0:00

Everyone in this world has an

0:02

opportunity to be the very best

0:04

at a certain thing that's matchable

0:06

to who they are as a

0:08

unique individual. What I've learned is

0:10

that a lot of people try

0:12

to say compete by being the

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best. Not the same thing. What

0:16

is the intersection of what you're

0:18

passionate about, what you're good at,

0:20

what you can get paid for.

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If you do that well, you're

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impossible to compete with. You won't

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Visit insiteglobal.com/learning

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leader. That's

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insiteglobal.com/ learning leader

1:18

to learn more. Welcome to

1:21

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1:23

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1:25

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1:27

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1:53

to 66866 now on to tonight's

1:55

featured leader. I loved this conversation.

1:57

with Mike Maples Jr. He's a

1:59

co-founding partner at Floodgate. He has

2:01

been on the Forbes Midas list

2:03

eight times in the last decade

2:05

and was recently profiled by Harvard

2:07

Business School for his lifetime contributions

2:09

to entrepreneurship. Some of his early

2:11

investments include Twitter, Demand Force, Twitch,

2:13

and applied intuition among others. Mike

2:15

is also the best-selling author of

2:18

Pattern Breakers, why some startups changed.

2:20

the future during our conversation we

2:22

discussed. The many lessons that Mike

2:24

learned from his dad who just

2:26

passed away seven days ago. I

2:28

especially enjoyed when Mike shared the

2:30

deeper meaning behind the phrase, do

2:32

your best. Then we discussed how

2:34

to manage that voice in our

2:36

mind that says we aren't good

2:38

enough or aren't capable of achieving

2:40

that massive goal. Then Mike shares

2:43

why he invested in Twitter and

2:45

also why he missed and didn't

2:47

invest in Airbnb. And then later

2:49

in the conversation I loved his

2:51

favorite verb noticing and how we

2:53

all can become better notishers of

2:55

the world and why that will

2:57

help us. as leaders. Ladies and

2:59

gentlemen you're in for a treat.

3:01

Please enjoy my conversation with Mike

3:03

Maples Jr. So to start I

3:05

know this is very fresh and

3:08

new and your dad passed away

3:10

a week ago but I loved

3:12

loved reading the kind words you

3:14

had to say about him as

3:16

well as others that poured in

3:18

online and you started by saying

3:20

he was a mentor a friend

3:22

in one of the greatest inspirations

3:24

of my life. I would just

3:26

love Mike to hear more. about

3:28

the impact and maybe even a

3:30

story or two about your dad

3:33

and how he influenced you so

3:35

much. Oh man, there are so

3:37

many and it's a little bit,

3:39

it's a little bit fresh right

3:41

now, right? He passed away a

3:43

week ago almost exactly. There were

3:45

a few things about him that

3:47

were really remarkable. This is the

3:49

meta lesson I learned and then

3:51

I could tell a kind of

3:53

a fun story or two. But.

3:55

He used to say, do your

3:58

best. And most people, when they

4:00

say that, they mean it in

4:02

a platitude sort of way, but

4:04

he meant it in a very

4:06

deep way. So what he understood

4:08

was that there's only one you,

4:10

and you don't know how much

4:12

time you're going to have in

4:14

this life. You might have a

4:16

short life, you might have a

4:18

long life, but you've got to

4:20

decide what you want to do

4:23

with the gift of your time.

4:25

And the best way to honor

4:27

the gift of your time is

4:29

to be the best version of

4:31

you that you that you that

4:33

you can be. You know, so

4:35

there are a lot of people

4:37

that I admire in business. I

4:39

admire Elon Musk, I admire, you

4:41

know, Mike Moritz at Sequoia Capital.

4:43

There's a lot of people that

4:45

are really smart, talented people, but

4:48

I shouldn't try to be like

4:50

them because they already have a

4:52

monopoly on being who they are.

4:54

And so I can't do better

4:56

than my best. That's all I

4:58

can do. But the thing that's

5:00

inspiring about it to me is

5:02

that everybody. has a unique strand

5:04

of DNA, no two people who've

5:06

ever existed in the history of

5:08

humanity are exactly alike. And so

5:10

what that means is that everyone

5:13

in this world has a comparative

5:15

advantage, that everyone in this world

5:17

has an opportunity to be the

5:19

very best at a certain thing

5:21

that's matchable to who they are

5:23

as a unique individual. And so

5:25

like what I've what I've learned

5:27

is that a lot of people

5:29

try to say compete by being

5:31

the best. Not the same thing.

5:33

Right? It's kind of understanding, you

5:35

know, what is the intersection of

5:38

what you're passionate about, what you're

5:40

good at, what you can get

5:42

paid for. And if you do

5:44

that well, you're impossible to compete

5:46

with. You won't be the best.

5:48

You'll be the only. And so

5:50

that was the main lesson I

5:52

learned from them. But it wasn't

5:54

just about doing your best from

5:56

an achievement point of view. Doing

5:58

your best is about gratitude. It's

6:00

about expressing the gratitude for the

6:03

time that you're given. It's about

6:05

honoring the gift of your time

6:07

Yeah, so so that was a

6:09

there's a lot of things I

6:11

learned from him, but that's the

6:13

high-order bit That you know the

6:15

other thing that I learned from

6:17

him was that just the power

6:19

of focus so like one time

6:21

I was like five years old

6:23

and I'm in this fishing competition

6:25

in Oklahoma in Oklahoma City. And

6:28

I was just above the age

6:30

that you're allowed to even be

6:32

in this thing. And there were

6:34

all these other competitors. You could

6:36

be up to 16 years old.

6:38

So I'm sitting there and it's

6:40

this hot lake in the summer

6:42

of Oklahoma. And my dad says

6:44

to me, I think that you'd

6:46

be smart to pick one spot

6:48

and stay there the whole time.

6:50

So how do you think we

6:53

should pick a spot? Do you

6:55

think we should pick a deep

6:57

part of the lake or shallow

6:59

part of the lake? Do you

7:01

think we should pick a part

7:03

of the lake that's shaded or

7:05

that's, you know, exposed to the

7:07

sun? Do you think we should,

7:09

you know, he starts asking me

7:11

all these questions like Socratic method.

7:13

And so we go to this

7:16

part of the lake and cast

7:18

the line and he goes, you

7:20

know, you may not win. There's

7:22

a lot of people in this

7:24

contest. And, you know, there are

7:26

all these 16 16 year old

7:28

kids running around in their overalls,

7:30

you know, you know, you know,

7:32

different parts of the lake. but

7:34

we stayed in one spot the

7:36

whole time and I end up

7:38

catching this carp and I end

7:41

up winning this competition and I'm

7:43

like five or six years old.

7:45

I can barely hold the trophy.

7:47

It's almost as big as I

7:49

am. And you know, it was

7:51

such a great lesson in the

7:53

power of focus and sort of

7:55

playing your game. You know, everybody

7:57

else would like cast their line

7:59

and they don't catch a fish

8:01

in 15 minutes. They're off to

8:03

the next spot. Everybody's running around

8:06

all across the lake scurrying about

8:08

hardly even keeping their bait in

8:10

the water most of the time.

8:12

And my dad was just like,

8:14

hey, you know, usually you win

8:16

by just being prepared and focused

8:18

and disciplined. And so that was

8:20

a just a classic example of

8:22

how he would teach you things.

8:24

And he wasn't he wasn't saying,

8:26

here's the lesson I'm trying to

8:28

impart. It was just more like

8:31

just the way he would interact

8:33

with you. He would just ask

8:35

you questions and try to get

8:37

you to think about what you

8:39

were doing. So he was really

8:41

good about that. And I think

8:43

this is part of why he

8:45

was so successful at Microsoft. So,

8:47

you know, my dad ended up,

8:49

Bill Gates invited him to join

8:51

Microsoft and run products for... Hey,

8:53

I heard that Bill Gates begged,

8:56

begged your dad to be the

8:58

adult in the room at Microsoft.

9:00

But, you know, like, my dad

9:02

gets to Microsoft. And you got

9:04

all these really smart young people

9:06

who've been to MIT and Stanford

9:08

and the top schools and they

9:10

knew tons and it was a

9:12

culture where, you know, you want

9:14

to be the smartest person. And

9:16

my dad was sort of like,

9:18

hey, look, all I care about

9:21

is that I know that you're

9:23

thinking about what you're doing. And

9:25

so if you're going to ship

9:27

Microsoft Word, I want you to

9:29

describe for me a process for

9:31

how that happens. And it could

9:33

be your process. You can make

9:35

it up. I don't care if

9:37

you write it on a slide

9:39

or a piece of paper and

9:41

crayon, but I just want to

9:43

know that you have a thought

9:46

process here, that you're not just...

