Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]

0:00 Welcome to this classic episode. Classics are my favorite episodes from the past ten years published once a month. These are end of one conversations with end of one people. There aren't many people like Cyan Bannister. She has defied the odds to become one of the great angel investors of this era, and she will get you thinking about the purpose of your work, whether investing related or not. Please enjoy it. 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.

0:33 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 joincolossis.com. Mm. Patrick O'Shaughnessy is the CEO of Positive Sun. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of positive some. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.

1:03 Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc. Mm. 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.

1:30 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 Thiel'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.

1:57 Please enjoy this fantastic conversation with Syan 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 Do you think that spirituality is an investable

2:13 Category. for venture investors. I absolutely think that spirituality is an investment category and it's been long overlooked. So I remember when pray.com was raising And everybody thought.

2:26 Who's gonna 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.

2:37 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

2:49 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.

3:00 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.

3:16 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.

3:29 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.

3:44 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

3:56 Describe. How do you identify with that word? Related to your investing strategy. Peter always says, Peter Thiel says, you know, it's okay to be contrarian, but you've got to be contrarian and write. Being contrarian for contrarian sake is probably not A good path to take.

4:12 But People have labeled me or coined 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

4:25 When I identify an opportunity and I go out and try to convince other people that I found an opportunity. And they consistently tell me No. This isn't gonna work. Which

4:38 usually indicates to me that I'm on to something. I know something that no one else does. I'm thinking in a different way. than other people are and they're is usually alpha. There, when you find these secrets. Before you joined Founders Fund, what did you see in Peter and in them and what

4:56 Do you think they saw in you? Well I dropped out of high school. I did not go to university. And so I always like 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.

5:16 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 look Up to so much.

5:26 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.

5:37 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

5:55 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.

6:07 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 happens that makes

6:21 your skill in one not necessarily translates to skill in the other. When you're an early stage investor, you're very qualitative, not quantitative. And I'm a qualitative investor in 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

6:40 wanting an answer to how you decided that you want to invest in something. because you're trusting your gut or you 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 is if you're impulsive.

6:56 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

7:13 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

7:23 difficult to navigate. And Frustrating. It was actually kind of soul crushing for me. I tend to like to be

7:31 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

7:46 have a sort of a gut feeling about things and you really deeply think about the world. then early stages probably the best avenue for you. So obviously at the time when you joined You had a ridiculous

8:00 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 he I'm sure Peter's m his reference class is pretty good. So Qualitatively, what would he have said? Quantitatively, you were great.

8:23 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.

8:40 To me. And it changed my life and it actually led to me quitting the firm. He said. Cyan, you're really good at feeling. but you're not really good at knowing yet.

8:50 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?

9:04 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

9:19 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.

9:34 And it didn't conflict with the main fund. investments, then this probably would have worked out. I think what he saw in me With someone who thinks differently about the world. He really loves to reward

9:46 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. He wants to work with investors who never wanted to be investors. So tell me about

10:04 how you think differently, what that North Star is, what those principles are. I'd love to explore those In turn, you can take them however you'd like. I was homeless at a very young age and I grew up very poor. And I always remember where I came from. And so when I do investments, for example, some of the investments I've made in postmates or Uber.

10:26 I always think about the younger me. Which is if I could have driven an Uber. Or I could have delivered a sandwich. That would have been life changing for me.

10:38 And I think a lot of the times when we're investors, we live in a bubble. Our lives are relatively comfortable for the most part. And we lose track of what the rest of the world's experience is. Being able to have flexibility in your income and in your work. Is

10:55 A dream come true for many, many people. And so my North Star is around Ending poverty. Creating Different types of wealth categories and income generating categories for people who didn't have access to those in the past, for example, angelists.

11:13 Crowdfunding. Reg C F. Financing Things like that are really interesting to me. And

11:20 If you look across my portfolio, that's not always the case. Sometimes I'm just really interested in a category. And I want to invest in it. But for the most part I would say that anytime someone comes to me and they say I have a new way for people To reach a market and sell a product that could be life changing for a small entrepreneur.

11:40 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.

11:51 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. and daycare. And they need that flexibility. They need that source of income.

