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

Cyan Banister put her entire IronPort exit into SpaceX when the rockets were still blowing up on the launchpad. She never sold. It became the best investment of her life. She is Co-Founder and General Partner at Long Journey Ventures, spent 4 years as a partner at Founders Fund, and with her husband Scott Banister has built one of the most successful angel portfolios in the world across 20+ years of investing together: SpaceX. Anduril. Uber. PayPal. Affirm. Flexport. Postmates. Niantic. Opendoor. Carta. Together AI. Diamond Foundry. Crusoe. Flock Safety. Substrate. Brave. Depop. Calm. Fivetran. Zappos. Cyan joins Sourcery at Long Journey's HQ to break down how she actually sources deals, why she refuses to chase hot rounds, and what she is buying next in nanotech and biotech. She found Niantic in a customer support inbox at Hint Water. She found Uber by asking taxi drivers what their day was actually like. Her point is that the alpha is in paying attention, and that the best investments arrive as a feeling before they arrive as a thesis. Cyan Banister: https://x.com/cyantist Molly O’Shea: https://x.com/MollySOShea Sourcery: ⁠https://x.com/sourceryy 𝐄𝐏𝐈𝐒𝐎𝐃𝐄 𝐋𝐈𝐍𝐊 YouTube: https://youtu.be/810VlN3lkqQ 𝐒𝐏𝐎𝐍𝐒𝐎𝐑𝐒 • Brex https://brex.com/sourcery—The modern finance platform, combining the world’s smartest corporate card with integrated expense management, banking, bill pay, & travel. https://brex.com/sourcery • Turing https://turing.com/sourcery—Turing delivers top-tier talent, data, and tools to help AI labs improve model performance—and enables enterprises to turn those models into powerful, production-ready systems. https://turing.com/sourcery • VCX https://fundrise.com/vcx—VCX is the public ticker for private tech, allowing investors of all sizes to invest in venture capital. View The Portfolio at http://GetVCX.com http://getvcx.com • Deel https://www.deel.com/sourcery—Deel is the global people platform that helps startups hire, manage, pay, and equip anyone, anywhere. Trusted by more than 35,000 fast-growing companies, Deel is the people platform that just works, so teams can scale without the chaos. Visit: https://www.deel.com/sourcery • Public http://public.com/sourcery–Investing platform Public just launched Generated Assets https://public.com/generated-asset, which lets you turn any idea into an investable index with AI. With Generated Assets, you can build, backtest, refine, and invest in any thesis with AI. Gone are the days of one-size-fits-all ETFs. https://public.com/sourcery Follow Sourcery for the latest updates! https://www.sourcery.vc https://www.sourcery.vc/ Disclosure Paid Endorsement. Brokerage services by Open to the Public Investing Inc, member FINRA & SIPC. Advisory services by Public Advisors LLC, SEC-registered adviser. Crypto trading provided by Zero Hash LLC, licensed by the NYSDFS. Generated Assets is an interactive analysis tool by Public Advisors. Output is for informational purposes only and is not an investment recommendation or advice. See disclosures at public.com/disclosures/ga. Matched funds must remain in your account for at least 5 years. Match rate and other terms are subject to change at any time. 𝐓𝐈𝐌𝐄𝐒𝐓𝐀𝐌𝐏𝐒 (00:00) Cyan Banister, Long Journey Ventures (01:13) Inside Long Journey HQ (02:17) The wild story behind the office mural (05:32) What Cyan's actual house looks like (08:08) What the Long Journey logo actually means (10:41) How Cyan became one of Mafia's breakout stars (15:42) The first time she's ever had to lie to win (16:30) What really happens off-camera at Mafia (18:58) The blooper reel nobody's seen yet (22:33) The one thing Mafia is missing (23:54) Inside Brian Singerman's $40-a-month boardgame club (31:36) Cyan's Serendipity (43:56) The "why" behind her biggest investments (1:01:57) Full list of Cyan's investments (1:04:28) All-in on SpaceX (1:08:57) Why she never sold a single SpaceX share (1:12:53) Top Bets: Becoming Bio + Substrate (1:15:52) Why America's reindustrialization moment is now (1:19:16) The mentors who shaped who she is today (1:22:54) Manifesting Rick Rubin (1:24:00) Real take on the Peter Thiel events

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

• 0:00Molly O'Shea?

  Congrats on SpaceX.

