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

Speaker A: 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, Pokémon Go. Speaker B: 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, Pokémon Go, that happened because I noticed my friends playing this game called Ingress 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. 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. 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. Speaker C: Cyan Bannister has written that she is never playing the game that 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 Andrew Hill, 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, and why brain-computer interfaces are primed to break out over just the next 2 years, in her view. Speaker C: Cyan Bannister has written that she is never playing the game that 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 Andrew Hill, 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, and why brain-computer interfaces are primed to break out over just the next 2 years, in her view. Speaker A: We also cover why she's building a drive-in movie theater for golf carts and the Somerset Maugham novel she thinks everyone on Earth should read. Speaker C: I'm Mario, and this is The Generalist. This episode is brought to you

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They take care of things like expenses, all according to your rules, so you can move faster while staying in full control. 1 in 3 startups in the US already runs on Brex. You can too. At com/mario. Speaker A: Well, Cyan, I've been looking forward to this for an extremely long time. Uh, I remember you being sort of one of the first people who I thought seemed extraordinarily interesting when I first got interested in, 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, uh, yeah, when I, when I think about people who seem to occupy different pockets of the future, you are, you are certainly one of them. So thank you so much for, for being with us. Speaker B: Yeah, thank you for having me. The honor's mine. Thank you. Speaker A: 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, uh, 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, uh, I think a curb reading Vonnegut books and waiting for an older crush to notice you. And you have this line, which is that you're never playing the game you seem to be playing. Speaker B: Yes.

Speaker A: 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. Speaker B: 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. We say that that's just how it is. But what happens if you start rolling the dice? What happens if you start, you 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.

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, yes, then, you know, that, that kind of defies the purpose. Speaker B: Yes. Speaker A: 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. Speaker B: 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. We say that that's just how it is.

But what happens if you start rolling the dice? What happens if you start, you 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. 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, yes, then, you know, that, that kind of defies the purpose.

Speaker A: Yeah, you, you tilt the experiment if you, if you share too much. Speaker B: And in that particular experiment, I got the guy, right? Speaker A: Yeah, it worked out. And you read a lot of Vonnegut, which, uh, you know, win-win. Speaker B: Exactly, exactly. So I sat there and read a lot of Vonnegut, and, um, it helped that I kind of had an inkling that he liked Vonnegut but you know, uh, eventually he did notice me and, and then it all worked out. Speaker A: You know, I think that idea of almost remaining, you could call it playful or childlike or open-minded, you know, uh, 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? Speaker B: 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, yeah. 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 experiment, right? And so I look at the world that way. 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. Like, go outside and be like, wow, I may not feel air again. Like, air'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 gotta 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. Speaker A: Yeah. Speaker B: 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 mindful. More full of wonder every day. Speaker A: Hmm. How did that sort of spiritual philosophical posture come to you? Was that something you were, I don't know, 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 after a stroke. Like, was it, you know, more tied to that? Where does that come from? Speaker B: 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. Um, 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— 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. And 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, there's a couple of us, but 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? And that thought experiment lasted several years, and I asked myself, have I been really, really honest about spirituality, or if 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, 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. Speaker A: You became more of a magnet for weird things after being sort of, as you say, tricking yourself into becoming a believer? Speaker B: Yeah, my life was already bizarre and weird and magical, but 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? Speaker A: The crazy one? Speaker B: Please, yeah. I was listening to something called The Telepathy Tapes, and if you haven't listened to it, I highly recommend it. Speaker A: For folks that don't know what that is, would you mind giving a précis? Speaker B: Oh, absolutely, yeah. The podcast is about parents who are, who have children, both adults and underage who have autism and are non-verbal. 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 seek and look for things. And then they realized, no, it's not that. 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. Um, in one particular case, there's, um, a gentleman who could recite novels, uh, but had never read. Speaker A: Wow. Speaker B: 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 sat or met God, sat with God or met God. Speaker A: Oh wow. Speaker B: So they all claim that there's a metaphysical school that they all go to, so a 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. 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. There's a 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 wanna think about this as a scientist, obviously social contagion is a thing. Speaker A: Yes. Speaker B: 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."

To Spotify? Like, I don't know what I'm doing. I'm gonna 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 3 months prior that was completely non sequitur. So it was not like the last message we had.