12:07 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

12:21 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

12:38 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

12:54 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.

13:06 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 gonna go start something else and I'm gonna build this company because

13:22 I really feel like it's the right thing to do. And this is my calling. So answering a call. To adventure. Against You know, your parents.

13:32 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

13:43 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.

13:57 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. Where I overcame this challenge. But I'm so excited about living. I'm so excited about innovating.

14:13 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

14:23 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.

14:38 How did you emerge from what was a very Difficult childhood. With hope. and optimism. As key parts of your philosophy.

14:47 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.

14:57 That was literally my question. I was Turned out onto the street when I was Fifteen years old. I didn't have a job. You have to ask yourself

15:07 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.

15:18 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 the have faith and hope route every time. And it always worked out. It always did.

15:32 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.

15:43 It's a self fulfilling prophecy. Was there a moment? When you first remember making that explicit choice. Yeah, it was in that moment. So I became a ward of the state.

15:54 And they removed me from my mother's house. And they told me I had twenty four 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 twenty four hours, they were gonna put me in a group home. I've been in those group homes.

16:11 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.

16:29 Very easily in that moment I could have just sat there and succumbed to sorrow. to suffering. Two All of it. And

16:37 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

16:51 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 realise is that

17:05 Mm. 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 gonna 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? Like your description of that. When it happened

17:25 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.

17:36 That are the best there is at UCS at 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.

17:50 And so like when the students were coming and sticking lights in my eyes and lining up down the hallway because they've 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.

18:08 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

18:22 It's one of these things where You could either just say like this is it, I'm gonna die. And cry. Or you just say like You know what is

18:32 These are my last moments. I may as well make the best of them. So I did. And I honestly believe Granted you can't prove it. But I believe that that's what helped and aided in my recovery and why I recovered so quickly.

18:45 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.

18:57 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.

19:11 Minds. inside of us is a child yearning to be free. That's cosplaying as an adult. I think We uh

19:20 over time build our personality. We get told what we can and can't do. We uh wear certain clothes, they're just costumes, and 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 go out looking for them.

19:47 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 twenty seconds.

20:04 They're able to find them because their mind is not clouded with all of this. Frankly. Garbage that we grown ups carry around with us. And so for me, I'm constantly looking.

20:18 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.

20:35 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.

20:54 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.

21:07 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. Right. That's right. That's exactly right.

21:27 If you actually think about what you are. We are An animal. When we die. We decompose and we become

21:36 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.

21:47 To build things that yearns to change the world. That Wants to have a purpose for being here. And we deny that. Spirit, it's existence every day. I'm guilty of this. Everyone's guilty of this.

22:02 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 the my knees because Of the air. When the air hit my lungs and I was like

22:21 Whoa. What if I never got to breathe that again? How magnificent. And the sun was on my face and I was like, how splendid. That's what truly matters in the world. Like we

22:35 Make up all of these stories inside of our heads about what's important. But what's really, really important. Is Remembering

22:46 Just how precious life is. And how we have a short amount of time. Two accomplish all of our dreams and they're all accomplishable. And

22:58 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.

23:11 I would love to have multiple cyan agents out there roaming the world. Preaching the choir. Yeah, leading you know learning as much as a Possibly can.

23:21 So for me, my appetite for knowledge and for Everything is insatiable. So if I map some of this back to Piers. Amazing. one liner to you.

23:32 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 heated their calling? Is it Something about the person like

23:51 Walk me through the I'm sure feeling is hard to describe, but As best you can w how would you describe that skill of feeling? That Peter pointed out in you. If you think about it, business is just art.

24:03 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.

24:21 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.

24:35 I go to strange conventions that most of my colleagues would be like, Why on earth are you spending time at these places? But What I'm doing is trying to immerse myself among the general population of people

24:47 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.

25:02 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's sitting in front of me and they're giving me the pitch.

25:17 I start daydreaming and I start seeing the truth of what they're telling me. And if I feel it. And then the feeling I call my lightning bolts. It literally feels like a jolt of energy in my body.

25:29 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 it the person? Is it the opportunity? Is it the Timing. Has someone tried this before and failed?

