"Dig Through Your Couches. SpaceX Needs It." Cyan Banister on Luke Nosek's Pitch

[00:00] Congrats on SpaceX. Thank you. That's my first check. Luke came over to our house and he's like, Manisters, I need you to dig through your couches. Anything liquid you have, I need it. SpaceX needs it. So Luke and Scott convinced me to put everything that I made in Ironport when we sold the Cisco into SpaceX. I think the two of us combined are definitely number one in the world. One of the things I like to ask people is what worries you? Peter used to ask me that at Founders Fund.

And it's a very important question because what excites you is interesting, but what worries [00:30] Do not shy away from it. It does not make you anything that anyone's going to accuse you of. You don't eat babies. SpaceX, Andrel, Uber, Zappos, PayPal, Affirm, Flexport, Checker, Density, Flock Safety. That's a really cool company. Brave, Zen, Control Labs, Depop, Substrate, also very underrated. Carta, Together AI, Turing, Postmates, Niantic, Cargomatic, Diamond Foundry. Very interesting. Upstart, Fivetran, Forge, Opendoor. Had a lot of fun with Kaz. We did a really, like, recent interview there. [01:00] Palm, TrueMed, and Cusseau.

So what's your favorite? [01:13] All right. So we are at Long Journeys HQ. It's called the Boobies Place. The Bubbies Place. Bubbies. Bubbies Place. Yes. [01:26] Bubby might have some boobies, but it's Bubby's place. [01:31] And we're in a very special room right now. With Cyan Bannister, the star of... [01:38] One of the stars, because I also called Dylan the star of Mafia. You're all stars of Mafia in your home. Yep. [01:47] Well, we are in Long Journey's headquarters, and this room that we're in right now, they call it Cyan's Lair.

[01:54] Oh, I have a tendency wherever I'm at, including at Founders Fund, I was behind the bookshelf that turns. I really like darkness and artificial light. [02:06] is not my friend. So I'm going to tolerate this today, but in general, I like natural light or dark. And so if you come to the office, you'll, you'll tend to find me in here. So tell us, I mean, if you're not looking, you should watch the video. If you're not listening, uh, if you're listening on Spotify, look at the video right now. We're in this crazy, like very beautiful, charismatic room [02:36] entirely around all the walls down here in the lower level so everything's covered what is this so this is done by an artist named dave zacken who lives in brooklyn and i discovered him on instagram [02:49] I was just scrolling through Instagram one day and I saw this guy wearing a pair of glasses that were that look like 3D glasses, but they're red and green instead of red and blue.

And I had to wear those after I had a stroke. And so in order to learn to walk again. [03:05] That was one of the things I had to do. And so I recognized and [03:09] immediately thought, here's a person who's obviously going through something that I went through. I want to learn more about him. So I started looking at his feed and realized he was a ceramicist. And he was stuck in the hospital for a month where he couldn't make ceramics. Oh, wow. And so his friends started bringing him pieces that he could paint in bed and ways of making an income.

[03:30] And I thought to myself, if I ever get a chance to buy his stuff again, if he ever makes it again, I'm going to buy as much of it as I can because I want him to start bringing a lot of this joy to the world. And then one day I had this fantasy that I was like, well, I wonder if Dave Zakin, he's made a full recovery at this point, but I wonder if he would do a mural for him. [03:50] And I would love to see him. I would love to see a hotel like this.

Yeah, it would just be super fun. And I reached out to him and I said, hey, can can you come paint our office? And he's like, you're not going to believe this, but I'm painting my first mural right now as we speak. And he sent a picture of himself up on the ladder. So I figured it was a sign. And we flew him out here and he spent a week living pretty much in this room and painting the walls. And a lot of this is organic and unplanned. [04:16] It was just based off of what he heard us talking about, you know, the vibe of the team.

And he would just come hang out with us for a little while and then come down here and paint. But what I love about Dave is he finds pottery that has been abandoned by high school students or ceramic studios. Yeah. And what he does is he repaints it and reglazes it, basically puts it, fires it again and gives it a new life. [04:46] cups I have around my house and they all have a sense of humor. Sometimes it's a commentary on the world. [04:52] But I'm a big fan. [04:54] There's so much going on right now.

Yes, yes. In case you didn't know that. Yeah, I'm also a big fan of the Alameda Flea Market, and I go about two, three times a year, and I just went and found these flowers. And they were only $30 for, I think, both of them. What? Yeah, and so I love walking around town with them. Oh, my God. It just brings a lot of joy to people. And is Dave also the ceramicist of the hammer? [05:24] so that I can promote her work. I have not met her in person yet.

[05:27] But a friend of mine bought these for me, so I didn't find them. That's why I don't know much about them. This is so fun. I just can't imagine what your house looks like if this is your office. Yeah, it's a different kind of crazy. It's different. I like to mix it up. It's not quite like this, but I look like... [05:45] If you were to go to Goodwill for your design, [05:49] I know that sounds weird. Yeah, it's more thrift store oriented. And everything's vintage. And everything's odd. I tend to like...

[06:00] If people come to my house, I gauge my success rate by... [06:04] How many things do they touch without my permission? [06:07] Oh, interesting. Yeah. So what happens when you see something and you, it sparks like your inner child. Yeah. You start just rummaging through, you know, drawers and stuff and you don't even think to ask. And if people do that, I actually know I've done my job right. [06:21] because I want it. I actually want people to rifle through things and feel [06:26] so at home that [06:28] They can play.

