Investing Like A Mystic: How Cyan Banister Finds Outliers (Co-Founder of Long Journey Ventures)
Cyan Banister 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, 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.
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[00:00] 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. 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. [00:21] them. 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 throttle.
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 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 [00:51] object. 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.
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. [01:18] Cyan Bannister has written that she is never playing the game, but she appears to be playing. [01:24] At 15, that meant sitting on the curb reading Kurt Vonnegut. [01:28] to capture an older crush's attention. [01:30] Today, it's an app description. [01:33] of how she's built one of the most successful investing track records of her generation. [01:37] with early checks into Uber, SpaceX, DeepMind, Niantic, Postmates, and Anduril.
[01:43] They named just a few. [01:44] Cyan now co-leads Long Journey Ventures, a fund dedicated to backing [01:49] Tex Magical Weirdos. [01:51] In our conversation... [01:52] Cyan shares her evolution from lifelong atheist into a believer in non-local consciousness, [01:58] Her job as a professional daydreamer, as she describes it, [02:02] and why brain-computer interfaces [02:04] are primed to break out over just the next two years, in her view. [02:08] We also cover why she's building a drive-in movie theater for golf carts. [02:12] and the Somerset Maugham novel, [02:14] She thinks everyone on Earth should read.
[02:17] I'm Mario. [02:18] And this is The Generalist. [02:19] This episode is brought to you 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. [02:30] Finding a compelling and distinctive company identity [02:33] is essential to breaking through the noise. [02:35] That starts with a great name and a great domain. That's exactly the thinking behind dot tech domains. [02:41] for companies building in tech, [02:43] tech domain gives your project a clean, confident identity from day one, instantly communicating what you're building.
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[03:27] With Brex, you get high-limit corporate cards, easy banking, and high-yield treasury. [03:32] plus a team of AI agents [03:34] that handle manual finance tasks for you. [03:36] They take care of things like expenses, [03:39] all according to your rules, so you can move faster while staying in full control. [03:44] One in three startups in the S. already runs on Brex. You can, too, at com slash Mario. [03:53] 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 who seem to occupy different pockets of the future, you are certainly one of them. So thank you so much for being with us. [04:23] Thank you. 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... [04:36] a memoir that you've been sort of publishing bit by bit.
[04:40] And it's actually there that I wanted to start because there were so many interesting lines in the, [04:45] some of your pieces that [04:46] seemed like they revealed part of your personality and, uh, [04:50] Yeah, there's one in particular that I have been mulling over. [04:53] It's in a piece where you're talking about [04:55] being 15 and sitting on a, I think, a curb. [04:59] reading Vonnegut books and waiting for an older crush to notice you. [05:05] And you have this line, which is that you're never playing the game you seem to be playing.
[05:10] Yes. I wondered what it was that made you someone who always is in some sense obfuscating [05:16] what you're after or the game that you're playing well. [05:20] Let's run a thought experiment. [05:22] If... [05:22] Life is a game. [05:25] And again, this is a thought experiment. [05:27] All games have rules, right? [05:29] And so if you wanted to figure out if this reality that we live in [05:34] is [05:35] operating in some unusual way, the best way to figure that out is to run experiments and to do everything [05:44] you're not supposed to do.
[05:46] So if you think about human beings, they're mechanical. [05:50] by nature. [05:52] 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. [06:04] We say that that's just how it is. [06:06] But what happens if you start rolling the dice? [06:09] What happens if you start, you know, instead of going left, you go right. Instead of wearing... [06:14] pants you wear something ridiculous [06:18] you know, what happens when you really shake up life?
[06:21] And [06:22] For me, that... [06:24] has always been a guiding light for me. [06:27] And I keep a lot of these thoughts secret. [06:30] because... [06:32] I want to see if I do something [06:35] 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. [06:44] the purpose. Yeah, you [06:46] Tilt the experiment if you share too much. And in that particular experiment, I got the guy, right? Yeah, it worked out. And you read a lot of Vonnegut, which, you know, win-win.
[06:56] Exactly. Exactly. So I sat there and read a lot of Bonnegut. [07:00] And it helped that I kind of had an inkling that he liked Bonnegut. But, you know, eventually he did notice me and then it all worked out. [07:09] You know, I think. [07:10] That idea of [07:12] almost remaining, you could call it playful or childlike or open-minded. You know, it's one of those things that I think [07:20] adults struggle to maintain, you know, we, our brains, [07:25] sort of lose their plasticity over time in some sense if you're if you're not careful like [07:31] I don't know, have you had to make a really conscious decision to keep [07:34] pushing those boundaries for yourself or keep running these experiments so that it doesn't calcify [07:40] Yeah, I mean...