It was something from 3 months ago. I fell on the ground and started crying because one, I missed this person dearly and I wanted them back in my life. Also, it may have worked. So, and I say may have because I'm not a scientist, but I am a scientist. Speaker A: Yes, a scientist. Speaker B: Yeah, 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, 1 o'clock my time in New York. And I was like, oh, why? Because 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? 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. Speaker B: Yeah, 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, 1 o'clock my time in New York. And I was like, oh, why? Because 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? 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.

Speaker A: I see. That's the, that's an interesting theory, right? Speaker B: So I'm starting 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 gonna 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 skills, are able to continuously do this. Now here's where it's really gonna blow your mind. So I'm down at a farm in Temecula in a grapefruit grove, and, um, 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, uh, I highly recommend all everyone also watch the movie Spellers. Halfway through the movie, my friend Chris pauses the movie and he says, Sayan, 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 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. Speaker A: Oh, cute. Speaker B: Or they'll show it a picture of a yellow car and it goes, yellow car. You know, so whatever she sees, the bird spits out. Speaker A: Yeah. Speaker B: So just as I'm telling this story, all of a sudden we hear, help me, help me. And I looked 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, sayonara, sayonara, 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.

Speaker A: Wow. Speaker B: Saying, help me. Speaker A: Oh my gosh. Speaker B: I, I can send you video of this. It's insane. And I was like, what are the chances? What are the odds? Wow. This is the kind of stuff I'm talking about. Speaker A: Gosh. Speaker B: Now, it took us 3 days to find the owner of that bird. You know, we named it Telly for telepathy because we thought it's a telepathic bird. Speaker A: Yeah. Speaker B: And we found its owner, which was 2 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?

'Cause we call it Telly, and they said it's named Mumbles. And I said, why is its name Mumbles? And they said, because it doesn't say as many words as a cockatoo should. 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. Speaker A: Yes. Speaker B: May just be natural. Speaker A: Mm-hmm.

Speaker B: 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 could be because we're so distracted. It could be because of our ego. So the ego plays a huge part of it. You gotta 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, 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. Speaker A: What does non-local consciousness mean? Speaker B: 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 gonna 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. You're basically an antenna that waits to get information. And so if you talk to a lot of artists, like, look, 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, in 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. Speaker A: Yes. Speaker B: 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 BCIs, 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 2 weeks old, like you thought about 2 weeks ago. Speaker A: That is still visible in a BCI. Speaker B: 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? Yeah, I think in the next 2 to 3 years we're gonna figure it out. And when we do, you've gotta 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. Speaker A: You know, I think the sign of a good conversation that there's, uh, 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, uh, along with you.

You should be skeptical. Speaker A: You know, I think the sign of a good conversation that there's, uh, 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, uh, along with you. You should be skeptical. Speaker B: 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. I, 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. Yeah. Speaker A: Run your experiments. Speaker B: Run your own experiments. Speaker A: 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 3 or 4 levels deeper that one can go to think about it.

Um, and so I'm excited to do that piece. And then you're, I think the, have you ever read the book Impro? Speaker B: No. Speaker A: It strikes me that you might really like, um, the discussion of creativity in that. It's from one of the guys who basically created the, the philosophy of improvisational comedy and theater. Um, 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. Speaker B: 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, Yeah. 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 veneer, or if it's really who they are.

Yes. And so I think art used to be very different, you know, even in 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.

Speaker A: You know, you're, you've been one of the best investors, I would say, of, of the past 15, 20 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. Like there's some version of a VC that people think, ah, you know, uh, we want someone who did 2 years at McKinsey, 2 years at Google, and then maybe a startup stint. And that really doesn't capture the level of imagination that's required. Speaker B: 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? Speaker A: Yeah. Speaker B: And he said, well, one is I'm a historian, so you have to understand the past. Speaker A: Huh. Speaker B: And two, you have to understand how the money's made. You can look to the future and you can come up with a utopian paradise, but if there's no way to make money in that utopia, it just won't happen.

'Cause markets will drive things forward, right? And so that's how he figured out the Diamond Age and how he figured out Snow Crash is 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'll make— Speaker A: 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 it?

Speaker B: Yeah, which, uh, basically, um, invented crowdfunding 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 in under an hour. But it was based in a warehouse and this was, um, around year 2000, 2001. Oh wow. And they went belly up because they couldn't figure out how to make the margins work.

Speaker B: Yeah, which, uh, basically, um, invented crowdfunding 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 in under an hour. But it was based in a warehouse and this was, um, around year 2000, 2001. Oh wow. And they went belly up because they couldn't figure out how to make the margins work.