And so like I have bowls that look like banana bowls that are filled with fish and then people pick up the fish and they start throwing the fish at each other. And there's no prompt there that says to do that. It's just kind of implied like. [06:43] this is a silly place. I'm free to be silly. Is that the most, like, touched thing? The fish. That's what we go for the most? Yeah, the fish, the fake snowballs. I mean, that's obvious. Like, it's like, oh, there's snowballs. Let's throw them. There's also, like...

[06:57] Weird collections of fried eggs because I don't like eggs, but I like the way fried eggs look. So I have like a wall of fried eggs. Um... [07:07] And just people laugh when they see it. So that's the other thing is if they laugh and chuckle. Yeah, I know I've done my job. Yeah. [07:13] You know, so in general, if you were to come to my house, I want you to play. And you don't like candles, right? So there's two candles on the wall. What do those represent? Yeah. [07:22] I hate candles because my mom accidentally burned down her house when she was younger with a candle.

And I heard about it growing up. [07:32] And so I had this fear of candles. So I've never liked them. [07:35] But these candles are an addition by Lee Jacobs, who's my co-founder of Long Journey. And the idea is that one candle is witness to the other. So you basically find a founder that has a spark. [07:48] and their flame is going, and so you light your candle off of theirs, and then you hold that flame so that in case theirs goes out, [07:54] they can come back and get their flame back.

Oh, wow. [07:58] And so it is a it's an interesting concept that we call the second believer. The second believer holds the flame. The first one has to ignite it first, though. [08:06] That's, yeah. [08:07] That's good. Yeah. And I know no one can see this in frame, but I think it took me like a second. It wasn't until Lee or maybe you explained it to me, but what does the Long Journey logo mean? Yeah. So it's an eye and a lot of people who see it think it's the evil eye.

It's the all-seeing evil eye, which, by the way, it says it's called evil eye, but it's actually a good omen or supposed to look... [08:32] over you and it's very popular in Greece and in other places that aren't the United States. But it's actually the eye of a sheep. [08:41] and um [08:43] People say, well, why is sheep, like being a sheep is bad. Is being a sheep bad? You know, it's, I really like. I think it's bad. Bad. Yeah. It's bad. [08:56] That's good. That's really good. I like taking phrases that we just say and then turning them around and seeing if there's a falsehood in them.

So, for example, I. [09:07] Something is better than nothing. What if nothing is better than something? In many cases, nothing is way better than something. [09:15] So, you know, I thought about don't be a sheep. [09:18] And so I was like, well, [09:20] When is being a sheep a good thing? [09:22] And how are sheep led? [09:24] And so usually there's a sheep dog, there's a shepherd, but there's also a bellwether. And a bellwether is the sheep that has been selected to lead all of the sheep. And the sheep follow it.

And then if the bellwether disappears, they anoint another bellwether. But there is a leader of sheep. And sheep have to follow something because... [09:45] If you think about it, you're outsourcing your [09:48] trust to someone else. And if you think about Apple, we all use the iPhone [09:53] Does that make a sheep? [09:54] You know, or are we trusting Apple and an entrepreneur to create an experience that we will inhabit and use every day? And so I think there's something to... [10:04] being comfortable following a leader. [10:06] And then obviously there's a leader of the sheep.

So there's someone who has to look. If you look at the eye, it's looking sideways. And that's because you want the bellwether looking off to the side to see what's coming. [10:18] and to see what's non-obvious. [10:21] And so it's kind of a play on this concept of, [10:24] You know, don't just take a sentence. [10:27] at face value and not like [10:30] play around with it and play around with the concept and see if it holds true. But that's, you know, where it comes from. [10:36] And its name is Bellwether.

[10:38] Wow. Hello, Bellwether. I think that's a good lead into why you are so popular right now, Cyan. You are one of the stars of Mafia. So for people who don't know what Mafia is and what Mike Solano put together for Founders Fund, could you explain it and who is also involved? [11:08] cards and you get assigned a role that you're either a townsperson villager [11:13] You're a mafia member. You're a sheriff. [11:16] or you're an angel. Angels can wake up in the night, you all go to sleep at night, [11:23] Angels can wake up at the night and they can actually try to see or save somebody.

So they can save themselves or another person. And if you watch the show, you'll see that it alternates like they can only save themselves once every other turn of the night. And then the sheriff, the sheriff can see who is mafia and who isn't during the night. And then the mafia kills a villager or a sheriff. [11:45] a townsperson or a sheriff or an angel at night. And when you wake up, it's a big game of kind of witch hunt. [11:52] At first you just have to kill somebody. [11:55] and you have to coalesce on who to kill.

And then afterwards, it's a game of deception and lying. [12:01] Because you've got to gather information from your team, well, they're not even teammates, but from the people around you to try to figure out who's the killer. [12:10] And you go off of my game that I like to play is the metagame. I like listening to sounds. I like watching people's eye movements, whether or not they protest too much, whether. [12:21] who they seem to be bonding with, who they seem to be [12:26] forming an alliance against all of that as a tell and information, because you have to assume that they're all lying.

Yeah. You know, if you're going in with imperfect information, you have to like figure out what your strategy is. And if you watch the show, you'll see that everybody kind of has their own strategy. And, uh, when I first got there, [12:44] I asked everybody at the bar that I talked to who's the best player. I said, have you guys played with each other? And they're like, oh, yeah, you know, I played with Dylan, and Dylan's really good. [12:53] I kept hearing from multiple people that Dylan is really, really good.

So I was like, well, Dylan's got to go. If I am mafia, Dylan's gone. And I was like, who else? And they said Moxie. [13:06] Moxie got a lot of hate. A lot of hate. But as you can see, Moxie's quite good. And he lasted a lot longer than I thought he would. Yeah. But we all knew he was good, so we were trying to get him out of the game. And you want to take out anyone who's clever enough to, [13:21] or is a good liar. I did not. The thing that shocked me the most, though, is I didn't realize how good Trey could be.