[07:41] It's a daily practice. [07:43] You have to weave it into your life. You have to... [07:47] really not take yourself too seriously. [07:50] We tend to do that. We tend to cosplay as adults. [07:56] And I think... [07:57] if you add a little bit of play and wonder, if you look at children, [08:00] especially in early childhood, they're limitless. They don't understand [08:06] a lot of boundaries [08:07] of thinking, of their environment, and they're just in explorer mode. [08:12] And everything is a new sensory experiment, right? And so I look at the world that way.
For example, today and yesterday, I've been running the thought experiment of... [08:24] if [08:25] I'm in an avatar. [08:27] It always starts with if, you know, if I'm in an avatar, [08:31] And I get to have this one human body [08:34] for a period of time. [08:36] And let's just say I'm a limitless person. [08:38] energy being inside of it. [08:41] There's only so many breaths. There's only so many leaves. There's only so many tears there. [08:48] There's only so many frustrations I'm going to experience. [08:52] And so... [08:54] When I think about that and I close my eyes, I'm so grateful.
[08:59] And I'm filled with so much joy. I recommend that everybody try it. [09:03] Like go outside and be like, wow, [09:06] I may not [09:07] Feel arrogant? [09:08] Like, it was pretty great. [09:10] you know, and [09:12] That will lift your spirit immediately and invite that childlike wonder in. [09:19] If you just stop and pause for a moment every day. So for me, it's a practice when I wake up. [09:24] The first thing I do is wiggle my toes. [09:27] You know, it's kind of like a boot sequence. You've got to be like, OK, I've got this hardware.
[09:31] my toes, I'm going to wiggle my fingers, [09:34] I write things... [09:35] on walls, I write things around my house. [09:39] that help remind me [09:41] Because I am mechanical just like everyone else. Yeah, 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. [09:53] And so I recommend if people want, [09:56] to start doing this, you know, the shower is a great place. You can write [10:01] Something on the glass.
[10:03] It fogs up, you can remember. [10:05] to be more full of wonder every day. [10:08] Hmm. [10:10] How did that sort of... [10:12] spiritual, philosophical, [10:14] posture come to you? Was that something you were [10:17] I don't know, raised in in some capacity, even if it's been transmuted, is that [10:22] 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? Well, where does that come from? [10:31] All of the above. So I was raised exposed to just about every religion you can imagine.
So my mother... [10:41] was deeply trying to find herself and her purpose and why we're here. And so, and then there was also free child care. So we got dropped off that, 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. My mother was also part of the Native American church. And so I was [11:07] ended up out of all of that experience becoming an atheist. However, [11:11] The childlike wonder was not... [11:15] I didn't think of it as spirituality.
I just thought about it as a way of living and a way of surviving. [11:22] 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. [11:30] You may as well [11:32] figure out some way to spark joy in yours and other people's lives [11:36] So for me, it was [11:38] fundamental. [11:40] to just my being. And if you talk to anybody who's known me for a long time, I've always [11:45] I had very little.
I was very poor. [11:47] And so the other thing is like, how do you, [11:50] maximize fun and happiness with very little money. So I was always the friend [11:55] And 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. [12:03] 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 endless.
But... [12:16] You know, that was part of my personality, but spirituality really opened it up. [12:21] And... [12:23] I had a very profound experience. It wasn't [12:26] exactly related to my stroke. The stroke started it. The stroke [12:30] started the question which is what is all this about? [12:35] You know, where does suffering come from? What is the purpose of suffering if there is one? [12:41] And that thought experiment [12:44] lasted several years and I asked myself have I been really really honest about [12:51] spirituality or if I just dismissed it because of my childhood.
[12:55] And have I ever believed... [12:57] any of it and the answer was no [13:00] I never believed any of it. [13:02] So how does one believe? How does someone get there? [13:06] Like, how do you... [13:08] trick your mind or convince yourself. [13:12] an invisible world. [13:15] you know, that no one and you can't see. [13:19] But I can tell you that once I got there... [13:22] for a series of experiments, I started seeing things. [13:26] experiencing things [13:28] that [13:29] are just bizarre. [13:31] You became more of a magnet for [13:35] weird things after being sort of, as you say, tricking yourself into becoming a believer?