Speaker C: Yeah. Speaker B: But 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 gonna need to be in place for this to exist? And when do you think they're gonna 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. Speaker C: Yeah. Speaker B: They came, 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, uh, 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. Speaker C: Yeah. Speaker B: They came, 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, uh, 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. Speaker A: What was interesting about him? Speaker B: 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, someone to watch, right?

Speaker A: Yeah. Speaker B: So I just put a pin in it. And then a few months later, I saw him pitching at Open Angel Forum, UberCab. Now, keep in mind also, I had an Uber driver. My personal driver was driver number one for Uber. Another weird— Speaker A: Oh, wow. Speaker B: Yeah. Speaker A: Gosh. Speaker B: 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. Speaker A: Oh, wow. Speaker B: Yeah.

Speaker A: Gosh. Speaker B: 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. Speaker A: It was just like— not subtle. Speaker B: 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 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. And so I order my coffee and I get on the Wi-Fi and I notice that on the Wi-Fi 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 Raboi and I'm like, oh, okay.

He has a Pixel phone maybe. Speaker A: Hmm. Speaker B: 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 at the time. And I did not go to the demo day, so I didn't know, or it was coming up.

I don't know if he had pitched or, or what. And I remember a conversation. This is where observation comes into play here, right? A conversation at Founders 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, uh, 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 wanna meet.

And I was like, well, he's just right across from me. And he's like, well, walk over there, say hi. Speaker A: Hmm. Speaker B: 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 at the time.

And I did not go to the demo day, so I didn't know, or it was coming up. I don't know if he had pitched or, or what. And I remember a conversation. This is where observation comes into play here, right? A conversation at Founders 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, uh, 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 wanna meet. And I was like, well, he's just right across from me. And he's like, well, walk over there, say hi. Speaker A: Perfect. Speaker B: 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 Founders 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 wanna know? And I told him and he blushed and we were gonna 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, um, co-leading the Series A down the road. But that company, what is, what, valued at $7 billion, $8 billion or something at this point and solves a huge percentage of the country's petty crime, like bicycles and lawn mowers, and it also solves Amber Alerts and things like that.

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Whether you're verifying age, onboarding businesses, or automating KYC. It's fully configurable so you can launch in days, not quarters. Wanna see for yourself? Generalist listeners get a free year of the starter plan. Head to com/generalist and check it out. Speaker B: And so I think, you know, you have to be open to an opportunity presenting itself in the most unusual of places. You know, Pokémon Go, that happened because I noticed my friends playing this game called Ingress 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? Like, what? Speaker A: For this geo game? Speaker B: Yeah, it looks like geocaching. Yes. 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 Pokémon was gonna be involved, I was like, I went around to everyone saying, you don't understand, everyone's gonna be catching invisible Pokémon.

And they're like, you're insane. No one's going to be looking at their phone. Nobody. Speaker A: Yes. Speaker B: If you remember, everybody's doing this. Speaker A: Yeah. Yeah, totally. Speaker B: And I would argue it was the closest we ever came to world peace. Speaker A: 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, 8 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 really beautiful way of people finding these new connections.

Why do you think that didn't stick as a form factor? Speaker B: Human nature. Speaker A: Hmm. Speaker B: So Pokémon Go is still quite large. They make billions of dollars. It's still played worldwide. It was acquired recently, and the company that acquired it also made Monopoly Go, which is not geolocation, but it's, 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? Because Harry Potter should be, that should be, you know, yeah, even bigger, right? 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, 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. But that's probably why I posit, I don't know for sure that, you know, that didn't work out.

But Pikmin 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 how our bodies are wired and trained. But there's some people who still use Pokémon to get out and walk, to get out and meet friends.

They still go to the festivals, they go to the meetups, they go out on special Pokémon Days and catch special Pokémon. 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. Speaker A: 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 that, that, that more people haven't sort of taken the Pokémon Go hard problem.

Speaker B: 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. Speaker A: Yeah. Speaker B: And the police were like, no, no, you need to geofence this spot. Speaker A: And on baseball fields and all these sorts of, you know, on professional stadiums. Speaker B: Exactly. So running into stores that they are, even people's yards, you know?

Speaker A: Yes, yeah. Speaker B: Figuring out that piece was probably one of the hardest parts, and nobody owns a better map of that than Niantic. So my insight to 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. Speaker A: Well, speaking of a, 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 2 to 3 years. What, what do you expect to help us get there? Like, or have you just seen— Speaker A: Well, speaking of a, 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 2 to 3 years.

