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Some. This podcast is for

2:00

informational purposes only and should not be

2:02

relied upon as a basis for investment

2:04

decisions. My

2:17

guest today is Syann Bannister. Syann's life

2:19

story is remarkable. She was homeless at

2:21

a young age, dropped out of high

2:23

school, and five years ago she suffered

2:25

an extremely rare stroke. Yet in

2:27

spite of all of this, she is one of the most

2:30

optimistic and curious people you can hope to meet. Syann

2:32

is also one of the great angel

2:34

investors of this era, having invested very

2:37

early in SpaceX, Uber, Postmates, DeepMind, just

2:39

to name a few. She

2:41

became the first female investing partner at Peter

2:43

Thiel's Founders Fund and now invests at Long

2:46

Journey Ventures. Our conversation is as

2:48

much about investing as it is about the

2:50

essence of life and how connecting with that

2:52

will help us in our professional pursuits. It's

2:54

also full of awesome stories about people and

2:57

companies like SpaceX and Bill Murray. Please

2:59

enjoy this fantastic conversation with Syann

3:01

Bannister. So

3:04

Syann, this is a hard one to know where

3:07

to begin, but since we were just talking beforehand,

3:09

you sort of gave me the perfect opening question.

3:11

Do you think that spirituality

3:13

is an investable

3:15

category for venture

3:18

investors? I absolutely think that spirituality

3:20

is an investable category and it's been

3:22

long overlooked. So I remember

3:24

when pray.com was raising and everybody

3:27

thought, who's going to actually use

3:29

this? Which target demographic actually

3:31

wants this? And I think

3:34

that there are a lot

3:36

of people, especially coming out of the pandemic, who

3:39

spent two years wondering

3:41

why is this happening to us?

3:44

What is this all about? Why

3:47

am I here? What is my purpose?

3:50

And then looking inwards

3:52

and then looking outwards. And I think

3:54

people are seeking these answers more than

3:56

ever before because when you

3:59

look online you read what's going

4:01

on in the world, it seems

4:03

like it's increasingly getting darker out there. I

4:06

would say that it's not, but this

4:08

is where spirituality comes in and lets people know

4:10

where the light is. I think

4:13

spirituality comes in many different ways. It comes

4:15

in the form of prayer, it comes in the form of meditation,

4:17

it also comes in the form of

4:20

potentially even psychedelic medicine. So

4:22

I do think that it's a hugely investable

4:24

category and you look at the success of Angel

4:27

Studios. Well, Angel Studios

4:29

basically crowdfunded

4:31

ticket sales as well as

4:33

the development of film and

4:36

it ended up being the best box office

4:38

film at the time and it

4:40

went completely out of a studio model. And

4:43

they basically put out this piece

4:45

of art that people were clamoring

4:47

for and the studios

4:49

themselves didn't think that it was an

4:52

investable category. How much

4:54

of your investing thinking does

4:56

the word contrarian describe?

4:58

How do you identify with that word related

5:01

to your investing strategy? Peter

5:03

always says, Peter Thiel says, you know, it's okay

5:05

to be contrarian, but you've got to be contrarian

5:08

and right. Being contrarian for

5:10

contrarian's sake is probably not a

5:13

good path to take, but people

5:15

have labeled me or claimed

5:17

me as contrarian. I

5:19

don't know that I would be self-described

5:22

as contrarian, but I

5:24

tend to think differently than other people do.

5:26

And so when I identify

5:28

an opportunity and I go out and

5:31

try to convince other people that I've

5:33

found an opportunity and they consistently

5:35

tell me, no, this isn't

5:38

going to work, which usually indicates

5:40

to me that I'm on to something. I

5:42

know something that no one else does. I'm

5:44

thinking in a different way than other people

5:46

are. And there is usually high

5:48

alpha there when you find these

5:50

secrets. Before you joined

5:53

Founders Fund, what did you see in

5:55

Peter and in them? And what do

5:57

you think they saw in you? Well,

6:01

I dropped out of high school. I did not

6:03

go to university. And so I always like to

6:05

joke that I went to Peter Thiel University. And

6:08

it was a dream come true for me.

6:10

I was working at AngelList at the time

6:12

I was an angel investor. I'd actively been

6:14

investing at that point for probably about

6:16

eight years. And when

6:19

they reached out to me and asked me to join them, three,

6:22

it was like a Cinderella story. I got

6:24

to go and work with people that I look up

6:27

to so much and be able to learn

6:29

from them and to

6:31

basically absorb knowledge every single

6:34

day. And they brought

6:36

me on to run their early stage efforts.

6:39

But as you know, Founders Fund became a

6:41

very large fund. And it

6:43

becomes increasingly difficult in a multi stage

6:45

fund to execute different strategies, especially at

6:47

the early stage. And so

6:50

they tried their best to help

6:52

me grow into the muscle of series

6:54

A, series B investing. And

6:57

they did everything they could to keep

6:59

me there. And I would have stayed

7:01

if we've been able to figure out probably some

7:03

sort of strategy that worked, because

7:06

I do love that team so much. Working

7:08

there was probably one of the best four

7:10

years of my life. How

7:12

would you sum up what you learned about

7:15

the difference between that early, early stage and

7:17

the slightly later stage that you tried to

7:19

make work? What is the phase change that

7:21

happens that makes your skill in

7:23

one not necessarily translate to skill in the other?

7:26

When you're an early stage investor,

7:29

you're very qualitative, not quantitative. And

7:31

I'm a qualitative investor. And that

7:34

becomes very difficult when you're trying to talk

7:36

to clients or people who think about a

7:38

world in data rooms and

7:40

spreadsheets and wanting an

7:43

answer to how you decided

7:45

that you want to invest in something because

7:47

you're trusting your gut or you've thought about

7:49

the world a certain way, or

7:51

you've been looking for this answer to appear in front

7:53

of you may look to

7:56

others as if you're impulses because

7:58

you want to move quickly. And

8:01

they want to be deliberate and want to get

8:03

in the data room and want to know more about the

8:05

company. And oftentimes at the early stages of

8:07

the business, you know very little. You know that you've got

8:09

a good founder in front of you, you know that they

8:11

have an idea and they have a shot. But

8:14

all of that data is not going to be there. And

8:17

so you've got two different types of

8:20

investor types of minds. And

8:23

that can be difficult to

8:25

navigate and frustrating.

8:29

And it was actually kind of soul-crushing for me. I

8:31

tend to like to be incredibly

8:34

optimistic. And usually when

8:36

you get into the quantitative realm of the world,

8:38

you're dealing with a lot more pessimism. And

8:41

so for me, I'm an intuitive

8:43

thinker. And I

8:45

think that if you're an intuitive

8:47

thinker and you have a sort of

8:49

a gut feeling about things, and you really

8:52

deeply think about the world, then

8:54

early stage is probably the best

8:56

avenue for you. So obviously at

8:59

the time when you joined, you

9:01

had a ridiculous seed investing track record.

9:04

We'll talk about some of those companies in a few

9:06

minutes. But if you had to abstract away the track

9:08

record, like the obvious evidence that you were good at

9:10

doing this, what do you think

9:12

Peter would have said before you joined about what

9:15

made you interesting and special relative to

9:17

say, you know, other people? I'm sure

9:19

Peter's reference class is pretty good. So

9:22

qualitatively what he have said, quantitatively you

9:24

were great. Peter gave

9:26

me one of the best pieces of feedback. One of

9:28

the things I love about Peter is he's so precise.

9:30

He can give you like an

9:32

amazing piece of feedback if you're willing to

9:34

listen to it and really digest it. And

9:37

he took me on a car ride one day. And

9:40

he simply said one sentence to

9:42

me, and it changed my life. And it

9:44

actually led to me quitting the firm. He

9:46

said, Sian, you're really good

9:48

at feeling, but you're not really good at knowing

9:51

yet. That was it. And

9:54

I looked at him and I understood exactly what he

9:56

was telling me. And

9:59

I marinated on it. it and marinated on it and

10:01

I said, do I really want to know? Do I

10:04

really want that skill set? Do

10:07

I really want to learn these

10:09

things that are so uncomfortable and unnatural

10:11

to me? And is this the right place

10:13

for me? And the answer was no. So

10:15

I think what Peter loved about me

10:17

and why he wanted me to join the team

10:19

is because I do have principles,

10:21

I do have a North Star, I

10:25

do make debt decisions very quickly. I think

10:28

that there was a world

10:30

where they had a carve out

10:32

of a seed stage fund and it was

10:34

a separate fund and it didn't conflict

10:36

with the main fund investments and this

10:39

probably would have worked out. I

10:41

think what he saw in me was someone

10:43

who thinks differently about the world. He

10:46

really loves to reward diversity

10:48

of ideas and backgrounds. I

10:51

think that people don't give them enough credit for that.

10:54

The fact that I'm a high school dropout, I didn't

10:56

go to university is a plus in

10:58

his mind. He wants to

11:00

work with investors who never wanted to be

11:02

investors. It's a wonderful way to sum

11:04

it up. So tell me about how

11:07

you think differently, what that North Star is, what

11:09

those principles are. I'd love to explore those in

11:11

turn. You can take them however you'd like. I

11:14

was homeless at a very young age and

11:16

I grew up very poor and I

11:19

always remember where I came from. And

11:22

so when I do investments, for example,

11:24

some of the investments I've made in

11:26

Postmates or Uber, I

11:28

always think about the younger me,

11:31

which is if I could have driven

11:33

an Uber or I could have delivered

11:35

a sandwich, that would

11:37

have been life-changing for me. And

11:40

I think a lot of the times when we're investors, we

11:42

live in a bubble, our lives

11:44

are relatively comfortable for the most

11:46

part and we lose track of what

11:49

the rest of the world's experience is.

11:52

Being able to have flexibility in your

11:54

income and in your work is

11:57

a dream come true for many,

11:59

many people. And so

12:01

my North Star is around ending

12:04

poverty, creating different

12:07

types of wealth categories and income

12:09

generating categories for people who didn't

12:11

have access to those in the past.

12:13

For example, Angelist, crowdfunding,

12:16

reg CF financing, things

12:19

like that are really interesting to me. And

12:22

if you look across my portfolio, that's not always

12:24

the case. Sometimes I'm just really interested in a

12:26

category and I want to invest in it. But

12:29

for the most part, I would say

12:31

that anytime someone comes to me and they say,

12:33

I have a new way for people to reach

12:36

a market and sell a product that

12:39

could be life changing for a small entrepreneur.

12:42

That's where I really, really, really like to play.

12:45

I think that some of the companies, while

12:48

vilified, like if you look at Uber and

12:50

you look at Postmates, they've been vilified

12:52

throughout time. It really,

12:54

really doesn't take into account that there's

12:57

people out there that are disabled. There's

12:59

people out there that have family on

13:01

hospice. There's people out there that have

13:03

children in daycare and

13:05

they need that flexibility. They need that

13:07

source of income. And

13:09

otherwise, they would have been locked into a nine to five

13:11

job with no flexibility, unable to

13:14

take care of their relatives, unable to

13:16

take care of their own medical needs.

