Investing Like A Mystic: How Cyan Banister Finds Outliers (Co-Founder of Long Journey Ventures)

Cyan Banister https://cyanbanister.com/ has built one of the most distinctive early-stage track records of the last fifteen years, with early bets on companies like Uber, SpaceX, DeepMind, Niantic, and Postmates. Today, she is co-founder and general partner at Long Journey Ventures https://www.longjourney.vc/, where she backs what she calls “magical weirdos.” Banister describes herself as a professional daydreamer, running constant thought experiments and paying close attention to signals others ignore. In this episode, she explains how that mindset translates into investing, and why many of her best opportunities have come from observation, curiosity, and a willingness to look in unlikely places. In our conversation, we explore: Cyan’s philosophy of treating life as a series of experimentsThe strange, profound experiences that led her to question and ultimately move beyond her atheismHow scanning Wi-Fi networks in a Four Seasons café led her to Flock Safety, last valued at $8.4 billionLong Journey Ventures’ “Biz, Tizz, and Rizz” framework for identifying exceptional founders and why the trifecta is rareHow AI will enable the age of the polymathWhy she believes brain-computer interfaces are closer than most people thinkWhy she says Pokémon Go was “the closest we ever came to world peace”Why she lives part-time in a retirement community and her vision for a more connected future— Thank you to the partners who make this possible .tech domains https://go.tech/thegeneralistnl: An identity for builders at their core. Brex https://www.brex.com/mario: The intelligent finance platform. Persona https://withpersona.com/generalist: Trusted identity verification for any use case. — Transcript: https://www.generalist.com/p/investing-like-a-mystic-cyan-banister — Timestamps (00:00) Intro (03:51) Never playing the game you appear to be playing (07:18) Practicing childlike wonder as a daily discipline (10:08) Questioning belief after her stroke (13:30) Cyan’s metaphysical experiments (23:24) Non-local consciousness and creativity (27:22) Investing with extreme openness to signals (29:05) The importance of timing in investing (32:26) Meeting Travis Kalanick (34:19) Finding Flock Safety through a chance encounter (38:23) The summer of Pokémon Go (what worked and what didn’t) (39:55) Human nature and what makes something "stick" (42:15) Brain-computer interfaces and AI’s accelerating effect (52:53) “Biz, Tiz, Riz:” her framework for evaluating founders (59:20) Why Cyan lives in a retirement community part-time (1:03:50) A unique way of finding books that speak to you (1:08:44) Final meditations — Follow Cyan Banister: LinkedIn: https://www.linkedin.com/in/cyanb X: https://x.com/cyantist Newsletter: https://uglyduckling.substack.com https://uglyduckling.substack.com/ Website: https://cyanbanister.com https://cyanbanister.com/ — Resources and episode mentions: https://www.generalist.com/p/investing-like-a-mystic-cyan-banister — Production and marketing by penname.co https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Mario Gabriele?

  You've been one of the best investors, I would say, of the past 15, 20 years. Your track record is truly astonishing. You know, SpaceX, Uber, Pokemon Go.

• 0:08Speaker 01

  But what I'm doing is taking in all the sensory input around me and watching everyone's behaviors. The companies that have had the largest returns in my portfolio came from the most unusual places. Uber came from thinking about the taxi medallion system. I didn't come up with the idea of Uber, but I knew there was a problem. I knew there was a racket and there was a bottleneck, which was only a certain number of drivers can exist because it's throttled, and that's a problem. Whenever you notice humans' obsession, pay attention. You know, Pokemon Go, that happened because I noticed my friends playing this game called Ingris, and they were obsessed with it. And I thought to myself immediately, this is my one and only chance to invest in something I think is going to change the world. Eventually, you'll be able to vibe products, like physical objects. Like vibe manufacturing is going to be a thing.

• 0:53Speaker 01

  Million dollar idea you've been sitting on for years, you can now take it on Shark Tank. And I think we're going to have so many newly minted millionaires across the world. It might not be venture scalable companies, but they're going to be life changing for those families and create wealth that has been unprecedented in those communities.

• 1:18Mario Gabriele?

  Cyan Banister has written that she is never playing the game, but she appears to be playing. At 15, that meant sitting on the curb reading Kurt Vonnegut to capture an older crush's attention. Today, it's an apt description of how she's built one of the most successful investing track records of her generation, with early checks into Uber, SpaceX, DeepMind, Niantic, Postmates, and Android, to name just a few. Cyan now co-leads Long Journey Ventures, a fund dedicated to backing tech's magical weirdos. In our conversation, Cyan shares her evolution from lifelong atheist into a believer in non-local consciousness, her job as a professional daydreamer, as she describes it,

• 2:02Mario Gabriele?

  and why brain-computer interfaces are primed to break out over just the next two years, in her view. We also cover why she's building a drive-in movie theater for golf carts and the Somerset Ma'um novel she thinks everyone on Earth should read. I'm Mario and this is The Generalist. This episode is brought to you by .tech domains. I spend a lot of time speaking with founders and builders who are building the next generation of technology companies. For all of them, finding a compelling and distinctive company identity is essential to breaking through the noise. That starts with a great name and a great domain. That's exactly the thinking behind .tech domains. For companies building in tech, a .tech domain gives your project

• 2:45Mario Gabriele?

  a clean, confident identity from day one, instantly communicating what you're building. Nothing.tech, 1x.tech, Aurora.tech, CES.tech? The list of companies choosing .tech is growing quickly. It's not surprising that many venture-backed startups secure their .tech domain early. If you're building a technology company, it's worth thinking about how you want to show up from the start. Secure your .tech domain today from any registrar of your choice. This episode is brought to you by Brex. If you're a founder, the hardest part isn't the idea. It's scaling fast without getting buried in back office work. That's where Brex comes in. Brex is the intelligent finance platform for founders. With Brex, you get high-limit corporate cards,

• 3:29Mario Gabriele?

  easy banking, and high-yield treasury, plus a team of AI agents that handle manual finance tasks for you. They take care of things like expenses, all according to your rules, so you can move faster while staying in full control. One in three startups in the US already runs on Brex. You can too, at brex.com/mario. Well, Cyan, I've been looking forward to this for an extremely long time. I remember you being sort of one of the first people who I thought seemed extraordinarily interesting when I first got interested in tech and venture capital many, many years ago. And you've managed to remain equally, if not more, interesting as the years have gone by. So yeah, when I think about people

• 4:14Mario Gabriele?

  who seem to occupy different pockets of the future, you are certainly one of them. So thank you so much for being with us.

• 4:20Speaker 01

  Yeah, thank you for having me. The honor's mine. Thank you.

• 4:23Mario Gabriele?

  Yeah, there's so many things I'm excited to chat about today. Your past as an investor and present as an investor, some of your thoughts about the future, and also your writing. You are a wonderful writer, and you've been working on a memoir that you've been sort of publishing bit by bit. And it's actually there that I wanted to start because there were so many interesting lines in some of your pieces that seemed like they revealed part of your personality. And yeah, there's one in particular that I have been mulling over. It's in a piece where you're talking about being 15 and sitting on a, I think, a curb, reading Vonnegut books and waiting for an older crush to notice you.

• 5:05Mario Gabriele?

  And you have this line, which is that you're never playing the game you seem to be playing.

• 5:10Speaker 01

  Yes.

• 5:10Mario Gabriele?

  I wondered what it was that made you someone who always is, in some sense, obfuscating what you're after or the game that you're playing.

• 5:19Speaker 01

  Well, let's run a thought experiment. If life is a game, and again, this is a thought experiment, all games have rules, right? And so if you wanted to figure out if this reality that we live in is operating in some unusual way, the best way to figure that out is to run experiments and to do everything you're not supposed to do. So if you think about human beings, they're mechanical by nature. And so we get into our routines. We wake up in the morning. We walk the same way. We drive the same way. We find these things that are comfortable and we define them as our personality.

• 6:04Speaker 01

  We say that that's just how it is. But what happens if you start rolling the dice? What happens if you start, you know, instead of going left, you go right? Instead of wearing pants, you wear something ridiculous. You know, what happens when you really shake up life? And for me, that has always been a guiding light for me.