What, what do you expect to help us get there? Like, or have you just seen— Speaker B: 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, uh, 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. Um, every week I read about some new, like I just read about a hat that allows you to type. Speaker A: I just saw the same thing. I bet the, the beanie, right? Speaker B: No, the beanie. Yes. So you'll be able to type without using a keyboard. And, um, I remember I invested in CTRL Labs, which ended up becoming part of the, the Meta Ray-Bans, the, the gesture control. Speaker A: Yes. Yes. Speaker B: 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.

Speaker A: Incredible. Speaker B: So, you know, AI is going to, it's gonna 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 gonna be able to come up with outcomes that were previously, those disciplines didn't work well together, are gonna 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, I thought, you know, I didn't, I've never seen a bee on some fungus before. I wonder what that's all about. 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. Speaker B: 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. Speaker A: Incredible. Speaker B: So, you know, AI is going to, it's gonna 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 gonna be able to come up with outcomes that were previously, those disciplines didn't work well together, are gonna 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, I thought, you know, I didn't, I've never seen a bee on some fungus before. I wonder what that's all about. 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. Speaker A: Yes. Right. Speaker B: Headline for many years. Like humanity's doomed. The bees are dying. We're going to have to create little robot bees. Speaker A: Yes. Speaker B: Some mycologist 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 gonna become AI enabled or AI enhanced. Speaker A: 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.

Speaker B: Yes. Speaker A: Yeah. That's really interesting. That's a really good point. I hadn't really put that together. Speaker B: The level of creativity that's gonna come just out of that will reshape humanity alone. Speaker A: I really like that. I'm, I mean, I, it's interesting. That definitely, uh, 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.

Speaker B: Yeah. Think 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 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 gonna 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. 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 goes back to the Diamond Age and Neal Stephenson's predictions about the future. There was this, uh, 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 wanted 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 that Etsy and companies 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's gonna 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 gonna have so many newly minted millionaires across the world. These 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. 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. Speaker A: Yeah, I really agree with that idea that there'll 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?

Speaker B: 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 wanna 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, 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 that just came out as slop from an AI is maybe not the best thing.

However, I have used AI to co-create content, and I'm gonna say co-create, not create, is 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, 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.

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 Substack that's written by AI, that their creativity's not in it, you can feel it. Speaker A: Yeah. Speaker B: I think you know that it's, it's, it's not 100% authentic and not 100% human.

Speaker A: Yeah, 100% agree. Well, you know, I'd love to actually talk a little bit about Long Journey Ventures, and, um, 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, uh, 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.

Speaker B: Yeah, I mean, just like human beings and thumbprints, you know, they come in a wide variety of feathers. I don't know how else to describe it, but 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 gotta bring it to reality. They've gotta bring it into our world, and they are driven by this maniacally so.

And then their way of being, um, how they navigate is usually very interesting and bizarre too. So I'm gonna take a company called Busrite, 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 and, you know, he, he convinces people kind of like a Pied Piper to, to get people to follow him into this seemingly boring space. Magically weird by itself, right? Speaker A: Yes. Speaker B: 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, tiz, and riz.

Uh, so if you've got someone who's really high tiz, you got autistic. I view it as a superpower. Speaker A: Yeah, absolutely. Speaker B: I'm on the spectrum, you know, there's certain things I don't understand and get in certain social cues that escape me, but in, it's, it's my deficits are also my superpowers. Yes. Speaker A: Yes. Speaker B: 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. A great example of this is Brendan Eich 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. If you look at Crusoe, the founder had this crazy idea and he did not come from the oil fields.

Speaker A: Yes. Speaker B: You know, but he had this crazy idea of like, we're gonna have a power shortage and we're gonna 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, I always like to say I collect personalities and people like Pokémon.

And you know when you found a legendary Pokémon, 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 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, then that's not gonna go anywhere, which, unfortunately a lot of things die there.

Speaker A: And so it was biz, tiz, and what was the third one? Speaker B: Riz. Charisma. Speaker A: Riz. Okay. Interesting. The, the charisma matters, huh? Speaker B: 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, um, Ariel Zuckerberg came up with this framework. Speaker A: It's a good one.

Speaker B: It's really great. She's, so we always, every time we evaluate a company, we're like, what's the biz-tiz-riz dynamic going on here? Speaker A: How often do you see that in one person? Speaker C: Almost never. Speaker A: A lot of the time. Speaker B: Sometimes you get it and it's, uh, 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 they have the business skills on top of that, then it's probably like You know, back the truck up, give them resources and get outta their way. Speaker A: 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. Part-time. Uh, part-time. Okay. Why was that a, a choice you made? And I wonder how it sort of forms your perspective. Speaker B: I went to this retirement community, uh, 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 30s or 40s, and they're living their dream. 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.

