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Host
Congrats on SpaceX.
Cyan Banister
Thank you. That was my first check. Luke came over to our house and he's like banisters. 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 you is also interesting. If you get invited to a Peter Thiel event, go. Do not shy away from it. It does not make anything that anyone's going to accuse you of. You don't eat babies.
Host
SpaceX, Anduril, Uber, Zappos, PayPal, affirm Flexport checker Density Block Safety.
Co-host
That's a really cool company.
Host
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. Calm True Med and Crusoe. So what's your favorite foreign. So we are at Long Journeys hq. It's called the Boobies Place. The Bubbies place.
Cyan Banister
Bubbies. Bubby's place. Yes, Bubby might have some boobies, but it's Bubba's Place.
Host
And we're in a very special room right now. They call it Cyan Bannister, the star. One of the stars. Because I also called Dylan the star of Mafia. You're all stars of Mafia in your home? Yep.
Cyan Banister
Well, we are in Long Journey's headquarters. And this room that we're in right now, they call it Cyan's Lair.
Host
Oh.
Cyan Banister
I have a tendency wherever I'm at, including at Founders Fund, I was behind the bookshelf that turns out, uh, I really like darkness and artificial light is not my friend. So.
Host
Oh, my God.
Cyan Banister
I. I'm 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.
Host
So tell us. I mean, if you're not looking, you should watch the video. If you're not listening. If you're listening on Spotify, look at the video. Right now we're in this crazy, like, very beautiful, charismatic room with lots of fun imagery. So could you just explain what's going on behind us. It's also entirely around all the walls down here in the lower level, everything's covered. What is this?
Cyan Banister
So this is done by an artist named Dave Zakin, who lives in Brooklyn. And I discovered him on Instagram. 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, that was one of the things I had to do. And so I recognized and 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.
Host
Oh, wow.
Cyan Banister
And so his friends started bringing him pieces that he could paint in bed and, you know, ways of making an income. 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. 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 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. 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 re glazes it, basically puts it fires it again and gives it a new life. And so I collect a lot of his art, a lot of his cups. I have around my house, and they all have a sense of humor. Sometimes it's a commentary on the world. But I'm a big fan.
Host
There's so much going on right now. Yes. Yes. In case you didn't know that. Yeah.
Cyan Banister
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 bucks for, I think, both of them.
Host
What?
Cyan Banister
Yeah. And so I love walking around town with them.
Host
Oh, my God.
Cyan Banister
It just brings a lot of joy to people.
Host
Is Dave also the ceramicist of the camera?
Cyan Banister
No. I need to find the woman's name that made these things so that I can promote her work. I have not met her in person yet, 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.
Host
This is so fun. I just can't imagine what your house looks like if this is your office.
Cyan Banister
Yeah, it's different. It's a different kind of crazy. It's different. I like to mix it up. It's not quite like this, but. But I look like if you were to go to Goodwill for your design. I know that sounds weird.
Host
What?
Cyan Banister
Yeah, it's more thrift store oriented, and everything's vintage and everything's odd. I tend to, like, if people come to my house, I gauge my success rate by how many things do they touch without my permission?
Host
Oh, interesting.
Cyan Banister
Yeah. So what happens when you see something and you. It sparks like your inner child. You start just rummaging through 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. Cause I want it. I actually want people to rifle through things and feel so at home that they can play. And so 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, this is a silly place. I'm free to be silly.
Host
Is that the most touched thing? That's what people are.
Cyan Banister
Yeah. The fish, the fake snowballs, people. I mean, that's obvious. Like, it's like, oh, they're snowballs. Let's throw them. There's also, like, weird collections of fried eggs. Cause I don't like eggs, but I like the way fried eggs look. So I have, like, a wall of fried eggs. And just people laugh when they see it. So that's the other thing is if they laugh and chuckle, I know I've done my job, you know. So in general, if you were to come to my house, I want you to play.
Host
And you don't like candles. Right. So there's two candles on the wall. What do those represent?
Cyan Banister
I hate candles.
Host
Yeah.
Cyan Banister
Because my mom accidentally burned down her house when she was younger with a candle and I heard about it growing up and so I had this fear of candles. So I've never liked them. 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 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, they can come back and get their flame back.
Host
Oh, wow.
Cyan Banister
And so 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.
Host
That's. Yeah, that's good.
Cyan Banister
Yeah.
Host
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 a Long Journey logo mean?
Cyan Banister
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 is, by the way, it says it's called evil eye, but it's actually a good omen or supposed to look 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. And people say, well, why is she. Being a sheep is bad. Is being a sheep bad? You know, it's.
Host
I really like bad.
Cyan Banister
Bad is bad. 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, something is better than nothing. What if nothing is better than something? In many cases, nothing is way better than something. So I thought about don't be a sheep. And so I was like, well, when is being a sheep a good thing? And how are sheep led? 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 if you think about it, you're outsourcing your trust to someone else. And if you think about Apple, we all use the iPhone. Does that make us sheep, 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 being comfortable following a leader. 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 if you want the bellwether looking off to the side to see what's coming and to see what's non obvious. And so it's kind of a play on this concept of don't just take a sentence at face value and not play around with it and play around with the concept and see if it holds true. But that's where it comes from and its name is Bellwether.
Host
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 was also involved?
Cyan Banister
Yeah. So Mafia is a role playing game that's super simple to play. You can play it without any cards or anything. Mike happens to use an ordinary deck of cards and you get assigned a role that you're either a townsperson, villager, you're a mafia member, you're a sheriff, or you're an angel. And angels can wake up in the night. You all go to sleep at night, 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 can see who is mafia and who isn't during the night. And then the mafia kills a villager or 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. At first you just have to kill somebody and you have to coalesce on who to kill. And then afterwards, it's a game of deception and lying 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. 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, who they seem to be bonding with, who they seem to be forming an alliance against. All of that is a tell and information, because you have to assume that they're all lying. If you're going in with imperfect information, you have to figure out what your strategy is. And if you watch the show, you'll see that everybody kind of has their own strategy. And when I first got there, 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, I played with Dylan, and Dylan's really good. I kept hearing from multiple people that Dylan is really, really good. So I was like, well, Dylan's gotta go. If I am mafia, Dylan's gone. And I was like, who else? And they said, moxie. So Moxie.
Host
Moxie got a lot of hate.
Cyan Banister
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 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.
Host
Oh, my gosh.
Cyan Banister
Like, I mean, Trey's a badass, but, like, I just didn't realize, like, that he would take us all the way home, you know, that was no easy feat.
Host
Yeah. So you mentioned, like, I think it was the beginning of the last game. Like, if people listened to you, you guys would have won.
Cyan Banister
We would have won. We would have won. They would have taken out Sam and Ryan and, you know, eventually figured out that Palmer, 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 Palmer to the left, and then I had Brian, and Dylan were all mafia. And they basically, what happened was they were all leaning on the table, and when they got up to kill the whole table, just, like, jerks. 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 when they woke up in the night to kill. And I was like, it's gotta be. If I'd stayed in the game, I would have gone after Sam. So I'm surprised that they didn't use the intel, but maybe they just didn't.