• 6:27Speaker 01

  And I keep a lot of these thoughts secret because I want to see if I do something, what's the outcome of it? What happens? And if I reveal it to everybody all the time, then

• 6:41Mario Gabriele?

  Yes.

• 6:42Speaker 01

  Then you know that that kind of defies the purpose.

• 6:45Mario Gabriele?

  Yeah, you you tilt the experiment if you if you share too much.

• 6:49Speaker 01

  And in that particular experiment, I got the guy, right?

• 6:52Mario Gabriele?

  Yeah, it worked out. And you read a lot of Vonnegut, which, you know, win win.

• 6:57Speaker 01

  Exactly, exactly. So I sat there and read a lot of Vonnegut. And it helped that I kind of had an inkling that he liked Vonnegut. But, you know, eventually he did notice me and then it all worked out.

• 7:09Mario Gabriele?

  You know, I think that idea of almost remaining, you could call it playful or childlike or open minded. You know, it's one of those things that I think adults struggle to maintain. You know, we, our brains sort of lose their plasticity over time in some sense. If you're if you're not careful, like, I don't know. Have you had to make a really conscious decision to keep pushing those boundaries for yourself? Or keep running these experiments so that it doesn't calcify?

• 7:40Speaker 01

  Yeah, I mean, it's a daily practice. You have to weave it into your life. You have to really not take yourself too seriously. We tend to do that. We tend to cosplay as adults. And I think if you add a little bit of play and wonder, if you look at children, especially in early childhood, they're limitless. They don't understand a lot of boundaries of thinking, of their environment, and they're just in explorer mode. And everything is a new sensory experience, like experiments, right? And so I look at the world that way.

• 8:19Speaker 01

  For example, today and yesterday, I've been running the thought experiment of if I'm in an avatar, it always starts with if, you know? If I'm in an avatar and I get to have this one human body for a period of time, and let's just say I'm a limitless energy being inside of it. There's only so many breaths. There's only so many leaves. There's only so many tears. There's only so many frustrations I'm going to experience. And so when I think about that and I close my eyes, I'm so grateful. And I'm filled with so much joy. I recommend that everybody try it.

• 9:03Speaker 01

  Like go outside and be like, wow, I may not feel arrogant. Like it's pretty great, you know, and that will lift your spirit immediately and invite that childlike wonder in. If you just stop and pause for a moment every day. So for me, it's a practice when I wake up. The first thing I do is wiggle my toes. You know, it's kind of like a boot sequence. You've got to be like, okay, I've got this hardware. I'm gonna wiggle my toes, I'm gonna wiggle my fingers. I write things on walls. I write things around my house. That help remind me. Uh, because I am mechanical, just like everyone else.

• 9:44Mario Gabriele?

  Yeah.

• 9:45Speaker 01

  I fall into my routines. I fall, I start thinking too much about the future or I live too much in the past. And I need something to just kind of shake me awake. And so I recommend if people want to start doing this, you know, the shower is a great place. You can write. Something on the glass. It fogs up. You can remember to be more full of wonder every day.

• 10:08Mario Gabriele?

  Hmm. How, how did that sort of spiritual philosophical posture come to you? Was that something you were? Uh, I don't know, uh, raised in, in some capacity, even if it's been transmuted. Is that? You know, I know you've spoken before about having, you know, a sort of profound awakening, uh, after a stroke. Like, was it, you know, more tied to that? Well, where does that come from?

• 10:31Speaker 01

  All of the above. So I was raised, uh, exposed to just about every religion you can imagine. So my mother. Was deeply trying to find herself and her purpose and why we're here. And so, and then there was also free childcare. So, uh, we got dropped off at, um, you know, I was a Mormon. I was baptized Mormon. I went to catechism. I've been a Baptist and baptized Baptist. I had a Muslim stepfather. Uh, my mother was also, um, part of the Native American church. And so I ended up out of all of that experience, becoming an atheist. However. The childlike wonder was not.

• 11:15Speaker 01

  I didn't think of it as spirituality. I just thought about it as a way of living and a way of surviving. Which is if you've got to get up every day and you've got to go out that door and you've got to make something of yourself, you may as well have fun. You may as well figure out some way to spark joy in yours and other people's lives. So for me, it was fundamental to just my being. And if you talk to anybody who's known me for a long time, I've always, I had very little. I was very poor. And so the other thing is like, how do you maximize fun and happiness with very little money? So I was always the friend, um, and there's a couple of us, but

• 11:57Speaker 01

  who would try to come up with something really fun and inventive to do on a Friday night that costs very little. You know, and maybe it's playing a prank on a friend, or maybe it's calling two people together and having them talk to one another in a three-way call in the middle of the night, or maybe it's, you know, it's, it's endless. But, you know, that was part of my personality, but spirituality really opened it up. And I had a very profound experience. It wasn't exactly related to my stroke. The stroke started it. The stroke started the question, which is, what is all this about? You know, where, where does suffering come from? What is the purpose of suffering if it, if there is one?

• 12:41Speaker 01

  And that thought experiment lasted several years. And I asked myself, have I been really, really honest about spirituality? Or have I just dismissed it because of my childhood? And have I ever believed any of it? And the answer was no. I never believed any of it. So how does one believe? How does someone get there? Like, how, how do you trick your mind or convince yourself? An invisible world.

• 13:15Speaker 01

  You know, that no one and you can't see. But I can tell you that once I got there, for a series of experiments, I started seeing things, experiencing things that are just bizarre.

• 13:31Mario Gabriele?

  You became more of a magnet for weird things after being sort of, as you say, tricking yourself into becoming a believer?

• 13:40Speaker 01

  Yeah, my life was already bizarre and weird and magical. It became more so, right? Like, let me give you some examples. This one is probably the most profound. Can I tell you the most profound one? The crazy one?

• 13:51Mario Gabriele?

  Please, yeah.

• 13:52Speaker 01

  I was listening to something called the telepathy tapes. And if you haven't listened to it, I highly recommend it.

• 13:57Mario Gabriele?

  For folks that don't know what that is, would you mind giving a praisey?

• 13:59Speaker 01

  Absolutely, yeah. The podcast is about parents who are, who have children, both adults and underage, who have autism and are nonverbal. And in many cases, also have no, no ability to move their bodies. And so, or it's very limited. What they discovered was that these children were able to find things that the parents hid over and over and over again. And so at first they thought, well, they have superhearing, you know, the ones that can move around and see and look for things. And then they realized, no, it's not that.

• 14:41Speaker 01

  It's, it's because they would, they would do it outside of the house. They would conspire the parents together to hide the candy and the kids would still find it. And so they developed this, you know, hypothesis that perhaps the children were psychic. So what was interesting was that they started displaying characteristics that were off the charts, like math that they shouldn't know, that they never went to school for, languages that they never went to school or studied for. In one particular case, there's a gentleman who could recite novels, but had never read.

• 15:17Mario Gabriele?

  Wow.

• 15:18Speaker 01

  How do you do that? So I started thinking about that and I wrote down every episode and I started writing down the commonalities between each of the people. What were the stories that were the same over and over again? The number one thing was they all claim that they have sacked or met God, sat with God or met God.

• 15:38Mario Gabriele?

  Oh, wow.

• 15:39Speaker 01

  So they all claim that there's a metaphysical school that they all go to. So at university that's metaphysical. They all claim that it's individualized to each person. And so, for example, there's one kid who said that if he wanted to learn anything about anyone like Aldous Huxley, he just pulls Aldous's hat off of a wall and puts it on. And he knows everything about what Aldous thinks or did or wrote. And that's how he experiences reading a book. And I was like, wow. And what blew me away more than anything was that they 100% all of them meet in this place called The Hill.

• 16:23Speaker 01

  It's a place that has green grass that thousands of them congregate at. Um, at one point, the host asked how many people are on the hill right now? And they just spat out a number, 2,173. I was like, what? And you can't get into this space unless they allow you into it. Moderator of some sort, or they're all moderators. You have to show up there with the right intentions. Now, there's a lot of things, if you want to think about this as a scientist, obviously, social contagion is a thing.

• 16:55Mario Gabriele?

  Yes.

• 16:55Speaker 01

  You know, they're all on Facebook. All the parents could conspire, they could share stories. There's a quality to it that just feels there's something there. And so I started running my own experiments. And I started targeting people in my life. And I just went to Spotify and just typed in, send a telepathic message to a friend.

