your shoes, I would have felt the same.
And she said, thank you.
And the funny thing is what preceded that was,
I just need you to see it.
What if you were me?
Like she literally gave me the instruction.
– Right.
– I’m like, well, if I were in your shoes,
yeah, I probably would have felt the same
where you’re feeling now.
– Right.
– That was it.
– No, you’re right.
– Argument over.
– I’ve been there.
I’ve been in this exact conversation.
– Argument over.
– Yeah, 100%.
I’ve had it happen where I’m in a bad place
and I call a friend and told him basically like,
hey, I’m not feeling good.
And they start fixing and I get off the phone.
– Yeah.
– ‘Cause they make it worse.
– So true.
– I talk about this a lot, which is the idea
of sitting in mud, which is when we or our people
we love are in a bad place, they’re sitting in mud.
And our instincts, well intention,
is to pull them out of the mud, right?
To fix it.
Well, oh my God, that looks horrible.
Nobody wants to be in mud.
Let me pull you out of the mud.
And they don’t want to be pulled out of the mud.
– Right.
– But they don’t want you standing on the sidelines.
What they want, what loving friendship,
what loving relationship means is,
I’m gonna come and sit in the mud with you.
– Yeah.
– I don’t want to sit in the mud with you.
It’s no fun being in the mud with you,
but I’m gonna get in the mud with you.
– Well, that act alone will allow them to dig themselves
or climb their way out of the mud.
– Or, turn to you and say,
I think I’m ready to get out of the mud.
– Yeah.
– And then you can go into solution mode.
If a friend is depressed,
they just don’t want to get out of bed.
And we can’t make them get out of bed
and tell them they have to get out of bed.
Go to their house and get into bed with them.
And watch TV, watch movies all day, be depressed with them.
It’s not fun, it’s not productive,
but it makes them feel not alone.
– Right.
You’re matching their spirit at the moment.
– You’re making them feel not alone.
– Yeah.
– And usually when we try and fix someone’s problem,
usually when we try and pull them out of the mud,
what that makes them feel
is that they’re in the mud by themselves.
‘Cause we’re standing on high ground, on dry ground,
saying, let me pull you out.
– Right.
– Oh my God, look at you down there in the mud.
Let me pull you up here to the dry land,
which all that does is remind them that they’re alone.
– Right.
You must have just given everything
that you’ve been through in all your talks.
I’d imagine people come up to you randomly
or at talks, after talking to the line forms
and people wanna ask you questions.
If a young person comes to you looking to be pulled out
or in some way, it’s like, give me advice on this or that.
How do you empower them to make their own decisions?
How do you equip them to figure out their why?
‘Cause I’d imagine you can’t do that in two minutes.
– You can.
– Tell me.
– So finding the why is the easy part.
It’s like college graduation is called commencement.
– Yeah. – Beginning of something.
– Yeah.
– Well, finding your why is easy.
That’s why I called the book Start With Why.
‘Cause once you have it, now the work begins.
– Right.
– So again, there’s two questions there.
One is how to find the why and which I’ll tell you.
And the one is when you’re coming up to a stranger.
I mean, they don’t know me and I don’t know them.
– Mm-hmm.
– And they come up to me and say,
can you help me get out of this or, you know, hey.
– Right.
– And my answer is always the same as,
you don’t know me.
You know the image of me.
You know the image you’ve built of me.
I could be the worst qualified person to help you with this.
Go ask somebody who actually cares about you.
You know, you’re not my friend.
Like I like you, you’re seem very nice,
but why would I get into mud with a stranger?
– Right. – I don’t know you.
You know, go ask somebody who loves you.
Because it’s safer to be vulnerable with me
because I’m a stranger.
– Right.
– It’s hard to be vulnerable with somebody
who actually knows us.
– Mm-hmm.
– But that’s the thing you gotta do.
– Yes. – They’re asking the wrong person.
I’m sympathetic, but I’m the wrong person.
– Yeah.
– So where does a therapist fall on that?
Because you don’t know them,
but yet you can be vulnerable around them.
How do they fit into your thinking?
Like obviously it’s a useful tool to have a therapist.
– Therapists have said that I professionally
hold space for you.
That is my job.
– Right.
– Depending on the therapist, some of them have tools
to help you with whatever you’re dealing with, right?
So they can equip you with tools.
And I think therapists are one of the things that we need.
I don’t think they’re the only thing that we need.
I believe in therapy, I think it’s a good thing.
And the practice of being open with someone.
But I hope that you use that skill set with your friends.
Like what’s the point of learning the skill
if you’re not gonna apply it in other places?
– Right.
– And I think somebody who really struggles
with vulnerability should do therapy
because it is a good way to practice being vulnerable
with the people you really need to be vulnerable.
If you’re only vulnerable with your therapist and no one else,
I think that’s as much of a problem
as not being vulnerable to anybody.
It’s an education as much as it is a catharsis.
– Right.
– So going back to your question about finding your one.
– Yes. – Okay.
I’ll give you two answers.
– Okay.
– There are many ways to do it.
We’ve tried to make many tools available.
We have things in our website
that people can do to find their why.
I wrote a book called “Find Your One.”
– Yeah.
Your website’s got some great thank courses
and things that people can sign up for, which look awesome.
– Thank you.
– But there’s something called the friends exercise
which anybody can do and it’s fun.
Basically find a friend who loves you and you love them.
The kind of friend who,
if you call them at three o’clock in the morning,
you know that they would be there for you
and you would be there for them.
– Okay.
– Do not do this exercise with a spouse,
with a sibling, with a parent.
It does not work.
Those relationships are too close.
– Okay.
– Do it with a best friend and ask them the simple question.
Why are we friends?
And they’re gonna look at you like you’re crazy.
Because the part of the brain that controls
all of our feelings, love, loyalty, trust,
the limbic brain doesn’t control language.
It doesn’t control rational thought.
And so it’s very hard for us to
rationally articulate emotions,
which is why we use metaphors.
– Yeah, we’re hard-tempering in the words.
– Yeah, of course.
It’s a biological problem.
And so then you immediately convert the question,
because why is an emotional question?
And you start saying, “Come on, come on.”
What specifically is it about me
that I know that you would be there for me no matter what?
And again, they’re gonna hem and ha,
it’s very hard to put into words.
– What if they just give you high level like,
“Oh, you’re funny.” – They will.
They will.
That’s what they will do.
They’ll start describing you.
You’re funny, I trust you, you’re always there for me,
and you have to play devil’s advocate.
Great, that’s the definition of friend.
What specifically is it about me?
Or great, yes, all true,
but you get that from lots of other people.
What specifically is it about me?
Then I know you’d be there for me no matter what.
And they’re gonna go through a few rounds of this
where they’re just describing you
and describing this generic best friend archetype.
And eventually, because of discomfort, they will give up.
And they’ll go, “Look, man, I don’t know.
“All I know is,” and they’ll start describing themselves.
And this is what my friend said to me
when I did the exercise.
“Look, Simon, I don’t know.
“All I know is, I can sit in a room with you.
“I don’t even have to talk to you when I feel inspired.
“And I got goosebumps.”
So what they’ll do is they’ll say something about themselves
and you will have an emotional reaction.
You’ll get goosebumps, you’ll well up with tears,
because what they’re doing is articulating the value
having their life, which is the thing you give to the world,
which is your why.
And if you do this with multiple friends,
you will get very similar, if not the exact same answer,
because who you are in the world
is the space you fill in all of these people’s lives.
– And so is this idea what you give to them
or what you give to the world,
are you looking for a cross-section of agreement
amongst friends?
– No, no, no, no, no, no, no, no, no.
This is not subjective.
This is objective.
– Okay.
– Find as there’s common themes.
And your why is the value you have in the world.
It’s why not everybody likes you.
It’s not everybody wants what you have.
There are plenty of people who think
that my entire existence is cheesy.
I mean, I talk about inspiration.
I mean, literally what could be cheesier, right?
And are very dismissive.
Well, I’m not for them.
That’s okay.
It’s like some people like chocolate,
some people like vanilla.
It’s like, it’s all good.
But the people who love what I have to offer,
well, those people are either part of the movement.
They either, you know, buy, read a book
or watch a video or they’re my friends.
And we’re all kind of the same kind of person.
It’s like when Apple says think different,
who are they describing?
The answer is yes.
They’re describing their employees.
They’re describing their founders.
They’re describing their customers.
They’re describing the answers.
Yes.
They’re describing everyone who believes in that thing.
Well, it’s the same.
Your why is the thing you give to the world
and the people who value that
are the ones who want to receive it.
But it’s always gonna be you.
– Can we have different whys, multiple whys?
When do these whys form?
– Your why is fully formed by your mid to late teens.
The youngest why Discovery ever did was a 16 year old
and it worked perfectly.
We are all the products of our upbringing.
You are who you are based on the experiences you had
when you were young,
which made you quote unquote who you are.
And you don’t have a why for work and a why for home
because then how would I know which one’s the real you?
And one of those two places you’re lying, right?
And you can’t change your why every year
because then again,
how would you ever form trusting relationships
because I’d never know who you are.
Are you authentic this week?
But last week was a different why.
So it’s the concept of authenticity
literally couldn’t exist if your why could change.
You are who you are and the rest of your life
is simply an opportunity to live in balance
with that why or not.
I’ll show you another way to find your why,
which is pattern recognition.
I want you to tell me something you’ve done in your career
whether it was commercially successful or not
does not matter.
But something, a project you’ve worked on,
something specific that you did in your career
that you absolutely loved being a part of.
And if everything you ever did for the rest of your life
was like this one thing,
you’d be the happiest person in the life.
– I would say one of the things that I’ve enjoyed is-
– Loved.
– Loved, okay.
One of the things that I’ve loved is then
this is probably ego loaded.
So let’s just take it with that.
So I’ve loved getting the recognition from others
for discovering things earlier than anyone else.
– Tell me something specific that you did
that you loved the process, you loved being a part of it.
That if all of your projects were like this one,
’cause you’ve started multiple business,
many of them have had commercial success.
Some of them you enjoyed more than others.
And within those projects, there were things that happened.
– Sure.
– Things that went right or wrong,
new clients you landed, whatever it was.
Tell me one specific thing throughout this entire career
that you loved, you didn’t necessarily like it every day,
but you loved every, like this is the most exciting thing.
– I would say that is the invention of things that-
– Specific, invention of what?
– When we created social voting for the first time
and you could see the number go up
on a piece of content on the web,
this was before likes.
And because of something called asynchronous JavaScript,
you could actually watch as people socially voted
on things in real time and inventing that
and seeing that come to life and watching humans
in real time gather around articles
and watch them socially spread information.
That moment of creating that and seeing it take off
was just the creation process was a highlight
you would probably never get anywhere else.
That was a great just accomplishment for me and my team.
So of all the amazing things you’ve done
and you’ve had exits and all of the things
that people dream of, right?
What specifically was it about that,
about social voting that stands out in an entire career?
I think it’s because historically my kids
will look back on that and said,
dad did something that changed the world in some small way.
– Could say that about other things you’ve done.
Dad did something with dig,
dad did something with all those things.
My dad did was precursor to this or precursor to that.
Mark Zuckerberg came to my dad for advice.
So that, what specifically was about social voting
that was so exciting.
– Probably because it had the biggest impact.
I would say there’s been other things
like when I made the first intermittent fasting app,
severely obese people, my dad died of a heart attack.
We’re losing a lot of weight
and we started getting emails saying
it changed their lives.
And that was another aha moment where I was like,
this makes me feel so good.
Just because I know that I’d give anything
for another year with my dad
and to like think that I’m giving somebody else’s son
or daughter an extra year with their mom or dad
is a huge one for me.
So I think that’s another huge one.
– No, that’s good.
Tell me an early specific happy childhood memory,
something I can relive with you.
– Saturday mornings, my dad–
– One memory.
– One memory, catching a fish with my dad out on a boat.
– So this is a specific time you were at?
– Yeah, 100%.
– Okay, tell me about that day.
– Got up early.
I had never been fishing in the sea,
only kind of on lakes.
And my dad drove me about,
it was a multi-day trip to get up to the state of Washington.
We went out on a boat.
I was probably 10 years old
and I helped reel in like a 45 pound salmon.
I obviously couldn’t do it myself ’cause it’s tiny.
– Actually, I take that back.
The better memory was laying in the back of our truck bed,
looking up at my dad show me satellites for the first time.
And I saw a satellite camping with my dad.
That was like just a magical moment.
– Okay, tell me more about that.
– I just realized how much I loved my father.
And I just realized how special it was
that I got to spend some one-on-one time with him
and that he would take time out of his busy schedule
to show me attention, to teach me things.
It was difficult because my dad was a very verbally abusive
father to my mom.
And so he was always angry.
And so to see him being tender with me
was just a beautiful thing
because I got to see my dad in a place of like happiness,
which I didn’t see that often.
– And what was it about showing you the satellites?
– More one-on-one time.
And I just didn’t even know those things existed.
My late 40s satellites were a big deal way back in the day.
And now I will go watch SpaceX launches
outside of my balcony.
But back then it was like,
I just didn’t even know you could see him with a naked eye.
And if you’re laying on a clear enough night,
you can look up and you can actually track them
and see a satellite, which is amazing.
– Yeah, okay.
So what’s interesting about those stories,
seeing satellites with your dad
and when you talk about the intermittent fasting,
you use very similar language in both of them,
which is you talk about the opportunity
to have these moments, right?
My dad was an angry man
and I got to see him in tender times.
You talk about giving somebody else
the opportunity to spend more time with, right?
It’s about the discovery of beautiful things
that you didn’t know existed.
An angry man who could be tender.
A satellite you didn’t know you could see with a naked eye.
The discovery of changing and intermittent fast.
Even the uploading of things.
It’s really about, it’s recognizing that there’s community,
like there’s other people who connect.
And I think your why sort of exists in this arena.
I’m struggling to find the exact words for it.
– Yes, that feels right to me.
It’s very right to me.
Where the things that bring you joy
are when you give somebody the opportunity
to make a discovery that has a positive impact
in their lives to see something they didn’t see before.
And in all of those examples,
there was an element of like, I didn’t know that before.
I had never seen that before.
I didn’t know that could have an impact.
And there was a positive impact
whether it’s spending time with your dad.
And you said it beautifully,
which is giving somebody opportunity to spend more time
with their mother, father that you didn’t have.
And to some degree,
you’re becoming the best parts of your father,
which is to take quiet moments,
show somebody something
and let them discover something magical.
– Yeah.
I think that’s why I like playing with my kids so much.
– The things you get to show your kids.
– Yeah, and see through their eyes.
– See through their eyes.
– Yeah, it’s beautiful.
– It’s beautiful.
And even in the way you talk about social voting,
which is to see through other people’s eyes
what they find interesting.
So there’s discovery for the person
who’s learning it for the first time,
but there’s discovery for you who’s teaching them
because you don’t know where it’s gonna go.
– Right.
– And so there’s discovery on both sides.
– Yeah.
– So I think discover or discovery
is sort of your magic place, your magical place.
Anyway, your Y exists somewhere in the–
– No, that’s awesome.
I do wanna talk about what you do professionally for people
because I think this is important.
I noticed your site has some ways that people can sign up
and actually learn how to be coached through this.
More people need to do that.
And I wanna take it further now.
What do people do on your site?
– So we started the optimism company
with a very specific purpose,
which is to advance the idea of human skills.
I hate the term soft skills, hard skills and soft skills.
First of all, hard and softer opposites.
These things do not work against each other.
And also there’s nothing soft about soft skills.
There are hard skills and there’s human skills.
Hard skills are the skills you need to learn
to do the job you need to do.
And human skills, the skills you need to learn
to be a better human being.
And there’s a great irony in being human, right?
Like cats don’t have to work very hard to be cats.
They’re just naturally good at being cats.
But we have to actually do a lot of work
to be good human beings.
It’s frustrating and annoying.
And we built the optimism company
to completely focus on teaching people
the human skills they need to be better human beings.
And to advance that ability to cooperate and socialize.
– Is that both personally and professionally?
– It’s you, right?
So when I teach you better listening skills,
when I teach you how to have a difficult conversation,
when I teach you how to have an effective confrontation.
Now we teach it in a work context
because that’s where the people are.
But the reality is those skills are useful everywhere.
I like to make the joke that in the,
there’s an entire section of the bookshop called self-help.
And there’s no section of the bookshop called help others.
And what we need is to advance the help others industry.
And that starts with teaching people the human skills
of how to not only be a better version of yourself,
but more important, which is how to be a good partner,
friend, colleague, coworker, boyfriend, girlfriend,
brother, sister, son, daughter,
mother, father to somebody else.
Because all of these relationships, boss, employee,
dad, mom, brother, sister, they’re all cooperative.
None of them are solo.
They all involve a relationship.
Almost every label we have for people
involves some sort of relationship.
You can’t be a leader if nobody’s following you.
You can’t be a follower if there’s nothing to follow.
All of these things is a relationship.
Even when people talk about their faith,
I’m a follower of X.
Well, that’s a relationship.
That’s how they describe faith.
And so that’s what the optimism is singularly focused on,
which is how we teach people the human skills
to be better human beings.
That’s awesome.
I was picking to the website and I noticed
there was a couple of things you mentioned on the site
that you teach people the courage to lead
and then also conflict resolution.
How do you teach someone to resolve conflict?
So many of these skills, the foundational skill
of a lot of them is listening, right?
Like we talked about it before with you and your wife,
you fix everything.
One of what you need to do is learn to listen.