9:48

coding like a banshee for 100

9:50

hours a week and we'll see

9:52

where it goes someday. And so

9:54

he was very good at sort

9:56

of not being prescriptive, but he

9:58

would be very socratic and in

10:00

the conversation he would force you

10:02

to reckon with the fact that

10:04

you hadn't really thought about what

10:06

you were doing yet. You were

10:08

just kind of just jumping into

10:11

the fray and just trying to

10:13

overpower the problem by out smarting

10:15

the problem. And so my dad

10:17

used to say to me, sometimes

10:19

it's more important to be proactive

10:21

than smart. And that, you know,

10:23

if you have an intentional strategy

10:25

about how you're going to go

10:27

about something, you'd be surprised how

10:29

few people really do. You'd be

10:31

surprised how few people, most people,

10:33

life just comes at him every

10:36

day. And, you know, he was

10:38

always like, you should, you should

10:40

be very intentional about how you

10:42

choose to spend your time and

10:44

your energy and what you want

10:46

to focus on. Sounds like an

10:48

amazing man. So cool. You know,

10:50

he impacted a bunch of people

10:52

and it was just, you know,

10:54

it's sad to see him go,

10:56

but it was fun to see

10:58

all these people emerge, you know,

11:01

from 30 years ago or more

11:03

who'd said, oh man, I really

11:05

missed him. A celebration, a pure

11:07

celebration, I appreciate that. So I

11:09

want to pivot to something I

11:11

read that you had written in

11:13

pattern breakers and I'm going to

11:15

actually go to the back of

11:17

the book or close to the

11:19

back of the book. What did

11:21

you learn from Jonathan Livingston Siegel

11:23

when you were in second grade?

11:26

Oh yeah, it's a great book,

11:28

right, by this guy named Richard

11:30

Bach. And so it was popular

11:32

in the early 70s. You know,

11:34

that book, and there was another

11:36

few that I really liked at

11:38

the time, be here now by

11:40

Rom Doss and Zen in the

11:42

art of motorcycle maintenance by Robert

11:44

Persig. And so, okay, but Jonathan

11:46

Livingston Siegel is a Siegel, and

11:48

he's in a flock. And he

11:51

says, I want to fly. faster

11:53

than any seagulls ever flown before.

11:55

I don't want to just eat

11:57

scraps off of the surface of

11:59

the ocean. and be a dirty,

12:01

yucky-looking bird, I want to achieve

12:03

perfect flight. And all the other

12:05

seagulls are like, dude, you're crazy,

12:07

we're seagulls, right? This is how

12:09

we're meant to live, you know,

12:11

just quit having these goofy fantasies

12:13

about what you could be. And

12:16

eventually they get so tired of

12:18

them that they cast them away

12:20

from the flock. So, you know,

12:22

I saw this book on my

12:24

dad's table. And it was a

12:26

small book and I asked him

12:28

what it's about and he said,

12:30

well, you know, it's classic. My

12:32

dad, he's like, well, why don't

12:34

you read it and tell me

12:36

what you think it's about. And

12:38

so I read it and I

12:41

said to him, and I doubt

12:43

I had the words, but this

12:45

is kind of what I got

12:47

from it was that, so by

12:49

the way, Jonathan Livingston Siegel does

12:51

achieve, there are really limits of

12:53

your own mind and your own

12:55

self-imposed limitations. And so if you

12:57

want to break limits, you have

12:59

to break the chains of the

13:01

limits that you've created for yourself

13:04

in your own mind. It's not

13:06

about necessarily the world stopping you.

13:08

The world is actually a surprisingly

13:10

malleable place, but most people are

13:12

limited in their capacity to affect

13:14

change. because of their limited beliefs

13:16

about their ability to do so.

13:18

Why do we put these self-limiting

13:20

beliefs on ourselves? Yeah, I think

13:22

without realizing it, we're our own

13:24

biggest critic. You know, if you

13:26

think about just the mind chatter

13:29

that goes on and I'm guilty

13:31

of this as much as the

13:33

next guy, maybe you found a

13:35

way Ryan to solve for this,

13:37

but like probably within a minute

13:39

of time. There's some background noise

13:41

in your mind saying you're not

13:43

good enough This isn't going to

13:45

work. What if you say the

13:47

wrong thing here? What if you

13:49

do this wrong? It's there all

13:51

the time And what I've kind

13:54

of learned is that I've never

13:56

found a strategy to make it

13:58

go away. You know, you could

14:00

meditate, you could do a bunch

14:02

of things. So what I do

14:04

now is I just say, oh,

14:06

well, that's my mind being rude

14:08

to me and saying those things,

14:10

but I don't have to listen

14:12

to that. I don't have to

14:14

buy into what that voice is

14:16

saying. I can choose what to

14:19

do in this moment. And I

14:21

can just kind of like... you

14:23

know almost look at that voice

14:25

like it's a comedy and not

14:27

a tragedy and just say up

14:29

there you go again saying your

14:31

negative stuff well who says you

14:33

get a say and so like

14:35

that's I think a reason that

14:37

a lot of us a lot

14:39

of us are self-critical all the

14:41

time as a background part of

14:44

our operating system in our mind

14:46

and we we start to buy

14:48

into those beliefs of the self-doubt

14:50

but then I think also we

14:52

get told You know as we

14:54

grow up, you know, when you're

14:56

a little kid, you know, you

14:58

you turn a box into a

15:00

fantasy rocket ship and pretend that

15:02

you're an astronaut and you imagine

15:04

that you could do all kinds

15:06

of things, but then as you

15:09

grow up, you get told that

15:11

you need to stay within the

15:13

lines and this is the rules

15:15

and you get good grades when

15:17

you give the teacher answers the

15:19

questions they want to hear, you

15:21

get rewarded for achieving in the

15:23

existing status dominance hierarchy. according to

15:25

the rules that govern that status.

15:27

And so I think you just

15:29

start to become much more tuned

15:31

into the opinions of the other

15:34

than your own independent ideas about

15:36

what's possible. And so I think

15:38

that that's another thing that gets

15:40

beaten out of us over time,

15:42

unfortunately. You know, Mike, I have

15:44

a thought on this that has

15:46

been helpful to I think get

15:48

rid of that voice in my

15:50

head. And I wonder if you've

15:52

experienced the same thing. So I'll

15:54

serve as a thesis and then

15:56

you can respond. After 618 of

15:59

these conversations over the past... decade,

16:01

I've been so fortunate to meet

16:03

some of the greatest leaders in

16:05

the world, people who have accomplished

16:07

massive, massive things. And I'm often

16:09

asked, what do they have in

16:11

common? What do they share? And

16:13

that's some stuff that we're going

16:15

to talk about with pattern breakers

16:17

and things that you've learned as

16:19

well. And there's a lot, but

16:21

one of them that comes up

16:24

so frequently is we are all

16:26

figuring it out as we go.

16:28

Every once in a while I'll

16:30

meet the genius who does have

16:32

it more figured out than most

16:35

every once in a while But

16:37

almost across the board once you

16:39

really get to know the people

16:41

and you get inside a little

16:43

bit more and you and you

16:45

dig deeper and maybe you have

16:47

multiple conversations and you get to

16:49

you have dinner or something like

16:51

that man We're almost all figuring

16:53

it out as we go and

16:55

to me that is massively inspiring

16:57

that is like There are no

16:59

limits to what I can do.

17:01

Why not have like one of

17:03

the crazy things I'm thinking about

17:06

now is like creating the biggest

17:08

best leadership development festival of all

17:10

time. That is a stupid crazy

17:12

idea. Who am I to think

17:14

I could do that? But then

17:16

I think, why not? Somebody's got

17:18

to do it. You know what

17:20

I'm saying? So why not me?

17:22

And that's because of talking to

17:24

so many people who have done

17:26

massive things that figured it out.

17:28

as they went and I'm curious

17:30

and from your life I mean

17:32

you're backing people who have crazy

17:34

ideas and some of them hit

17:36

so some of them probably are

17:39

like actual geniuses but I bet

17:41

I don't know you tell me

17:43

a lot of them just kind

17:45

of have been really good at

17:47

figuring it out as they go

17:49

yeah and it's funny the expression

17:51

I use colloquially is everybody's winging

17:53

it you know like even most

17:55

successful people like I remember when

17:57

Trump first ran for president the

17:59

first time. I'm like, you know,

18:01

I was talking to somebody about

18:03

him and you know I'm not

18:05

all that political but I'm just

18:07

like he's winging it and any

18:10

and they're like well do you

18:12

think that means he's gonna lose

18:14

and I'm like not necessarily that

18:16

may be why he wins but

18:18

like you know everybody's winging it

18:20

and they're like not everybody's winging

18:22

it I was like no everybody's

18:24

winging everybody and the sooner you

18:26

figure that friend of mine goes

18:28

oh my gosh Trump was winging

18:30

it and he won and I

18:32

was like, I told you. But

18:34

everybody's winging it and that doesn't

18:36

mean you don't have a plan

18:38

that doesn't mean you're not prepared.