• 17:20Mario Gabriele?

  Spotify.

• 17:21Speaker 01

  Like, I don't know what I'm doing, try this. And so I found this thing called intuitive hour. And um, I tried to send a message to someone I have not talked to in a few years. And I thought, well, if this person responds to me, that's just a bona fide miracle. I did it and within 15 minutes, I got a text message from that person. And what was really interesting was that he responded to something three months prior that was completely non sequitur. So it was not like the last message we had. It was something from three months ago. I fell on the ground and started crying because one, I miss this person dearly and I wanted them back in my life.

• 18:01Speaker 01

  Also, it may have worked. And I say may have because I'm not a scientist, but I am a scientist.

• 18:08Mario Gabriele?

  Yes, a scientist, yes.

• 18:10Speaker 01

  Scientist. And so I was like, well, you gotta try it again and again and again and again. So I tried different experiments. I tried sending a message to someone that I don't get along with too well. Now here's the weird one. So I did that one and I got a call from my best friend in New York, not the person I sent it to, who said they were sitting in their living room. They said, what, what were you doing last night at 10 o'clock Pacific, one o'clock my time in New York? And I was like, oh, why? Cause I never say, I'm like, what? And they were like, well, I heard your voice outside of my head, which normally you hear things inside your head, but um, the voice said, are you all right? Are you okay?

• 18:53Speaker 01

  That is exactly what I sent to the woman who didn't get it. So I thought, hmm, if you are emotionally blocked or you have negative energy towards someone, maybe it goes to the nearest node of someone who loves you.

• 19:08Mario Gabriele?

  I see. That's, that's an interesting theory.

• 19:10Speaker 01

  Right? So I was charting all these things out and I was like, okay. And I was like, well, what happens if you send a picture to someone? What happens if you get a group of people to do it? So I got a group of people to do, I started getting witnesses for everything. I got a group of people to do it and we sent the image of a bird to a friend. And the next day I got a message from that friend that said that they were getting on a plane in Miami or Key West or something and suddenly saw a hummingbird in their mind and it, they thought of me. And so they're going to go get a tattoo of a hummingbird. And I was like, wow. So what does this imply? Right? I was like, this is insane that that I with these limited

• 19:53Speaker 01

  skills are able to continuously do this. Now here's where it's really going to blow your mind. So I'm down at a farm in Temecula in a grapefruit grove. And I'm watching a movie with a friend. So my friend was like, let's watch something. And I said, let's watch spellers, which is what the telepathy tapes is based off of is these. I highly recommend everyone also watch the movie spellers. Halfway through the movie, my friend Chris pauses the movie and he says, Cyan, do you think that animals are telepathic? And I said, well, here's the thing. I don't know. I don't know any of this, by the way. I'm not, I'm not claiming that this is real. I'm just saying, try it for yourself. And I said, you know, the telepathy tapes, there is one episode where there's an African gray

• 20:38Speaker 01

  and a human. It's human and they separate them into different rooms. They show the human a picture like say of a red ball. And African gray goes, red ball.

• 20:49Mario Gabriele?

  Oh, cute.

• 20:49Speaker 01

  Or go through a picture of a yellow car and it goes, yellow car. You know, so whatever she sees, the bird spits out.

• 20:56Mario Gabriele?

  Yeah.

• 20:57Speaker 01

  So just as I'm telling this story, all of a sudden we hear, help me. Help me. And I look at Chris and I said, what is that? And he's like, I don't know. My daughter and my wife have gone to bed. Maybe it's a toy that got left out. So we, we started looking around for a toy. You know, we don't find a toy. And I'm like, we have squirrels out there. We have, you know, coyotes, we have owls, we have snakes, we have nothing that makes that noise. And so he comes running to me. He's like, Cyan, Cyan, Cyan, you need to come here right now. And I'm like, okay, so we, we go to the front of the house. On the outside of the house, on the screen window is a pink cockatoo.

• 21:37Mario Gabriele?

  Wow.

• 21:37Speaker 01

  Saying, help me.

• 21:39Mario Gabriele?

  Oh, my gosh.

• 21:42Speaker 01

  I can send you a video of this. It's insane. And I was like, what are the chances? What are the odds?

• 21:50Mario Gabriele?

  Wow.

• 21:51Speaker 01

  This is the kind of stuff I'm talking about.

• 21:53Mario Gabriele?

  Gosh.

• 21:54Speaker 01

  Now, it took us three days to find the owner of that bird. You know, we named it Telly for telepathy because we thought it's a telepathic bird.

• 22:02Mario Gabriele?

  Yeah.

• 22:03Speaker 01

  And we found its owner, which was two farms down. So it's not, not a short distance. They came and claimed it and they said that normally this bird doesn't fly. And they have it in the garage and have it in the house and the windows are open and it never escapes. Like it's never done this. But one day they were in the garage and it just took off. And they thought it was dead. They were like, this is such a domesticated bird. There is no way we thought it survived. So this is a miracle that you saved it. And the other thing was that we asked, what is the name of the bird? Because we call it Telly and they said it's Mumbles. And I said, why is it named Mumbles? And they said, because it doesn't say as many words as a cockatoo should.

• 22:47Speaker 01

  It has a very limited vocabulary. And I said, well, is help me part of the vocabulary? And they said, no, that kind of stuff keeps happening. So that to me implies that human beings have capabilities that this may not even be supernatural. It may not need to be spiritual.

• 23:06Mario Gabriele?

  Yes.

• 23:07Speaker 01

  May just be natural. We might have the ability to communicate with one another or glean things from the environment and nature that we're just completely unaware of or detached from or don't understand how it works anymore. And that's because we're so distracted. It could be because of our ego. So the ego plays a huge part of it. You've got to think of the ego as software on top of the hardware. And the ego interprets everything that comes to it as I. This is mine. It originates from within. What if it doesn't originate from within? What if it's outside of us? So the thing I'm most obsessed with right now is non-local consciousness.

• 23:51Mario Gabriele?

  What does non-local consciousness mean?

• 23:53Speaker 01

  Many people have studied this and they said, well, it is kind of interesting that this happens, but it's not always repeatable. It's not, you know, you can't get empirical evidence on this ever. It's slippery. It always gets away from you. I suspect, I feel, because I've played with this enough and poked at it enough, that there is a collective sort of cloud of consciousness that maybe, I'm going to use some layman terminology here, sorry for all the scientists listening, the universe is conscious. I have no other word for it, but that we're all connected to this cloud of sorts and that you are a receiver.

• 24:35Speaker 01

  You're basically an antenna that waits to get information. And so if you talk to a lot of artists, like, let's look at the woman who wrote Harry Potter. She says that she was on a train and the entire story of Harry Potter was just downloaded to her in a flash and an instant. If you talk to a lot of musicians, they say the same thing. They say, I don't know where this song came from. I don't feel like I wrote it.

• 25:00Mario Gabriele?

  Yes.

• 25:00Speaker 01

  Same thing with novelists. You name it. There's people who said like, I have no idea where this came from. It just struck me in the shower. It struck me while I was driving. It struck me while I was walking. I've also been looking at BCI's, which is brain control interfaces. And a lot of these startups and these entrepreneurs are starting to discover that there's this really interesting stuff happening in the background in your subconscious that you are completely not privy to. So there's some startups that I've seen that are starting to spit out information that is two weeks old, like you thought about two weeks ago.

• 25:36Mario Gabriele?

  That is still visible in a BCI.

• 25:38Speaker 01

  Yeah, but not in your active, you know, thinking, not in your, what we would call consciousness, be subconscious, right? And not only that, but some of it is picking up on other people's thoughts around you. How's that work?

• 25:52Mario Gabriele?

  Yeah.

• 25:53Speaker 01

  I think in the next two to three years, we're going to figure it out. And when we do, you've got to think about, there's A dystopian view of it and a utopian view of it. Which is, that means it can be manipulated. That means that it can be used for dangerous and terrible things. But it can also be used for things that can uplift humanity. And bring us to our truly, truly creative selves that we're meant to be.

• 26:19Mario Gabriele?