13:19

And so I want to invest in

13:21

things that really

13:23

change and move the needle in people's

13:25

lives on a

13:28

grand, grand scale. And then I think

13:30

there's obviously venture returns in those opportunities,

13:32

but they also align with my North Star

13:34

and my core values. Are

13:37

there any other principles that you

13:39

think about often as you're making

13:41

a decision or as you're searching for things

13:43

that might interest you? Yeah,

13:46

I really like when a founder has

13:48

overcome some kind of adversity. So it's one of

13:50

the questions I ask, which is what

13:52

sort of adversity have you faced in your

13:54

life? And I'm not looking for

13:57

a story like mine. Adversity

13:59

comes in. in many, many ways. For example,

14:02

you might be a founder who grew up in

14:04

a family that expected you to become a

14:06

doctor or a lawyer. And maybe

14:09

they immigrated to America and they

14:11

know that that's a really good career for

14:13

you to have. And so they push you

14:16

hard to do those things. And then you

14:18

say, no, actually, I'm going to

14:20

go start something else. And I'm going to build this

14:22

company because I really

14:24

feel like it's the right thing to do.

14:26

And this is my calling. So answering a

14:28

call to adventure

14:31

against, you know, your

14:33

parents could be a form of

14:35

adversity. Maybe you went to the military

14:37

and you were deployed and

14:39

you had to overcome what you saw.

14:42

That's also interesting. Maybe you

14:46

were in Parkland and you were at the shooting

14:49

and you overcame that adversity. We

14:51

have founders who are coming out of those. And

14:54

I just really think it's remarkable

14:56

when they come out of one of these

14:58

experiences with a fresh set of

15:00

eyes and a new perspective on the world and

15:02

most importantly, hope. They're just like,

15:05

yeah, I had it rough or

15:07

I overcame this challenge, but

15:09

I'm so

15:11

excited about living. I'm so excited about

15:14

innovating. And I look

15:16

for those founders and I want to help them and I

15:18

want to be by their side because

15:21

when you build a company, you're going to be faced

15:24

with so many amazing challenges.

15:27

And if you can't overcome them all, if you

15:30

can't move past them, if you can't put your

15:32

ego aside and do what's

15:34

right for the company and always arrive at the

15:36

best answer, then you probably

15:38

won't succeed. How did

15:40

you emerge from what was a very difficult

15:43

childhood with hope and

15:46

optimism as key parts of

15:48

your philosophy? I've been thinking

15:50

about this a lot as I've been writing. And

15:52

I really honestly think that when you're

15:55

faced with the question of survival,

15:58

that was literally my question. I

16:01

was turned out onto the street when

16:03

I was 15 years old. I

16:05

didn't have a job. You have

16:08

to ask yourself, do you hunker

16:11

down and just say, this is it for me? Or

16:14

do you say, I've got

16:16

to turn over all the stones and see

16:18

where the opportunities are. I've got to

16:20

figure this out. I have to have hope. I

16:22

have to have faith that something's

16:24

going to work. And so I chose

16:26

to have faith and hope route every

16:29

time. And it

16:31

always worked out. It always

16:33

did. And I think that had

16:35

I gone the other direction and

16:37

just said, there's no hope. There's no

16:40

future. I can't do

16:42

this. The cards are stacked against

16:44

me. It's a self-fulfilling

16:46

prophecy. Was there a moment

16:49

when you first remember making

16:51

that explicit choice? Yeah,

16:53

it was in that moment. So I became a ward of

16:55

the state and they removed me

16:58

from my mother's house and they told me

17:00

I had 24 hours to find a home.

17:03

And I didn't have a home.

17:05

I didn't know where to get a home. They told me that

17:07

if I didn't find a home in 24 hours, they were going

17:09

to put me in a group home. I've

17:11

been in those group homes. And

17:14

I knew that that's not where I wanted to end

17:16

up. And so I just said, I looked up at

17:18

the sky and I said, please universe help me. And

17:21

I got an answer, which was I knew one

17:24

adult and I walked over to

17:26

her house and I said, can I live with you? And

17:29

she said, sure. Very

17:31

easily in that moment, I could have just sat

17:33

there and succumbed to sorrow, to

17:35

suffering, to all of

17:37

it. And because it

17:39

worked out, I just kept doing it. It

17:42

was one of those things where I was just like, you know what?

17:45

I had a stroke five years ago and I

17:47

was like, I'm going to do the same thing. I looked at it with

17:49

curiosity. I looked at it with wonder and

17:53

got through my stroke. I lost

17:55

my ability to walk, my ability to see. If

17:58

you look at everything with curiosity and wonder

18:00

and love and hope, you

18:02

can overcome a lot of things. And

18:04

I think that's what people don't realize is that

18:07

it takes a lot of bravery to be

18:09

optimistic. It's easy to be

18:11

pessimistic. It's easy to say that things won't work.

18:13

It's easy to say, I'm not

18:16

going to do that because then you don't have to muster

18:18

up the willpower. Sorry. What

18:20

is it like to look at something like a

18:22

stroke with wonder and curiosity? Like, yeah, I must

18:24

have to hear a description of that. And when

18:26

it happened, I just surrendered.

18:29

It was one of these things where I was

18:31

just like, I have no control over this situation.

18:34

I have to trust that the medical doctors

18:37

that are coming to me that are

18:39

the best there is at UCSF

18:41

hospital are going to do what's right. And

18:44

all I have to do is sit

18:46

here and try to maintain my calm and try

18:48

to find all the joy in

18:50

all of it. And so like

18:52

when the students were coming and sticking lights

18:55

in my eyes and lining up down the hallway

18:57

because they'd never seen an edema in an eye

18:59

before, I was like, yeah,

19:01

line up. Come look, come look. Everybody come look.

19:03

I've got diamonds in my eyes. Come. Like it's

19:06

obviously precious. You want to see it. Every

19:08

time I did an MRI, I found it joyful. Every

19:10

time I had to do a blood draw, I

19:13

would just sit there and know that

19:15

I was contributing to medical science because

19:17

my stroke was one in 5 million a

19:19

year. It was even rarer than that because

19:21

I was young. So

19:24

it's one of these things where you

19:27

could either just say like, this is it, I'm going to die

19:29

and cry. Or you

19:31

just say like, you know what, what is these

19:34

are my last moments. I may as well make the

19:36

best of them. So I did. And

19:39

I honestly believe, granted, I can't prove

19:41

it, but I believe that that's what

19:43

helped and aided in my recovery and why I

19:45

recovered so quickly. Why do

19:47

you think that probably for those listening,

19:50

like it is for me, it's so hard to

19:52

imagine, much less

19:54

pull off the feeling of curiosity

19:56

and wonder in the face of such adversity. I

19:59

think everyone listening would. I always say, yeah, this is

20:01

a very rare perspective

20:03

we're hearing. And I

20:05

don't think I'd be able to pull that off. So why is it

20:07

so rare? Do you think? Why

20:09

is it so rare? I think we've lost

20:11

touch with our child minds inside

20:14

of us as a child yearning

20:16

to be free. That's cosplaying

20:18

as an adult. I think

20:21

we over time build our

20:23

personality. We get told what we can and

20:25

can't do. We wear

20:27

certain clothes. In

20:29

terms of people in their aug, this is going to be amazing. There's

20:33

hundreds and thousands of people out there, some people are going

20:35

to be coaching me. So, um, you

20:38

think about just the people

20:57

who are not made up. And children, when you

20:59

show them a four leaf clover and the

21:02

pattern of a four leaf clover, find them within

21:04

like 20 seconds. They're

21:06

able to find them because their mind is

21:08

not clouded with all of this, frankly,

21:13

garbage that we grownups carry

21:15

around with us. And

21:17

so for me, I'm constantly looking to

21:20

reconnect with my child self, with the

21:22

spirit that's inside of me, that

21:24

yearns to be free, that yearns to learn

21:26

about everything. I think a lot

21:28

of people take for granted what's around

21:30

them. They think they've got it all figured out.

21:33

There's like, there's nothing new to learn even

21:35

about maybe your bedroom. But

21:38

if you look around with curiosity about your bedroom,

21:40

I bet you with a new set of perspectives

21:43

could see your room in a whole different way. You

21:45

could see your backyard in a whole different way. You

21:47

could see your friendships in a whole different way. I

21:50

just don't think a lot of people understand

21:53

that that curiosity is inside of each one

21:55

of us. So it's really about

21:57

allowing yourself to be silly, allowing yourself to be

21:59

silly. yourself to relax

22:04

more, be comfortable with who

22:06

you are and let who that person is

22:08

out. I think we

22:10

are really, really afraid of that authenticity

22:12

that's inside of us and how

22:14

people might judge us. Like

22:16

I said, if we dressed up like SpongeBob and came to work.

22:19

I'm reminded of my favorite room equal,

22:21

which is take off your mask. Your

22:24

face is glorious. That's

22:26

right. That's right. That's exactly

22:28

right. If you actually think about

22:30

what you are, we are

22:32

an animal. When

22:35

we die, we decompose and

22:37

we become dirt. So

22:40

what else are we? All of

22:42

this is just an avatar, but

22:45

there's something inside of us that yearns

22:47

to be created, that yearns to build

22:49

things, that yearns to change the world

22:52

that wants to have

22:54

a purpose for being here. And we deny

22:56

that spirit, its existence every day.

22:59

I am guilty of this. Everyone's guilty of this.

23:02

You spend time with children and

23:04

you spend time with dogs and you go out in nature and

23:08

you bathe in nature. You start to realize

23:10

the things that truly matter. Like when I came

23:12

out of the hospital after having my stroke, I fell to

23:14

my knees because of the air. When

23:19

the air hit my lungs and I was

23:21

like, whoa, what if I never got

23:23

to breathe that again? How magnificent. The

23:26

sun was on my face and I

23:29

was like, how splendid. That's what truly matters in

23:31

the world. Like

23:33

we make up all of these stories inside

23:36

of our heads about what's important. But

23:40

what's really, really important is remembering

23:43

just how precious life is and

23:47

how we have a place to live.

23:51

And how we have a short amount of time

23:53

to accomplish all of our dreams. And

23:57

they're all accomplishable. Really

24:00

really hope that. When. People listen

24:02

to this. They try to figure

24:04

out how to tap into that

24:06

created serious side because I'm endlessly

24:08

curious. My biggest. Complaint. Is

24:10

there's not a thousand of me than on that scale? It

24:12

will. I. Would love to have. Multiple

24:15

Fi and agents out there roaming the

24:17

world's. Bridge. To require. Yeah,

24:19

we'd be Philo learning as much as

24:21

they possibly can. Super. Mean:

24:23

my appetite for knowledge and

24:26

for. Everything. Is insatiable.