Oh, my gosh. Like, I mean, Trey's a badass, but like, I just didn't. [13:32] realize like that he would take us all the way home. You know, that was no easy beat. Yeah. So you mentioned like, I think it was the beginning of the last game. Like if people listen to you, you guys would have won. We would have won. They would have taken out Sam and Ryan. [13:49] And, um, [13:50] you know, eventually figured out that Palmer... [13:52] you know, was one. But yeah, so that I get it was really odd to me because I said, you know, the table moved and it turned out I was surrounded by mafia.

I had [14:02] Palmer to the left, and then I had Brian and Dylan were all mafia. And basically what happened was they were all leaning on the table, and when they got up to kill, the whole table just like – [14:13] And it was so obvious to me that I was like, there was something going on around me. And so then I watched for the table to move in that third round. It didn't, but I heard some rustling. [14:23] when they woke up in the night. [14:24] to kill. And I was like, it's gotta be, if I'd stayed in the game, I would have gone after Sam.

[14:29] Um, [14:30] So I'm surprised that they didn't use the intel, but maybe they just didn't. And they killed you then after that? Yeah! Yeah, of course they did. Yeah, they killed me. Yeah, you knew too much. Too quiet. Apparently if you're too quiet and you're observant, it gets you in trouble. They automatically assume you're trouble. What do you think the best strategy is through all of it? Oh gosh, it really depends on the dynamics of everyone there. I don't recommend that this game be played with couples or best friends or people who...

[14:59] Because I've actually seen people get into real fights because of mafia and werewolf, which is a game that's very similar. And it goes beyond the game. They're just like, I can't believe you would say that about me. I can't believe you'd call me a liar. I was telling you the truth. Can't you tell? And so I recommend you don't do that. [15:17] For me, I mean, I have... [15:19] I lied. I have played the game before, but I played it mostly as werewolf. I think I've only played Mafia once before, and that was in Hawaii.

[15:29] But I'm not super used to the terminology, so I figured it was believable if I was just like, I don't really know how to play this game. And they did buy it, and that helped. But that's only going to work. [15:41] you know, a few times. Well, you've now been out. I've been outed now. There's millions of views on that one. Yeah. Now. [15:47] But that was my first time being mafia or a wolf. [15:51] I have never been a killer before. I've never had to lie like that. And so I got to say that was challenging.

Really? It was super challenging for me to lie. I do not like it. [16:01] And it made me very uncomfortable. And I thought you could absolutely tell. [16:06] But Dylan was just like, I couldn't tell. You're just very hard to read. [16:09] Yeah. He's like, you just look kind of like, you know, very difficult to read, but it was super fun. I really hope Solana does a whole other season. [16:19] I think it would be fun to see some different [16:21] people in our industry go in. [16:24] and have some of them come back yeah you know because i do think there were some really good players in there that should return absolutely i thought it was i mean one the format was like really interesting mike always comes with like the craziest ideas then and then now i haven't understood i didn't know all those people so it was like now i know who ryan is now i know who josie is now i know who moxie is it's like really cool it was like a really interesting way to like [16:54] like not everyone knew each other either so it was like a cool kind of like just like yeah some of us know each other well and some don't and so for me even it was really interesting like um [17:04] I've maybe talked to Brian Johnson a couple of times over, [17:08] like dms um talking about health stuff but like i've never actually spent that much time with him so [17:14] It was really fascinating to see what he's like in person.

And then, you know, I love Moxie and [17:20] Palmer and Trey and the whole Founders Fund team, but I haven't been able to spend this much time with any of them in a while. And so it was really, really cool to get that experience. And plus, it was in Tosca. [17:32] which is where the famous PayPal mafia photo is. Really? Yeah, so it's the exact same space. I didn't know that. Yeah, so the exact same picture. [17:39] If you look at it and then you look at where we're playing mafia, that's what makes it so funny.

No way. Yeah. Oh, my God. Yeah. So it'd be super cool if you got some of those folks on. Yeah. I would love to see Radboy and, you know, Peter. Yeah. That would be so cool. That would be so cool. So cool. I don't know if Peter would do it, but who knows? You never know. Yeah. Hopefully. It's funny. Like, I've interviewed a handful of the PayPal mafia at this point, and I don't know. [18:05] keep on asking each one of them if there's a group chat, they keep in touch and they're like, Nope.

Some of us do not talk to each other anymore. Yeah. Some, some of them don't. Um, but some of them are ride or dies, right? Like, like, [18:18] there's always been this unspoken [18:21] truth among a few of them that no matter what someone did, you back them. And so there's this, or you fight for them. Like, you know, I just know that if Luke Nosek or Max Levchin ever needed anything, I'm at the drop of a hat, they're like family to me and I would just rise and go, you know, do whatever it took.

And so there's a level of sort of family that comes with this group as well, that is above and beyond sort of what they did as a company together. And so in that sense, [18:51] kind of like a mafia, 'cause they really, really help each other out. [18:53] I feel like Elon would go. [18:55] Mm-hmm. [18:56] I think he would. So was was there anything that was recorded that wasn't kept in? Like, are there any dynamics we didn't get to see? I would imagine. Yeah, I don't I don't know if I'm allowed to say because it might get me in trouble.

Probably. But yeah, there was some really spicy moments between a few of the people and they got cut. [19:15] So maybe someday Solana can do like an outtake. [19:19] Give us like a quick blooper reel. [19:23] Quick blooper reel. Well, there's a lot of things that were back in the sushi room. Mm-hmm. [19:28] Because keep in mind that the cameras were rolling from the moment [19:32] the game starts and the game ends and there's a lot of banter back there. And there was a lot of like gotcha moments where people realized like they'd been lied to or whatever, and they can only put in a certain amount of minutes of that.