Yeah, my life was already bizarre and weird and magical. It became more so, right? Let me give you some examples. This one is probably the most profound. Can I tell you the most profound one? Please, yeah. I was listening to something called the telepathy tapes. And if you haven't listened to it, I highly recommend it. For folks that don't know what that is, would you mind giving it, Preci? Oh, absolutely, yeah. The podcast is about parents and [14:03] who have children, both adult [14:06] and underage who have autism and are nonverbal.
[14:11] in many cases also have no [14:15] no ability to move. [14:17] their bodies. And so [14:19] or it's very limited. [14:21] What they discovered was that [14:23] These children were able to find things that the parents hid [14:28] over and over and over again. [14:30] And so at first they thought, well, they have... [14:33] Super hearing. [14:34] the ones that can move around and seek and look for things. And [14:38] Then they realized, no, it's not that. It's because they would... [14:43] 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've developed this... [14:52] you know, hypothesis that perhaps the children were psychic. So what was interesting was that they started displaying characteristics that were [15:02] 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 [15:15] but had never read [15:17] - Wow. - How do you do that?
[15:20] So I started thinking about that and I wrote down... [15:22] Every episode and I started writing down the commonalities between each of the people. [15:27] What were the stories that were the same over and over again? The number one thing was they all claim... [15:33] that they have sat or met God, sat with God or met God. [15:38] Oh, wow. So they all claim that there's a metaphysical school. [15:44] that they all go to. [15:45] So a university that's metaphysical. [15:48] 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... [16:01] wall and puts it on. [16:03] And... [16:04] he knows everything about what Aldous... [16:06] thinks or did or wrote that [16:09] And that's how he experiences reading a book. [16:13] And [16:14] I was like, wow. And what blew me away more than anything [16:18] was that they... [16:19] 100% all of them meet in this place called The Hill. [16:23] It's a place that has green grass.
[16:26] that thousands of them congregate at, [16:29] At one point, [16:31] The host asked how many people are on the Hill right now, and they just spat out a number, 2,173. [16:37] I was like, what? And [16:40] You can't get into this space unless they allow you into it. [16:44] a moderator of some sort or they're all moderators. [16:47] 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. Yes.
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... [17:03] There's something there. [17:04] And so [17:07] I started running my own experiments. [17:10] And I started targeting people in my life. And I just went to Spotify and, [17:14] And [17:15] just [17:16] typed in Sinda Telepathic. [17:18] Message to a friend. [17:20] 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 [17:27] And I tried to send a message to someone I have not talked to.
[17:33] in a few years. [17:35] 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. [17:44] 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. [17:52] Something from three 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... [18:02] It may have worked. And I say may have because... [18:05] I'm not a scientist, but I am a scientist. Yes, a scientist. A scientist. And so I was like, well... [18:13] You got to 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. [18:22] Now here's the weird one. So I did that one. [18:25] 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 were you doing last night at 10 o'clock? [18:34] Pacific, one o'clock my time in New York. [18:37] And I was like, oh, why? Because I never say. I'm like, why? [18:41] And they were like, well, I heard your voice outside of my head. [18:45] which normally you hear things inside your head, but, um, [18:49] The voice said, are you all right? Are you okay? [18:53] That is exactly what I sent to the woman. [18:55] who didn't get it. [18:56] So I thought, hmm, if you are emotionally blocked or you have negative energy towards someone, [19:03] Maybe it goes to the nearest node.
[19:06] of someone who loves you. I see. That's an interesting theory. Right? So I started charting all these things out and I was like, okay. [19:14] And I was like, well, what happens if you send [19:16] a picture to someone. [19:19] What happens if you get a group of people to do it? I got a group of people to do. I started getting witnesses for everything. [19:25] 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 [19:34] getting on a plane in Miami or Key West or something and suddenly saw a hummingbird in their mind and they thought of me and so they're going to go get a tattoo of a hummingbird.