24:29

Subway. Map some of this back

24:31

to peers amazing one liner to

24:33

you. And begin on that

24:35

notion of your skill ceiling. When.

24:38

The feeling is as signaling to

24:40

buys when you meet with a

24:42

very young company and sounder. Maybe.

24:45

Describe what that's like. Is it

24:47

the recognition of someone that seated

24:49

they're calling? Is it. Something.

24:51

About the person like. Walk.

24:53

Me through the I'm sure feeling is hard

24:56

to describe but as best you can wow

24:58

How would you describe that skill of feeling.

25:00

That. Peter pointed out and you. If

25:03

you think about his business is just art. The.

25:05

Us Constitution. As a piece

25:07

of art, money is art. Contracts are

25:10

arts coed as Arts. So.

25:12

The art of storytelling is art. So when someone's in

25:14

front of you and they're getting the pitch, they're telling

25:17

you a story about who they are and what they

25:19

want to built. So. Immediately

25:21

Amazon will thinker. And.

25:23

I start spinning up a universe and my

25:25

mind. Of what they're trying

25:27

to build. Ideally. I've

25:29

already thought about what they're trying to build. As.

25:32

A dream mean. By sitting around

25:34

and immersing myself and the world's. I.

25:37

Go to strange conventions that. Most.

25:40

Of my colleagues will be like why on earth are

25:42

you spending time at these places. That's

25:44

why I'm doing is trying to

25:46

immerse myself among the general population

25:48

of people. And trying to figure

25:50

out what their problem points are. For example,

25:52

going to lay. Mining Convention.

25:55

Not. Bitcoin by actual heavy

25:57

equipment. And. Seen like none of these.

26:00

People that are moving the earth Thinking about

26:02

going to a toilet paper convention? I

26:04

was curious like everybody during the kingdom at

26:07

random bought toilet paper. Why? Did

26:09

we have a shortage? I'm gonna go to the toilet paper. Convention

26:11

and find out. Things. Like

26:13

that and. I just think that when

26:16

a person sitting in front of me and they're giving

26:18

me the pitch. I start daydreaming and

26:20

I start seeing the truth of what

26:22

they're telling me. And advice Feel

26:24

it. Than the feeling I called my lightning

26:27

bolt. Is literally feels like a

26:29

jolt of energy. And my body. And.

26:31

I feel like a tingle and it's like school. There's.

26:34

Something here in there, something novel here, and

26:36

or something different, but I haven't seen. And.

26:38

Then I try to figure out what is different about

26:40

it is that the person is that the opportunity is

26:43

it The. Tiny. Has.

26:45

Someone tried this before and failed. Why?

26:48

Is this person potentially the right

26:50

person? etc. And so.

26:52

Sometimes. It's so overwhelming, that and dislike.

26:55

I've written checks on the spot. Because

26:57

it's like one of these things, right to still arrested

26:59

by it. And. Sometimes.

27:02

I go and marinate on it and chew on it

27:04

for. Twenty four hours and if I still

27:06

feel the same feelings than I make the investment.

27:09

By. In general, it's

27:11

this weird intuition. That

27:14

this person is on says something. And

27:16

it could be beg. For example, whistle

27:18

a cookie mon go my insect. Fails.

27:20

Go out for an example. So perfect. Yeah,

27:23

And I went to work. I was working

27:25

at Angeles at the time and I was

27:27

showing everybody their previous game congress. And

27:29

I was playing it and trying to explain to them about.

27:31

How this world would be risk and. And.

27:33

Instead of these portals that I was playing

27:35

at, There would be these cookies thoughts And then

27:38

there's going to be Pokey. Mon around and everybody's

27:40

like you're insane. What are you talking

27:42

about? And I should see it clear

27:44

as day, but I couldn't understand why no one

27:46

else could. And when I go

27:48

out and start trying to explain this

27:50

dream the people that visualization that I

27:52

see and they continuously can't see it.

27:55

And they came up with excuse after excuse not to

27:57

invest in it. which was like. Nintendo.

28:00

is a corporate investor, I don't do investing

28:02

with corporate investors. These guys are

28:05

spinning out of Google, do they really have

28:07

grit? It was excuse after

28:09

excuse after excuse. I was

28:11

just like, you don't understand these people built Google

28:13

Earth, they really understand mapping. And then the other

28:15

thing was the insight that I had was that

28:18

company was ultimately a mapping company,

28:20

not a gaming company. And trying

28:22

to convince people of that, they're like, well, they only

28:24

look at the bird in hand. They're just like, well,

28:26

it doesn't look like that right now. So not

28:29

interested. And so I think that

28:31

that's how my mind is different. And how

28:34

I arrive at these decisions is I just

28:36

really, really trust. And I really don't

28:38

care if people don't believe me, or think

28:40

I'm crazy, or stupid, or

28:42

any of those things. And so for me,

28:44

I don't have those kinds of fears that

28:47

some people have. As a matter

28:49

of fact, the more they disagree with me, it's

28:51

almost like I feel like it's the same.

28:53

I'm like, huh, that's interesting. Or I

28:55

look at the argument, and I try to see if

28:58

it has merit. Like I said,

29:00

don't be contrarian for contrarian's sake. If somebody's

29:02

coming to you and they have a really

29:04

good argument, they can talk me

29:06

out of things, for sure. Maybe it's something

29:08

that I didn't see. But sometimes

29:11

I weigh that piece of advice. And I'm

29:13

like, hmm, I still think that

29:15

they can overcome that hurdle. John Greenewald I

29:17

mean, it makes perfect sense to me that you're

29:19

not going to get unusually good results by doing

29:22

the same thing other people do. So the Toilet

29:24

Paper Convention makes lots of sense to me. Do

29:26

you have a favorite example of some unique

29:29

input like that, leading

29:32

to an investment that

29:34

you made? Elizabetham Ober.

29:38

I lived in a hotel for a period of time, it

29:40

was a nice hotel in San Francisco. And the

29:43

front desk would arrange cars for me to get

29:45

to the airport. And this was before Uber

29:48

was even a thing. And so

29:50

there was this livery driver that was my

29:53

livery driver. And I

29:55

really took a liking to him. So I got his card and I

29:57

said, why don't I just start booking you directly. And I

30:00

The great with you. You're. Just

30:02

an amazing person. He was a immigrant

30:04

from Brazil. And just a really good

30:06

driver. and just I'd really like talking with him in the

30:08

car. One day I was going

30:10

to the airport and she says you know I'm

30:12

not an investor cyan but if I was. I

30:15

would invest in this thing called Goober Town that he heard

30:17

of it. And. I said no,

30:19

I haven't. And He said, well.

30:22

I'm the only guy. A.

30:26

Scam. Worked in I said. Okay,

30:29

so they're paying you by the hour

30:31

to drive around and pick up people

30:33

who are texting some phone number. Keep

30:35

in mind there was no app at that time. it's just

30:37

a phone number. And. You

30:40

show up and he's like yes and I

30:42

said ha. Will. Let me know

30:44

when they're not paying you by the hour anymore.

30:47

And. The reason why I said

30:49

that was. Four. Years prior.

30:52

I was thinking about how. Why

30:54

is it that I go out and I try to

30:56

hail a taxi? And. I can't get

30:59

one, especially if it's raining. Or.

31:01

Of there's a big conference going on. you think that

31:03

there be more cast is that would come online to

31:05

meet the market demand. So. I started. Talking

31:08

to taxi drivers about. When.

31:10

You go get your car. What's the first thing

31:12

that happens? And. They say will I have to

31:14

pay. One. Hundred hundred fifty dollars just

31:17

to get the card of leave the yard. So.

31:19

They're already in the whole hundred and fifty dollars

31:21

rate. So. They're out there hustling trying to

31:23

get that hundred fifty dollars back to so they can

31:25

be in the money. So. There's

31:28

zooming around like crazy, acting like. The.

31:30

Survey says I get a taxi and they

31:32

drive superfast. Well that's why they drive super fast as

31:34

are trying to get to the next there in the next

31:36

year in the next year. So. That

31:38

you become a taxi driver and they

31:40

explained the medallion. System. To me. And.

31:43

I was like wow, what a racket that

31:45

is. Definitely seems like a protectionist racket. So.

31:49

Go. Back to the driver that I'm in

31:51

the car with. This. Is a

31:53

livery driver. It's not a taxi they are. regulated

31:56

by tcp licensing which means they have

31:58

to be drug tested And

32:01

they have to go through proof of insurance and all sorts

32:03

of things like that in order to be a livery driver.

32:06

So they started with those for a reason. And

32:10

that was the first vision. A

32:12

lot of people, the first objection I heard

32:14

about investing in that company was not

32:16

everybody can afford a black car. And

32:18

I said, well, that's a short-term vision.

32:21

The long-term vision is that everybody's

32:23

car becomes available and

32:25

comes online to drive. And I said, well,

32:27

strangers won't get in strangers' cars.

32:30

And I'm like, what'd they do all the time? They get in a taxi.

32:33

You don't know that person, and that person doesn't even own that car.

32:36

So he gives me Ryan Graves'

32:38

business card, and he says, call Ryan Graves. And

32:40

I look at the business card, and the phone

32:42

number I think was in Chicago or something. And

32:44

at the time, I had

32:46

a pretty strict rule

32:48

about only investing kind of in

32:51

my backyard. Because every

32:53

time I tried to invest outside of

32:55

my ecosystem, I got hosed. I

32:58

didn't know the players in New York or

33:00

the players in Austin or Europe. And

33:03

I couldn't get follow-on financing for the companies.

33:05

That's all changed, especially since the pandemic, and

33:07

people have become remote. But

33:10

then I was just like, ah, so I put Ryan

33:12

Graves' card away. Fast forward,

33:14

David Kornick has this amazing event

33:16

called The Lobby. I

33:19

went to it, and basically, The Lobby

33:21

is based around the fact that most amazing

33:23

conversations happen in the lobby of the hotel.

33:26

It's not the content. It's not any

33:29

of it other than that. And it's

33:31

absolutely true. And it also happened in

33:33

the swimming pool and the hot tub

33:35

and the various things when you're

33:37

offsite at a resort that happen. Like

33:39

you go snorkeling together. You go swimming together.

33:42

So a huge group of us were in a hot

33:44

tub. And there's this

33:46

guy, Travis Kalanick, in the hot tub. And

33:49

he had just exited from Red

33:51

Swoosh, and he basically announced to everybody

33:53

he was on the bench looking for

33:55

his next thing. As

33:58

an investor, you always pay attention when someone else is on the bench. somebody

34:00

says something like that. We trade

34:02

on secrets. So I took

34:04

stock of this personality and his personality

34:06

was very alpha. It was very aggressive.