And so if you imagine there's like a lot more of it. Oh my God. And, um, [19:49] just really funny comments and side comments. Um, [19:52] You know, some fun stuff, which I won't get into with Palmer and Sam Altman. [19:59] They're friendly. It wasn't that. It was just, you know, just banter that you wouldn't imagine playing. [20:04] You're just like, wow, I'm sitting in this room and this is happening. Yeah. Yeah. [20:09] It was all friendly. It was just really interesting how much, because it's kind of like reality television, you cut a lot of it.

Yeah. So maybe they'll do like a blooper reel or something like that someday. It'd be fun. I'm excited. Hopefully, Solana, you make a season two. Oh, I hope so. I would hope so. I really, really hope so. Yeah. Solana made us swear to secrecy because this was filmed, I want to say six or eight months ago. No. Really? [20:39] tell my partners here about it. What? And, um, [20:43] And I actually was really proud of not telling anybody because the whole firm got to be surprised by it. Like just on random ones they have under noon, they were like texting me and they're like,

[20:52] What? I'm like, surprise. [20:55] I just knew you'd love it. [20:58] So why did he wait so long to release it? Editing. [21:01] Really? So keep in mind that this is not, this was a big production. So every single one of us had a camera on us. So there's one camera per person. And in the back room, there's a whole fleet of people that are editors. It's like a real reality TV show. So every camera had a person and they're there tagging interesting moments, right? Like so that when you have to go through it and edit it later, you've got to take the footage from every camera of every single person, including like, [21:29] There's aerial cameras, there's cameras on the table.

So on the table, there was this round thing to each, there was a lens at each one of us. - Yeah. - So like a poker game, you know? [21:38] And if you see like the different reactions where they can like, that was not like a camera person. [21:45] So that part I think was probably challenging to put that all together. I can only imagine. [21:49] Um, [21:50] just how much thought and preparation. It looks effortless, but it was not. I mean, if you saw the set and you saw how many people were involved, there was like, [22:00] probably over 30 people just on the camera production side for that.

[22:04] Wow. Yeah, it looks simple, but it was definitely not simple. [22:08] It would be very hard to produce that show. I would imagine. Let's put it that way. Yeah. So Mike thought about it for years. You know, years and years and years. Like how... [22:17] And many people have attempted to make this show. Yeah. This is not the first time, you know, Chris Saka and a couple of other people tried to make it. [22:23] with werewolf. And I ultimately could not figure out the right [22:29] way to display it on television and you know mike's a genius so he figured it out yeah danielle strachman we did an interview on like early teal fellowship days probably like a year ago um and now with 15 and 17 like uh it's really cool to see how everything's been going but she said like early days they would play that game for like community building and that kind of thing and it kind of evolved like that what would be cool as an addition and maybe you guys do this now is [22:59] Professionals.

Yeah, that would be great. Ah, we should add that. Yeah, I am. I've made a lot of friends playing mafia and werewolf. I have found. [23:10] some founders through it, [23:12] If you think about it, it's kind of like poker or golf. [23:16] It's one of those things, if you get invited to it here, you should go, because it's a great way to take down barriers and get to know somebody and laugh and have a good time. [23:25] Without like all the small talk, you know, so you can just like dive in, do something together and.

[23:31] get to know how somebody operates and how they work. [23:35] or lie. You can learn how they lie or don't lie. It's a really interesting thing. And maybe it's more popular among us because we're not [23:44] you know, we're neurodiverse here. And so maybe it's fun [23:47] for a lot of us to try to figure out [23:50] how people are presenting and the masks that they wear. Yeah. [23:53] Yeah, that is really fun. I recently had Brian Singerman on who gave you a really great shout out. Love Brian. Yeah, he's awesome.

It was so much fun talking with him. And he was talking about how the games he's he's grown up playing board games, like table games, all that kind of stuff. And it's shaped the way that he invests and like the things that he looks out for and getting skill points and all that kind of stuff. He got me into board games. Really? Yeah, he did. We used to have a board game club, a board game of the month club that he's a [24:23] Thank you. [24:23] He subscribed to it. I had all my friends subscribe to a board game of the month club and they would pay me $40 a month.

$40 a month. And then what I would do. What are you doing? Um, [24:34] You know, I got my side hustle, but they would pay me $40 a month. And what that would go towards is I would buy a game that was 30 minutes or less of gameplay, send it to them in advance and then have a game night. Because I realized I really don't like it when you have a game night and people show up and they're like, what are the rules? And then you spend an hour to two hours getting them caught up on how to play the game.

[24:54] And then you can finally get to the game and the whole time they're confused. Yeah. It's not fun, especially if you're really into board games. [25:02] uh, Splendor ended up being one of our favorite games, Machi Koro, um, [25:07] I'm trying to think of Settlers. And so you would send these out in advance and then they would show up and you would just immediately get to gameplay. And it was super fun. And Brian was a part of that group. And he taught me how to play something called Through the Ages, which the setup for that game, it takes two hours.

[25:23] just to get the little pieces out and the little, like, all the crap that you have to do. Like, it takes a long time, but he is a champion at that. [25:31] Like when it comes to strategy board games, I have never met anyone better than Brian Singerman. [25:36] Really? Yeah, he's the best. [25:38] This episode is brought to you by Brex, my favorite. You become what you spend on. And I refuse to spend my time on work that shouldn't exist. Expense reports, receipt chasing, and manual closes. The companies building what's next from Vercel, OpenAI, Anthropic, Granola, and DeepGram.

