0:00

Where was that aha moment for you? I

0:02

see something the rest of the world doesn't

0:04

see yet. Yeah. Well, I mean, Simon Sinek

0:06

popular at 50 million views. I mean, my

0:08

initial conclusion was, good partnerships, you love the

0:10

partner. And they're offering you the ability to

0:12

expand your vision. Though it won't be perfect,

0:14

no relationship is, you still love coming to

0:17

work because you feel like you're still advancing

0:19

the greater good and building this business. Those

0:21

are the partnerships we should be pursuing. Discomfort

0:23

is one of those things that to learn

0:25

to be uncomfortable is nobody who's ever achieved

0:27

anything in the world did it smoothly. We

0:29

all came close to zero, if not

0:32

hitting zero first. And when you're

0:34

coming up to a stranger, can you help me get

0:36

out of this? My answer is always the same as,

0:38

why would I get into mud with a stranger? I

0:40

don't know you. Go ask somebody who loves you. It's

0:42

safer to be vulnerable with me because I'm a stranger.

0:44

It's hard to be vulnerable with somebody who actually knows

0:46

me. I don't know the three most important words that

0:49

a young entrepreneur can ever learn. It's your story. It's

0:51

also my story. I thought I had to have every

0:53

answer. And if I didn't, I thought I had to

0:55

pretend that I did. Let me tell you, you are

0:57

who you are. And the rest of your life is

0:59

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thanks to Element for sponsoring today's show. Simon,

3:33

thank you for joining me. Thanks for having me. So

3:35

great to have you on. I've been a fan from

3:37

afar. Thank you. Watching

3:39

what you've done over the years and your content. In

3:41

preparation for this interview, I had to go and just

3:44

check the numbers of how you've blown up over the

3:46

years. I mean, it's insane. So

3:49

56 million views or so on Start

3:52

With Why. Did you have any idea

3:54

it was going to be that big? I mean, of

3:56

course not. It's winning the internet lottery. Yeah, I knew that the

3:58

talk was going to be like that. resonated because it wasn't the

4:01

first time I gave it. I'd been giving

4:03

the long version of that talk for a

4:05

few years. I knew the content was

4:08

resonant with people. I knew it was a different way

4:10

of seeing the world, but of course I could never

4:12

have known that it would do what it did. Combined

4:15

with the fact that the audio quality is terrible

4:17

and the video quality is terrible and it's

4:19

living proof that it's slick

4:22

come second. Yeah, I look

4:24

back on that. It's not even HD. That's

4:26

terrible. My microphone breaks in

4:28

the middle of my talk. Yeah. There's

4:31

a handful of books that have really

4:33

changed my thinking, especially around entrepreneurship and

4:35

leadership, zero to one. There's a handful of

4:37

ones where I'm just like, oh wow, there was some

4:39

great insight there that happened. Where

4:41

did this come from? Where was that aha

4:43

moment for you where you're like, I see

4:46

something that the rest of the world doesn't

4:48

see yet. Like most of

4:50

these ideas, they're rarely an

4:52

aha moment. It's more like evolutionary

4:55

steps. The realization after many steps, and this

4:57

was no different. I came

4:59

from an advertising and marketing background and I was always

5:02

curious why some marketing worked and some marketing didn't. Wasn't

5:06

the creative teams, because I could have the same creative team

5:08

make good stuff and bad stuff. It

5:10

wasn't just the clients. I had clients that made good

5:12

stuff and bad stuff. So I looked at the great

5:14

marketing that I admired and

5:16

I recognized that there was a pattern that

5:19

it all started with why they do what they did.

5:21

I articulated the concept way

5:24

back then just to explain why some marketing worked and some

5:26

marketing didn't. That's all it was. And

5:28

the original model was why, what, how. The definitions were the same

5:30

as they are now, but it was why, what, how. And I

5:32

used to use that. I started my own business. I used to

5:34

use that as my sort of pitch. And

5:36

it wasn't until much later I went to an

5:38

event at this black tie affair and I was

5:41

just sort of coincidentally seated next to somebody whose

5:43

dad was a neuroscientist and we just started talking,

5:45

making small talk. And she was telling

5:47

me about Neuroscience 101. And

5:49

I was curious about it and came back and

5:51

started googling like crazy. And I realized this little

5:53

model that I had discovered and the neuroscience perfectly

5:55

overlap. I hadn't discovered why marketing worked. I discovered

5:57

why people do what they do. So

6:00

I reached out to a famous neuroscientist named Peter

6:02

Weibrau, who was the head of the Semel Institute

6:04

at UCLA, which is the largest neuroscience institute in

6:06

the world. I don't know how I got ahold

6:08

of him, but I did. And

6:10

I basically said, I need you to look at this stuff.

6:12

If I'm going to say this is related to neuroscience, I need

6:14

this blessed. Yes. So I like went to his

6:16

house for a weekend, just basically

6:18

talked nonstop. And I came in

6:20

on Sunday morning and he was

6:22

like fidgety. And I'm like, what's the matter?

6:24

He goes, it doesn't match the

6:27

neuroscience. I'm like, what do you mean? He

6:29

goes, you need to switch what and how.

6:31

I'm like done. Yeah. They

6:33

became why, how, what? The definitions are always the same,

6:35

but to match the neuroscience of how brain work, that's

6:37

what it was. And then I started to realize that

6:40

this thing had a power. At a

6:42

later point, it saved me because I had lost

6:44

my passion for my own work and hit sort

6:46

of a really dark period. And I

6:48

realized that I knew what I did. I knew how I did it,

6:51

but I didn't know why. So these

6:53

things all sort of collided. Personal depression plus

6:55

my exploration here. And it all sort of

6:57

came together. I have at least a half

6:59

dozen friends right now that have landed

7:02

in what they thought was going to be their

7:04

dream job. It typically happens via an acquisition. It's

7:07

a tech entrepreneur. They get acquired by a big

7:09

company. They're now inside the belly of the beast

7:11

of something large. And they have a

7:13

couple of sayings. It's like vest in peace, where it's

7:15

just like, you're just vesting and kind of showing up

7:17

and quiet quitting, right? Which I'm sure you've heard about.

7:20

What's going wrong there? What's

7:22

happening? Why are they feeling

7:24

this way? You're asking

7:27

something that's something that happens

7:29

two or three steps prior. Okay. The number of

7:32

young idealistic

7:36

entrepreneurs who start businesses and

7:39

ethics matter to them and treating their people right matters

7:41

to them and culture matters to them. All the things

7:43

that I write and talk about matters to them. And

7:45

they build these beautiful businesses.

7:49

And then they sell them to the highest bidder,

7:52

not to the company that believes in their values

7:54

and wants to maintain the culture, the

7:56

highest bidder. And the company goes

8:00

to shit. They change

8:02

the ingredients of the product because they go

8:04

for something cheaper, et cetera, et

8:06

cetera, et cetera. You go down the line. And

8:09

these, they can rationalize it because they cashed out

8:11

big. They can rationalize that, no, we did it

8:13

right. And they didn't. That's to be

8:15

honest, they didn't. Why not take a little less money and

8:17

sell it to the right company who believes in the values

8:19

rather than just sell it to the highest bidder? And so

8:22

if they're stuck in a place where they don't

8:24

want to be there, well, that

8:26

was their choice. They chose

8:28

that partnership. That's like marrying somebody just because

8:30

they're pretty. And

8:33

then complaining that my marriage isn't working and we don't get

8:35

along, I'm like, I don't

8:37

have any marriage advice for you. It's

8:40

hard though too because you have stakeholders, right?

8:43

Well that is another thing. It's the

8:45

same trauma, which is so many entrepreneurs

8:47

who are looking for capital, they

8:50

take the biggest capital from

8:52

the most famous venture capitalist, but

8:54

less capital from the right venture

8:56

capitalist. So they chose

8:58

their own partners and then they're surprised by their partners are

9:00

applying massive amounts of pressure on them to make decisions that

9:03

they don't want to make. I

9:05

don't have a lot of sympathy. And we have

9:07

reached the point now where, and I can't remember

9:09

the statistic, it's overwhelming. It's something like 80% of

9:12

companies are venture capital and private

9:14

equity backed. And so we

9:16

used to mock the public markets that

9:18

the pressure exerted by Wall Street would

9:20

force CEOs to make decisions they knew were bad

9:22

for their companies. And we're now

9:25

at a point where private companies are basically

9:27

functioning like public companies where the external pressures

9:29

are so great that the number of young,

9:31

brilliant, fantastic, talented CEOs getting fired from their

9:33

own companies, I have a friend who just

9:36

got fired from her own company because she

9:38

didn't have control of it. And she couldn't

9:40

make decisions. They fired her because she was trying

9:43

to do the quote unquote right thing and follow

9:45

the vision. And they wanted to do the thing

9:47

that made it prettier to sell in a shorter

9:49

period. There's an element of like you made your

9:51

bed. And so there's even

9:53

a degree of, look, I'm not in

9:55

their position, but there's

9:57

even a degree of irresponsibility. You

10:00

made the choice to take the deal and

10:02

now you're dissatisfied with the deal. You have

10:04

sort of sellers remorse and so you're going

10:07

to quiet quit because you're pissed off. I'm

10:10

like, they didn't do anything wrong. You

10:12

took the deal. I think there's some soul

10:14

searching to be done in business writ large, which is who

10:17

we take money from and who we sell to. Because

10:19

I think a lot of good companies actually

10:21

don't survive the founders because of

10:24

who we sell them to. I can almost count it like

10:26

clockwork because I've seen so many of

10:28

these deals and I know what it is. It's

10:30

a three year vest. When you sell the company, they put

10:32

golden handcuffs on you for three years and you can almost

10:34

just mark the date. And then you

10:37

see a founder being like, I'm leaving. And it's

10:39

of course right at the three year anniversary. And

10:41

they're out. And then if they

10:43

were holding it together with any duct tape or

10:45

whatever else, everything seems to fall apart from there,

10:47

unfortunately. Good partnerships. You love

10:49

the partner. You love the buyer. And

10:52

they're offering you some sort of ability to expand

10:55

your vision that you couldn't do yourself, which is

10:57

why you took the deal. And

10:59

fundamentally, you come to an arrangement where even though

11:01

you have a boss now and you didn't have

11:03

one before, that there's a degree of independence you

11:05

have to build this brand which is what they

11:07

want as well. And though

11:09

it won't be perfect, no relationship is, you

11:13

fundamentally still love coming to work because you feel

11:15

like you're still advancing the greater good in building

11:17

this business. So those

11:19

are the partnerships we should be pursuing.

11:21

Yes. Yeah, that makes a ton of

11:23

sense. It's almost like fuel for the fire at that point.

