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You may have heard me reference the idea of maniacs on a mission and how much that idea excites me.
Well, David Cenra is my favorite maniac on one of my favorite missions with his weekly crafting of the Founders podcast.
Through studying the lives of legends, he weaves together insights across history to distill ideas that you can use in your work.
Founders reveals tried and true tactics, battle-tested by the world's icons, and has David's infectious energy to accompany them.
With well over 300 episodes, your heroes are surely in the lineup, and his recent episode on Oprah is particularly great.
Founders is a movement that you don't want to miss.
It's part of the Colossus Network, and you can find your way to David's great podcast in the show notes.
Hello and welcome, everyone.
I'm Patrick O'Shaughnessy, and this is Invest Like the Best.
This show is an open-ended exploration of markets, ideas, stories, and strategies that will help you better invest both your time and your money.
Invest Like the Best is part of the Colossus family of podcasts, and you can access all our podcasts, including edited transcripts, show notes, and other resources to keep learning at joincolossus.com.
Patrick O'Shaughnessy is the CEO of PositiveSum.
All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of PositiveSum.
This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.
Clients of PositiveSum may maintain positions in the securities discussed in this podcast.
To learn more, visit psum.vc.
My guest today is Cyan Bannister.
Cyan's life story is remarkable.
She was homeless at a young age, dropped out of high school, and five years ago she suffered an extremely rare stroke.
Yet in spite of all of this, she is one of the most optimistic and curious people you can hope to meet.
Cyan is also one of the great angel investors of this era, having invested very early in SpaceX, Uber, Postmates, DeepMind, just to name a few.
She became the first female investing partner at Peter Teal's Founders Fund and now invests at long journey ventures.
Our conversation is as much about investing as it is about the essence of life and how connecting with that will help us in our professional pursuits.
It's also full of awesome stories about people and companies like SpaceX and Bill Murray.
Please enjoy this fantastic conversation with Cyan Bannister.
So, Cyan, this is a hard one to know where to begin, but since we were just talking beforehand, you sort of gave me the perfect opening question.
Do you think that spirituality is an investable category for venture investors?
I absolutely think that spirituality is an investable category, and it's been long overlooked.
So, I remember when Prey.com was raising and everybody thought, who's going to actually use this?
Which target demographic actually wants this?
And I think that there are a lot of people, especially coming out of the pandemic, who spent two years wondering, why is this happening to us?
What is this all about? Why am I here?
What is my purpose? And then looking inwards and then looking outwards.
And I think people are seeking these answers more than ever before, because when you look online and you read what's going on in the world, it seems like it's increasingly getting darker out there.
I would say that it's not, but this is where spirituality comes in and lets people know where the light is.
I think spirituality comes in many different ways.
It comes in the form of prayer, it comes in the form of meditation, it also comes in the form of potentially even psychedelic medicine.
So, I do think that it's a hugely investable category.
And you look at the success of Angel Studios.
Well, Angel Studios basically crowdfunded ticket sales as well as the development of a film, and it ended up being the best box office film at the time.
And it went completely out of the studio model.
And they basically put out this piece of art that people were clamoring for.
And the studios themselves didn't think that it was an investable category.
How much of your investing thinking does the word contrarian describe?
How do you identify with that word related to your investing strategy?
Peter always says, Peter Teal says, you know, it's okay to be contrarian, but you've got to be contrarian and right.
Being contrarian for contrarian's sake is probably not a good path to take.
But people have labeled me or claimed me as contrarian.
I don't know that I would be self-described as contrarian, but I tend to think differently than other people do.
And so, when I identify an opportunity and I go out and try to convince other people that I've found an opportunity, and they consistently tell me, no, this isn't going to work, which usually indicates to me that I'm onto something.
I know something that no one else does.
I'm thinking in a different way than other people are.
And there is usually high alpha there when you find these secrets.
Before you joined Founders Fund, what did you see in Peter and in them?
And what do you think they saw in you?
Well, I dropped out of high school.
I did not go to university.
And so, I always liked to joke that I went to Peter Thiel University.
And it was a dream come true for me.
I was working at Angelist at the time.
I was an angel investor.
I'd actively been investing at that point for probably about eight years.
And when they reached out to me and asked me to join them, three, it was like a Cinderella story.
I got to go and work with people that I looked up to so much and be able to learn from them and to basically absorb knowledge every single day.
And they brought me on to run their early stage efforts.
But as you know, Founders Fund became a very large fund.
And it becomes increasingly difficult in a multi-stage fund to execute different strategies, especially at the early stage.
And so, they tried their best to help me grow into the muscle of Series A, Series B investing.
And they did everything they could to keep me there.
And I would have stayed if we'd been able to figure out probably some sort of strategy that worked because I do love that team so much.
Working there was probably one of the best four years of my life.
How would you sum up what you learned about the difference between that early, early stage and the slightly later stage that you tried to make work?
What is the phase change that happened that makes your skill in one not necessarily translate to skill in the other?
When you're an early stage investor, you're very qualitative, not quantitative.
And I'm a qualitative investor.
And that becomes very difficult when you're trying to talk to quants or people who think about a world in data rooms and spreadsheets and wanting an answer to how you decided that you want to invest in something because you're trusting your gut or you've thought about the world a certain way or you've been looking for this answer to appear in front of you may look to
others as if you're impulsive because you want to move quickly.
And they want to be deliberate and want to get in the data room and want to know more about the company.
And oftentimes at the early stages of a business, you know very little, you know that you've got a good founder in front of you, you know that they have an idea and they have a shot.
But all of that data is not going to be there.
And so you've got two different types of investor types of minds.
And that can be difficult to navigate and frustrating.
It was actually kind of soul crushing for me.
I tend to like to be incredibly optimistic.
And usually when you get into the quantitative realm of the world, you're dealing with a lot more pessimism.
And so for me, I'm an intuitive thinker.
And I think that if you're an intuitive thinker and you have a sort of a gut feeling about things and you really deeply think about the world, then early stage is probably the best avenue for you.
So obviously at the time when you joined, you had a ridiculous seed investing track record.
We'll talk about some of those companies in a few minutes.
But if you had to abstract away the track record, like the obvious evidence that you were good at doing this, what do you think Peter would have said before you joined about what made you interesting and special relative to say, you know, other people, I'm sure Peter's reference class is pretty good.
So qualitatively, what would he have said?
Quantitatively, you were great.
Peter gave me one of the best pieces of feedback.
One of the things I love about Peter is he's so precise.
He can give you like an amazing piece of feedback if you're willing to listen to it and really digest it.
And he took me on a car ride one day, and he simply said one sentence to me, and it changed my life.
And it actually led to me quitting the firm.
He said, Sian, you're really good at feeling, but you're not really good at knowing yet.
That was it. And I looked at him and I understood exactly what he was telling me.
And I marinated on it and marinated on it.
And I said, do I really want to know?
Do I really want that skill set?
Do I really want to learn these things that are so uncomfortable and unnatural to me?
And is this the right place for me?
And the answer was no. So I think what Peter loved about me and why he wanted me to join the team is because I do have principles.
I do have a North Star. I do make gut decisions very quickly.
I think that there was a world where they had a carve out of a seed stage fund, and it was a separate fund, and it didn't conflict with the main fund investments.
And this probably would have worked out.
I think what he saw in me was someone who thinks differently about the world.
He really loves to reward diversity of ideas and backgrounds.
I think that people don't give them enough credit for that.
The fact that I'm a high school dropout, I didn't go to university is a plus in his mind.
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That's where I really, really, really like to play.