18:41

Yeah, but sometimes you have to

18:43

believe even when you don't believe

18:45

and it's like you just have

18:47

to you have to have faith

18:49

that you'll get through it and

18:51

just because you don't know how

18:53

the dots are going to forward

18:55

connect doesn't mean they won't connect.

18:57

You live close to the right

18:59

brothers right who you know. All

19:01

the scientists in the world were

19:03

saying it was going to take

19:05

a thousand to a million years

19:07

for flight, and it was a

19:09

waste of time to even try

19:12

to do it, the science couldn't

19:14

let it happen. Well, the Wright

19:16

brothers realize that they don't get

19:18

to decide who invents flight. The

19:20

person that does the job gets

19:22

to decide who invents flight. And

19:24

so it's the person who gets

19:26

on the playing field and plunges

19:28

ahead through the uncertainty that gets

19:30

to define what the future is

19:32

going to be. and they get

19:34

to define the patterns that we're

19:36

gonna all have to react to,

19:38

but it's not like they're all

19:40

that different other than just the

19:42

fact that they're willing to stand

19:45

up and try to make a

19:47

difference. They're like that seagull, right,

19:49

who's willing to do perfect flight

19:51

without knowing exactly how he's gonna

19:53

get there. Yeah, you're right in

19:55

pattern breakers George Melville who was

19:57

the US at the time in

19:59

1901 was the United States Navy's

20:01

chief engineer He called aviation quote

20:03

a useless dream and the Wright

20:05

brothers were flying an aircraft to

20:07

later. I am juiced by people

20:09

that think that crazy, that are

20:11

like, no, we're gonna go do

20:13

this. And that's kind of like

20:16

what your life's about, right? You're

20:18

backing people, you're putting your money

20:20

behind people who have crazy beliefs

20:22

and thoughts like that. I'm just

20:24

curious, what made you want to

20:26

get into that line of work

20:28

to back people who are crazy

20:30

enough to invent something or to

20:32

try to create something that others

20:34

say... What are you talking about?

20:36

That doesn't make any sense or

20:38

that will never work. And they

20:40

say, oh, I think it will.

20:42

And then away they go. Yeah,

20:44

it's funny. I like to say

20:47

to people that I have a

20:49

specific set of skills. So like

20:51

most business people are probably more

20:53

along the sensibilities of somebody like

20:55

Warren Buffett, right? So Warren Buffett

20:57

would say, what's a good company?

20:59

A good company has a competitive

21:01

moat, you know, has a brand,

21:03

it has persistent advantages, and it

21:05

compounds over decades. A startup doesn't

21:07

have any of those things. A

21:09

startup doesn't have a moat, doesn't

21:11

have customers. All it is is

21:13

the founders and their idea. And

21:15

so what I realize is that

21:18

startup capitalism is different. So a

21:20

startup capitalist doesn't create value by

21:22

persistently compounding. A startup capitalist creates

21:24

value by changing the subject. You

21:26

know, they create something radically different

21:28

that's never been seen before. and

21:30

that's how they add value to

21:32

the economy. And so when it

21:34

comes to startups, I like to

21:36

say better doesn't matter. Only by

21:38

being radically different can you make

21:40

a radical difference. And so I

21:42

just got really excited and inspired

21:44

by people who do that by

21:46

people who are daring enough to

21:48

create these legendary radically different ideas,

21:51

most of which won't work. But

21:53

it's like, you know. We would

21:55

all be still living in caves

21:57

if somebody wasn't always willing throughout

21:59

human history. to imagine that there is

22:01

a better explanation for how the world could

22:03

be. And so those people inspire me, right?

22:05

I think you can be a very successful go

22:07

with the flow type of person, but the people

22:09

that I get excited about show up in

22:12

the world differently. They're not people who want

22:14

to go with the flow. There are people

22:16

that want to be like Jonathan Livingston Siegel

22:18

or Jack Dorsey or, you know, I wish

22:20

I'd been smart enough to invest in Brian

22:23

Chesky when I met him at Airbnb and

22:25

Airbnb. But those are the kinds of people

22:27

that get me excited. Let's compare and

22:29

contrast that. So you were on the

22:31

Forbes Midas list, I believe eight of

22:33

the past 10 years, and that's the

22:35

list of the essentially the best investors

22:37

in the world. Is that what is

22:39

that accurate? Well, people have had

22:42

some good wins and venture capital.

22:44

Yeah, so so best investors in

22:46

the world, you're on that list

22:48

eight of the past 10 years.

22:50

So undisputed and you talk around

22:52

this industry and Mike Maples, you're

22:54

like everyone's like that's the guy.

22:56

So let's compare and contrast. Twitter

22:58

which I believe was called

23:00

audio when you invested versus

23:03

Airbnb and Brian Chesky which it

23:05

sounds like is one that you

23:07

passed on can you take us

23:09

inside your mind the meetings the

23:11

conversations for Twitter slash audio

23:13

as well as Brian Chesky

23:16

and Airbnb sure and and they'll

23:18

probably it'll be useful also

23:21

in illustrating you know like

23:23

in When people describe startups, sometimes

23:25

it sounds like a case

23:27

study that's tidy somehow. And

23:29

startups are wild. They're like

23:32

capitalist mutations. It's like spotting a

23:34

new kind of bird in the

23:36

Galapagos archipelago, right? And

23:38

so, you know, Twitter started out

23:40

as a podcasting company called Odio.

23:42

And I was very excited about

23:45

podcasting and I met Evan Williams.

23:47

He had started a company

23:49

called Blogger before. that got bought

23:51

by Google. And so he'd already had

23:53

a success. And he had a very

23:56

elegant product. And I was like, OK,

23:58

I want to do this first ever.

24:00

angel seed investment I'd ever made.

24:02

And so a week after, yeah, a

24:04

week after my check clears, Apple decides

24:06

to give podcasting away on iTunes. You

24:09

know, this is before the iPhone, right?

24:11

So like, there weren't any devices to

24:13

play podcast on other than iPod to

24:16

speak of. So Apple has a monopoly

24:18

on the playback device and they're giving

24:20

podcasting away on their iTunes service. You're

24:22

like, okay, that's a real problem, right?

24:25

Like I'm not sure we have a

24:27

business. And so Ev tries to figure

24:29

out a business for the better part

24:32

of a year and he can't find

24:34

one. And so eventually he calls me

24:36

and says, I've just decided I'm going

24:39

to give all the investors their money

24:41

back. And, you know, because some of

24:43

the investors were disenchanted and, you know,

24:46

why am, why did I still have

24:48

my money in this thing? It's not

24:50

a good startup. And so, so I

24:52

was like, look, you know, you don't

24:55

know me anything, you win some, you

24:57

lose some. He goes, look, I just

24:59

rather give everybody their money back and

25:02

I'll just own all the intellectual property

25:04

and all that. And so I said,

25:06

okay, that's cool. Do you have any

25:09

other ideas? And he says, well, working

25:11

on this thing, it's a side project

25:13

right now, we're either going to call

25:16

it voicemail 2.0 or TWTR. then what

25:18

happens? He goes, that's it. Oh, I

25:20

forgot 140 characters or less, because we

25:22

want to be able to do it

25:25

with SMS messages. And I was like,

25:27

okay, what's the revenue model for something

25:29

like that? And he goes, there is

25:32

no revenue model. And he goes, there

25:34

is no revenue model. And I say

25:36

to him, have, you know, why do

25:39

you think this is even a product,

25:41

much less a business? And he said,

25:43

oh, I have no idea if it's

25:46

a business or not. But I figure.

25:48

that when I wrote blogger software that

25:50

a million people wrote blogs and podcast

25:52

is a little hard right you got

25:55

to upload audio you got to have

25:57

the right equipment stuff I figure that

25:59

if you made it really easy for

26:02

people to write a tiny little blog

26:04

like in the form of a tweet

26:06

that maybe 10 million people would do

26:09

that and if that happened then the

26:11

burden of proof would be on the

26:13

people who are negative about the idea

26:16

and so so I was like okay

26:18

I want to invest in this you

26:20

know And he says, well, there's nothing

26:22

to invest in. There's no company. There's

26:25

no product. And so then it blows

26:27

up at South by Southwest, and all

26:29

of a sudden it becomes kind of

26:32

an early phenomenon. And I'm like, well,

26:34

now I'm probably not going to get

26:36

to invest in it. Everybody's going to

26:39

be chasing it. One day I have

26:41

calls me and says, hey, did you

26:43

mean it when you said you wanted

26:46

to invest? Because if you meant it.