[25:58] all made the same call. They all run on Brex. Brex is the intelligent finance platform that combines cards, expenses, and banking into a single stack with agentic finance built in. AI agents that handle expenses automatically, [26:13] Enforce policy before spend happens and close your books in minutes. That's why Sorcery runs on Brex, so I can spend time on building and not busy work. It's time to get Brex AF. Learn more at com slash sorcery. That's B-R-E-X dot com slash S-O-U-R-C-E-R-Y. [26:36] Bye. [26:37] Turing is training the next generation of AI with tasks that require real expertise and real world judgment.

That's why companies like NVIDIA, Anthropic, Salesforce, and Gemini partner with Turing. Turing builds realistic reinforcement learning environments and data systems based on real operational traces, the kind of infrastructure Frontier Labs need to train superintelligence. Visit com slash S-O-U-R-C-E-R-Y. [27:05] What do you think all of these games and strategy games and just kind of having this like childlike kind of playfulness? I mean, it's it's kind of like part of the Silicon Valley DNA in some sense, like this is happening. It happens like. [27:19] Why do you think that, like, crafts such great imagination and, like, different companies and all this kind of stuff where, I mean, some people do the drug thing, but, like, there's also the crew that does more of these kinds of, like, games and, like...

[27:33] community? Well, I think, again, going back to neurodivergence, I think, um, [27:39] There's some of us that don't like to go to a party and stand around with a cocktail and say, hey, what have you been doing? And and like, what have you been thinking about and what excites you? [27:49] And instead, just drop into something where you're collaborating right away. You're working on something together right away. And so poker is good at this. You can sit at the table. You can banter. You can share deal flow. You can talk about your family if you want or not.

[28:03] You know, but you're doing something. And the same thing with strategy games is you can kind of see how somebody plays a game. [28:10] And you can see like what their skill level is like, [28:13] Do they really think ahead five, six turns? Do they really understand the mechanics of the game? Are they thinking about the math of the game? Are they thinking about the psychology around it? What level are they playing at? [28:26] is something you can gauge in these games. And so I think that's why they're so popular.

[28:31] I know that there's groups of people that play chess. There's groups that do magic, the gathering there's groups that do settlers. I know that, um, [28:39] I think Reid Hoffman, for a long time, did Settlers of Catan game nights. [28:44] and people would go play them. [28:46] Uh... [28:47] You know, there's people who have like, [28:49] more casual games like I used to do that are 30 minutes or less because I wanted people to be able to [28:54] play a couple games, [28:56] socialize with people and then bounce because they're busy.

And also just not spend many, many hours trying to figure out how to play the game. [29:03] So it just really depends, but I think it... [29:07] It's a great reflection of their inner world. [29:10] You're also a prolific poker player. [29:15] I've seen some videos. Yeah, it's really funny because I don't really play a lot of poker, but I'm known for it, which is weird, right? Mm-hmm. [29:24] And part of it is because I host the charity poker tournament. [29:27] Once a year for inflection grants and for Edge Esmeralda, we at Long Journey basically put this together with their team and we raise money for these little micro grants, these $2,000 grants for young people who write essays to us.

And so I got known for being a poker player because I made it to the final table there once. But to be honest with you, I'm not that good. [29:49] Really? I'm really not that good. I probably could be better. [29:52] if I tried, but there was a poker... [29:56] tournament sort of thing that I fell into kind of on accident. And I ended up at this table playing with Steve Aoki and, [30:03] um, ninja, Phil Hellmuth, [30:06] And I ended up beating Phil Hellmuth, which was legendary. And part of it was I was playing very, very conservatively because I – [30:15] One, I didn't realize the thing was live.

I did not realize people were watching. - No. - I had no idea, none. Two, and then I didn't find out, so the commercial break or whatever the break was, we went to this break and they were like, [30:28] Just so you know, everybody can see your cards. [30:30] And I was like, wait, what? [30:31] And they're like, yeah, every time you put the cards on the thing, like it goes up on the television. I'm like, television? And I'm like, what? And they're like, yeah, we're streaming this to all of Ninja's fans.

And I'm like, what? Oh, my God. And so this guy comes up and he's like, [30:45] What would happen if you bluffed once? [30:47] Just once like do you bluff and it's like no, I don't bluff and he's like I [30:51] Just one time. [30:52] So I came back and I waited for a hand [30:55] in which the pot was large enough... [30:57] And I'm like, how can I convince myself that I have the best hand? Because that's the only way I think I can bluff is if I think I have the best hand.

[31:05] And so I was just like, I have the best hand. And then I just turned around and I acted like I had the best hand. And I was like, this is great. I have the best hand. So the look on his face, he was just like, there's not there's only one two cards you could have. [31:18] And he's like, do you have them? [31:20] which means he doesn't have them. [31:22] Right. So so he's on tilt and he's like. [31:25] *sigh* [31:26] So finally he folds. [31:28] And I won the pot.

And it was like crazy because everybody was just like, I cannot believe. And then he was on tilt the rest of the time. It was fantastic. How good. How do you find yourself in these situations? That's kind of my life. My life is a series of these types of events. Even before. [31:46] I was financially successful before I was who people know today. I tend to, I always tell people that if I were a tarot card, I'm the fool. [31:56] Um, I walk off ledges expecting everything's going to be fine, not literal ledges, but you know what I mean?

Yeah. And I do honestly believe that everything's going to work out. [32:05] And sometimes it doesn't seem like it's worked out. But in the long enough time horizon, you look back and you're like, I wouldn't be here talking to you if all those things didn't happen. Like they all had to happen. And so I have this attitude that everything works. [32:20] just kind of has to happen the way it does. And it puts me in these strange positions where suddenly, like, I did not go to Vegas to play in a poker tournament.