11:26

You're joining forces with someone to help you expand and grow

11:28

a lot faster. What about individuals

11:30

that are, I see as

11:32

individual contributors to an organization. And

11:35

I see some of these resumes when I'm looking to

11:37

hire, say an engineer, and you see bouncing around. You

11:40

see bouncing around between different employment opportunities.

11:43

What advice do you give them? And how

11:45

do you help coach someone through finding

11:48

their why? Well, there's

11:50

a couple of different questions there. You and I,

11:52

when we were younger, even if we hated our

11:54

job, we would never dream of quitting

11:56

in less than one year. All 100%. You

11:59

couldn't. So bad. And we all knew that if you

12:01

did that, it would destroy your resume. Yes. It

12:04

would create a bad narrative about what kind of employee you

12:06

were. And I mean, it would have

12:08

to be pretty toxic for you to leave in under a

12:10

year, right? And so we held

12:12

our nose and we made it to a year. And

12:15

this predominantly younger generation, though it's not

12:17

exclusive, but predominantly younger generation is very

12:20

comfortable quitting quickly. And

12:22

sometimes for not good reasons. And I've seen it

12:24

happen, which is the young people who are so

12:27

confrontation avoidant, they'd rather quit than go through the

12:29

discomfort of asking for a raise, for example. For

12:31

every action, there's an equal opposite reaction. There's a

12:33

finite mindedness to it, which is how do I

12:35

solve the immediate problem in front of me without

12:38

considering the long-term impact of that decision? I'm

12:40

not for or against the decisions, I'm saying

12:42

consider the long-term impacts. And I've been

12:44

public about this and I've been criticized for it by young

12:46

people, which is flash

12:49

forward five or six years and

12:51

you've had seven jobs, right? And

12:54

whether you're bouncing because you think

12:56

they're all toxic, whether you're bouncing because you're just

12:58

dialing for dollars, whatever it is, in

13:00

five or six years, the new

13:02

employer is looking at you and you're a

13:04

certain age now, which means I expect a

13:07

certain level of maturity and accomplishment. You

13:10

haven't had it because you haven't gone through

13:12

the shit. You keep jumping shit.

13:14

So I don't even know that you're qualified

13:16

for the senior position you're applying for that

13:18

somebody else with seven years experience could apply

13:20

for, number one. And number two,

13:23

if I'm given two resumes, one with somebody

13:26

who's bouncing around and one who's like had two

13:28

jobs over seven years, I'll

13:30

take the one with two because I'm not gonna trust

13:32

that this person is gonna stick around after

13:35

I've trained them up and got them all in. We

13:37

have a few years before we start seeing the

13:39

repercussions, but the repercussions are coming. And

13:42

again, I'm not saying don't quit, I'm saying

13:45

just be cognizant that

13:47

there are implications and

13:50

maybe be a little slower. Do

13:52

you think the problem there is that they're

13:54

picking the wrong profession and wrong job from

13:56

the get go or they don't have the

13:58

grit to stick it out? during the

14:00

hard times. You mentioned this

14:03

confrontation of voident. Is it because they are

14:05

like, this makes me uncomfortable, I can't handle

14:07

it, I'm out? Or did I just pick

14:09

wrong right away? I know we're

14:11

generalizing, but- I mean, who knows? But this

14:13

idea of dream jobs is a funny thing,

14:16

right? Yeah. Ain't no such thing, number

14:18

one. Every job is imperfect,

14:20

like every relationship is imperfect. And

14:22

we live in a world that idealizes both

14:24

relationships and jobs. And so

14:27

when my relationship isn't

14:29

perfect and my partner doesn't do all the

14:31

perfect things and then I've been in that

14:33

relationship, and I'm doing the same thing, this job isn't

14:35

perfect and I have stress and they want me to

14:37

work late on a Thursday. There's a problem with pursuing

14:39

the dream job because it doesn't

14:42

exist. Now that's not to say we should

14:44

suffer either. I believe you should have joy

14:46

at work. I believe you should be fulfilled

14:48

by work. I believe that you should be inspired by the

14:50

company you work for, but you don't have to like every

14:52

day. You can love your

14:54

children, you don't have to like them every day. You

14:56

can love your job, you don't have to like it

14:58

every day. I think we confuse the two, that there

15:00

are days that I don't like my job and that's

15:03

the reason to quit. But fundamentally, are you working in

15:05

a place where you feel seen, heard and understood? Are

15:07

you working in a place that you feel like you're

15:09

growing as a human being, that you actually are a

15:11

better version of yourself because you work here? Are

15:13

they pushing you and challenging you to

15:15

take on more responsibility than maybe

15:17

you even think you're capable of? And

15:20

that's uncomfortable. And if you go back to

15:22

Steve Jobs, for example, I know we herald him,

15:24

but he was pretty remarkable. One

15:27

of the things that Jobs did is

15:29

it was uncomfortable working at Apple. And

15:32

it wasn't uncomfortable because he was mean,

15:34

although he wasn't the nicest person

15:37

in the world. It's because

15:39

he saw potential in people that they didn't necessarily

15:41

see in themselves. And he pushed and pushed and

15:43

pushed people. And people who didn't like being pushed,

15:45

they quit. But the people

15:48

who were okay being pushed, they

15:50

all said, I achieved more

15:52

at this company than I ever would

15:54

have imagined. And Johnny

15:56

Ive, this sort of middling designer,

15:59

Jobs sees something. something in him that maybe he does

16:01

or doesn't even see in himself. Yeah. And

16:03

he gets pushed and pushed and pushed and pushed and

16:06

becomes one of the greatest designers in modern history. I

16:09

had a really long conversation with Tony Fidell about this.

16:11

Oh, yeah. Working with jobs and like

16:13

the growth comes from the discomfort. The growth comes

16:15

from the discomfort. Yeah. I

16:17

mean, look, there's so many metaphors and analogies, you know, I love

16:20

the one about the lobster. I haven't heard

16:22

the lobster one. So lobsters, the

16:24

soft mass inside the shell is

16:27

what grows. That's the work. The shell itself

16:29

doesn't grow. It's

16:31

this hard thing that sort of

16:33

excretes out and hardens. And

16:35

as the lobster grows, it starts to get

16:38

very uncomfortable in its own shell because it's

16:40

now bigger. It's like wearing clothes that are

16:42

too small. And only when

16:44

it gets to that point does it then shed the shell

16:46

and build a new one. In other words,

16:49

you can't grow without being uncomfortable. Right.

16:51

Yeah, that's so good. And that's true.

16:53

I like to equate everything to personal

16:55

relationships because corporate relationships are relationships, right?

16:59

Yeah. Which is every fight

17:02

or uncomfortable situation I ever had with my girlfriend,

17:04

though I did not enjoy it, though

17:06

I wish we'd never had it, though sometimes I was

17:08

to blame, sometimes she was to blame, more often than

17:10

not we were both to blame. And

17:13

when I say that just a quick aside, you know, usually

17:15

in an argument, we start accusing each other of who started it.

17:18

The reality is, yes, absolutely somebody always started

17:20

it and the other person almost always poured

17:22

gasoline. Yes. So you both

17:24

have a culpability. It doesn't matter what started it.

17:26

You both made it worse. Right. Invariably,

17:29

every uncomfortable conversation or fight that we

17:31

ever had, though I hated

17:33

every moment of it and so did she, we ended

17:36

up stronger and closer because of it. Because

17:38

there were lessons that were learned. There

17:41

were triggers that were

17:43

realized. There was

17:45

language that was dissected. And

17:48

what we did was learn to fight not

17:50

against each other, but against the problem. And

17:54

I think it's the same at

17:56

work, right? Which is when

17:59

there's. pressure exerted, is it me

18:01

versus management? Or is it

18:03

management and me versus whatever we're trying

18:05

to accomplish? And good leaders know that

18:08

and good team members know that. It's

18:11

when it becomes adversarial, us

18:13

versus them. And by the

18:15

way, I blame leadership as much as I

18:17

blame employees. Team members will go

18:19

out for drinks and vent about work, which I'm by the way,

18:22

totally healthy. I don't know what I'm talking about with that. But

18:25

sometimes narratives and especially in virtual, in

18:27

distributed workforces where everybody's wherever they are,

18:29

the rumor mills can spin out of

18:31

control a lot quicker. And

18:33

we blame management for what they did

18:35

to us or whatever. But it

18:38

happens at leadership as well. The number of times I've sat

18:40

in leadership groups, including my own, where

18:43

we label someone dumb

18:45

or lazy or

18:47

inconsiderate or one foot out the door.

18:50

And we make jokes about, oh,

18:53

here we go again, or entitled or just go

18:56

down the list. And we label them, we create

18:58

a narrative about them and now we treat them

19:00

that way. And though

19:02

they may not know our narrative, they know

19:04

that they're being treated a certain way. And

19:06

so one of the things that

19:08

is imperative in any leadership team, which is when

19:11

one person finds themselves venting about somebody where

19:13

it's creating a narrative about another human being,

19:16

it's imperative that somebody else in the leadership team

19:19

interrupt that narrative and say,

19:21

they could be lazy. True. Definitely

19:24

a possibility. Or they're overwhelmed.

19:26

Or we haven't given them good instruction. Or

19:29

they're struggling at home. Yeah, I was going to

19:31

say, they're going through something we don't know about.

19:33

There's a list of things. And so we treat

19:35

them with empathy and maybe check in on them.

19:37

I expect leadership to go first because they should know

19:39

better, but whether it's in a group of team members

19:42

about each other, more about management,

19:45

management about team members. And again, I hold the

19:47

leaders to a higher level of accountability and if

19:49

they act appropriately, the team will act appropriately. But

19:51

we have to interrupt each other with these kinds

19:53

of narrative. Discomfort is

19:55

one of those things where it's

19:59

good to be... be transparent

20:01

about discomfort. And it starts again, leaders set

20:03

the tone. Because it's disarming. When you lie

20:06

high and fake, when you pretend that you

20:08

got it all figured out, people

20:10

will think you got it all figured out. And so they

20:12

will pile on more and push you

20:14

more and give you more and expect more

20:17

because you said everything's

20:19

good. And that's when it becomes overwhelming.