34:09

You could tell that everybody sort of quieted down

34:11

when he spoke. There's a lot of things

34:14

you look for in a leader and I

34:16

noticed that. And so I thought, well, I'm just gonna

34:18

watch this guy and see what happens. So

34:20

a few months later, I got invited to Open

34:22

Angel Forum, which is a thing that Jason Calcanis

34:25

did for a while. And

34:28

I'm sitting there and like the

34:30

second presentation that comes up is

34:32

Travis Kalanick presenting UberCab. And

34:34

I wrote to my husband and I said, we need

34:37

to invest in UberCab like today, right

34:39

now. I don't understand what's

34:42

going on with Ryan Graves, but it's kind of

34:44

irrelevant. And we didn't eat

34:46

Ryan Graves and we loved him. But

34:48

we knew, or at least I knew that Ryan

34:51

Graves would step aside with a person like that.

34:54

That's gonna want to be the CEO or Ryan would

34:56

even recognize he was the natural fit for it. I'm

34:58

not sure what happened on the back end, but

35:01

Ryan did step aside. He became the

35:03

COO and the rest is history. And so

35:06

there's an example of just being really

35:08

curious and following the

35:11

white rabbit, so to speak, down the rabbit

35:13

hole. You take that curiosity and you see

35:15

where it goes. And then

35:17

you strike the moment you have that lightning bolt. The

35:19

lightning bolt hit me when Travis got up. Yeah,

35:22

fascinating. So what price did you

35:24

end up investing in Uber at?

35:27

I believe that one's eight million. Eight

35:29

million? That's the first round. So that one worked okay

35:31

for you. Tell me the second half of

35:33

the story. What is it like to

35:36

be an investor and to hold on

35:39

to a business that ends up being, I think it

35:41

just hit an all time high yesterday or something. Tell

35:44

me about what that part of this is

35:46

like. So there's the decision. And I remember

35:48

talking to some of the early Bitcoin people that made

35:50

the most money in Bitcoin. And one of the things

35:52

that they had in common was that they were often

35:54

already rich because once something

35:56

10 or 100X is the pressure

35:58

to sell something. can be pretty high

36:01

and then the thing ends up 10,000 X-ing

36:03

or whatever. So I would love to hear

36:05

that side of this same story.

36:07

You bought it, you're in an unbelievable

36:09

price in a generational company, then

36:12

what? What was it like to watch,

36:14

to hold, to engage with the company

36:17

once you had invested? There's this beautiful

36:19

period when the company is small and

36:21

you can send emails to the CEO

36:23

and they respond and

36:25

that's usually when they're under 100

36:27

employees and then that disappears. And

36:30

it's natural. Every angel investor, every early

36:32

seed stage investor should understand that this could happen.

36:35

Travis becomes more unreachable, Emil

36:37

becomes more unreachable because you're

36:39

not their most important problem of the

36:42

day. They're fighting so many fires and it's

36:44

not because they don't like you or love

36:46

you or aren't even thankful for that first

36:48

investment, it's because they've got to run a

36:50

company. And so there's this period

36:52

after 100 employees that they

36:55

lean on you a lot less. That's

36:57

where you kind of just sort of surrender to

37:00

the big players that are going to write

37:03

the checks and hope for the

37:05

best outcome. There's very little you can do. You

37:07

know, in the case of Uber, Chris Saka got

37:09

involved very early. He rolled

37:11

up his sleeves and he actually showed up to

37:14

board meetings, to planning sessions

37:17

and they saw a lot of utility in that.

37:19

And so that's one way that you could stay

37:21

connected to the business. For me,

37:23

that's not my style. I tend

37:25

to like to be somebody's backbone and

37:28

they call me whenever they need a door

37:30

opened or they need something fixed or they

37:33

want my particular type of advice. The

37:36

uncomfortable part happens when the company does

37:38

really, really well and then

37:40

suddenly everybody starts speculating about your

37:42

personal wealth and starts telling you

37:44

what you should do with it. And

37:47

you start getting written up in articles

37:49

and your privacy starts getting

37:51

invaded and that can

37:53

be pretty daunting. That happened for a

37:55

period of time. And then of course, when they

37:58

go public, there's a lot of people that are not going to be able the

38:00

holding period. And did you hold it

38:02

this whole time? Like, were you still holding your original investment

38:04

when it went public? Yes.

38:06

Yes. I actually think that

38:09

it's best psychologically for

38:11

people to not

38:14

think about specific outcomes, to

38:16

set it and forget it literally, to

38:18

say, I will be pleased

38:20

with whatever happens, because that

38:23

needle is going to move all over the

38:25

place. There were times that we thought

38:27

that our shares would be worth something and then the

38:29

next day they're not. You're in

38:31

for a wild ride at that

38:33

stage. And so, I just

38:37

think you shouldn't become too attached to it.

38:39

And you should just come

38:41

up with a plan for why did you do

38:43

this in the first place? And what

38:45

are you going to do with that money once you have it? So,

38:49

this is something I always try to

38:51

advise my partners and anyone in the

38:53

investing spaces, why do what we

38:55

do if it doesn't serve a higher purpose

38:57

or higher power? So,

39:01

if you are lucky enough to

39:03

have an exit of any

39:06

material means to you and

39:08

your family, I think it's

39:10

really, really important to align it with your

39:12

North Star, whatever it is. You know, you

39:14

see Warren Buffett do this, you see the

39:16

most amazing people

39:19

in the world, finite worth individuals

39:22

who figure out charitable causes to

39:24

support or how to align their

39:26

investing by starting a fund and

39:29

getting institutions that they believe in alongside

39:31

them. So, that every

39:33

dollar you write, you maximize that

39:35

dollar. You're solving cancer research or

39:38

you're helping kids go to school or you're

39:40

helping a pension fund, then

39:42

you're actually really making a dent

39:45

in the world through capitalism. And

39:47

I think capitalism

39:49

has like such a, I don't

39:51

know, people use it like a dirty word.

39:54

And I think it's one of the most beautiful

39:57

concepts in the world But

40:00

we have to protect because

40:02

it absolutely can move

40:05

the needle in innovation and change

40:07

things on multiple levels. What

40:09

is beautiful about capitalism too? Let me

40:11

go back to it's my first time experiencing it.

40:15

So when I was younger,

40:17

I actually felt that business people were

40:20

evil and they were exploitative

40:22

and all sorts of things. And I'm sure

40:25

there are business people who are those things.

40:28

But when I listed myself up off

40:30

the streets, it was by selling necklaces

40:32

and making t-shirts. So

40:35

I realized I could scrape

40:37

up a little bit of money, I could

40:39

make a thing and a person out

40:41

there could buy that thing from me, had

40:43

a markup and then I could

40:45

reinvest that into more supplies

40:47

and make more money and literally

40:50

get off the street. And

40:52

to me that was like, whoa, wow. Why

40:56

can't everybody do this? Why can't they see this? And

40:59

instead what they see is various

41:02

abuses of capitalism. Capitalism itself

41:04

isn't just an idea, it's art. Art

41:07

can be abused. All things can be abused. But

41:11

at its core fundamental principles,

41:13

it's extraordinarily liberating. To

41:16

zoom to the maybe extreme

41:18

outcome of what a capitalist

41:20

system allows for, your story would be remarkable if

41:22

it was only Uber and nothing else. But maybe

41:24

you can tell the SpaceX story. Oh

41:27

yeah, the SpaceX story is a good one. So

41:29

I worked at a

41:31

company called Ironport and

41:33

I was employee number 30 and it's

41:36

the best company besides founder's fund I've ever

41:38

worked at in my life. The

41:40

CEO there was incredible. His name is Scott

41:42

Weiss and he built

41:46

a true meritocracy of the culture. It

41:48

was the first place that I went to that I felt

41:51

really valued for my mind above

41:53

all else. And

41:55

every time that they gave me a raise, instead of asking

41:57

for money, I asked for more equity. because

42:00

I believed so much in this company. And

42:02

so I was just like, give me more, give me more

42:04

equity, that's all I want. I'll figure out a way to

42:07

make ends meet otherwise.

42:10

And because before that I worked at many

42:12

startups and the equity didn't turn into

42:14

anything, every one of those

42:16

companies ultimately failed. So

42:18

when I had my first financial windfall was

42:21

because Ironport sold to Cisco for

42:23

$830 million, I think it was 2007. I

42:27

looked around to my phones and I was

42:29

very fortunate to have made phones that were

42:32

angel investors already. And my husband was

42:34

an angel investor, had already

42:37

been doing angel investments for 10 years. And

42:39

he said, obviously building a company is one

42:42

way to create wealth. And he

42:44

said, but the real way that I make my money is by

42:46

putting capital into high-risk

42:48

startups. He's like, why don't you do

42:50

that? And I was like, okay.

42:52

And he said, well, why don't you go out and look

42:54

for opportunities, see what resonates

42:56

with you and come back. So

42:59

I did. And I

43:02

was very, very uncertain and very, very

43:04

scared to put the money that I'd

43:06

slept under my desk for into

43:09

startups. But then Luke Noset came over to

43:11

our house who is

43:13

a dear friend of my husband's. They went to college

43:15

together. They dropped out of college together and drove

43:18

west with walkie talkies because

43:20

they didn't have cell phones and

43:22

got an apartment next to each other. Eventually

43:24

Max Lupton moved next door. But

43:27

he came over and practically got on

43:29

his knees and begged us for money

43:31

for SpaceX. And

43:34

it was his conviction and his belief

43:36

in Elon Musk, this

43:38

love that's indescribable.

43:41

This man is going to achieve this vision.

43:44

And then I went and talked to some NASA engineers and

43:46

they said, what he's doing is solid. And

43:49

the narrative violation there was a

43:53

private entity can't enter

43:55

the space realm,

43:57

period the end. This is NASA. in

44:00

the story the government will never allow him to

44:02

participate. I put money in, I was

44:04

like, you know what, I'm just going to put everything in it. Everything

44:07

I made for my arm port, I put in the SpaceX. And

44:10

I was like, you know, I'm young,

44:12

I can do this. I

44:16

can make the money again, I can always

44:18

join another startup. I can

44:20

always figure out something else. I definitely had built

44:22

myself a safety net, so I

44:24

could take that risk finally. So

44:27

I did that and it'll probably end

44:29

up being bigger than Uber

44:31

by far. When you think

44:33

back on these stories, are there lessons

44:35

that you pull from them or

44:38

do you just view them as sort of like crazy

44:40

things that happened? I mean,

44:43

the fact that you put all your money in

44:45

SpaceX is crazy. I imagine, I don't know what

44:47

the intervaluation was there, but I

44:49

know what the current SpaceX valuation is. You

44:51

can kind of figure out they've just blown up

44:53

a rocket on Launchpad and they haven't figured that

44:55

out yet and that can give you an idea

44:57

of timing. Yes, it's. I

45:00

haven't done that in a long time. So

45:02

I feel lucky, but I also

45:04

feel like it's because what

45:06

I do with the money, I'm

45:09

going to go back to spirituality, that

45:11

the universe tends to direct energy

45:15

in places where people

45:17

are doing good things with it. So

45:20

I think if I started doing bad things with

45:22

it, my chances of

45:24

luck diminish. I

45:26

think the fact that I have a North Star and

45:29

so does my husband and we believe in

45:31

things like freedom, the

45:33

US Constitution, we believe

45:35

in people being able to

45:38

start businesses for

45:40

ideas to flourish. I think these things

45:42

are very important core values of ours

45:45

and it's possible that

45:48

we are rewarded as such. Now, obviously, I

45:50

can't prove it, but

45:53

I really, really believe that

45:55

I am a steward of capital that doesn't belong to

45:58

me. It is mind-departing. boy

46:00

judiciously, but is

46:03

mine to basically put into innovation

46:05

and into nonprofit work, to

46:07

move the needle on this

46:10

earth to make everybody's

46:12

lives better ultimately in the end. And

46:16

I believe that as long as I continue

46:18

to hold that hope and

46:20

I trust my gut feeling, which I believe is

46:22

kind of divine, my ego is

46:24

a side. Like it's one of these things where I

46:27

don't even think that I'm responsible for

46:29

some of this. I don't know if

46:31

you've read the Rick Rubin book. I compared

46:33

myself to Rick Rubin online and I got a lot of

46:36

backlash and it was funny to me because Rick

46:38

Rubin is very, very similar to me because

46:41

we trust these

46:44

feelings that we have to make decisions.