You work really hard to learn to listen to your kids,
but then you abandon the skill at work
or in your adult relationships, right?
And so conflict resolution, we have conflict at work.
We have disagreements, we have misunderstandings.
We feel triggered by certain things that people say,
whether they said it on purpose or by accident.
We feel pressure, we react badly.
There’s conflict everywhere.
And I don’t believe that world peace, for example,
is the absence of conflict.
I think that’s nonsense, right?
We live in a world with no conflict or war.
No, not gonna happen, right?
To me, world peace is the ability
to resolve conflict peacefully.
There’s gonna be conflict,
but how do you resolve it peacefully?
And you see it at work all the time.
People yell at each other, people quit out of anger,
people fire out of anger.
Conflict is gonna happen.
How do we resolve our conflicts peacefully?
You’re gonna have conflict in your relationships.
How do you resolve conflict peacefully?
So for me, conflict resolution is that very difficult skill
of when you’re angry,
you still have the skill to hold space for somebody else.
That’s so hard because when someone is triggered,
everything goes out the window.
And it’s just like, all of a sudden it’s all about emotion.
How do you train yourself to say,
let me pause this emotion and set aside for a second
and listen, what’s the process like?
Part of it is you have to have a game plan
going into every conflict.
You wanna make these decisions before you get to conflict.
You don’t wanna be in conflict
and then having to come up with strategy.
You need to master these skills before the conflict
so you’re prepared.
Whether they’re athletes or military,
they talk about muscle memory.
Then you practice and practice and practice
and practice and practice.
You don’t quote unquote, have to think in the stressful time
because you can just quote unquote, rely on your training.
– Interesting.
– Very similar.
– So you offer that type of training?
– Well, I mean, if you do these kinds of trainings,
then you’re doing them in artificial environments.
– Is it role-playing?
What type of training is it?
– The role-playing, we expect people to go do themselves.
But the point is all of these things,
even if you learn the skill, you have to go practice it.
So I’ll give you one example.
My girlfriend, we talk to each other very openly
when we’re not in conflict,
that when we fight, we don’t want it to be me versus you,
we want it to be us versus the problem.
So we know that.
So both of us have that mindset.
So when conflict does arise, we both have the right mindset.
And sometimes it takes us a little to get back to it.
Or we can say to each other, hey, hey, hey,
I’m not trying to be right here.
I’m trying to solve this problem.
And then we’re the minds of the person.
But I’ll give you a real-life example
that actually happened where we went down
that horrible rabbit hole of who started it.
If you hadn’t done this, then I wouldn’t have done that.
Well, if you hadn’t done that,
then I wouldn’t have done this.
I mean, it sounds like some Middle East conflict,
which is like we’re both blaming each other
for what had started.
And it was getting worse and worse and worse
and more aggressive.
And it occurred to me in that fight,
this is going nowhere.
This is intractable.
– This is gonna end up on–
– This is just not–
– You on the couch or something.
– This is one of us is gonna storm out.
If you just flash forward 10 minutes,
there’s no peaceful resolution to this journey we’re on.
Where we’re pointing out what I did right
and what she did wrong.
And she’s pointing out what I did wrong
and what she did right, right?
And I literally interrupted.
I said, okay, this is going nowhere, new rules.
We’re gonna reverse the script here
because right now I’m pointing out everything
I’m doing right and you’re doing wrong
and you’re doing the same, new rules.
From now on, I’m gonna tell you what I did wrong
and what you did right and I’ll go first.
– Wow.
– And I said, here’s what I did wrong
and here’s what you got right.
And she goes, well, yeah, here’s what I got wrong
and here’s what you got right.
– That’s beautiful.
– And I said, well, here’s what I got wrong
and you got right.
– And in five minutes or less,
the tension had been released.
We realized that both of us were trying.
Neither of us was evil.
Both of us were doing things right
and both of us had accountability.
– Yeah.
– And in that moment, it just petered out.
– That’s beautiful.
– You’re taking the knob and just turning it down enough
to where you can have a sensible conversation again.
– But I created rules.
– Yes.
The rules of engagement are this.
We’re gonna continue to fight
but we are operating from this script.
Me right, you wrong.
I’m just gonna flip the script.
Me wrong, you right.
– Yeah.
– And let’s just see what happens.
– Do you use that every time?
Or is that just–
– No, I didn’t.
That was spontaneous in the moment.
– That’s amazing.
– I’ve never done that before.
But I’m gonna do it again.
– Yeah.
– But the point is, is like doing it once even,
the next time you go down that path,
I don’t have to go down the path and get it really tense
’cause I can stop it immediately like, look,
I hear what you’re saying
and I definitely have some culpability here.
– Yeah.
– I definitely did this wrong and you did this right.
I can do it immediately now.
But the point is, these are skills.
– Right.
– Learnable, practicable skills and they’re muscles.
If you don’t use them, they’re gonna atrophy.
And this is what we’re trying to teach.
We’re trying to teach a host of these skills
that by themselves, they’ll help a little bit.
But the more of these skills we master,
the better colleagues,
– Yeah.
– Boyfriends, girlfriends, brothers, sisters, fathers,
mothers, sons, daughters, leaders, employees,
the better we become team members, colleagues,
any kind of human relationship.
– It was a big blind spot for me for a long time,
which is, I was a computer geek as a kid.
So back in our day, it was not cool to be a computer geek.
So I always made fun of a lot.
– Sure.
– So I was socially awkward and I had a really hard time
getting into my teens and then 20s,
going into a new situation without applying alcohol,
because alcohol for me was like a crutch, right?
I’ve since course corrected that,
but I’ve had to realize that when I stopped alcohol,
I have to build new muscles again.
I have to build new muscles around social interactions.
One on one, I’m fine.
I can turn it on for a while and I’m fine,
but there’s things that you have to kind of
figure out how to build that muscle around
so you can become proficient in it.
When you meet someone that is like,
I’m socially awkward.
I am not advancing my career,
the classic one is afraid to ask for a raise,
but let’s just say I’m not outgoing enough
to inspire confidence by the leaders of my organization.
Is that something that you believe
that we can learn and improve upon?
– So social awkwardness is not the problem.
I’m discomfort asking for difficult things
is not the problem.
I’m socially awkward.
You see me in a crowd, I’m useless.
I’m the one standing in the corner.
– So am I.
– I’m an over-sharer, mainly out of discomfort.
You know, talk too much, come on too strong.
It’s all discomfort.
Years of failed dates, you know?
– Yeah.
– Just social awkwardness.
And what I’ve learned is that those are not the problems.
The problem is confidence.
And I use social awkwardness or ADHD or introversion
or any of these excuses for whatever weirdness that I feel.
Right?
And I’m a great believer that none of these things
are right or wrong, they just are, you know?
You can be socially awkward as an extrovert,
you can be socially awkward as an introvert, right?
They just are.
And again, it goes back to asking for help
and just owning it, right?
Let’s be vulnerable, let’s be open
about our social awkwardness.
Let’s put it out there, let’s let people know.
I say it all the time, like I’m really socially awkward.
I say it on dates.
It’s a release, right?
It’s like putting it on the table.
So if I have a moment,
I’m not beating myself up in my head, right?
– Which can compound, right?
– And now it’s all me, it’s all me in my narrative, right?
– Yeah.
– And so the most important thing
is just owning it with confidence.
So here’s an example.
I’m really uncomfortable asking for a raise.
This is really hard for me, right?
That’s not owning it.
How about, hey, I’m so uncomfortable
having this conversation with you right now,
like I know I need to ask for a raise,
but I don’t wanna ask for a raise
’cause it makes me really uncomfortable,
but can we have the conversation anyway, please?
Right?
Yeah.
Or when you’re out with somebody,
meeting somebody for the first time,
like I’m really socially awkward and I’m an introvert
and I’m probably gonna say something
that’s gonna make you uncomfortable.
Like that’s just got creeper vibes only.
– Yes.
– Right?
– Yeah, that’s like I’ll follow you
out of the bar in a situation.
– Yeah, that’s so uncomfortable to even hear,
even though it’s well-intentioned
in its explanation, versus just so you know,
I’m probably like totally socially awkward.
I’m probably gonna say something
that’s gonna make you uncomfortable,
make me uncomfortable.
It’s gonna happen ’cause I’m just socially awkward that way.
You can hear the difference in tone.
– Right.
– When you just own it.
– Yes.
– When you’re just confident about who you are.
– It’s a great point.
– And so all the things that we talk about,
we’re trying to fix the symptoms,
but the cause is that you’re just not owning who you are.
– Right.
– And you can own your strengths
and you can own your awkwardness.
– Yeah.
– Just as an aside, I don’t believe
in strengths and weaknesses.
I believe we have characteristics and attributes.
And in the right contexts, those things are strengths.
And in the wrong contexts, those things are weaknesses.
So nothing that we have in our personalities
is inherently a strength or a weakness.
It’s all contextual, right?
So I work hard to be aware of my characteristics
and attributes, and I work hard to learn
when those things are to my advantage
and when those things are to my disadvantage.
And I work hard to put myself in situations
where who I am is more likely to be an advantage
than a disadvantage, right?
So for example, I’m disorganized,
chronically disorganized, right?
And I remember I was a young entrepreneur
at a networking event, socially awkward, introvert,
not very good at the stuff.
And I met a guy who, he’s like,
this time what you have to say is amazing.
I want to work with you.
Here’s my card, right?
Amazing.
And if I was organized, I would be texting him
from the taxi on the way home
or at least emailing him the next day.
Pleasure to meet you.
All of that stuff.
Well, I lost the business card.
Yeah, I don’t know what I did with it, right?
I had it and I lost it.
Two weeks later, I found it at the bottom of a briefcase.
And so I emailed him.
I don’t know if you remember when we met a couple weeks ago.
I just wanted to reach back out.
And he wanted to work with me more
’cause he thought I was busy.
That’s amazing.
So is being disorganized a strength or weakness?
The answer is it depends, right?
In some contexts, it is really not helpful.
In some contexts, it’s an accidental strength,
introverted and a little bit quiet, right?
And intimidated by, like you don’t know
what to say in a room, strength or weakness.
Well, at a networking event, it’s not gonna help you, right?
When you have to go around the room
and do all that kind of stuff.
But if you’re in a meeting and you’re the quiet one,
nobody knows if you’re an idiot or a genius.
And you’re the listener.
And they’re just waiting.
So a huge strength.
And so all of the things that I know about me
and when I thrive and when I fail,
when I’m happy and when I’m struggling,
I figure out what the characteristics and attributes are
and work very hard to put myself in situations,
find jobs, find clients, find opportunities
that are more likely to result in me
having those characteristics and attributes
work to my advantage
versus simply chasing the money,
chasing the client, chasing the opportunity,
finding myself in a situation
where this is not gonna work to my advantage.
– And do you believe those characteristics
and attributes can be enhanced?
Some people I know, they just can’t make a decision
for the life of them.
They can’t move forward.
Is that something where you look and say,
well, that’s kind of your DNA.
That’s an attribute or a characteristic.
That’s who you are.
Or we can actually take who you are
and enhance something
to make that a better, more smoother process for you.
– Yeah, I don’t think that’s necessarily
characteristic or attribute.
– Okay.
– What’s underlying that is risk tolerance, accountability.
– Yeah, so how do we improve risk tolerance?
– So risk tolerance and accountability
come from the relationships, believe it or not, right?
So this is why people say, the lawyers say we can’t do that.
– Right.
– The lawyers don’t make the decision on this.
– Right, right.
– The lawyers said I can’t do it.
That’s not a lawyer’s job.
And any lawyer who says you can’t do this
is actually not doing the job.
Lawyers have one job, advise you on risk.
There’s a lot of risk if you do that.
And you’re the one who’s supposed to assess the risk reward
and decide if the risk is worth it.
– Yeah.
– And if it’s not worth it, then say no.
But if you think it is worth it, then say yes.
– Every time I hear a CEO say that, it’s such bullshit.
– And when anybody says, the lawyer said we can’t,
they’re abdicating the responsibility
of making a decision.
– Yeah.
– It’s a weak leader, right?
Yes, take counsel from your attorneys.
– Right.
– Absolutely.
But ultimately, you’ve got to take a risk or not.
– Right.
– It’s your choice.
– Right.
– If you want to have a high or low risk tolerance,
I don’t care.
– But ultimately say, own up to it and say,
I listen to our lawyers and I agree with them.
This is too risky for our business.
– This is too risky.
– So I made the call.
– I made the call.
– Right.
– I made the call, they spooked me.
– Right.
– And I just don’t think it’s worth it.
It’s palpable.
And if it goes sideways, I think we can deal with the fallout.
That’s the conversation of which the lawyers are part of it.
So being decisive, I think, is about relationships.
When we have relationships where somebody says to us,
I believe in your vision, you got this.
The world needs what you’re trying to do.
You will find your courage to make decisions skyrocket.
– Yeah.
– When you don’t seek relationships and support from others,
you will gonna be alone in all your decisions.
And that’s where the fear creeps in.
– Yeah.
– Because you feel like you’re on an island.
You know, and I think the more senior you get
in an organization, whether you’re a young founder
or whether you’re a senior in a large corporate organization,
you know, it’s a very lonely place.
And we all know it.
We all talk about it.
When you’re not in those situations,
you don’t understand it.
– Yeah.
– And there, it is an incredibly lonely place
because there’s not a lot of people you can confide in.
When you have moments of crippling doubt,
are we doing the right thing here?
That last decision I made, that I just blow it,
you can’t go to your team and say,
I think I’ve completely screwed this one up.
You have to be vulnerable and open with your team,
but you can’t share that.
But you have to share it with someone.
– Right.
– And to be able to call a friend.
– Yes.
– And be like, dude, I think I completely screwed this up.
– Yeah, yeah.
– This is relationships.
Human beings need human beings.
– Yeah. – Done.
And the more human beings that you have in your life
that love you, care about you, trust you,
and you love them, care about them and trust them,
you will find yourself with a courage
and a confidence that few others have.
By the way, people who have that confidence
without relationships.
– Yeah.
– That to me is like psychotic.
– Right.
So if we want to unpack that a little bit
and say, okay, I’m in my late 40s.
Yeah, I just moved to LA six months ago.
Building a new network of trusted friendships,
relationships, it’s harder to do as you get older
and couples establish patterns.
They have kids now, there’s more responsibilities.
What if someone’s listening to be like, okay, great guys,
you’re telling me over and over again, I need relationships.
I get it.
I don’t have a whole heck of a lot.
– Right.
– What do I do?
– So I’m in the same place as you.
I’m a COVID transplant.
I’m gonna have friends in LA, some good friends in LA,
but expanding my networks proved to be very hard,
partially because LA doesn’t have serendipity.
I come from New York where you bump into people
all over the place at the time.
Here I go from my couch to my car to an office
or a conference room and then back,
or then reverse back away.
And you never bump into any, there’s no serendipity.
– Right.
– And so meeting people has to be prescriptive
and it’s very hard.
It’s very hard to meet people here.
And it’s Hollywood, so everybody’s a little bit aloof.
You get people’s cell phones,
but you’re not allowed to use them.
It’s a weird place.
– It is, yeah.
– So one of the things I’m doing,
and it’s imperfect, but I’m doing,
which is I’m leaning on my friends from not from here.
– Yeah.
– When I’m calling them up more.
– That’s what I’m doing as well.
– Yeah.
– And I’m finding ways that we can meet up somewhere,
or can you come out here or let me come out to you,
or why don’t we go away for a weekend together.
– Yes.
– When I’m realizing that a couple of days
of precious time is better than lots of fleeting moments.
– Yeah.
– And I spent a lot of time on the phone
with my friends who aren’t here.
– So funny how the phone’s made a comeback.
– I do more phone calls with friends remote now.
I actually want to hear them than texting.
It just feels more intimate.
– Also, I don’t like Zoom.
I don’t think well sitting.
I’m a pacer.
And so on a phone, I can pace.
– Yeah.
– I go for a rock.
I put on one of those weighted backpacks
and just go on some of these trails
and just call a friend, chat for a half hour.
– We now live in a world where, you know,
it’s considered rude to call without texting first.
I mean, really just don’t answer the call then.
– Right, I just call, yeah.
– I just call.
– If they’re that close a friend,
you should just feel the call.
– But I do with people I’m not that close with either
because I just think the phone is a beautiful magical
to hear voice.
– One more question for you.
We started off the conversation
talking about great leaders.
You mentioned Steve Jobs.
One of the people that I’ve been fortunate enough
to have on this show is Elon Musk a while ago.
He really admired him and, you know,
got to watch his career unfold
and him build some great companies.
Seems like he’s found his why.
That said, Twitter slash X was a huge head scratcher for me.
Do you think he kind of lost his way?
So let’s just take one step to the left
and say why is Elon Musk important?
Right?
There are plenty of very successful entrepreneurs
who, their success, they won the lottery.
You know, like right place, right time, right partner.
And some of the ones we admire
weren’t the ones who came up with the idea.
They’re just the ones who are leading the company.
– Sure.
– And then we’ll leave the names of those companies out
but you and I both know who they are.
And they won’t be able to repeat it.
Even if they’ve made hundreds of millions of dollars,
they won’t be able to repeat it, right?
Elon is important because he’s repeated it multiple times.
He’s the real deal.
– Real deal.
– Real deal, right?
So that’s important.
– Yes.
– He didn’t win a lottery.
Absolutely people bet against him
and he had so much passion and vision for what he was doing
that he proved all the naysayers wrong.
He made a very bad decision on Twitter, right?