20:21

And that's when you start blaming management

20:24

for mistreating you. But

20:27

hold on. Whereas I'm a great

20:29

believer in just being totally transparent about discomfort. And

20:31

sometimes it's real and sometimes it's perceived. For

20:34

example, and I had it happen recently, one

20:36

of my team members, she's wonderful. We're

20:39

a distributed workforce so we don't get a lot of FaceTime. So

20:41

she's never had a lot of one-on-one time with me. I

20:44

see her corporate off-sites and stuff like that and I see her on

20:46

Zoom all the time. But she's never had one-on-one time with me. And

20:48

so we brought her out to LA to have

20:50

a one-day hackathon with me. She's

20:54

young. She's in her early mid-20s, a

20:57

junior employee. And she

21:01

came clean. She said, I just need

21:03

to tell you, I was really nervous about today. I

21:07

don't get us a lot of FaceTime with you and I

21:09

want to make sure I do right. And I got

21:11

really prepared but I'm really nervous. And

21:13

giving me that information was

21:16

magical because if she had come in all

21:18

like ego and everything, I would have ripped

21:20

her writing apart a lot

21:22

more aggressively because she's good. But

21:24

now I could just be like a little softer

21:26

or I'd say, you're doing great. I can just

21:29

reinforce because I know she's feeling a little intimidated

21:31

or fragile. So saying,

21:35

I'm really excited about this project. I'm really excited about this

21:37

new responsibility you've given me. I'm a little uncomfortable because I've

21:39

never had this amount of responsibility and I really don't want

21:41

to screw it up and I want to do right by

21:43

you and I do right by me and I don't want

21:45

to fail. And simply just saying

21:47

that means that a

21:49

good leader will be like, got it. I'm here.

21:52

You're good. And

21:54

you feel supported in that discomfort.

21:58

Uncomfortable isn't the problem. It's feeling

22:00

alone and uncomfortable, that's the problem. Yeah. All

22:04

right. If you watch this show or you've

22:06

seen me on the random show with Tim

22:08

Ferriss, you know I love to talk about

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23:39

right, just a quick plug for my newsletter.

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up for this over at kevinrose.com. Join

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115,000 other readers. kevinrose.com,

24:18

you'll find the little newsletter link there and

24:20

sign up today. A good

24:22

leader can see the signs. Virtual

24:24

makes it much more difficult. Yeah. The

24:27

distributed workforce makes it much easier to hide, lie

24:30

and fake. Body

24:32

language doesn't come across as easily. Yeah. It

24:36

doesn't really show up on a Zoom call. But

24:38

I think discomfort is one of those things that to learn

24:40

to be uncomfortable is probably the single greatest asset you could

24:42

ever ... You know this because nobody

24:44

who's ever achieved anything in the world did

24:48

it smoothly. We

24:50

all came close to

24:52

zero if not hitting zero first, all of us.

24:56

Lionel Richie talks about this. When he was younger,

24:59

he had crippling, debilitating

25:01

stage fright. Lionel

25:03

Richie. He

25:06

says there's two types of people in this world. Nobody

25:10

has the absence of fear. The

25:12

two types of people in the world are those who have fear and

25:14

they take a step back and there are those who have fear and

25:17

take the step forward. I always took the step

25:19

forward. Courage isn't

25:21

the absence of fear. It's being afraid and

25:24

leaning into it. To be

25:26

uncomfortable and step forward is perhaps the single greatest

25:28

thing you can ever learn. What you discover is

25:30

you're surrounded by people who want to help you.

25:32

Yes. Which

25:35

is the most amazing thing to discover. This is

25:37

one of my biggest mistakes. When I was in

25:39

my early 20s and I had my first startup,

25:41

I was pleasantly surprised in that it was my

25:43

first go. It was Digg and it was the

25:45

first social news app and it exploded to tens

25:47

of millions of users in six months. And

25:49

I was afraid. That's uncomfortable. Oh

25:52

my God. Here

25:54

I am in college dropout, moved to the Valley. I

25:56

was so intimidated by everyone around

25:59

me. The VCs. I was getting introduced to everyone

26:01

else. And I was scared to

26:03

raise my hand and say, I don't know

26:05

the answer to this. Because

26:07

everyone was looking to me as like someone

26:10

that had created something new and exciting. And it

26:12

wasn't until actually two years into the company where

26:14

it was really strange. It was a very small

26:17

period of time where Dick was bigger traffic wise

26:19

than Facebook. And so Mark came to my office

26:21

Zuckerberg, and he just

26:23

asked a thousand questions. And

26:26

he was really probing me on so many

26:28

different things and admitting so many things that

26:30

he just didn't know. And

26:32

I was like, wow, I need to

26:34

be more like this. Because

26:37

here I am operating in this silo,

26:40

afraid, ashamed, and it's not doing me

26:42

any good. I'm actually doing more harm to

26:45

my business. And once

26:47

you have that unlock and you realize

26:49

it's a massive strength to have vulnerability and to

26:52

raise your hand and say, I don't know the

26:54

answer to this. It's a huge,

26:56

huge unlock. What I don't know is the three

26:58

most important words that a young entrepreneur can ever

27:00

learn. It's your story, it's also my

27:02

story. I had a small business and

27:05

I was chief cook and bottle washer. And I started having

27:07

employees and I had to be in every meeting and I

27:09

had to make every decision. I thought I had to have

27:11

every answer. And if I didn't, I thought I had to

27:13

pretend that I did. And A,

27:16

the business doesn't do well with that model, but

27:18

B, it's crippling. Depression set

27:20

in. Oh, 100%. Because you feel

27:22

so alone in the hiding. And

27:25

it wasn't until I learned to say, I don't know, or

27:27

can you help me? Or learn

27:29

to accept help when it's offered. The amount of help

27:31

we're offered on a daily basis if you just count

27:33

it, it's tons. Say,

27:36

I'll take that. And

27:38

it is humiliating by the way. Like I have some

27:40

very successful friends and they ask me what I'm going

27:42

through and I'll just talk about the stuff that I'm

27:44

stuck with or don't know. And these are very successful

27:46

people that I wanna look good in front of. The

27:49

amazing thing is by being open to them, the amount

27:51

that they are there for me, that

27:54

day of humiliation was the greatest

27:57

investment I ever made. And I think

27:59

that's what you need to think of it. ways.

30:01

And the solution that I found was sitting right in front of me

30:03

the whole time, which is this thing that I called the golden circle.

30:05

And that's when I made the realization that I knew what I did.

30:07

I knew how I did it, but I didn't know why. And

30:09

that was the reason that I was stuck

30:11

because I had no sense of purpose,

30:14

cause or belief. And I became

30:16

obsessed with understanding my why. I learned

30:19

my why, but more important, I learned how to help

30:21

others find theirs. And I helped my friends find their

30:23

whys. Just because I want to, it's

30:25

like you see a great movie, you tell your friends

30:27

to go see it. No other reason, right? There's excitement.

30:30

And my friends, they quit their jobs and started their

30:32

own businesses, or they found renewed joy in the jobs

30:34

that they had to the

30:37

same levels that I was experiencing way

30:39

higher. And they asked me to talk

30:41

to their friends. And I would go to someone's apartment in New York

30:43

city and stand in the living room and talk about this thing called

30:45

the why and help people find their why for a hundred bucks on

30:47

the side. And my career took a

30:49

weird turn completely by accident. It's all organic.

30:52

But the point to the question was it

30:54

was one person who held space. We

30:57

forget that we are

30:59

social animals and our very ability

31:01

to survive requires the help

31:04

of other people. If you

31:06

fall asleep, you need someone to watch

31:08

for wild animals. We're just no good

31:10

by ourselves. We can't solve complex problems

31:12

by ourselves, but in groups who are

31:14

remarkable, human beings hunted woolly mammoths. No

31:17

other animal could take down a woolly mammoth, but

31:19

we frail, weak human beings. Good.

31:21

Because the asset that we have

31:23

that is our superpower

31:26

is our ability to cooperate. And

31:28

if you know that and you remember that, that no

31:30

human being can survive or thrive alone, that we are

31:32

fundamentally social animals, you have to learn to ask for

31:34

help and you have to learn to offer

31:37

it. And that's what I did. And

31:39

that's where I learned that lesson. One of the things that

31:41

you said that struck me is, and this is the mistake

31:43

I make with my wife a lot, I'll admit it publicly,

31:45

is that I go into problem solving mode. She's

31:48

got an issue and rather than just sit there and

31:50

hold space and have

31:52

some empathy for what she's going through

31:54

and how something lands on her. I'm

31:57

like, let's fix this. And I'm like throwing out

31:59

solutions. and all this and then that's

32:01

not always the best. Men

32:03

are particularly bad at it. Men are usually

32:06

in the solution, not exclusively, but tends to skew

32:08

that way. That's correct. That

32:10

is not a good idea. There's a great video on YouTube

32:12

called It's Not About the Nail. Everybody can

32:14

go look it up. It's the one that has a

32:17

bazillion views. It's many years old, but it basically sums

32:19

it up absolutely perfectly. And by

32:21

the way, you're the same. When you have

32:23

a problem and somebody says, well, why don't you do this?

32:25

You end up being defensive and fighting with them because you

32:27

don't actually want them to solve the problem. You just want

32:29

to feel safe in your stuckness. And

32:31

when somebody comes to you and says, I'm struggling,

32:33

just go tell me more. What else? By

32:36

the way, you know how to do this because you read all

32:38

the books to do it with your children. And

32:40

when you say, daddy, I'm afraid, that's okay. You can be

32:43

afraid, but daddy, this, and you're like, that's okay. You don't

32:45

try and fix their fear. You

32:47

hold space for their fear. When they're

32:49

nervous, you don't try and fix their nervousness. You don't have

32:51

to be nervous. Don't be nervous. We've learned

32:53

that that's a terrible thing to do with children. You

32:55

go, oh, I know it's scary. You

32:58

affirm the feelings. Well, why

33:00

did you stop doing that just because somebody's an adult? You

33:03

still have to affirm. It's a great

33:05

point. Honey, I'm nervous. Honey, I'm scared. Honey,

33:07

I'm confused. Honey, I'm angry. My

33:10

girlfriend and I were ... She said something

33:12

about something and I had

33:14

done something that upset her. And

33:17

I basically was like, well, that's ridiculous. I

33:19

mean, clearly, I didn't mean to. Can you say that I

33:21

did that? Of course I didn't do that on purpose. I'm

33:24

in full on defense mode. I'm in full on ... It's

33:27

not really gaslighting, but it's a form of gaslighting, which is like

33:29

I'm saying, you can't feel that

33:31

way about that. And

33:34

after many rounds, I finally

33:36

said, if I were in

33:39

your shoes, I would have felt the same. And

33:41

she said, thank you. And the funny thing

33:43

is what preceded that was, I just need you to see

33:45

it. What if you were me? Like

33:48

she literally gave me the instruction. I'm like, well, if I

33:50

were in your shoes, yeah, I probably would have felt the

33:52

same way you're feeling now. That was it. I've

33:54

been there. I've been in this

33:57

exact conversation where, yeah, 100%. because

36:00

I'd imagine you can't do that in two

36:02

minutes. You can. Tell

36:05

me. So finding the why is

36:07

the easy part. It's like college

36:09

graduation is called commencement. Yeah.