I think that some of the companies, while vilified, like if you look at Uber and you look at hostmates, they've been vilified throughout time, it really, really doesn't take into account that there's people out there that are disabled.
There's people out there that have family on hospice.
There's people out there that have children in daycare and they need that flexibility.
They need that source of income.
And otherwise, they would have been locked into a nine to five job with no flexibility, unable to take care of their relatives, unable to take care of their own medical needs.
And so I want to invest in things that really change and move the needle in people's lives on a grand, grand scale.
And then I think there's obviously venture returns in those opportunities, but they also align with my North Star and my core values.
Are there any other principles that you think about often as you're making a decision or as you're searching for things that might interest you?
Yeah, I really like when a founder has overcome some kind of adversity.
So it's one of the questions I ask, which is, what sort of adversity have you faced in your life?
And I'm not looking for a story like mine.
Adversity comes in many, many ways.
For example, you might be a founder who grew up in a family that expected you to become a doctor or a lawyer, and maybe they immigrated to America, and they know that that's a really good career for you to have.
And so they push you hard to do those things.
And then you say, no, actually, I'm going to go start something else.
And I'm going to build this company because I really feel like it's the right thing to do.
And this is my calling. So answering a call to adventure against your parents could be a form of adversity.
Maybe you went to the military and you were deployed and you had to overcome what you saw.
That's also interesting.
Maybe you were in Parkland and you were at the shooting and you overcame that adversity.
We have founders who are coming out of those.
And I just really think it's remarkable when they come out of one of these experiences with a fresh set of eyes and a new perspective on the world.
And most importantly, hope.
They're just like, yeah, I had it rough or I overcame this challenge.
But I'm so excited about living.
I'm so excited about innovating.
And I look for those founders and I want to help them and I want to be by their side.
Because when you build a company, you're going to be faced with so many amazing challenges.
And if you can't overcome them all, if you can't move past them, if you can't put your ego aside and do what's right for the company and always arrive at the best answer, then you probably won't succeed.
How did you emerge from what was a very difficult childhood with hope and optimism as key parts of your philosophy?
I've been thinking about this a lot as I've been writing.
And I really honestly think that when you're faced with the question of survival, that was literally my question.
I was turned out onto the street when I was 15 years old.
I didn't have a job. You have to ask yourself, do you hunker down and just say, this is it for me?
Or do you say, I've got to turn over all the stones and see where the opportunities are.
I've got to figure this out.
I have to have hope. I have to have faith that something's going to work.
And so I chose to have faith and hope throughout every time.
And it always worked out.
It always did. And I think that had I gone the other direction and just said, there's no hope.
There's no future. I can't do this.
The cards are stacked against me.
It's a self-fulfilling prophecy.
Was there a moment when you first remember making that explicit choice?
Yeah, I was in that moment.
So I became a ward of the state and they removed me from my mother's house.
And they told me I had 24 hours to find a home.
And I didn't have a home.
I didn't know where to get a home.
They told me that if I didn't find a home in 24 hours, they were going to put me in a group home.
I'd been in those group homes and I knew that that's not where I wanted to end up.
And so I just said, I looked up at the sky and I said, please, universe, help me.
And I got an answer, which was I knew one adult and I walked over to her house and I said, can I live with you?
And she said, sure. Very easily in that moment, I could have just sat there and succumbed to sorrow, to suffering, to all of it.
And because it worked out, I just kept doing it.
It was one of those things where I was just like, you know what?
I had a stroke five years ago and same thing.
I looked at it with curiosity.
I looked at it with wonder and got through my stroke.
I lost my ability to walk, my ability to see.
If you look at everything with curiosity and wonder and love and hope, you can overcome a lot of things.
And I think that's what people don't realize is that it takes a lot of bravery to be optimistic.
It's easy to be pessimistic.
It's easy to say that things won't work.
It's easy to say, I'm not going to do that because then you don't have to muster up the willpower.
Sorry, what is it like to look at something like a stroke with wonder and curiosity?
I'm going to have to hear a description of that.
When it happened, I just surrendered.
It was one of these things where I was just like, I have no control over this situation.
I have to trust that the medical doctors that are coming to me, that are the best there is at UCSF hospital, are going to do what's right.
And all I have to do is sit here and try to maintain my calm and try to find all the joy in all of it.
And so like when the students were coming and sticking lights in my eyes and lining up down the hallway because they'd never seen an edema in an eye before, I was like, yeah, line up, come look, come look.
Everybody come look. I've got diamonds in my eyes.
Come. Like it's obviously precious.
You want to see it. Every time I did an MRI, I found it joyful.
Every time I had to do a blood draw, I would just sit there and know that I was contributing to medical science.
Because my stroke was one in five million a year.
It was even rarer than that because I was young.
So it's one of these things where you could either just say like, this is it.
I'm going to die and cry.
Or you just say like, you know what, what if these are my last moments, I may as well make the best of them.
So I did. And I honestly believe granted, I can't prove it.
But I believe that that's what helped and aided in my recovery and why I recovered so quickly.
Why do you think that probably for those listening, like it is for me, it's so hard to imagine much less pull off the feeling of curiosity and wonder in the face of such adversity?
I think everyone listening would probably say, yeah, this is a very rare perspective we're hearing.
And I don't think I'd be able to pull that off.
So why is it so rare? Do you think?
Why is it so rare? I think we've lost touch with our child minds inside of us as a child yearning to be free.
That's cause playing as an adult.
I think we, over time, build our personality.
We get told what we can and can't do.
We wear certain clothes.
They're just costumes.
If you really think about it, you really could wake up tomorrow and dress as SpongeBob Squarepants if you want to.
But something's keeping you from doing it.
And it's really just a perspective shift.
For me, I go out and stare at four leaf clovers.
I haven't found one yet, but I go out looking for them.
Sorry, I don't stare at them.
I look out looking for them.
Did you know that there's a four leaf clover in every 10,000 clovers?
So your chances of finding one are real.
It's not fake. It's not made up.
And children, when you show them a four leaf clover and the pattern of a four leaf clover, find them within like 20 seconds.
They're able to find them because their mind is not clouded with all of this, frankly, garbage that we grownups carry around with us.
And so for me, I'm constantly looking to reconnect with my child self with the spirit that's inside of me that yearns to be free, that yearns to learn about everything.
I think a lot of people take for granted what's around them.
They think they've got it all figured out.
There's like, there's nothing new to learn even about maybe your bedroom.
But if you look around with curiosity about your bedroom, I bet you with a new set of perspectives could see your room in a whole different way.
You could see your backyard in a whole different way.
You could see your friendships in a whole different way.
I just don't think a lot of people understand that that curiosity is inside of each one of us.
So it's really about allowing yourself to be silly, allowing yourself to relax more, be comfortable with who you are and let who that person is out.
I think we are really, really afraid of that authenticity that's inside of us and how people might judge us.
Like I said, if we dressed up like SpongeBob and came to work.
I'm reminded of my favorite roomy quote, which is, take off your mask, your face is glorious.
That's right. That's right.
That's exactly right. If you actually think about what you are, we are an animal.
When we die, we decompose and we become dirt.
So what else are we? All of this is just an avatar.
But there's something inside of us that yearns to be creative, that yearns to build things, that yearns to change the world.
That wants to have a purpose for being here.
And we deny that spirit its existence every day.
I am guilty of this. Everyone's guilty of this.
You spend time with children and you spend time with dogs and you go out in nature and you bathe in nature.
You start to realize the things that truly matter.
Like when I came out of the hospital after having my stroke, I fell to my knees because of the air.
When the air hit my lungs and I was like, whoa, what if I never got to breathe that again?