Host
And they killed you then after that, or the town? Yeah, of course they killed me.
Cyan Banister
Yeah.
Host
You knew too much.
Cyan Banister
Too quiet. Apparently, if you're too quiet and you're observant, it gets you in trouble. They automatically assume you're in trouble.
Host
What do you think the best strategy is through all of it?
Cyan Banister
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. Cause 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. But for me, I mean, 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. 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, you know, a few times.
Host
Well, you've now been outed.
Cyan Banister
I've been outed now, yeah.
Host
There's millions of views on that one.
Cyan Banister
Yeah, I've been outed now, but that was my first time being Mafia or Wolf. I have never been a killer before. I never had to lie like that. And so I gotta say, that was challenging. Really super challenging for me to lie. I do not like it. And it made me very uncomfortable. And I thought you could absolutely tell, But Dylan was just like, I couldn't tell. You're just very hard to read.
Host
Yeah.
Cyan Banister
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. I think it would be fun to see some different people in our industry go in and have some of them come back.
Host
Yeah.
Cyan Banister
You know, because I do think there was some really good players in there that should return.
Host
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 have an understand. 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, be on the inside and, like, kind of see how everyone's dynamics are. And it did look like not everyone knew each other either. So it was like a cool kind of like, just like, yeah, some of
Cyan Banister
us know each other well and some don't. And so for me, even it was really interesting. Like, I've maybe talked to Brian Johnson a couple of times over, like, DMs talking about health stuff, but, like, I've never actually spent that much time with him, so it was really fascinating to see what he's like in person. And then I love Moxie and 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, which is where the famous PayPal mafia photo is.
Host
Really?
Cyan Banister
Yeah. So it's the. I didn't know that. Yeah. So the exact same picture. If you look at it and then you look at where we're playing Mafia, that's what makes it so funny.
Host
No way. Oh, my God.
Cyan Banister
Yeah, so it'd be super cool if you got some of those folks on.
Host
Yeah.
Cyan Banister
You guys, I would love to see Rabboy and. And, you know Peter. Yeah, that would be so cool. That'd be so cool.
Host
So cool.
Cyan Banister
I don't know if Peter would do it, but who knows? You never know.
Host
Yeah. Hopefully it's funny. Like, I've interviewed a handful of the PayPal mafia at this point, and I keep on asking each one of them if there's a group chat. They keep in touch and they're like, nope. Like, some of us do not talk to each other anymore.
Cyan Banister
Yeah, some of them don't, but some of them are ride or dies. Right. Like, there's always been this sort of. This unspoken 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 at the drop of a hat, they're like family to me, and I would just rise and go 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, it's kind of like a mafia, because they really, really help each other out.
Host
I feel like Elon would go.
Cyan Banister
I think he would.
Host
So was there anything that was recorded that wasn't kept in, like, are there any dynamics we didn't get to see?
Cyan Banister
I would imagine. Yeah. I don't. I don't know if I'm allowed to say, because it might get me intrig probably. But, yeah, there was some really spicy moments between a few of the people, and they got cut. So maybe someday Solana can do, like, an outtake of some of these things.
Host
Quick blooper reel.
Cyan Banister
Quick blooper reel. Well, there's a lot of things that were back in the sushi room, you know, because keep in mind that the cameras were rolling from the moment the game starts, 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.
Host
Oh, my God.
Cyan Banister
And just really funny comments inside comments, you know, some fun stuff, which I won't get into with Palmer and Sam Altman. They're friendly. It wasn't that. It was just, you know, just banter that you wouldn't imagine. You're just like, wow, I'm sitting in this room and this is happening.
Co-host
Yeah.
Host
Crazy.
Cyan Banister
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.
Host
Yeah.
Cyan Banister
So maybe they'll do, like, a blooper reel or something like that someday.
Host
It'd be fun. I'm excited. Hopefully, Solana, you make a season two.
Cyan Banister
Oh, I hope so.
Host
I would hope so.
Cyan Banister
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.
Host
No, really.
Cyan Banister
And so we were sworn to secrecy. We couldn't tell anybod anything. I didn't even tell my partners here about it.
Host
What?
Cyan Banister
And. And I actually was really proud of not telling anybody because the. The whole firm got to be surprised by it. Like, just on a random Wednesday afternoon, they were, like, texting me. They're like, what? I'm like, surprise. I just knew you would love it. So. Yeah.
Host
So why did he wait so long to release it?
Cyan Banister
Editing.
Host
Really?
Cyan Banister
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?
Host
Yeah.
Cyan Banister
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, there's aerial cameras. There's cameras on the table. So on the table there was this round thing that each. There was a lens at each one of us.
Host
Ye.
Cyan Banister
So like a poker game, you know, and if you see, like, the different reactions where they can. Like, that was not like, a camera person. So that part, I think, was probably challenging to put that all together. I can only imagine just how much thought and preparation. It looks effortless.
Host
Yeah.
Cyan Banister
But it was not. I mean, if you saw the set and you saw how many people were involved, there was, like, probably over 30 people just on the camera production side for that.
Co-host
Wow.
Cyan Banister
Yeah. It looks simple, but it was definitely not simple. It would be very hard to produce that show, let's put it that way.
Host
Yeah.
Cyan Banister
So Mike thought about it for years, you know, years and years and years, like, how. And many people have attempted to make this show. This is not the first time, you know, Chris Sacca and a couple of other people tried to make it with Werewolf. And I ultimately could not figure out the right way to display it on television. And, you know, Mike's a genius, so he figured it out.
Host
Yeah. Danielle Strachman. We didn't interview, like, early teal fellowship days, probably like a year ago. And now with 15, 17, like, it's really cool to see how everything's been going. But she said, like, early days, I 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 like confessionals. Ooh, you're missing the confessionals.
Cyan Banister
Confessionals, yeah. That would be great. Ah, we should add that. Yeah. I've made a lot of friends playing mafia and Werewolf. I have found some founders through it. If you think about it, it's kind of like poker or golf. 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 without, like, all the small talk, you know, so you can just, like, dive in, do something together, get to know how somebody operates and how they work, you know, or lie. You can learn how they lie or don't lie. Yeah, it's a really interesting thing. And maybe it's more popular among us because we're not, you know, we're neurodiverse here. And so maybe it's fun for a lot of us to try to figure out how people are presenting and the masks that they wear.
Host
Yeah. Yeah, that is really fun. I recently had Brian Singerman on, who gave you a really great shout out.
Cyan Banister
Love, Brian.
Host
Yeah, he's awesome. I have 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.
Cyan Banister
He got me into board games.
Host
Really?
Cyan Banister
Yeah, he did. We used to have a board game club, A board Game of the Month club that he. He subscribed to it. I had all my friends subscribe to it. Board Game of the Month club. And they would pay me $40 a month.
Host
$40 a month.
Cyan Banister
And then what I would do.
Host
Diane, what are you doing?
Cyan Banister
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, 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. And so Splendor ended up being one of our favorite games, Machikoro. 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 just to get the little pieces out. And the little.
Host
Like, oh, my God.