36:12

Beginning of something. Yeah. Well, finding your

36:14

why is easy. That's why I called the book Start With Why, because once you have

36:16

it, now the work begins. Right. So

36:19

again, there's two questions there. One is

36:21

how to find the why and which I'll tell you. And

36:24

the one is when you're coming up to a stranger, I

36:26

mean, they don't know me and I don't know them. And

36:29

they come in and say, can you help me get out of

36:31

this? Or, you know, my answer is always

36:33

the same is, you don't know

36:35

me. You know the image

36:37

of me. You know the image you've built of me. I

36:39

could be the worst qualified person to help you with this. Go

36:42

ask somebody who actually cares about you. You know, you're

36:44

not my friend. Like I

36:46

like you, you seem very nice, but why would I

36:49

get into mud with a stranger? I don't know you.

36:52

You know, go ask somebody who loves you. Because

36:54

it's safer to be vulnerable with me because

36:57

I'm a stranger. It's hard to be vulnerable

36:59

with somebody who actually knows us. But

37:02

that's the thing you gotta do. They're

37:04

asking the wrong person. I'm

37:07

sympathetic, but I'm the wrong person. So

37:09

where does a therapist fall on that? Because

37:12

you don't know them, but yet you can

37:14

be vulnerable around them. How

37:16

do they fit into your thinking? Like

37:19

obviously it's a useful tool to have

37:21

a therapist. Therapists have said that

37:23

I professionally hold space for you, that

37:25

is my job. Depending on the

37:28

therapist, some of them have tools to

37:30

help you with whatever you're dealing with. So they

37:32

can equip you with tools. And I think therapists are

37:34

one of the things that we need. I don't think they're the

37:36

only thing that we need. I believe in therapy,

37:38

I think is a good thing. And the practice

37:40

of being open with someone. But I hope that you

37:42

use that skillset with your friends. Like what's the point

37:44

of learning the skill if you're not gonna apply it

37:46

in other places? And I think somebody

37:49

who really struggles with vulnerability should do

37:51

therapy because it is a good way

37:53

to practice being vulnerable with the

37:56

people you really need to be vulnerable. If

37:58

you're only vulnerable with your therapist, no one else. out

46:00

in a boat. I was probably 10 years

46:02

old and I helped reel in like a

46:04

45 pound salmon.

46:07

I obviously couldn't do it myself. Actually, I take

46:10

that back. A better memory was laying in the

46:12

back of our truck bed, looking

46:14

up my dad, showing me satellites for the first

46:16

time. And I saw a satellite camping with my

46:18

dad. That was like just a magical moment. Okay.

46:21

Tell me more about that. I just

46:23

realized how much I love my father. And I just

46:25

realized how special it was that I got to spend

46:27

some one-on-one time with him and that he would take

46:29

time out of his busy schedule to

46:32

show me attention, to teach me things.

46:34

It was difficult because my dad was

46:36

a very verbally abusive father to my

46:38

mom. And so he was always angry.

46:40

And so to see him being tender

46:43

with me was just a beautiful thing

46:45

because I got to see my dad

46:47

in a place of like happiness,

46:50

which I didn't see that often. Yeah. And

46:54

what was it about showing you the satellites? More

46:56

one-on-one time. And I just didn't even know

46:58

those things existed. My

47:00

late 40s satellites were a big deal way back in

47:02

the day. And now I will go watch SpaceX launches

47:04

outside of my balcony. But back then it was like,

47:07

I just didn't even know you could see them with

47:09

the naked eye. And if you're laying on a clear

47:11

enough night, you could look up and you can actually

47:13

track them and see a satellite, which is amazing. Yeah.

47:16

Okay. So what's interesting about those stories,

47:19

seeing satellites with your dad, and when you

47:21

talk about the intermittent fasting, you

47:24

use very similar language in both of them, which

47:26

is you talk about the opportunity to have

47:28

these moments. My dad was an angry man

47:30

and I got to see him in tender

47:32

times. You talk about giving

47:35

somebody else the opportunity to spend more

47:37

time with. It's about the

47:39

discovery of beautiful things that you didn't know existed.

47:42

An angry man who could be tender, a satellite

47:44

you know you could see with the naked eye.

47:46

The discovery of changing an

47:48

intermittent fast, even the

47:50

uploading of things. It's really about

47:52

it's recognizing that there's community, like

47:55

there's other people who connect. And

47:58

I think your why sort of exists. in

48:00

this arena. I'm struggling

48:02

to find the exact words for it. Yes. That

48:04

feels right to me. It's very right to me.

48:07

Where the things that bring you joy are

48:09

when you give somebody the opportunity to make a

48:11

discovery that has a positive impact in their lives.

48:14

To see something they didn't see before. And in

48:16

all those examples, there was an element of like,

48:18

I didn't know that before. I

48:20

had never seen that before. I didn't know that could have

48:23

an impact. Right. And there was a positive impact, whether it's

48:25

spending time with your dad. And you

48:27

said it beautifully, which is giving somebody the opportunity

48:29

to spend more time with their mother father that

48:31

you didn't have. Yeah. And to

48:33

some degree, you're becoming the best parts of

48:35

your father, which is to take

48:38

quiet moments, show somebody something and let

48:40

them discover something magical. Yeah. I think that's why I

48:42

like playing with my kids so much. The

48:45

things you get to show your kids. Yeah. And

48:47

see through their eyes. See through their eyes. Yeah,

48:49

it's beautiful. It's beautiful. And even the way you

48:51

talk about social voting, which is to see through

48:54

other people's eyes what they

48:56

find interesting. So there's discovery for

48:58

the person who's learning it for the first time, but

49:00

there's discovery for you who's teaching them because you don't

49:02

know where it's going to go. Right. And

49:04

so there's discovery on both sides. Yeah. So I

49:06

think discover or discovery is sort of your magic

49:08

place, your magical place. Anyway, your why

49:10

exists somewhere in the middle. No, that's awesome. I do

49:12

want to talk about like what you do professionally for

49:14

people, because I think this is important. I noticed your

49:16

site has some ways that people

49:19

can sign up and actually learn how to be

49:21

coached through this. More people need

49:23

to do that. And I want to take it further now. What

49:26

do people do on your site? So we

49:28

started the optimism company with a very specific purpose,

49:30

which is to advance the idea of human skills.

49:32

You know, I hate the term soft

49:34

skills, hard skills and soft skills. First of all,

49:37

hard and soft are opposites. These things

49:39

do not work against each other. And also

49:41

there's nothing soft about soft skills. There are hard

49:43

skills and there's human skills. Hard skills are the

49:45

skills you need to learn to do the job

49:47

you need to do. And human skills are the

49:49

skills you need to learn to be a better

49:51

human being. And there's a great irony in being

49:53

human, right? Like cats don't have to work very

49:55

hard to be cats. They're just naturally good at

49:57

cats. But we have to actually do a lot

49:59

of work. lot of work to be good human

50:01

beings. It's frustrating and annoying. And we

50:04

built the optimism company to completely

50:06

focus on teaching people the human

50:08

skills they need to be better

50:10

human beings and to

50:12

advance that ability to cooperate and

50:14

socialize. Is that both personally and

50:16

professionally? It's you, right? So

50:19

when I teach you better listening skills, when I

50:21

teach you how to have a difficult conversation, when

50:23

I teach you how to have an effective confrontation,

50:26

right? Now, we teach it in a work context

50:28

because that's where the people are. But the reality

50:30

is those skills are useful everywhere. I like to

50:32

make the joke that there's an entire section of

50:34

the bookshop called self-help and there's no section of

50:37

the bookshop called help others. And

50:39

what we need is to advance the help others

50:41

industry. And that starts with teaching people the human

50:43

skills of how to not only be

50:45

a better version of yourself, but more important, which

50:48

is how to be a good partner, friend,

50:51

colleague, coworker, boyfriend, girlfriend, brother,

50:53

sister, son, daughter, mother, father

50:55

to somebody else. Because all

50:57

of these relationships, boss,

51:00

employee, dad, mom, brother,

51:03

sister, they're all cooperative.

51:05

None of them are solo. They all involve

51:07

in a relationship. Almost every label we have

51:10

for people involves some sort of relationship. You

51:12

can't be a leader if nobody's following you. You can't be

51:15

a follower if there's nothing to follow. All

51:17

of these things is a relationship. Even when people

51:19

talk about their faith, I'm a follower of X.

51:21

Well, that's a relationship. That's how they describe faith.

51:24

And so that's what the optimism is singularly focused

51:26

on, which is how we teach people the human skills

51:29

to be better human beings. That's awesome.

51:31

I was picking to the website and I noticed

51:33

there was a couple of things you

51:36

mentioned on the site that you teach

51:38

people the courage to lead and then

51:40

also conflict resolution. How do you teach

51:42

someone to resolve conflict? So

51:45

many of these skills, the foundational skill of

51:47

a lot of them is listening, right?

51:49

Like we talked about it before with you and your wife, you

51:52

fix everything. What you need to do is learn to listen. You

51:54

work really hard to learn to listen to

51:56

your kids, but then you abandon the skill

51:58

at work or... in your adult

52:01

relationships, right? And so conflict

52:03

resolution, we have conflict at work, we have

52:05

disagreements, we have misunderstandings, we feel triggered by

52:07

certain things that people say, whether they said

52:09

it on purpose or by accident, we

52:12

feel pressure, we react badly. There's

52:14

conflict everywhere. Right. And

52:17

I don't believe that world peace, for

52:19

example, is the absence of conflict. I

52:21

think that's nonsense, right? We live

52:24

in a world with no conflict or

52:26

war. Nope, not gonna happen, right? To

52:28

me, world peace is the ability

52:31

to resolve conflict peacefully. There's

52:33

gonna be conflict. How do you resolve it peacefully? And you

52:35

see it at work all the time. People yell at each

52:37

other, people quit out of anger, people fire out of anger.

52:41

Conflict is gonna happen. How do we resolve

52:43

our conflicts peacefully? You're gonna have conflict in

52:45

your relationships. How do you resolve conflict peacefully?

52:48

So for me, conflict resolution is that very

52:50

difficult skill of when you're

52:52

angry, you still have the skill to hold space

52:54

for somebody else. That's so hard because when someone

52:56

is triggered, everything goes out the

52:58

window. And it's just like all of a sudden it's

53:00

all about emotion. How do you train yourself to say,

53:03

let me pause this emotion and set it aside for

53:05

a second and listen? What's the process

53:07

like? Part of it is you have to have a game

53:09

plan going into every conflict. You wanna make these decisions before

53:11

you get to conflict. You don't wanna

53:13

be in conflict and then having to come up

53:16

with strategy. You need to master these skills before

53:18

the conflict so you're prepared. Whether they're athletes or

53:20

military, they talk about muscle memory. That you practice

53:22

and practice and practice and practice and practice. So

53:24

you don't quote unquote have to think in the

53:26

stressful time because you can just quote unquote rely

53:29

on your training. Interesting. So you offer

53:31

that type of training? Well, I mean, if you do these

53:33

kinds of trainings, then you're doing them in artificial

53:36

environments. Is it role playing?