25:45 Why is this person potentially the right person? Et cetera. And so Sometimes it's so overwhelming that I'm just like I've written checks on the spot.

25:55 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 twenty four hours and if I still feel the same feelings, then I make the investment. But

26:08 In general, it's this weird intuition. that this person is on to something And it could be big. For example, let's look at Pokemon Go, Nyantic. Yeah, I was gonna ask for an example, so perfect.

26:20 Yeah, and I went to work. I was working at Angelist 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 reskined. And instead of these portals that I was playing at. there would be these poke stops and then there's gonna be Pokemon around and everybody's like you're insane.

26:39 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.

26:51 And they continuously can't see it. And they came up with excuse after excuse not to invest in it, which was like Nintendo As a corporate investor, I don't do investing with corporate investors. These guys are spinning out of Google, or do they really have grit?

27:06 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 a ultimately a mapping company. not a gaming company.

27:20 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

27:35 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.

27:46 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 the argument and I try to see if it has merit. Like I said, don't be contrarian for contrarian sake.

28:00 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.

28:10 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 gonna get unusually good results by doing the same thing other people do. So the toilet paper convention makes lots of sense to me.

28:24 Do you have a favorite example of some unique input like that. Leading to an investment. That you made?

28:33 Uh 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 cars for me to get to the airport. And this was before

28:46 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.

28:59 You're just an amazing person. And he was an immigrant from Brazil. And just a really good driver and just I really like talking with him in the car. One day. I was going to the airport and he says, You know, I'm not an investor, Cyan, but if I was I would invest in this thing called Uber Cab, have you heard of it?

29:16 And I said no. I have it. And he said, Well I'm their only driver.

29:23 And explained to me how Uber Cam worked and I said Okay, 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?

29:39 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

29:50 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.

30:04 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 a hundred, hundred and fifty dollars just to get the car to leave the yard.

30:17 So they're already in the hole$150, right? So they're out there hustling trying to get that hundred and fifty dollars 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.

30:41 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

30:54 regulated by T C P 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

31:09 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

31:22 available and comes online to dry. And they said, Oh well Strangers won't get in. Strangers cars. And 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

31:35 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 try to invest outside of my ecosystem

31:54 I got hosed. I didn't know the players In New York or the players in Austin. Or you're up. And I couldn't get follow on financing for the companies.

32:04 That's all changed, especially since the pandemic and people have become remote. But then I was just like uh so I put Ryan Grave's card away. Fast forward. David Hornick has this Amazing event.

32:15 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.

32:29 And it's absolutely true. And It also happened in the swimming pool and the hot tub and various things when you're off site 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

32:44 There's this guy, Travis Kalinick, 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.

33:01 So I took stock of his 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 gonna watch this guy and see what happens.

33:18 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 Uber Cab like.

33:36 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.

33:46 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 COL.

34:01 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.

34:15 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 And new we're at. I believe that one's the alien.

34:27 Eight million. So that would have 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 just hit an all time high yesterday or something. Tell me about what that part of this is like. So there's the decision.

34:46 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 ten or a hundred X's, the pressure to sell something can be pretty high and then the thing ends up ten thousand Xing or whatever. So I would love to hear that side of this

35:04 Same story. You bought it, you're in at 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 invest.

35:16 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 a hundred employees. And then that disappears. And it's natural, every angel investor, every early seed stage investor should understand that this could happen.

35:33 Travis becomes more unreachable. Emile 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.

35:49 And so there's this period after a hundred 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

36:02 hope for the best outcome. There's very little you can do. You know, in the case of Uber, Krishaka 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.

36:21 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.

36:37 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.

36:52 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?

37:04 Yes. Yes. I actually think that It's best. psychologically for people

37:11 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 gonna move all over the place.

37:24 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

37:38 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.

37:57 So If you are Lucky enough. To have an exit. Of any material

38:05 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.

38:17 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.

38:30 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

38:42 Making a dent in the world. through capitalism. And I think Capitalism has like such a

38:49 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.

39:00 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. So

39:14 When I was younger, I actually felt that business people We're evil. And they were exploitative and All sorts of things. And I'm sure there are business people who are those things. But

39:26 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.