I was there to help a startup that I invested in called Going Public. And they asked me to be an undercover reporter. Really? And so I dressed up like a blogger. I put on a wig. It was a terrible wig and nobody figured it out. And I, and I was just trying to like, [32:43] get them to say things that they wouldn't normally say. And then at the end, when I revealed myself, they're like, Cyan, come play with us in this poker tournament. [32:52] And I was like, oh, okay. So I just like wandered in and I just started playing and I didn't realize.

But that's kind of my life. Like a lot of the times I'll be in these situations where I don't – the thing that I think – have you ever seen the movie The Man Who Knew Too Little? No. It's with Bill Murray. It's with Bill Murray. [33:06] It's fantastic. Basically, without giving it completely away, he thinks he's in a game. [33:13] like a role playing game where people are doing things for him, but he's actually really running with like criminals. [33:20] And he has no idea. But that's my life. Not that I'm running with criminals.

[33:27] a show of sorts, like a Truman show. And I'll show up and weird things happen. And I'm like, wow, that's happening. That's really neat. That's interesting. And I just kind of roll with it. What has that taught you about human behavior, though? Because most people don't live like you. They're not as optimistic. Mm-hmm. [33:44] - They could be. [33:46] How can they be? We have this misconception that our personality is fixed. And we say, this is just how I am. And I hear people say this all the time. I'm a Scorpio.

I can't help it. I was born in November. I'm Irish. I have a temper. And the list goes on and on and on. And these are excuses for a behavior that you're unwilling to change or don't know how to change it. But if you actually become very introspective, and I know Marc Andreessen says, don't do that, but I spend a [34:16] And I would say that he's wrong. And I'd love to have a chat with him about this. [34:20] you can actually surgically go in and alter your personality [34:25] where you can actually change these things.

But it takes effort and time and a lot of facing the ugly truth about yourself. Because we tell ourselves lies and we tell everybody lies about who we are. One of my things that I'm thinking about, I run thought experiments every week, [34:41] A couple of weeks ago, I started thinking about it. I'm still thinking about it, but is what, how wide is the space between your values and your actions? [34:49] You know, if I say like, I'm an honest person, [34:51] Okay, I strive to be honest, but am I truly honest?

So what I'll do is I'll sit down with a piece of paper and say, where have I lied, even if it's small? [35:00] Like, I promised to meet somebody on Friday and I didn't. I said I would send this email and I didn't. [35:05] We tell accidental lies all the time. [35:08] Like that person in the moment, [35:10] intends to send that email, but the person two hours later is not the same person. And so I spend a lot of time thinking about like how [35:20] how to make sure I stay in this place of wonder and curiosity.

And I see people who say, I can't be curious, I can't be optimistic, I can't be filled with wonder, I don't allow myself to be a child, I can't be a child. [35:33] And I would say that's false. [35:35] That's just like a limiting thought. [35:38] And you can change that at any time. It's just it takes a little bit of effort. [35:42] Why do you think people might be afraid to do that? [35:47] People are afraid to show who they really are. [35:50] You know, we're taught. [35:53] from a very young age to have manners and discipline and how society works.

And, you know, you don't want to stand out too much because then you're weird or quirky, especially in places like Japan, you know, like the tallest nail gets hammered down is what they like to say. [36:09] And so there's other cultures in the world where it is not, you're not celebrated for being different, but everyone's different. Everyone is, has unique abilities. Everyone has unique insights. [36:20] And they wear these masks to basically... [36:23] Shield them from that type of vulnerability. And so if you're really silly, you're just like, oh, people are watching me being silly.

But it turns out they're so caught up in their own shit that they don't care. Yeah, like. [36:35] They might just laugh and be like, oh, you know, there they go again. But I think if you were more authentically yourself, you'd ultimately be happier and more curious and more filled with wonder. [36:46] That was like one of the best pieces of advice that I got early on doing this podcast because I'm like kind of quirky. I'm a little bit weird sometimes. And the more I show my personality, the more like people actually started to engage with it.

And I was like, oh, I don't have to be like stiff just asking questions like another like VC interviewer. Like I can make a little funny jokes. Yeah. Like just be you pretending I didn't know Jack and Sam were related ends up becoming like a viral video every month. Right. [37:16] - That's funny. For people, [37:19] I mean, I think, like, change is probably the hardest part and is, like, a biggest... [37:24] limiter, um, uh, or blocker to like be like limiting yourself. Right. Like, so, um, [37:32] What kind of changes do people need to make?

Is it like a daily reminder? Is it like self-manifestations? What kind of... [37:43] Like, what kind of move is that? Is it who you surround yourself with? I prescribe a lot of things. Yeah, I prescribe a lot of things depending on the person. So I do a lot of coaching in this regard, and I've started teaching classes. [37:53] And if you watch my... [37:55] X feed from time to time. I post like openings for awake Academy 101 and [38:03] You know, it depends on where you are in life and where you are with a meditation practice.

And so usually I start people with a meditation practice of five minutes a day. [38:12] Because I say, could you meditate for five minutes a day? And usually they're like, yeah, I could make time for that. And I'm like, well, let's figure out where to fit it in. Usually I recommend if they drive to do it before they start the car. So you go out to the car. [38:27] You sit there for five minutes. [38:29] And you just... [38:30] You don't try to silence your mind. I think a lot of people who think that meditation is I have to have perfect silence and I have to clear all my thoughts.