[19:44] And I was like, wow. [19:47] So what does this imply? [19:48] Right. I was like, this is insane that I with these limited... [19:53] skills are able to continuously do this now here's where it's really going to blow your mind [19:58] So I'm down at a farm in Temecula. [20:01] in a grapefruit grove and [20:04] 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... [20:14] 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? [20:23] And I said, "Well, here's the thing. [20:26] I don't know. I don't know any of this, by the way. I'm not claiming that this is... [20:30] real. I'm just saying try it for yourself. [20:32] And I said, you know, the telepathy tapes, there is one episode where there's an African gray. [20:38] And a human. [20:40] It's human. And they separate them into different rooms. They show the human a picture like, say, of a red ball.
[20:46] And African Grey goes, Red ball. [20:49] Oh, cute. Or they'll show the picture of a yellow car, and it goes, yellow car. [20:53] So whatever she sees, the bird spits out. Just as I'm telling this story, all of a sudden we hear [21:00] Help me! [21:02] Help me! [21:03] 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. [21:09] that got left out. So we started looking around for a toy.
[21:13] You know, we don't find a toy... [21:15] 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. [21:24] And so he comes running to me. He's like, Sian, Sian, Sian, you need to come here right now. And I'm like, okay. So we go to the front of the house. [21:32] on the outside of the house on the screen window. [21:35] is a pink cockatoo. [21:37] Wow. Saying, help me. [21:39] Oh my gosh. [21:42] I can send you a video of this.
It's insane. And [21:45] I was like, what are the chances? What are the odds? [21:50] Wow. This is the kind of stuff I'm talking about. [21:53] It took us three days to find the owner of that bird. [21:58] We named it Tele for telepathy because we thought it's a telepathic bird. Yeah. And we found its owner, which was two farms down. So it's not a... [22:08] short distance, they came and claimed it and they said that normally... [22:11] 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. [22:23] And they thought it was dead. They were like, this is such a domesticated bird. There is no way we thought it survived. [22:28] So this is a miracle that you saved it. [22:32] And... [22:33] 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 its name Mumbles? And they said, because it doesn't say as many words as a cockatoo should.
[22:47] It has a very limited vocabulary. [22:50] And I said, well, is help me part of the vocabulary? And they said, no. [22:55] That kind of stuff keeps happening. So that to me implies that human beings have capabilities to [23:02] that this may not even be supernatural. It may not need to be spiritual. It may just be natural. [23:08] we might have the ability... [23:11] to communicate with one another or glean things from the environment and nature. [23:17] that [23:18] we're just completely unaware of or detached from [23:22] or don't understand how it works anymore.
And that's because we're so distracted. [23:27] It could be because... [23:28] of our ego. [23:30] So the ego plays a huge part of it. You've got to think of the ego as software on top of the hardware. [23:35] And the ego interprets everything that comes to it as... [23:38] I. [23:39] This is mine. It originates from Finn. [23:43] What if it doesn't originate from within? What if it's... [23:46] outside of us. So the thing I'm most obsessed with right now is non-local consciousness. What does non-local consciousness mean? Many people have studied this and they said, well, it is kind of interesting that [23:57] this happens but it's not always repeatable [24:00] It's not...
[24:01] you know, you can't get empirical evidence on this ever. [24:05] slippery. It always gets away from you. I suspect... [24:09] 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, [24:18] That may be... [24:19] I'm going to use some layman terminology here. Sorry for all the scientists listening. The universe. [24:24] is conscious. I have no other word for it. [24:28] but that we're all connected to this cloud of sorts. [24:32] And that you are a receiver.
[24:35] You're basically an antenna. [24:38] to get information. So if you talk to a lot of artists, like, let's look at the woman who wrote Harry Potter. [24:45] She says that she was on a train. [24:47] And the entire story of Harry Potter was just downloaded to her in a flash, in an instant. [24:53] 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. [25:00] Yes. 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. [25:07] 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 [25:14] And a lot of these startups and these entrepreneurs are starting to discover that [25:19] that there's this really interesting... [25:21] stuff happening in the background in your subconscious that you are completely not privy to [25:26] So, [25:27] There's some startups that I've seen that are starting to spit out [25:30] information that is two weeks old [25:34] like you thought about two weeks ago.
[25:36] that is still visible in a BCI. [25:38] Yeah, but not in your active, you know, thinking, not in your what we would call consciousness. [25:44] 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? I think in the next two to three years, we're going to figure it out. [25:56] and [25:57] When we do, you've got to think about there's [26:00] a dystopian view of it and a utopian view of it. [26:04] which is that means it can be manipulated.