39:41 At a markup. And then I can reinvest that. into more supplies and make more money. And literally get off the street. And to me, that was like whoa.

39:52 Wow. Why can't everybody do this? Why can't they see this? And instead what they see is various abuses of capitalism. Capitalism itself isn't just an idea. It's art.

40:05 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.

40:20 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.

40:31 And I was employee number thirty. And it's the best company besides Founders Fun I've ever worked at in my life. The CEO there was incredible. His name is Scott Weiss. And He built

40:44 A true meritocracy of a 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.

41:00 And so I'm just like, give me more, give me more equity. That's all I want. I'll figure out a way to make in meat otherwise. And Because before that I worked at many startups and the equity didn't

41:12 turn into anything. every one of those companies ultimately failed. So when I had my first financial windfall was because Ironport sold to Cisco. For eight hundred and thirty million dollars. I think it was two thousand seven. I looked around to my friends and I was very fortunate to have made friends that

41:30 We're angel investors already. And my husband was an angel investor. had already been doing. Angel investments for ten years.

41:37 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?

41:49 And I was like, Okay. And he's like why don't you go out and look for opportunities. See what resonates with you. And come back. So I did. And

41:59 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 Noset came over to our house. Hell. is a dear friend of my husband's they went to college together, they dropped out of college together and

42:16 Drove west with walkie talkies. 'Cause they didn't have cell phones. And an apartment next to each other. Eventually Max lunch in the next door. But

42:26 He came over and practically got on his knees and begged us for money for SpaceX. And It was his conviction and his belief in Elon Musk. This love. That's undescribable.

42:39 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.

42:54 R Period at the end. This is NASA. End of story, the government will never allow him to participate. I put money in. I was like, you know what? I'm just gonna put everything in it.

43:05 Everything I made from Iron Port I put into SpaceX. And I was like, you know, I'm young. I can do this. I

43:14 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

43:28 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

43:38 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 space valuation is. You can kinda figure out they'd just blown up a rocket on the launch pad.

43:53 And they haven't figured that out yet and that can give you an idea of time. 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.

44:07 Then I'm gonna 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.

44:21 My chances of luck. Diminish. I think the fact that I have a North Star and so does my husband and we believe And things like Freedom.

44:31 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

44:44 It's possible that we are rewarded as such. Now obviously I can't Prove it. But I really, really believe.

44:53 that I am a steward of capital that I 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.

45:07 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.

45:22 My ego is a side. 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

45:36 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

45:46 I found the Beastie Boys and no one's ever heard the Beastie Boys and they're gonna love this. And I know I'm on to something, and for me Travis Kalanick is the beastie boys. It's totally fascinating. I 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

46:02 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 and what

46:15 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,'cause 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.

46:36 I had a lot of free time to sit and reflect. Fine. I mean some people I hate to say that some people didn't have the time because they were obviously frontline responders, but I was fortunate enough to sit down and think of like why is this happening? Who am I? What is my place in the world?

46:50 And really, really Figure out The why. because for a long time I really felt like we're supposed to just be good people.

47:00 live a good life and make the best of it. And we just turn to Dust in the end. And that's all there is to it. But The one thing I never tried.

47:11 with 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

47:27 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.

47:47 Serotonin. Regulates a lot. Of how we perceive reality. I had a surge of serotonin. And this lightning bolt like no other. It was basically this surge of energy that went from the base of my spine out the top of my skull.

48:02 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

48:16 I realize Everything around us is A projection of our perception minds. We when we're born, when we are born would come online with like going back to parts work and things like that.

48:29 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.

48:39 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.

48:50 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.

49:02 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. But 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

49:19 thing when you spin it up in your mind creates All kinds of hormones that get released. shape your reality and how you see the world.

49:29 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

49:39 I believe that consciousness Is Kind of like an operating system. And It

49:46 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.

50:06 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.

50:17 What matters is literally right now. And you hear people say this. And you wonder 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

50:32 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

50:44 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 B. And once you learn to have just to be, life gets a lot more simple. All of a sudden, everything you ever wished for.

51:00 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.