And I think that actually causes a lot of people to avoid it. [38:41] because they have all of this chatter and noise going on and it confuses them. And then they punish themselves for not being able to shut it down. That's not what meditation is about. Meditation is about noticing the thoughts and noticing that they're going by like clouds and then noticing that you're noticing. So who is that person? So if you are not your thoughts, then who are you is where I would start. And so if people would just spend five minutes a day,

[39:06] just taking stock of the fact that they're in a body, [39:09] And I think that's an important phrase. You are in a body. [39:13] You are not necessarily your body that you can experience the air and what it feels like, the smells that are around you. [39:22] the birds chirping, [39:24] where you are in space. A lot of this we don't think about. But if you spend five minutes a day doing that, you're off to a good start. The next thing is... [39:32] You know, when you take a shower, [39:34] It's a great time to be really, really mindful about washing your body, washing your hair, you know, the water.

[39:41] the ritual of showering. Don't just be in a hurry. Don't just like jump in there and shower every day. You know, make sure that you put that time aside for yourself. [39:51] and really do it right. [39:53] And the other is waking up right, which I'm not I do not have down yet. But waking up right means as soon as you wake up, what's your first thought? [40:01] Usually it's like, oh, [40:03] At first, the first like 30 seconds, you don't think about anything, but then you're like, I got to get up.

[40:08] I got to do this, I got to do that, or I've got to avoid it, I've got to go back to sleep. And you start getting immediately into your routines and that behavioral pattern that you think you can't break. And instead, break it and say, for the first minute of my day, I'm going to feel my toes. [40:24] That's all I'm going to do. [40:26] Just going to sit there and feel my dose. [40:28] And they're there. [40:29] And it sounds silly, but a lot of us forget we even have toes.

And before you even step out of bed, ask yourself, am I awake right now? [40:40] You know, and you may have to write it on your ceiling. I write it on things. [40:44] I leave it in my shower. You know, the mirror, the windows fog up and I write wake up so that when it fogs up and I'm taking a shower, it says wake up. So I leave little reminders, you know, in the fridge. [40:56] all over the place. Because what happens is you start thinking about the future or the past, you start ruminating, and you forget the very, very precious, [41:04] only thing that actually exists, which is right now.

Is that like the number one thing people, like if you coach people and you've done this for a while, like, [41:13] Is that the number one thing people have issue with? Like what do you find as commonality? - Yeah, the number one thing that people have issue with is [41:22] Do you like Rick Rubin? [41:24] Yeah, okay. [41:26] A lot of people have read Rubin and they see his success and they see his demeanor [41:32] And, you know, but they don't know [41:34] how to get there. It's like one of these things where a lot of people struggle with [41:39] There's just so much going on in life.

There's so much on social media. There's... [41:44] There's my family. There's my job. There's my car payments. There's my car. There's my house. All of this is coming at you, and it's part of your left brain. Mm-hmm. [41:54] A lot of us, because we're mind workers, never get into the right brain. [41:57] And the right brain is where creativity resides. It's where your body movements, your [42:02] are it's the intuitive [42:05] sort of nonverbal function. [42:08] of the human existence. And there's a lot of information that you can glean from how you feel.

So eventually, you know, we'll talk about investing and I'll tell you like a lot of my greatest investments came with a feeling. And there's a feeling that you get when [42:24] you know, you're sure about something. There's a feeling you get when you think something's coming and you don't know why. [42:30] And if you could become a master of those feelings, [42:32] you can navigate the world with, with extra sensory perception. I hate to say it, but it's true. Like, like, [42:38] you have more sensory perception of the world than the average person.

And we have a lot of gifts as humans that we don't even realize until we like tap into them and realize, Oh, if I use my ears, I, [42:51] For example, in Mafia, [42:53] to figure out information or if I watch people's eye movements, [42:57] or if I notice [43:00] what's sticking out in a room kind of like where's Waldo? [43:03] I start to notice things that don't belong. [43:06] These are pieces of information that you were never taking in before. And so what happens is if you just do what...

[43:11] you do every day, you're going to get the same results. But if you shake things up, you do things a little differently, you're going to get different results. And so I think that people that come to me that take my class are often they feel stuck. [43:24] They're like, I know I'm on to something. I know that I could do great things. [43:28] But I'm just stuck. [43:30] And so my job is to kind of shock them and get them unstuck. The rest is up to them. I can't fix anything.

[43:36] I can just sort of guide people to the answers because, [43:39] How I got to where I am with a lot of this stuff was – [43:43] a constant questioning. Like, I think human beings are why machines. And so every morning I get up and ask why. [43:50] And I don't usually go about my day until I have a why that I'm thinking about all day long. [43:56] I mean, wow. Yeah. So have you seen, I guess, [44:00] really good place to go from that is into your investments because like [44:05] I would imagine once you start following those threads and asking why a little bit more and having that curiosity, it's very energizing.

Oh, it's really wonderful. Discovering amazing things. So in terms of investments, how has that led you? I mean, you've invested into SpaceX, Uber, Anderle, Flock Safety. I can name like four companies. [44:26] 40 companies maybe right now, but like you've invested in so many companies. How is that and what are some stories? I [44:33] I think I like to talk about Niantic Pokemon Go as one of the whys. [44:38] The first thing I noticed was that these people were playing this game called Ingress. My friends were playing it. I started noticing other people playing it.

But it was a fringe game that not a lot of people were playing. [44:49] But the behaviors that they were displaying, they were renting helicopters. They were chartering boats. They were ditching their friends at DEFCON in Las Vegas to go out into the desert. [45:00] to claim these invisible [45:02] things that didn't exist other than in this app. [45:07] So I started watching it and I was like, that is remarkable. What could get people to do this? And so I started playing it and I started learning about the mechanics and I immersed myself in it.