How magnificent. The sun was on my face and I was like, how splendid.
That's what truly matters in the world.
We make up all of these stories inside of our heads about what's important.
But what's really, really important is remembering just how precious life is and how we have a short amount of time to accomplish all of our dreams.
And they're all accomplishable.
And I really, really hope that when people listen to this, they try to figure out how to tap into that creative, curious side.
Because I'm endlessly curious.
My biggest complaint is there's not a thousand of me that I'm not scalable.
I would love to have multiple cyan agents out there roaming the world.
Breacher of the choir. Yeah, learning as much as they possibly can.
So for me, my appetite for knowledge and for everything is insatiable.
So if I map some of this back to Peter's amazing one liner to you and dig in on that notion of your skill at feeling.
When the feeling is a signaling to you by when you meet with a very young company and founder, maybe describe what that's like.
Is it the recognition of someone that's heeded their calling?
Is it something about the person?
Like walk me through the, I'm sure feeling is hard to describe, but as best you can, how would you describe that skill of feeling that Peter pointed out in you?
If you think about it, business is just art.
The US Constitution is a piece of art.
Money is art. Contracts are art.
Code is art. So the art of storytelling is art.
So when someone's in front of you and they're giving you a pitch, they're telling you a story about who they are and what they want to build.
So immediately I'm a visual thinker and I start spinning up a universe in my mind of what they're trying to build.
Ideally, I've already thought about what they're trying to build by daydreaming, by sitting around and immersing myself in the world.
I go to strange conventions that most of my colleagues would be like, why on earth are you spending time at these places?
But why I'm doing is trying to immerse myself among the general population of people and trying to figure out what their problem points are.
For example, going to a mining convention, not Bitcoin, but actual heavy equipment and seeing like what are these people that are moving the earth thinking about going to a toilet paper convention.
I was curious, like everybody during the pandemic ran and bought toilet paper.
Why did we have a shortage?
I'm going to go to a toilet paper convention and find out things like that.
And I just think that when a person sitting in front of me and they're giving me the pitch, I start daydreaming and I start seeing the truth of what they're telling me.
And if I feel it, then the feeling I call my lightning bolts, it literally feels like a jolt of energy in my body.
And I feel like a tingle.
And it's like, ooh, there's something here.
There's something novel here.
There's something different that I haven't seen.
And then I try to figure out what is different about it is that the person is at the opportunity, is that the timing has someone tried this before and failed.
Why is this person potentially the right person, etc.
And so sometimes it's so overwhelming that I'm just like, I've written checks on the spot because it's like one of these things where I just feel arrested by it.
And sometimes I go and marinate on it and chew on it for 24 hours.
And if I still feel the same feelings, then I make the investment.
But in general, it's this weird intuition that this person is onto something and it could be big.
For example, let's look at Pokemon Go, Niantic.
I was going to ask for an example.
So perfect. Yeah. And I went to work.
I was working at Angelus at the time and I was showing everybody their previous game called Ingress.
And I was playing it and trying to explain to them about how this world would be reskinned.
And instead of these portals that I was playing at, there would be these Pokestops and then there's going to be Pokemon around and everybody's like, you're insane.
What are you talking about?
And I could see it clear as day, but I couldn't understand why no one else could.
And when I go out and start trying to explain this dream to people, this visualization that I see, and they continuously can't see it.
And they came up with excuse after excuse not to invest in it, which was like, Nintendo is a corporate investor.
I don't do investing with corporate investors.
These guys are spinning out of Google.
Do they really have grit?
It was excuse after excuse after excuse.
I was just like, you don't understand.
These people built Google Earth.
They really understand mapping.
And then the other thing was the insight that I had was that company was ultimately a mapping company, not a gaming company.
And trying to convince people of that, they're like, well, they only look at the bird in hand.
They're just like, well, it doesn't look like that right now.
So not interested. And so I think that that's how my mind is different and how I arrive at these decisions is I just really, really trust.
And I really don't care if people don't believe me or think I'm crazy or stupid or any of those things.
And so for me, I don't have those kinds of fears that some people have.
As a matter of fact, the more they disagree with me, it's almost like I feel like it's a sign.
I'm like, huh, that's interesting.
Or I look at the argument and I try to see if it has merit.
Like I said, don't be contrarian for contrarian's sake.
If somebody's coming to you and they have a really good argument, they can talk me out of things for sure.
Maybe it's something that I didn't see.
But sometimes I weigh that piece of advice and I'm like, hmm, I still think that they can overcome that hurdle.
I mean, it makes perfect sense to me that you're not going to get unusually good results by doing the same thing other people do.
So the toilet paper convention makes lots of sense to me.
Do you have a favorite example of some unique input like that leading to an investment that you made?
Uber. I lived in a hotel for a period of time.
It was a nice hotel in San Francisco and the front desk would arrange cards for me to get to the airport.
And this was before Uber was even a thing.
And so there was this livery driver that was my livery driver.
And I really took a liking to him.
So I got his card and I said, why don't I just start booking you directly?
And I'll just ride with you.
You're just an amazing person.
And he was an immigrant from Brazil and just a really good driver and just I really liked talking with him in the car.
One day I was going to the airport and he says, you know, I'm not an investor, Sian, but if I was, I would invest in this thing called UberCab.
Have you heard of it? And I said, no, I haven't.
And he said, well, I'm the only driver.
And he explained to me how UberCab worked.
And I said, OK, so they're paying you by the hour to drive around and pick up people who are texting some phone number.
Keep in mind, there was no app at that time.
It's just a phone number.
And you show up and he's like, yes.
And I said, huh, well, let me know when they're not paying you by the hour anymore.
And the reason why I said that was for years prior, I was thinking about how why is it that I go out and I try to hail a taxi and I can't get one, especially if it's raining or if there's a big conference going on, you'd think that there'd be more taxis that would come online to meet the market demand.
So I started talking to taxi drivers about when you go get your car, what's the first thing that happens?
And they say, well, I have to pay $100, $150 just to get the car to leave the yard.
So they're already in the hole, $150, right?
So they're out there hustling trying to get that $150 back just so they can be in the money.
So they're zooming around like crazy acting like, because everybody says I get in a taxi and they drive super fast.
Well, that's why they drive super fast is they're trying to get to the next fair and the next fair and the next fair.
So then I said, well, how do you become a taxi driver?
And they explained the medallion system to me.
And I was like, wow, what a racket that is.
Definitely seems like a protectionist racket.
So go back to the driver that I'm in the car with.
This is a livery driver, it's not a taxi.
They are regulated by TCP licensing, which means they have to be drug tested.
And they have to go through proof of insurance and all sorts of things like that in order to be a livery driver.
So they started with those for a reason.
And that was the first vision.
A lot of people, the first objection I heard about investing in that company was not everybody can afford a black car.
And I said, well, that's a short term vision.
The long term vision is that everybody's car becomes available and comes online to drive.
And they said, oh, well, strangers won't get in strangers cars.
And I'm like, what they do all the time, they get in a taxi.
You don't know that person and that person doesn't even own that car.
So he gives me Ryan Graves' business card and he says call Ryan Graves.
And I look at the business card and the phone number I think was in like Chicago or something.
And at the time, I had a pretty strict rule about only investing kind of in my backyard.
Because every time I tried to invest outside of my ecosystem, I got hosed.
I didn't know the players in New York or the players in Austin or Europe.
And I couldn't get follow on financing for the companies.
That's all changed, especially since the pandemic and people have become remote.
But then I was just like, ah, so I put Ryan Graves' card away.