26:48

now's the time I've reserved an allocation

26:50

for you if you're interested. So you

26:52

know he was honorable to me twice

26:55

right giving me my money back and

26:57

then letting me invest the next time

26:59

and you know it was one of

27:02

those things where there's so much drama

27:04

right there was the fail whale there

27:06

was like who's gonna be the CEO

27:09

is it gonna be Ev is it

27:11

gonna be Jack is it gonna be

27:13

Dick is it gonna you know who

27:16

what's gonna happen but it was just

27:18

like it was just a great idea

27:20

you know some some ideas are just,

27:22

it's like you trapped lightning in a

27:25

ball, it doesn't matter how you execute.

27:27

It just destined for greatness. So that

27:29

was Twitter. How much are you investing

27:32

in the idea versus how much are

27:34

you investing in the person or the

27:36

people involved? I'd say it's more biased

27:39

towards the people involved, but with a

27:41

caveat, like, it turns out in my

27:43

experience, they're not independent variables. So a

27:46

great founder. will be discerning enough to

27:48

allocate their limited time to an idea

27:50

that's worthy of their time. And so

27:52

if if a founder that you think

27:55

is great is something not so great,

27:57

that's a yellow flag that you overestimated

27:59

the founder. But what's interesting is the

28:02

very very best founders that I work

28:04

with, they have an authenticity to them

28:06

where you're like, oh man, if anybody

28:09

in the world was gonna do this

28:11

idea, it would be this guy. They're

28:13

just the perfect person to do it.

28:16

You know, Ev was the perfect person

28:18

to be a co-founder of Twitter because

28:20

he'd done blogging software before he. He

28:22

just had a very natural set of

28:25

instincts around self-expression. He was early in

28:27

Web2.0. He was just from central casting

28:29

to be part of something like that.

28:32

You know, you can't fake authenticity and

28:34

most of the most of the great

28:36

startups come from very authentic founders and

28:39

their authenticity gives them a competitive advantage.

28:41

It gives them a first mover advantage

28:43

into the future because they have a

28:45

better. set of instincts about what needs

28:48

to be built, and they're more likely

28:50

to convince other people to follow them

28:52

because their authenticity is contagious. They just

28:55

have such a core belief. in the

28:57

thing that they're doing that it just

28:59

almost rubs off on you that they

29:02

have this confidence and belief in something

29:04

that doesn't because like looking back it's

29:06

easy well obviously Twitter works or obviously

29:09

you should invest in an Uber or

29:11

Airbnb or you know all of them

29:13

it's so easy looking back at the

29:15

time though none of these things that

29:18

you invested in were were quote working

29:20

they they were just an idea with

29:22

a person or people that's the thing

29:25

that's so hard because then we're trying

29:27

to look into the future we're trying

29:29

to make these strategic bets in the

29:32

future it's easy looking back but so

29:34

hard looking forward so you're saying a

29:36

guy like Ev you just felt was

29:39

the right person at the right time

29:41

with the right idea with the right

29:43

amount of conviction that the thing would

29:45

work yeah and you know if some

29:48

of your fans are like NFL football

29:50

fans it reminds of like so unfortunately

29:52

I rooted for the 49ers last year

29:55

I was at the Super Bowl rooting

29:57

for the Niners and we're playing against

29:59

the Kansas City Chiefs and it's towards

30:02

the end of the game and it's

30:04

overtime and it's like the Chiefs have

30:06

the ball and I'm sitting there thinking

30:09

oh crap it's Mahomes what's he gonna

30:11

do to us this time I don't

30:13

know what play he's gonna run next

30:15

but I know that I just am

30:18

like my whole body is clenched up

30:20

Because oh God, it's that Mahomes guy

30:22

again. And it's like, you know, the

30:25

great founders are kind of like that,

30:27

right? You just want to hand them

30:29

the ball and wait to be amazed.

30:32

And they just have this ability to

30:34

just overcome whatever circumstances are in front

30:36

of them. And part of how they

30:39

do that is through their authenticity. You

30:41

know, they're just so obsessed with the

30:43

idea that they're pursuing that they come

30:45

up with the right product ideas because

30:48

they're genuinely interested in what they're working

30:50

on. but then they also just have

30:52

this determined view of what the future

30:55

needs to be and that determination is

30:57

contagious right and it gets I'm sure

30:59

part of why my home succeeds is

31:02

the players on his offense are like

31:04

okay this is our time this is

31:06

our moment we got this my home's

31:09

gonna take us there oh we're in

31:11

the red zone now we score one

31:13

red zone and I'm sitting there thinking

31:15

oh crap now they're in the red

31:18

zone and it's like he's gonna score

31:20

no It's like watching a slow motion

31:22

train wreck if you're on the other

31:25

side, if you back founders who have

31:27

that set of skills in their domain,

31:29

you don't need to know how they're

31:32

going to succeed specifically just that they

31:34

will or that they're likely to. It's

31:36

so cool to see the Mahomes type

31:39

of MJ's back in the day, Kobe

31:41

had it, where their belief in themselves,

31:43

their preparation, their work ethic, their history.

31:45

creates it almost raises the level of

31:48

the people around them because they want

31:50

to be able to hang with him

31:52

be a teammate who adds value. And

31:55

so those people are so, I remember

31:57

Pat McAfee made this great point when

31:59

the Tampa Bay Bucks signed Tom Brady.

32:02

They said, what I don't think everybody

32:04

understands is he's going to raise the

32:06

level of performance of every single person

32:09

in the entire. building. The equipment guy

32:11

will be better, the trainers will be

32:13

better, the person making the food and

32:15

the cafeteria will be better, the general

32:18

manager will be better, he'll go get

32:20

more players, the coaches will raise their

32:22

level to the people like that. Not

32:25

only are they excellent at their craft,

32:27

but they're also really good at raising

32:29

the expectations and their performance, I think,

32:32

of others around them and that. is

32:34

leadership, like that is being a leader

32:36

is raising the level of performance and

32:39

expectations of those around you. I feel

32:41

like that's where you've probably got the

32:43

experience in the startup world. Yeah, and

32:45

it's and it's really not fun to

32:48

compete against people like that, right? So

32:50

like I remember a few years ago,

32:52

so I like Steph Curry a lot,

32:55

right, the Warriors. And so they're playing

32:57

against Oklahoma City and there's this film

32:59

of him going up. It's like the

33:02

very end of the end of the

33:04

game. They're just barely down. And you

33:06

hear a fan in the audience who's

33:08

filming it saying, not him, don't have

33:11

the ball, not him, not him, not

33:13

him. And he goes across the half

33:15

court line, he's like, not him, not

33:18

him. And he just heaves this ball

33:20

up from downtown and hits a three

33:22

on the buzzer. And he goes, no,

33:25

not him, not him. That's what the

33:27

French were saying, you know, in the

33:29

Olympics. Olympics. Why did they keep giving

33:32

it to that devil? You know, he

33:34

would just every time, you know, he

33:36

would just heave it from, you know,

33:38

they'd be, it's not like it wasn't

33:41

occurring to them to try to stop

33:43

him, but it's just like, you know,

33:45

you get into that zone where you,

33:48

you just know you can't be stopped.

33:50

And, you know. And you're right, it

33:52

feeds that energy, feeds on everybody else

33:55

on the team, you know, the team

33:57

starts to develop a belief that they

33:59

just can't be stopped. And that's really

34:02

hard to compete against. Yep. Let's flip

34:04

it to the opposite side of things.

34:06

I don't know the story. Brian Chesky.

34:08

Looking back, obviously, Mike, you should have

34:11

invested in Airbnb. What are you thinking?

34:13

You're stupid. What do you mean? Oh,

34:15

why not? Yeah. So what happened there.

34:18

Well, so this was kind of a

34:20

funny thing. So the prior week, we've

34:22

been pitched by a company called Mojo

34:25

Mix, which was you go to a

34:27

website and you specify ingredients that you

34:29

want in your cereal. And then it

34:32

assembles those ingredients and chips it to

34:34

you in a box. And my partner

34:36

Anne and I are looking at this

34:38

thing. And at the end of the

34:41

meeting, Anne's like, why did we take

34:43

this meeting? This isn't something we invest

34:45

in. We don't invest in serial companies.