And then I started asking myself, why is Google doing this? [45:21] So I realized, oh, [45:23] Google ultimately is a mapping company. [45:27] They're gathering points of information. They're getting these players to take pictures of it. [45:31] categorize it, tell them exactly where it is, and to scan that information, it's basically like free mapping data. [45:39] And once I realized that, I was like, this is really clever. [45:43] I wish I could invest in it, but it's Google, so I can't. [45:46] and [45:47] The minute that alphabet spun out, I got all of these messages from my friends and they said, you realize they're spinning out Niantic.

[45:55] And it's going to become its own entity. And I was like, oh, if I ever had a chance to invest in anything, it's right now. Mm-hmm. [46:02] And I don't know how to reach anyone there. [46:05] So I started thinking I I I have a really strange mind where I form associations really, really fast. So, like, I realize it's kind of like a web of thought. [46:16] I was at... [46:19] Hint water. [46:20] which is another investment of mine. And I was helping them set up their ticketing system. And these tickets were coming in that kept saying Ingress code.

[46:28] in the subject line. [46:29] And so I stopped for a moment. I'm like, I don't mean to pry. I'm not really reading your tickets like don't want to invade privacy. Why do these subject lines all say Ingress code? [46:39] And she said, oh, because we work with Niantic at Google on these free game codes in the bottle caps. [46:46] So right when [46:48] Niantic spun out of alphabet, I realized I had to email her. [46:52] It's not obvious. It's like, but that has, that's just paying attention, right? If I wasn't paying attention, right?

[46:58] to what was coming to the inbox of that ticketing system. And how did I even end up there in the first place? [47:03] That's the other miracle, right? And I reached out to Kara Golden and I said... [47:08] Hey, how did you do that biz dev relationship with Google? And she said, I worked with John Hanke, who's the CEO of Niantic. And I said, is there any way you could put me in touch with them? And she's like, yeah, sure. Within five minutes, I'm finally in touch with the head of Niantic.

And I said, I'm in Montana right now, but next week I can come to the office. And he's like, we're not raising any money. We don't need your money. Like we've got Nintendo. We've got Google. Like we don't need you. [47:34] And I was like, please just hear me out. Like, just take an hour of my time and I guarantee you, you will not regret it. And so he let me come in and... [47:44] I brought my best friend who's a player. [47:46] He ended up hiring my best friend pretty much on the spot.

Wow. And realized that I knew a lot of really good engineers and that I had a lot of really good feedback because I'd been playing the game and I wasn't your ordinary investor. Mm hmm. [47:58] And so [48:00] There's an example of how [48:02] Just paying attention and a gut feeling that there's something special here and I'm witnessing it. [48:08] And [48:09] Then I found out about Pokemon. And then I was like, oh, my gosh, you put Pokemon in this world? Like, that's insane. It's going to blow up. Trying to convince people after that, after I invested to co-invest with me, was impossible.

Really? They were like, no one's going to hold their phone up and look at invisible Pokemon. No one's going to go... [48:28] And sure enough, I don't know if you were there the day that Pokemon Go came out. [48:32] I always say it's the closest we've come to world peace. [48:36] It was one of the most magical few weeks of my life. [48:40] and probably many people's lives was when that game came out. And, you know, the same thing with – [48:47] Uber? [48:48] Uber, I started asking why. [48:51] Can I not get a taxi when it rains?

Why are there sometimes I come in at night at the airport and the taxis aren't there? Why is it when I take a taxi from the airport, they drive like a bat out of hell and I think I'm going to dock? Like... [49:03] And what you do is you ask them, you say, hey, what's your life like? Like, what is your day like? And then taxi drivers would tell me, like, well, I wake up. [49:12] I go to the taxi yard. I give them $200. I'm in the whole $200 from the moment I walk in.

[49:18] I drive my car out of the gate. I immediately have to make that $200 back. [49:22] So you imagine that they're rushing around and they're pretty cranky because they're not in the money yet. And then once they're in the money, half their day's already gone. And they're cranky and tired and they're now finally making money. And then they get a customer that stiffs them, a customer that throws up in the car. And you think about their life and you're like, wow, that's miserable. And people complain about Uber, but what they don't understand is what life was like before Uber.

Like they never lived it, so they have no idea. So they just complain about Uber as being this evil entity. But... [49:52] Before that, there wasn't flexible employment. Taxi drivers, you would lose your stuff in it and never get it back. [49:58] You were in the hole $200. [50:00] There was a lot of things that were broken about that. [50:04] Uber arrived and I found out about it. [50:07] I'd already done the pre-thinking. [50:08] So when you ask why about everything in the world, it's just going to make you a better investor.

It's going to make you a better entrepreneur, a better everything. [50:16] You know, when you're sitting around idle at a restaurant, [50:19] Don't just sit there and like, [50:21] Stare. [50:22] or doom scroll, ask yourself, [50:25] Why do they bake bread at Tartine that way? [50:29] are they using that device? You know, would robotics improve any of this or not? You know, and just really ask yourself questions about where the world is going to go. [50:40] especially if it's like a science fiction sort of scenario and just, [50:44] play with it and make believe and it'll lead you to these amazing outcomes.

Do you find it [50:50] Interesting that a lot of things that happen in sci-fi movies become real. [50:55] It's almost prophetic. [50:57] It's very, very strange. Like her is becoming a thing. [51:01] There's so many science fiction movies that have have turned into reality. Let's just hope that Terminator isn't one of them. You don't want that reality. People really like to bring up Skynet all the time. Yes, because it's an unfortunate possible reality. One of the things I like to ask people is what worries you? Peter used to ask me that at Founders Fund.

[51:22] And it's a very important question because it's what excites you is interesting, but what worries you is also interesting. [51:28] And I am worried about