53:38

What type of training is it? The role playing we expect people

53:40

to go do themselves. But the point is all of these things,

53:42

even if you learn the skill, you have to go practice it.

53:45

So I'll give you one example. My girlfriend. She's

53:47

a very, very open leader. When we're

53:50

not in conflict, that when we

53:52

fight, we don't want it to be me

53:54

versus you. We want it to be

53:56

us versus the problem. Right. So we

53:58

know that. So both of us have that mindset. So,

54:00

when conflict does arise, we both have

54:02

the right mindset. And sometimes it takes us a

54:05

little to get back to it. Or we

54:07

can say to each other, hey, hey, hey, I'm not

54:09

trying to be right here. I'm trying to solve this

54:11

problem. And they wouldn't mind to the person. But I'll

54:13

give you a real life example that actually happened, where

54:15

we went down that horrible rabbit hole of who started

54:17

it. If you hadn't done this, then

54:19

I wouldn't have done that. Well, if you hadn't done that, then I

54:21

wouldn't have done this. It sounds like some Middle East conflict, which is

54:23

like we're both blaming each other for where I had started. And

54:26

it was getting worse and worse and

54:28

worse and more aggressive. And

54:31

it occurred to me in that fight, this is going

54:33

nowhere. This is intractable. This is going to end up

54:35

on... This is just not you on the couch or

54:37

something. This is one of us is going to storm

54:40

out. If you just flash forward 10 minutes,

54:42

there's no peaceful resolution to

54:44

this journey we're on, where

54:47

we're pointing out what I did right and what she did wrong. And

54:49

she's pointing out what I did wrong and what she did right. And

54:53

I literally interrupted. I said, okay, this

54:56

is going nowhere. New rules. We're

54:58

going to reverse the script here because right now I'm putting out

55:00

everything I'm doing right and you're doing wrong and you're doing the

55:02

same. New rules. From now

55:04

on, I'm going to tell you what I did

55:07

wrong and what you did right. And

55:09

I'll go first. Wow. And I said, here's

55:11

what I did wrong and here's what you got

55:13

right. And she goes, well, yeah, here's

55:15

what I got wrong and here's what you got right.

55:17

That's beautiful. And I said, well, here's what I got

55:19

wrong and you got right. And in five minutes or

55:21

less, the tension had

55:23

been released. We realized

55:25

that both of us were trying. Neither

55:28

of us was evil. Both

55:31

of us were doing things right and both

55:33

of us had accountability. Yeah. And

55:35

in that moment, it just petered out. That's beautiful. You're

55:38

taking the knob and just turning it down enough to where

55:40

you can have a sensible conversation again.

55:42

But I created rules. Yes.

55:45

The rules of engagement are this. We're

55:47

going to continue to fight. But

55:49

we are operating from this script,

55:52

me right, you wrong. I'm just going to

55:54

flip the script, me wrong, you right. Yeah. And

55:56

let's just see what happens. Do you use that every time or

55:58

is that just advice? No, I didn't. That's amazing. I've

56:01

never done that before, but I'm going to do it

56:03

again. Yeah. But the point

56:05

is, is like doing it once even, the next

56:08

time you go down that path, I don't have to

56:10

go down the path and get it

56:12

really tense because I can stop it immediately and be like,

56:14

look, I hear what you're saying and

56:17

I definitely have some culpability here. Yeah. I

56:19

definitely did this wrong and you did this right. I can

56:21

do it immediately now. But the point

56:23

is these are skills. Right. Learnable, practiceable

56:26

skills and they're muscles. If you don't use them,

56:28

they're going to atrophy and this is what we're

56:30

trying to teach. We're trying to teach a

56:33

host of these skills that by

56:35

themselves, they'll help a little bit. But

56:38

the more of these skills we

56:40

master, the better colleagues, boyfriends, girlfriends,

56:42

brothers, sisters, fathers, mothers, sons, daughters,

56:45

leaders, employees, the better we become,

56:47

team members, colleagues, any

56:49

kind of human relationship. It was a

56:51

big blind spot for me for a long time, which is I was

56:54

a computer geek as a kid. But

56:56

back in our day, it was not cool to be a computer

56:59

geek because I always made fun of a lot. So

57:01

I was socially awkward and I had a really

57:03

hard time getting into my teens and then 20s,

57:06

going into a new situation without applying

57:08

alcohol because the alcohol for me was

57:11

like a crutch. Right. I've

57:13

since course corrected that, but I've had to

57:15

realize that when I stopped alcohol, I have

57:18

to build new muscles again. I have to

57:20

build new muscles around social interactions. One on

57:22

one, I'm fine. I can turn it on for a while and I'm fine.

57:25

But there's things that you have to kind

57:28

of figure out how to build that

57:30

muscle around so you can become proficient in

57:32

it. When you meet

57:36

someone that is like, I'm socially

57:38

awkward, I am not advancing my

57:40

career, the classic one is

57:43

afraid to ask for a raise, but let's

57:45

just say I'm not outgoing enough to inspire

57:47

confidence by the leaders in my

57:49

organization. Is that something that

57:51

you believe that we can learn and

57:53

improve upon? Social awkwardness is

57:55

not the problem. Discomfort

57:58

asking for difficult things is not the problem. Yes.

1:00:01

When you're just confident about who you are. It's

1:00:03

a point. And so all the things that we

1:00:05

talk about, we're trying to fix the symptoms,

1:00:07

but the cause is that you're just not owning

1:00:09

who you are. Right. And you can own

1:00:11

your strengths and you can own your awkwardness. Just

1:00:14

as an aside, I don't believe in strengths

1:00:16

and weaknesses. I believe we have characteristics and

1:00:18

attributes. And in the right

1:00:20

contexts, those things are strengths. And in the

1:00:23

wrong contexts, those things are weaknesses. So

1:00:25

nothing that we have in our personalities

1:00:27

is inherently a strength or a weakness.

1:00:29

It's all contextual. So

1:00:32

I work hard to be aware of

1:00:34

my characteristics and attributes. And I

1:00:36

work hard to learn when

1:00:39

those things are to my advantage and when those things

1:00:41

are to my disadvantage. And I work hard to put

1:00:43

myself in situations where who I am is more likely

1:00:45

to be an advantage than a disadvantage. So

1:00:48

for example, I'm disorganized,

1:00:51

chronically disorganized. And

1:00:53

I remember I was a young entrepreneur

1:00:56

at a networking event, socially

1:00:58

awkward, introvert, not very good at the

1:01:00

stuff. And I met

1:01:02

a guy who he's like, Simon, what you have to

1:01:04

say is amazing. I want to work with you. Here's

1:01:07

my card. Right? Amazing.

1:01:10

And if I was organized, I would be texting

1:01:12

him from the taxi on the way home or at least

1:01:15

emailing him the next day. Pleasure to meet

1:01:17

you. All of that stuff. Well, I lost the business

1:01:19

card. Yeah. I don't know what I did with it. Right?

1:01:22

I had it and I lost it. Two weeks later, I found

1:01:24

it at the bottom of a briefcase. And so I emailed him.

1:01:26

I don't know if you remember when you met a couple of

1:01:28

weeks ago, I just wanted to reach back out. And

1:01:31

he wanted to work with me more because he thought

1:01:33

I was busy. That's amazing. So is

1:01:35

being disorganized a strength or weakness? The answer is it depends.

1:01:38

Right. Right? In some contexts,

1:01:40

it is really not helpful. In some contexts, it's

1:01:42

an accidental strength, introverted and a

1:01:44

little bit quiet. And

1:01:47

intimidated by, like you don't know what to say in a room.

1:01:49

Strength or weakness. Well, at a

1:01:51

networking event, it's not going to help you. Right.

1:01:53

When you have to go around the room and do all that kind of

1:01:56

stuff. But if you're in a meeting and you're the quiet one, nobody knows

1:01:58

if you're an idiot or a genius. And

1:02:00

you're the listener. And they're

1:02:02

just waiting. So a huge strength. And

1:02:06

so all of the things that I know about me and

1:02:09

when I thrive and when

1:02:11

I fail, when I'm

1:02:13

happy and when I'm struggling, I

1:02:16

figure out what the characteristics and attributes

1:02:18

are and work very hard to put

1:02:20

myself in situations, find jobs, find clients,

1:02:22

find opportunities that are more likely to

1:02:24

result in me having those characteristics and

1:02:26

attributes work to my advantage versus

1:02:29

simply chasing the money, chasing the client,

1:02:31

chasing the opportunity, finding myself in

1:02:33

a situation where this is not going to work to my

1:02:35

advantage. Yeah. And do

1:02:38

you believe those characteristics and attributes can

1:02:40

be enhanced? Some people I know, they

1:02:42

just can't make a decision for the life of them. They can't move

1:02:44

forward. Is that something where you

1:02:46

look and say, well, that's kind of your

1:02:48

DNA that's an attribute or a characteristic, that's

1:02:50

who you are. Or we can actually take

1:02:52

who you are and enhance something to make

1:02:54

that a better, more smoother process for you.

1:02:57

I don't think that's necessarily a characteristic or

1:02:59

attribute. What's underlying that is

1:03:01

risk tolerance, accountability. Yeah. So

1:03:03

how do we improve risk tolerance? So risk

1:03:05

tolerance and accountability come from relationships, believe it

1:03:08

or not. So this is why

1:03:10

people say, the lawyers say we

1:03:12

can't do that. The lawyers

1:03:14

don't make the decision on this. You can

1:03:16

do. The lawyer said, I can't do

1:03:18

it. That's not a lawyer's job. And any lawyer who says

1:03:20

you can't do this is actually not doing the job. Lawyers

1:03:22

have one job, advise you on risk. There's a lot of

1:03:25

risk if you do that. And you're the one who's supposed

1:03:27

to assess the risk reward and decide if the risk is

1:03:29

worth it. And if it's not worth it,

1:03:31

then say no. But if you think it is worth

1:03:33

it, then say yes. Every time I hear a CEO

1:03:35

say that, it's such bullshit. And when anybody says the

1:03:37

lawyer said we can't, they're abdicating the responsibility of making

1:03:40

a decision. It's a weak leader. Yes,

1:03:42

take counsel from your attorneys. Absolutely.