He got backed into a corner, he backed himself.
– I don’t think he wanted to buy it at the end.
– I don’t think so.
I think he backed himself into a corner.
– Yeah.
– And he tried to get out of the deal, couldn’t.
Just as a side, I think it’s really funny.
The board members of Twitter and like leaders
that were like, we would never sell, how much?
Okay.
– Yeah, totally.
– How’s that idealism doing for you guys?
Turns out everyone’s got a price.
Anyway, I think Elon backed himself into a corner
because he’s always beaten the naysayers in the past.
People are saying, well, never doubt Elon.
– Right.
– Well, no, you can doubt Elon.
In this case, he doesn’t have a passion or a vision.
– Yes.
– Like he did for the others.
– The others were his ideas.
– Others were his ideas or, I mean, Tesla wasn’t his idea,
but he saw the potential.
– Right.
– The decisions he made were clearly to advanced
a greater good and he was willing
to take tremendous financial risk to do it.
In this case, he’s trying to make a company
that doesn’t make money, make money,
as opposed to advance some sort of greater good.
And it’s clearly, I mean, he keeps talking
about freedom of speech, but that’s not it.
– Yeah.
– He’s trying to look at the decisions that are being made.
– Yeah.
– I think he screwed the pooch.
I think he made a mistake.
And the sad part is, because I think he has a brand
and his brand is, look at the shit I get right.
I think he’s too intimidated, shy, embarrassed to say,
I blew it, right?
– Yeah.
– And if he would just come out and be like, look,
I made the biggest mistake in my career.
I got wrapped up in the excitement of it all.
I find myself buying something I didn’t want to buy.
We’ve all done it, but when you’re the world’s richest man,
it’s just a lot more expensive.
And at the end of the day, I don’t really want to do this.
It’s not my passion.
And I’m willing to sell Twitter to somebody
who actually has a vision for this thing.
You know, I don’t want to lose my shirt on it,
but you’ll get a good deal.
– Yeah.
– And I need to unload this thing.
And I screwed the pooch.
I don’t want to go back and focus my time energy
on the things that I actually love and care about.
– Oh, man.
– If he just said that, we’d all be fine with it.
– Yeah.
– We’d all be like, cool.
– Everyone would stand up and applaud.
– Everyone would stand up and applaud.
And what he’s doing, it’s unfortunately,
it’s very the times, which is deny, deny, deny, deny, deny.
– Right.
– Right?
Like nobody does anything wrong anymore.
If we look at all of his companies,
you can see there’s an idealism and that you can see
they kind of like fit a portfolio.
Like they kind of all belong in this fund.
This one doesn’t.
– It doesn’t.
Also, it’s a social product that I find
that it’s a different beast.
– Yeah.
– It’s not science.
– Guy with ass burger shouldn’t be running a social.
– Exactly.
– Look, it’s so fraught with irony.
One of his things that he said at the beginning was,
I think it’s irresponsible and bad
that one company should be deciding
what we say or don’t say.
So I’ve replaced that company with a person.
– Right.
– One person decides who we should be saying or not say.
– Yeah, I know.
– I mean, whatever.
We can talk about it.
Like he screwed up and I can’t imagine the pressure
he feels more importantly that he puts on himself.
– It’s gotta be so tough.
– You know, he’s still a human being.
– A hundred percent.
– Give the guy a little grace.
He screwed up.
We all do.
His was more expensive and more public
than the rest of ours.
– I’d much rather him working on
neuroscience related issues and working on this.
– Yeah, they exactly.
– Like every moment or day that he spends working on this,
he’s not helping us find solutions to energy problems.
He’s not helping us find solutions
to mental health problems.
– Which he’s damn good at.
– I want Elon to do the stuff that he’s great at
and I don’t want him to do Twitter.
– Yeah, same.
– We’re completely aligned.
– So what’s next for you?
You’ve got several successful bestselling books
that could just be your jam for the rest of your life.
– I’ve all but stopped doing in-person public speaking.
I do them occasionally,
but it’s basically not happening anymore.
Because it doesn’t work like it used to.
I believe in impact.
Impact is more important to me than money.
And when I was starting, I was proselytizing.
I was preaching a point of view in a way the world worked.
And most people in the room had never heard of me
or my ideas.
And so I came into preach and the delta
of how people felt when I came in,
when people felt when I came out.
And the lifestyle that I was living,
which was on the road all the time exhausting,
the pain was worth it.
And I’m a great, people like, you know,
you should never quit.
You have to have grit.
Or people like, well, you have to know when to quit.
My standard is very simple,
which is if the struggle or the sacrifice is worth it,
then keep doing it.
If the struggle or sacrifice doesn’t feel worth it,
then stop doing it, right?
You know you have cause
and you know that you’re doing the right thing.
When this sucks, but it’s worth it, right?
And so I hated it, but it was worth it.
I hated the lifestyle.
Now the delta is much smaller.
I’m coming to talk about ideas
that people have already read about or heard about.
Or I’m no longer proselytizing a group of people
who’ve never heard of my work.
And so I’m in this magical period of exploration.
I actually don’t know what I’m gonna do next.
And so I’m saying yes to things
that have no financial gain whatsoever,
but I’m just kind of like giving it a try
to see if I like it or not.
I know that it won’t be what I’ve been doing.
I like steep learning curves.
This is the curse of 10,000 hours.
Glad while I made this whole 10,000 hour things
that you have to achieve 10,000 hours or something
before you can achieve mastery.
And we all are in quote unquote pursuit of the 10,000 hours.
But what we forget,
and I firmly believe that everything is balanced.
Everything in the world is balanced.
Every advantage you have in the world,
there’s a disadvantage that comes
with whatever that thing is, always.
The world is always balanced and nature pours a vacuum.
And so there’s a downside to the 10,000 hours.
You talk to lots of people who have mastery.
You’ll find the same pattern is only one of a few things.
Boredom is one of them.
It was so exciting when the steep learning curve was steep.
And I have met directors and producers and VCs
and entrepreneurs and they’re so good at what they do.
They’re considered the best in their industry
and they’re out there.
They know how to make money.
They know how to make movies.
They know how to write books.
They’ve got bang, bang, bang.
And if you get them on a quiet night
when they’re a little bit tired,
probably a glass of whiskey or two in them,
they will absolutely all admit
that they’re bored out of their skulls
because there’s nothing exciting
about what they’re doing anymore.
It’s just rote.
– Just because it’s become second nature?
– Because it’s 10,000 hours.
They’ve got so much mastery.
It’s not exciting.
It’s the excitement of gaining 10,000 hours.
It’s actually more enjoyable for the human being.
I meet these really, really senior successful people
that privately admit that they’re bored.
– I wonder how Steph Curry does it.
I wonder how those professional basketball players
when they’re just like the top of their game,
how they stay motivated.
Like Kobe was really good at this.
If you saw the last dance,
Michael Jordan created narratives that were fake.
– Yeah, that’s right.
He was making shit up.
– He was making shit up.
He was making enemies.
– Yeah.
– He was not this great infinite minded guy
that we all thought he was.
He was the consummate finite player.
He was the best finite player in the world
where he would produce conflict that didn’t exist
to make himself so angry
that he was gonna can take you down.
– I mean, it was, that was crazy.
That was insane.
– It was crazy insight.
And I do think they get bored as well.
And I think it’s just like the next ring
and become the winning most of this
or the winning most team.
They just keep setting finite goals.
And that’s exciting for the short term,
but do they have long-term joy?
– Yeah, I don’t know.
– So boredom is one thing that I think a lot of people,
when you reach 10,000 hours,
I think the other thing is you find yourself,
like when you’re hammer every problem’s a nail.
And when you have mastery of something,
you see the whole world through that one lens.
And I think it creates a closeness to new.
And you see this a lot.
You see very successful CEOs, entrepreneurs
that miss significant changes in technology, for example.
And the number of CEOs who like,
didn’t see the internet as a thing.
– Right.
– I mean–
– Yeah, you look back and look at those old quotes
and they’re hilarious.
– Hilarious or like bomber who like,
shit all over the iPhone, like it’ll never be a thing.
Because no one’s gonna spend that amount of money
on a phone.
– You’re smarter than that.
But the problem is, it’s not because he’s dumb.
– Yeah.
– And it’s not because he’s blind.
And it’s not because he’s stupid.
It’s because when you have mastered something
and you’ve been doing that thing the same way
for 30 years, to the point where it’s made you rich
and famous and the top of the organization,
it is very, very hard to see the world
through any other lens than that lens.
– And whether you know it or not,
you’ve created a walled garden for yourself.
When I was at Google, the first thing I did,
when I landed inside and I was assigned
to their social products team and I was running mobile
for Google+, which ended up failing.
– Well done.
– Listen, I bounced.
I was speaking of leaving jobs quickly.
I was there for like four months.
And I went to Google Ventures.
And I just became an investor.
I knew there was no future there.
But yeah, that was horrible.
But one of the things I realized is like,
I’d gone to these product meetings
and there was like 30 people in the room.
And I’d start talking about what we were doing
that was novel and different
and that just wasn’t feature parody with Facebook.
And it was like, they were so of the mindset
of like, we’re Google, we can do anything.
We have scale.
They didn’t even use anyone else’s tools.
They were never installing other apps
or other competitors.
They weren’t playing.
They lost all of that.
They had their free lunches.
They had their soccer campuses.
They even had a half pipe on Google’s campus,
which I rode, which was actually pretty awesome.
But it was like, you’re so surrounded by like-minded people,
you don’t think to play and there’s no discovery.
And so I think that’s what happened with Bomber and others
when you don’t get a chance to actually get out there
and be a real person.
– And that’s the thing that made you successful
in the first place was the open-mindedness
of the childlike one.
– Play, yeah.
– You’re 100% right.
It’s the curse of the 10,000 hours.
It’s 10,000 hours plus, plus, plus,
which is why publishing didn’t invent the e-reader.
Amazon invented the e-reader, not publisher.
– Right, very confusing.
– Why is it that Netflix made streaming a thing
and not the movie and TV industry?
How did you guys miss that?
You could have, but you didn’t.
You can’t blame companies or industries
’cause companies and industries don’t make decisions.
It’s human beings who have achieved mastery,
who are now running organizations,
who are decision-making positions,
who literally cannot perceive the world
outside of the 10,000 hours of mastery
that they’ve achieved.
– For sure.
– And I’m at that point where I have 10,000 hours
of mastery in one little space
and it scares the shit out of me.
And so if there’s one thing I know,
which is to go be an idiot again.
– I love that.
– I need to start with four hours.
Okay, I’m gonna learn about venture.
I don’t know and understand anything about money, right?
I’ve never been motivated, I’m the money idiot.
And I’m sitting in these meetings
and they’re all using all this jargon.
And I am so clueless.
It is not fun, it is not comfortable, I feel dumb.
Everybody thinks I’m smart
because I’ve achieved something,
they think I know everything about everything, right?
And I’m trying to be dumb.
And I’m trying to find what I’m passionate about
that is worth really working hard
to not be dumb with the thing that I’m dumb about.
– What’s your point earlier?
I mean, it’s about asking questions
that you don’t know the answer to again.
– You’ll appreciate this.
So I got to know James Kars
who was the originator of the concept
of finite and infinite games before he died.
And when I first met him, of course, the burning question,
how’d you come up with that?
Right now, just as an aside for those
who don’t know what I’m talking about.
– Yeah.
– So Jim Kars was a philosopher and theologian.
He worked at NYU who wrote a book
in the mid-1980s called finite and infinite games
where he defined these two types of games.
It’s a cookie little philosophy book, right?
He defined these two types of games.
The finite game is defined as known players,
fixed rules, agreed upon objectives, football, baseball.
If there’s a winner necessarily,
you have to have a loser or losers.
But more important, there’s always a beginning,
a middle, and an end.
Then you have infinite games.
Infinite games are defined as known and unknown players,
which means you don’t necessarily know
who all the other players are
and new players can join the game at any time.
The rules are changeable,
which means every player can play however they want.
And there’s no such thing as winning.
You can only perpetuate the game.
The goal is to stay in the game as long as possible.
– Right, so life basically.
– Business, nobody wins business.
When Circuit City went bankrupt,
Best Buy didn’t win anything.
The game will change forms.
You don’t know who your competitors are necessarily.
New competitors can join.
Every company can run however they wanna run.
And no one’s ever declared the winner of business.
This is what Kars put out in the world.
And it dramatically impacted my work.
‘Cause I bought into his philosophy,
Hogan and Sinker, and I started to realize
if you listen to leaders,
they talk about being number one,
being the best or beating their competition.
Based on what?
Based on what agreed upon metrics,
objectives, and time frames.
So when you play to win in a game that has no finish line,
turns out you make a lot of stupid decisions
and you end up destroying trust, cooperation, and innovation.
And if you look, most companies today,
most large companies are not innovative.
They just buy smaller and more innovative companies.
The average lifespan of a company I think is 17 years,
which is abysmal, right?
Look at the damage that companies are doing
because they’re so short termist.
It’s all because they have a finite mindset
in the infinite game of business.
What Kars articulated was a truth.
A lot of people have theories,
finite game of games is a truth.
That is how the world works.
You have to play for the game you’re in.
So I got to know some.
And of course, when I met him the first time,
I sat down with him and was like,
I gotta ask, how did you come up with this?
And he was telling me that in the 1970s,
there were all of these salons.
So there were these intellectual salons
of which he was a part of,
where they would bring in people from different disciplines,
like mathematics and philosophy and engineering
to debate the topic of the day, which was game theory.
Game theory was all the rage in the 1970s.
And lots of theories were coming out of these salons, right?
So for example, the prisoner’s dilemma,
which many of us are familiar with,
that came out of one of these salons in the 1970s, right?
So he was in these salons and it occurred to him
that in all of these discussions,
they were always talking about winning and losing.
All of them.
Nobody was talking about playing.
Even the prisoner’s dilemma is about winning and losing.
And then he sort of like went home
with this problem he had stuck in his mind.
And he watched his kids.
And he saw when his kids played ping pong,
there was always screaming and yelling,
there was always fighting,
and there was always accusations of somebody cheating.
Every time.
– That doesn’t change with adults by the way, right?
– But yeah.
– But when his kids were like playing Lego,
they would sit there quietly for hours.
And one of the kids would leave for a little bit
and then come back later.
And the game would, the Legos would last for days.
And they would start and stop and start and stop.
And there was never any fighting.
And there was only cooperation.
– Mm-hmm.
– And he realized that we’re so obsessed
with winning and losing that we’ve forgotten
the value of playing and not all games have an end.
And business should be treated like a game
rather than a competition.
It should be treated like Lego more than baseball.
– Yes.
– And we overuse sports and war analogies
in business all the time.
– Yeah, hit a home run.
– ‘Cause we treat it like a game.
– Yeah.
– We have launches.
We have campaigns.
We have wins.
We have losses.
We give bonuses for accomplishment.
We talk about performance driven,
but we never talk about creativity.
– Yeah.
– We never talk about joy.
We never talk about cooperation or cross-pollination.
And this is the magic of great innovation
and great businesses.
And so you talk about the magic of play.
– Yes.
– Right?
One of the problems with 10,000 hours of mastery
or any kind of mastery is you become so good at something.
Now you wanna win every time you’re playing
because you’re the expert.
– Right.
– And there’s a joy in not worrying about the outcome.
– Hmm.
– There’s a joy in just playing.
And so I am looking for few opportunities to play baseball
and more opportunities to do leg-up.
– Hmm.
That’s interesting.
A few years ago, I picked up studying Zen
with a great Zen master out of Santa Fe.
And one of the things about Zen
is it is a dedicated practice.
You wanna get in your reps in terms of hours,
but you cannot have an outcome
because that pushes away.
– It defeats the point.
The West is more obsessed with finite
and I think Eastern philosophies
are more obsessed with infinite.
I learned that you are actually not present
until somebody else says you are.
Right?
Because you can’t be present by yourself.
I mean, you can, that’s one of the side effects,
but the true value of being present
is as a gift to another, right?
So let’s think about meditation.
For those who’ve ever practiced meditation,
what you’re supposed to do is sit still
and focus on one thing.
Whether it’s something you stare at,
whether it’s a mantra or a sound,
or the ocean or whatever it is,
you’re supposed to focus on one thing.
– Right.
– You can’t clear your mind, it doesn’t exist.
You focus on one thing.
And you learn to clear your mind
of all other thoughts except this one thing.
And if you have a thought about work,
you label it a thought.
You say, “Ah, that’s a thought.
“I’m gonna push that aside and we’ll deal with that later.”
And you find this tremendous calm and focus
and tremendous relaxation.
Okay, what was the point of all of that?
Just so you can feel good?
No, that’s the unintended by-product
that you feel good and you have all the health benefits.
The true benefit for me of practicing meditation
is that when I’m sitting with a friend,
they wanna tell me something amazing
that’s happening in their life,
or they wanna tell me something
that’s horrible that they’re dealing with.
I’m focused on one thing and one thing only,
what they’re telling me.
Every other thought, the car that just screeched,
don’t hear it anymore.
I have thoughts of things I wanna say,
and I label them thoughts.
I’m gonna say, “That’s a label of…”
I’m gonna deal with that later.
– You’re bringing it to real life.
– I’m bringing it to real life.
And at the end of the conversation,
I know that I have been present,
that all of that practice,
we call meditation a practice,
that all of that practice was worth it.
For this one moment when my friend says to me,
“Thank you for listening,”
or, “Thank you for being present,”
or, “I really feel heard.”
Thank you.
Now all of that meditation was worth it.