Fast forward, David Cornick has this amazing event called The Lobby.
I went to it and basically the lobby is based around the fact that most amazing conversations happen in the lobby of the hotel.
It's not the content. It's not any of it other than that.
And it's absolutely true.
And it also happened in the swimming pool and the hot tub and the various things when you're offsite at a resort that happen.
Like you go snorkeling together, you go swimming together.
So a huge group of us were in a hot tub and there's this guy Travis Kalanick in the hot tub.
And he had just exited from Red Swoosh and he basically announced to everybody he was on the bench looking for his next thing.
As an investor, you always pay attention when somebody says something like that.
We trade on secrets. So I took stock of this personality and his personality was very alpha.
It was very aggressive.
You could tell that everybody sort of quieted down when he spoke.
There's a lot of things you look for in a leader and I noticed that.
And so I thought, well, I'm just going to watch this guy and see what happens.
So a few months later, I got invited to Open Angel Forum, which is a thing that Jason Calcanis did for a while.
And I'm sitting there and like the second presentation that comes up is Travis Kalanick presenting UberCab.
And I wrote to my husband and I said, we need to invest in UberCab like today, right now.
I don't understand what's going on with Ryan Graves, but it's kind of irrelevant.
And we did meet Ryan Graves and we loved him, but we knew, or at least I knew, that Ryan Graves would step aside with a person like that.
He's going to want to be the CEO or Ryan would even recognize he was the natural fit for it.
I'm not sure what happened on the back end, but Ryan did step aside.
He became the COO and the rest is history.
And so there's an example of just being really curious and following the white rabbit, so to speak, down the rabbit hole.
You take that curiosity and you see where it goes.
And then you strike the moment you have that lightning bolt.
The lightning bolt hit me when Travis got up.
Yeah. Fascinating. So what price did you end up investing in Uber at?
I believe that was $8 million.
$8 million? That's the first round.
So that one worked okay for you.
Tell me the second half of the story.
What is it like to be an investor and to hold on to a business that ends up being, I think it just hit an all time high yesterday or something?
Tell me about what that part of this is like.
So there's the decision.
And I remember talking to some of the early Bitcoin people that made the most money in Bitcoin.
And one of the things that they had in common was that they were often already rich because once something 10 or 100 X's, the pressure to sell something can be pretty high.
And then the thing ends up 10,000 X's or whatever.
So I would love to hear that side of this same story.
You bought it. You're in an unbelievable price in a generational company.
Then what? What was it like to watch, to hold, to engage with the company once you had invested?
There's this beautiful period when the company is small and you can send emails to the CEO and they respond.
And that's usually when they're under 100 employees.
And then that disappears.
And it's natural. Every angel investor, every early seed stage investor should understand that this could happen.
Travis becomes more unreachable.
Emil becomes more unreachable because you're not their most important problem of the day.
They're fighting so many fires.
And it's not because they don't like you or love you or aren't even thankful for that first investment.
It's because they've got to run a company.
And so there's this period after 100 employees that they lean on you a lot less.
That's where you kind of just sort of surrender to the big players that are going to write the checks and hope for the best outcome.
There's very little you can do.
You know, in the case of Uber, Chris Saka got involved very early.
He rolled up his sleeves and he actually showed up to board meetings, to planning sessions.
And they saw a lot of utility in that.
And so that's one way that you could stay connected to the business.
For me, that's not my style.
I tend to like to be somebody's backbone.
And they call me whenever they need a door opened or they need something fixed or they want my particular type of advice.
The uncomfortable part happens when the company does really, really well.
And then suddenly everybody starts speculating about your personal wealth and starts telling you what you should do with it.
And you start getting written up in articles and your privacy starts getting invaded.
And that can be pretty daunting.
That happened for a period of time.
And then of course, when they go public, there's a holding period.
And did you hold it this whole time?
Like were you still holding your original investment when it went public?
Yes. Yes. I actually think that it's best psychologically for people to not think about specific outcomes.
To set it and forget it literally.
To say, I will be pleased with whatever happens.
Because that needle is going to move all over the place.
There were times that we thought that our shares would be worth something and then the next day they're not.
You're in for a wild ride at that stage.
And so I just think you shouldn't become too attached to it.
And you should just come up with a plan for why did you do this in the first place?
And what are you going to do with that money once you have it?
So this is something I always try to advise my partners and anyone in the investing spaces.
Why do what we do if it doesn't serve a higher purpose or higher power?
So if you are lucky enough to have an exit of any material means to you and your family, I think it's really, really important to align it with your North Star, whatever it is.
You know, you see Warren Buffett do this.
You see the most amazing people in the world, high net worth individuals who figure out charitable causes to support.
Or how to align their investing by starting a fund and getting institutions that they believe in alongside them.
So that every dollar you write, you maximize that dollar.
You're solving cancer research or you're helping kids go to school or you're helping a pension fund.
Then you're actually really making a dent in the world through capitalism.
And I think capitalism has like such a, I don't know, people use it like a dirty word.
And I think it's one of the most beautiful concepts in the world that we have to protect because it absolutely can move the needle in innovation and change things on multiple levels.
What is beautiful about capitalism too?
Let me go back to it's my first time experiencing it.
When I was younger, I actually felt that business people were evil and they were exploitative and all sorts of things.
And I'm sure there are business people who are those things.
But when I lifted myself up off the streets, it was by selling necklaces and making t-shirts.
So I realized I could scrape up a little bit of money.
I could make a thing and a person out there could buy that thing from me at a markup.
And then I could reinvest that into more supplies and make more money and literally get off the street.
And to me, that was like, whoa, wow.
Why can't everybody do this?
Why can't they see this?
And instead, what they see is various abuses of capitalism.
Capitalism and selfism, just an idea.
It's art. Art can be abused.
All things can be abused.
But at its core fundamental principles, it's extraordinarily liberating.
To zoom to the maybe extreme outcome of what a capitalist system allows for, your story would be remarkable if it was only Uber and nothing else.
But maybe you can tell the SpaceX story.
Oh yeah, the SpaceX story is a good one.
So I worked at a company called Ironport and I was employee number 30.
And it's the best company besides Founder Sun I've ever worked at in my life.
The CEO there was incredible.
His name is Scott Weiss.
And he built a true meritocracy of the culture.
It was the first place that I went to that I felt really valued for my mind above all else.
And every time that they gave me a raise, instead of asking for money, I asked for more equity.
Because I believe so much in this company.
And so I was just like, give me more, give me more equity.
That's all I want. I'll figure out a way to make ends meet otherwise.
And because before that I worked at many startups and the equity didn't turn into anything.
Every one of those companies ultimately failed.
So when I had my first financial windfall was because Ironport sold the Cisco for $830 million.
I think it was 2007. I looked around to my friends and I was very fortunate to have made friends that were angel investors already.
And my husband was an angel investor.
Had already been doing angel investments for 10 years.
And he said, obviously building a company is one way to create wealth.
And he said, but the real way that I make my money is by putting capital into high risk startups.
He's like, why don't you do that?
And I was like, okay. And he said, well, why don't you go out and look for opportunities.
See what resonates with you and come back.
So I did. And I was very, very uncertain and very, very scared to put the money that I'd slept under my desk for into startups.
But then Luke Nosek came over to our house who is a dear friend of my husband's.
They went to college together.
They dropped out of college together and drove west with walkie talkies because they didn't have cell phones.
And got an apartment next to each other, eventually max-lub-chin moved next door.
But he came over and practically got on his knees and begged us for money for SpaceX.
And it was his conviction and his belief and Elon Musk, this love that's undescribable.