That means that it can be used for, [26:09] dangerous and terrible things, but it can also be used for things that can uplift humanity. [26:14] and bring us to our truly, truly creative selves that we're meant to be. [26:19] you know, I think the sign of a good conversation that there's, uh, [26:22] A lot of things that you said that I feel... [26:25] so skeptical about the now I have to go back to and a lot of things where I'm nodding vociferously along with you. You should be skeptical. Anyone listening should be very skeptical.
OK, I started out as a skeptic, as an atheist. [26:37] I got here through experimentation, through mysticism. [26:41] I [26:43] 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. [26:55] Like, go read this stuff yourself. Listen to these. Yeah, run your experiments. Run your own experiments. Yes, I totally. I like that idea a lot. And I think I'm going to try. It's interesting.
I. [27:06] Never... [27:07] listened to the telepathy tapes, I read about them, and I think I reached the stage at which [27:11] 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, [27:20] One can go to think about it. [27:22] And so I'm excited to do that piece. [27:25] And then you're, I think the... [27:27] Have you ever read the book Impro? No. 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 philosophy of improvisational comedy and theater. And he talks about how Western... [27:44] ideas of creativity have become so ego focused. And so as a result, we become super blocked. [27:52] 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, [28:05] I am a channel for something.
And that's much more freeing. And I totally think that's true. [28:10] 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, you're [28:18] Yeah. Of who you truly are and you can feel it, you can see it. [28:21] Even when I watch Instagram, I can tell if someone's putting on a show and it's a video. [28:26] or if it's really who they are. Yes. And... [28:29] And so I think... [28:30] Art used to be very different, you know, even in the era of Saturday Night Live.
[28:35] early television... [28:37] I think we were seeing some of that creativity, that rawness, you know, coming through. [28:42] But now I feel like a lot of it is manufactured for a certain kind of viral outcome. [28:47] I can't say if it's good or bad. I have no idea in the long run... [28:52] how this all plays out. [28:54] But, [28:55] I do think there's something to just... [28:58] letting go of the attachment [29:00] to the outcome and allowing [29:02] yourself to be a vessel [29:04] for whatever comes through you.
[29:06] You know, you've been one of the... [29:08] Best investors, I would say, of the past 15, 20 years, your track record is truly astonishing. You know, SpaceX, Uber, many others. [29:18] How much of that do you do you attribute to what I would classify in this conversation as like an extreme high openness? [29:25] Like you seem very open to [29:28] any signal the world might give you and then a desire to like verify it for yourself. But [29:33] To me, that's almost one of the most underrated parts of a venture investor's job.
And [29:38] kind of under... [29:40] 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 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. [29:58] So I like to tell people I'm a professional daydreamer. [30:02] So one of the things I like to do is carve out [30:05] a significant portion of my week [30:07] to sit, [30:08] and ask these questions and run these thought experiments [30:12] and then visualize what that future could look like.
[30:15] in reality. [30:16] You know, are there market conditions that could make that possible? One of my favorite science fiction authors, Neil Stevenson, told me I got a chance to meet him, which I was really excited about. [30:26] He told me, I said, how did you get so much of our future right? [30:29] Yeah. And he said, well, one is I'm a historian, so you have to understand the past. [30:33] And two, you have to understand [30:37] How the money is made. [30:38] You can look to the future and [30:41] 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 because markets will drive things forward.
Right. [30:49] And so that's how he figured out the diamond age and how he figured out snow crashes. He figured out the financial incentives. [30:55] which is beautiful. [30:57] I can't say that I've always thought that way and I've made some mistakes because of it. [31:01] However, [31:02] 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 [31:09] it'll make 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 which uh [31:20] basically invented crowdfunding and [31:24] patronage for art ended up becoming...
[31:27] I would argue that OnlyFans is... [31:30] probably the largest outcome of that. [31:32] that economy. But here's another example of something that was too early that you can invest in later. [31:37] which is I was in love with this company called Cosmo. [31:40] that did delivery of like cough syrup, candy bars, video games under an hour, but it was based in a warehouse. And this was around year 2000, 2001. Oh, wow. And, [31:55] They went belly up because they couldn't figure out how to make the margins work. Yeah. But along comes Postmates.
[32:02] And they figured it out, right? Because you needed the iPhone. [32:06] You needed... [32:07] the ability to give them [32:09] provisioned credit cards. You needed the ability to... That whole system had to exist in order for that idea to exist. So, [32:17] That's one of the things to look at. [32:19] 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.