51:13 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.

51:26 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.

51:44 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.

51:55 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 twenty years ago.

52:10 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

52:21 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.

52:34 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.

52:44 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

52:53 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?

53:09 Like him. Put themselves. into the general population like that. And I identified with it. I told you earlier. I go to these conventions and I Put myself.

53:21 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.

53:41 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

53:54 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.

54:08 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.

54:20 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 Or A fun thing.

54:34 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. And

54:49 I think that I want Bill Murray to live forever. But When he leaves this Earth.

54:57 This go round. Tens of thousands. hundreds of thousands of stories of Bill Murray are gonna come pouring out. And that man's gonna look like a saint. He is a saint of sorts. You know, he's a very difficult person to work with, I've heard.

55:10 because he demands the best of people, he expects people to show up and give a hundred percent and His bar for talent and for art is incredibly high. But I can tell you how I met him. So

55:22 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 gonna get to ask him a question, just one question that's the most important question to me. If you do this. I guarantee you.

55:39 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 m mysterious ways. When I set out to meet Bill Murray I did not have money. When I met him, I did.

55:54 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.

56:08 of golf with Bill Murray. And I was like, what on earth? No way. And I was like, I'm in a position where I could buy this. Do I do it?

56:20 And so I said, Yes, I do. This is my chance. This the universe has 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 didn't knew nothing. I had never gone out to golf in my life. I actually have pretty

56:41 negative opinion of golf. I thought it was Poity toity and only for wealthy people and It just was not for me. And so I reached out to them and I said

56:51 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?

57:09 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.

57:18 To is an amazing man. Just absolutely amazing man. For the first ten 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.

57:33 And a little over half of the day later, he comes over to 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? You're playing golf with me. Cause 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.

57:57 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?

58:07 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.

58:20 All of a sudden he points to the hill and he goes Turkey. Ha. And I go, What? And he points to the hill and he goes, Turkey. And I was like, okay, turkey.

58:30 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 a tree, tree.

58:48 And I was like, yeah, that's a tree. And it became very clear he wasn't gonna 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.

59:03 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.

59:16 But Later on when I reflected on the day. I realize he did answer me. I got my answer. It was just an incredible valuable lesson.

59:26 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.

59:39 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 four. Since I was eighteen 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.

59:58 Wherever we went. 'Cause 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 player's here. Have them play. It'd just be a centric and odd.

1:00:10 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

1:00:20 There's a young man Boy. He was sixteen years old. Fifteen maybe. playing a violin and it's so beautiful and he's busk in the middle of this conference. And in front of his violin case, it says raising money for a certification course.

1:00:37 I asked him, I said, How much do you need? And he's like, I need two thousand dollars to take this class. And I said, Oh okay. And I said, Huh. And then I turned to Michael Tiffany. And we start rocking it, it goes, Are you thinking what I'm thinking? And I said, I'm thinking personal violin player for the day. What are you thinking?

1:00:53 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 gonna pay for your class.

1:01:08 But here's the deal. Are you willing to follow us around all day and just play music for everyone? Wherever we go. 'Cause 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.

1:01:23 But they absolutely love that he's 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

1:01:39 The Imperial Death March where he would play game of Pro and You know, and it was just really fantastic. And It changed his life. He was able to take that.

1:01:49 class and he changed our life. And it was just Miraculous and beautiful and and it just goes to show. You can do these things. We can all create magic in the world.

1:02:01 for other people and for ourselves, if you think about a situation and you act in that moment. Y 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.

1:02:19 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

1:02:30 long term ventures 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.

1:02:45 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

1:03:01 A lesson. as you go forward and then internalize those lessons. What did I do wrong? What did I not see? It was it out of my control. Did I still do the right thing, but then it was the wrong timing, et cetera, et cetera. And then you hone that into your gut feeling.

1:03:18 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 Fun, obviously was on the investment committee there. I've seen many, many, many deals.

1:03:32 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 Founderson, I joined Lee Jacobs at Long Journey Ventures.

1:03:46 And He's A decade younger than me. He's just starting out. And hitting his stride.

1:03:54 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.