Cyan Banister
All this crap that you have to do, like, it takes a long time. But he is a champion at that like when it comes to strategy board games. I have never met anyone better than Bryan Singerman.
Host
Really?
Cyan Banister
Yeah, he's the best.
Co-host
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Host
R Y 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 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 community.
Cyan Banister
Well, I think again, going back to neurodivergence, I think 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 what have you been thinking about and what excites you? 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, but you're doing something. And the same thing with strategy games is you can kind of see how somebody plays A game, and you can see, like, what their skill level is. Like, 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, like, the psychology around it? Like, what level are they playing at? Is something you can gauge in these games. And so I think that's why they're so popular. 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. I think Reid Hoffman, for a long time did Settlers of Catan game nights, and people would go play them. There's people who have more casual games, like I used to do, that are 30 minutes or less, because I wanted people to be able to play a couple games, socialize with people, and then bounce because they're busy and. And also just not spend many, many hours trying to figure out how to play the game. So it just really depends. But I think it. It's a great reflection of their inner world.
Host
You're also a prolific poker player. I've seen some videos.
Cyan Banister
Yeah, I am. I. That's really funny, because I don't really play a lot of poker, but I'm known for it, which is weird, right? And part of it is because I host a charity poker tournament 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.
Host
Really.
Cyan Banister
I'm really not that good. I probably could be better if I tried, but there was a poker tournament sort of thing that I fell into kind of on accident, and I ended up at this table playing with Steve Aoki Ninja Phil Hellmuth. And I ended up beating Phil Hellmuth, which was legendary. And part of it was I was playing very, very conservatively because, 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 till the commercial break or whatever the break was. We went to this break and they were like, hey, just so you know, everybody can see your cards. And I was like, wait, what? 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?
Host
Oh, my God.
Cyan Banister
And so this guy comes up and he's like, what would happen if you bluffed once? Just once, like, do you bluff? And I was like, no, I don't bluff. And he's like, just one time. So I came back and I waited for a hand in which the pot was large enough, 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. 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 12 cards you could have. And he's like, do you have them? Which means he doesn't have them. Right.
Host
So.
Cyan Banister
So he's on tilt. And he's like, so finally he folds, 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. It was so good.
Host
How do you find yourself in these situations?
Cyan Banister
That's kind of my life. My life is a series of these types of event. Even before 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. I walk off ledges expecting everything's going to be fine. Not literal ledges, but you know what I mean?
Host
Yeah.
Cyan Banister
And I do honestly believe that everything's going to work out. 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 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.
Host
Really?
Cyan Banister
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, 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. 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?
Host
No.
Cyan Banister
It's with Bill Murray. It's fantastic. Basically, without giving it completely away, he thinks he's in a game, like a role playing game where people are doing things for him, but he's actually really running with, like, criminals. And he has no idea. But that's my life. Not that I'm running with criminals, but like. Like my life is sort of a show of sorts, like a Truman Show. And I'll show up and weird things happen. And I'm like, wow, that's. That's happening. That's really neat. That's interesting. And I just kind of roll with it.
Host
What has that taught you about human behavior, though? Because most people don't live like you. They're not as optimistic
Cyan Banister
they could be.
Host
How can they be?
Cyan Banister
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 lot of time being introspective. And I would say that he's wrong, and I'd love to have a chat with him about this. You can actually surgically go in and alter your personality 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. A couple weeks ago, I started thinking about it. I'm still thinking about it. But is how wide is the space between your values and your actions? If I say I'm an honest person, I strive to be honest, but am I truly honest? 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. Like, I promised to meet somebody on Friday, and I didn't. I said I would send this email, and I didn't. We tell accidental lies all the time. Like, we. That person in the moment 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. How to make sure I stay in this place of wonder and curiosity. And I. I see people who say, I can't be curious. I can't be optimistic. I can't be. Be filled with wonder. I don't allow myself to be a child. I can't be a child. And I would say that's false. That's just, like, a limiting thought. And you can change that at any time. It just takes a little bit of effort.
Host
Why do you think people might be
Cyan Banister
afraid to do that? People are afraid to show who they really are. We're taught 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. 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 has unique abilities, everyone has unique insights, and they wear these masks to basically 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.
Host
Yeah.
Cyan Banister
Like, 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.
Host
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 people actually started to engage with it. And I was like, oh, so I don't have to be, like, stiff? Just asking questions, like another, like, VC interviewer. Like, nope, I can make little funny jokes.
Cyan Banister
Yep.
Host
Just be you. Pretending I didn't know Jack and Sam were related ends up becoming, like, a viral video every month.
Cyan Banister
Right.
Host
Which is really funny for people. Like, I mean, I Think, like, change is probably the hardest part and is like a biggest limiter or blocker to like, be like, limiting yourself, right? Like, so what kind of like, changes do people need to make? Is it like a daily, like, reminder? Is it like self manifestations? Like, what kind of, like, what kind of move is that? Is it?
Cyan Banister
I prescribe yourself 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. And if you watch my ex feed from time to time I post, like, openings for Awake Academy 101. And 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 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, you sit there for five minutes, and you just. 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 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 just taking stock of the fact that they're in a body, and I think that's an important phrase. You are in a body. You are not necessarily your body that you can experience the air and what it feels like, the smells that are around you, the birds chirping, 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 when you take a shower is a great time to be really, really mindful about washing your body, washing your hair, the water, the ritual of showering. Don't just be in a hurry. Don't just like, jump in there and shower every day. Make sure that you Put that time aside for yourself and really do it right. And the other is waking up right, which I do not have down yet. But waking up right means as soon as you wake up, what's your first thought? Usually it's like, oh, at first. The first, like 30 seconds you don't think about anything. But then you're like, I gotta get up, I gotta do this, I gotta do that, or I've gotta avoid it, I've gotta 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. That's all I'm going to do, just going to sit there and feel my toes. And they're there. 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? You know, and you may have to write it on your ceiling. I write it on things. I leave it in my shower. You know, the mirror or 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, 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 only thing that actually exists, which is right now, is that like
Host
the number one thing people like, if you coach people and you've done this for a while, is that the number one thing people have issue with? Like what do you find as commonality?
Cyan Banister
Yeah, the number one thing that people have issue with is. Do you like Rick Rubin?
Host
Yeah.
Cyan Banister
Okay, so a lot of people have read Rick Rubin and they, they see his success and they see his demeanor and, you know, but they don't know how to get there. It's like one of these things where a lot of people struggle with. There's just so much going on in life. There's so much on social media. There's war, 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. A lot of us, because we're mind workers, never get into the right brain. And the right brain is where creativity resides. It's where your body movements are. It's the intuitive sort of non verbal function of the human existence. And there's a lot of information that you can glean from how you feel. So eventually 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 you're sure about something. There's a feeling you get when you think something's coming and you don't know why. And if you could become a master of those feelings, you can navigate the world with extra sensory perception. I hate to say it, but it's true. Like, 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, for example, in mafia to figure out information, or if I watch people's eye movements or if I notice what's sticking out in a room, kind of like Where's Waldo? I start to notice things that don't belong. These are pieces of information that you were never taking in before. And so what happens is if you just do what 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. They're like, I know I'm onto something. I know that I could do great things, but I'm just stuck. 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. I can just sort of guide people to the answers. Because how I got to where I am with a lot of this stuff was a constant questioning. Like, I think human beings are why machines? And so every morning I get up and ask why. And I don't usually go about my day until I have a why that I'm thinking about all day long.