And all of the benefits that I derive are secondary.
The true benefit is the gift that I get to give
from working really hard in my own practice.
So we’ve made so many of these eastern practices
that are pro-social selfish.
We’ve made them checkboxes.
– We’ve made them checkboxes,
and we’ve made them only for us.
– Yes.
– And perpetuating that imbalance that America is so good at,
which is we’ve over-indexed on rugged individualism,
Maul Burma, and with hero-ized CEOs,
as if they did everything by themselves, right?
We’re all striving to be the hero.
We’re all striving to be influencers.
We’ve created heroes out of individuals
of which none of us succeed without groups of people
who believed in us, took bets on us,
were there for us,
let us cry on their shoulders,
or just cheered us on on a rainy day.
We’ve forgotten that the more we can focus on each other
and taking care of each other,
and what it means to be a good friend,
to be a good partner, to be a good leader,
to be a good follower, to be a good employee,
to be a good boss, to be a good,
all the relationship, friend,
that’s where true joy and success lies.
And play,
play, I think is the most magical of all,
play without a required income.
You start drawing, you start playing with Lego,
and a few days later, you decide to put it away.
Yeah, arbitrary, yeah.
And I’m trying to do that with my career.
I’m trying to play again.
That’s great, I love to hear that.
Must feel good, why it’s nerve-wracking.
You know, we talked about being uncomfortable,
I’m uncomfortable, I have no idea
what my future is gonna be.
But I’m okay with that.
That’s awesome.
What you did with me was beautiful.
Thank you again for that.
That was just a fun little few minutes of unpacking that.
Well, let’s just say, I wanted to go deeper on that.
Where do I go on your website?
Is there a specific course?
Yeah, yeah, there’s a whole thing about finding your why.
Okay, so that’s the one to sign up for.
That’s the one to sign up for.
Okay, awesome.
Simon, thank you so much.
This is great.
Oh, my pleasure, thanks for having me.
This has been great.
Yeah, it’s a joy, thanks.
I see something the rest of the world doesn’t see yet.
– Yeah.
– Well, I mean–
– Simon Sinek, popular at 50 million views on it.
– My initial conclusion was,
the good partnerships, you love the partner
and they’re offering you the ability
to expand your vision.
Though it won’t be perfect, no relationship is,
you still love coming to work
because you feel like you’re still advancing
the greater good in building this business.
Those are the partnerships we should be pursuing.
Discomfort is one of those things
that to learn to be uncomfortable
is nobody who’s ever achieved anything in the world
did it smoothly.
We all came close to zero if not hitting zero first.
And when you’re coming up to a stranger,
can you help me get out of this?
My answer is always the same as,
why would I get into mud with a stranger?
– Right. – I don’t know you.
Go ask somebody who loves you.
It’s safer to be vulnerable with me
because I’m a stranger.
It’s hard to be vulnerable
with somebody who actually knows me.
I don’t know the three most important words
that a young entrepreneur can ever learn.
It’s your story, it’s also my story.
I thought I had to have every answer
and if I didn’t, I thought I had to pretend that I did.
Let me tell you, you are who you are
and the rest of your life is simply an opportunity
to live in balance with that wire.
I’ll show you another way to find your wire.
Which is, and this is.
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– Simon, thank you for joining me.
– Thanks for having me.
– So great to have you on.
I’ve been a fan from afar.
– Thank you.
– Watching what you’ve done over the years
and your content and preparation for this interview.
I had to go and just check the numbers
of how you’ve blown up over the years.
I mean, it’s insane, so 56 million views or so
on Start With Why.
Did you have any idea it was gonna be that big?
– I mean, of course not.
It’s winning the internet lottery.
I knew that the talk resonated
because it wasn’t the first time I gave it.
I’d been giving the long version of that talk
for a few years.
I knew the content was resonant with people.
I knew it was a different way of seeing the world.
But of course, I could never have known
that it would do what it did.
Combined with the fact that the audio quality
is terrible and the video quality is terrible
and it’s living proof that it slick comes second.
– Yeah, I look back on that.
It’s not even HD.
– That’s terrible.
– Yeah, my microphone breaks in the middle of my talk.
– Yeah.
There’s a handful of books that have really changed
my thinking, especially around entrepreneurship
and leadership, zero to one.
There’s a handful of ones where I’m just like,
oh wow, there was some great insight there that happened.
Where did this come from?
Where was that aha moment for you where you’re like,
I see something that the rest of the world doesn’t see yet.
– Like most of these ideas, they’re rarely an aha moment.
It’s more like evolutionary steps.
The realization after many steps and this was no different.
I came from an advertising and marketing background
and I was always curious why some marketing worked
and some marketing didn’t.
I wasn’t the creative teams ’cause I could have
the same creative team make good stuff and bad stuff.
And it wasn’t just the clients.
I had clients that made good stuff and bad stuff.
And so I looked at sort of the great marketing
that I admired and I recognized that there was a pattern
that it all started with why they did what they did.
And I articulated the concept way back then
just to explain why some marketing
worked and some marketing didn’t.
That’s all it was.
And the original model was why, what, how.
The definitions were the same as they are now,
but it was why, what, how.
And I used to use that.
I started my own business and I used to use that
as my sort of pitch, you know.
And it wasn’t until much later I went to an event
at this black tie affair and I was just sort of
coincidentally seated next to somebody whose dad
was a neuroscientist when we just started talking,
making small talk.
Yeah, and she was telling me about Neuroscience 101.
And I was curious about it and came back
and started like Googling like crazy.
And I realized this little model that I had discovered
and the neuroscience perfectly overlapped.
I hadn’t discovered why marketing worked,
I discovered why people do what they do.
So I reached out to a famous neuroscientist
named Peter Weibrow, who was the head
of the Semmel Institute at UCLA,
which is the largest neuroscience institute in the world.
I don’t know how I got hold of him, but I did.
And I basically said, I need you to look at this stuff.
I’m gonna say this is related to neuroscience.
I need this blessed.
Yes.
So I like went to his house for a weekend,
just basically talk nonstop.
And I came in on Sunday morning and he was like fidgety.
And I’m like, what’s the matter?
He goes, it doesn’t match the neuroscience.
I’m like, well, what do you mean?
He goes, you need to switch what and how.
I’m like, done.
Yeah.
Maybe came why, how, what?
Yeah.
The definitions are always the same,
but to match the neuroscience of how brain work,
that’s what it was.
And then I started to realize that this thing had power.
At a later point, it saved me because I lost my passion
for my own work and hit sort of a really dark period.
And I realized that I knew what I did.
I knew how I did it, but I didn’t know why.
So these things all sort of collided.
Personal depression plus my exploration here.
And it all sort of came together.
I have at least a half dozen friends right now
that have landed in what they thought
was gonna be their dream job.
It typically happens via an acquisition.
It’s a tech entrepreneur.
They get acquired by a big company.
They’re now inside the belly of the beast
of something large.
And they have a couple of sayings.
It’s like vest in peace.
Or it’s just like, you’re just vesting
and kind of showing up and quiet quitting, right?
Which I’m sure you’ve heard about.
What’s going wrong there?
What’s happening?
Why are they feeling this way?
You’re asking something that’s,
something that happens two or three steps prior.
Okay.
The number of young, idealistic entrepreneurs
who start businesses and ethics matter to them
and treating their people right matters to them
and culture matters and all the things
that I write and talk about matters to them.
And they build these beautiful businesses
and then they sell them to the highest bidder,
not to the company that believes in their values
and has to maintain the culture, the highest bidder.
Right.
And the company goes to shit.
They change the ingredients of the product
because they go for something cheaper, et cetera, et cetera,
et cetera, you go down the line.
And they can rationalize it because they cashed out big.
They can rationalize that, no, we did it right.
And they didn’t.
That’s, be honest, they didn’t.
Why not take a little less money and sell it
to the right company who believes in the values
rather than just sell it to the highest bidder?
And so if they’re stuck in a place
where they don’t wanna be there,
well, that was their choice.
Like they chose that partnership.
That’s like marrying somebody just ’cause they’re pretty.
Yeah.
Right?
And then complaining that my marriage isn’t working
and we don’t get along.
I’m like, yeah, I don’t know how many marriage advice for you.
It’s hard though too ’cause you have stakeholders, right?
Well, that is another thing.
It’s the same trauma, which is, you know,
so many entrepreneurs who are looking for capital,
they take the biggest capital
from the most famous venture capitalist,
not less capital from the right venture capitalist.
That’s right.
So they chose their own partners
and then they’re surprised whether partners
are applying massive amounts of pressure on them
to make decisions that they don’t wanna make.
Yeah.
I don’t have a lot of sympathy, you know?
And we have reached the point now
where, and I can’t remember the statistic,
it’s overwhelming.
It’s something like 80% of companies are, you know,
venture capital or private equity backed.
And so we used to mock the public markets
that the pressure exerted by Wall Street
would force CEOs to make decisions
they knew were bad for their companies.
And we’re now at a point where private companies
are basically functioning like public companies
where the external pressures are so great.
That’s right.
That the number of young, brilliant,
fantastic, talented CEOs getting fired from their own companies.
I have a friend who just got fired from her own company
because she didn’t have control of it.
Yeah.
And she couldn’t make decisions.
They fired her because she was trying
to do the quote unquote right thing and follow the vision.
And they wanted to do the thing that made it prettier
to sell in a short period.
There’s an element of like, you made your bed.
And so there’s even a degree of,
look, I’m not in their position,
but there’s even a degree of irresponsibility.
Yeah.
There’s no choice to take the deal.
And now you’re dissatisfied with the deal.
You have sort of sellers remorse.
And so you’re going to quiet quit because you’re pissed off.
I’m like, they didn’t do anything wrong.
Right.
You took the deal.
I think there’s some soul searching to be done
in business writ large,
which is who we take money from and who we sell to.
Yeah.
Because I think a lot of good companies
actually don’t survive the founders
because of who we sell them to.
I can almost count it like clockwork
because I’ve seen so many of these deals
and I know what it is.
It’s a three year vest.
When you sell the company,
they put golden handcuffs on you for three years
and you can almost just mark the date.
And then you see a founder being like,
I’m leaving and it’s of course
right at the three year anniversary, right?
And they’re out.
And then if they were holding it together
with any duct tape or whatever else,
like everything seems to fall apart from there.
Unfortunately.
Good partnerships.
You love the partner.
You love the buyer.
And they’re offering you some sort of ability
to expand your vision.
You couldn’t do yourself,
which is why you took the deal.
That’s right.
Fundamentally, you come to an arrangement
where even though you have a boss now
and you didn’t have one before,
that there’s a degree of independence you have
to build this brand, which is what they want as well.
And though it won’t be perfect, no relationship is,
you fundamentally still love coming to work
because you feel like you’re still advancing
the greater good in building this business.
Right.
So those are the partnerships we should be pursuing.
Yes.
Yeah, that makes a ton of sense.
It’s almost like feel for the fire at that point.
Like you’re joining forces with someone
to help you expand and grow a lot faster.
What about individuals that are,
I see as individual contributors to an organization
and I see some of these resumes
when I’m looking to hire, say an engineer,
and you see bouncing around.
You see bouncing around
between different employment opportunities.
What advice do you give them
and how do you help coach someone
through finding their why?
Well, there’s a couple of different questions there.
You and I, when we were younger,
even if we hated our job,
we would never dream of quitting in less than one year.
Oh, 100%.
We couldn’t.
It would look so bad.
And we all knew that if you did that,
it would destroy your resume.
Yes.
It would create a bad narrative
about what kind of employee you were.
And I mean, it would have to be pretty toxic
for you to leave it under a year, right?
And so we held our nose and we made it to a year.
And this predominantly younger generation,
though it’s not exclusive,
but predominantly younger generation
is very comfortable quitting quickly
and sometimes for not good reasons.
And I’ve seen it happen,
which is the young people who are so confrontation avoidant,
they’d rather quit than go through the discomfort
of asking for a raise, for example.
For every action, there’s an equal opposite reaction.
There’s a finite mindedness to it,
which is how do I solve the immediate problem in front of me
without considering the long-term impact of that decision?
I’m not for or against the decisions.
I’m saying consider the long-term impacts.
And I’ve been public about this,
and I’ve been criticized for it by young people,
which is flash forward five or six years
and you’ve had seven jobs, right?
And whether you’re bouncing
because you think they’re all toxic
or whether you’re bouncing
because you’re just dialing for dollars, whatever it is.
In five or six years,
the new employer is looking at you
and you’re a certain age now,
which means I expect a certain level of maturity
and accomplishment.
– Yes.
– You haven’t had it
because you haven’t gone through the shit.
– Right.
– You keep jumping shit.
So I don’t even know that you’re qualified
for the senior position you’re applying for
that somebody else with seven years experience
could apply for, number one.
And number two, if I’m given two resumes,
one with somebody who’s bouncing around
and one who’s had two jobs over seven years,
I’ll take the one with two
because I’m not gonna trust
that this person’s gonna stick around
after I’ve trained them up and got them all in.
We have a few years
before we start seeing the repercussions,
but the repercussions are coming.
And again, I’m not saying don’t quit.
I’m saying just be cognizant
that there are implications
and maybe be a little slower.
– Do you think the problem there
is that they’re picking the wrong profession
and wrong job from the get-go
or they don’t have the grit to stick it out
during the hard times?
You mentioned this confrontation avoidant.
Is it because they are like,
this makes me uncomfortable.
I can’t handle it.
I’m out.
Or did I just pick wrong right away?
I know we’re generalizing, but–
– I mean, who knows?
But this idea of dream jobs is a funny thing, right?
– Yeah.
– Ain’t no such thing, number one.
Every job is imperfect,
like every relationship is imperfect.
And we live in a world that idealizes
both relationships and jobs.
And so when my relationship isn’t perfect
and my partner doesn’t do all the perfect things
and then I ban in that relationship
and I’m doing the same thing,
this job isn’t perfect and I have stress
and they want me to work late on a Thursday,
there’s a problem with pursuing the dream job
because it doesn’t exist.
Now, that’s not to say we should suffer either.
I believe you should have joy at work.
I believe you should be fulfilled by work.
I believe that you should be inspired
by the company you work for,
but you don’t have to like every day.
You can love your children,
you don’t have to like them every day.
You can love your job,
you don’t have to like it every day.
I think we confuse the two,
that there are days that I don’t like my job
and that’s the reason to quit.
But fundamentally, are you working in a place
where you feel seen, heard and understood?
Are you working in a place
that you feel like you’re growing as a human being,
that you actually are a better version of yourself
because you work here?
Are they pushing you and challenging you
to take on more responsibility
than maybe you even think you’re capable of?
And that’s uncomfortable.
And if you go back to Steve Jobs, for example,
and I know we herald him,
but he was pretty remarkable, right?
One of the things that Jobs did
is it was uncomfortable working at Apple.
And it wasn’t uncomfortable because he was mean,
although he wasn’t the nicest person in the world,
it’s because he saw potential in people
that they didn’t necessarily see in themselves.
And he pushed and pushed and pushed people.
And people who didn’t like being pushed, they quit.
But the people who were okay being pushed,
they all said I achieved more at this company
than I ever would have imagined.
Johnny Ive, this sort of middling designer,
Jobs sees something in him
that maybe he does or doesn’t even see in himself.
And he gets pushed and pushed and pushed and pushed.
He becomes one of the greatest designers
in modern history.
– I had a really long conversation with Tony Fidel
about this, working with Jobs.
And the growth comes from the discomfort.
– The growth comes from the discomfort.
I mean, look, there’s so many metaphors and analogies,
I love the one about the lobster.
– I haven’t heard the lobster one.
– So lobsters, the soft mass inside the shell
is what grows, that’s the origin.
The shell itself doesn’t grow.
It’s this hard thing that excretes out and hardens.
And as the lobster grows,
it starts to get very uncomfortable in its own shell
’cause it’s now bigger.
It’s like wearing clothes that are too small.
And only when it gets to that point,
does it then shed the shell and build a new one.
In other words, you can’t grow without being uncomfortable.
– Right, right.
Yeah, that’s so good.
– And that’s true.
I like to equate everything to personal relationships
because corporate relationships are relationships, right?
– Yeah.
– Which is every fight or uncomfortable situation
I ever had with my girlfriend.
Though I did not enjoy it,
though I wish we’d never had it.
Though sometimes I was to blame,
sometimes she was to blame,
more often than not, we were both to blame.
And when I say that just a quick aside,
usually in an argument,
we start accusing each other of who started it.
– Right.
– The reality is, yes,
absolutely somebody always started it
and the other person almost always poured gasoline.
– Yes.
– So you both have a culpability,
it doesn’t matter what started it,
you both made it worse.
– Right.
– Invariably, every uncomfortable conversation
or fight that we ever had,
though I hated every moment of it and so did she,
we ended up stronger and closer because of it.
– Yeah.
– Because there were lessons that were learned,
there were triggers that were realized,
there was language that was dissected.
And what we did was learn to fight,
not against each other, but against the problem.
– Mm-hmm.
– And I think it’s the same at work, right?
Which is when there’s pressure exerted,
is it me versus management?
Or is it management and me
versus whatever we’re trying to accomplish?
– Right.
– And good leaders know that
and good team members know that.
– Mm-hmm.
– It’s when it becomes adversarial,
us versus them.
– Yeah.
– And by the way, I blame leadership
as much as I blame employees.
Team members will go out for drinks and vent about work,
which I’m, by the way, totally healthy.
– Yeah.
– And I’m talking with that.