1:04:08 And so my job is to Hopefully. Help him and inspire him. Two One, I have no doubt he's gonna be wildly successful.

1:04:20 Same thing with Arielle. 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.

1:04:31 you can make a real dent in 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?

1:04:49 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.

1:05:05 It's not about opportunity cost. 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.

1:05:22 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

1:05:33 That's all I want to focus on because I just want To make a venture firm. That's gonna be around long after I'm dead. And

1:05:42 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

1:05:54 thesis around investing is the combination of the three of us, but my spirit is definitely in there. Founder Sun has a spirit. It comes from Luke Nosak. who was one of the original founders of Founders Fund. He dared.

1:06:08 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

1:06:19 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.

1:06:31 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.

1:06:44 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?'Cause obviously we all want it to succeed. He laughed, he said, Well

1:06:58 the attribute that we want is that they leave them alone. You know, we believe that most of these investors are kinda 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.

1:07:13 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 like 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

1:07:33 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.

1:07:43 Yeah, my philosophy isn't quite as far as founders funds. Founders fund is like we invested in you and now it's you're on your own. And it's your job to extract value from us. A certain founder loves that. Because

1:07:57 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 Into the spectrum.

1:08:09 We um Are more hospitality. oriented because I think at the seed stage Being hospitality oriented is important. What that means is

1:08:19 One of our values is be a bubby. Bubbies are grandmothers who Give you hard advice. But they love you. And so

1:08:28 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.

1:08:39 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 The 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.

1:08:56 and giving that feedback just like a bubby would do. 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.

1:09:09 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 gonna tell you when things are not going right because They want you to lean in and help.

1:09:26 We wanna 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.

1:09:41 And presence of mind and things like that with our founders. We think that all the rest of it Is gotta be a core competency of the company, right? Like we're not gonna help with marketing, we're not gonna help with the hiring and or any of these things.

1:09:55 Unless we 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 gonna go out and be recruiters. All of that needs to be core to your business. And I think that's what truly matters.

1:10:08 Especially at the early stages. One of the things that Justin Mares told me to ask you about was integral family systems. I'm fascinated to know. What you've learned there. So I was talking to Justin and My partner.

1:10:21 And they said. you really should look into IFS and Try it out. So then I tried it out. And I went in Skeptical?

1:10:29 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.

1:10:46 And 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

1:11:01 They're 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

1:11:13 some behaviors that I thought were unchangeable. Through IFS. Nervousness, types of nervousness, types of reactions to People talking to me. And

1:11:25 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 in general, it's usually all about

1:11:39 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.

1:11:52 Do you still feel fundamentally flawed in any way. Absolutely. Absolutely, I feel flawed. You're gonna hear people talk about when they talk about spirituality about being asleep.

1:12:04 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.

1:12:21 In the moment. And so that's something that I want to grind away at and fix over time. I think that sometimes I can

1:12:32 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 were an infinite being

1:12:43 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.

1:12:57 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.

1:13:14 This is kind of a weird one, but If you had in a checking account. One trillion dollars. What would you do with it?

1:13:23 I would disrupt the Hollywood industry. I would reimagine The studio system. And I would build a company around it.

1:13:34 Say more, why? 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

1:13:48 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 the span engagement. So they couldn't Get money from

1:14:00 public appearances and things like that. Along came Michael Obits. and turned that on its head and created something called CAA. I just had him on. It was a very fun episode. And Michael Ovis is the best. I love that man.

1:14:12 And he reimagined how an industry could operate and he put the power back in the hand of the artists. That's why it's called the creative artists agency. And He fought for these artists and basically started packaging these deals. that were full packages where they developed everything and then work with the Stadios on financing and distribution.

1:14:31 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. You know in the beginning they

1:14:45 were pretty short sighted. They thought that D B D's coming in the mail was like the holy grail. They didn't See we're the evolution of this thing was going. kinda like Napster disrupted the music industry and we ended up with Spotify. We haven't ended up with

1:15:00 a new model for how Studios o operate. We're starting to see some interesting things happening with like NFTs and Web3. and distribution techniques for content that have never been tried before.

1:15:15 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.