34:48

We have no business even talking to

34:50

these people. I mean, I wish them

34:52

well, but it's not our business. And

34:55

I was like, well, it's technology enabled

34:57

to cereal. She's like, come on. And

34:59

so a week later, I take this

35:02

meeting with, at the time, it's called

35:04

Airbed and Breakfast. And we walk into

35:06

the conference room and it's full of

35:08

cereal boxes. Obama owes and Captain McCain

35:11

crunch. And you know, people don't remember

35:13

this, but he financed the company in

35:15

the early days by selling cereal boxes.

35:18

because he couldn't raise money. So we

35:20

walk in there and Anne kind of

35:22

looks at me like Maples, what the

35:25

hell, another serial company and I'm looking

35:27

at her like, you know, they didn't

35:29

say it was serial. You know, like

35:32

so I'm like, hey Brian, what's like

35:34

what's going on here with his serial?

35:36

He goes, well, you know, we're funding

35:38

the company by selling serial. Would you

35:41

like to buy a box at $30

35:43

for a box? And I made my

35:45

first mistake. Where you know Michael Sibel

35:48

who introduced us says that you don't

35:50

really like slides you like demos So

35:52

we're going to show you the software.

35:55

I was like great. That's right So

35:57

he tries to get the software to

35:59

run and he can't get it to

36:02

work. So for some reason the server's

36:04

down. So I'm like, that's okay. Slides

36:06

are okay. We'll just look at slides.

36:08

He goes, well, I didn't bring any

36:11

slides because I heard you like demos.

36:13

So we're sitting there 20 minutes into

36:15

the meeting, room full of serial boxes,

36:18

and I still have no idea what

36:20

they do. We're just looking at each

36:22

other, right? This conference room. And so

36:25

then he says, you know, air bed

36:27

and breakfast, we let you rent an

36:29

extra room in your house, and then

36:32

you serve, you give the person an

36:34

air mattress and you serve them pop

36:36

tarts the next morning. And so I'm

36:38

like, okay, I'm like, I'm not sure

36:41

I get this. Isn't there something already

36:43

called couchsurfing.com and it's free? Why are

36:45

people going to pay for your thing

36:48

that costs money when it's free with

36:50

couchsurfing.com? And he goes, well. because it's

36:52

not about price, it's about trust. And

36:55

people are going to want good pictures

36:57

of the place that they're staying at,

36:59

and they're going to want a trust

37:02

rating mechanism. And that's where I made

37:04

the mistake. I didn't realize what his

37:06

insight was. His insight was about the

37:08

internet and trust mechanisms and Facebook Connect.

37:11

We're going to make it possible for

37:13

you to create a substitute for the

37:15

trust that people had in hotels. He

37:18

was right, it wasn't about price, it

37:20

was about trust. But the meeting was

37:22

just so convoluted and screwed up that

37:25

I just didn't, I just didn't see

37:27

it, you know, and so I missed

37:29

it. It was the biggest miss in

37:31

my career by a wide margin. So

37:34

I would have made, God, it hurts

37:36

to say, I would have made over

37:38

5,000 times my money if I had

37:41

said yes to it. Yeah, I guess

37:43

there's the ones you learn from. But

37:45

did you feel something special in Brian

37:48

Chesky though? I mean, because now you

37:50

look at him like, this dude's amazing.

37:52

Like every time he speaks, we're all

37:55

taking notes, every podcast he goes on.

37:57

he's talking, I think he's almost universally

37:59

admired by all who study this stuff

38:01

as being one of the best CEOs

38:04

in the world. Could you sense that

38:06

years ago in him? Yeah, I mean,

38:08

I thought even then that he definitely

38:11

had this X factor to him. And

38:13

to kind of give you a sense

38:15

of that, I ended up introducing him

38:18

to Reed Hoffman, right, who was the

38:20

founder of LinkedIn, and I said, Reed,

38:22

you know. I don't know if this

38:25

is a fit for me, but this

38:27

guy is interesting and he's somebody you

38:29

should know. And I don't know if

38:31

you're going to want to invest in

38:34

airbed and breakfast or not, but I

38:36

think this is somebody you need on

38:38

your radar because he's going to do

38:41

something. And you know, I should have

38:43

known better. But you know, sometimes you

38:45

just. You have so many meetings and

38:48

you meet with so many companies and

38:50

you know, the meeting was so convoluted

38:52

and screwed up and you did, I

38:55

just wasn't awake enough to the possibilities.

38:57

And I, you know, failure of imagination.

38:59

Yeah. No, that's part of the game

39:01

though. That's part of the pain and

39:04

that's how we learn from that. Mike,

39:06

I'm looking behind your left shoulder and

39:08

I see a sign that says practice

39:11

reckless reckless optimism. What does that mean

39:13

to you? Yeah, well it was given

39:15

to me by a founder actually, so

39:18

somebody that I worked with twice, a

39:20

guy named Dominic Zane, gave it to

39:22

me for Christmas one year. And you

39:25

know, kind of the idea is that

39:27

you want to believe that a different

39:29

future is always possible, always around the

39:31

corner. And you know, so I like

39:34

to think of myself not as an

39:36

investor, but as a co-conspirator. I think

39:38

of a startup as an optimistic conspiracy

39:41

theory to make a better future. and

39:43

you know most people we haven't really

39:45

talked about this but most startup ideas

39:48

that are great are disliked by most

39:50

people at first because if you know

39:52

human beings are conditioned to like things

39:55

so if everybody likes your startup idea

39:57

it's too similar to what they already

39:59

like the best startup ideas force a

40:01

choice and not a comparison. You know,

40:04

this is not a startup, but it's

40:06

an example of the thinking the Tesla

40:08

cyber truck. You know, you may want

40:10

one, you may not want one, you

40:12

might think it's ridiculous. When I first

40:14

saw the cyber truck, I thought maybe Elon

40:17

was joking. Is he really going to

40:19

ship that? You know, but like nobody

40:21

when they see a cyber truck ever

40:23

says, how does that compare to a Ford

40:25

F-150? Right. live in Elon's future

40:27

or don't, but there's no

40:29

comparison between the two. You

40:31

can't reconcile the two things. And

40:33

so that's what I find startups

40:36

are that way when they're great.

40:38

They start out by being

40:40

non-consensus and right. So it's almost

40:42

like you're the Ocean's 11 team

40:44

trying to rob the Balagio safe,

40:46

right? You're like, you're trying

40:49

to perpetrate something, and most

40:51

people don't believe that it should

40:53

happen. And so you're you kind of

40:56

believe that you're in on a secret

40:58

about the future with a bunch of

41:00

other like-minded crazy people. And I call

41:02

that co-conspirators, right? And so I want

41:04

to be more of a co-conspirator

41:07

than an investor because I think that

41:09

startup founders need a different kind of

41:11

help. They don't need a Bylos sell

41:14

high type of helper. They need someone

41:16

who's in on the secret with them

41:18

and who believes in the same crazy thing

41:20

that they believe and wants to. part

41:22

of the different future wants to be

41:24

a reckless optimist, you know, alongside them.

41:27

Optimists are the ones who changed

41:29

the world, right? pessimists sound smart.

41:31

Morgan Housle said that on this

41:33

podcast, but optimists actually make a

41:35

difference. They're the ones who make

41:37

it happen. They change the world.

41:39

James Clear talked about on this

41:41

podcast too, about the fact that he

41:44

wants to be around, I do too,

41:46

people who are four things, people who

41:48

bet. on something. The only way to

41:50

achieve or to experience the upside is

41:53

you can't just hate on things or

41:55

be a pessimist, then you're not part

41:57

of anything. You're just a hate. But

42:00

if you want to be a

42:02

part of the upside, if you

42:04

want to have a chance to

42:06

make a difference, to leave a

42:08

debt in the world, you have

42:10

to be four things. You've got

42:13

to bet on something. You've got

42:15

to commit to something. And that's

42:17

why I've loved studying your work,

42:19

Mike, because I feel like that's

42:21

your life. That's like your ethos.