Host
I mean, wow. Yeah. So have you seen, I guess a really good place to go from that is into your investments. Because like, 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, Anduril, Flock Safety. I can name like 40 companies maybe right now. But like, you've invested in so many companies. How is that? And what are some stories I think
Cyan Banister
I like to talk about Niantic Pokemon Go as one of the whys. So 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. But the behaviors that they were displaying, they were renting helicopters, they were chartering boats, they were ditching their friends at DEF CON in Las Vegas to go out into the desert to claim these invisible things that didn't exist other than in this app. 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? So I realized, oh, Google ultimately is a mapping company. They're gathering points of information. They're getting these players to take pictures of it, categorize it, tell them exactly where it is, and to scan that information. It's basically like free mapping data. And once I realized that, I was like, this is really clever. I wish I could invest in it, but it's Google, so I can't. And 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 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. And I don't know how to reach anyone there. So I started thinking, I have a really strange mind where I form associations really, really fast. So I realize it's kind of like a web of thought. I was at Hintwater, 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 in the subject line. I stopped for a moment and I'm like, I don't mean to pry. I'm not really reading your tickets. Don't want to invade privacy, but why do these subject lines all say ingress code? And she said, oh, because we work with Niantic at Google on these free game codes and the bottle caps. So right when Niantic spun out of Alphabet, I realized I had to email her. It's non obvious. It's like, but that's just paying attention, right? If I wasn't paying attention to what was coming to the inbox of that ticketing system and how did I even end up there in the first place? That's the other miracle, right? And I reached out to Kara golden and I said, 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. 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 I brought my best friend, who's a player. He ended up hiring my best friend pretty much on the spot.
Host
Wow.
Cyan Banister
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. And so there's an example of how just paying attention and a gut feeling that there's something special here and I'm witnessing it. And 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 gonna blow up. Trying to convince people after that, after I invested, to co invest with me was impossible.
Host
Really.
Cyan Banister
They were like, no one's gonna hold their phone up and look at invisible Pokemon. No one's gonna go. And sure enough, I don't know if you were there the day that Pokemon Go came out. I always say it's the closest we've come to world peace. It was one of the most magical few weeks of my life, and probably many people's lives, was when that game came out. And the same thing with Uber. Uber. I started asking why? Why 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 a bat out of hell? And I think I'm gonna die. And what you do is, you ask them, you say, hey, what's your life like? What is your day like? And the taxi drivers would tell me, well, I wake up, I go to the taxi yard, I give them $200. I'm in the whole $200 from the moment I walk in, I drive my car out of the gate. I immediately have to make that $200 back. 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. Yeah, like they never lived it, so they have no idea. So they just complain about Uber as being this evil entity. But, you know, before that there wasn't flexible employment, taxi drivers. You would lose your stuff in it and never get it back. You were in the hole $200. There was a lot of things that were broken about that. So when Uber arrived and I found out about it, I'd already done the pre thinking. 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. You know, when you're sitting around idle at a restaurant, don't just sit there and like stare or doom scroll. Like, ask yourself, like, why do they bake bread at Tartine that way? Like, why 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, especially if it's like a science fiction sort of scenario. And just play with it and make believe and it'll lead you to these amazing outcomes.
Host
Do you find it interesting that a lot of things that happen in sci fi movies become real?
Cyan Banister
Yeah, it's almost prophetic. It's very, very strange. Like her is becoming a thing. There's so many science fiction movies that have have turned into reality. Let's just hope that Terminator isn't one of them. We don't want that reality.
Host
People really like to bring up Skynet all the time.
Cyan Banister
Yes, because it's an unfortunate possible reality. If 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 you is also interesting. I am worried about us moving more and more into a surveillance state that is operated by AI and there's robotics. If you have a leader that you trust, maybe it's not a big deal, or you have a government that you think is kind of operating, maybe not a big deal. But if you have a totalitarian state or you have, you know, you're in a country that isn't America, it starts to get kind of weird. Yeah, you know it. Right now we're moving towards a future where you won't be able to get into a car and drive yourself somewhere. And if you think about it, that freedom of movement is a human right. What if someone says, you know what? You're just not going anywhere. I'm just going to shut your Waymo down. And not only that, but I'm going to lock you inside because you're a dissident, because you're saying things we don't like. There's an underbelly to all of this. There's a utopian future and a dystopian future. And it's kind of like a gun can be a paperweight or a weapon. AI is the same. And so we really have to think about how to be responsible and how to. I'm all about acceleration, but I'm also about thinking through should any of this fall into the wrong hands, how could it be used? That's why I tend to back things that are open source and decentralized control. Because I think that the Internet started out, and I'm old enough now that I got into this industry in 1999, that we originally started out for this whole ecosystem to be mostly open source and decentralized. But it went the opposite direction. It became incredibly centralized and closed source. And you're seeing that happen with OpenAI and Anthropic. It's the wrong path because everyone needs to have their own models. Everyone needs to be able to be able to compete. And you don't want one company with one ideology ruling it all. That's dangerous.
Host
Wow. Damn.
Cyan Banister
Yeah, sorry.
Host
That is a worry.
Cyan Banister
It is a worry. It worries me. It's what keeps me up at night. I think about that and I think about children. I think about people wondering, like, what are they going to do if a lot of this stuff becomes automated? Like, what is the future? What should they be studying right now? It's unclear. It's really, really unclear. I almost want. If you're not getting into medicine or like a hard thing that requires four to six years of school, I'm not sure people should be going to school right now.
Host
Really?
Cyan Banister
Yeah, I don't think so.
Host
What should they be doing.
Cyan Banister
I think artisanship is going to be on the rise, being creative. So the one thing I have not seen AI be capable of. So let's talk about what I'm excited about.
Host
Okay.
Cyan Banister
I'm really excited about AI being a new paintbrush and a new tool to unlock all the creativity in this world that has been dormant. So there's a lot of people out there with a million dollar idea that want to go on Shark Tank and they can't. But what if they could vibe manufacture? What if they could vibe code the app, which they can now, and put up a website and create a product that the market has never seen that actually improves lives? I think we're going to see a lot of maybe not venture scalable businesses, but a lot of newly minted millionaires that are going to figure out how this all works and they're going to set up a completely agenticized business where there's no real employees. That's going to happen and they're going to do it from their basement. And I'm really excited about that future. I'm not scared of it. And I think that the other thing is I'm really excited about art. So right now I know it's very controversial. A lot of the models were trained on art and basically stole art for training data. Eventually, after 100 years, all art becomes part of public domain. You can train on it anyway. So it's kind of like if not now, it's going to happen and then what's really going to happen is China will sell our art back to us. So they're going to steal it all anyway because they don't care. And they're just going to basically come back to us with these models, which we've seen with deep seq and everything else that's trained on our, our ip, and then they're going to sell it back to us. So we're going to be buy. It's going to be kind of hilarious that we're going to be buying South Park Remixed. That's completely not, you know, approved from probably pirate operators from China. But what these tools will do is now I can be a filmmaker. Like there are hundreds of movies inside of me and I couldn't, you know, get a team of camera people and editors and all this stuff to make that happen. But now I can make it happen. And of course there's a bunch of people who say it's slop, it's not good. But where this is right now, we're in a period where it's the worst it'll ever be. It's going to be to the point later in the future where you're going to be able to scan yourself and make 100 different versions of your show, you know, in different languages and all sorts of stuff. You couldn't do that before. And you're going to be able to reach people in ways that you never even dreamed of in the future. And so I'm really excited about that. I think it's going to be really, really neat.