1:03:45

But ultimately, you've got to take

1:03:47

a risk or not. It's your choice. If you want

1:03:49

to have a high or low risk tolerance, I don't

1:03:52

care. But ultimately, say, own up to it and say,

1:03:54

I listen to our lawyers and I agree

1:03:56

with them. This is too risky for our business. This is

1:03:58

too risky. So I made the call. I

1:04:00

made the call, they spooked me,

1:04:03

and I just don't think it's worth it.

1:04:05

It's palpable. And if it goes sideways, I

1:04:07

think we can deal with the fallout. That's

1:04:10

the conversation of which the lawyers are part of

1:04:12

it. So being decisive, I think, is

1:04:14

about relationships. When we have

1:04:16

relationships where somebody says to us,

1:04:19

I believe in your vision, you got this.

1:04:22

The world needs what you're trying to do. You

1:04:25

will find your courage to make decisions skyrockets. When

1:04:29

you don't seek relationships and support from

1:04:31

others, you will going to be alone

1:04:33

in all your decisions. And

1:04:35

that's where the fear

1:04:37

creeps in. Because

1:04:39

you feel like you're on an island. And

1:04:41

I think the more senior you get in an organization,

1:04:43

whether you're a young founder or whether you're a senior

1:04:45

in a large corporate organization, it's

1:04:48

a very lonely place. And

1:04:50

we all know it. We all talk about it. When

1:04:52

you're not in those situations, you don't understand it. But

1:04:54

when you're there, it is an incredibly lonely place. Because

1:04:57

there's not a lot of people you can confide

1:04:59

in. When you have moments of crippling

1:05:02

doubt, are we doing the right

1:05:04

thing here? That last decision

1:05:06

I made, then I just blow it. You can't go

1:05:08

to your team and say, I think

1:05:11

I've completely screwed this one up. You have to

1:05:13

be vulnerable and open with your team. You can't share

1:05:15

that. But you have to share it with someone. And

1:05:18

to be able to call a friend, I'd be like,

1:05:20

dude, I think I completely screwed this up. Yeah.

1:05:23

It's relationships. Human

1:05:26

beings need human beings. Done. And

1:05:28

the more human beings that you have in your life that love

1:05:30

you, care about you, trust you, and you love them, care about

1:05:32

them, and trust them, you will find

1:05:34

yourself with a courage and a confidence that few

1:05:37

others have. By the way, people who have that

1:05:39

confidence without relationships, that to me

1:05:41

is psychotic. Right. So if we want

1:05:43

to unpack that a little bit and say, okay, I'm in my

1:05:45

late 40s. Yeah, I just moved to LA six months ago. Building

1:05:49

a new network of trusted friendships,

1:05:51

relationships, it's harder to do as

1:05:53

you get older and couples

1:05:55

establish patterns. They have kids now. There's more

1:05:57

responsibilities. What if someone's listening is be like,

1:05:59

okay, great guys, you're telling me over and

1:06:01

over again, I need relationships, I get it.

1:06:03

I don't have a whole heck of a

1:06:05

lot. What do I do? So

1:06:08

I'm in the same place as you, you know, I'm a COVID

1:06:10

transplant. I have friends in LA and

1:06:12

some good friends in LA, but expanding my networks proved

1:06:14

to be very hard, partially because

1:06:16

LA doesn't have serendipity. I

1:06:18

come from New York where you bump into

1:06:20

people all over the place. Here I go from my couch

1:06:22

to my car to an office or

1:06:25

a conference room and then back, we're then

1:06:27

reverse back away and you never bump into,

1:06:29

there's no serendipity. And

1:06:31

so meeting people has to be

1:06:34

prescriptive and it's very hard. It's

1:06:36

very hard to meet people here. And you know, it's Hollywood,

1:06:38

so everybody's a little bit aloof. You know, you get people's

1:06:40

cell phones, but you're not allowed to use them. It's

1:06:43

a weird place. It is, yeah. So one

1:06:45

of the things I'm doing, and it's imperfect

1:06:47

what I'm doing, which is I'm leaning on

1:06:49

my friends from not from here, yeah, but

1:06:51

I'm calling them up more. That's what I'm

1:06:53

doing as well. Yeah, and you know, I'm

1:06:56

finding ways that we can meet up somewhere or can

1:06:58

you come out here or let me come out to

1:07:00

you or why don't we go away for a weekend

1:07:03

together? When I'm realizing that a

1:07:05

couple of days of precious time is better than

1:07:07

lots of fleeting moments. And I spend

1:07:09

a lot of time on the phone with my

1:07:11

friends who aren't here. So funny how the

1:07:13

phone's made a comeback. I do more phone

1:07:15

calls with friends remote now and I actually

1:07:17

wanna hear them than texting. It just feels

1:07:19

more intimate. Also, I don't like Zoom. I

1:07:21

don't think, well, sitting. I'm a

1:07:23

pacer. And so on a phone, I

1:07:26

can pace. Yeah. I go for a

1:07:28

ruck. I put on one of those weighted backpacks and just

1:07:30

go on some of these trails and just call a friend.

1:07:32

Chat for a half hour. We now live in a world

1:07:34

where, you know, it's considered rude to call without texting first.

1:07:37

I mean, really? Just don't answer the call then. Right.

1:07:40

I just call. Yeah. I just call. If they're that

1:07:42

close a friend, you should just be able to call. because

1:07:45

I just think the phone is a

1:07:47

beautiful, magical, to hear voice. One

1:07:49

more question for you. We started off the conversation

1:07:52

talking about great leaders. You mentioned Steve Jobs. One

1:07:54

of the people that I have been fortunate enough

1:07:56

to have on this show is Elon Musk a

1:07:58

while ago. Really admired him. you know, got

1:08:00

to watch his career unfold and him

1:08:03

build some great companies. Seems

1:08:05

like he's found his why. That

1:08:08

said, Twitter slash X was a

1:08:10

huge head scratcher for me. Do you think

1:08:12

he kind of lost his way? So let's

1:08:14

just take one step to

1:08:16

the left and say, why is Elon Musk

1:08:19

important? There

1:08:21

are plenty of very successful entrepreneurs who

1:08:25

their success, they won the

1:08:27

lottery. You know, like

1:08:29

right place, right time, right

1:08:31

partner. And some of the ones we admire weren't

1:08:33

the ones who came up with the idea, they're just the ones

1:08:35

who are leading the company. Then we'll

1:08:38

leave the names of those companies out, but you and I both know

1:08:40

who they are. And they won't be

1:08:42

able to repeat it. Even if they've

1:08:44

made hundreds of millions of dollars, they

1:08:46

won't be able to repeat it. Elon

1:08:49

is important because he's

1:08:51

repeated it multiple times. He's the real

1:08:53

deal. Real deal. Real

1:08:56

deal. Right? So that's important.

1:08:58

He didn't win a lottery. Absolutely. People

1:09:01

bet against him. And

1:09:03

he had so much passion and vision for what he was doing

1:09:05

that he proved all the naysayers wrong. He

1:09:08

made a very bad decision on Twitter. Right?

1:09:11

He got backed into a corner. He backed himself.

1:09:13

I don't think he wanted to buy it at the end. I don't

1:09:15

think so. I think he backed himself into a corner. Yeah. And

1:09:19

he tried to get out of the deal. Couldn't.

1:09:22

Just as a side, I think it's really funny. The board

1:09:24

members of Twitter and like leaders that were like, we would

1:09:26

never sell. How much? How's

1:09:29

that idealism doing for you guys? It turns

1:09:31

out everyone's got a price. Anyway,

1:09:33

I think Elon backed himself into

1:09:35

a corner. Because he's always beaten the naysayers

1:09:38

in the past, people are saying, well, never

1:09:40

doubt Elon. Right. Well,

1:09:42

no, you can doubt Elon. In this case, he doesn't

1:09:44

have a passion or a vision. Yes. Like

1:09:47

he did for the others. The others were his ideas. Others

1:09:49

were his ideas or I mean, Tesla wasn't his idea, but

1:09:51

he saw the potential. The decisions he

1:09:53

made were clearly to advance a greater good. And

1:09:55

he was willing to take tremendous financial risk to

1:09:57

do it. In this case, he's trying to make.

1:10:00

a company that doesn't make money make money as

1:10:03

opposed to advance some sort of greater good and

1:10:05

it's clearly he keeps talking about freedom

1:10:07

speech but that's not it. Yeah.

1:10:11

Yeah. I think he screwed the pooch. I

1:10:13

think he made a mistake and the sad part is because

1:10:16

I think he has a brand and his

1:10:19

brand is look at the shit I get right. I

1:10:21

think he's too intimidated,

1:10:23

shy, embarrassed to say I blew

1:10:26

it. Right? Yeah. I

1:10:28

was like, look, I made the biggest

1:10:30

mistake in my career. I got wrapped up

1:10:33

in the excitement of it all. I find myself

1:10:35

buying something I didn't want to buy. We've

1:10:37

all done it but when you're the world's richest man, it's just

1:10:40

a lot more expensive and at the end of the

1:10:42

day, I don't really want to do this.

1:10:44

It's not my passion and I'm willing

1:10:46

to sell Twitter to somebody who actually has a vision

1:10:48

for this thing. You know, I don't

1:10:50

want to lose my shirt on it but you'll get a good deal. Yeah.

1:10:53

And I need to unload this thing and I screwed the pooch. I

1:10:55

don't want to go back and focus my time energy on the things

1:10:57

that I actually love and care about. If

1:10:59

he just said that, we'd all be fine with it. Yeah.

1:11:02

We'd all be like, cool. Everyone would stand up and

1:11:05

applaud. Everyone would stand up and applaud. And what he's

1:11:07

doing, unfortunately, it's very the times,

1:11:09

which is deny, deny, deny, deny, deny.

1:11:12

Right? Nobody does anything wrong anymore. If

1:11:14

we look at all of his companies, you

1:11:17

can see there's an idealism and you can see they kind

1:11:19

of like fit a portfolio. Like they

1:11:21

kind of all belong in this fund. This

1:11:24

one doesn't. It doesn't. It's

1:11:26

a social product that I find that

1:11:28

it's a different beast. It's

1:11:30

not science. Guy with Asaf shouldn't be running

1:11:32

a social... Exactly. Look, it's so

1:11:34

fraught with irony. One of his things that he said at the beginning was,

1:11:37

I think it's irresponsible and bad

1:11:39

that one company should be

1:11:41

deciding what we say

1:11:44

or don't say. So I've replaced that

1:11:46

company with a person. Another one

1:11:48

person decides what we should be saying or

1:11:50

not. Yeah, I know. I mean, whatever. We

1:11:52

can talk about it. I

1:11:55

can't imagine the pressure he feels, more importantly, that

1:11:57

he puts on himself. It's got

1:11:59

to be some time. being. Give

1:12:01

the guy a little grace. He screwed up. We all

1:12:03

do. His was more expensive and more public than the

1:12:05

rest of ours. I'd much rather him working on neuroscience

1:12:08

related issues. I don't want him working on

1:12:10

this. Every moment or day that he

1:12:12

spends working on this, he's not

1:12:15

helping us find solutions to energy problems. He's

1:12:17

not helping us find solutions to

1:12:19

mental health problems. Which he's damn good at. I

1:12:22

want Elon to do the stuff that he's great

1:12:24

at and I don't want him to do Twitter.