But sometimes narratives,
and especially in virtual and distributed workforces
where everybody’s wherever they are,
the rumor mills can spin out of control a lot quicker.
– Yes.
– And we blame management for what they did to us
or whatever.
But it happens at leadership as well.
The number of times I’ve sat in leadership groups,
including my own.
– Mm-hmm.
– Where we label someone dumb or lazy.
– Mm-hmm.
– Or inconsiderate or one foot out the door.
And we make jokes about,
ugh, here we go again.
We’re entitled or just go down the list.
And we label them.
We create a narrative about them.
And now we treat them that way.
– Mm-hmm.
– And though they may not know our narrative,
they know that they’re being treated a certain way.
– Mm-hmm.
– And so one of the things that is imperative
in any leadership team,
which is when one person finds themselves venting
about somebody where it’s creating a narrative
about another human being,
it’s imperative that somebody else on the leadership team
interrupt that narrative.
– Mm-hmm.
– And say, they could be lazy.
True, that’s definitely a possibility.
Or they’re overwhelmed.
– Right.
– Or we haven’t given them good instruction.
Or they’re struggling at home.
– Yeah, I was gonna say,
they’re going through something that we don’t know about.
There’s a list of things.
And so we treat them with empathy
and maybe check in on them.
I expect leadership to go first
’cause they should know better.
But whether it’s in a group of team members
about each other, more about management,
management about team members.
And again, I hold the leaders to a higher level
of accountability and if they act appropriately,
the team will act appropriately.
But we have to interrupt each other
with these kinds of narrative.
Discomfort is one of those things where
it’s good to be transparent about discomfort.
And it starts, again, leaders set the tone.
– Because it’s disarming.
– When you lie, hide and fake.
When you pretend that you got it all figured out.
People will think you got it all figured out.
And so they will pile on more and push you more
and give you more and expect more
because you said everything’s good.
And that’s when it becomes overwhelming
and that’s when you start blaming management
for mistreating you.
But hold on, right?
Whereas I’m a great believer
in just being totally transparent about discomfort.
And sometimes it’s real
and sometimes it’s perceived, for example.
And I had it happen recently.
One of my team members, she’s wonderful,
we’re a distributed workforce
so we don’t get a lot of face time, right?
So she’s never had a lot of one-on-one time with me.
You know, I see her corporate off-sites and stuff like that
and I see her on Zoom all the time.
But she’s never had one-on-one time with me.
And so we brought her out to LA
to have a one-day hackathon with me.
She’s young, she’s in her early mid-20s junior employee.
And she came clean.
She said, “I just need to tell you,
“I was really nervous about today.
“I don’t get us a lot of face time with you
“and I want to make sure I do right.”
And I got really prepared, but I’m really nervous.
And giving me that information was magical
because if she had come in all like ego and everything,
I would have ripped her writing apart
a lot more aggressively because she’s good.
But now I could just be like a little softer
or it’s a, “You’re doing great.
“I can just reinforce.”
‘Cause I know she’s feeling a little intimidated or fragile.
So saying, “I’m really excited about this project.
“I’m really excited about this new responsibility.
“If you’ve given me, I’m a little uncomfortable
“because I’ve never had this amount of responsibility.
“I really don’t want to screw it up
“and I want to do right by you
“and I do want to do right by me.”
And I don’t want to fail.
And simply just saying that means that a good leader
will be like, “Got it, I’m here, you’re good.”
And you feel supported in that discomfort.
– Yes, right?
– Uncomfortable isn’t the problem.
It’s feeling alone and uncomfortable.
It’s the problem.
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– A good leader can see the signs.
Virtual makes it much more difficult.
Yeah, working in a distributed workforce
makes it much easier to hide, lie and fake.
Body language doesn’t come across as easily.
Somebody’s a little bit fidgety, you can’t really see.
Doesn’t really show up on a Zoom call.
But I think discomfort is one of those things
that to learn to be uncomfortable
is probably the single greatest asset you could ever,
you know this, ’cause nobody’s ever achieved anything
in the world did it smoothly.
We all came close to zero if not hitting zero first,
all of us.
And Lionel Richie talks about this.
When he was younger, he had crippling,
debilitating stage fright.
Lionel Richie.
– Yeah.
– And he says there’s two types of people in this world.
Nobody has the absence of fear.
The two types of people in the world
are those who have fear and they take a step back
and there are those who have fear
and take the step forward.
And I always took the step forward.
– Yeah.
– Courage isn’t the absence of fear.
It’s being afraid and leaning into it.
And so to be uncomfortable and step forward
is perhaps the single greatest thing you can ever learn.
And what you discover is you’re surrounded
by people who wanna help you.
– Yes.
– 100%.
– Which is the most amazing thing to discover.
– This is one of my biggest mistakes.
You know, when I was in my early 20s
and I had my first startup,
I was pleasantly surprised in that it was my first go,
it was dig and it was the first social news app
and it exploded to tens of millions of users in six months.
– Yeah.
– And I was afraid. – That’s uncomfortable.
– Oh my God.
Well, here I am, college dropout, moved to the valley.
I was so intimidated by everyone around me,
the VCs I was getting introduced to, everyone else.
And I was scared to raise my hand
and say, “I don’t know the answer to this.”
Because everyone was looking to me as like someone
that had created something new and exciting.
And it wasn’t until actually two years into the company
where it was really strange.
It was a very small period of time
where dig was bigger, traffic-wise than Facebook.
And so Mark came to my office, Zuckerberg.
And he just asked a thousand questions.
And he was really probing me on so many different things
and admitting so many things that he just didn’t know.
And I was like, “Wow, I need to be more like this.”
– Exactly.
– Because here I am operating in this silo,
afraid, ashamed, and it’s not doing me any good.
I’m actually doing more harm to my business.
And once you have that unlock
and you realize it’s a massive strength
to have vulnerability and to raise your hand
and say, “I don’t know the answer to this.”
It’s a huge, huge unlock.
– I don’t know is the three most important words
any young entrepreneur can ever wear.
It’s your story, it’s also my story.
I had a small business and I was chief cook and bottle washer.
And I started having employees
and I had to be in every meeting
and I had to make every decision.
I thought I had to have every answer.
And if I didn’t, I thought I had to pretend that I did.
And A, the business doesn’t do well with that model.
But B, it’s crippling, like depression set in.
– Oh, 100%.
– Because you feel so alone in the hiding.
And it wasn’t until I learned to say,
“I don’t know or can you help me?”
Or learn to accept help when it’s offered.
The amount of help we’re offered on a daily basis
if you just counted it’s tons to say, “I’ll take that.”
And it is humiliating by the way.
Like I have some very successful friends
and they asked me what I’m going through
and I’ll talk about the stuff that I’m stuck with
or don’t know.
And these are very successful people
that I want to look good in front of.
The amazing thing is by being open to them,
the amount that they are there for me,
like that day of humiliation
was the greatest investment I ever made.
And I think that’s what you need to think of it is.
Like it’s an investment which is,
when you make an investment, you pay money, it hurts.
You take it out of your bank account,
it was a high number and it was a low number.
And you’re like, “Oh, this works.”
It’s an investment.
And sometimes it pays off.
I can’t say that it pays off all the time.
Sometimes it’s just humiliated.
– Yeah, right.
But that’s okay.
– And that’s okay.
– What was your personal story?
What was that moment you mentioned
where you didn’t want to go to work anymore?
And then how did you dig yourself out of that?
– Not ironically, I didn’t do it alone.
I reached a point where
I didn’t have the skillset to build the business.
I’d reached a certain level of growth
that I could achieve by myself
and needing to let go and not be in every meeting
and not make every decision.
That’s a critical point
because you literally can’t grow beyond a certain point
of if only one person can make all the major decisions.
I couldn’t let go.
And so I couldn’t grow, which means frustration.
Did not build systems, did not ask for help.
Ego was out of check.
And I don’t mean like, I thought I was everything.
I mean, I was pretending that I was everything.
And depression set in.
Didn’t want to wake up.
Didn’t find the joy in business ownership anymore.
And was really good at lying, hiding, faking.
I could pretend that I was happier, more in control
and more successful than I felt.
And by the way, so good that nobody could tell.
I mean, I was phenomenal.
And one friend could see through the armor.
One friend came to me and said something’s not right.
I don’t know what it is, but something feels off.
And for whatever reason,
probably ’cause she is really good at making a safe space.
I started to open up.
And she didn’t try and fix anything.
She didn’t have suggestions.
She simply let me be vulnerable.
And it’s not the act of being vulnerable per se.
It’s the act of not feeling alone in that vulnerability.
And that she could hold space for me so effectively.
I now had the courage to take all that energy
that I was using to lie, hide, and fake.
And I could take that energy to find a solution
to my malaise.
And the solution that I found was sitting right in front
of me the whole time, which is this thing
that I called the golden circle.
And that’s when I made the realization
that I knew what I did.
I knew how I did it, but I didn’t know why.
And that was the reason that I was stuck.
‘Cause I had no sense of purpose, cause, or belief.
And I became obsessed with understanding my why.
I learned my why, but more important,
I learned how to help others find theirs.
And I helped my friends find their ways.
Just because I wanted, it’s like you see a great movie.
You tell your friends to go see it.
No other reason, right?
There’s excitement.
And my friends, they quit their jobs
and started their own businesses,
or they found renewed joy in the jobs that they had.
To the same levels that I was experiencing, way higher.
And they asked me to talk to their friends.
And I would go to someone’s apartment in New York City
and stand in the living room
and talk about this thing called the why
and help people find their why for $100 on the side.
And my career took a weird turn completely by accident.
It was all organic.
But the point to the question was,
it was one person who held space.
We forget that we are social animals
and our very ability to survive
requires the help of other people.
If you fall asleep, you need someone
to watch for wild animals.
We just know good by ourselves.
We can’t solve complex problems by ourselves.
But in groups who are remarkable,
human beings hunted woolly mammoths.
– Yeah.
– No other animal could take down a woolly mammoth.
But we frail, weak human beings could.
Because the asset that we have that is our superpower
is our ability to cooperate.
And if you know that and you remember that,
that no human being can survive or thrive alone,
that we are fundamentally social animals,
you have to learn to ask for help
and you have to learn to offer it.
And that’s what I did.
That’s where I learned that lesson.
– One of the things that you said that struck me
is, and this is the mistake I make with my wife a lot,
I’ll admit it publicly,
is that I go into problem solving mode.
She’s got an issue and rather than just sit there
and hold space and have some empathy
for what she’s going through
and how something lands on her.
I’m like, let’s fix this.
And I’m like throwing out solutions and all this.
And then that’s not always the best.
– Men are particularly bad at it.
Men are usually in solution, not exclusively,
but tends to skew that way.
– That’s correct.
That is not a good idea.
And there’s a great video on YouTube
called It’s Not About the Nail.
Everybody can go look it up.
It’s one that has a bazillion views.
It’s many years old,
but it basically sums it up absolutely perfectly.
And by the way, you’re the same.
When you have a problem and somebody says,
well, why don’t you do this?
You end up being defensive and fighting with them
because you don’t actually want them to solve the problem.
You just want to feel safe in your stuckness.
And when somebody comes to you and says,
I’m struggling, just go tell me more.
What else?
By the way, you know how to do this
because you read all the books to do it with your children.
And when they say, daddy, I’m afraid.
That’s okay, you can be afraid.
But daddy this and you’re like, that’s okay.
You don’t try and fix their fear.
You hold space for their fear.
When they’re nervous,
you don’t try and fix their nervousness.
You don’t have to be nervous.
Don’t be nervous.
We’ve learned that that’s a terrible thing to do
with children.
You go, oh, I know it’s scary.
You affirm the feelings.
Well, why did you stop doing that
just because somebody is an adult?
Like you still have to affirm their feelings.
– It’s a great point.
– Honey, I’m nervous.
Honey, I’m scared.
Honey, I’m confused.
Honey, I’m angry.
– Yeah.
My girlfriend and I were,
she said something about something
and I had done something that upset her.
And I basically was like, well, that’s ridiculous.
And clearly I didn’t mean to.
How can you say that I did that?
Of course I didn’t do that on purpose.
– Right.
– You know, I’m full on defense mode.
I’m in full on like, it’s not really gaslighting,
but it’s a form of gaslighting,
which is like, I’m saying,
you can’t feel that way about that, right?
And after many rounds, I finally said,
if I were in your shoes, I would have felt the same.
And she said, thank you.
And the funny thing is what preceded that was,
I just need you to see it.
What if you were me?
Like she literally gave me the instruction.
– Right.
– I’m like, well, if I were in your shoes,
yeah, I probably would have felt the same
where you’re feeling now.
– Right.
– That was it.
– No, you’re right.
– Argument over.
– I’ve been there.
I’ve been in this exact conversation.
– Argument over.
– Yeah, 100%.
I’ve had it happen where I’m in a bad place
and I call a friend and told him basically like,
hey, I’m not feeling good.
And they start fixing and I get off the phone.
– Yeah.
– ‘Cause they make it worse.
– So true.
– I talk about this a lot, which is the idea
of sitting in mud, which is when we or our people
we love are in a bad place, they’re sitting in mud.
And our instincts, well intention,
is to pull them out of the mud, right?
To fix it.
Well, oh my God, that looks horrible.
Nobody wants to be in mud.
Let me pull you out of the mud.
And they don’t want to be pulled out of the mud.
– Right.
– But they don’t want you standing on the sidelines.
What they want, what loving friendship,
what loving relationship means is,
I’m gonna come and sit in the mud with you.
– Yeah.
– I don’t want to sit in the mud with you.
It’s no fun being in the mud with you,
but I’m gonna get in the mud with you.
– Well, that act alone will allow them to dig themselves
or climb their way out of the mud.
– Or, turn to you and say,
I think I’m ready to get out of the mud.
– Yeah.
– And then you can go into solution mode.
If a friend is depressed,
they just don’t want to get out of bed.
And we can’t make them get out of bed
and tell them they have to get out of bed.
Go to their house and get into bed with them.
And watch TV, watch movies all day, be depressed with them.
It’s not fun, it’s not productive,
but it makes them feel not alone.
– Right.
You’re matching their spirit at the moment.
– You’re making them feel not alone.
– Yeah.
– And usually when we try and fix someone’s problem,
usually when we try and pull them out of the mud,
what that makes them feel
is that they’re in the mud by themselves.
‘Cause we’re standing on high ground, on dry ground,
saying, let me pull you out.
– Right.
– Oh my God, look at you down there in the mud.
Let me pull you up here to the dry land,
which all that does is remind them that they’re alone.
– Right.
You must have just given everything
that you’ve been through in all your talks.
I’d imagine people come up to you randomly
or at talks, after talking to the line forms
and people wanna ask you questions.
If a young person comes to you looking to be pulled out
or in some way, it’s like, give me advice on this or that.
How do you empower them to make their own decisions?
How do you equip them to figure out their why?
‘Cause I’d imagine you can’t do that in two minutes.
– You can.
– Tell me.
– So finding the why is the easy part.
It’s like college graduation is called commencement.
– Yeah. – Beginning of something.
– Yeah.
– Well, finding your why is easy.
That’s why I called the book Start With Why.
‘Cause once you have it, now the work begins.
– Right.
– So again, there’s two questions there.
One is how to find the why and which I’ll tell you.
And the one is when you’re coming up to a stranger.
I mean, they don’t know me and I don’t know them.
– Mm-hmm.
– And they come up to me and say,
can you help me get out of this or, you know, hey.
– Right.
– And my answer is always the same as,
you don’t know me.
You know the image of me.
You know the image you’ve built of me.
I could be the worst qualified person to help you with this.
Go ask somebody who actually cares about you.
You know, you’re not my friend.
Like I like you, you’re seem very nice,
but why would I get into mud with a stranger?
– Right. – I don’t know you.
You know, go ask somebody who loves you.
Because it’s safer to be vulnerable with me
because I’m a stranger.
– Right.
– It’s hard to be vulnerable with somebody
who actually knows us.
– Mm-hmm.
– But that’s the thing you gotta do.
– Yes. – They’re asking the wrong person.
I’m sympathetic, but I’m the wrong person.
– Yeah.
– So where does a therapist fall on that?
Because you don’t know them,
but yet you can be vulnerable around them.
How do they fit into your thinking?
Like obviously it’s a useful tool to have a therapist.
– Therapists have said that I professionally
hold space for you.
That is my job.
– Right.
– Depending on the therapist, some of them have tools
to help you with whatever you’re dealing with, right?
So they can equip you with tools.
And I think therapists are one of the things that we need.
I don’t think they’re the only thing that we need.
I believe in therapy, I think it’s a good thing.
And the practice of being open with someone.
But I hope that you use that skill set with your friends.
Like what’s the point of learning the skill
if you’re not gonna apply it in other places?
– Right.
– And I think somebody who really struggles
with vulnerability should do therapy
because it is a good way to practice being vulnerable
with the people you really need to be vulnerable.
If you’re only vulnerable with your therapist and no one else,
I think that’s as much of a problem
as not being vulnerable to anybody.
It’s an education as much as it is a catharsis.
– Right.
– So going back to your question about finding your one.
– Yes. – Okay.
I’ll give you two answers.
– Okay.
– There are many ways to do it.
We’ve tried to make many tools available.
We have things in our website
that people can do to find their why.
I wrote a book called “Find Your One.”
– Yeah.
Your website’s got some great thank courses
and things that people can sign up for, which look awesome.
– Thank you.
– But there’s something called the friends exercise
which anybody can do and it’s fun.
Basically find a friend who loves you and you love them.