[32:33] They did not come from grinding and taking meetings back to back. Yeah. Like Uber came from thinking about the taxi medallion system. [32:42] I didn't come up with the idea of Uber, but I knew there was a problem. I knew there was a racket. [32:46] And there was a bottleneck, which was [32:49] Only a certain number of drivers can exist. [32:53] Because it's throttled. And that's a problem. [32:55] How do you disrupt that problem? I didn't have the answer to that. [32:59] You know, I met Travis at a boondoggle.
[33:02] thing in Hawaii. [33:04] And he wasn't pitching me Uber. [33:06] I just happened to notice he was interesting. [33:09] you know, and observed him. What was interesting about him? 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. [33:25] He was clearly the leader of everything. [33:28] And, [33:29] And he was on the bench at the time. He said, I just sold my company.
I'm looking for my next thing to do. And if you're an investor, that should... [33:38] ignite part of your mind and be like [33:41] someone to watch, right? Yeah. So I just put a pin in it. [33:45] And then a few months later, [33:47] I saw him pitching... [33:49] at Open Angel Forum. [33:52] UberCab. [33:53] Now, keep in mind, also, I had an Uber driver. My personal driver was driver number one for Uber. Another weird one. [34:01] Yeah. Gosh. And he kept handing me Ryan Graves business card. If anything, the universe, if it was conspiring in my favor, was basically hitting me over the head.
[34:11] Yes, not subtle. It was not subtle. And so is that incredible luck? [34:17] Sure, if that was the only thing I ever did, then I would say, yeah, that was just luck. [34:22] But then if you look at flock security, [34:24] You know, one day I was at the Four Seasons before the pandemic. [34:28] and people used to have lots of meetings there. [34:30] And I went there. And again, like if you were to ask a lot of people about me, I tend to be very quiet. [34:36] 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. [34:45] and listening, deeply listening. [34:47] Not just the words, but all kinds of things. And so I went into the cafe and I looked around and I noticed... [34:55] everybody's busy wheeling and dealing and having their meetings. And so I order my coffee and I get on the wifi and I noticed that on the wifi, [35:03] everyone's tethered their phone in a public manner. So there's [35:07] kpixel [35:09] And I was like, K's pixel.
Hmm. I look around and I see Keith Raboy. [35:14] And I'm like, oh, okay, he has a pixel phone maybe. [35:17] So then I see Travis K iPhone. [35:21] And I look over in the corner and lo and behold, there's Travis Kalanick meeting with someone. [35:25] I'm like, this is a great way to get Intel. This is crazy. Well, then I see Garrett Langley's iPhone. [35:31] And I'm like, I don't know who that is. So I Google search him. [35:34] And he is the founder of a company called Flock Security, which was in Y Combinator at the time.
[35:39] And I did not go to the demo day. [35:42] So I didn't know it was coming up. I don't know if he had pitched or... [35:46] Or what? [35:47] And [35:48] I remember a conversation. This is where observation comes into play here, right? A conversation at Founders Fund where we were wondering, [35:55] Is there a camera solution [35:58] that's crowdsourced of some sort, [36:00] that could eliminate or reduce crime. [36:04] Should we look for a company like that? And we all agreed we should. So I messaged my intern at the time.
[36:10] John Ludig, who's now a partner there. And I said, John... [36:13] what do you think of flock security and goes, well, it's on my list of people of YC I want to meet. [36:18] And I was like, well, he's just right across from me. [36:21] And he's like, well, walk over there. Say hi. Perfect. [36:26] So I walk over and I'm like Garrett Langley and he looks up at me and he's like, huh? [36:30] He's like looking around. [36:32] And I'm like, and I just... [36:34] It was a bit of a magic trick.
I said, I'm Cyan from Founders Fund and we would love to meet you. [36:39] And he's like, are you... [36:40] part of YC. 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? And I told him and he blushed. [36:51] And we were going to save this story for when the company went public, but [36:55] 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.
[37:05] But that company is what valued at $7 billion, $8 billion or something at this point and solves a huge percentage of the country's. [37:13] petty crime like yes bicycles and [37:17] lawn mowers and that also solves amber alerts and things like that. This episode is brought to you by Persona, the B2B identity platform helping businesses verify users, fight fraud, and build trust. Fraudsters are already using AI to spoof faces, voices, and documents, so your defenses need to adapt just as fast. [37:36] Persona helps secure some of the Internet's largest and most trusted platforms with identity verification.