42:23

It kind of pours out of

42:25

you, even as we're just talking

42:27

now that you're this guy who

42:30

believes in crazy ideas. changing something

42:32

in a radical way and you're

42:34

willing to put your money where

42:36

your mouth is and that's how

42:38

you've built your entire career. Well

42:40

we try right and I guess

42:42

it's kind of a version of

42:44

doing your best right but like

42:47

you know it's sort of like

42:49

all right you don't know how

42:51

much time you're gonna have how

42:53

do you want to use your

42:55

time succeeding by somebody else's conventional

42:57

idea of success and conforming to

42:59

their dogma about how things should

43:01

be how things should be and

43:04

trying to win within that status

43:06

dominance hierarchy, or do you kind

43:08

of say, you know, like there's

43:10

a book that I really like

43:12

called The Beginning of Infinity by

43:14

David Deutsch, and he's this theoretical

43:16

physicist who talks about how we're

43:18

at the beginning of infinity of

43:20

knowing what's knowable, but the good

43:23

news is that all knowable things

43:25

can be known. And so why

43:27

not try? Why not always, you

43:29

know? What is a theory really

43:31

it's a better explanation for how

43:33

things work than all the explanations

43:35

we have so far? Why not

43:37

always seek a better explanation? Why

43:40

not always believe that if this

43:42

is the pattern that somebody can

43:44

break the pattern and impose a

43:46

new better one and then a

43:48

better one after that and so

43:50

You know that's something I can

43:52

get behind right as people who

43:54

do that whereas You know the

43:57

status quo has the word status

43:59

embedded in it And a lot

44:01

of people try to protect the

44:03

status quo because they're trying to

44:05

protect their existing status. And I'm

44:07

like, what fun is that? You

44:09

know, that's a, that's not, that's

44:11

not a fun way to honor

44:14

the gift of your time. That's

44:16

just passing the time. I spoke

44:18

with your chief of staff, Sam

44:20

Baskin, who by the way, he

44:22

played for my friend Rob Eson

44:24

at Stanford, basketball player, and Rob

44:26

texted me and said, that dude

44:28

might be my all-time favorite player

44:31

and he's gonna be the president

44:33

of the United States someday. So

44:35

just a heads up on Sam

44:37

on Sam I'm not sure I

44:39

would wish that on him, but

44:41

you know, I don't know if

44:43

he wants that, but one of

44:45

the things he said, he sent

44:47

me a list of your favorite

44:50

quotes, and I want you to

44:52

respond to one of them. We

44:54

could have a whole conversation about

44:56

all of these, but one of

44:58

them is there can't be a

45:00

recipe for a breakthrough because by

45:02

definition, breakthroughs haven't happened yet. Again,

45:04

this is in line with what

45:07

we've been talking about, but this

45:09

mindset of There aren't really recipes

45:11

you have to in a way

45:13

invent the new thing or create

45:15

it not follow somebody else's quote

45:17

best practices. Can you talk more

45:19

about breakthroughs and the fact that

45:21

there isn't a definition because they

45:24

haven't happened yet. Yeah, and when

45:26

you think about it, it makes

45:28

intuitive sense. So let's say that

45:30

you and I follow a recipe

45:32

to make a cake. We might

45:34

make an awesome cake. But we're

45:36

not going to invent something in

45:38

so doing. We're following somebody else's

45:41

playbook that's already been determined. Somebody

45:43

else figured out how to create

45:45

that cake and pass it down

45:47

to us. And so if we're

45:49

going to have a breakthrough, we

45:51

have to do something nobody's ever

45:53

done before. So there can't be

45:55

a recipe by definition. So what

45:58

I've learned is that it's the

46:00

wrong question to ask, right? Like

46:02

the question to ask is... how

46:04

do I become the type of

46:06

person who's likely to encounter a

46:08

breakthrough, right? And so, you know,

46:10

you listen to some of the

46:12

great great people in history, the

46:14

creative geniuses, Louis Pasteur, right, who

46:17

said, chance favors a prepared mind.

46:19

Isaac Newton, the apple hits his

46:21

head, Archimedes, jumps out of a

46:23

hot tub and says, Eureka, I

46:25

found it when displacement occurs to

46:27

him. The history is written in

46:29

terms of them having this flash

46:31

of insight, almost like a happy

46:34

thought. You know, Einstein talks about

46:36

how. Relativity crystallized for him when

46:38

he was in a train and

46:40

he was moving away from a

46:42

clock and he saw it going

46:44

off in the distance. But they

46:46

asked Isaac Newton one time at

46:48

a party, how is it that

46:51

when that apple hit you on

46:53

the head, all of a sudden

46:55

gravity occurred to you? And he

46:57

said, because I was thinking about

46:59

it all the time. So that's

47:01

the thing that people don't get

47:03

about breakthroughs is that. Chance favors

47:05

the prepared mind because when you're

47:08

thinking about the edge of something

47:10

new for its own sake independently

47:12

because you're intrinsically motivated by it,

47:14

you're gonna get visited by luck

47:16

often. But the problem is most

47:18

of us are just trying to

47:20

get through the day. We're trying

47:22

to follow the recipe for what

47:25

needs to happen next. We all

47:27

get visited by luck. Just most

47:29

of us don't answer the door.

47:31

Most of us don't realize that

47:33

we've been visited by the muse.

47:35

The great founders, the great scientists,

47:37

the great artists, you know, that

47:39

people have studied people who create

47:41

these breakthroughs. And I'm convinced that

47:44

Chance does favor the prepared mind,

47:46

but the reason it does is

47:48

that prepared minds say yes to

47:50

luck more often. Right? Like prepared

47:52

minds, no luck when they see

47:54

it. Most people don't have enough

47:56

agency to realize they're always being

47:58

visited by luck. But they're

48:01

not, they're, they're too focused on

48:03

what's in front of them to

48:05

notice what's around them. And so

48:07

like one of my favorite verbs

48:09

about entrepreneurship is noticing. And it's

48:11

like, you know, it's like the

48:13

people that notice the surprising anomaly

48:15

hidden in plain sight that change

48:17

the future. But when you realize

48:19

that, it's kind of inspiring, you

48:22

know, inflections are all around us

48:24

all the time. opportunities change the

48:26

future are all around us ever

48:28

present. The Wright brothers didn't have

48:30

any unfair advantage in inventing the

48:32

plane. They were just more curious.

48:34

And so, you know, I think

48:36

that that's the key, right, is

48:38

to not look for recipe or

48:40

playbook, but to try to try

48:42

to be the type of person

48:44

that is going to be visited

48:47

by luck more often. and is

48:49

going to be awake to the

48:51

possibility of answering the door when,

48:53

you know, I like to say

48:55

that I think that Luck has

48:57

a little bit of a feminine

48:59

quality. You know, the Greeks talked

49:01

about being visited by the muse.

49:03

I think that, you know, sometimes

49:05

you're visited by the muse, but

49:07

you have to be open to

49:09

the possibility that she's going to

49:11

knock, and she's usually not going

49:14

to come through the front door.

49:16

She's going to come through the

49:18

side door. And so, you know,

49:20

you kind of just got to

49:22

be awake to be awake to

49:24

the possibility to the possibility that

49:26

she's visiting today that she's visiting

49:28

today. Love your favorite verb. When

49:30

I think about the most interesting

49:32

people that I've ever met and

49:34

the most interesting people in my

49:36

life, I think they are far

49:39

in away the best noticer of

49:41

things, have great spatial awareness of

49:43

the world and understanding, they're usually

49:45

very funny. Standup comedians I found

49:47

will probably be some of the

49:49

best notishers in the world. Nikki

49:51

Glazer talked about that on this

49:53

podcast. I feel like I'm name

49:55

dropping all the time, but that's

49:57

just how my mind works is

49:59

from these conversations because they're embedded

50:01

in my mind, but she said

50:03

that that's like her whole life.

50:06

is she'll be in the middle

50:08

of a conversation with a friend

50:10

at a party or something and

50:12

notice something and say hold on

50:14

a second and take out her

50:16

phone and put the note of

50:18

the thing that she just noticed

50:20

because the whole world at all

50:22

times are there's just there's stuff

50:24

happening that you're noticing and I

50:26

think if you almost rewire your

50:28

brain to do that that's how

50:31

some of these breakthroughs can happen

50:33

because you're always like chance favors

50:35

the prepared mind right you're always

50:37

on the lookout and noticing these

50:39

things happening in the world. That's

50:41

right. Most people don't have prepared

50:43

minds, unfortunately. Most people let life

50:45

come at them. Proactive again, right?

50:47

Be proactive again. Yeah, and it's

50:49

interesting. I love the stand-up comedy

50:51

example. We've never talked about this

50:53

before, but like I read this

50:55

book where they talked about Chris

50:58

Rock and his technique. And comedy,

51:00

like all forms of creativity, usually

51:02

involves... forming unexpected connections. So like

51:04

what you know, when you're doing

51:06

a startup, you're you're forming an

51:08

unexpected connection between a new form

51:10

of empowerment and a set of

51:12

desperation that people have. But and

51:14

you're usually harnessing something that pre-existed.