  You know, I think the sign of a good conversation that there's a a lot of things that you said that I feel so skeptical about that now I have to go back to. And a lot of things where I'm nodding vociferously along with you.

• 26:31Speaker 01

  You should be skeptical. Anyone listening should be very skeptical. Okay. I started out as a skeptic, as an atheist. I got here through experimentation, through mysticism. I treat it like science.

• 26:44Mario Gabriele?

  Yes.

• 26:45Speaker 01

  I poke at reality. I ask a question and I go out and do things. And then I get these weird results. And so I recommend, don't listen to me and trust me. Like, go read this stuff yourself. Listen to these.

• 26:57Mario Gabriele?

  Yeah, run your experiments.

• 26:59Speaker 01

  Run your own experiments.

• 27:00Mario Gabriele?

  Yes, I totally, I like, I like that idea a lot. And I think I'm going to try. It's interesting. I, I never listened to the telepathy tapes. I read about them and I think I reached the stage at which I read about the sort of like Ouija board effect and was like, ah, okay, I've understood this. And clearly there's like three or four levels deeper that one can go to think about it. And so I'm excited to do that piece. And then you're, I think the, have you ever read the book Impro?

• 27:29Speaker 01

  No.

• 27:29Mario Gabriele?

  It strikes me that you might really like the discussion of creativity in that. It's from one of the guys who basically created the, the philosophy of improvisational comedy and theater. And he talks about how like Western ideas of creativity have become so ego focused. And so as a result, we become super blocked. Because we become so attached to like, what does it say about me that I did this thing? Like, does that mean I'm bad or dark or strange? And actually, you know, so much of creativity in many other cultures have a very different view, which is more of this like, I am a channel for something. And that's much more freeing. And I totally think that's true.

• 28:10Speaker 01

  Well, not only that, but we're always playing for an audience, right? Like, if you're creating for TikTok and it's not coming from an authentic center.

• 28:18Mario Gabriele?

  Yeah.

• 28:18Speaker 01

  Of who you truly are and you can feel it, you can see it. Even when I watch Instagram, I can tell if someone's putting on a show and it's a or it's really who they are.

• 28:28Mario Gabriele?

  Yes.

• 28:28Speaker 01

  And and so I think art used to be very different, you know, even in the the era of Saturday Night Live, early television, I think we were seeing some of that creativity, that rawness, you know, coming through. But now I feel like a lot of it is manufactured for a certain kind of viral outcome. You know, I I I can't say if it's good or bad. I have no idea in the long run how this all plays out. But I do think there's there's something to just letting go of the attachment to the outcome and allowing yourself to be a vessel for whatever comes through you.

• 29:06Mario Gabriele?

  You know, you're you've been one of the best investors, I would say, of of the past fifteen, twenty years. Your track record is is truly astonishing, you know, SpaceX, Uber, many others. How much of that do you do you attribute to what I would classify in this conversation as like an extreme high openness? Like, you you seem very open to any signal the world might give you, and then a desire to like verify it for yourself. But to me, that's almost one of the most underrated parts of a venture investor's job and kind of under filtered for when people look to, I don't know, hire people to an investing team. There's some version of a VC that people think, ah, you know, we want someone who

• 29:50Mario Gabriele?

  did two years at McKinsey, two years at Google, and then maybe a startup stint. And that really doesn't capture the level of imagination that's required.

• 29:58Speaker 01

  So I like to tell people I'm a professional daydreamer. So one of the things I like to do is carve out a significant portion of my week to sit and ask these questions and run these thought experiments, and then visualize what that future could look like in reality. You know, are there market conditions that could make that possible? One of my favorite science fiction authors, Neal Stephenson, told me, I got a chance to meet him, which I was really excited about. He told me, I said, how did you get so much of our future right?

• 30:29Mario Gabriele?

  Yeah.

• 30:30Speaker 01

  And he said, well, one is I'm a historian, so you have to understand the past. And two, you have to understand how the money is made. You can look to the future, and you can come up with a utopia in paradise, but if there's no way to make money in that utopia, it just won't happen because markets will drive things forward, right? And so that's how he figured out the diamond age and how he figured out snow crashes. He figured out the financial incentives, which is beautiful. I can't say that I've always thought that way and I've made some mistakes because of it. However, you know, timing is everything. I've been too early. There's I if I told you all the times I was too early, you know, um, it it'll make.

• 31:10Mario Gabriele?

  Is there one that's really painful? Like, what was the one that you were too early that really should should have worked? Or maybe we're just getting close to.

• 31:16Speaker 01

  I am part of Zivity.

• 31:18Mario Gabriele?

  Zivity, yeah.

• 31:19Speaker 01

  Which uh, basically um, invented crowdfunding and and patronage from for art. Ended up becoming, you know, I would argue that OnlyFans is probably the largest outcome of that. That economy, but here's another example of something that was too early that you can invest in later. Which is I was in love with this company called Cosmo. That did um, delivery of like cough syrup, candy bars, video games. And under an hour, but it was based in a warehouse and this was um, around year 2000, 2001.

• 31:53Mario Gabriele?

  Oh, wow.

• 31:54Speaker 01

  And they went belly up because they couldn't figure out how to make the margins work.

• 31:59Mario Gabriele?

  Yeah.

• 31:59Speaker 01

  Along comes Postmates. And they figured it out, right? Because you needed the iPhone. You needed the ability to give them provisioned credit cards. You needed the ability to that whole system had to exist in order for that idea to exist. So that's one of the things to look at. Every time you get pitched on something is now the time. What are all the things that are going to need to be in place for this to exist? And when do you think they're going to exist? The companies that have had the largest returns in my portfolio came from the most unusual places. They did not come from grinding and taking meetings back to back.

• 32:38Mario Gabriele?

  Yeah.

• 32:38Speaker 01

  Like Uber came from thinking about the taxi medallion system. I didn't come up with the idea of Uber, but I knew there was a problem. I knew there was a racket. And there was a bottleneck, which was only a certain number of drivers can exist. Because it's throttled and that's a problem. How do you disrupt that problem? I didn't have the answer to that, but you know, I met Travis at a boondoggle thing in Hawaii. And he wasn't pitching me Uber. I just happened to notice he was interesting, you know, and observed him.

• 33:11Mario Gabriele?

  What was interesting about him?

• 33:12Speaker 01

  Gravitas. He had this like natural born ability to lead. And no matter what you put him in, whether it be a hot tub or a conference room or at a dining table, he just took charge. He was clearly the leader of everything. And I, and he was on the bench at the time. He, he said, I just sold my company. I'm looking for my next thing to do. And if you're an investor, that should ignite part of your mind and be like, that's someone to watch. Right?

• 33:42Mario Gabriele?

  Yeah.

• 33:42Speaker 01

  So I just put a pin in it. And then a few months later, I saw him pitching at Open Angel Forum Uber cab. Now, keep in mind also, I had an Uber driver. My, my personal driver was driver, was driver number one for Uber. Another weird.

• 34:00Mario Gabriele?

  Oh, wow.

• 34:01Speaker 01

  Yeah.

• 34:01Mario Gabriele?

  Gosh.

• 34:02Speaker 01

  Um, and he kept handing me Ryan Graves' business card. If anything, the universe, if, if it was conspiring in my favor, was basically hitting me over the head. It was just like.

• 34:12Mario Gabriele?

  Not subtle.

• 34:13Speaker 01

  It was not subtle. And so is that incredible luck? Sure. If that was the only thing I ever did, then I would say, yeah, that was just luck. But then if you look at flock security, you know, one day I was at the Four Seasons before the pandemic and people used to have lots of meetings there. And I went there and again, like if you were to ask a lot of people about me, I tend to be very quiet and observant and you would probably describe me as a wallflower. But what I'm doing is taking in all the sensory input around me and watching everyone's behaviors and listening, deeply listening, not just the words, but all kinds of things. And so I went into the cafe and I looked around and I noticed everybody's busy wheeling and dealing and having their meetings.