1:12:26

Yeah, same. We're completely aligned. What's

1:12:28

next for you? You've got several successful bestselling

1:12:30

books that could just be your jam for

1:12:33

the rest of your life. I've

1:12:36

all but stopped doing in-person public

1:12:38

speaking. I do them occasionally, but

1:12:41

it's basically not

1:12:44

happening anymore. Because it doesn't

1:12:46

work like it used to. I

1:12:48

believe in impact. Impact is more

1:12:50

important to me than money. When I was

1:12:52

starting, I was proselytizing. I was preaching a

1:12:55

point of view in a way the world

1:12:57

worked. Most people in the room

1:12:59

had never heard of me or my ideas. I

1:13:01

came into preach and the delta of

1:13:04

how people felt when I came in, when people felt

1:13:06

when I came out. The lifestyle that I was living,

1:13:08

which was on the road all the

1:13:11

time, exhausting. The pain was worth it. I'm a

1:13:13

great ... People like, you should never quit. You

1:13:15

have to have grit. People like, well, you have

1:13:17

to know when to quit. My standard is very

1:13:19

simple, which is if

1:13:21

the struggle or the sacrifice is worth it,

1:13:23

then keep doing it. If the struggle or

1:13:25

sacrifice doesn't feel worth it, then stop doing

1:13:27

it. You know you have cause and you

1:13:29

know that you're doing the right thing when

1:13:32

this sucks, but it's worth it. I

1:13:36

hated it, but it was worth it. I hated the lifestyle. Now

1:13:40

the delta is much smaller. I'm

1:13:42

coming to talk about ideas

1:13:44

that people have already read about or

1:13:46

heard about. I'm no longer proselytizing

1:13:48

a group of people who've never heard of my work.

1:13:51

I'm in this magical period of exploration. I actually don't

1:13:53

know what I'm going to do now.

1:13:55

I'm saying yes to things that have no financial

1:13:57

gain whatsoever, but I'm just giving it

1:14:00

a try to see if I like it or not. I know that it

1:14:02

won't be what I've been doing. I like steep learning

1:14:04

curves. This is the curse of 10,000 hours. Gladwell

1:14:06

made this whole 10,000 hour things that

1:14:08

you have to achieve 10,000 hours or something before you

1:14:10

can achieve mastery. We all are

1:14:12

in, quote unquote, pursuit of the 10,000 hours.

1:14:14

But what we forget, and I firmly believe

1:14:16

that everything is balanced. Everything in the world

1:14:18

is balanced. Every advantage you have in the

1:14:20

world, there's a disadvantage that comes with whatever

1:14:22

that thing is always. The world is always

1:14:24

balanced and nature pours a vacuum. There's

1:14:27

a downside to the 10,000 hours. You talk

1:14:29

to lots of people who have mastered, you'll find the

1:14:31

same pattern as only one of a few things. Boredom

1:14:34

is one of them. It was so

1:14:36

exciting when the steep learning curve was steep.

1:14:38

I've met directors and producers and VCs and

1:14:40

entrepreneurs and they're so good at what they

1:14:42

do. They're considered the best in their industry

1:14:44

and they're out there. They know how to

1:14:46

make money. They know how to make movies.

1:14:48

They know how to write books. Whatever. Bang,

1:14:50

bang, bang. If you get them on

1:14:53

a quiet night when they're a little bit

1:14:55

tired, probably a glass of whiskey or two

1:14:57

in them, they will absolutely all admit that

1:14:59

they're bored out of their skulls because

1:15:02

there's nothing exciting about what they're doing anymore.

1:15:04

It's just rote. Because it's become

1:15:06

second nature to them? Because it's 10,000 hours.

1:15:08

They have so much mastery. It's not exciting.

1:15:10

It's the excitement of gaining 10,000 hours. It's

1:15:12

actually more enjoyable for the human being. I

1:15:14

meet these really, really senior successful people that

1:15:17

privately admit that they're bored. I wonder how Steph

1:15:19

Curry does it. I wonder how

1:15:21

those professional basketball players, when they're just the

1:15:23

top of their game, how they stay motivated.

1:15:25

Colby was really good at this. If you

1:15:27

saw The Last Dance, Michael Jordan created narratives

1:15:29

that were fake. That's right. He was

1:15:31

making shit up. He was making shit up. He was making

1:15:33

enemies. He

1:15:36

was not this great infinite minded guy that we all thought

1:15:38

he was. He was the consummate finite player. He was the

1:15:40

best finite player in the world where he would produce conflict

1:15:42

that didn't exist to make himself so angry that he was

1:15:44

going to f***ing take you down. That

1:15:48

was crazy. It was crazy insight. I do think

1:15:50

they get bored as well. I think it's just

1:15:52

like the next ring and become

1:15:54

the winning most this or the winning most team.

1:15:56

They just keep setting finite goals. That's

1:15:59

exciting for the show. short term, but do they have long term

1:16:01

joy? I don't know. You know, so

1:16:04

boredom is one thing that I think a lot of people when you

1:16:06

reach 10,000 hours, I think the

1:16:08

other thing is you find yourself like when

1:16:10

you're a hammer, every problem's a nail. And

1:16:13

when you have mastery of something, you see the whole

1:16:15

world through that one lens. And

1:16:17

I think it creates a closeness

1:16:19

to new. And you see

1:16:21

this a lot. You see very successful CEOs,

1:16:24

entrepreneurs that miss significant

1:16:27

changes in technology, for example. And

1:16:29

you see CEOs who didn't see the internet as

1:16:31

a thing. Right. I mean, you know.

1:16:34

Yeah, you can go back and look at those old quotes

1:16:36

and they're hilarious. Hilarious. Or like a bomber who like shit

1:16:38

all over the iPhone, like it'll never be a thing because

1:16:40

no one's gonna spend that amount of money on a phone.

1:16:42

You're smarter than that. But the problem

1:16:44

is, it's not because he's dumb. Yeah. And

1:16:46

it's not because he's blind. It's not because he's

1:16:49

stupid. It's because when you have

1:16:51

mastered something and you've been doing that thing

1:16:53

the same way for 30 years, to the

1:16:55

point where it's made you rich and famous

1:16:57

and the top of the organization, it is

1:16:59

very, very hard to see the world through

1:17:01

any other lens than that lens. And

1:17:04

whether you know it or not, you've created a

1:17:06

walled garden for yourself. When I was at Google,

1:17:08

the first thing I did when I landed inside

1:17:10

and I was assigned to their social products team

1:17:13

and I was running mobile for Google+, which ended

1:17:15

up failing. Well done. I

1:17:18

bounced. I was speaking of leaving jobs

1:17:20

quickly. I was there for like

1:17:22

four months and I went to Google Ventures and

1:17:24

just became an investor. I knew there was no

1:17:26

future there. But yeah, that was

1:17:28

horrible. But one of the things I realized is I'd

1:17:30

go into these product meetings and there was like 30

1:17:32

people in the room and I'd start talking about

1:17:34

what we were doing that was novel

1:17:37

and different and that just wasn't feature parity

1:17:39

with Facebook. And it

1:17:41

was like they were so of

1:17:44

the mindset of like, we're Google, we

1:17:46

can do anything, we have scale. They

1:17:49

didn't even use anyone else's tools. They were

1:17:52

never installing other apps of other competitors. They

1:17:54

weren't playing. They lost all of that. They

1:17:56

had their free lunches. They had their soccer

1:17:58

campuses. They even had a half-pipe. on Google's

1:18:00

campus, which I wrote, which was actually pretty

1:18:02

awesome. But it was

1:18:04

like, you're so surrounded by

1:18:06

like-minded people, you don't

1:18:09

think to play. And there's no discovery. Yeah.

1:18:11

And so I think that's what happened with Bomer and others

1:18:13

when you don't get a chance to actually get out there

1:18:15

and be a real person. That's the thing that made you

1:18:17

successful in the first place was the open-mindedness of the child

1:18:19

like one play. Yeah. You're 100% right. And this is the

1:18:21

curse of the 10,000 hours. It's 10,000 hours, plus, plus,

1:18:25

plus, which is why publishing

1:18:27

didn't invent the e-reader. Amazon invented

1:18:30

the e-reader, not publisher. Right.

1:18:32

Very confused. Right. Why is it that

1:18:34

Netflix made streaming a thing and not

1:18:36

the movie and TV industry? Right. How

1:18:39

did you guys miss that? You

1:18:41

could have, but you didn't. You

1:18:43

can't blame companies or industries because companies and

1:18:45

industries don't make decisions. Yeah. It's human beings

1:18:48

who have achieved mastery, who are now

1:18:50

running organizations, who are decision-making positions,

1:18:53

who literally cannot perceive the world

1:18:55

outside of the 10,000 hours

1:18:57

of mastery that they've achieved. For sure.

1:18:59

And I'm at that point where

1:19:02

I have 10,000 hours of mastery in one little

1:19:04

space and scares the shit out of me. And

1:19:06

so if there's one thing I know, which

1:19:09

is to go be an idiot again. I

1:19:11

love that. I need to start with four hours. Okay. I'm

1:19:13

going to learn about venture. I don't

1:19:15

know and understand anything about money. Right?

1:19:18

I've never been motivated. I'm a money idiot. And I'm sitting

1:19:20

at these meetings and they're all using all this jargon and

1:19:23

I am so clueless. It is not fun.

1:19:26

It is not comfortable. I feel dumb. Everybody

1:19:28

thinks I'm smart because I've achieved something. They

1:19:30

think I know everything about everything. Right?

1:19:33

And I'm trying to be dumb

1:19:35

and I'm trying to find what I'm passionate about that

1:19:38

is worth really working

1:19:40

hard to not be dumb with

1:19:42

the thing that I'm dumb about. What's your point earlier?

1:19:44

I mean, it's about asking questions that you don't know

1:19:46

the answer to again. You'll appreciate this. So I got

1:19:48

to know James Kars, who was

1:19:51

the originator of the concept of

1:19:53

finite and infinite games before he

1:19:55

died. And when I first

1:19:57

met him, of course, the burning question. How'd

1:20:00

you come up with that? Right now, just as an

1:20:02

aside for those who don't know what I'm talking about. So

1:20:05

Jim Carse was a philosopher and theologian. He

1:20:07

worked at NYU who wrote a book in

1:20:09

the mid 1980s called Finite and Infinite Games,

1:20:11

where he defined these two types of games.