46:47

And for him, it's like, I found

46:49

the Beastie Boys and no one's ever heard the Beastie Boys

46:51

and they're gonna love this. And I

46:53

know I'm on to something. And for me, Travis

46:55

Kalanick is the Beastie Boys. It's

46:57

totally fascinating. It's also a good excuse to

46:59

go back to what we started the conversation

47:01

with around spirituality. How did you get into

47:04

this? So now that I understand these

47:06

sort of like following the white rabbit holes

47:08

that you go down, what

47:10

is this rabbit hole? And I don't know if you've made investments

47:12

in this space or not. If you have, I'd love to hear

47:15

how and why and what, but

47:17

first tell us the journey that

47:20

you've been on, the learning journey that

47:22

you've been on. These are the ones

47:24

that you've been described in this specific field of spirituality. Because

47:26

if I'm not mistaken, a couple years ago, you were an

47:28

atheist and maybe that's different now, but I would just love

47:30

to hear the arc of that story. Yeah.

47:33

So a few years ago, I was an

47:35

atheist and like many people during the pandemic,

47:37

I had a lot of free time to

47:39

sit and reflect on, I

47:41

mean, some people, I hate to say that some

47:43

people didn't have the time because they were obviously frontline

47:45

responders, but I was fortunate enough

47:47

to sit down and think like, why is this happening?

47:49

Who am I? What is my place in the world?

47:53

And really, really figure

47:56

out the why, because

47:58

for a long time, I've really So like we're supposed

48:00

to just be good people, live

48:02

a good life and make the best of it and we just

48:05

turn to dust in the end

48:08

and that's all there is to it. But

48:10

the one thing I never tried was

48:13

believing. I never tried actually

48:15

having faith. You might ask

48:17

yourself, how does one try? It's not trivial. Like

48:19

you can't just say, today I try having faith.

48:22

I actually had to figure out how to

48:24

truly believe that the world is magical. And

48:28

the moment that I truly believed

48:30

that the world was magical, then the world

48:32

became magical. It

48:35

rocks the foundation of who I am. So

48:37

I had a spiritual awakening and

48:40

it's the only way I can describe it and I can tell you

48:42

that each one of us is walking

48:44

a very thin razor's edge between sanity and

48:47

insanity at all times. Serotonin

48:50

regulates a lot of

48:52

how we perceive reality. I

48:54

had a surge of serotonin in

48:57

this lightning bolt like no other. It was basically this

48:59

surge of energy that went from the base of my

49:01

spine at the top of my skull and

49:04

suddenly everything in the world looked different. Everything.

49:08

I started viewing signs differently.

49:11

I started viewing art differently, conversations

49:13

I was having with people differently

49:16

and I realized everything

49:19

around us is a projection

49:22

of our perception minds.

49:25

When we're born, when we are born, we

49:27

come online with like going back to parts work

49:29

and things like that. But when we're born, we

49:32

come online with about four distinct systems

49:35

that come online and then

49:37

through stimulus of interacting in the

49:40

world, we develop a personality

49:43

and we think this personality is fixed. We

49:45

think it can't be changed but

49:48

it turns out it absolutely can be changed.

49:50

Many parts of it can. How

49:52

I had the spiritual awakening was

49:55

the realization that all the

49:57

trauma in my past was a

49:59

construct of my imagination. That

50:01

basically, yeah, it happened. But

50:04

it happened like a dream happened, like a nightmare.

50:06

A nightmare you wake up

50:08

from and it's gone and you're relieved. You're like,

50:10

oh, that was just a dream. What

50:13

turns out trauma is also just a dream. Because

50:15

if you can overcome it and you can get past it

50:17

and you can move forward, you have

50:20

to realize that that thing when you spin

50:22

it up in your mind creates all

50:24

kinds of hormones that get released

50:27

that shape your reality and how you see

50:29

the world. We forget

50:31

that we're an animal that has hormones

50:33

and a mind. And

50:36

then there's this really special thing called consciousness.

50:39

And so I believe that

50:41

consciousness is kind of

50:44

like an operating system. And

50:47

it brings these parts of us

50:49

online that benefited us at one point

50:51

that no longer benefit us. Because

50:54

they have jobs, I think of them as kind of

50:56

like processes that come online to assist

50:58

you. They're like cron jobs and they're like, I'm here

51:00

to assist you. And we don't

51:03

know to put them away and tell them that they don't have

51:05

that job anymore. They don't need to do that

51:07

anymore. So once

51:10

I let go of this huge amount of trauma

51:12

and I realized that it

51:14

just didn't matter that

51:16

these things happened to me in the past, what

51:19

matters is literally right now. And

51:22

you hear people say this and

51:24

you wonder what does it mean when they

51:26

say this? And I always wondered

51:28

it. I was like, what does it mean? When

51:31

you have the true realization, it's almost like it's

51:34

written in your DNA, what

51:36

that really, really means. Then

51:38

you start to let go of so much.

51:41

And when you let go, all

51:43

of a sudden, you realize, oh,

51:45

life isn't so hard. It's actually

51:47

quite easy. And I just have to

51:50

trust myself and I have to trust my intuition.

51:52

And I have to just be.

51:56

And once you learn how just to be,

51:58

life gets a lot more simple. of

52:00

a sudden everything you ever wished for in your

52:03

life just starts coming true. It becomes

52:05

effortless. It's really weird. It's

52:08

really super weird and the only

52:10

thing that changed in my life was having faith in

52:13

something higher than myself. That

52:15

was it. This is why when

52:18

you ask me like what sort of insight

52:20

or brilliance or whatever led to whatever, it's

52:22

too easy for our ego mind to take

52:24

credit for everything. Something

52:26

gave me that feeling that

52:29

said you ought to

52:31

go deeper into this. You ought to do this. You've got

52:33

to take this risk. You've got to jump right now. I

52:36

guarantee you, if you talk to a lot of different people,

52:38

they'll say, I don't know why I did this. I just

52:40

had a feeling and I

52:43

now believe thoroughly in that feeling and I

52:45

believe that that feeling is the

52:47

universe or God, whatever word you want to

52:49

put into it and

52:51

it helps guide me. And

52:53

now that I don't egotistically attach myself

52:55

to it, I am

52:58

just a much happier person and everything is just

53:00

falling into place. Speaking

53:02

of spiritual beings, what did you learn

53:04

from Bill Murray? Bill

53:07

Murray is my spirit animal. About

53:10

20 years ago, I saw

53:12

a film called Lost in Translation and

53:15

I thought this is a person who

53:17

feels so real. He's not

53:20

acting. He is but he

53:22

isn't. I looked at his

53:24

eyes in that performance and I saw a man

53:26

who was suffering who was dealing

53:28

with some real life shit that

53:31

was coming through the film. And

53:33

not only that but I felt my own

53:35

suffering and I felt a

53:38

connection to that suffering. It's like when you

53:40

look at a painting and

53:43

you see yourself, I saw myself in Bill

53:45

Murray. And so I did

53:47

a Google search just to see what he

53:49

was up to and then saw that he

53:52

was appearing at people's parties and

53:54

was like spotted at somebody's dorm room or something

53:56

like that and he went into their house and

53:58

just started washing their dishes. So

54:01

it started this movement where people started putting out

54:03

banners saying, Bill Murray, please come here. Welcome

54:06

here. I thought to

54:08

myself, what kind of

54:10

man like him puts

54:13

themselves into the general population

54:15

like that? And

54:18

I identified with it. I told

54:20

you earlier, I go to these

54:22

conventions and I put myself on

54:24

purpose and uncomfortable positions just

54:26

to absorb humanity. And

54:29

I realized, you know, if you're Bob Pitt

54:33

or if you're George Clooney, you could... It's

54:36

hard to be these people. Like everywhere you go,

54:38

you're recognized. Somebody wants to take a picture with

54:40

you. Someone wants to touch you. Why

54:43

would you subject yourself to this on

54:45

purpose? And I became

54:47

obsessed with that question. I

54:50

started thinking about it nonstop. What

54:52

drives this man? I

54:55

ultimately decided it was spiritual, that

54:57

in order for him to maintain

55:00

his humanity, he

55:02

decided to start teaching us all how to live.

55:05

Now, if you watch what he's doing, he's showing

55:07

you that even the act of doing dishes can

55:10

be a joyful thing as much as going to a

55:12

party. Going back to

55:14

curiosity and joy, you can

55:16

find joy in the most mundane

55:18

of things if you

55:21

try. And so, he's

55:23

showing us a really beautiful thing. It's

55:26

not about the sort

55:28

of prank of showing up at a house and washing dishes.

55:30

It's about showing you that

55:32

dishes are a fun

55:34

thing. If you walk down

55:37

the street and you just suddenly start dancing with someone,

55:39

you're showing them... It's almost like

55:42

they had a weird dream when they run into him. He'll

55:44

take your french fry off your plate and they'll say, no one

55:47

will ever believe you. I

55:49

love that story. And I

55:52

think that I want Bill Murray

55:54

to live forever, but when

55:56

he leaves this earth, this

55:59

go round... tens of thousands, hundreds

56:01

of thousands of stories of Bill Murray are going

56:03

to come pouring out. And that

56:05

man's going to look like a saint. He

56:07

is a saint of sorts. You know, he's a very difficult

56:10

person to work with, I've heard, because

56:12

he demands the best of people. He expects people to

56:14

show up and give 100% and his

56:17

bar for talent and for art is incredibly

56:19

high. But I

56:22

can tell you how I met him. So I put

56:25

my dream out into the universe that I want

56:27

to meet Bill Murray and

56:29

someday it would happen. And

56:31

I visualized it and I said, and when I meet

56:33

him, I'm going to get to ask him a question,

56:35

just one question. That's the most important question to me.