This man is going to achieve this vision.
And then I went and talked to some NASA engineers and they said, what he's doing is solid.
And the narrative violation there was a private entity can't enter the space realm.
Period the end. This is NASA.
In the story, the government will never allow him to participate.
I put money in. I was like, you know what, I'm just going to put everything in it.
Everything I made from Ironport, I put into SpaceX.
And I was like, you know, I'm young.
I can do this. I can make the money again.
I can always join another startup.
I can always figure out something else.
I definitely had built myself a safety net.
So I could take that risk finally.
So I did that and it'll probably end up being bigger than Uber by far.
When you think back on these stories, are there lessons that you pull from them or do you just view them as sort of like crazy things that happened?
I mean, the fact that you put all your money in SpaceX is crazy.
I imagine I don't know what the entry valuation was there, but I know what the current SpaceX valuation is.
You can kind of figure out they just blown up a rocket on Launchpad and they haven't figured that out yet and that can give you an idea of timing.
It gives you a sense. I haven't done that in a long time.
So I feel lucky, but I also feel like it's because what I do with the money, I'm going to go back to spirituality, that the universe tends to direct energy in places where people are doing good things with it.
And so I think if I started doing bad things with it, my chances of luck diminish.
I think the fact that I have a North Star and so does my husband and we believe in things like freedom, the US Constitution, we believe in people being able to start businesses for ideas to flourish.
I think these things are very important core values of ours.
And it's possible that we are rewarded as such.
Now, obviously I can't prove it, but I really, really believe that I am a steward of capital that doesn't belong to me.
It is mine to deploy judiciously, but is mine to basically put into innovation and into nonprofit work, to move the needle on this earth to make everybody's lives better ultimately in the end.
And I believe that as long as I continue to hold that hope and I trust my gut feeling, which I believe is kind of divine, my ego is aside.
Like it's one of these things where I don't even think that I'm responsible for some of this.
I don't know if you've read the Rick Rubin book.
I compared myself to Rick Rubin online and I got a lot of backlash and it was funny to me because Rick Rubin is very, very similar to me because we trust these feelings that we have to make decisions.
And for him, it's like I found the Beastie Boys and no one's ever heard the Beastie Boys and they're going to love this.
And I know I'm onto something and for me, Travis Kalanick is the Beastie Boys.
It's totally fascinating.
It's also a good excuse to go back to what we started the conversation with around spirituality.
How did you get into this?
So now that I understand these sort of like following the white rabbit holes that you go down, what is this rabbit hole?
And I don't know if you've made investments in this space or not.
If you have, I'd love to hear how and why and what.
But first tell us the journey that you've been on, the learning journey that you've been on, these are the ones that you've been described in this specific field of spirituality.
Because if I'm not mistaken, a couple of years ago, you were an atheist and maybe that's different now, but I would just love to hear the arc of that story.
Yeah. So a few years ago, I was an atheist and like many people during the pandemic, I had a lot of free time to sit and reflect on, I mean, some people, I hate to say this, some people didn't have the time because they were obviously frontline responders, but I was fortunate enough to sit down and think like, why is this happening?
Who am I? What is my place in the world?
And really, really figure out the why.
Because for a long time, I really felt like we're supposed to just be good people, live a good life and make the best of it.
And we just turned to dust in the end.
And that's all there is to it.
But the one thing I never tried was believing.
I never tried actually having faith.
You might ask yourself, how does one try?
It's not trivial. Like you can't just say, today I try having faith.
I actually had to figure out how to truly believe that the world is magical.
And the moment that I truly believed that the world was magical, then the world became magical.
It rocked the foundation of who I am.
So I had a spiritual awakening, and it's the only way I can describe it.
And I can tell you that each one of us is walking a very thin razor's edge between sanity and insanity at all times.
Serotonin regulates a lot of how we perceive reality.
I had a surge of serotonin in this lightning bolt like no other.
It was basically this surge of energy that went from the base of my spine at the top of my skull.
And suddenly everything in the world looked different.
Everything. I started viewing signs differently.
I started viewing art differently, conversations I was having with people differently.
And I realized everything around us is a projection of our perception of minds.
We, when we're born, when we are born, would come online with like going back to parts work and things like that.
But when we're born, we come online with about four distinct systems that come online.
And then through stimulus of interacting in the world, we develop a personality.
And we think this personality is fixed.
We think it can't be changed.
But it turns out it absolutely can be changed.
Many parts of it can. How I had the spiritual awakening was the realization that all the trauma in my past was a construct of my imagination.
That basically, yeah, it happened.
But it happened like a dream happened, like a nightmare.
A nightmare you wake up from and it's gone and you're relieved.
You're like, oh, that was just a dream.
What turns out trauma is also just a dream.
Because if you can overcome it and you can get past it and you can move forward, you have to realize that that thing, when you spin it up in your mind, creates all kinds of hormones that get released, that shape your reality and how you see the world.
We forget that we're an animal that has hormones and a mind.
And then there's this really special thing called consciousness.
And so I believe that consciousness is kind of like an operating system.
And it brings these parts of us online that benefited us at one point, that no longer benefit us.
Because they have jobs.
I think of them as kind of like processes that come online to assist you.
They're like cron jobs and they're like, I'm here to assist you.
And we don't know to put them away and tell them that they don't have that job anymore.
They don't need to do that anymore.
So once I let go of this huge amount of trauma and I realized that it just didn't matter that these things happened to me in the past.
What matters is literally right now.
And you hear people say this and you're wondering, what does it mean when they say this?
And I always wondered it.
I was like, what does it mean?
When you have the true realization, it's almost like it's written in your DNA.
What that really, really means.
Then you start to let go of so much.
And when you let go, all of a sudden you realize, oh, life isn't so hard.
It's actually quite easy.
And I just have to trust myself and I have to trust my intuition.
And I have to just be. And once you learn how just to be, life gets a lot more simple.
All of a sudden everything you ever wished for in your life just starts coming true.
It becomes effortless.
It's really weird. It's really super weird.
And the only thing that changed in my life was having faith in something higher than myself.
That was it. This is why when you ask me like what sort of insight or brilliance or whatever led to whatever, it's too easy for our ego mind to take credit for everything.
Something gave me that feeling that said, you ought to go deeper into this.
You ought to do this. You've got to take this risk.
You've got to jump right now.
I guarantee you if you talk to a lot of different people, they'll say, I don't know why I did this.
I just had a feeling. And I now believe thoroughly in that feeling.
And I believe that that feeling is the universe or God, whatever word you want to put into it.
And it helps guide me. And now that I don't egotistically attach myself to it, I am just a much happier person and everything is just falling into place.
Speaking of spiritual beings, what did you learn from Bill Murray?
Bill Murray is my spirit animal.
About 20 years ago, I saw a film called Lost in Translation.
And I thought, this is a person who feels so real.
He's not acting. He is, but he isn't.
Like I looked at his eyes in that performance and I saw a man who was suffering, who was dealing with some real life shit that was coming through the film.
And not only that, but I felt my own suffering and I felt a connection to that suffering.
It's like kind of like when you look at a painting and you see yourself, I saw myself and Bill Murray.
And so I did a Google search just to see like what he was up to and then saw that he was appearing at people's parties and was like spotted at somebody's dorm room or something like that.
And he went into their house and just started washing their dishes.
So it started this movement where people started putting out banners saying, Bill Murray, please come here.
Welcome here. I thought to myself, what kind of man like him puts themselves into the general population like that.
And I identified with it.
And I realized earlier, I go to these conventions and I put myself on purpose in uncomfortable positions just to absorb humanity.