1:20:13

It's a kooky little philosophy book, right? He

1:20:16

defined these two types of games. A finite

1:20:18

game is defined as known players, fixed rules

1:20:20

agreed upon objectives, football, baseball. If

1:20:23

there's a winner necessarily, you have to have a loser or losers.

1:20:25

But more important, there's always a beginning, a middle,

1:20:28

and an end. And you have

1:20:30

infinite games. Infinite games are defined as

1:20:32

known and unknown players, which means you don't necessarily know

1:20:34

who all the other players are, and new players can

1:20:36

join the game at any time. The

1:20:38

rules are changeable, which means every player can play

1:20:40

however they want. And there's

1:20:42

no such thing as winning. You can only perpetuate

1:20:45

the game. The goal is to stay in the

1:20:47

game as long as possible. So life, basically. Business.

1:20:49

Nobody wins business. When Circuit City

1:20:52

went bankrupt, Best Buy didn't win anything. The game

1:20:54

will change forms. You don't know who your competitors

1:20:56

are necessarily. New competitors can join. Every company can

1:20:58

run however they want to run, and

1:21:00

no one's ever declared the winner of business. This

1:21:02

is what Kars put out in the world. And it

1:21:05

dramatically impacted my work, because

1:21:07

I bought into his philosophy, H being

1:21:13

the best, or beating their competition. Based on what?

1:21:16

Right. Based on what agreed upon metrics, objectives,

1:21:18

and timeframes. So when you play to win

1:21:20

in a game that has no finish line, turns out you

1:21:22

make a lot of stupid decisions, and you

1:21:25

end up destroying trust, cooperation, and innovation. And

1:21:27

if you look at most companies today, most

1:21:30

large companies are not innovative. They just buy

1:21:32

smaller, more innovative companies. The average

1:21:35

lifespan of a company, I think, is 17

1:21:37

years, which is abysmal. Look

1:21:40

at the damage that companies are doing because they're

1:21:42

so short-termist. It's all because they have a finite

1:21:44

mindset in the infinite game of business. What Kars

1:21:46

articulated was a truth. A lot of people

1:21:48

have theories. Finite name games is

1:21:50

a truth. That is how the world works. You have to

1:21:52

play for the game you're in. So

1:21:54

I got to know him some. And of course, when I met him

1:21:57

the first time, I sat down with him and was like, I got

1:21:59

to ask. How did you come up

1:22:01

with this and he was telling me that

1:22:03

in the 1970s there were all of these salons

1:22:06

so that these intellectual salons of which he

1:22:08

was a part of where they would bring

1:22:10

in people from different disciplines like Mathematics and

1:22:13

philosophy and engineering to debate the

1:22:15

topic of the day, which was game theory game

1:22:17

through was all the rage in the 1970s and

1:22:19

lots of theories were coming out of these salons,

1:22:22

right? So for example, the prisoners dilemma which many

1:22:24

of us are familiar with that came out of

1:22:26

one of these 1970s

1:22:28

right so he was in these salons and

1:22:32

It occurred to him that in all of these discussions

1:22:35

They were always talking about winning and losing all

1:22:37

of them. Nobody was talking about playing. Hmm

1:22:40

even the prisoners dilemmas about winning and losing and Then

1:22:43

he sort of like went home with this problem. He had

1:22:45

stuck in his mind and he watched his kids and

1:22:48

he saw when his kids Played ping-pong there

1:22:51

was always screaming and yelling there was always fighting and

1:22:53

there's always accusations of somebody cheating Every

1:22:55

time it doesn't change with adults by the way, right? But

1:22:57

yeah, but when his kids were like

1:22:59

playing Lego, yeah They would sit there

1:23:01

quietly for hours. Hmm and One

1:23:04

of the kids would leave for a little bit and then come

1:23:06

back later and the game would the Legos would last

1:23:08

for days Yeah, and they would start and stop

1:23:10

and start to stop and there was never any

1:23:12

fighting and there's only cooperation Mmm, and

1:23:15

he realized that we're so obsessed with winning and

1:23:17

losing that we forgotten the value of playing and

1:23:19

not all games have

1:23:22

an end and Business

1:23:24

should be treated like a game rather than

1:23:26

a competition. It should be treated like Lego

1:23:30

More than baseball. Yes, and we overuse

1:23:32

sports and war analogies in business all

1:23:34

the time Yeah, we treat it like

1:23:37

a game. Yeah, we have launches. We

1:23:39

have campaigns Yeah, we have

1:23:41

wins. We have losses we give bonuses for

1:23:43

accomplishment. We talk about performance driven, but we

1:23:45

never talk about creativity Yeah, we never talk

1:23:48

about joy. We never talk about cooperation

1:23:51

or cross-pollination And

1:23:53

this is the magic of great innovation and

1:23:56

great businesses. Hmm. And so you talk about

1:23:58

the magic of play. Yes, right? One

1:24:00

of the problems with 10,000 hours of mastery, or

1:24:03

any kind of mastery, is you've become so good at something,

1:24:06

now you want to win every time you're

1:24:08

playing because you're the expert. And

1:24:11

there's a joy in not worrying

1:24:13

about the outcome. There's

1:24:15

a joy in just playing. And

1:24:18

so I am looking for few opportunities

1:24:20

to play baseball

1:24:23

and more opportunities to do Lego. That's

1:24:25

interesting. A few years ago I picked up studying

1:24:27

Zen with a great Zen master

1:24:30

out of Santa Fe. And one of the things

1:24:32

about Zen is it is a dedicated practice. You

1:24:34

want to get in your reps in terms of

1:24:36

hours, but you cannot have

1:24:38

an outcome because that pushes away

1:24:40

the wrong way. It defeats

1:24:42

the point. It defeats the point. The West is

1:24:45

more obsessed with finite and I think Eastern philosophies

1:24:47

are more obsessed with infinite. I learned that you

1:24:49

are actually not present until somebody

1:24:51

else says you are. Because

1:24:54

you can't be present by yourself. I mean you can,

1:24:56

that's one of the side effects. But the true value

1:24:58

of being present is as a gift to another. So

1:25:01

let's think about meditation. For those who have ever practiced

1:25:03

meditation, what you're supposed to do is sit

1:25:05

still and focus on one thing. Whether

1:25:08

it's something you stare at, whether it's a

1:25:10

mantra or a sound or the ocean, whatever

1:25:13

it is, you're supposed to focus on

1:25:15

one thing. You can't clear your mind,

1:25:17

that doesn't exist. You focus on one thing. And

1:25:19

you learn to clear your mind of all other thoughts except

1:25:22

this one thing. And if you have a thought about work,

1:25:25

you label it a thought, you say, ah, that's a thought,

1:25:27

I'm going to push that aside and I'm going to deal

1:25:29

with that later. And you find this tremendous calm and focus

1:25:31

and tremendous relaxation. Okay, what was the point of all

1:25:34

of that? Just so you can feel good? No. That's

1:25:37

the unintended byproduct that you feel good and you have all

1:25:39

the health benefits. The true benefit for

1:25:41

me of practicing meditation is that when I'm sitting with

1:25:43

a friend, they want to tell me something amazing that's

1:25:45

happening in their life or they want to tell me

1:25:47

something that's horrible that they're dealing with. I'm

1:25:50

focused on one thing and one thing only. They're telling

1:25:52

me every other thought, the car

1:25:54

that just screeched, don't hear it anymore. I

1:25:56

have thoughts of things I want to say and I label them

1:25:59

thoughts and I say, that's a I'm going to deal with that

1:26:01

later. You're bringing it to real life. I'm bringing it to real

1:26:03

life. And at the end of the conversation,

1:26:05

I know that I have been present, that all of

1:26:07

that practice, we call meditation a practice, that all of

1:26:09

that practice was worth it for this one moment when

1:26:11

my friend says to me, thank you for listening, or

1:26:13

thank you for being present, or I really feel heard,

1:26:16

thank you. Now all of

1:26:18

that meditation was worth it. And all of the

1:26:20

benefits that I derive are secondary. The true benefit

1:26:23

is the gift that I get to give when

1:26:25

working really hard in my own practice. So

1:26:28

we've made so many of

1:26:30

these Eastern practices that are

1:26:32

pro-social selfish. We

1:26:34

made them check boxes. We made them check boxes and we made

1:26:36

them only for us. And

1:26:39

perpetuating that imbalance that America is

1:26:41

so good at, which is we've

1:26:43

over-indexed on rugged individualism, Marlboro Man,

1:26:45

with heroized CEOs as if they

1:26:47

did everything by themselves. We're

1:26:50

all striving to be the hero. We're all striving

1:26:52

to be influencers. We've created heroes out of individuals

1:26:54

of which none of us succeed without groups of

1:26:56

people who believed in us, took bets on us,

1:26:58

were there for us, let us cry on their

1:27:01

shoulders, or just cheered us on

1:27:03

on a rainy day. We've forgotten that the

1:27:05

more we can focus on each

1:27:07

other and taking care of each other and

1:27:10

what it means to be a good friend, to be a good

1:27:12

partner, to be a good leader, to be a good follower, to

1:27:14

be a good employee, to be a good boss, to be a

1:27:16

good all the related friend,

1:27:18

that's where true joy and success

1:27:20

lies. And play, play,

1:27:24

I think is the most magical

1:27:26

of all, play without a

1:27:28

required income. You

1:27:30

start drawing, you start playing with Lego,

1:27:32

and a few days later, you decide

1:27:35

to put it away. Yeah. Arbitrary.

1:27:38

Yeah. And I'm trying to do that with

1:27:40

my career. I'm trying to play again. That's great. I love to hear

1:27:43

that. Must feel good. Well, it's nerve

1:27:45

wracking. You know, we talked about being

1:27:47

uncomfortable. I'm uncomfortable. I have no idea what my future

1:27:49

is going to be, but I'm

1:27:51

okay with that. That's awesome. What

1:27:53

you did with me was beautiful. Thank you again for

1:27:55

that. That was like just a fun little few

1:27:58

minutes of unpacking that. What's it

1:28:00

say? I wanted to go deeper on that. Where

1:28:02

do I go on your website? Wait, is there a

1:28:04

specific course? There's a whole thing about finding your why.

1:28:06

Okay, so that's the one to sign up for. That's

1:28:08

the one to sign up for. Okay, awesome. Simon,

1:28:11

thank you so much. This has been great. Oh,

1:28:13

my pleasure. Thanks for having me. Yeah, enjoy,

1:28:15

thanks.