56:38

If you do this, I guarantee

56:40

you most of these things will come true, not

56:43

in the exact way that you imagine they'll come

56:45

true, because the universe

56:47

works in its own mysterious ways.

56:50

When I set out to meet Bill Murray, I

56:53

did not have money. When I met

56:55

him, I did. One day I was sitting

56:57

on my couch. My favorite site to

56:59

shop on for gifts for friends is Charity

57:01

Buzz. And I was on Charity

57:04

Buzz and all of a sudden

57:06

this thing popped up that said, spend

57:08

a day of

57:11

golf with Bill Murray. And

57:13

I was like, what on earth? No

57:16

way. And I was like, I'm

57:18

in a position where I could buy this. Do

57:20

I do it? And so I said,

57:23

yes, I do. This is my chance. This universe

57:25

has just handed me an opportunity

57:27

and I get to support charity at the

57:29

same time. Like how beautiful is that? So

57:32

I reached out to the organizers. I

57:35

didn't know how to golf. That's the

57:37

funniest part about this. I had never

57:39

gone out to golf in my life.

57:41

I actually had a pretty negative

57:43

opinion of golf. I thought it was

57:46

hoity-toity and only for wealthy people and

57:48

it just was not for me. And

57:51

so I reached out to them and I said, I

57:53

know this is a very strange request,

57:55

but would it be possible if I just ride along with

57:57

him while he plays and I could be his caddy? And

58:00

so they wrote back and they said, well, he's willing to have lunch

58:02

with you. And I was like, oh, no, I heard

58:05

golf is like a full day affair. Like I really want

58:07

to know this man. Can I please just come

58:09

along? And to his credit,

58:11

he said, sure. He said,

58:13

absolutely. So the

58:16

day that I showed up, he paired me

58:18

with his partner, Scott Simpson, who

58:20

is an amazing man, just absolutely amazing

58:22

man. For the first 10 holes I spent with

58:25

Scott Simpson, brought my friend Emily Gillette, who's

58:27

an amazing golfer because I figured one of us

58:29

has got to be able to play. So

58:31

I brought Emily and she was paired up with Bill.

58:35

And a little over half of the day later, he comes over

58:37

me and taps me on the shoulder. And he's like, didn't you

58:39

buy this whole thing? And I was like, yeah. And

58:42

he goes, don't you want to meet me or

58:44

come for a ride? Play golf with me?

58:46

Because I was having the time of my life with

58:48

Scott Simpson. So I go

58:50

out and golf with Bill and he was teaching

58:53

me how to chip and how to putt and

58:55

how to everything. And he was just

58:57

so gracious and didn't care if I

58:59

knew how. And he took us out to Clint Eastwood's golf

59:01

course. And I

59:03

got to ask him my question. And

59:05

my question was, how

59:08

do you stay present? When I

59:10

asked him, he stopped the golf cart and he gave

59:12

me the stare. And

59:16

you could tell it just took him by surprise. It was

59:18

not what he was expecting out of

59:20

this whole ordeal. All

59:22

of a sudden, he points to the hill and he goes, turkey.

59:27

And I go, what? And he points to the hill

59:29

and he goes, turkey. And I was like, okay, turkey.

59:32

All right. I looked at him and we

59:34

start talking about this turkey. And he's like, he

59:36

called it a he. And so I joke and I'm like, you

59:39

don't know the pronoun of the turkey. And so then we got

59:41

talking about that and joking with him. So

59:44

then I came back to it again and started talking

59:46

about it again. And he goes, tree. He points over

59:48

a tree. Tree. And I

59:50

was like, yeah, that's a tree. And it became very clear he wasn't going

59:52

to answer this question. What

59:54

I didn't realize in that moment was I got

59:57

my first lesson from Bill Murray, which Is

59:59

how do you stay present? That. Notice.

1:00:01

What's around you? Marmol.

1:00:04

And it. There's a fricking turkey

1:00:06

and fanbase like how. Often do you get

1:00:08

to see a turkey not every day. Why?

1:00:10

Do we take the turkey for granted? Why do we

1:00:12

take the tree for granted? At

1:00:14

first. I. Was like I'm not getting the

1:00:16

answer in. this is frustrating. By.

1:00:19

Later on when I reflected on the day.

1:00:21

I. Realized he did answer me. I

1:00:24

got my answer. He. Was just an

1:00:27

incredible valuable lesson. And it

1:00:29

definitely helped me on my spiritual journey. In.

1:00:32

A way that is just so profound. To.

1:00:35

Tell me what? The violin kid? So

1:00:37

this goes back to just fallen

1:00:39

your curiosity. I. Have a friend

1:00:42

named Michael. Tiffany's a wonderful entrepreneur. And

1:00:44

somebody have known for. A long time and

1:00:46

be go to Def Con Southern going to death constance

1:00:48

def con for. Since I was eighteen

1:00:51

years old. We. Were fantasizing a

1:00:53

few years ago. That wouldn't it be cool

1:00:55

if we hired a violinist? the follow us

1:00:57

around and just sort of play a soundtrack.

1:01:00

Wherever. We went. Because I'm really

1:01:02

into performance art in general. And

1:01:04

I thought it would just be really funny if you

1:01:06

just show up to a meeting and you're like hold

1:01:08

on. My violin players here. have them play. It

1:01:11

as be centered on. This. Kind of

1:01:13

anything. And so we daydreamed

1:01:15

about it, joked about it, and put it

1:01:17

away. Were. Walking through

1:01:20

Def con. And. There

1:01:22

is a damn man boy.

1:01:25

He. Was sixteen years old? This he may be. Saying.

1:01:29

A violin and it's so beautiful. And he's

1:01:31

busking in the middle of this conference. And.

1:01:33

In front of his violin case it

1:01:35

says raising Money for a certification course.

1:01:38

I ask thing i that how much do you need

1:01:40

and he's like any two thousand dollars to take this

1:01:42

class. As and okay. And

1:01:45

I said hi and then it's from the Michael Tiffany.

1:01:48

And we Seraphine goes. Are you thinking what? I'm thinking?

1:01:51

And I said I'm thinking personal violent player for the

1:01:53

day What are you seen. Any

1:01:56

says. i'm with you and i

1:01:58

said he goes you want to go have these And I said,

1:02:00

yeah. So we walked off to

1:02:02

him just as the conference was about to shut him

1:02:04

down and tell him to close his violin and get

1:02:07

the heck out and said, we're

1:02:09

going to pay for your class. But here's the deal.

1:02:11

Are you willing to follow us around all day

1:02:13

and just play music for everyone wherever

1:02:16

we go? Because the

1:02:18

conference didn't care that he was playing violin. They cared that

1:02:20

he was asking for money is really

1:02:22

what it came down. They didn't want that to become a thing. But

1:02:25

they absolutely loved that he was playing violin. And

1:02:28

he asked his dad, and his dad was like, sure.

1:02:30

So he and his dad just ended up going

1:02:33

with us all day long. We went into

1:02:35

the conference hall. He would just sit

1:02:37

there and play music. When we were walking down

1:02:39

the hallway, he would play like the

1:02:41

Imperial Death March, or he would play Game of Thrones.

1:02:45

It was just really fantastic. And it

1:02:48

changed his life. He was able to

1:02:50

take that class, and he changed our

1:02:52

life. And it was just miraculous

1:02:55

and beautiful. And it just goes to show.

1:02:59

You can do these things. We can all

1:03:01

create magic in the world for

1:03:03

other people and for ourselves if you think about

1:03:05

a situation and you act in that moment. You

1:03:08

strike me as an incredibly evolved human.

1:03:11

And I'm curious that given

1:03:13

it's been quite a while since you

1:03:15

made those Uber and SpaceX investments, obviously

1:03:17

unbelievable returns earned from those and many

1:03:19

others, how

1:03:22

your investing is

1:03:24

most different today, if at all, from

1:03:27

when you made those kinds of investments.

1:03:29

And maybe it's an excuse to talk a little

1:03:31

bit about long-term adventures and what you're building there

1:03:33

and why you're doing it. But

1:03:35

I'm just so interested to know how

1:03:38

your practice has evolved alongside

1:03:41

your own evolution. Yeah,

1:03:43

so I think when I first started investing, I

1:03:45

made a lot of mistakes. We hear

1:03:47

about the wins, but you don't hear about the losses.

1:03:50

Because you're really tuning your antenna in

1:03:53

the beginning. My first check ever,

1:03:55

obviously, ended up being a wild success. But there

1:03:57

was lots of checks after that that did not.

1:04:00

You have to accept those failures as

1:04:03

a lesson as

1:04:05

you go forward and then internalize those

1:04:07

lessons. What did I

1:04:09

do wrong? What did I not see? Was it

1:04:11

out of my control? Did I still

1:04:14

do the right thing but then it was the wrong

1:04:16

timing, etc., etc. And then you hone

1:04:18

that into your gut feeling so that when

1:04:20

the next time comes around, you

1:04:23

can make hopefully a better decision. Now

1:04:26

I've been at this hundreds of companies. I

1:04:29

was at Founders Sun, obviously was on the

1:04:31

investment committee there, have seen many, many, many

1:04:33

deals. My intent is getting better

1:04:35

and better and better. I

1:04:37

think my job now is to teach future

1:04:40

generations how to trust their gut. So,

1:04:44

when I left Founders Sun, I joined

1:04:46

Lee Jacobs at Long Journey Ventures and

1:04:49

he's a decade younger than me. He's

1:04:52

just starting out and hitting his

1:04:55

stride. He's been at it for

1:04:57

a while but his early investments are

1:04:59

starting to bear fruit. For example, he was

1:05:01

a seed investor in loom and loom

1:05:03

just exited so he had his very first exit.

1:05:05

So, he's got his first story

1:05:07

right now which is really, really exciting. And

1:05:11

so, my job is to hopefully

1:05:15

help him and inspire him to, one,

1:05:19

I have no doubt he's going to be wildly successful.

1:05:22

Same thing with Ariel. I

1:05:24

just want them to follow their North Star

1:05:26

in the end which is what causes do

1:05:28

you care about where

1:05:31

as you are successful, you

1:05:33

can make a real dent in them. In

1:05:36

the beginning, it was about making the

1:05:38

money and continuously deploying the money and

1:05:40

the causes that I was supporting through

1:05:43

the actual companies themselves. But

1:05:45

now, I'm starting to think about all my actions. How

1:05:49

do they help the bigger whole? So,

1:05:51

sometimes you'll see me doing things with

1:05:54

companies that we have very small investments in and

1:05:56

you'll see me putting a lot of time into

1:05:58

it. Even though I'm... None

1:06:00

of them Returns are gonna be huge. Because.