• 34:58Speaker 01

  And so I ordered my coffee and I get on the wifi. And I noticed that on the wifi, everyone's tethered their phone in a public manner. So there's K pixel. And I was like, K's pixel. Hmm. I look around and I see Keith Raboy. And I'm like, oh, okay. He has a pixel phone, maybe. Hmm. So then I see Travis K iPhone. And I look over in the corner and lo and behold, there's Travis Kalanick meeting with someone. I'm like, this is a great way to get intel. This is crazy. So then I see Garrett Langley's iPhone. And I'm like, I don't know who that is. So I Google search him. And he is the founder of a company called Flock Security, which was in Y Combinator

• 35:39Speaker 01

  at the time. And I did not go to the demo day. So I didn't know it was coming up. I don't know if he pitched or, or what. And I remember a conversation, this is where observation comes into play here, right? A conversation at Founder's Fund where we were wondering, is there a camera solution that's crowdsourced of some sort that could eliminate or reduce crime? Should we look for a company like that? And we all agreed we should. So I messaged my intern at the time, John Ludig, who's now a partner there. And I said, John, what do you think of Flock Security? And goes, well, it's on my list of people of YC I want to meet. And I was like, well, he's

• 36:19Speaker 01

  just right across from me. And he's like, well, walk over there. Say hi.

• 36:25Mario Gabriele?

  Perfect.

• 36:26Speaker 01

  So I walk over and I'm like Garrett Langley. And he looks up at me and he's like, huh? And he's like, looking around. And I'm like, and I just, it was a bit of a magic trick. I said, I'm Cyan from Founder's Fund and we would love to meet you. And he's like, are you part of YC? Are you, are you doing the demo day? Like, how do you know who I am? And I was like, well, do you really want to know?

• 36:49Speaker 01

  And I told him and he blushed. And we were going to save this story for when the company went public, but I think it's safe to share it now. You know, John ended up coming and meeting with him too. And we ended up doing the investment and co-leading the Series A down the road. But that company, what is what valued at seven billion, eight billion or something at this point? And solves a huge percentage of the country's petty crime, like

• 37:14Mario Gabriele?

  Yes.

• 37:15Speaker 01

  bicycles and lawn mowers. And they also solves Amber Alerts and things like that.

• 37:21Mario Gabriele?

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• 38:06Mario Gabriele?

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• 38:24Speaker 01

  And so I think, you know, you have to be open to an opportunity presenting itself in the most unusual of places. You know, Pokemon Go, that happened because I noticed my friends playing this game called Ingris, and they were obsessed with it. And whenever you notice humans' obsession, you know, pay attention. Like, why are this, this early group of people, these early adopters, chartering helicopters?

• 38:54Mario Gabriele?

  Yes.

• 38:55Speaker 01

  What?

• 38:55Mario Gabriele?

  For this geo game, yeah.

• 38:58Speaker 01

  It looks like geocaching?

• 38:59Mario Gabriele?

  Yes.

• 39:00Speaker 01

  Um, and so I started playing it and I realized like, wow, this is amazing. If I could invest in this, I would, but Google owns it. Lo and behold, they spin out Alphabet, and I thought to myself immediately, this is my one and only chance to invest in something I think is going to change the world. And then when I found out that Pokemon was going to be involved, I was like, I went around to everyone saying, you don't understand. Everyone's going to be catching invisible Pokemon, and they're like, you're insane. No one's going to be looking at their phone. Nobody, if you remember, everybody's doing this.

• 39:31Mario Gabriele?

  Yeah, yeah, totally.

• 39:33Speaker 01

  And I would argue it was the closest we ever came to world peace.

• 39:36Mario Gabriele?

  It was a beautiful moment. I remember that summer very well. I mean, maybe it was longer than a summer, maybe it was, you know, eight or so months, but it really felt like for a moment, this was like one of the more wholesome uses of, uh, of technology and like, yeah, a, a really beautiful way of people finding these new connections. Why do you think that didn't stick as a, as a form factor?

• 40:00Speaker 01

  Human nature.

• 40:02Mario Gabriele?

  Hmm.

• 40:02Speaker 01

  So Pokemon Go is still quite large. They make billions of dollars. It's, uh, it's played worldwide. Um, it was acquired, uh, recently. And the company that acquired it also made Monopoly go, which is not geolocation, but it's, um, I think Monopoly would be a natural extension of the, of the technology. I would ask, actually talk about, why didn't Harry Potter work? Cause Harry Potter should be, that should be, you know.

• 40:32Mario Gabriele?

  Yeah, even bigger, right?

• 40:34Speaker 01

  And I think part of it was because the lore started when Harry Potter was an adult. And it should have started when he was a child. And it should have, there should have been a sorting hat. There should have been this magical experience of going back to Hogwarts for the first time. And instead, you know, for whatever reason, J K Rowling and Warner Brothers wanted it to, to start later in the canon. And I think that was a big mistake. And so if anything, I think allowing IP makers or holders too much control over the IP could be catastrophic. If you have an insight where you know that that's not how it should go.

• 41:13Speaker 01

  But that's probably why I posit, I don't know for sure that, you know, that didn't work out. But Pickman Bloom is still doing incredibly well. Anything that's like rooted in Japan, really, like, uh, has a global application. Like there's something about Japanese culture that translates really well in this regard. The question I have is why hasn't there been another one? And I think human beings are, we love novelty. And we love to try new things, but to make something stick for a long, long time. It's just very difficult for us because of dopamine. Because our bodies are wired and trained, but there's some people who still use Pokemon to get out and walk,

• 41:58Speaker 01

  to get out and meet friends. They still go to the festivals, they go to the meetups, they go out on special Pokemon days and catch special Pokemon. It's still happening. It just looks a little different and it's not as prolific as it was in the first year. And so I think that's why people think it vanished, but it didn't vanish.

• 42:16Mario Gabriele?

  I suppose the part that's interesting to me is that like that hasn't been more of a launchpad for like a whole new range of of experiences beyond even Niantic, right? Like the the more people haven't sort of taken the Pokémon Go.

• 42:31Speaker 01

  Hard problem. I think people didn't realize how hard it is. They thought it was super easy, but I'll tell you what the hard part is, is understanding where a human can walk and not walk. I don't know if you remember, but there were people catching Pokémon in police stations.

• 42:44Mario Gabriele?

  Yeah.

• 42:44Speaker 01

  And the police are like, no, no, you need to geofence this.

• 42:47Mario Gabriele?

  And on baseball fields and all these sorts of, you know, on professional stadiums.

• 42:51Speaker 01

  Exactly. So running into stores that they are even people's yards, you know?

• 42:56Mario Gabriele?

  Yes, yeah.

• 42:57Speaker 01

  Figuring out that piece was probably one of the hardest parts and nobody owns a better map of that than Niantic. So my insight, Niantic, was not that it was a game. You know, the the founder of Niantic, John Hanke, also built Keyhole and worked on Google Earth and Maps. And so the way that I thought of Niantic is it's a mapping company at the end of the day. And so Niantic Spatial, I think, is going to prove that out in the end. So it's now a separate company and they don't do games anymore, but they do, they're continuing on the mapping. And I think that's wise. I think it was a very good strategic move on their part.

• 43:35Mario Gabriele?

  Well, speaking of a different kind of mapping, I'm curious to go back to the brain-computer interface thread. You mentioned, I think, you know, you expect us to have a lot more answers even in two to three years. What what do you expect to help us get there? Like, have you just seen?

• 43:51Speaker 01

  Yeah, the fact that we can take large amounts of data now and find interesting things in it that we couldn't do before without great expense, I think is really breaking things open. So all these entrepreneurs wandering around with spaghetti helmets is what they look like, these little things and and collecting data 24/7. And then, you know, there's thousands of people running these studies now. And so you're going to get information that was previously unavailable. And so that will enable a breakthrough of some kind. Every week I read about some new, like I just read about a hat that allows you to type.

• 44:35Mario Gabriele?

  I just saw the same thing I bet the beanie, right?

• 44:38Speaker 01

  The beanie. You'll be able to type without using a keyboard. And I remember I invested in Control Labs, which ended up becoming part of the Meta Rayband's, the gesture.

• 44:50Mario Gabriele?

  Yes, yes.

• 44:51Speaker 01

  And when they first showed that to me, it was so amazing because I was able to play Space Invaders just by thinking about it and the micro movements in my arms.

• 45:01Mario Gabriele?

  Incredible.