Host
I mean, that is so. It's like very. It's very top of mind right now. I mean, we just came off of config and so we were talking to a lot of designers, a lot of artists talked to Dylan Field, like, and I asked a lot of them, like, what's your hottest take on AI right now? Like, what are you most worried about? Also, like, what's the worst design ever? Someone said shower head. I thought that was really funny. But with AI, a lot of the kind of, like, where it's centered back to is that AI just helps create the average. And then it is up to the human, the person, to take the risk and pull it out of the bell curve and like, make it exceptional and very cool. And like, that is something that it has not been able to do yet. And another through line that like. And these are all just completely different people. Like, we talked to a professor of the MIT Media Lab, we talked to designer of Human Robotic Interface at Boston Dynamics, talked to the product head of product design at OpenAI, Dylan Field and Nico over there. And a lot of them, they're just like, like you. It kind of came down to you have to be an active player. So that's why with the school thing, it's like, I. I don't really know because maybe some of the schools, like, aren't letting you get be an active
Cyan Banister
player, because they are.
Host
It really comes down to, like, thinking, like a lot of the thing. Like, a lot of the points were down to thinking. And I joked with Zach Lieberman, who is a professor at MIT Media Lab. I'm like, instead, you know, like, there was a campaign once that was think different. Now we just need to drop different
Cyan Banister
and just go with think. Exactly. I think you're absolutely right. There's so much that AI cannot do. And for example, if you try to write a book with AI, you'll start to notice, which I am doing, you'll start to notice phrases and the way it does things are the telltale signs that it's AI. Anyone who's used enough of it or read enough of it, knows the signs, but however, it has these nuggets that maybe you didn't think about and you're like, oh, I could do it that way. And your job is to massage it back into a human form. So it takes a lot of the heavy lifting off, but it's not a complete replacement for any human. And so I have friends who wrote scientific papers and used AI for it. And of course people could tell, they're like, you used AI for this, didn't you? And it doesn't matter that it's accurate and it's conveying exactly what they wanted to say. You're still going to have people who are going to be dismissive of it no matter what because they're going to like it's hallucinating it, it clearly can't be trusted, et cetera. So I don't think people should be that afraid. But at the same time, a lot of skills that we go to school for you can now learn. I learned so much just using ChatGPT and Grok. I'll just say I want to learn about this philosopher, set me up a lesson and then I can interrogate this bot that's talking to me. I can walk around and have it in my ears and just listen. You know, a lot of that you don't even need to go to school for anymore. Yeah, you can be self taught. It's actually possible now.
Host
It's so interesting. I know we got very well into the conversation and we haven't really talked about investments that much. But I think like with long journey and your background, you guys love the magically weird.
Cyan Banister
Yes.
Host
And you do follow your curiosity and it's also, it comes off very effortlessly with your track record which you cyan are savage. I don't know if you know that you're low key savage.
Cyan Banister
Thank you.
Host
And it's really, I mean, I think it's hilarious every time these like angel reports come out, they're obviously using the same graph over and over again. But like you probably are and especially with Scott too, like the number one on the list.
Cyan Banister
I think the two of us combined are definitely number one in the world.
Co-host
Yeah.
Cyan Banister
And it's, it is frustrating. But I also understand and have sympathy for the fact that we are a team and a duo and that doesn't fit nicely into boxes, you know, it's kind of difficult to figure out, you know. And the other thing is a lot of people don't realize that married people share capital. Like everything that's mine is his, and everything that's his is mine. And we've been partners since we started investing together, which is over 20 years now. And so some deals, obviously he sourced, some that I sourced. And so it's very difficult to figure it out. But even when we break it down and we divvy it up between the two of us, we're still in the top of that Stanford list. For example, we would both be in the top 10. But combined together, we're number one. And so it's just whether or not they're willing to combine us together. TechCrunch gave us the angel of the Year award, and they originally were only going to let me accept it. And I said, I don't want to go on stage and accept an award that my husband also deserves. And so it's kind of like we're left and right brain, and we're one human. And so I understand that does not fit into people's nice, clean, you know, however the world is supposed to look.
Co-host
Damn.
Cyan Banister
But we're really good because we're a great team.
Host
Well, I'm gonna name some of those.
Cyan Banister
Okay.
Host
You put it in a list.
Co-host
So I'm gonna name all of them.
Host
Oh, okay. All right, buckle up. We have SpaceX and Oral. By the way, congrats on SpaceX.
Cyan Banister
Thank you.
Co-host
Big.
Cyan Banister
That's my first check.
Host
Do you get anything cool with that? Are you still in lockup?
Cyan Banister
Probably still in lockup.
Host
Okay, so SpaceX, Andrew 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 5 Tran Forge, open door.
Co-host
Very.
Host
Had a lot of fun with Kaz. We did a really fun, like, recent interview there. Calm, True Med and Crusoe.
Cyan Banister
Yeah.
Host
So what's your favorite?
Cyan Banister
You can't. It's like children. You can't pick your favorite. I mean, they're CEOs. And that group of people that I have loved working with closely, you know, John Hanke, who I mentioned before, is definitely one of my favorite CEOs I've ever had the opportunity to work with. How he sees the world and how he manages people from sort of behind and not in front is. And he's very humble. I like seeing people's different leadership styles, and they're so wildly different. And then it's really such a joy to see a company grow up. You know, you. You Start out in a space kind of like this, where there's a couple of people and an idea and then the next thing you know, like you're touring Anduril and you know, it's like, whoa, there's thousands of people here. It's like really grown up. And so that process, you know, I always take pictures of billboards because I call it seeing my investments in the wild. And it just gives me such delight to see any evidence of an investment that makes it further than the garage. You know, I'm just like, oh, wow, look there, they're on the side of a building. Oh look, the products on the shelf in the store. And you know, like, I invested in Cafe X, which has these coffee shops at the airport that serve robotic coffee. Very fun and very fond of them. But they need disco balls. That's my gripe. My biggest complaint is I need some disco balls in there. I keep sending it to the founder, but when I see that, I just, I get tickled that I'm even a small part of the change in the world, you know, that I'm making my own little butterfly effect every time that I do one of these.
Host
How did you get into SpaceX?