The kind of friend who,
if you call them at three o’clock in the morning,
you know that they would be there for you
and you would be there for them.
– Okay.
– Do not do this exercise with a spouse,
with a sibling, with a parent.
It does not work.
Those relationships are too close.
– Okay.
– Do it with a best friend and ask them the simple question.
Why are we friends?
And they’re gonna look at you like you’re crazy.
Because the part of the brain that controls
all of our feelings, love, loyalty, trust,
the limbic brain doesn’t control language.
It doesn’t control rational thought.
And so it’s very hard for us to
rationally articulate emotions,
which is why we use metaphors.
– Yeah, we’re hard-tempering in the words.
– Yeah, of course.
It’s a biological problem.
And so then you immediately convert the question,
because why is an emotional question?
And you start saying, “Come on, come on.”
What specifically is it about me
that I know that you would be there for me no matter what?
And again, they’re gonna hem and ha,
it’s very hard to put into words.
– What if they just give you high level like,
“Oh, you’re funny.” – They will.
They will.
That’s what they will do.
They’ll start describing you.
You’re funny, I trust you, you’re always there for me,
and you have to play devil’s advocate.
Great, that’s the definition of friend.
What specifically is it about me?
Or great, yes, all true,
but you get that from lots of other people.
What specifically is it about me?
Then I know you’d be there for me no matter what.
And they’re gonna go through a few rounds of this
where they’re just describing you
and describing this generic best friend archetype.
And eventually, because of discomfort, they will give up.
And they’ll go, “Look, man, I don’t know.
“All I know is,” and they’ll start describing themselves.
And this is what my friend said to me
when I did the exercise.
“Look, Simon, I don’t know.
“All I know is, I can sit in a room with you.
“I don’t even have to talk to you when I feel inspired.
“And I got goosebumps.”
So what they’ll do is they’ll say something about themselves
and you will have an emotional reaction.
You’ll get goosebumps, you’ll well up with tears,
because what they’re doing is articulating the value
having their life, which is the thing you give to the world,
which is your why.
And if you do this with multiple friends,
you will get very similar, if not the exact same answer,
because who you are in the world
is the space you fill in all of these people’s lives.
– And so is this idea what you give to them
or what you give to the world,
are you looking for a cross-section of agreement
amongst friends?
– No, no, no, no, no, no, no, no, no.
This is not subjective.
This is objective.
– Okay.
– Find as there’s common themes.
And your why is the value you have in the world.
It’s why not everybody likes you.
It’s not everybody wants what you have.
There are plenty of people who think
that my entire existence is cheesy.
I mean, I talk about inspiration.
I mean, literally what could be cheesier, right?
And are very dismissive.
Well, I’m not for them.
That’s okay.
It’s like some people like chocolate,
some people like vanilla.
It’s like, it’s all good.
But the people who love what I have to offer,
well, those people are either part of the movement.
They either, you know, buy, read a book
or watch a video or they’re my friends.
And we’re all kind of the same kind of person.
It’s like when Apple says think different,
who are they describing?
The answer is yes.
They’re describing their employees.
They’re describing their founders.
They’re describing their customers.
They’re describing the answers.
Yes.
They’re describing everyone who believes in that thing.
Well, it’s the same.
Your why is the thing you give to the world
and the people who value that
are the ones who want to receive it.
But it’s always gonna be you.
– Can we have different whys, multiple whys?
When do these whys form?
– Your why is fully formed by your mid to late teens.
The youngest why Discovery ever did was a 16 year old
and it worked perfectly.
We are all the products of our upbringing.
You are who you are based on the experiences you had
when you were young,
which made you quote unquote who you are.
And you don’t have a why for work and a why for home
because then how would I know which one’s the real you?
And one of those two places you’re lying, right?
And you can’t change your why every year
because then again,
how would you ever form trusting relationships
because I’d never know who you are.
Are you authentic this week?
But last week was a different why.
So it’s the concept of authenticity
literally couldn’t exist if your why could change.
You are who you are and the rest of your life
is simply an opportunity to live in balance
with that why or not.
I’ll show you another way to find your why,
which is pattern recognition.
I want you to tell me something you’ve done in your career
whether it was commercially successful or not
does not matter.
But something, a project you’ve worked on,
something specific that you did in your career
that you absolutely loved being a part of.
And if everything you ever did for the rest of your life
was like this one thing,
you’d be the happiest person in the life.
– I would say one of the things that I’ve enjoyed is-
– Loved.
– Loved, okay.
One of the things that I’ve loved is then
this is probably ego loaded.
So let’s just take it with that.
So I’ve loved getting the recognition from others
for discovering things earlier than anyone else.
– Tell me something specific that you did
that you loved the process, you loved being a part of it.
That if all of your projects were like this one,
’cause you’ve started multiple business,
many of them have had commercial success.
Some of them you enjoyed more than others.
And within those projects, there were things that happened.
– Sure.
– Things that went right or wrong,
new clients you landed, whatever it was.
Tell me one specific thing throughout this entire career
that you loved, you didn’t necessarily like it every day,
but you loved every, like this is the most exciting thing.
– I would say that is the invention of things that-
– Specific, invention of what?
– When we created social voting for the first time
and you could see the number go up
on a piece of content on the web,
this was before likes.
And because of something called asynchronous JavaScript,
you could actually watch as people socially voted
on things in real time and inventing that
and seeing that come to life and watching humans
in real time gather around articles
and watch them socially spread information.
That moment of creating that and seeing it take off
was just the creation process was a highlight
you would probably never get anywhere else.
That was a great just accomplishment for me and my team.
So of all the amazing things you’ve done
and you’ve had exits and all of the things
that people dream of, right?
What specifically was it about that,
about social voting that stands out in an entire career?
I think it’s because historically my kids
will look back on that and said,
dad did something that changed the world in some small way.
– Could say that about other things you’ve done.
Dad did something with dig,
dad did something with all those things.
My dad did was precursor to this or precursor to that.
Mark Zuckerberg came to my dad for advice.
So that, what specifically was about social voting
that was so exciting.
– Probably because it had the biggest impact.
I would say there’s been other things
like when I made the first intermittent fasting app,
severely obese people, my dad died of a heart attack.
We’re losing a lot of weight
and we started getting emails saying
it changed their lives.
And that was another aha moment where I was like,
this makes me feel so good.
Just because I know that I’d give anything
for another year with my dad
and to like think that I’m giving somebody else’s son
or daughter an extra year with their mom or dad
is a huge one for me.
So I think that’s another huge one.
– No, that’s good.
Tell me an early specific happy childhood memory,
something I can relive with you.
– Saturday mornings, my dad–
– One memory.
– One memory, catching a fish with my dad out on a boat.
– So this is a specific time you were at?
– Yeah, 100%.
– Okay, tell me about that day.
– Got up early.
I had never been fishing in the sea,
only kind of on lakes.
And my dad drove me about,
it was a multi-day trip to get up to the state of Washington.
We went out on a boat.
I was probably 10 years old
and I helped reel in like a 45 pound salmon.
I obviously couldn’t do it myself ’cause it’s tiny.
– Actually, I take that back.
The better memory was laying in the back of our truck bed,
looking up at my dad show me satellites for the first time.
And I saw a satellite camping with my dad.
That was like just a magical moment.
– Okay, tell me more about that.
– I just realized how much I loved my father.
And I just realized how special it was
that I got to spend some one-on-one time with him
and that he would take time out of his busy schedule
to show me attention, to teach me things.
It was difficult because my dad was a very verbally abusive
father to my mom.
And so he was always angry.
And so to see him being tender with me
was just a beautiful thing
because I got to see my dad in a place of like happiness,
which I didn’t see that often.
– And what was it about showing you the satellites?
– More one-on-one time.
And I just didn’t even know those things existed.
My late 40s satellites were a big deal way back in the day.
And now I will go watch SpaceX launches
outside of my balcony.
But back then it was like,
I just didn’t even know you could see him with a naked eye.
And if you’re laying on a clear enough night,
you can look up and you can actually track them
and see a satellite, which is amazing.
– Yeah, okay.
So what’s interesting about those stories,
seeing satellites with your dad
and when you talk about the intermittent fasting,
you use very similar language in both of them,
which is you talk about the opportunity
to have these moments, right?
My dad was an angry man
and I got to see him in tender times.
You talk about giving somebody else
the opportunity to spend more time with, right?
It’s about the discovery of beautiful things
that you didn’t know existed.
An angry man who could be tender.
A satellite you didn’t know you could see with a naked eye.
The discovery of changing and intermittent fast.
Even the uploading of things.
It’s really about, it’s recognizing that there’s community,
like there’s other people who connect.
And I think your why sort of exists in this arena.
I’m struggling to find the exact words for it.
– Yes, that feels right to me.
It’s very right to me.
Where the things that bring you joy
are when you give somebody the opportunity
to make a discovery that has a positive impact
in their lives to see something they didn’t see before.
And in all of those examples,
there was an element of like, I didn’t know that before.
I had never seen that before.
I didn’t know that could have an impact.
And there was a positive impact
whether it’s spending time with your dad.
And you said it beautifully,
which is giving somebody opportunity to spend more time
with their mother, father that you didn’t have.
And to some degree,
you’re becoming the best parts of your father,
which is to take quiet moments,
show somebody something
and let them discover something magical.
– Yeah.
I think that’s why I like playing with my kids so much.
– The things you get to show your kids.
– Yeah, and see through their eyes.
– See through their eyes.
– Yeah, it’s beautiful.
– It’s beautiful.
And even in the way you talk about social voting,
which is to see through other people’s eyes
what they find interesting.
So there’s discovery for the person
who’s learning it for the first time,
but there’s discovery for you who’s teaching them
because you don’t know where it’s gonna go.
– Right.
– And so there’s discovery on both sides.
– Yeah.
– So I think discover or discovery
is sort of your magic place, your magical place.
Anyway, your Y exists somewhere in the–
– No, that’s awesome.
I do wanna talk about what you do professionally for people
because I think this is important.
I noticed your site has some ways that people can sign up
and actually learn how to be coached through this.
More people need to do that.
And I wanna take it further now.
What do people do on your site?
– So we started the optimism company
with a very specific purpose,
which is to advance the idea of human skills.
I hate the term soft skills, hard skills and soft skills.
First of all, hard and softer opposites.
These things do not work against each other.
And also there’s nothing soft about soft skills.
There are hard skills and there’s human skills.
Hard skills are the skills you need to learn
to do the job you need to do.
And human skills, the skills you need to learn
to be a better human being.
And there’s a great irony in being human, right?
Like cats don’t have to work very hard to be cats.
They’re just naturally good at being cats.
But we have to actually do a lot of work
to be good human beings.
It’s frustrating and annoying.
And we built the optimism company
to completely focus on teaching people
the human skills they need to be better human beings.
And to advance that ability to cooperate and socialize.
– Is that both personally and professionally?
– It’s you, right?
So when I teach you better listening skills,
when I teach you how to have a difficult conversation,
when I teach you how to have an effective confrontation.
Now we teach it in a work context
because that’s where the people are.
But the reality is those skills are useful everywhere.
I like to make the joke that in the,
there’s an entire section of the bookshop called self-help.
And there’s no section of the bookshop called help others.
And what we need is to advance the help others industry.
And that starts with teaching people the human skills
of how to not only be a better version of yourself,
but more important, which is how to be a good partner,
friend, colleague, coworker, boyfriend, girlfriend,
brother, sister, son, daughter,
mother, father to somebody else.
Because all of these relationships, boss, employee,
dad, mom, brother, sister, they’re all cooperative.
None of them are solo.
They all involve a relationship.
Almost every label we have for people
involves some sort of relationship.
You can’t be a leader if nobody’s following you.
You can’t be a follower if there’s nothing to follow.
All of these things is a relationship.
Even when people talk about their faith,
I’m a follower of X.
Well, that’s a relationship.
That’s how they describe faith.
And so that’s what the optimism is singularly focused on,
which is how we teach people the human skills
to be better human beings.
That’s awesome.
I was picking to the website and I noticed
there was a couple of things you mentioned on the site
that you teach people the courage to lead
and then also conflict resolution.
How do you teach someone to resolve conflict?
So many of these skills, the foundational skill
of a lot of them is listening, right?
Like we talked about it before with you and your wife,
you fix everything.
One of what you need to do is learn to listen.
You work really hard to learn to listen to your kids,
but then you abandon the skill at work
or in your adult relationships, right?
And so conflict resolution, we have conflict at work.
We have disagreements, we have misunderstandings.
We feel triggered by certain things that people say,
whether they said it on purpose or by accident.
We feel pressure, we react badly.
There’s conflict everywhere.
And I don’t believe that world peace, for example,
is the absence of conflict.
I think that’s nonsense, right?
We live in a world with no conflict or war.
No, not gonna happen, right?
To me, world peace is the ability
to resolve conflict peacefully.
There’s gonna be conflict,
but how do you resolve it peacefully?
And you see it at work all the time.
People yell at each other, people quit out of anger,
people fire out of anger.
Conflict is gonna happen.
How do we resolve our conflicts peacefully?
You’re gonna have conflict in your relationships.
How do you resolve conflict peacefully?
So for me, conflict resolution is that very difficult skill
of when you’re angry,
you still have the skill to hold space for somebody else.
That’s so hard because when someone is triggered,
everything goes out the window.
And it’s just like, all of a sudden it’s all about emotion.
How do you train yourself to say,
let me pause this emotion and set aside for a second
and listen, what’s the process like?
Part of it is you have to have a game plan
going into every conflict.
You wanna make these decisions before you get to conflict.
You don’t wanna be in conflict
and then having to come up with strategy.
You need to master these skills before the conflict
so you’re prepared.
Whether they’re athletes or military,
they talk about muscle memory.
Then you practice and practice and practice
and practice and practice.
You don’t quote unquote, have to think in the stressful time
because you can just quote unquote, rely on your training.
– Interesting.
– Very similar.
– So you offer that type of training?
– Well, I mean, if you do these kinds of trainings,
then you’re doing them in artificial environments.
– Is it role-playing?
What type of training is it?
– The role-playing, we expect people to go do themselves.
But the point is all of these things,
even if you learn the skill, you have to go practice it.
So I’ll give you one example.
My girlfriend, we talk to each other very openly
when we’re not in conflict,
that when we fight, we don’t want it to be me versus you,
we want it to be us versus the problem.
So we know that.
So both of us have that mindset.
So when conflict does arise, we both have the right mindset.
And sometimes it takes us a little to get back to it.
Or we can say to each other, hey, hey, hey,
I’m not trying to be right here.
I’m trying to solve this problem.
And then we’re the minds of the person.
But I’ll give you a real-life example
that actually happened where we went down
that horrible rabbit hole of who started it.
If you hadn’t done this, then I wouldn’t have done that.
Well, if you hadn’t done that,
then I wouldn’t have done this.
I mean, it sounds like some Middle East conflict,
which is like we’re both blaming each other
for what had started.
And it was getting worse and worse and worse
and more aggressive.
And it occurred to me in that fight,
this is going nowhere.
This is intractable.
– This is gonna end up on–
– This is just not–
– You on the couch or something.
– This is one of us is gonna storm out.
If you just flash forward 10 minutes,
there’s no peaceful resolution to this journey we’re on.
Where we’re pointing out what I did right
and what she did wrong.
And she’s pointing out what I did wrong
and what she did right, right?
And I literally interrupted.
I said, okay, this is going nowhere, new rules.
We’re gonna reverse the script here
because right now I’m pointing out everything
I’m doing right and you’re doing wrong
and you’re doing the same, new rules.
From now on, I’m gonna tell you what I did wrong
and what you did right and I’ll go first.
– Wow.
– And I said, here’s what I did wrong
and here’s what you got right.
And she goes, well, yeah, here’s what I got wrong
and here’s what you got right.
– That’s beautiful.
– And I said, well, here’s what I got wrong
and you got right.
– And in five minutes or less,
the tension had been released.
We realized that both of us were trying.
Neither of us was evil.
Both of us were doing things right
and both of us had accountability.
– Yeah.
– And in that moment, it just petered out.
– That’s beautiful.
– You’re taking the knob and just turning it down enough
to where you can have a sensible conversation again.
– But I created rules.
– Yes.
The rules of engagement are this.
We’re gonna continue to fight
but we are operating from this script.
Me right, you wrong.
I’m just gonna flip the script.
Me wrong, you right.
– Yeah.
– And let’s just see what happens.
– Do you use that every time?
Or is that just–
– No, I didn’t.
That was spontaneous in the moment.
– That’s amazing.
– I’ve never done that before.
But I’m gonna do it again.
– Yeah.
– But the point is, is like doing it once even,
the next time you go down that path,
I don’t have to go down the path and get it really tense
’cause I can stop it immediately like, look,
I hear what you’re saying
and I definitely have some culpability here.
– Yeah.
– I definitely did this wrong and you did this right.
I can do it immediately now.
But the point is, these are skills.
– Right.
– Learnable, practicable skills and they’re muscles.
If you don’t use them, they’re gonna atrophy.
And this is what we’re trying to teach.
We’re trying to teach a host of these skills
that by themselves, they’ll help a little bit.
But the more of these skills we master,
the better colleagues,
– Yeah.
– Boyfriends, girlfriends, brothers, sisters, fathers,
mothers, sons, daughters, leaders, employees,
the better we become team members, colleagues,
any kind of human relationship.
– It was a big blind spot for me for a long time,
which is, I was a computer geek as a kid.
So back in our day, it was not cool to be a computer geek.