1:06:02

It doesn't really matter. Less person's

1:06:04

out there doing something incredibly important.

1:06:07

It's. Not about opportunity costs. I'm

1:06:09

a firm believer in whatever you put out in

1:06:11

the universe comes back to you. You.

1:06:13

Know the do good things, Good things come back

1:06:15

to sell. It works. So. What's

1:06:18

changed for me is. Just.

1:06:20

Being more methodical about my time, how

1:06:22

I'm spending it, Who I'm spending it

1:06:24

with? What? Kind of vibrational energy

1:06:27

as around me. Am. I listening

1:06:29

of the vibrations of the world around me? Are they

1:06:31

listening me up and so forth. And.

1:06:35

That's. All I want to focus on because.

1:06:38

I. Just want. To. Make of

1:06:40

denser from that's gonna be around long

1:06:42

after I'm dead. And. My.

1:06:44

Spirit is inside of it somehow. Is

1:06:47

lives in the values it lives in

1:06:49

the. Discussions that we've had.

1:06:52

In so. I believe that

1:06:55

are. Pieces around investing at

1:06:57

the combination of the three of us, but

1:06:59

my spirit is definitely in their. Found

1:07:02

her son had the spirit. It comes

1:07:04

from loot know said. He.

1:07:06

Was one of the original founders of found her son.

1:07:09

He dared to disrupt.

1:07:12

The. Venture industry to treat the

1:07:14

first. Truly founder friendly venture from

1:07:16

and this is not about the value add

1:07:18

by the way, He was about.

1:07:21

Not. Ever firing a founder and removing

1:07:23

them from their company. Position

1:07:28

which is the will not. Be

1:07:31

seen and. Universe.

1:07:35

Simple thing to hang your hat on,

1:07:37

but it's actually. In the

1:07:39

end comes down to be incredibly important as they

1:07:41

think that the soul. And spirit of the company

1:07:43

lives in the founder. Since.

1:07:45

Yesterday I talked to one of us

1:07:47

on us on partners about investment or

1:07:49

were looking at and I asked and

1:07:52

the question was like but attributes using

1:07:54

matter in the next investor for this

1:07:56

business cause of Israel wants succeeds you

1:07:58

are to said well. The. Dad

1:08:00

reviewed the we wanted that they leave them alone. Success,

1:08:04

you know, we believe that Vs

1:08:06

wrestlers or cut out useless, and

1:08:08

they just waste people's time with

1:08:11

their supposed value. It's. Such

1:08:13

a funny thing to think about,

1:08:15

but it makes you wonder about

1:08:17

your lessons or experience with the

1:08:19

professional investing world. So. Much of

1:08:21

what makes you so interesting to me. Is.

1:08:24

Just so different than like the institutionalization

1:08:26

of an asset class, but he you're

1:08:28

a lot about as it relates to

1:08:30

venture these days. And there's so much

1:08:33

money flowing around, so of course supply

1:08:35

rises to meet demand. But I'm really

1:08:37

curious how you would assess. This.

1:08:39

Whole world. The good, The bad. The ugly.

1:08:42

Having. Now been in it quite some time. Yeah.

1:08:45

My philosophy isn't quite as far as

1:08:47

founder Santander spend is like we invested

1:08:50

in. You are now at your and

1:08:52

around. And. It's your job to

1:08:54

extract value from us. A certain

1:08:56

founder loves that because they know

1:08:59

how to get. Back they look at that

1:09:01

group of people on the know that are connected to

1:09:03

and they know what to ask for. We

1:09:05

are a little bit. To. The last

1:09:07

of that of they were on the far. End

1:09:10

of the spectrum. We are

1:09:12

more hospitality orientated because I

1:09:14

think that the seed stage.

1:09:16

Being. Hospitality oriented is important.

1:09:19

What? That means is one of our values

1:09:21

as be a buddy. Bobby's

1:09:24

aren't grandmother's to. Give. You

1:09:26

hard advice. But. They love you.

1:09:29

And so. Our. Job is

1:09:31

to give honest. Feedback.

1:09:34

To the founders. But gives

1:09:36

them unconditional love. Was.

1:09:38

A founder needs to. Here is the hard

1:09:41

stuff. They need to hear like

1:09:43

you're not performing compared to the rest of

1:09:45

our portfolio, companies have the same vintage, maybe

1:09:47

in the same space, or. The.

1:09:49

Person you've hired is probably not.

1:09:52

Cutting it, The. Other thing is

1:09:54

to letting them know when they had. An

1:09:56

Amazing Things that you notice. And

1:09:58

giving that be back to. Nobody would do.

1:10:01

Then. Been married for them in the

1:10:03

hard times because. The. One thing that.

1:10:06

All Ceos are afraid of is

1:10:08

really revealing all their. Cards to

1:10:10

investors. Because. It could backfire.

1:10:13

That's. Why they always say it's always up into the

1:10:15

right Everything great were chill on it. And.

1:10:17

Then you later on find out that's not really

1:10:19

the case. If. You can form

1:10:21

a true relationship with your founders. They're gonna

1:10:23

tell you when things are not going right

1:10:25

because. They. Want you to lean in

1:10:27

and help? We want to be there. When.

1:10:30

You've had a loss on the family. We want to

1:10:32

be there when your best. Friend: Something happened

1:10:34

to them. Because. We are

1:10:36

human beings At the end of the day. Is

1:10:38

a mental game. So. We

1:10:41

do a lot of things around like mental

1:10:43

coaching and. Presence. Of Mind and

1:10:45

things like that with our founders. We.

1:10:47

Think they're all the rest of it. Is.

1:10:51

Gotta be a core competency of the company. Might like we're

1:10:53

not gonna help with marketing, we're not and help with the

1:10:55

hiring and or any of these things. Unless we

1:10:57

have a candidate, Mitt lands on our laugh. And.

1:10:59

Then we do place them in companies. We absolutely do

1:11:01

that. But we're not going to go out and be

1:11:03

recruiters. All. Of that needs to

1:11:06

be corridor your business. And.

1:11:08

I think that's what truly matters,

1:11:10

especially the early stages. One.

1:11:12

Of the things that just emerged from his

1:11:14

ask you about was integral family Systems and

1:11:17

saucer to know. Where. You weren't there. So.

1:11:20

I was talking to Justin and. My. Partner.

1:11:22

And they said you really should look into I

1:11:25

assassin try it out. So then I tried it

1:11:27

out. And I win in. Skeptical.

1:11:30

And team out realizing oh my

1:11:32

gosh, how amazing is that? For

1:11:34

people that don't know what iss

1:11:36

is you basically. The

1:11:38

all your part. of your

1:11:41

personality as there are no bad parts. Every

1:11:44

part is there to serve you, including. The ones

1:11:46

you might not like. And they come

1:11:48

on line to serve you because they're trying to

1:11:50

defend you and protect you. Yourself,

1:11:53

that's underneath all of that stuff.

1:11:55

And when you start treating them as

1:11:58

separate entities and have curiosity. About them. start

1:12:00

having conversations with them, you

1:12:02

start to realize they're automatic processes that come

1:12:04

online that you can then give them other

1:12:07

jobs to do. And you

1:12:09

can change your personality permanently

1:12:12

for the better. I've gotten rid

1:12:14

of some behaviors that I

1:12:16

thought were unchangeable through IFS,

1:12:20

nervousness, types of nervousness, types

1:12:22

of reactions to people

1:12:24

talking to me and realizing

1:12:27

that these were all just automatic functions

1:12:30

of how I show up and react

1:12:32

to any kind of reception or stimulus

1:12:35

in the world. And it wasn't about

1:12:37

the person I was dealing with, it was about me. In general,

1:12:40

it's usually all about how you handle

1:12:42

anything coming at you. A friend

1:12:45

of mine said something really powerful to

1:12:47

me once, which was, if

1:12:50

people are coming with you with anything but love,

1:12:52

it's not about you. Do

1:12:54

you still feel fundamentally flawed

1:12:56

in any way? Absolutely.

1:12:59

Absolutely, I feel flawed. You're

1:13:02

going to hear people talk about when they

1:13:04

talk about spirituality about being asleep. And

1:13:06

what being asleep means is going

1:13:09

back into your mechanical automatic reflexes

1:13:11

of reacting to life and

1:13:13

just sort of not being truly present.

1:13:17

And if I have a flaw, it's just the

1:13:19

flaw of being human and not realizing that I'm

1:13:21

not being present in the moment.

1:13:24

And so, that's something that I want to grind away

1:13:27

at and fix over time. I

1:13:30

think that sometimes I

1:13:32

can be reactive to things in

1:13:35

ways that I wish I wasn't. So,

1:13:37

I'm working on those things. None of

1:13:39

us is perfect. I think the

1:13:41

whole experiment of life, if

1:13:43

you are an infinite being, just pause

1:13:45

at this for a moment. If you're an infinite being,

1:13:48

being in a body is meant to basically

1:13:51

give you artificial constraints. And

1:13:54

what if it was possible that

1:13:56

maybe you even chose these restraints? I

1:13:59

want to be an in this situation, I want to

1:14:01

overcome this adversity. I want to have this

1:14:03

hard chat. I want these things

1:14:06

and I wanted them. And so I've got to figure out how to get

1:14:09

to the other side of them. So

1:14:11

all of our imperfection is just a

1:14:13

lesson. That's all it is to me. This

1:14:16

is kind of a weird one, but if you had

1:14:19

in a checking account $1

1:14:21

trillion, what would

1:14:23

you do with it? I would

1:14:26

disrupt the Hollywood industry. I

1:14:29

would reimagine the studio

1:14:31

system and I would build a company around

1:14:33

it. Say

1:14:36

more why, what about it? You've

1:14:39

got to look back at Hollywood and how it was founded.

1:14:42

The old studio system, all of the artists used

1:14:44

to work for the studio and

1:14:46

they were on payroll. And

1:14:48

then what happened was they became

1:14:50

wildly successful and then fans loved them,

1:14:53

but they had no upside. So

1:14:55

basically they had no way to really

1:14:57

capture any of the Stan engagement. So

1:14:59

they couldn't get money from public

1:15:02

appearances and things like that. Along

1:15:04

came Michael Ovid and turned that on a

1:15:06

10 and created something called CAA. I

1:15:09

just had him on. It was a very fun episode. Michael

1:15:12

Ovid is the best. I love that man. And

1:15:15

he reimagined how an industry could

1:15:17

operate and he put the power back in the hand

1:15:19

of the artists. That's why it's called the creative artist

1:15:21

agency. And he fought

1:15:23

for these artists and basically started packaging

1:15:26

these deals that were full

1:15:28

packages where they developed everything and then

1:15:30

worked with the studios on financing and

1:15:32

distribution. Still that

1:15:34

way today. And unfortunately, kind

1:15:37

of like all protectionist rackets that exist out

1:15:39

there, they don't want to adapt

1:15:41

to the times and the times are changing.