And when I'm 80 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. Oh, awesome. And then you have 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. Speaker A: Oh, that's awesome.

Speaker B: And so I'm gonna 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 7, I think, golf courses in America that have an airstrip. 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. Speaker A: I love that. Speaker B: With the idea that we're all gonna kind of spend either full-time or part-time there.

And, uh, 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, 50, you gotta have a 50, 100 year view, right? And 50 to 100 years, maybe it's an esports arena. I don't know. Golf might not exist then. I don't know. Yeah. 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 80 or 90-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. Speaker A: Wow. Speaker B: 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 93 and, um, she died at home with a window looking at the golf course and everybody came by and waved at her and, you know, putted in front of her window and she died very happy. Yeah. 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. Speaker A: Yeah.

Speaker B: And that's sad. Yeah. 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. Yes. But 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. You know, it's a way of living. Speaker A: Yeah. Another eclectic thing that I came across was you seem to be one of the more adventurous readers I, 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, uh, 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. Speaker B: So my favorite thing to do in the world, and I recommend that everybody go to their local bookstore, uh, 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 and I'll buy like 4 or 5 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've 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 automats. I've read, you know, it, and it gets you thinking about like, I don't know if you know this, but in the '20s, New York had all these automats everywhere. And so you would go in— Speaker B: So my favorite thing to do in the world, and I recommend that everybody go to their local bookstore, uh, 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 and I'll buy like 4 or 5 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've 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 automats. I've read, you know, it, and it gets you thinking about like, I don't know if you know this, but in the '20s, New York had all these automats everywhere. And so you would go in— Speaker A: what is an automats? Sorry. Speaker B: 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. Speaker A: Oh, interesting.

Speaker B: So 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, uh, 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 automats are gonna come back. Japan is, uh, obviously the leader in this space. They have vending machines and they have, yes, 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. 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. Oh, wow. You can imagine that was pretty controversial back then. Speaker B: 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.

Speaker A: Oh, interesting. Speaker B: So 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, uh, 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 automats are gonna come back. Japan is, uh, obviously the leader in this space. They have vending machines and they have, yes, 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. 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. Oh, wow. You can imagine that was pretty controversial back then. Speaker A: Yes. Yes. Speaker B: 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.

It also led me to Sufi thinking, uh, Kabbalists. Uh, all of them are kind of birds of a feather. And then Gurdjieff, which is one of my favorite mystic philosophers. I highly recommend reading Gurdjieff and Ouspensky. And so these things kind of build on each other, right? Like you, you read something and it inspires you to read another thing, inspires you to read another thing. And That's kind of how, how it all works for me. Speaker A: I love that. Well, maybe that's, uh, on, as we're on the topic, uh, I always like to end these conversations with a bit of a, 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? Speaker B: Okay. There's the, the answer I want to give. And then there's an answer that's probably the right answer. Speaker A: Oh, we'll take both. I've, you know, both are great. Speaker B: Okay. There's the, the answer I want to give. And then there's an answer that's probably the right answer. Speaker A: Oh, we'll take both. I've, you know, both are great.

Speaker B: Mandatory reading for everyone should be books on economics. Um, I think there's, there's just a deep understanding about how the world works and, um, 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. Speaker A: Wow. Why that book? That's such a, that's a great choice. Speaker B: It's such a beautiful book.

Somerset Maugham is just, and study his life and study like where he lived and why he wrote what he wrote when he wrote it and the period and set and setting of, you know, the war 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's a character in there who, faced with profound sadness, 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.

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. 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. Speaker A: Wow. Speaker B: Um, in 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's different than the book. And you can understand what Somerset Maugham was trying to do, um, to convey to you.

Speaker A: Sayan, this was, uh, as freewheeling and deep and, uh, interesting as I had hoped it would be. Thank you so much. This was really a pleasure. Speaker B: Thank you. I'm a huge fan of your, your work and your writing and of Hummingbird. So yeah, I'm really excited where you've landed because, uh, they're remarkable. People and truly, truly independent thinkers. Speaker A: Yes. Speaker B: And, um, so it's a great place to land. So congratulations. Speaker A: Thank you so much. Speaker C: That's it. Thank you for listening to this episode of The Generalist Podcast.

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