Cyan Banister
Ah, how did I get into SpaceX? Luke Nosek. So if you haven't interviewed him, you should put him on your list because he's really cool. So Luke is part of the PayPal mafia. He's the co founder of Founders Fund, the co creator and inventor of PayPal. And he went to college with my husband, Scott Bannister and Max Levchin, and they met in a computer lab back at University of Illinois. Interestingly, Max had to stay because his parents said you can't drop out, you have to get a degree before you go to Silicon Valley. So Scott and Luke basically came out west together and they had walkie talkies because there was no cell phones at the time. I've got a fun picture of this, by the way. And eventually Scott started a company called Submit it, which sold to Link Exchange, which got bought by Microsoft. And he ended up working with Bill Gross and going kind of on his own path. But he was one of the first investors in PayPal and was on the board. And then of course Max came, ended up starting PayPal, teamed up with Luke, and then eventually Peter came on board. And then the Elon part also happened. And so Luke, you know, formed a relationship with Elon and I would say probably was his strongest second believer. You know, I've never seen anyone champion a company or a person with more heart than Luke. And so I didn't know Elon and Scott kind of barely even overlapped with Elon at PayPal, so there was no connectivity there. A lot of people, the number one thing they asked me is what's it like to be Elon? And I'm like, well, I only see him at weddings.
Host
Really?
Cyan Banister
Yeah, like he's like a wedding guy. You know those people that you only see at funerals and weddings? Well, Elon's that guy for me.
Host
Oh, my God.
Cyan Banister
Yeah. So when my friends get married, he's there. And. Which is amazing that he makes the time, by the way, that he actually like, like, oh, if we should probably stop for a second because there's a clock going off anyway, there's, it's amazing that he makes the time and actually shows up to these weddings. But what got me to invest in it was Luke came over to our house and he pretty much, he's a very emphatic person and he wears like these Vibram shoes and you know, he gets on the floor and he's like, bannisters, I need you to dig through your couches. Whatever, you know, money that you have that's spare, anything liquid you have, I need it. You know, SpaceX needs it.
Host
Oh my God.
Cyan Banister
And at this time, the rockets were blowing up on the launch pad. People all around were just like, you know, private citizens have no business, you know, in space. And that's why it's failing. A lot of people don't realize that in order for it to get an airplane in the sky to fly, we had to crash a lot of planes. And this type of engineering is not easy and it involves a lot of failure. And failure is part of the progress. And so a lot of NASA people knew this. They knew, like, in order to get a rocket, you've got to fail, fail, fail, fail, fail. And a lot of people said, you never have reusability, he'll never be able to do it. But it was Luke's conviction. And at the time, I had just exited from Ironport, I had my first liquidity event. And I was like, what do I do with this? And so Luke and Scott convinced me to put everything that I made in Ironport when we sold to Cisco into SpaceX. What they basically said, if you're an able bodied person, you're infinitely employable, you're young, you have a safety net, like, this is what you do with it. And I was just like, yolo. So I did it. And then afterwards I was like, what have I done? Because I Had a startup at the time that was struggling, that I was building and I was like, wow. I just literally put all my chips on a color and just let it ride for 20 some odd years now. And it ended up being the best investment I'll probably ever make in my life. Is completely changed the trajectory of my life and yeah, that is insane. Yeah, at the time, it did not look like the smartest investment at the time. Like I had friends who were just like, you just lit your money on
Host
fire and you didn't sell any of it?
Cyan Banister
No, what?
Host
No, not.
Cyan Banister
I mean, I diversified a little bit like when I was at Founders Fund, but for the most part now.
Host
Wow, I'm glad I asked that story.
Cyan Banister
Yeah, it's a good one.
Host
What did that teach you about risk?
Cyan Banister
What did it teach me about risk? Well, you know, a lot of people already know my background story. I was homeless for a period of time and I had to take a lot of risk being a homeless person. But at the same time, I had a lifetime of conditioning of people saying, you know, you need to get a job that has a retirement plan, a 401k or some sort of pension. And then if you ever have any savings, you should be putting it into the S&P 500 or buy land or things that are less risky. When my peers and my friends were telling me, no, you need to actually put it into high risk startups because the alpha is there. And they start explaining me words that I had never even heard before. I didn't even know that angel investing was a category of investing you could even participate in. That's the thing that actually upset me the most. So when I started investing, I started realizing that I was part of a special club that I lucked into. A special club that was not available to everybody. And as an engineer, you know, I was an accredited investor. So I could have put 5,000, $10,000 into Uber or any of these companies. After SpaceX, I started taking more risks. I became a little bit addicted. And Scott just basically said, you know, I don't like meeting lots of people. I don't like going to these demo days. I don't want cold emails, I don't want any of this stuff. So if you want to, I want to farm my existing network in my little PayPal mafia world and I want you to go out and establish yourself. And so for the first 10 years of my investment career, I was at, you know, TC40, TC50 Disrupt launch demo days, YC up at TED, you know, like networking my ass off it was not overnight success story. So I wrote a lot of checks that failed and I had to calibrate my sort of pattern matching over time. In order to become good at early stage investing you really have to lose a few times. One you learn how to internalize that, how to treat the founder, what to be attached to, what to be unattached to and you know how to learn from if there was a mistake there of any kind what you can learn from it. So I think it definitely made me very risk tolerant.
Co-host
Today's episode is sponsored by VCX by Fundrise, the public ticker for private tech allowing investors of all sizes to invest in venture capital. Learn more@getvcx.com Some of you may not have heard this yet, but our sponsor Public just launched something called Generated Assets and it brings AI into investing in a way I've honestly never seen before.
Host
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Host
which of the companies either in your angel portfolio or I'm sure in the long journey portfolio are you most excited about right now? Oh gosh, there's no phase substrate but
Cyan Banister
yeah, substrate and then I would say becoming bio. Becoming bio is the substrate of biology and then substrate obviously is the substrate of technology and I think both are necessary for the future that's coming. Diamond Foundry as well, which is one of the companies that you listed, makes man made diamonds and diamond wafers and also industrial diamonds for cutting and a lot of people when I invested in that company said that all they could see was that they were going to make fancy diamonds, which is what they used to fund the company. And they couldn't see past that. They were just like, you can only sell so many diamond rings. People aren't going to want synthetic diamond rings. And that's just not true. But the real money was in the industrial diamonds and then the wafers and seeing the AI and crypto was coming, which the founder saw. And so I think those three are probably my most exciting investments right now that are inflecting. But obviously there's a lot of really smaller investments. I'm really kind of interested in how AI and personal devices are going to turn out like little stuffed animals. We're starting to see a lot of those. And I think one of them is going to end up being a Tamagotchi or Labubu. But it's going to be actually useful rather than just a little thing that you have to feed or it dies. You know, it's actually going to help you in life. Right. And so I'm kind of interested to see, like, where that goes. I'm interested in seeing how people use this new paintbrush in new ways. I think in two to three years, we're going to see a consumer wave. Like right now we're just trying to figure out, like, how it all works and which companies can use it and where the value is. But eventually it's going to be a huge consumer wave and signs are going to change. Outside fashion is going to change. If we can somehow work out our stuff with China, manufacturing will come back. Vime manufacturing, which I brought up, is going to be a thing you're going to say, I have this little widget. If only I could print it and get it made and get a million of them made, then I can also just go direct to consumer and you're going to start seeing a lot of that. So I am still looking for the Alibaba of the Americas. I haven't found it yet. I'm still turning over stones there, trying to find. So I always like to put that out there in the wild in case someone claims they have. That company had many pitches. None of them have panned out yet. What else am I excited about? Yeah, I think those three, I mean, bringing computer, like basically bringing semiconductor manufacturing back to the Americas is a really important problem to solve. There's also some defense companies we're in that we're excited about. Power generation, a lot of deep tech right now.