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[38:15] Want to see for yourself? Generalist listeners get a free year of the starter plan. Head to com slash generalist and check it out. [38:24] And so I think... [38:26] You know, you have to be open to an opportunity presenting itself in the most unusual of places. [38:33] You know, Pokemon Go, that happened because I noticed my friends playing this game called Ingress. [38:39] And they were obsessed with it. [38:42] And whenever you notice humans' obsession, [38:45] pay attention. [38:47] Like, why are this early group of people, these early adopters, obs...
[38:51] chartering helicopters? [38:54] Yes. [38:55] What? For this geo game. Yeah. Looks like geocaching. Yes. Um, [39:01] And so I started playing it and I realized like, wow, this is amazing. If I could invest in this, I would. [39:06] But Google owns it. Lo and behold, they spin out Alphabet. And I thought to myself immediately, this is my one and only chance. [39:13] to invest in something I think is going to change the world. [39:18] 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. Yes. If you remember, everybody's doing this. [39:31] Yeah, yeah, totally. [39:33] And I would argue it was the closest we ever came to world peace. It was a beautiful moment. [39:39] 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, [39:46] This was like one of the more wholesome uses of.
[39:49] of technology and like, [39:52] Yeah, a really beautiful way of people finding these new connections. Why do you think that didn't stick as a as a form factor? [39:59] Yeah, human nature. [40:01] So, Pokemon Go is still quite large. They make billions of dollars. It's still played worldwide. [40:09] It was acquired recently and the company that acquired it also made Monopoly go, which is not [40:16] geolocation, but it's, I think Monopoly would be a natural extension of the technology. I would actually [40:25] talk about why didn't Harry Potter work?
[40:28] Because Harry Potter should be... [40:30] that should be, you know. Yeah, even bigger, right? [40:33] And I think part of it was because the lore started when Harry Potter was an adult. [40:38] And it should have started when he was a child. [40:41] And there should have been a sorting hat. There should have been this magical experience of going back to Hogwarts for the first time. [40:49] And instead, you know, for whatever reason, K. Rowling and Warner Brothers wanted it to... [40:54] to start later in the canon. [40:56] And I think that was a big mistake.
And so if anything, I think allowing IP makers or holders... [41:03] too much control. [41:05] over [41:07] the IP could be catastrophic if you have an insight where you know that that's not how it should go. But [41:14] That's probably why I posit, I don't know for sure, that... [41:18] you know, that didn't work out. But Pickman Bloom... [41:22] is still doing incredibly well. Anything that's like [41:26] rooted in Japan, really. [41:28] like has a global application. Like there's something about Japanese culture that translates really well in this regard. [41:36] The question I have is why hasn't there been another one?
And I think human beings are... [41:42] We love novelty. [41:44] 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. Yeah, our bodies are wired and trained, but there's some people who still use Pokemon to get out and walk. [41:58] to get out and meet friends. They still go to the festivals. They go to the meetups. They go out on special... [42:03] Pokemon days and catch special Pokemon. It's still happening. [42:07] It just looks a little different.
[42:09] 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. I suppose the part that's interesting to me is that like that hasn't been more of a launch pad for like a whole year. [42:22] new range of of experiences beyond even Niantic, right? Like that more people haven't sort of taken the Pokemon Go. Hard problem. I think people didn't realize how hard it is. They thought it was [42:34] easy but I'll tell you what the hard part is understanding where a human can walk and not walk [42:40] I don't know if you remember, but there were people catching Pokemon in police stations.
[42:44] And the police were like, no, no, you need to geofence this on baseball fields and all these sorts of professional stadiums. Exactly. So running into stores that they are even people's yards. Yes. 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 founder of Niantic, John Hanke, also built Keyhole. [43:12] and worked on Google Earth and Maps. [43:14] And so the way that I thought of Niantic is, [43:18] is it's a mapping company at the end of the day.
[43:21] And so Niantic Spatial, I think, is going to... [43:25] prove that out in the end so it's now a separate company and they don't do games anymore but they do [43:30] They're continuing on the mapping. And I think that's wise. I think it was a very good strategic move on their part. Well, speaking of a different kind of mapping, I'm curious to go back to... [43:39] the brain-computer interface thread. You mentioned, I think, you expect us to have a lot more answers even in two to three years. What do you expect to help us get there?