So I always made fun of a lot.
– Sure.
– So I was socially awkward and I had a really hard time
getting into my teens and then 20s,
going into a new situation without applying alcohol,
because alcohol for me was like a crutch, right?
I’ve since course corrected that,
but I’ve had to realize that when I stopped alcohol,
I have to build new muscles again.
I have to build new muscles around social interactions.
One on one, I’m fine.
I can turn it on for a while and I’m fine,
but there’s things that you have to kind of
figure out how to build that muscle around
so you can become proficient in it.
When you meet someone that is like,
I’m socially awkward.
I am not advancing my career,
the classic one is afraid to ask for a raise,
but let’s just say I’m not outgoing enough
to inspire confidence by the leaders of my organization.
Is that something that you believe
that we can learn and improve upon?
– So social awkwardness is not the problem.
I’m discomfort asking for difficult things
is not the problem.
I’m socially awkward.
You see me in a crowd, I’m useless.
I’m the one standing in the corner.
– So am I.
– I’m an over-sharer, mainly out of discomfort.
You know, talk too much, come on too strong.
It’s all discomfort.
Years of failed dates, you know?
– Yeah.
– Just social awkwardness.
And what I’ve learned is that those are not the problems.
The problem is confidence.
And I use social awkwardness or ADHD or introversion
or any of these excuses for whatever weirdness that I feel.
Right?
And I’m a great believer that none of these things
are right or wrong, they just are, you know?
You can be socially awkward as an extrovert,
you can be socially awkward as an introvert, right?
They just are.
And again, it goes back to asking for help
and just owning it, right?
Let’s be vulnerable, let’s be open
about our social awkwardness.
Let’s put it out there, let’s let people know.
I say it all the time, like I’m really socially awkward.
I say it on dates.
It’s a release, right?
It’s like putting it on the table.
So if I have a moment,
I’m not beating myself up in my head, right?
– Which can compound, right?
– And now it’s all me, it’s all me in my narrative, right?
– Yeah.
– And so the most important thing
is just owning it with confidence.
So here’s an example.
I’m really uncomfortable asking for a raise.
This is really hard for me, right?
That’s not owning it.
How about, hey, I’m so uncomfortable
having this conversation with you right now,
like I know I need to ask for a raise,
but I don’t wanna ask for a raise
’cause it makes me really uncomfortable,
but can we have the conversation anyway, please?
Right?
Yeah.
Or when you’re out with somebody,
meeting somebody for the first time,
like I’m really socially awkward and I’m an introvert
and I’m probably gonna say something
that’s gonna make you uncomfortable.
Like that’s just got creeper vibes only.
– Yes.
– Right?
– Yeah, that’s like I’ll follow you
out of the bar in a situation.
– Yeah, that’s so uncomfortable to even hear,
even though it’s well-intentioned
in its explanation, versus just so you know,
I’m probably like totally socially awkward.
I’m probably gonna say something
that’s gonna make you uncomfortable,
make me uncomfortable.
It’s gonna happen ’cause I’m just socially awkward that way.
You can hear the difference in tone.
– Right.
– When you just own it.
– Yes.
– When you’re just confident about who you are.
– It’s a great point.
– And so all the things that we talk about,
we’re trying to fix the symptoms,
but the cause is that you’re just not owning who you are.
– Right.
– And you can own your strengths
and you can own your awkwardness.
– Yeah.
– Just as an aside, I don’t believe
in strengths and weaknesses.
I believe we have characteristics and attributes.
And in the right contexts, those things are strengths.
And in the wrong contexts, those things are weaknesses.
So nothing that we have in our personalities
is inherently a strength or a weakness.
It’s all contextual, right?
So I work hard to be aware of my characteristics
and attributes, and I work hard to learn
when those things are to my advantage
and when those things are to my disadvantage.
And I work hard to put myself in situations
where who I am is more likely to be an advantage
than a disadvantage, right?
So for example, I’m disorganized,
chronically disorganized, right?
And I remember I was a young entrepreneur
at a networking event, socially awkward, introvert,
not very good at the stuff.
And I met a guy who, he’s like,
this time what you have to say is amazing.
I want to work with you.
Here’s my card, right?
Amazing.
And if I was organized, I would be texting him
from the taxi on the way home
or at least emailing him the next day.
Pleasure to meet you.
All of that stuff.
Well, I lost the business card.
Yeah, I don’t know what I did with it, right?
I had it and I lost it.
Two weeks later, I found it at the bottom of a briefcase.
And so I emailed him.
I don’t know if you remember when we met a couple weeks ago.
I just wanted to reach back out.
And he wanted to work with me more
’cause he thought I was busy.
That’s amazing.
So is being disorganized a strength or weakness?
The answer is it depends, right?
In some contexts, it is really not helpful.
In some contexts, it’s an accidental strength,
introverted and a little bit quiet, right?
And intimidated by, like you don’t know
what to say in a room, strength or weakness.
Well, at a networking event, it’s not gonna help you, right?
When you have to go around the room
and do all that kind of stuff.
But if you’re in a meeting and you’re the quiet one,
nobody knows if you’re an idiot or a genius.
And you’re the listener.
And they’re just waiting.
So a huge strength.
And so all of the things that I know about me
and when I thrive and when I fail,
when I’m happy and when I’m struggling,
I figure out what the characteristics and attributes are
and work very hard to put myself in situations,
find jobs, find clients, find opportunities
that are more likely to result in me
having those characteristics and attributes
work to my advantage
versus simply chasing the money,
chasing the client, chasing the opportunity,
finding myself in a situation
where this is not gonna work to my advantage.
– And do you believe those characteristics
and attributes can be enhanced?
Some people I know, they just can’t make a decision
for the life of them.
They can’t move forward.
Is that something where you look and say,
well, that’s kind of your DNA.
That’s an attribute or a characteristic.
That’s who you are.
Or we can actually take who you are
and enhance something
to make that a better, more smoother process for you.
– Yeah, I don’t think that’s necessarily
characteristic or attribute.
– Okay.
– What’s underlying that is risk tolerance, accountability.
– Yeah, so how do we improve risk tolerance?
– So risk tolerance and accountability
come from the relationships, believe it or not, right?
So this is why people say, the lawyers say we can’t do that.
– Right.
– The lawyers don’t make the decision on this.
– Right, right.
– The lawyers said I can’t do it.
That’s not a lawyer’s job.
And any lawyer who says you can’t do this
is actually not doing the job.
Lawyers have one job, advise you on risk.
There’s a lot of risk if you do that.
And you’re the one who’s supposed to assess the risk reward
and decide if the risk is worth it.
– Yeah.
– And if it’s not worth it, then say no.
But if you think it is worth it, then say yes.
– Every time I hear a CEO say that, it’s such bullshit.
– And when anybody says, the lawyer said we can’t,
they’re abdicating the responsibility
of making a decision.
– Yeah.
– It’s a weak leader, right?
Yes, take counsel from your attorneys.
– Right.
– Absolutely.
But ultimately, you’ve got to take a risk or not.
– Right.
– It’s your choice.
– Right.
– If you want to have a high or low risk tolerance,
I don’t care.
– But ultimately say, own up to it and say,
I listen to our lawyers and I agree with them.
This is too risky for our business.
– This is too risky.
– So I made the call.
– I made the call.
– Right.
– I made the call, they spooked me.
– Right.
– And I just don’t think it’s worth it.
It’s palpable.
And if it goes sideways, I think we can deal with the fallout.
That’s the conversation of which the lawyers are part of it.
So being decisive, I think, is about relationships.
When we have relationships where somebody says to us,
I believe in your vision, you got this.
The world needs what you’re trying to do.
You will find your courage to make decisions skyrocket.
– Yeah.
– When you don’t seek relationships and support from others,
you will gonna be alone in all your decisions.
And that’s where the fear creeps in.
– Yeah.
– Because you feel like you’re on an island.
You know, and I think the more senior you get
in an organization, whether you’re a young founder
or whether you’re a senior in a large corporate organization,
you know, it’s a very lonely place.
And we all know it.
We all talk about it.
When you’re not in those situations,
you don’t understand it.
– Yeah.
– And there, it is an incredibly lonely place
because there’s not a lot of people you can confide in.
When you have moments of crippling doubt,
are we doing the right thing here?
That last decision I made, that I just blow it,
you can’t go to your team and say,
I think I’ve completely screwed this one up.
You have to be vulnerable and open with your team,
but you can’t share that.
But you have to share it with someone.
– Right.
– And to be able to call a friend.
– Yes.
– And be like, dude, I think I completely screwed this up.
– Yeah, yeah.
– This is relationships.
Human beings need human beings.
– Yeah. – Done.
And the more human beings that you have in your life
that love you, care about you, trust you,
and you love them, care about them and trust them,
you will find yourself with a courage
and a confidence that few others have.
By the way, people who have that confidence
without relationships.
– Yeah.
– That to me is like psychotic.
– Right.
So if we want to unpack that a little bit
and say, okay, I’m in my late 40s.
Yeah, I just moved to LA six months ago.
Building a new network of trusted friendships,
relationships, it’s harder to do as you get older
and couples establish patterns.
They have kids now, there’s more responsibilities.
What if someone’s listening to be like, okay, great guys,
you’re telling me over and over again, I need relationships.
I get it.
I don’t have a whole heck of a lot.
– Right.
– What do I do?
– So I’m in the same place as you.
I’m a COVID transplant.
I’m gonna have friends in LA, some good friends in LA,
but expanding my networks proved to be very hard,
partially because LA doesn’t have serendipity.
I come from New York where you bump into people
all over the place at the time.
Here I go from my couch to my car to an office
or a conference room and then back,
or then reverse back away.
And you never bump into any, there’s no serendipity.
– Right.
– And so meeting people has to be prescriptive
and it’s very hard.
It’s very hard to meet people here.
And it’s Hollywood, so everybody’s a little bit aloof.
You get people’s cell phones,
but you’re not allowed to use them.
It’s a weird place.
– It is, yeah.
– So one of the things I’m doing,
and it’s imperfect, but I’m doing,
which is I’m leaning on my friends from not from here.
– Yeah.
– When I’m calling them up more.
– That’s what I’m doing as well.
– Yeah.
– And I’m finding ways that we can meet up somewhere,
or can you come out here or let me come out to you,
or why don’t we go away for a weekend together.
– Yes.
– When I’m realizing that a couple of days
of precious time is better than lots of fleeting moments.
– Yeah.
– And I spent a lot of time on the phone
with my friends who aren’t here.
– So funny how the phone’s made a comeback.
– I do more phone calls with friends remote now.
I actually want to hear them than texting.
It just feels more intimate.
– Also, I don’t like Zoom.
I don’t think well sitting.
I’m a pacer.
And so on a phone, I can pace.
– Yeah.
– I go for a rock.
I put on one of those weighted backpacks
and just go on some of these trails
and just call a friend, chat for a half hour.
– We now live in a world where, you know,
it’s considered rude to call without texting first.
I mean, really just don’t answer the call then.
– Right, I just call, yeah.
– I just call.
– If they’re that close a friend,
you should just feel the call.
– But I do with people I’m not that close with either
because I just think the phone is a beautiful magical
to hear voice.
– One more question for you.
We started off the conversation
talking about great leaders.
You mentioned Steve Jobs.
One of the people that I’ve been fortunate enough
to have on this show is Elon Musk a while ago.
He really admired him and, you know,
got to watch his career unfold
and him build some great companies.
Seems like he’s found his why.
That said, Twitter slash X was a huge head scratcher for me.
Do you think he kind of lost his way?
So let’s just take one step to the left
and say why is Elon Musk important?
Right?
There are plenty of very successful entrepreneurs
who, their success, they won the lottery.
You know, like right place, right time, right partner.
And some of the ones we admire
weren’t the ones who came up with the idea.
They’re just the ones who are leading the company.
– Sure.
– And then we’ll leave the names of those companies out
but you and I both know who they are.
And they won’t be able to repeat it.
Even if they’ve made hundreds of millions of dollars,
they won’t be able to repeat it, right?
Elon is important because he’s repeated it multiple times.
He’s the real deal.
– Real deal.
– Real deal, right?
So that’s important.
– Yes.
– He didn’t win a lottery.
Absolutely people bet against him
and he had so much passion and vision for what he was doing
that he proved all the naysayers wrong.
He made a very bad decision on Twitter, right?
He got backed into a corner, he backed himself.
– I don’t think he wanted to buy it at the end.
– I don’t think so.
I think he backed himself into a corner.
– Yeah.
– And he tried to get out of the deal, couldn’t.
Just as a side, I think it’s really funny.
The board members of Twitter and like leaders
that were like, we would never sell, how much?
Okay.
– Yeah, totally.
– How’s that idealism doing for you guys?
Turns out everyone’s got a price.
Anyway, I think Elon backed himself into a corner
because he’s always beaten the naysayers in the past.
People are saying, well, never doubt Elon.
– Right.
– Well, no, you can doubt Elon.
In this case, he doesn’t have a passion or a vision.
– Yes.
– Like he did for the others.
– The others were his ideas.
– Others were his ideas or, I mean, Tesla wasn’t his idea,
but he saw the potential.
– Right.
– The decisions he made were clearly to advanced
a greater good and he was willing
to take tremendous financial risk to do it.
In this case, he’s trying to make a company
that doesn’t make money, make money,
as opposed to advance some sort of greater good.
And it’s clearly, I mean, he keeps talking
about freedom of speech, but that’s not it.
– Yeah.
– He’s trying to look at the decisions that are being made.
– Yeah.
– I think he screwed the pooch.
I think he made a mistake.
And the sad part is, because I think he has a brand
and his brand is, look at the shit I get right.
I think he’s too intimidated, shy, embarrassed to say,
I blew it, right?
– Yeah.
– And if he would just come out and be like, look,
I made the biggest mistake in my career.
I got wrapped up in the excitement of it all.
I find myself buying something I didn’t want to buy.
We’ve all done it, but when you’re the world’s richest man,
it’s just a lot more expensive.
And at the end of the day, I don’t really want to do this.
It’s not my passion.
And I’m willing to sell Twitter to somebody
who actually has a vision for this thing.
You know, I don’t want to lose my shirt on it,
but you’ll get a good deal.
– Yeah.
– And I need to unload this thing.
And I screwed the pooch.
I don’t want to go back and focus my time energy
on the things that I actually love and care about.
– Oh, man.
– If he just said that, we’d all be fine with it.
– Yeah.
– We’d all be like, cool.
– Everyone would stand up and applaud.
– Everyone would stand up and applaud.
And what he’s doing, it’s unfortunately,
it’s very the times, which is deny, deny, deny, deny, deny.
– Right.
– Right?
Like nobody does anything wrong anymore.
If we look at all of his companies,
you can see there’s an idealism and that you can see
they kind of like fit a portfolio.
Like they kind of all belong in this fund.
This one doesn’t.
– It doesn’t.
Also, it’s a social product that I find
that it’s a different beast.
– Yeah.
– It’s not science.
– Guy with ass burger shouldn’t be running a social.
– Exactly.
– Look, it’s so fraught with irony.
One of his things that he said at the beginning was,
I think it’s irresponsible and bad
that one company should be deciding
what we say or don’t say.
So I’ve replaced that company with a person.
– Right.
– One person decides who we should be saying or not say.
– Yeah, I know.
– I mean, whatever.
We can talk about it.
Like he screwed up and I can’t imagine the pressure
he feels more importantly that he puts on himself.
– It’s gotta be so tough.
– You know, he’s still a human being.
– A hundred percent.
– Give the guy a little grace.
He screwed up.
We all do.
His was more expensive and more public
than the rest of ours.
– I’d much rather him working on
neuroscience related issues and working on this.
– Yeah, they exactly.
– Like every moment or day that he spends working on this,
he’s not helping us find solutions to energy problems.
He’s not helping us find solutions
to mental health problems.
– Which he’s damn good at.
– I want Elon to do the stuff that he’s great at
and I don’t want him to do Twitter.
– Yeah, same.
– We’re completely aligned.
– So what’s next for you?
You’ve got several successful bestselling books
that could just be your jam for the rest of your life.
– I’ve all but stopped doing in-person public speaking.
I do them occasionally,
but it’s basically not happening anymore.
Because it doesn’t work like it used to.
I believe in impact.
Impact is more important to me than money.
And when I was starting, I was proselytizing.
I was preaching a point of view in a way the world worked.
And most people in the room had never heard of me
or my ideas.
And so I came into preach and the delta
of how people felt when I came in,
when people felt when I came out.
And the lifestyle that I was living,
which was on the road all the time exhausting,
the pain was worth it.
And I’m a great, people like, you know,
you should never quit.
You have to have grit.
Or people like, well, you have to know when to quit.
My standard is very simple,
which is if the struggle or the sacrifice is worth it,
then keep doing it.
If the struggle or sacrifice doesn’t feel worth it,
then stop doing it, right?
You know you have cause
and you know that you’re doing the right thing.
When this sucks, but it’s worth it, right?
And so I hated it, but it was worth it.
I hated the lifestyle.
Now the delta is much smaller.
I’m coming to talk about ideas
that people have already read about or heard about.
Or I’m no longer proselytizing a group of people
who’ve never heard of my work.
And so I’m in this magical period of exploration.
I actually don’t know what I’m gonna do next.
And so I’m saying yes to things
that have no financial gain whatsoever,
but I’m just kind of like giving it a try
to see if I like it or not.
I know that it won’t be what I’ve been doing.
I like steep learning curves.
This is the curse of 10,000 hours.