• 0:01Speaker 01

  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 iron port when we sold to 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 Founder's 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 you anything that anyone's going to accuse you of. You don't eat babies.

• 0:34Molly O'Shea?

  SpaceX, Anduril, 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, Hargomatic, Diamond Foundry, very interesting. Upstart, FiveTran, Forge, Open Door. I had a lot of fun with Kaz. We did a really recent interview there. Calm, TruMed, and Pusso. So what's your favorite?

• 1:13Molly O'Shea?

  All right, so we are at Long Journeys HQ. It's called the Boobies Place, the Bubby's Place?

• 1:20Speaker 01

  Bubby's.

• 1:24Speaker 01

  Bubby's Place, yes. Bubby might have some boobies, but it's Bubby's Place.

• 1:32Molly O'Shea?

  And we're in a very special room right now. With Cyan Manister, the star, one of the stars, because I also called Dylan the star of Mafia. You're all stars of Mafia in your home.

• 1:47Speaker 01

  Well, we are in Long Journeys headquarters. And this room that we're in right now, they call it Cyan's Lair.

• 1:56Speaker 01

  I have a tendency, wherever I'm at, including at Founder's Fund, I was behind the bookshelf that turns. I really like darkness and artificial light is not my friend.

• 2:07Molly O'Shea?

  Oh my God.

• 2:08Speaker 01

  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 tend to find me in here.

• 2:17Molly O'Shea?

  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 of the walls down here in the lower level.

• 2:40Speaker 01

  Yes, everything's covered.

• 2:41Molly O'Shea?

  What is this?

• 2:43Speaker 01

  So this is done by an artist named Dave Zacken 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 looked 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.

• 3:02Molly O'Shea?

  Really?

• 3:02Speaker 01

  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, 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.

• 3:23Molly O'Shea?

  Oh wow.

• 3:24Speaker 01

  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, you know, bringing a lot of this joy to the world. And then, one day I had this fantasy that, I was like, wow, I wonder if Dave Zacken, this is, 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.

• 3:54Molly O'Shea?

  Yeah.

• 3:54Speaker 01

  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. 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.

• 4:32Molly O'Shea?

  Really?

• 4:33Speaker 01

  Ceramic studios, yeah. And what he does is he repaints it. And re-glazes it.

• 4:40Speaker 01

  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.

• 4:54Molly O'Shea?

  There's so much going on right now.

• 4:56Speaker 01

  Yes, yes.

• 4:57Molly O'Shea?

  In case you didn't know that.

• 4:58Speaker 01

  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 thirty bucks for, I think, both of them.

• 5:09Molly O'Shea?

  What?

• 5:10Speaker 01

  Yeah, and so I love walking around town with them.

• 5:12Molly O'Shea?

  Oh, my God.

• 5:14Speaker 01

  It brings a lot of joy to people.

• 5:16Molly O'Shea?

  And is Dave also the ceramicist of the hammer?

• 5:21Speaker 01

  No, I need to, 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, I didn't find them, that's why I don't know much about them.

• 5:32Molly O'Shea?

  This is so fun. I just can't imagine what your house looks like, if this is your office.

• 5:37Speaker 01

  Yeah, it's different, it's a different kind of crazy. It's different. I like, I like to mix it up. It's not quite like this, but it's, I look like if you were to go to Goodwill for your design. I know that sounds weird.

• 5:50Molly O'Shea?

  What?

• 5:51Speaker 01

  Yeah, it's more thrift store oriented. And everything's vintage. And everything's odd. I, I tend to like, if people come to my house, I gauge my success rate by what, how many things do they touch without my permission?

• 6:07Molly O'Shea?

  Oh, interesting.

• 6:09Speaker 01

  Yeah, so what happens when you see something and you, it sparks like your inner child?

• 6:14Molly O'Shea?

  Yeah.

• 6:14Speaker 01

  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. Because I want it. I actually want people to rifle through things and feel so at home that 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, this is a silly place. I'm free to be silly.

• 6:46Molly O'Shea?

  Is that the most, like, touched thing?

• 6:48Speaker 01

  The fish.

• 6:49Molly O'Shea?

  That's what people go for the most?

• 6:51Speaker 01

  Yeah, the fish, the fake snowballs. People, I mean, that's obvious. Like, it's like, oh, there's snowballs. Let's throw them. There's also like 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. 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.

• 7:18Molly O'Shea?

  And you don't like candles, right? So there's two candles on the wall. What do those represent?