Host
Deep tech is cool.
Cyan Banister
Yeah, it's Very cool. Very hard, but very cool.
Host
I mean, you especially with your track record, have been a strong proponent of America.
Cyan Banister
Oh yes.
Host
And reindustrialization.
Cyan Banister
Yes. From, from day one.
Host
When does that consolidate down?
Cyan Banister
Well, I think the cost of manufacturing and robotics has gone down considerably. And so the ability to play and come up with prototypes and also the fact that SpaceX paved the way for Avarta, you know, for other types of startups to dream that they could even exist in that space. You know, it took a SpaceX in order to even open up that category. Most people wouldn't have touched it. And so I think that's part of why now. I think the other thing is I was reading an article that there's a space war going on where we have satellites by non allied countries collecting data and they're destroying some of our satellites and there's this race to the moon and so we're in a bit of a, I wouldn't call it a cold war, but it's definitely a war, a technology war with countries that don't have our interests. And so I think that's another reason of why now drones wars are going to be fought with robotics in the future. There's not going to be humans on the battlefield, there's going to be robots and there's going to be technology and BattleBots is going to be a thing. And so if you look at Andura, for example, they have this product that can take out a whole drone swarm in one go. We're going to start seeing things like that where maybe people don't want to work with Anduril so they want a competitor. You know, maybe the other defense primes need to have a product. So you're going to see a lot of startups playing in that world. I do think that obviously Enduril is going to consolidate a lot of it and become one of the top defense primes over time, but they're already well on their way. So I think that's why now. I, I tend to not play in the why now space though. Yeah, I tend to play in the what's coming space. And so I think what's coming is nanotech, biotech, I'm much more interested in that. I'm also really, really interested in what bottlenecks get removed because of AI or information that we're able to get and analyze for the first time in history. So there's all these really, really neat data sets that once you start looking through them, we're going to be able to solve some of the world's hardest math problems and the hardest problems and be able to take us more into this Star Trek future that we could have. And so I'm thinking about that. So when people right now are investing in things that are hot, I did the infrastructure layer for that because six years ago we were thinking about the infrastructure layer of crypto and AI because we had a bunch of friends at Singularity who've been talking about AI for years. Now I'm thinking, okay, what does this all enable next and what are the problems of it and what are we going to see? Because the alpha is there, it's not in what's happening today. If I'm chasing everything in the hyper competitive deals of today, I'm going to lose money. So I've got to try to find things at lower prices that are still a moonshot that I can get a good percentage of ownership like a good seed fund should do. I tend to not chase many deals that are really hot today.
Host
So is that Cyan's secret to success?
Cyan Banister
Yes, it should be all seed funds secret to success, but it's not really.
Host
So as we close out, I like to do our Brex question. So Brex is all about performance, spending smarter, moving faster. But I kind of take it more of like a personal bend to it. I do think that performance is about who you surround yourself with and the relationships that you keep, ones that have like mentored you a long time or inspired you. So for you, who are a couple people, maybe one or two that have
Cyan Banister
inspired you, well, Peter Thiel, obviously Marc Andreessen, despite the two of them, probably would not want to be in the same sentence together being heralded. But Peter Thiel hopefully is obvious to people why I love him. And he was my partner for four years at Founders Fund. And I always like to joke that I didn't go to university, but I went to the Peter Thiel University. And he taught me so much about myself and about investing and about the world. I've never met anyone more tolerant, more open minded. He gets such a bad rep for a lot of things, but he's just probably one of the most poorly understood people.
Host
Why do you think that?
Cyan Banister
Because he's inaccessible. Because he does weird things that no one can predict, because he thinks really long and he's also operating a thousand feet above everybody else.
Co-host
Right.
Cyan Banister
Like his mind is not like other minds. And so when you encounter something like it's kind of like Elon, you know, you, you don't know what to do with it. So it's just easier to hate it. And the other thing is, you know, he is libertarian, right leaning. That is not the most attractive, sexy thing to a lot of people. Marc Andreessen was my hero when I was a teenager. And I used to see him on the COVID of magazines and what he basically he was, you know, the Netscape was his thing. And Netscape changed my world and changed the whole world. And so seeing kind of his contributions to changing the world, I told myself when I was a teenager, I'm going to meet that guy someday. I'm going to sit in a room with him and he's going to ask me a question and he's going to value me. And I didn't meet him until that was true. And so I wouldn't say he's a mentor actively, but my mentors are far off. You can learn a lot from people without ever knowing them, just by watching them and observing them. And kind of like a metagame in Mafia. You don't need to know Peter necessarily. You can listen to the people who've been around him. You can witness him if he gives a talk and you're lucky enough to see it. And maybe you'll be in the same room with him someday, but for the most part, he could be your mentor without ever meeting him. If you're open minded and you ask yourself, why? Why would he do this? And don't make assumptions. Like, don't assume things about Peter. Just say, why would he do this? Here are the 50 different reasons why, potentially, and one of them might be true. I'm trying to think of who else. Scott Cook. I love Scott Cook from Intuit.
Host
Okay.
Cyan Banister
He's definitely one of my heroes. I love him. I've never met anybody in my life with more executive function who has a complete understanding of the lay of the land of his company, his employees, his culture, his board, and kind of the emerging technologies of the world. Who is so down to earth, so wonderful, like, Scott is probably like the gold standard, I would say, for just fine human being in an executive position. And then Rick Rubin.
Host
Ooh.
Cyan Banister
It is my dream. I'm gonna put it out in the universe that I get to meet Rick Rubin someday. Cause I do think that he's the first person besides Bill Murray that I've ever seen in my life who I think my mind is similar to and comes up with the answers to things based off of this openness to, for lack of a better term, the universe presenting to you solutions.
Host
I hope you guys meet.
Cyan Banister
I hope so too.
Host
I really, really want to meet he has a podcast. Why don't you go on? I know.
Cyan Banister
I don't know how to reach him. I don't know how to reach his team, really. I just keep putting it out in the universe, and I figure it'll eventually happen.
Host
Okay, we'll put it out right now. Tetragrammaton. All right. I hope I said it right. Yeah, but you made a really hard word as your podcast name. Cyan needs to come on.
Cyan Banister
Yeah, he brought on Bill Gurley and Bill. You know, I'm sure they talked about Uber, but we brought Uber to Bill Gurley, so.
Host
Oh, hey, hey. That's the source.
Cyan Banister
Maybe that'll get me on. I don't know. We'll see.
Host
That's exciting. Okay, we'll put that on the universe for you.
Cyan Banister
We'll put that out in the universe.