Glad while I made this whole 10,000 hour things
that you have to achieve 10,000 hours or something
before you can achieve mastery.
And we all are in quote unquote pursuit of the 10,000 hours.
But what we forget,
and I firmly believe that everything is balanced.
Everything in the world is balanced.
Every advantage you have in the world,
there’s a disadvantage that comes
with whatever that thing is, always.
The world is always balanced and nature pours a vacuum.
And so there’s a downside to the 10,000 hours.
You talk to lots of people who have mastery.
You’ll find the same pattern is only one of a few things.
Boredom is one of them.
It was so exciting when the steep learning curve was steep.
And I have met directors and producers and VCs
and entrepreneurs and they’re so good at what they do.
They’re considered the best in their industry
and they’re out there.
They know how to make money.
They know how to make movies.
They know how to write books.
They’ve got bang, bang, bang.
And if you get them on a quiet night
when they’re a little bit tired,
probably a glass of whiskey or two in them,
they will absolutely all admit
that they’re bored out of their skulls
because there’s nothing exciting
about what they’re doing anymore.
It’s just rote.
– Just because it’s become second nature?
– Because it’s 10,000 hours.
They’ve got so much mastery.
It’s not exciting.
It’s the excitement of gaining 10,000 hours.
It’s actually more enjoyable for the human being.
I meet these really, really senior successful people
that privately admit that they’re bored.
– I wonder how Steph Curry does it.
I wonder how those professional basketball players
when they’re just like the top of their game,
how they stay motivated.
Like Kobe was really good at this.
If you saw the last dance,
Michael Jordan created narratives that were fake.
– Yeah, that’s right.
He was making shit up.
– He was making shit up.
He was making enemies.
– Yeah.
– He was not this great infinite minded guy
that we all thought he was.
He was the consummate finite player.
He was the best finite player in the world
where he would produce conflict that didn’t exist
to make himself so angry
that he was gonna can take you down.
– I mean, it was, that was crazy.
That was insane.
– It was crazy insight.
And I do think they get bored as well.
And I think it’s just like the next ring
and become the winning most of this
or the winning most team.
They just keep setting finite goals.
And that’s exciting for the short term,
but do they have long-term joy?
– Yeah, I don’t know.
– So boredom is one thing that I think a lot of people,
when you reach 10,000 hours,
I think the other thing is you find yourself,
like when you’re hammer every problem’s a nail.
And when you have mastery of something,
you see the whole world through that one lens.
And I think it creates a closeness to new.
And you see this a lot.
You see very successful CEOs, entrepreneurs
that miss significant changes in technology, for example.
And the number of CEOs who like,
didn’t see the internet as a thing.
– Right.
– I mean–
– Yeah, you look back and look at those old quotes
and they’re hilarious.
– Hilarious or like bomber who like,
shit all over the iPhone, like it’ll never be a thing.
Because no one’s gonna spend that amount of money
on a phone.
– You’re smarter than that.
But the problem is, it’s not because he’s dumb.
– Yeah.
– And it’s not because he’s blind.
And it’s not because he’s stupid.
It’s because when you have mastered something
and you’ve been doing that thing the same way
for 30 years, to the point where it’s made you rich
and famous and the top of the organization,
it is very, very hard to see the world
through any other lens than that lens.
– And whether you know it or not,
you’ve created a walled garden for yourself.
When I was at Google, the first thing I did,
when I landed inside and I was assigned
to their social products team and I was running mobile
for Google+, which ended up failing.
– Well done.
– Listen, I bounced.
I was speaking of leaving jobs quickly.
I was there for like four months.
And I went to Google Ventures.
And I just became an investor.
I knew there was no future there.
But yeah, that was horrible.
But one of the things I realized is like,
I’d gone to these product meetings
and there was like 30 people in the room.
And I’d start talking about what we were doing
that was novel and different
and that just wasn’t feature parody with Facebook.
And it was like, they were so of the mindset
of like, we’re Google, we can do anything.
We have scale.
They didn’t even use anyone else’s tools.
They were never installing other apps
or other competitors.
They weren’t playing.
They lost all of that.
They had their free lunches.
They had their soccer campuses.
They even had a half pipe on Google’s campus,
which I rode, which was actually pretty awesome.
But it was like, you’re so surrounded by like-minded people,
you don’t think to play and there’s no discovery.
And so I think that’s what happened with Bomber and others
when you don’t get a chance to actually get out there
and be a real person.
– And that’s the thing that made you successful
in the first place was the open-mindedness
of the childlike one.
– Play, yeah.
– You’re 100% right.
It’s the curse of the 10,000 hours.
It’s 10,000 hours plus, plus, plus,
which is why publishing didn’t invent the e-reader.
Amazon invented the e-reader, not publisher.
– Right, very confusing.
– Why is it that Netflix made streaming a thing
and not the movie and TV industry?
How did you guys miss that?
You could have, but you didn’t.
You can’t blame companies or industries
’cause companies and industries don’t make decisions.
It’s human beings who have achieved mastery,
who are now running organizations,
who are decision-making positions,
who literally cannot perceive the world
outside of the 10,000 hours of mastery
that they’ve achieved.
– For sure.
– And I’m at that point where I have 10,000 hours
of mastery in one little space
and it scares the shit out of me.
And so if there’s one thing I know,
which is to go be an idiot again.
– I love that.
– I need to start with four hours.
Okay, I’m gonna learn about venture.
I don’t know and understand anything about money, right?
I’ve never been motivated, I’m the money idiot.
And I’m sitting in these meetings
and they’re all using all this jargon.
And I am so clueless.
It is not fun, it is not comfortable, I feel dumb.
Everybody thinks I’m smart
because I’ve achieved something,
they think I know everything about everything, right?
And I’m trying to be dumb.
And I’m trying to find what I’m passionate about
that is worth really working hard
to not be dumb with the thing that I’m dumb about.
– What’s your point earlier?
I mean, it’s about asking questions
that you don’t know the answer to again.
– You’ll appreciate this.
So I got to know James Kars
who was the originator of the concept
of finite and infinite games before he died.
And when I first met him, of course, the burning question,
how’d you come up with that?
Right now, just as an aside for those
who don’t know what I’m talking about.
– Yeah.
– So Jim Kars was a philosopher and theologian.
He worked at NYU who wrote a book
in the mid-1980s called finite and infinite games
where he defined these two types of games.
It’s a cookie little philosophy book, right?
He defined these two types of games.
The finite game is defined as known players,
fixed rules, agreed upon objectives, football, baseball.
If there’s a winner necessarily,
you have to have a loser or losers.
But more important, there’s always a beginning,
a middle, and an end.
Then you have infinite games.
Infinite games are defined as known and unknown players,
which means you don’t necessarily know
who all the other players are
and new players can join the game at any time.
The rules are changeable,
which means every player can play however they want.
And there’s no such thing as winning.
You can only perpetuate the game.
The goal is to stay in the game as long as possible.
– Right, so life basically.
– Business, nobody wins business.
When Circuit City went bankrupt,
Best Buy didn’t win anything.
The game will change forms.
You don’t know who your competitors are necessarily.
New competitors can join.
Every company can run however they wanna run.
And no one’s ever declared the winner of business.
This is what Kars put out in the world.
And it dramatically impacted my work.
‘Cause I bought into his philosophy,
Hogan and Sinker, and I started to realize
if you listen to leaders,
they talk about being number one,
being the best or beating their competition.
Based on what?
Based on what agreed upon metrics,
objectives, and time frames.
So when you play to win in a game that has no finish line,
turns out you make a lot of stupid decisions
and you end up destroying trust, cooperation, and innovation.
And if you look, most companies today,
most large companies are not innovative.
They just buy smaller and more innovative companies.
The average lifespan of a company I think is 17 years,
which is abysmal, right?
Look at the damage that companies are doing
because they’re so short termist.
It’s all because they have a finite mindset
in the infinite game of business.
What Kars articulated was a truth.
A lot of people have theories,
finite game of games is a truth.
That is how the world works.
You have to play for the game you’re in.
So I got to know some.
And of course, when I met him the first time,
I sat down with him and was like,
I gotta ask, how did you come up with this?
And he was telling me that in the 1970s,
there were all of these salons.
So there were these intellectual salons
of which he was a part of,
where they would bring in people from different disciplines,
like mathematics and philosophy and engineering
to debate the topic of the day, which was game theory.
Game theory was all the rage in the 1970s.
And lots of theories were coming out of these salons, right?
So for example, the prisoner’s dilemma,
which many of us are familiar with,
that came out of one of these salons in the 1970s, right?
So he was in these salons and it occurred to him
that in all of these discussions,
they were always talking about winning and losing.
All of them.
Nobody was talking about playing.
Even the prisoner’s dilemma is about winning and losing.
And then he sort of like went home
with this problem he had stuck in his mind.
And he watched his kids.
And he saw when his kids played ping pong,
there was always screaming and yelling,
there was always fighting,
and there was always accusations of somebody cheating.
Every time.
– That doesn’t change with adults by the way, right?
– But yeah.
– But when his kids were like playing Lego,
they would sit there quietly for hours.
And one of the kids would leave for a little bit
and then come back later.
And the game would, the Legos would last for days.
And they would start and stop and start and stop.
And there was never any fighting.
And there was only cooperation.
– Mm-hmm.
– And he realized that we’re so obsessed
with winning and losing that we’ve forgotten
the value of playing and not all games have an end.
And business should be treated like a game
rather than a competition.
It should be treated like Lego more than baseball.
– Yes.
– And we overuse sports and war analogies
in business all the time.
– Yeah, hit a home run.
– ‘Cause we treat it like a game.
– Yeah.
– We have launches.
We have campaigns.
We have wins.
We have losses.
We give bonuses for accomplishment.
We talk about performance driven,
but we never talk about creativity.
– Yeah.
– We never talk about joy.
We never talk about cooperation or cross-pollination.
And this is the magic of great innovation
and great businesses.
And so you talk about the magic of play.
– Yes.
– Right?
One of the problems with 10,000 hours of mastery
or any kind of mastery is you become so good at something.
Now you wanna win every time you’re playing
because you’re the expert.
– Right.
– And there’s a joy in not worrying about the outcome.
– Hmm.
– There’s a joy in just playing.
And so I am looking for few opportunities to play baseball
and more opportunities to do leg-up.
– Hmm.
That’s interesting.
A few years ago, I picked up studying Zen
with a great Zen master out of Santa Fe.
And one of the things about Zen
is it is a dedicated practice.
You wanna get in your reps in terms of hours,
but you cannot have an outcome
because that pushes away.
– It defeats the point.
The West is more obsessed with finite
and I think Eastern philosophies
are more obsessed with infinite.
I learned that you are actually not present
until somebody else says you are.
Right?
Because you can’t be present by yourself.
I mean, you can, that’s one of the side effects,
but the true value of being present
is as a gift to another, right?
So let’s think about meditation.
For those who’ve ever practiced meditation,
what you’re supposed to do is sit still
and focus on one thing.
Whether it’s something you stare at,
whether it’s a mantra or a sound,
or the ocean or whatever it is,
you’re supposed to focus on one thing.
– Right.
– You can’t clear your mind, it doesn’t exist.
You focus on one thing.
And you learn to clear your mind
of all other thoughts except this one thing.
And if you have a thought about work,
you label it a thought.
You say, “Ah, that’s a thought.
“I’m gonna push that aside and we’ll deal with that later.”
And you find this tremendous calm and focus
and tremendous relaxation.
Okay, what was the point of all of that?
Just so you can feel good?
No, that’s the unintended by-product
that you feel good and you have all the health benefits.
The true benefit for me of practicing meditation
is that when I’m sitting with a friend,
they wanna tell me something amazing
that’s happening in their life,
or they wanna tell me something
that’s horrible that they’re dealing with.
I’m focused on one thing and one thing only,
what they’re telling me.
Every other thought, the car that just screeched,
don’t hear it anymore.
I have thoughts of things I wanna say,
and I label them thoughts.
I’m gonna say, “That’s a label of…”
I’m gonna deal with that later.
– You’re bringing it to real life.
– I’m bringing it to real life.
And at the end of the conversation,
I know that I have been present,
that all of that practice,
we call meditation a practice,
that all of that practice was worth it.
For this one moment when my friend says to me,
“Thank you for listening,”
or, “Thank you for being present,”
or, “I really feel heard.”
Thank you.
Now all of that meditation was worth it.
And all of the benefits that I derive are secondary.
The true benefit is the gift that I get to give
from working really hard in my own practice.
So we’ve made so many of these eastern practices
that are pro-social selfish.
We’ve made them checkboxes.
– We’ve made them checkboxes,
and we’ve made them only for us.
– Yes.
– And perpetuating that imbalance that America is so good at,
which is we’ve over-indexed on rugged individualism,
Maul Burma, and with hero-ized CEOs,
as if they did everything by themselves, right?
We’re all striving to be the hero.
We’re all striving to be influencers.
We’ve created heroes out of individuals
of which none of us succeed without groups of people
who believed in us, took bets on us,
were there for us,
let us cry on their shoulders,
or just cheered us on on a rainy day.
We’ve forgotten that the more we can focus on each other
and taking care of each other,
and what it means to be a good friend,
to be a good partner, to be a good leader,
to be a good follower, to be a good employee,
to be a good boss, to be a good,
all the relationship, friend,
that’s where true joy and success lies.
And play,
play, I think is the most magical of all,
play without a required income.
You start drawing, you start playing with Lego,
and a few days later, you decide to put it away.
Yeah, arbitrary, yeah.
And I’m trying to do that with my career.
I’m trying to play again.
That’s great, I love to hear that.
Must feel good, why it’s nerve-wracking.
You know, we talked about being uncomfortable,
I’m uncomfortable, I have no idea
what my future is gonna be.
But I’m okay with that.
That’s awesome.
What you did with me was beautiful.
Thank you again for that.
That was just a fun little few minutes of unpacking that.
Well, let’s just say, I wanted to go deeper on that.
Where do I go on your website?
Is there a specific course?
Yeah, yeah, there’s a whole thing about finding your why.
Okay, so that’s the one to sign up for.
That’s the one to sign up for.
Okay, awesome.
Simon, thank you so much.
This is great.
Oh, my pleasure, thanks for having me.
This has been great.
Yeah, it’s a joy, thanks.
Kevin sits down with the renowned author and motivational speaker Simon Sinek. They discuss the importance of understanding one’s “why,” the journey of building impactful leadership, and the nuances of personal and professional growth. They also explore the dynamics of leadership, the importance of building trust, and the role of vulnerability in personal and professional relationships. Lastly, Simon discusses the 10,000-hour rule and breaks down finite and infinite games in terms of business.
Guest Bio and Links:
Simon Sinek is a renowned author, motivational speaker, and organizational consultant. He is known for popularizing the concept of “Why,” his insights on leadership, culture, and business have inspired millions worldwide. His TED Talk on “How Great Leaders Inspire Action” is one of the most viewed talks on the platform.
Listeners can learn more about Simon Sinek at his website, on IG @simonsinek, and on YouTube @SimonSinek
Partners:
Manscaped: 20% off precision-engineered grooming tools
LMNT: Electrolyte drink mix. Grab a free sample pack
Facet: Personalized financial planning. Get your $250 enrollment fee waived
Resources:
Kevin’s Newsletter: Join 100,000+ subscribers
Simon’s Blog: The Optimism Company Blog
Simon’s Books
Simon Sinek: The Number One Reason Why You’re Not Succeeding | E145 | The Diary of a CEO
Finite and Infinite Games: A Vision of Life as Play and Possibility by James P. Carse
Show Notes:
* (0:00) Introduction
* (1:00) Manscaped: 20% off precision-engineered grooming tools
* (2:15) LMNT: Electrolyte drink mix. Grab a free sample pack
* (3:45) The success of “Start With Why”
* (5:45) The beginning of ‘why, what, how’
* (11:55) How to help coach someone to find their ‘why’
* (14:30) The problem of pursuing a dream job
* (18:30) The importance of vulnerability in leadership
* (22:17) Facet: Personalized financial planning. Get your $250 enrollment fee waived
* (23:52) Kevin’s Newsletter: Join 100,000+ subscribers
* (24:50) “To be uncomfortable is probably the single greatest asset you could ever, you know this because nobody who’s ever achieved anything in the world did it smoothly.” -S.Sinek
* (27:05) The three most important words for an entrepreneur to learn
* (31:55) The problems with problem-solving mode
* (32:30) It’s not about the nail
* (34:15) How to listen vs. trying to fix everything during a conflict
* (36:30) How to find ‘your why’
* (38:35) Simon explains how to find your why through the friends exercise
* (40:35) “Because what they’re doing is articulating the value you have in their life, which is the thing you give to the world, which is your why. And if you do this with multiple friends, you will get very similar, if not the exact same answer, because who you are in the world is the space you fill in all of these people’s lives.” (friendship exercise) -S.Sinek
* (41:55) Question: Can you have multiple ‘whys’ in life?
* (42:45) Using pattern recognition to find your ‘why’
* (49:45) The concept of human skills versus hard skills
* (52:00) Kevin and Simon discuss conflict resolution
* (58:15) How to deal with being socially awkward
* (1:08:00) Elon Musk purchasing Twitter
* (1:12:55) What’s next for Simon
* (1:14:25) The 10,000 hour rule
* (1:20:00) The concept of finite and infinite games
Connect with Kevin:
Website: kevinrose.com
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YouTube: @KevinRose
This is a public episode. If you’d like to discuss this with other subscribers or get access to bonus episodes, visit www.kevinrose.com/subscribe
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