• 45:02Speaker 01

  So, you know, AI is going to, it's going to be the age of the polymath. If you have the ability to think about different systems and how they might work together. Like you're starting to see agents where there's like 20 different types of agents that work together to try to come up with something. You're going to be able to come up with outcomes that were previously, those disciplines didn't work well together. Are going to discover things. A great example of this that I always love to give is Paul Stamets, who's a mycology expert, was walking through a forest one day and he saw some bees on some fungus on a tree. And he thought to himself, well, that's unusual behavior. I'd, I thought, you know, I didn't, I've never seen a bee on some fungus before. I wonder what that's all about.

• 45:45Speaker 01

  And that little rabbit hole led him to creating kind of like an antibiotic of sorts for bees, uh, for groves. So I don't know if you remember, but bee die off was the number one.

• 45:57Mario Gabriele?

  Yes, right.

• 45:58Speaker 01

  Headline for many years, like humanity is doomed, the bees are dying, we're going to have to create little robot bees.

• 46:03Mario Gabriele?

  Yes.

• 46:04Speaker 01

  Some mycologists solved it. That's what we're going to start seeing is somebody that you don't expect. You know, who studied fluid dynamics, suddenly has a physics breakthrough or, you know, things like that are going to be really, really interesting with, uh, because they're going to become AI enabled or AI enhanced.

• 46:24Mario Gabriele?

  That's a really interesting framework that I don't think I've heard someone articulate quite before. To, to, to make sure I'm following, you're, you're basically saying that. Because AI sort of can help you close the knowledge gap on the areas you don't really understand, you can then apply a different lens from your area of expertise and sort of make these sort of different juxtapositions and connections together?

• 46:49Speaker 01

  Yes.

• 46:49Mario Gabriele?

  Yeah, that's really interesting. That's a really good point. I hadn't really put that together.

• 46:53Speaker 01

  The level of creativity that's going to come just out of that will reshape humanity alone.

• 46:57Mario Gabriele?

  I really like that. I mean, it's interesting. That definitely corresponds to my experience with the technology so far, which is that, you know, you can, I mean, I'm sure you're doing this too, but like building a million things with Claude Code and all these sorts of things that are crossing the chasm of things I could have done certain, I couldn't, I could never have done these things before, but still are somehow an extension of like your own perspective and point of view into these new areas?

• 47:21Speaker 01

  Yeah, things about our EAs are making dashboards. Our meetings here at our office have completely changed because people who couldn't code are suddenly able to dream up a way of, you know, sorting data that they never had before because before they had to use an Excel spreadsheet or a Notion or whatever. Now they can actually say, what would it be like to know this information? These are people that never had access to that skill or didn't have the time or the confidence

• 47:48Mario Gabriele?

  Yes.

• 47:49Speaker 01

  that they could understand engineering on that level. And so if you think about engineering being available to everyone, there's creativity in every human being. That's one of the things that's special about humans that makes us so wonderful and beautiful. And AI doesn't sit on its own and just, you can say, come up with 20 ideas, but it's based off of its training data, but it's not going to like, think about a lot of things that only humans are uniquely capable of thinking about. And so I think what's interesting is we need to start thinking about how human work is going to change to where we become professional, we all become professional daydreamers.

• 48:32Speaker 01

  We all become or artisans like I think more some more people are going to start using their hands. I think there's going to be beauty and imperfection, which is goes back to the diamond age and Neil Stephenson's predictions about the future. There was this society called the Victorians, who sourced all of their furniture and all of their clothes and everything from another society that was a group of makers. That was what they loved doing. They wanted to be part of that community. They want to make things by hand. And those things ended up being like books, ended up being the most valuable things in the world. And so it could be the Etsy and companies

• 49:14Speaker 01

  like that just soar because we don't want things that are just 3D printed. We don't want things that look like everything else. Because we are novelty seekers, the novelty might be in the imperfection in the future, not the perfection. But a human being now can sit and think, gosh, I've always wanted this service to exist. And now it can. And eventually you'll be able to vibe products like physical objects. Be able to say like. Like vibe manufacturing is going to be a thing. Million dollar idea you've been sitting on for years, you know, you can now take it on Shark Tank. I think we're going to have so many newly minted millionaires across the world. It might not be venture scalable companies, but they're

• 49:58Speaker 01

  going to be life changing for those families and create wealth that has been unprecedented in those communities. And so I am so excited and optimistic about what all of this unlocks. And at the same time, every tool has a utopia and a dystopia, right? It can be used for horrible, horrific things, and it can be used for incredibly uplifting, amazing things. So I try to stay in the land of utopia and try to stay away from dystopia as much as I can. And so that's where I tend to have all my dreaming is I think about what could unlock human potential.

• 50:39Mario Gabriele?

  Yeah, I really agree with that idea that there will be value in these imperfections. I've been starting to wonder about that with regard to writing, like at what point does having a typo in something make it feel more authentic and more real?

• 50:55Speaker 01

  Yeah, you're gonna want 100% organic human things. I'm seeing a lot of Gen Alpha care deeply about this. You know, they only want to play indie games, even if the quality of the game or the graphics are more rudimentary and less like a AAA game. They would much rather support a human being in that endeavor than to something that was vibe-coded. And they're starting to care about, you know, thoughts being organically human, originating from you. And there could be a spiritual component to that. If you think about going back to what we were talking about, which is if you are a vessel and things are supposed to speak through you, you know, just publishing something

• 51:40Speaker 01

  that just came out of slot from an AI is maybe not the best thing. However, I have used AI to co-create content, and I'm going to say co-create, not create. As the seed and the spark of the idea, it's like molding clay. If you think about words as clay, you can take or leave parts of it. You can say that expression is something I would use, or it's even better than what I would use. And you can sort of like mold it to where it's something that truly expresses what you wanted to say. And so maybe you didn't have the words or the vernacular of sorts to express an idea that's been inside of you, or you've been afraid to do it, and AI takes that out of you.

• 52:23Speaker 01

  In that sense, it's zero to one, right? Like you had no ability to do something, and now you have more confidence to do something. And in that sense, I think AI is very helpful. I think when you just sort of sit back on autopilot and you're like, yeah, that sounds good enough. We all know what those look like. If you go on X or you go anyplace and you read a sub stack that's written by AI, that their creativity is not in it, you can feel it.

• 52:47Mario Gabriele?

  Yeah.

• 52:47Speaker 01

  You know that it's, it's, it's not a hundred percent authentic and not a hundred percent human.

• 52:53Mario Gabriele?

  Yeah, hundred percent agree. Well, you know, I'd love to actually talk a little bit about long journey ventures and in particular, I really love the way that you define what you're looking for, which is magical weirdos. I, I really obsess about trying to think about the traits that make for great founders and that's a nice configuration, I think. But I also wonder, what does a magical weirdo look like to you? I imagine there, there are lots of different archetypes, lots of different sort of clusters of traits, but perhaps a few that seem to pop up more than others.

• 53:26Speaker 01

  Yeah, I mean, just like human beings and thumbprints, you know, they're, they come in a wide variety feathers. I don't know how else to describe it, but

• 53:38Mario Gabriele?

  Yeah.

• 53:39Speaker 01

  really what it comes down to is there's a unique experience that's happened in their life, whether it be trauma or some hurdle they had to overcome or something that they've noticed that's deeply wrong about the world that they want to correct. Insight that they have that no one believes and they've got to bring it to reality. They've got to bring it into our world and they are driven by this, maniacally so. And then their way of being,

• 54:09Speaker 01

  how they navigate is usually very interesting and bizarre too. So I'm going to take a company called BusRight, for example, that we invested in, which does bus logistics for schools. Now that sounds like a boring problem, right? It's like, hmm, but if you met Keith Corso, the founder, he is the most delightful, inquisitive, curious person you could ever meet, who is uniquely the moat of that business. Because it takes someone who wakes up in the morning, which he does, and immediately says, you know what, we need to solve today, buses! You know, and he gets all of his team fired up about it.

• 54:50Speaker 01

  And, you know, he convinces people, kind of like a Pied Piper, to, to get people to follow him into this seemingly boring space.

• 54:59Speaker 01

  Practically weird by itself, right?

• 55:02Mario Gabriele?

  Yes.