And I realized, you know, if you're Brad Pitt or if you're George Clooney, you could, it's hard to be these people.
Like everywhere you go, you're recognized.
Somebody wants to take a picture with you.
Someone wants to touch you.
Why would you subject yourself to this on purpose?
And I became obsessed with that question.
I started thinking about it nonstop.
What drives this man? I ultimately decided it was spiritual that in order for him to maintain his humanity, he decided to start teaching us all how to live.
Now, if you watch what he's doing, he's showing you that even the act of doing dishes can be a joyful thing as much as going to a party.
Going back to curiosity and joy, you can find joy in the most mundane of things if you try.
And so he's showing us a really beautiful thing.
It's not about the sort of prank of showing up at a house and washing dishes.
It's about showing you that dishes are a fun thing.
If you walk down the street and you just suddenly start dancing with someone, you're showing them.
It's almost like they had a weird dream when they run into him.
He'll take your French fry off your plate and he'll say, no one will ever believe you.
I love that story. And I think that I want Bill Murray to live forever.
But when he leaves this earth, this go around, hundreds of thousands of stories of Bill Murray are going to come pouring out.
And that man's going to look like a saint.
He is a saint of sorts. He's a very difficult person to work with, I heard, because he demands the best of people.
He expects people to show up and give 100 percent.
And his bar for talent and for art is incredibly high.
But I can tell you how I met him.
So I put my dream out into the universe that I want to meet Bill Murray.
And someday it would happen.
And I visualized it and I said, and when I meet him, I'm going to get to ask him a question.
Just one question. That's the most important question to me.
If you do this, I guarantee you most of these things will come true.
Not in the exact way that you imagine they'll come true, because the universe works in its own mysterious ways.
When I set out to meet Bill Murray, I did not have money.
When I met him, I did. One day I was sitting on my couch.
My favorite site to shop on for gifts for friends is Charity Buzz.
And I was on Charity Buzz.
And all of a sudden this thing popped up that said, spend a day of golf with Bill Murray.
And I was like, what on earth?
No way. And I was like, I'm in the position where I could buy this.
Do I do it? And so I said, yes, I do.
This is my chance. This is the universe that just handed me an opportunity and I get to support Charity at the same time.
Like how beautiful is that?
So I reached out to the organizers.
I didn't know how to golf.
That's the funniest part about this.
I had never gone out to golf in my life.
I actually had a pretty negative opinion of golf.
I thought it was toyty toyty and only for wealthy people.
And it just was not for me.
And so I reached out to them and I said, I know this is a very strange request, but would it be possible if I just ride along with him while he plays and I could be his caddy?
And so they wrote back and they said, well, he's willing to have lunch with you.
And I was like, oh no, I heard golf is like a full day affair.
Like I really want to know this man.
Can I please just come along?
And to his credit, he said, sure.
He said, absolutely. So the day that I showed up, he paired me with his partner, Scott Simpson, who is an amazing man, just absolutely amazing man.
For the first 10 holes I spent with Scott Simpson brought my friend Emily Gillette, who's an amazing golfer because I figured one of us has got to be able to play.
So I brought Emily and she was paired up with Bill.
And a little over half of the day later, he comes over me and taps me on the shoulder and he's like, didn't you buy this whole thing?
And I was like, yeah. And he goes, don't you want to meet me and come for a ride?
Or play golf with me because I was having the time of my life with Scott Simpson.
So I go out and golf with Bill and he was teaching me how to chip and how to putt and how to everything.
And he was just so gracious and didn't care if I knew how.
And he took us out to Clint Eastwood's golf course.
And I got to ask him my question.
And my question was, how do you stay present?
When I asked him, he stopped the golf cart and he gave me the stare.
And you could tell it just took him by surprise.
It was not what he was expecting out of this whole ordeal.
All of a sudden he points to the hill and he goes, turkey.
And I go, what? And he points to the hill and he goes, turkey.
And I was like, okay, turkey.
All right. I looked at him and we start talking about this turkey and he's like, he called it a he.
And so I joked and I'm like, you don't know the pronoun of the turkey.
And so then we got talking about that and joking with him.
So then I came back to it again and start talking about it again.
And he goes, tree, he points over to tree, tree.
And I was like, yeah, that's a tree.
And it became very clear he wasn't going to answer this question.
What I didn't realize in that moment was I got my first lesson from Bill Murray, which is how do you stay present?
Notice what's around you.
Marvel in it. There's a frickin turkey in front of us.
Like how often do you get to see a turkey?
Not every day. Why do we take the turkey for granted?
Why do we take the tree for granted?
At first I was like, I'm not getting the answer and this is frustrating.
But later on when I reflected on the day, I realized he did answer me.
I got my answer. It was just an incredible valuable lesson.
And it definitely helped me on my spiritual journey in a way that is just so profound.
Can you tell me about the violin kid?
So this goes back to just following your curiosity.
I have a friend named Michael Tiffany, he's a wonderful entrepreneur and somebody I've known for a long time.
And we go to DEF CON. So I've been going to DEF CON since DEF CON 4 since I was 18 years old.
We were fantasizing a few years ago that wouldn't it be cool if we hired a violinist to follow us around and just sort of play a soundtrack wherever we went?
Because I'm really into performance art in general.
And I thought it would just be really funny if you just show up to a meeting and you're like, hold on, my violin players here have them play.
It'd just be a centric and odd.
Just kind of a funny thing.
And so we daydreamed about it, joked about it and put it away.
We're walking through DEF CON and there's a young man, boy, he was 16 years old, 15 maybe, playing a violin and it's so beautiful.
And he's busking in the middle of this conference and in front of his violin case, it says raising money for a certification course.
I asked him, I said, how much do you need?
And he's like, I need $2,000 to take this class.
And I said, oh, okay. And I said, huh.
And then I turned to Michael Tiffany and we start walking.
He goes, are you thinking what I'm thinking?
And I said, I'm thinking personal violin player for the day.
What are you thinking? And he said, I'm with you.
And I said, he goes, you want to go have these?
And I said, yeah. So we walked back to him just as the conference was about to shut him down and tell him to close his violin and get the heck out and said, we're going to pay for your class.
But here's the deal. Are you willing to follow us around all day and just play music for everyone?
Wherever we go. Because the conference didn't care that he was playing violin.
They cared that he was asking for money is really what it came down.
They didn't want that to become a thing.
But they absolutely love that he was playing violin.
And he asked his dad and his dad was like, sure.
So he and his dad just ended up going with us all day long.
We went into the conference hall.
He would just sit there and play music.
When we were walking down the hallway, he would play like the Imperial Death March or he would play games.
You know, it was just really fantastic.
And it changed his life.
He was able to take that class and he changed our life.
And it was just miraculous and beautiful.
And it just goes to show you can do these things.
We can all create magic in the world for other people and for ourselves.
If you think about a situation and you act in that moment.
You strike me as an incredibly evolved human.
And I'm curious that given it's been quite a while since you made those Uber and SpaceX investments, obviously unbelievable returns earned from those and many others.
How your investing is most different today, if at all, from when you made those kinds of investments.
And maybe it's an excuse to talk a little bit about long-term adventures and what you're building there and why you're doing it.
But I'm just so interested to know how your practice has evolved alongside your own evolution.
Yeah. So I think when I first started investing, I made a lot of mistakes.
We hear about the wins, but you don't hear about the losses because you're really tuning your antenna in the beginning.
My first check ever obviously ended up being a wild success, but there was lots of checks after that that did not.
You have to accept those failures as a lesson as you go forward and then internalize those lessons.