51:16

In addition, you're just connecting the

51:18

dots differently. Comedy, from my understanding,

51:20

is very similar. You're connecting sort

51:23

of the mundane expected everyday life

51:25

and you're juxtaposing it was something

51:27

unexpected. But the other thing that's

51:29

similar to entrepreneurship, if Chris Rock

51:31

is any guide, he'll practice his

51:33

comedy lines on different audiences before

51:35

he gets in front of a

51:37

big audience. And startups are a

51:39

lot like that too. Like you're

51:41

not saying this product, it's either

51:43

going to succeed or fail, I

51:45

better raise some money and you're

51:48

attached to whether it succeeds. You're

51:50

sort of playing almost like a little

51:52

kid would play soccer just kind of

51:55

kicking the ball forward without necessarily an

51:57

idea where it's going to go and

51:59

you're you're not attached to being right

52:01

away. You're willing to be just totally

52:04

wrong. You're exploring a whole bunch of

52:06

lateral possibilities because it's interesting. And if

52:08

you're wrong, so what? You know, it's

52:11

a tiny little audience. The penalty cost

52:13

isn't that high. You're not fixated on

52:15

the cost of being wrong because you

52:17

make the cost of being wrong zero.

52:20

What you're focused on is finding a

52:22

quicker path to being surprised about what's

52:24

right. So then you can. escalate your

52:27

commitments as you increase your certainty that

52:29

you're right. And that's true of comedy

52:31

too, right? Like once, like, Christopher Rock

52:33

in this book I was reading was

52:36

saying, like, you can just tell when

52:38

it lands, you know, you just, you

52:40

could just see the way that their

52:42

body language and their eye was on,

52:45

that one I'm going to use. And

52:47

so I think risk taking is a

52:49

lot like that. Like, you want to

52:52

make it so that you want to

52:54

make it so that you could take

52:56

as many risks as you want. and

52:58

then double down only when it works,

53:01

only when you're surprised to the upside,

53:03

but it's kind of a different way

53:05

of thinking about risk, right? It's about

53:08

thinking about, I'm gonna make the cost

53:10

of failure so low that I'm just

53:12

gonna keep trying until I massively succeed.

53:14

That's the thing. It becomes a quantity.

53:17

an endurance thing. I was just reading

53:19

about James Dyson, now Sir James Dyson,

53:21

right? He got annoyed by the bag

53:23

at his vacuum cleaner. And so he's

53:26

like, I just got to get rid

53:28

of this stupid bag. I need to

53:30

create a bagless vacuum cleaner. Well, you

53:33

know how many times it took him

53:35

to get it right? Just over 5,100

53:37

tries that he messed up, but he

53:39

learned after each one, and eventually he

53:42

got there and became a billionaire and

53:44

I think he's the sole owner of

53:46

that company. an idea, a willingness to

53:49

experiment, a willingness to be okay when

53:51

it doesn't go well, a willingness to

53:53

be resilient and to respond and to

53:55

learn from that failure so that when

53:58

you go back the next time, you

54:00

are a little... bit closer, you're a

54:02

little bit closer, and most people are

54:04

just not willing to endure all of

54:07

that. They'll quit, they'll stop. That's the

54:09

difference between the James Dyson and everybody

54:11

else. And I think that though is

54:14

a key learning for all of us

54:16

as leaders is whatever the thing is

54:18

that we're doing, a big part of

54:20

it is just being willing to continue

54:23

on. to push through and to make

54:25

sure you learn from the small experiment

54:27

before so that you're better the next

54:30

time. And I have to guess though,

54:32

that's got to be a commonality among

54:34

the leaders that you have backed that

54:36

have gone on to do really well.

54:39

Yeah, but it's funny too, like, you

54:41

know, we're talking about noticing things and

54:43

being awake to stuff. You know, earlier

54:45

you mentioned my chief of staff, Sam

54:48

Bescen, right, who was on Stanford's basketball

54:50

team and I think he played, you

54:52

know, you know, on other teams as

54:55

well. graduate school, not long ago I

54:57

was working with him to chart out

54:59

my time management strategy for 2025 and

55:01

I had a very comprehensive way of

55:04

thinking about it. He said, you know,

55:06

when I was at Stanford, the basketball

55:08

coach, they would come up with a

55:11

game plan and they would think about

55:13

every play and all this intricate stuff,

55:15

but then they would create a one-page

55:17

three keys to winning. summary.

55:20

And Sam said that the coach

55:22

would say to us, if we

55:24

do these three things, we will

55:26

win this game today. And he's

55:28

like, everybody on the team knew

55:30

it. Everybody on the team knew

55:32

the three things they had to

55:34

do. The next team that he

55:36

was on, the coaches would have

55:38

this one page, but it would

55:40

have like 20 things on it.

55:42

And it would be like in

55:44

tiny little, you know, footnote-sized type.

55:46

And he's like, the problem with

55:48

that is... There's no keys to

55:51

winning then. If you have to

55:53

win, if you have to remember

55:55

20 things, you remember zero things.

55:57

And so I was like, dude,

55:59

you're totally. right. We need to

56:01

redo this plan. We need to

56:03

be thinking the three things because

56:05

we've got a team at

56:07

floodgate and like the associates

56:09

need to know what they care about

56:11

when they find the next Twitter,

56:13

you know, the next Thunder

56:15

Lizard startup. And if I

56:17

have some comprehensive, you

56:20

know, spreadsheet of 20 different

56:22

things classified, I might impress

56:24

myself with how smartly arranged

56:27

it is. But it's not executable,

56:29

right? It's not executable in

56:31

the same way that that

56:34

one page, three things to

56:36

do game plan. It's not enough

56:38

to be smart about what

56:40

should happen. What you want

56:42

is the thing that everybody

56:45

is willing to get behind and

56:47

do that's better than good

56:49

enough, right, to win. And like,

56:51

you know, Sam, like, I mean,

56:54

you could have just said, okay,

56:56

yeah, whatever. Let's do this spreadsheet,

56:58

right? But like you have to be

57:00

you have to be like wait a second

57:02

here He's totally right, right? He's he's

57:04

given me a helmet adjustment in

57:06

a nice way But like he's just

57:08

totally right that that's what we have

57:11

to do my problem is not that

57:13

I need to be more precise My

57:15

problem is I need to it needs

57:17

to be addition by subtraction, right? That's

57:19

what I need to be focused

57:21

on right now It's like the old saying

57:23

that the word priority didn't used to be

57:26

pluralized and if that's even the right word

57:28

it didn't used to be a plural word

57:30

it used to be singular what is your

57:32

priority and now it's become these are our

57:34

12 priorities and if you have 12 priorities

57:36

just like if you have 12 values You

57:38

pretty much don't have any. You don't have

57:40

to list everything out that that is important

57:43

to you. I think you have to focus.

57:45

I love that idea of the three keys

57:47

to the game. I heard I heard that's

57:49

what the new New England Patriots coach Mike

57:51

Freibel is very good at is three keys

57:53

for the offense, three keys for the defense

57:55

and three keys for the special teams and

57:57

everybody in the entire roster has to memorize

57:59

the three keys before every game

58:01

and they get quiz on it

58:03

and so they understand it just

58:06

these three things we're focusing on

58:08

these three things if I play

58:10

offense defense or special teams and

58:12

I think simplifying that also it's

58:14

hard it's part of partially why

58:16

Twitter works the forced constraints ended

58:18

up being a great great thing

58:21

for it and the same goes

58:23

for time management for keys to

58:25

winning a game and just in

58:27

life in general Mike if you

58:29

have time for one more question

58:31

and we're a little bit over

58:33

but I have one more you

58:36

bet. Yeah, let's say you're meeting

58:38

with somebody who's a recent college

58:40

grad, like Sam's age or maybe

58:42

a little bit younger, and they

58:44

come to you and they actually

58:46

don't fully know what they want

58:48

to do, but they do want

58:51

to leave a positive dent in

58:53

the world. What are some general

58:55

pieces of life slash career advice

58:57

you give to that person? There's

58:59

two. The first is to internalize

59:01

what it really means to do

59:03

your best. And so... You know,

59:06

doing your best means being the

59:08

best version of you that you

59:10

can possibly be as a way

59:12

of expressing gratitude for your time

59:14

and comparing yourself to the best

59:16

version of yourself you can be

59:18

rather than comparing yourself to others.

59:21

You know, avoiding the trap of

59:23

mimetic desire and you know this

59:25

tendency to define your thinking according

59:27

to other people's thinking. People would

59:29

be so much better off if

59:31

they understood that early in life.

59:33

People waste so many of their

59:36

best years trying to succeed according

59:38

to somebody else's idea of what

59:40

success is. So that would be

59:42

the first thing. The second thing,

59:44

and it took me a little

59:46

while to figure this out, but

59:48

eventually I got there. I call

59:50

it the T of knowledge. So

59:53

I have a broad variety of...

59:55

Worldly wisdom topics. I learned this

59:57

from a guy named Charlie Munger,

59:59

and you know, so I try

1:00:01

to know like in the fields

1:00:03

of art, physics, economics, game theory,

1:00:05

system level thinking, engineering, politics, what

1:00:08

are the very best ideas that

1:00:10

have ever existed in those fields?