• 55:02Speaker 01

  And so that's what we call magical founders running boring businesses. And we invest in a lot of those, but we also like magical founders doing magical things, which is the frontier. And that you have to be a little careful because you have to make sure they're paired with someone who's operational, who has, we call it the biz tis and riz. So if you've got someone who's really high tis, you gotta-

• 55:27Mario Gabriele?

  What's tis?

• 55:28Speaker 01

  Autistic. I view autistic as a skill. I have you as a superpower.

• 55:34Mario Gabriele?

  Yeah, absolutely.

• 55:36Speaker 01

  I'm on the spectrum. You know, there's certain things I don't understand and get and certain social cues that escape me, but it's, it's, my deficits are also my superpowers.

• 55:45Mario Gabriele?

  Yes.

• 55:46Speaker 01

  So when you see somebody who doesn't make eye contact and looks down, you know, sometimes in the past, that didn't pattern match what, you know, a good founder was supposed to be like. And instead you could ask yourself, how do they lead? And you might discover that they're really amazing writers and they lead through Slack.

• 56:04Speaker 01

  A great example of this is Brendan Icke from Brave. A lot of people are like, wow, he doesn't make eye contact or he doesn't, you know, he, he's very quiet or he sits in the background, you know, how can he lead a team? And I'm like, well, he leads open source projects and he, developers really regard him highly and look up to him. And he's kind of a legend. And so I have no issues with his leadership style, which, you know, gave me an unfair advantage because I could just dismiss that part. Some people will say no, because it doesn't just, you know, somebody doesn't go straight down the fairway. You know, they're not like, you know, this person looks like they have an MBA and, you know, they did these things or they know these people or they have this pedigree.

• 56:49Speaker 01

  If you look at Crusoe, the founder had this crazy idea and he did not come from the oil fields.

• 56:57Mario Gabriele?

  Yes.

• 56:57Speaker 01

  You know, but he had this crazy idea of like, we're going to have a power shortage and we're going to have a compute problem for crypto and then later AI, right? This insight that he had led him to build one of the most amazing data center companies that is enabling a lot of what we're even talking about right now. Again, I, I love human beings. And so when I sit with someone and- I collect people, I always like to say I collect personalities and people like Pokemon. And you know, when you found a legendary Pokemon, you know, when you found something so special and unique and rare. A mind like no other. And then it's just like, okay, well, do they have, are they paired with the biz?

• 57:41Speaker 01

  Or are, do they have business capabilities? Because you can have an academic who's brilliant, who has a groundbreaking, you know, idea or technology. But if they can't bring it to market, if they can't hire people, if they can't people, and that's not going to go anywhere, which um, unfortunately, a lot of things die there.

• 58:01Mario Gabriele?

  And so it was biz, tism was the third one?

• 58:03Speaker 01

  Riz, charisma.

• 58:04Mario Gabriele?

  Riz, interesting. The charisma matters, huh?

• 58:09Speaker 01

  It really matters, you know, I think charisma is your ability to sell, your ability to create a culture, your ability to be that pied piper that gets people behind you. And if you're not that person, someone in your company needs to be. So we think that the perfect trifecta and my partner, Ariel Zuckerberg came up with this framework.

• 58:30Mario Gabriele?

  It's a good one.

• 58:31Speaker 01

  It's really great. So we always, every time we evaluate a company, we're like, what's the biz tis riz dynamic going on here?

• 58:39Mario Gabriele?

  How often do you see that in one person? Almost never, a lot of the time?

• 58:44Speaker 01

  Sometimes you get it. And it's a, it's kind of a miracle. It's like a genie in a bottle. You're like, wow, that person has all three. Um, a great example would be Josh Browder. He has so much charisma. He, he led a game of mafia uh, with us one time and you got to really see his personality just really come out, you know, because someone who's on the tis spectrum, who has charisma, usually will talk about their special interests and go very, very deep. And then if you have the business skills on top of that, then it's probably like, you know, back the truck up. Give them resources and get out of their way.

• 59:20Mario Gabriele?

  You know, in, in researching you and your, your story, uh, you seem to live a, a very unusual life in other ways, like you live in a retirement community.

• 59:30Speaker 01

  Part.

• 59:31Mario Gabriele?

  Part time, okay. Why was that a, a choice you made? And I wonder how it sort of forms your perspective?

• 59:37Speaker 01

  I went to this retirement community that a friend brought me to, to play golf. And I was not into golf, actually. And but I looked around at the infrastructure. And I was like, wow, there's this community center and there's this big swath of land and there's all these people living around it. What if you could sort of slowly? Keep in mind that everybody that's living in these places, this is their dream right now. This is what they looked forward to in their thirties or forties and they're living their dreams. So you don't want to come in and destroy the dream. But what you want to do is start thinking about what your dream is.

• 1:00:20Speaker 01

  And when I'm eighty years old, I have a very specific dream. Which is I want to live in a community that has amazing things going on every night of the week, but driven by the community. My house, we're building, um, we're almost done with it, an outdoor movie theater that's a drive in that um golf carts can pull into.

• 1:00:40Mario Gabriele?

  Oh, awesome.

• 1:00:41Speaker 01

  Little speakers or you bring your own speaker and you tune in to the movie, just like the old days, but you're in your little golf cart.

• 1:00:48Mario Gabriele?

  Oh, that's awesome.

• 1:00:49Speaker 01

  So I'm going to be responsible for a movie a week, maybe, right? And then there's a guy down the street who built a tiki lounge in a tree that's only open on Thursdays. And there's also, um, you know, we have a wood fired pizza oven. And you know, now you can just vibe code an app and create a local pizza delivery for your neighbors. You can create an underground jazz club. And you know, retired musicians or musicians passing through can perform on Fridays. You know, you could, there's so, there's also, it's one of the only golf courses, there's only seven, I think, golf courses in America that have an airstrip.

• 1:01:28Speaker 01

  So this one has an airstrip and so like, if you're into piloting and you're into airplanes, you could get into aviation. And there's a workshop there, a wood shop. And so you can build things. And so that's what I dream about my future. And so what I've been doing is recruiting my friends to live there and buy houses.

• 1:01:47Mario Gabriele?

  I love that.

• 1:01:48Speaker 01

  With the idea that we're all going to kind of spend either full time or part time there. And that's the dream, you know, and then the golf club is there if you like to golf, but who knows if it stays a golf club, you know, fifty, you gotta have a fifty hundred year view, right? And fifty to a hundred years, maybe it's an esports arena. I don't know. Golf might not exist then, I don't know.

• 1:02:10Mario Gabriele?

  Yeah.

• 1:02:11Speaker 01

  But but regardless, it's a huge piece of land that could be utilized for a lot of different things. And right now it's golf. And so that's why I started doing it. And the other thing is, I love being around older people. There's so much wisdom that you can learn from an eighty or ninety year old, especially at the end of their life or their last days. And so I've sat by the bedside of people there who are dying, who have told me things like, they know that someone's coming over and there's no way that they could know that that person's coming over. Or they see their family around the bed. You can't see them, but they're there for them.

• 1:02:50Mario Gabriele?

  Wow.

• 1:02:51Speaker 01

  And they're talking to them. And then the wisdom they give you in those last moments is priceless. And they live these happy lives. Like, there's this woman who lived to be ninety three. And she died at home with a window looking at the golf course. And everybody came by and waved at her and, you know, punted in front of her window. And she died very happy.

• 1:03:14Mario Gabriele?

  Yeah.

• 1:03:14Speaker 01

  And I thought to myself, that's what I want for me and my friends and loved ones. And I want everybody to start thinking about this because the alternative is you end up in one of those homes alone with strangers.

• 1:03:28Mario Gabriele?

  Yeah.

• 1:03:29Speaker 01

  And that's sad.

• 1:03:30Mario Gabriele?

  Yeah.

• 1:03:30Speaker 01

  You have to be that way. Like, we could come together as a community and support one another. And there's a much more beautiful alternative.

• 1:03:39Mario Gabriele?

  Yes.

• 1:03:40Speaker 01

  It involves volunteering. You know, you have to volunteer, you have to participate. Think of it as a Burning Man that doesn't go away.

• 1:03:48Speaker 01

  You know, it's a way of living.

• 1:03:49Mario Gabriele?