1:15:44

And now we have Netflix, you know, in

1:15:46

the beginning, they were pretty short-sighted. They thought

1:15:48

that DVDs coming in the mail was like the

1:15:50

Holy Grail. They didn't see where

1:15:52

the evolution of this thing was going.

1:15:55

Kind of like Napster disrupted the music industry and

1:15:58

we ended up with Spotify. haven't

1:16:00

ended up with a

1:16:02

new model for how studios

1:16:05

operate. We're starting to

1:16:07

see some interesting things

1:16:10

happening with like NFTs and Web3

1:16:12

and distribution techniques for content that

1:16:14

have never been tried before. Whenever

1:16:17

you have gatekeepers who are the

1:16:19

only people who are putting out

1:16:21

content, that means that there are millions

1:16:24

of voices that aren't heard. And I

1:16:26

believe that every voice has

1:16:28

a chance to be heard and ought to be heard,

1:16:30

even if you don't like what they have to say.

1:16:33

Because how else can we get to the right answers

1:16:36

if the full discussion isn't happening? So

1:16:39

the movies that we're seeing right now are

1:16:42

dumbed down for general

1:16:44

audience appeal. They're made to

1:16:46

make the most amount of money possible, but

1:16:48

they're not made to teach you potentially how

1:16:51

to live your life differently, or

1:16:53

to question yourself.

1:16:55

Art has an amazing way of

1:16:57

moving the needle of culture, and

1:17:00

for opening people's minds and hearts

1:17:02

to subjects that they might not have

1:17:04

otherwise thought about. And so

1:17:06

I'm afraid right now we're in kind of

1:17:08

a monoculture where there's

1:17:11

only a few people making

1:17:14

content and they have an agenda. If

1:17:16

you look at a lot of this content, it's

1:17:19

being censored by the CCP. We're

1:17:21

not even allowed to criticize China in any of

1:17:23

our film, we should be allowed

1:17:25

to criticize China in our films. That

1:17:28

should be okay. And

1:17:30

the fact that we're not alarmed by this, to

1:17:33

me is kind of nuts. I

1:17:36

would want to bring transparency to accounting

1:17:38

in the studio model, to where

1:17:40

everybody understands the waterfall, and

1:17:42

understands who's getting paid what and how. I

1:17:45

would love to give power to artists, and

1:17:48

to the early believers in that system. So

1:17:51

for example, in venture, angel

1:17:53

investors can invest in a company, and

1:17:56

we have a lot of upside

1:17:58

protection. So the later

1:18:00

investors come in and save the day of

1:18:02

the company. Maybe they have some

1:18:05

preferences. Maybe some things happen where they

1:18:07

get rewarded, but you should never screw over

1:18:09

the first people who believe. Because

1:18:12

you would have never had the opportunity in the first place

1:18:14

to invest later on, if you screw over

1:18:16

those first people who believe Hollywood is totally

1:18:19

based off of screwing over those first believers.

1:18:21

And so there's a lot of people who put money in or

1:18:24

wrote a script or did a lot of things that

1:18:26

they don't ever recoup that money. It's

1:18:28

only the later stage investors who do. I

1:18:31

just really, really think that ideas have to

1:18:33

flourish. I'm a first amendment nut.

1:18:36

I donate money to the UCLA, Amicus

1:18:39

brief clinic down in LA, and I'm

1:18:42

very, very, very drawn

1:18:44

to that cause. And so

1:18:46

a lot of the philanthropy that I do in the

1:18:48

first place is around the first amendment. So

1:18:51

if I had a trillion dollars, it would

1:18:53

be to go after Hollywood. The next thing

1:18:55

would be create a school of comedy. Where

1:18:58

we train the next generation of comedians.

1:19:01

Because I think that what the world

1:19:03

needs more of is laughter. Because

1:19:05

this is how we let out steam about what's

1:19:08

going on in the world. We're

1:19:10

all too sensitive right now. Everything

1:19:12

is offensive. We got to stop being

1:19:15

so concerned about the words that people are saying and

1:19:18

learn to think for ourselves instead. Figure

1:19:20

out what our inner voice is or true north

1:19:22

is. And then it doesn't matter what

1:19:24

people say. It shouldn't even hurt you. I

1:19:27

would say that the trillion dollars is a

1:19:29

lot of dollars. It's meant to expand

1:19:31

the mind. Yeah. I

1:19:33

mean, I probably would try to work on

1:19:35

legalization of mind expanding

1:19:38

substances, MDMA, psilocybin,

1:19:41

et cetera. Probably put more money to work behind that. I

1:19:44

probably would try to work on incarceration

1:19:47

rates. People that are

1:19:49

in prison or causes that

1:19:51

cause no harm to anybody to

1:19:53

free those people. I probably would

1:19:55

plow a majority of it back in the startups.

1:19:59

If I was asked to describe. One of the things

1:20:01

I'd probably say is every time I see a

1:20:03

text from you, I know it's going to be

1:20:05

something interesting that you've uncovered. It's

1:20:07

almost like dispatches from the future or something is

1:20:09

how I think about it. And

1:20:12

I would love to know just as we

1:20:14

wind down what fun dispatches from the future

1:20:17

you're seeing today. Jen

1:20:19

Z and Jen Alpha are incredibly freaked

1:20:22

out right now about AI. Rightfully

1:20:25

so. A lot of them are going

1:20:27

to school and wondering why they should even bother. I'm

1:20:30

not paying attention to that despair. They're

1:20:32

like, why am I learning these things when I can just

1:20:34

go to chat GPT and ask this question or create

1:20:36

a report with chat GPT that's good enough?

1:20:40

Or why am I learning how to code when there's

1:20:42

co-pilot or these things that are just going to generate

1:20:44

code and create apps just because someone dreams of it?

1:20:46

Like why am I learning the intricacies of

1:20:48

how all this works? And

1:20:51

so one of the things I'm

1:20:53

deeply thinking about, my dispatch from the future,

1:20:55

is how do

1:20:57

we create a world where people

1:20:59

understand nothing is going to

1:21:01

be more valuable than what's created by human hands

1:21:03

in the future? So in a

1:21:06

world where everything is quick, cheap and

1:21:08

flawless, the things that are flawed

1:21:10

have value. So I don't know if you've

1:21:12

ever read the book The Diamond Age. Of course.

1:21:14

Ladies Illustrated Primer, right? Yeah,

1:21:17

exactly. So we're heading

1:21:19

into the Diamond Age. Borders

1:21:22

of countries are being questioned. We

1:21:25

itself is being questioned. Do

1:21:27

we create files of societies through crypto

1:21:29

where people subscribe to a certain

1:21:31

type of living like the Victorians

1:21:33

did in Diamond Age? And

1:21:36

do we have material matter printers that print

1:21:38

everything we need on demand? If

1:21:40

everybody has most of what their needs are

1:21:43

met, what's left? And

1:21:46

what's left is artisanship. And

1:21:48

so I think we're moving into a great age

1:21:50

of artistry, like has never been seen

1:21:52

before. And the big argument

1:21:54

that's coming is whether or not AI created art

1:21:56

is really art. I argue that it

1:21:59

is. I argue that an idea

1:22:01

that someone had in their mind

1:22:03

that they didn't have a paintbrush to bring to life,

1:22:06

now they have that paintbrush. Now

1:22:08

they can take that idea and synthesize it

1:22:10

into something that people can see and express

1:22:12

themselves in ways they never were able to

1:22:15

in the past. Now, and

1:22:17

they not spend 10,000 hours honing that

1:22:19

craft for sure, but

1:22:22

does it make them not an artist? More.

1:22:26

So my dispatch from the future

1:22:28

definitely is going to be around Gen

1:22:31

Alpha and what we do for them and Gen Z

1:22:34

to try to make sure that they

1:22:36

understand they have a future and

1:22:38

to start investing in that future now

1:22:41

so that those platforms exist

1:22:43

so that they understand where they can participate in

1:22:46

this new economy that's coming. Well,

1:22:48

I could talk to you all day long.

1:22:50

I think you have such a fresh and

1:22:52

interesting perspective on the world. Obviously, you've been

1:22:54

one of the more successful investors

1:22:56

of this era. We've explored a little bit,

1:22:58

but we could explore plenty more. But

1:23:00

I'm forced to go to my traditional closing question.

1:23:02

What is the kindest thing that anyone's ever done for

1:23:04

you? I've had so many kind

1:23:06

things done for me in my life that it's so

1:23:09

hard to pick one, but I'm going

1:23:11

to pick this one because I was

1:23:13

hitchhiking on the side of the road when

1:23:16

I was 17, 16

1:23:18

years old. I think I was 16 in

1:23:21

Albuquerque, New Mexico. I'd gotten

1:23:23

kicked out of Denny's because I overstayed my welcome in

1:23:25

there with the bottomless cup of coffee. It

1:23:27

was in the middle of the winter and I went

1:23:30

into a gas station and I got kicked out of the gas

1:23:32

station. I ran out of options. So

1:23:34

I went out to the freeway and stuck my thumb out and started

1:23:39

hitchhiking. I got

1:23:41

hypothermia and I started feeling my body shut

1:23:43

down and I knew I was probably moments

1:23:45

away from death. That's when

1:23:48

an RV pulled up. I

1:23:50

was with a boyfriend at the time. He's like, God

1:23:52

told me to stop for her. Not

1:23:54

you. He pointed to my boyfriend, which is kind of

1:23:57

mean. And he said, but her.

1:24:00

said, but since you're with her, just get in. And

1:24:02

so they picked me up off the ground because I

1:24:04

was not able to move anymore and brought me into

1:24:07

the RV and put a blanket on top of me.

1:24:09

And he gave me

1:24:11

hot chocolate. And he said, Where

1:24:13

are you going? And I said, I'm going to Flagstaff,

1:24:15

Arizona. And the next thing I

1:24:17

knew I woke up and I was delivered to the

1:24:19

front doorsteps of my mother's home at the time. And

1:24:22

so that act of kindness

1:24:25

saved my life. It was a

1:24:27

complete stranger. He told me that

1:24:29

he had circled past me probably eight or

1:24:31

nine times, gone off the

1:24:33

off ramp on the on ramp off ramp on

1:24:35

ramp, thinking that it was

1:24:37

crazy that he was getting this lightning bolt, going

1:24:40

back to lightning bolts to save

1:24:42

my life. But then he was just like, I realize

1:24:44

if I don't stop, she's going to die. And

1:24:47

so he saved my life. And I'm so

1:24:49

thankful to him. I don't even know his

1:24:51

name. Because he just dropped

1:24:53

me off. I slept through the whole ride. But

1:24:56

it was that act of kindness that act

1:24:58

of giving to a

1:25:00

complete stranger and listening to his

1:25:02

gut feeling that I'll never

1:25:04

forget. Wonderful closing

1:25:06

story. Thank you so much for an awesome

1:25:09

conversation and for all your time. Thank

1:25:11

you. If

1:25:14

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