1:15:28 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

1:15:39 Are dumbed down. Uh General audience appeal. They're made to make the most amount of money possible, but they're not made.

1:15:48 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.

1:15:58 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

1:16:09 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.

1:16:26 That should be okay. And the fact that we're not alarmed by this. to me is kinda nuts. I would want to bring transparency to accounting in the studio model. to where everybody understands the waterfall.

1:16:40 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

1:16:54 And we have A lot of upside. protection. You know, so the later investors come in. And save the day of the company.

1:17:01 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

1:17:17 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 the ideas have to flourish. I'm a first amendment

1:17:33 Nice. I donate money to the U CLA. Anarchist Brief Clinic down in LA and I'm very, very, very

1:17:42 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

1:17:52 To go after Hollywood, the next thing would be 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.

1:18:03 Because this is how we let out theme about what's going on in the world. We're all too sensitive right now. Everything is offensive. We gotta stop being so concerned about the words that people are saying.

1:18:16 And learn to think for ourselves instead. figure out what our inner voice is, our true north is. And then it doesn't matter what people say. It shouldn't even hurt you. I would say that. A trillion dollars is a lot of dollars.

1:18:28 It's meant to expand the mind. Yeah. I mean I probably would Try to work on legalization of Mind expanding substances.

1:18:37 MDMA. Pelocybin. Et cetera, probably put more money to work behind that. I probably would try to work on Incarceration rates.

1:18:46 People that are in prison for Pauses that cause no harm to anybody. To free those people. I probably would plow a majority of it back into startups.

1:18:57 If I describe you, one of the things I'd probably say is Every time I see a text from you, I know it's gonna be Something interesting that you've uncovered. It's almost like dispatches from the future or something is how I think about it. Yeah.

1:19:10 And I would love to know just as we wind down What fun dispatches from the future you're seeing today. Jin Z and Gin Alpha are incredibly freaked out right now about AI. Rightfully so.

1:19:24 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? But 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 gonna generate code and create apps just because someone dreams of it? Like why am I learning?

1:19:45 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

1:19:58 Nothing is gonna 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.

1:20:13 Lady's illustrated primer, right? Yeah, exactly. So We're heading into the diamond age. borders of countries are being questioned. Democracy itself is being questioned.

1:20:24 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.

1:20:42 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.

1:20:58 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 paint brush. Now they can take that idea. and synthesize it into something that people can see.

1:21:10 and express themselves in ways they never were able to in the past. Now Did they not spend ten thousand hours honing that craft? For sure. But

1:21:20 Does it make them Not an artist. No. So My dispatch from the future definitely is gonna be around

1:21:29 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

1:21:40 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.

1:21:56 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

1:22:11 I was hitchhiking on the side of the road. When I was seventeen, sixteen years old, I think I was sixteen. In Albuquerque, New Mexico. And I'd gotten kicked out of Denny's because I overstayed my welcome in there with the bottomless cup of coffee. It was in the middle of the winter.

1:22:27 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.

1:22:38 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.

1:22:52 Not you. He pointed to my boyfriend, which was kind of mean. And he said, Uh-huh. And he said, but since you're with her, just get in. And so they

1:23:01 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.

1:23:20 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.

1:23:34 thinking that it was crazy that he was getting this lightning bolt. Going back to lightning bolts. To save my life, but then he was just like, I realize if I don't stop, she's going to die. And so He saved my life and I'm so thankful to him.

1:23:48 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 active Giving to a complete stranger. And listening to his gut feeling.

1:24:02 that I'll never forget. Hm. Wonderful closing story. Thank you so much for an awesome conversation and for all your time. Yeah, thank you. Um

1:24:12 If you enjoyed this episode, check out Join Colossus.com. There you'll find every episode of this podcast complete with transcripts, show notes, and resources to keep learning. You can also sign up for our newsletter, Colossus Weekly, where we condense episodes to the big ideas, quotations, and more, as well as share the best content we find on the internet every week.

What you see above is a preview of the first minutes. One unlock costs 10 credits and covers this episode forever: full segment and word-level timestamps on this page, plus .txt, .srt, .vtt and word-level JSON downloads, as many times as you like.