  Yeah. Another eclectic thing that I came across was you seem to be one of the more adventurous readers I have come across. Like, I don't think, I mean, Vonnegut, great love, you know, everyone should read him, but I don't know if I know many people who have read Aleister Crowley. What are your reading habits? How do you decide where your curiosity takes you? What do you take from people like, like a Crowley?

• 1:04:13Speaker 01

  So my favorite thing to do in the world, and I recommend that everybody go to their local bookstore, used bookstore ideally, and walk around the store with your hands on the books, and one of them's going to jump out at you. Either the color of the spine, the picture on the book, or just something about it is going to be like, buy me, read me, or it'll be something you've always wanted to read and haven't taken the time to read. And my favorite bookstore, it's called B Street Books in Burlingame, has a bookshelf of books that can't be categorized or put away, so they don't know where they go. So I go there

• 1:04:57Speaker 01

  and I'll buy like four or five books off those shelves. And some of my favorite books and the things, rabbit holes I've gone down, have been because of those books. Things I would have never picked. So that's again, breaking mechanical behavior. Like, don't, don't just read what everybody else is reading. Read something that calls to you, that speaks to you. I've read a book about automat's. I've read, you know, it, and it gets you thinking about like, I don't know if you know this, but in the twenties, New York had all these automat's everywhere. And so you could go in-

• 1:05:28Mario Gabriele?

  What is an automat, sorry?

• 1:05:29Speaker 01

  It's basically a place where you would go and get food, and there were home-cooked meals inside these little windows, and you would go put a quarter in, or get a ticket, and then you would take food out of the window.

• 1:05:40Mario Gabriele?

  Oh, interesting.

• 1:05:40Speaker 01

  People were able to, because they could make these things in such large batches, they could drive the prices down, and you could have mashed potatoes, meatloaf, you know, green beans. And if you read about the quality of food, it was incredibly high and incredibly nutritious, and not deep fried, and not like what fast food is today. And so, you know, David Friedberg created an automat that was ahead of its time, which was based on quinoa. And it was downtown in San Francisco before the pandemic and the food was incredible. It was magical, but it was ahead of its time. And so I think automat's are going to come back. Japan is obviously the leader in this space. They have machines and they have,

• 1:06:22Mario Gabriele?

  Yes.

• 1:06:22Speaker 01

  you know, tickets where you can go get ramen and get them out of things. And so I think that eventually in order to drive costs down and have nutritious food, you know, you either have to have robots or you have to have something like this. And so I, this is how I think about the world is like, I just go and grab a random book. The other thing is I'll open it to a random page and you'll be surprised that sometimes that random page is exactly what you need to be reading. It'll speak to you in a way that's unique to you. I mean, honestly, I roll the dice when it comes to books a lot of the time. Sometimes I find them in the little free libraries. Uh, sometimes people will just hand me a book or I'll find it on the ground.

• 1:07:05Speaker 01

  And the Aleister Crowley stuff came because um, I found this like printed paper from the early 1900s and I found this little story by Frank Harris in there called The Magic Glasses, which changed my life. And it wasn't even by Aleister Crowley, it was by this guy Frank Harris. That led me down a Frank Harris rabbit hole. And I discovered that he wrote a book that was banned called My Life and Loves, which is basically all of his sex campaigns with every woman he'd ever been with in one book.

• 1:07:38Mario Gabriele?

  Oh, wow.

• 1:07:39Speaker 01

  You can imagine that was pretty controversial back then.

• 1:07:41Mario Gabriele?

  Yes, yes.

• 1:07:42Speaker 01

  And uh, and I went and read it. And then I discovered that he was a cowboy outlaw. And that he left England when he was 14 and came to America. And it was just this really interesting human that I never heard of that hung out with all the greatest writers of the time. And then I just looked at, I was like, well, this Crowley character is odd. You know, so I went down that rabbit hole and I'm like, what a weird guy. Very controversial with very controversial ideas. But it led me into, there was a whole movement around that time of people who were experimenting with reality. And that resonated with me more than anything, which was, you know, these mystics. I also led me to Sufi thinking, Kobolos. All of them are kind of birds of a feather.

• 1:08:26Speaker 01

  And then Gergiev, which is one of my favorite mystic philosophers. I highly recommend reading Gergiev and Now Spinski. And so these things kind of build on each other, right? Like you, you read something and it inspires you to read another thing and inspires you to read another thing. And that's kind of how, how it all works for me.

• 1:08:45Mario Gabriele?

  I love that. Well, maybe that's, uh, on, as we're on the topic, I always like to end these conversations with a bit of a thought experiment, half thought experiment, half book recommendation. If you had the chance to give a book to everyone on earth to, to read and understand, what would you want to give to people or recommend to people?

• 1:09:03Speaker 01

  Okay, there's the, the answer I want to give. And then there's an answer that's probably the right answer.

• 1:09:10Mario Gabriele?

  Oh, we'll take both. I, you know, the, the, both are great.

• 1:09:14Speaker 01

  Mandatory reading for everyone should be books on economics. I think there's, there's just a deep understanding about how the world works. And a distrust of capitalism that without a fundamental understanding of what it is. And so that would probably be number one, and I, I can't rattle off, you know, maybe Milton Friedman or something like that, but the book I would want everyone to read is The Razor's Edge by Somerset Maugham.

• 1:09:41Mario Gabriele?

  Wow. Why that book? That's such a, that's a great choice.

• 1:09:44Speaker 01

  It's such a beautiful book. Somerset Maugham is just, in study his life and study like where he lived and why he wrote what he wrote, when he wrote it, and the, the period and set and setting of, you know, the war and, and everything. I think it's such a beautiful display of human nature. You know, of the archetypes that exist in this world around suffering. And how to escape it. And it actually was the story that led to my spiritual awakening. There is a character in there who faced with profound sadness.

• 1:10:24Speaker 01

  Could wallow in that sadness, but he chooses not to. Instead, he chooses a stoic exit and decides that it just doesn't matter because he has to go live in the now. And living in the now can sometimes be lonely. It can be, like they say, the razor's edge is often walked alone and it can even cut the walker. And so there's a lot of people that will not go on that journey with you. And this story is about that. It's about the awakening of a person who went to war, saw some brutally horrible things, decided to leave the script of the life that he was supposed to lead and find his own true identity and finds it in the end.

• 1:11:09Speaker 01

  For me, it's my story as well. And so I deeply resonate with it. I recommend reading the book first. Then there's a movie that was filmed, I think in the 40s, 30s or 40s. And then there's a movie that Bill Murray made with his brother.

• 1:11:26Speaker 01

  And so what's interesting about that movie is in order to film Ghostbusters 2, this is what the lore is, said, I'll only do it if you allow me to produce this movie and you pay for it. It came out and was not, didn't receive no critical, like no acclaim. It was kind of like a blip.

• 1:11:46Mario Gabriele?

  Wow.

• 1:11:46Speaker 01

  Um, and all of his movies, if you were to ask people what their favorite movie is of his, that is never hardly ever mentioned. But I would argue is one of the most profound roles that he's ever been in and stories he's ever told. It's the one that impacted me the most. And so, um, but start with the book so that you understand the archetypes. Because his movie is different than the book. And you can understand what Somerset Maugham was trying to do, um, to convey to you.

• 1:12:18Mario Gabriele?

  Cyan, this was, uh, as. Freewheeling and deep and interesting as I had hoped it would be. Thank you so much. This was really a pleasure.

• 1:12:27Speaker 01

  Thank you. I'm a huge fan of your, your work and your writing and of Hummingbird.

• 1:12:33Mario Gabriele?

  Oh.

• 1:12:33Speaker 01

  Yeah, I'm really excited where you've landed because they're remarkable people and truly, truly independent thinkers.

• 1:12:42Mario Gabriele?

  Yes.

• 1:12:42Speaker 01

  And so it's a great place to land. So congratulations.

• 1:12:46Mario Gabriele?

  Thank you so much. That's it. Thank you for listening to this episode of the Generalist Podcast. Please subscribe on Apple Podcasts, Spotify, or your preferred podcast app. Ratings and reviews help others discover these discussions. So if you enjoyed the conversation, I'd be grateful if you could take a moment to leave one. For all past episodes and more, visit us at thegeneralist.substack.com. See you next time as we continue to explore the future.