Have you just seen... [43:51] Yeah. The fact that we can take large amounts of data now and find... [43:56] interesting things in it that we couldn't do before without [44:00] Great expense. [44:01] I think is really breaking things open. [44:05] So all these entrepreneurs wandering around with spaghetti helmets is what they look like. [44:10] these little things and [44:12] and collecting data 24/7 [44:14] And then, you know, there's thousands of people [44:17] running these studies now, [44:19] And so you're going to get information that was previously unavailable. [44:24] And so that will enable a breakthrough of some kind.
Every week I read about some new, like I just read about a hat, [44:33] that allows you to type. I just saw the same thing. I bet the beanie, right? The beanie. So you'll be able to type without using a keyboard. And, um, [44:43] I remember I invested in Control Labs, which ended up becoming part of the meta Ray-Bans, the gesture. Yes. [44:50] Yes. And when they first showed that to me, it was so amazing because I was able to play Space Invaders [44:56] just by thinking about it and the micro movements in my arms.
Incredible. [45:01] So, [45:03] You know, AI is going to [45:05] It's going to be the age of the polymath. [45:08] 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. [45:17] you're going to be able to come up with outcomes that were previously, those disciplines didn't work well together. [45:24] are going to discover things. A great example of this that I always love to give
[45:29] is Paul Stamets, who's a mycology expert. [45:31] was walking through a forest one day and he saw some bees on some fungus on a tree. [45:37] And he thought to himself, well, that's unusual behavior. I'd... [45:40] I thought, you know, 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 for groves. [45:54] So I don't know if you remember, but Bee Die Off was the number one headline for many years.
Like humanity is doomed. The bees are dying. We're going to have to create little robot bees. Some mycologists solved it. [46:06] that's what we're going to start seeing is somebody that you don't [46:09] expect [46:11] you know, who studied fluid dynamics suddenly has a physics breakthrough or, you know, [46:16] you know, things like that are going to be really, really interesting with the, [46:21] because they're going to become AI enabled or AI enhanced. That's a really interesting framework that I don't think I've heard someone articulate quite before. To make sure I'm following, you're basically saying that, [46:32] Because AI sort of can help you close the knowledge gap on the areas you don't really understand, [46:40] you can then apply a different lens from your area of expertise and sort of make these sort of different juxtapositions and connections together.
Yes. Yeah, that's really interesting. That's a really good point. I hadn't really put that together. The level of creativity that's going to come just out of that will reshape humanity alone. I really like that. I mean, it's interesting that definitely... [47:01] corresponds to my experience with the technology so far, which is that [47:05] You know, you can, I mean, I'm sure you're doing this too, but like building a million things with cloud 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.
[47:21] Yeah, things like our EAs are making dashboards. Our meetings here at our office have completely changed because people who couldn't code [47:28] are suddenly able to dream up a way of [47:31] you know, sorting data that they never had before, because before they had to use an Excel spreadsheet or a notion or whatever. [47:37] 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 to [47:47] or the confidence. [47:48] Yes, they could understand engineering on that level.
[47:52] And so if you think about engineering being available [47:56] to everyone. [47:57] There's creativity in every human being. [48:00] That's one of the things that's special about humans that makes us so... [48:04] wonderful and beautiful. [48:06] An AI doesn't sit on its own and just [48:09] you can say, come up with 20 ideas. [48:11] but it's based off of its training data. But it's not going to think about... [48:16] A lot of things that only humans are uniquely capable of thinking about. [48:20] And so I think what's interesting is we need to start thinking about how [48:25] human work is going to change [48:27] to where we all become professional daydreamers.
[48:32] We all become... [48:33] Or artisans. Like I think some more people are going to start using their hands. I think there's going to be beauty and imperfection. [48:40] which goes back to the diamond age and neil stevenson's predictions about the future there was this uh [48:46] society called the Victorians [48:49] who [48:50] 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. [49:10] And so... [49:11] It could be that Etsy and companies like that just soar. [49:16] 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... [49:24] The novelty might be in the imperfection in the future. [49:27] not the perfection. But a human being now can sit and think, gosh, I've always wanted this service to exist. [49:33] And now it can.
[49:35] And eventually you'll be able to vibe products like physical objects. [49:39] able to say like [49:40] Like vibe manufacturing is going to be a thing. [49:43] 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... [49:52] newly minted millionaires across the world. [49:55] 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.
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