Host
Well, thank you so much, Cyan. This was such a thoughtful and invigorating and really, like, deep conversation. And then it's also just really. It's so fun to spend time with you and, like, get in your brain and, like, just understand, like, how curious you are and, like, unapologetically curious. Like, I think there was a tweet last week, and you're like. And people were all complaining about the Peter Thiel event. Like, oh, someone, like, said that they were, like, embarrassed to go. It's like, go to events.
Cyan Banister
Like, go to events. Take the pictures. I really feel like we need to get over this shame by association. You should be curious and have your own thoughts. You are an entity. It's kind of like we're glasses with water inside, but we're separate and together. But at the same time, if you stand next to another glass with water inside doesn't mean you're filled with that water. You know what I mean? You can be curious. And for a place that talks about restorative justice and talks about, you know, we give people who've murdered people more of a chance than we give someone who said the wrong thing. You know, that's what needs to end, is, you know, Peter holds these events where people talk about everything, and I love it because they go from anywhere from, you know, child rearing to, you know, what's better, having atheism or Christianity to rule, you know, a nation. What should be more prevalent. Right. It's not because he believes any of these things. It's because he wants to hear them all.
Host
Yeah.
Cyan Banister
You know, because he wants to figure out where he stands on it. And in order to figure out where you stand on anything, you should hear all Sides. And not only that, but try to understand it completely before you make, you know, that decision internally. And tribalism in that regard should stop. So I thought Ezra's apology, or whatever it was, you know, it's like, I went to an event, but I didn't like it. It's like, come on. It's so awful. I'm so tired of seeing this. It's like, you went to the event. You had a good time. You wanted to be there. Trust me. Just say it.
Host
Yeah.
Cyan Banister
You know, if you get invited to a Peter Thiel event, go, like, do not shy away from it. It does not make you anything that anyone's gonna accuse you of. You don't eat babies. You don't know Epstein by proxy. You know, like, you are not a. You are not a. You are not a. Just go. Don't be afraid of those words. Because I think that we've weaponized them to the point where they're going to become meaningless, and we don't forget what they really are. Racism is real. It's a problem. And so if we call everyone a racist, then we can't find the real ones. If we call everyone a. How are we going to find the real. We need to be very careful with this. Of pointing fingers and trying to blame people and signal that we're like, our group is somehow pure. It's just. It's gotta stop. And so that's why I sent that. I was, like, proud to know Peter not gonna change. And if it gets me canceled, I really don't care.
Host
That was a banger. You do eat Mars babies.
Cyan Banister
Yeah, I eat Mars babies. I was like, yeah, I eat babies, but only from Mars. I thought that was pretty funny. I'm glad you liked it. Because I was like, if they stop and think about it, they're like, there's no babies on Mars. Yeah. Cause I don't eat babies. One of my friends has a quote that I really love. He said, and this is going to be a little controversial, so I apologize.
Host
Let's go.
Cyan Banister
He's like, I've all the people I've ever wanted to, which is none. Right. He doesn't want to. I've eaten all the babies I've ever wanted to, which is none. So it's. The other thing is, you can tell the health of a nation by its ability to tolerate comedy and rap music. Those two things have to exist for freedom. Rap music and comedy. And if either of those start to disappear, you're in trouble. And comedy started disappearing from our universities first.
Co-host
Yeah.
Cyan Banister
And so that should have been a warning sign to the whole nation that we were in trouble. And unfortunately, we didn't speak up for them. We didn't speak up for the Republicans that got booed off campus and had cement bombs thrown at them. And now we're in this situation where we're starting to see a lot of civil unrest around speech and things like that, like what can be said and not said. And so we have to fight for people's right to say uncomfortable things and things that you disagree with. And so that's something that I care deeply about. And a lot of what I do and what I invest in is for that purpose, which is I want to support free speech.
Host
It's amazing.
Cyan Banister
Yeah, it's my number one cause. So a lot of people want to. There's nothing wrong with it. Want to save the oceans. Want to bring water to Africa, Want to cure cancer. I want to protect free speech.
Host
And this is why you must follow Cyan on X and on Mafia. Hopefully there's a nice one.
Cyan Banister
Hopefully there's another season. I don't know if I was interesting enough to come back, but we'll see.
Host
I don't know. Silent Killer over here.
Cyan Banister
Silent Killer.
Host
Thank you Silent.
Cyan Banister
Thank you Molly. Thank you so much.
Co-host
Hey, it's Molly. If you enjoy our interviews, check out our newsletter Sorcery VC where we deliver a once a week top deals and tech headlines. Email and also go deeper on our podcast interviews. Subscribe to Sorcery Today and don't forget to subscribe to the podcast on YouTube, Spotify, Apple or wherever you listen. Link in Description to sign up.
In this engaging and wide-ranging episode, Molly O’Shea sits down with legendary angel investor Cyan Banister for a deep dive into the mindset, stories, and principles that have made her one of the most successful investors in tech history. Cyan shares behind-the-scenes tales from iconic investments (SpaceX, Uber, Niantic, Anduril, Diamond Foundry, and more), her unique approach to risk and curiosity, the value of games and neurodivergence in Silicon Valley, and why she’s unapologetically vocal in support of free speech and curiosity—even on the most controversial topics. The conversation is playful, honest, and packed with memorable insights and personal stories.
“Luke came over to our house and he’s like, Bannisters, I need you to dig through your couches. Anything liquid you have, I need it. SpaceX needs it.” (00:01, 66:59)
“I gauge my success rate by how many things do they touch without my permission?... I want people to rifle through things and feel so at home that they can play.” (06:09)
“It was challenging. Really super challenging for me to lie. I do not like it. And it made me very uncomfortable… but Dylan was just like, I couldn’t tell. You’re just very hard to read.” (15:44)
“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 without… all the small talk.” (22:58)
“We have this misconception that our personality is fixed… but you can actually surgically go in and alter your personality. It takes effort and time and facing the ugly truth about yourself.” (33:48)
“If I ever had a chance to invest in anything, it’s right now… just paying attention and a gut feeling that there’s something special here and I’m witnessing it.” (46:30)
“There’s an underbelly to all of this. There’s a utopian future and a dystopian future… AI is the same [as a gun], and so we really have to think about how to be responsible…” (52:25)
“If you’re not getting into medicine or like a hard thing that requires four to six years of school, I’m not sure people should be going to school right now.” (54:03)
“If you get invited to a Peter Thiel event, go. 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.” (86:06)
“You can tell the health of a nation by its ability to tolerate comedy and rap music… Those two things have to exist for freedom. And if either of those start to disappear, you’re in trouble.” (87:23)
“He taught me so much about myself and about investing and about the world… he’s just probably one of the most poorly understood people.” — On Peter Thiel (80:23)
This episode is a masterclass in combining curiosity, risk-tolerance, philosophical rigor, and playfulness for both investment greatness and a fulfilling, creative life. Cyan Banister’s worldview embodies relentless asking of “why,” openness to experience, deep trust in people with conviction (from Luke Nosek to Peter Thiel), and an unapologetic embrace of the weird and magical. Whether you’re a founder, investor, or just someone seeking inspiration to live life more curiously, her stories and mindset offer both practical wisdom and motivation.
End of Summary