What did I do wrong? What did I not see?
It wasn't out of my control.
Did I still do the right thing, but then it was the wrong timing, etc., etc.
And then you hone that into your gut feeling so that when the next time comes around, you can make hopefully a better decision.
Now I've been at this hundreds of companies.
I was at Founders Fund, obviously was on the investment committee there, have seen many, many, many deals.
My antenna is getting better and better and better.
I think my job now is to teach future generations how to trust their gut.
So when I left Founders Fund, I joined Lee Jacobs at Long Journey Ventures, and he's a decade younger than me.
He's just starting out and hitting his stride.
He's been at it for a while, but his early investments are starting to bear fruit.
For example, he was a seed investor in Loom and Loom just exited, so he had his very first exit.
So he's got his first story right now, which is really, really exciting.
And so my job is to hopefully help him and inspire him to, one, I have no doubt he's going to be wildly successful.
Same thing with Arial. I just want them to follow their North Star in the end, which is what causes do you care about where, as you are successful, you can make a real dent to them.
In the beginning, it was about making the money and continuously deploying the money and the causes that I was supporting through the actual companies themselves.
But now I'm starting to think about all my actions.
How do they help the bigger whole?
So sometimes you'll see me doing things with companies that we have very small investments in and you'll see me putting a lot of time into it.
Even though I know that the returns aren't going to be huge because it doesn't really matter.
That person's out there doing something incredibly important.
It's not about opportunity costs.
I'm a firm believer in whatever you put out in the universe comes back to you.
You know, if you do good things, good things come back.
It's just how it works. So what's changed for me is just being more methodical about my time, how I'm spending it, who I'm spending it with, what kind of vibrational energy is around me.
Am I lifting up the vibrations of the world around me?
Are they lifting me up and so forth?
And that's all I want to focus on because I just want to make a venture firm that's going to be around long after I'm dead.
And my spirit is inside of it somehow.
It lives in the values. It lives in the discussions that we've had.
And so I believe that our thesis around investing is the combination of the three of us, but my spirit is definitely in there.
Founders Fund has a spirit.
It comes from Luke Nosak, who was one of the original founders of Founders Fund.
He dared to disrupt the venture industry to create the first truly founder-friendly venture firm.
And this is not about being value-add, by the way.
It was about not ever firing a founder and removing them from their company.
That's it. That's their biggest value proposition, which is they will not mess with you once they've invested in you.
That seems like kind of a simple thing to hang your hat on, but it's actually in the end comes down to be incredibly important, is they think that the soul and the spirit of the company lives in the founder.
Just yesterday, I talked to one of the Founders Fund partners about an investment that we're looking at.
And I asked him the question, which was like, what attributes do you think matter in the next investor for this business?
Because obviously, we all wanted to succeed.
He laughed, he said, well, the attribute that we wanted is that they leave them alone.
We believe that most of these investors are kind of useless and they just waste people's time with their supposed value-add.
It's such a funny thing to think about, but it makes me wonder about your lessons or experience with the professional investing world.
So much of what makes you so interesting to me is just so different than the institutionalization of an asset class, which you hear a lot about as it relates to venture these days.
And there's so much money flowing around.
So of course, supply rises to meet demand.
But I'm really curious how you would assess this whole world, the good, the bad, the ugly, having now been in it quite some time.
Yeah, my philosophy isn't quite as far as Founders Funds.
Founders Fund is like, we invested in you and now it's your on your own.
And it's your job to extract value from us.
A certain founder loves that because they know how to get value.
They look at that group of people and they know who they're connected to and they know what to ask for.
We are a little bit to the left of that if they were on the far end of the spectrum.
We are more hospitality oriented because I think at the seed stage, being hospitality oriented is important.
What that means is one of our values is be a Bubby.
Bubbies are grandmothers who give you hard advice, but they love you.
And so our job is to give honest feedback to the founders, but give them unconditional love.
What a founder needs to hear is the hard stuff.
They need to hear like you're not performing compared to the rest of our portfolio companies of the same vintage, maybe in the same space, or this person you've hired is probably not cutting it.
The other thing is to letting them know when they have done amazing things that you notice and giving that feedback just like a Bubby would do.
And then being there for them in the hard times because the one thing that all CEOs are afraid of is really revealing all their cards to investors because it could backfire.
That's why they always say it's always up and to the right.
Everything's great. We're killing it.
And then you later on find out that's not really the case.
If you can form a true relationship with your founders, they're going to tell you when things are not going right because they want you to lean in and help.
We want to be there when you've had a loss in the family.
We want to be there when your best friend, something happened to them because we are human beings at the end of the day.
It's a mental game. So we do a lot of things around like mental coaching and presence of mind and things like that with our founders.
We think that all the rest of it is got to be a core competency of the company, right?
Like we're not going to help with marketing.
We're not going to help with hiring or any of these things.
We're going to have a candidate that lands on our lap.
And then we do place them in companies.
We absolutely do do that, but we're not going to go out and be recruiters.
All of that needs to be core to your business.
And I think that's what truly matters, especially at the early stages.
One of the things that Justin Meyers told me to ask you about was integral family systems.
I'm fascinated to know what you've learned there.
I was talking to Justin and my partner and they said, you really should look into IFS and try it out.
So then I tried it out and I went in skeptical and came out realizing, oh my gosh, how amazing is that?
For people that don't know what IFS is, you basically view all your parts of your personality as there are no bad parts.
Every part is there to serve you, including the ones you might not like.
They come online to serve you because they're trying to defend you and protect you yourself that's underneath all of that stuff.
And when you start treating them as separate entities and have curiosity about them and start having conversations with them, you start to realize their automatic processes that come online that you can then give them other jobs to do.
And you can change your personality permanently for the better.
I've gotten rid of some behaviors that I thought were unchangeable through IFS, nervousness, types of nervousness, types of reactions to people talking to me and realizing that these were all just automatic functions of how I show up and react to any kind of perception or stimulus in the world.
And it wasn't about the person I was dealing with, it was about me.
In general, it's usually all about how you handle anything coming at you.
A friend of mine said something really powerful to me once, which was, if people are coming with you with anything but love, it's not about you.
Do you still feel fundamentally flawed in any way?
Absolutely. Absolutely.
I feel flawed. You're going to hear people talk about when they talk about spirituality about being asleep.
And what being asleep means is going back into your mechanical automatic reflexes of reacting to life and just sort of not being truly present.
And if I have a flaw, it's just the flaw of being human and not realizing that I'm not being present in the moment.
And so that's something that I want to grind away at and fix over time.
And I think that sometimes I can be reactive to things in ways that I wish I wasn't, so I'm working on those things.
None of us is perfect. I think the whole experiment of life, if you are an infinite being, just pause at this for a moment.
If you're an infinite being, being in a body is meant to basically give you artificial constraints.
And what if it was possible that maybe you even chose these restraints?
I want to be in this situation.
I want to overcome this adversity.
I want to have this hardship.
I want these things. And I wanted them.
And so I've got to figure out how to get to the other side of them.
So all of our imperfection is just a lesson.
That's all it is to me. This is kind of a weird one, but if you had in a checking account one trillion dollars, what would you do with it?
I would disrupt the Hollywood industry.
I would reimagine the studio system and I would build a company around it.
Say more or lie. What about it?
You've got to look back at Hollywood and how it was founded.
The old studio system, all of the artists used to work for the studio and they were on payroll.
And then what happened was they became wildly successful and then fans loved them, but they had no upside.
So basically they had no way to really capture any of this fan engagement.
So they couldn't get money from public appearances and things like that.