1:00:12

Because that's kind of like getting

1:00:14

worldly wisdom. And I just think

1:00:16

that, you know, If you read

1:00:18

Aristotle, if you read Aristotle, if

1:00:20

you read Machiavelli, if you read

1:00:23

Sartra, if you read all these

1:00:25

different people, and you're your friend,

1:00:27

and you got to know them,

1:00:29

you got to spend time with

1:00:31

them, and you got to learn

1:00:33

ideas that have stood the test

1:00:35

of time for centuries sometimes, you

1:00:38

know, Marcus Aurelius, you know, all

1:00:40

these people. But then the reason

1:00:42

it's a T is I think

1:00:44

you want to have one area

1:00:46

in life where you are fanatically

1:00:48

obsessed with knowing more about it

1:00:50

than anyone knows. So like for

1:00:53

me that's like startup greatness, right?

1:00:55

Like I have a database of

1:00:57

every company that I know of

1:00:59

in history in tech that would

1:01:01

have made more than 100X on

1:01:03

the first check. And I try

1:01:05

to get a time capsule those

1:01:08

companies. I try to get the

1:01:10

seed round pitch deck. I try

1:01:12

to understand what the founder was

1:01:14

like at the time you would

1:01:16

have had to decide. I try

1:01:18

to figure out whether our frameworks

1:01:20

would have caused us to say

1:01:23

yes or whether we need new

1:01:25

frameworks or whether we need to

1:01:27

discard some. But like, you know,

1:01:29

is that going to lead me

1:01:31

to the next great startup? I

1:01:33

don't know. Probably not. Certainly not

1:01:35

in the next week. But I

1:01:38

just feel like if you do

1:01:40

that. you know, over the course

1:01:42

of 10 years, 20 years, you

1:01:44

just have a gigantic database of

1:01:46

greatness in the back of your

1:01:48

mind of what greatness looks like.

1:01:50

And if nobody else is willing

1:01:53

to do that, I just think

1:01:55

you have an advantage, right? You

1:01:57

come by the advantage honestly, but

1:01:59

like the, you know, in England,

1:02:01

you have these guys, they call

1:02:03

them train spotters, right? They have

1:02:05

these journals and they look at

1:02:08

trains coming and going and everybody

1:02:10

thinks that they're socially maladjusted. Why

1:02:12

would anybody be so interested in

1:02:14

spotting trains? I think everybody should

1:02:16

try to be a train spotter

1:02:18

in something that matters to them.

1:02:20

You know, like I'll, I'll talk

1:02:23

about what makes a great startup.

1:02:25

I'll talk your ear off and,

1:02:27

and, you know. Everybody around me,

1:02:29

like, hey, Maples, we're supposed to

1:02:31

be having a party here, we're

1:02:33

watching a football game, you don't

1:02:35

have to talk about these esoteric

1:02:38

details of a startup, nobody's heard

1:02:40

of. But I'm just that interested,

1:02:42

like I care that much. And

1:02:44

so, like, I encourage everybody to

1:02:46

have the broadworldly wisdom, but then

1:02:48

the tea of knowledge where they're

1:02:50

a trained spotter, and the advantage

1:02:52

to that is that, you know,

1:02:55

like I understood when Bitcoin came

1:02:57

out. I understood why a lot

1:02:59

of what's profound about it could

1:03:01

be understood by understanding equations of

1:03:03

heat and energy and conservation of

1:03:05

energy. And I understood that like

1:03:07

fiat currency does not have conservation

1:03:10

of monetary energy and that Bitcoin

1:03:12

does. And I knew that because

1:03:14

of that it was a superior

1:03:16

feedback loop system than any other

1:03:18

currency that existed. You wouldn't have

1:03:20

connected those dots, right? If you

1:03:22

hadn't spent time understanding, you know,

1:03:25

the equations that govern thermodynamics, but

1:03:27

you would have never known that

1:03:29

when you were studying it. You

1:03:31

just had to decide it was

1:03:33

worth your time to engage with

1:03:35

that topic because it was a

1:03:37

way to honor the gift of

1:03:40

your time and do your best.

1:03:42

Mike, I could talk to you

1:03:44

all day, man. I really appreciate

1:03:46

this. We definitely need to do

1:03:48

a round to the book. that

1:03:50

I highly highly recommend is called

1:03:52

pattern breakers why some startups change

1:03:55

the future. The reason why I

1:03:57

liked it, there's many reasons. One,

1:03:59

the guy who should write this book,

1:04:01

wrote this book, Mike Maples Jr. You're

1:04:03

the guy to write this book, but

1:04:05

also the combination of the fascinating stories.

1:04:07

And I don't think this is just

1:04:10

for people who are into the world

1:04:12

of startups or investing. I think this

1:04:14

is into people who care about humanity,

1:04:16

who are leaders. who care about excellence,

1:04:18

which is really the avatar of the

1:04:20

learning leader show, all about understanding excellence

1:04:22

and becoming a better leader and impacting

1:04:25

people in a positive way. And I

1:04:27

think that's what pattern breakers is all

1:04:29

about and that you poured, you could

1:04:31

tell your heart and soul and I

1:04:33

know you wrote it and rewrote it

1:04:35

multiple times. I talked to Sam about

1:04:38

that you weren't okay. to release just

1:04:40

a good book. It needed to be

1:04:42

excellent and that's what you done man.

1:04:44

So thank you for being here. Thank

1:04:46

you for writing pattern breakers and I

1:04:48

would love to continue our dialogue as

1:04:50

we both progress man. Cool. Thanks Ryan.

1:04:53

I really appreciate it. It was an

1:04:55

honor to be on your show. Some

1:04:57

of your guests are, I'm big fans

1:04:59

like Coach Stoops not long ago, huge

1:05:01

fans. So you know, it's an honor

1:05:03

to be included with that group of

1:05:05

people. Oh man. Thank you so much.

1:05:10

It is the end of the

1:05:12

podcast club. Thank you for being

1:05:14

a member of the end of

1:05:16

the podcast club If you are

1:05:18

send me a note Ryan at

1:05:20

learning leader.com Let me know where

1:05:23

you learned from this great conversation

1:05:25

with Mike Maples Junior a few

1:05:27

takeaways from my notes I loved

1:05:29

how Emotional Mike got when he

1:05:31

talked about his dad and if

1:05:33

you want to see it go

1:05:35

to youtube.com/Ryan Hawk you can see

1:05:37

the emotion Poring out of him

1:05:39

as he talked about his dad

1:05:42

and his message of do your

1:05:44

best There is only one you

1:05:46

and it comes from a place

1:05:48

of gratitude How will you decide

1:05:50

to spend the gift that is

1:05:52

your time? Don't waste it trying

1:05:54

to be someone else do your

1:05:56

best internalize what it means to

1:05:58

do your best avoid the trap

1:06:01

of memetic desire and copying others

1:06:03

and figure out how you can

1:06:05

make a positive dent in the

1:06:07

world. And then chance favors the

1:06:09

prepared mind. We are all visited

1:06:11

by luck, but most of us

1:06:13

don't answer the door. We need

1:06:15

to become a professional noticer. Again,

1:06:17

Mike's favorite. verb noticing most people

1:06:20

don't have prepared minds be intentional

1:06:22

about noticing the world around you

1:06:24

and being prepared for when luck

1:06:26

visit you. I love his story

1:06:28

about his chief of staff Sam

1:06:30

Baskin. Sam played basketball at Stanford

1:06:32

as well as other schools and

1:06:34

at Stanford the coaching staff would

1:06:36

hand them a sheet of paper

1:06:39

that had three keys to winning

1:06:41

the game. Just three. In another

1:06:43

school he played for they would

1:06:45

hand him a same sheet however

1:06:47

that would have 20. keys to

1:06:49

winning the game. Nobody remembered any

1:06:51

of the 20. Everyone remembered all

1:06:53

of the three. This is a

1:06:56

great metaphor for life. If you

1:06:58

try to value everything, you end

1:07:00

up valuing nothing. If you have

1:07:02

12 priorities, you have none. You

1:07:04

have to decide what are those

1:07:06

few things that absolutely must go

1:07:08

right in order for you to

1:07:10

win. And then focus. on those.

1:07:12

Once again I would say thank

1:07:15

you so much for continuing to

1:07:17

spread the message and telling a

1:07:19

friend or two, hey you should

1:07:21

listen to this episode of the

1:07:23

Learning Leader Show with Mike Maples

1:07:25

Jr. I think he'll help be

1:07:27

becoming more effective leader because you

1:07:29

continue to do that.