Along came Michael Ovitz and turned that on its head and created something called CAA.
I just had him on. It was a very fun episode.
Michael Ovitz is the best.
I love that man. And he reimagined how an industry could operate and he put the power back in the hand of the artist.
That's why it's called the Creative Artist Agency.
And he fought for these artists and basically started packaging these deals that were full packages where they developed everything and then worked with the studios on financing and distribution.
It's still that way today.
And unfortunately, kind of like all protectionist rackets that exist out there, they don't want to adapt to the times and the times are changing.
And now we have Netflix.
In the beginning, they were pretty short-sighted.
They thought that DVDs coming in the mail was like the Holy Grail.
They didn't see where the evolution of this thing was going.
Kind of like Napster disrupted the music industry and we ended up with Spotify.
We haven't ended up with a new model for how studios operate.
We're starting to see some interesting things happening with like NFTs and Web 3 and distribution techniques for content that have never been tried before.
Whenever you have gatekeepers who are the only people who are putting out content, that means that there are millions of voices that aren't heard.
And I believe that every voice has a chance to be heard and ought to be heard, even if you don't like what they have to say.
Because how else can we get to the right answers if the full discussion isn't happening?
So the movies that we're seeing right now are dumbed down for general audience appeal.
They're made to make the most amount of money possible, but they're not made to teach you potentially how to live your life differently.
Or to question yourself.
Art has an amazing way of moving the needle of culture and for opening people's minds and hearts to subjects that they might not have otherwise thought about.
And so I'm afraid right now we're in kind of a monoculture where there's only a few people making content and they have an agenda.
If you look at a lot of this content, it's being censored by the CCP.
We're not even allowed to criticize China in any of our film.
We should be allowed to criticize China in our films.
That should be okay. And the fact that we're not alarmed by this, to me, is kind of nuts.
I would want to bring transparency to accounting in the studio model to where everybody understands the waterfall and understands who's getting paid what and how.
I would love to give power to artists and to the early believers in that system.
So for example, in venture, angel investors can invest in a company and we have a lot of upside protection.
So the later investors come in and save the day of the company, maybe they have some preferences, maybe some things happen where they get rewarded.
But you should never screw over the first people who believed because you would have never had the opportunity in the first place to invest later on if you screw over those first people who believe.
Hollywood is totally based off of screwing over those first believers.
And so there's a lot of people who put money in or wrote a script or did a lot of things that they don't ever recoup that money.
It's only the later stage investors who do.
I just really, really think that ideas have to flourish.
I'm a First Amendment nut.
I donate money to the UCLA, anarchist brief clinic down in LA, and I'm very, very, very drawn to that cause.
And so a lot of the philanthropy that I do in the first place is around the First Amendment.
So if I had a trillion dollars, it would be to go after Hollywood.
The next thing would be to create a school of comedy where we train the next generation of comedians because I think that what the world needs more of is laughter.
Because this is how we let out steam about what's going on in the world.
We're all too sensitive right now.
Everything is offensive.
We got to stop being so concerned about the words that people are saying and learn to think for ourselves instead.
Figure out what our inner voice is, what our true north is.
And then it doesn't matter what people say.
It shouldn't even hurt you.
I would say that the trillion dollars is a lot of dollars.
It's meant to expand the mind.
Yeah. I mean, I probably would try to work on legalization of mind expanding substances, MDMA, psilocybin, etc.
I probably put more money to work behind that.
I probably would try to work on incarceration rates, people that are in prison for causes that cause no harm to anybody to free those people.
I probably would plow a majority of it back in the startups.
If I was asked to describe you, one of the things I'd probably say is every time I see a text from you, I know it's going to be something interesting that you've uncovered.
It's almost like dispatches from the future or something is how I think about it.
And I would love to know just as we wind down what fun dispatches from the future you're seeing today.
Gen Z and Gen Alpha are incredibly freaked out right now about AI.
Rightfully so. A lot of them are going to school and wondering why they should even bother.
We're not paying attention to that despair.
They're like, why am I learning these things when I can just go to chat GPT and ask this question or create a report with chat GPT that's good enough?
Or why am I learning how to code when there's co-pilot or these things that are just going to generate code and create apps just because someone dreams of it?
Like why am I learning the intricacies of how all this works?
And so one of the things I'm deeply thinking about my dispatch from the future is how do we create a world where people understand nothing is going to be more valuable than what's going to be.
More valuable than what's created by human hands in the future.
So in a world where everything is quick, cheap and flawless, the things that are flawed have value.
So I don't know if you've ever read the book The Diamond Age.
Of course. Ladies illustrated primer, right?
Yeah, exactly. So we're heading into the Diamond Age.
Borders of countries are being questioned.
Democracy itself is being questioned.
Do we create files of societies through crypto where people subscribe to a certain type of living like the Victorians did in Diamond Age?
And do we have material matter printers that print everything we need on demand?
If everybody has most of what their needs are met, what's left?
And what's left is artisanship.
And so I think we're moving into a great age of artistry like has never been seen before.
And the big argument that's coming is whether or not AI created art is really art.
I argue that it is. I argue that an idea that someone had in their mind that they didn't have a paintbrush to bring to life.
Now they have that paintbrush.
Now they can take that idea and synthesize it into something that people can see and express themselves in ways they never were able to in the past.
Now, did they not spend 10,000 hours honing that craft?
Sure. But does it make them not an artist?
No. So my dispatch from the future definitely is going to be around Gen Alpha and what we do for them and Gen Z to try to make sure that they understand they have a future and to start investing in that future now so that those platforms exist so that they understand where they can participate in this new economy that's coming.
Well, I could talk to you all day long.
I think you have such a fresh and interesting perspective on the world.
Obviously, you've been one of the more successful investors of this era.
We've explored a little bit, but we could explore plenty more.
But I'm forced to go to my traditional closing question.
What is the kindest thing that anyone's ever done for you?
I've had so many kind things done for me in my life that it's so hard to pick one.
But I'm going to pick this one because I was hitchhiking on the side of the road when I was 17, 16 years old.
I think I was 16 in Albuquerque, New Mexico.
And I got kicked out of Denny's because I overstayed my welcome in there with the bottomless cup of coffee.
And it was in the middle of the winter and I went into a gas station and I got kicked out of the gas station.
I ran out of options. So I went out to the freeway and stuck my thumb out and start hitchhiking.
I got hypothermia and I started feeling my body shut down and I knew I was probably moments away from death.
And that's when an RV pulled up.
I was with a boyfriend at the time.
He's like, God told me to stop for her, not you.
He pointed to my boyfriend, which was kind of mean.
And he said, but her. And he said, but since you're with her, just get in.
And so they picked me up off the ground because I was not able to move anymore and brought me into the RV and put a blanket on top of me.
And he gave me hot chocolate and he said, where are you going?
And I said, I'm going to Flagstaff, Arizona.
And the next thing I knew, I woke up and I was delivered to the front doorsteps of my mother's home at the time.
And so that act of kindness saved my life.
It was a complete stranger.
He told me that he had circled past me probably eight or nine times, gone off the off ramp on the on ramp off ramp on ramp, thinking that it was crazy that he was getting this lightning bolts going back to lightning bolts to save my life.
But then he was just like, I realized if I don't stop, she's going to die.
And so he saved my life and I'm so thankful to him.
I don't even know his name because he just dropped me off.
I slept through the whole ride.
But it was that act of kindness, that act of giving to a complete stranger and listening to his gut feeling that I'll never forget.
Wonderful closing story.
Thank you so much for an awesome conversation and for all your time.
Yeah, thank you. Yeah.