• 7:22Speaker 01

  I hate candles.

• 7:24Molly O'Shea?

  Yeah.

• 7:24Speaker 01

  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.

• 7:56Molly O'Shea?

  Oh, wow.

• 7:58Speaker 01

  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.

• 8:06Molly O'Shea?

  That's, yeah, that's good.

• 8:08Speaker 01

  Yeah.

• 8:09Molly O'Shea?

  And I know no one can see this in frame, but I think it like 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?

• 8:20Speaker 01

  Yeah, so it's an eye. And you know, 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. It's supposed to look over you. And it's very popular in Greece and, and other places that aren't the United States. But it's actually the eye of a sheep. And people say, "Well, why is sheep like being a sheep is bad?" Is being a sheep bad? You know, it's um, I really like-

• 8:51Molly O'Shea?

  I think it's bad.

• 8:52Speaker 01

  Bad, it's bad.

• 8:56Speaker 01

  That's good, that's really good.

• 9:00Speaker 01

  I like taking phrases that we 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, you know, I 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 sheepdog, 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, there's they anoint another bellwether. But there is a leader of sheep.

• 9:42Speaker 01

  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.

• 10:21Speaker 01

  And so it's kind of a play on this concept of, you know, don't just take a sentence at face value and not like 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. And its name is bellwether.

• 10:38Molly O'Shea?

  Wow, hello, bellwether.

• 10:42Molly O'Shea?

  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 Founder's Fund, could you explain it and like who is also involved?

• 10:58Speaker 01

  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, the sheriff can see who is Mafia and who isn't during the night.

• 11:42Speaker 01

  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. You know, 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,

• 12:22Speaker 01

  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.

• 12:32Molly O'Shea?

  Yeah.

• 12:32Speaker 01

  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 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, you know, I played with Dylan." 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, um.

• 13:06Molly O'Shea?

  Moxie got a lot of hate.

• 13:08Speaker 01

  A lot of hate, but as you can see, Moxie's quite good. And he lasted a lot longer than I thought he would.

• 13:14Molly O'Shea?

  Yeah.

• 13:15Speaker 01

  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.

• 13:28Molly O'Shea?

  Oh, my gosh.

• 13:28Speaker 01

  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 beat.

• 13:37Molly O'Shea?

  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.

• 13:46Speaker 01

  We would have won. They would have taken out Sam and Ryan. And, um, you know, eventually figured out that Palmer, you know, was one. But, uh, 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.

• 14:30Speaker 01

  So I'm surprised that they didn't use the intel, but maybe they just didn't.

• 14:33Molly O'Shea?

  And they killed you then after that?

• 14:34Speaker 01

  Yeah.

• 14:35Molly O'Shea?

  Yeah, of course.

• 14:35Speaker 01

  Yeah, they killed me.

• 14:36Molly O'Shea?

  Yeah, you knew too much.

• 14:38Speaker 01

  Too quiet. Apparently, if you're too quiet and you're observant, it gets you in trouble. They automatically assume you're trouble.

• 14:44Molly O'Shea?

  What do you think the best strategy is through all of it?

• 14:48Speaker 01

  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, uh, 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, but. For me, I mean, I have, 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.

• 15:29Speaker 01

  And, 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 gonna work, you know, a few times.

• 15:42Molly O'Shea?

  Well, you've now been outed.

• 15:43Speaker 01

  I've been outed now.

• 15:44Molly O'Shea?

  Yeah, there's millions of views on that one.

• 15:46Speaker 01

  Yeah, yeah, I've been outed now. But that was my first time being Mafia or Wolf. I have never been a killer before, I've never had to lie like that. And so, I gotta say that was challenging.

• 15:58Molly O'Shea?

  Really?

• 15:58Speaker 01

  It's 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."

• 16:09Molly O'Shea?

  Yeah.

• 16:10Speaker 01

  He's like, "You just look kind of like, hmm, you know, very difficult to read." But it was super fun, I really hope Slona 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.

• 16:26Molly O'Shea?

  Yeah.

• 16:26Speaker 01

  You know, because I do think there were some really good players in there that should return.

• 16:30Molly O'Shea?

  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 understa- 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, kinda 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...

• 16:58Speaker 01

  Yeah, some of 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, you know, I love Moxie and... You know 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.

• 17:35Molly O'Shea?

  Really?

• 17:36Speaker 01

  Yeah, so it's the exact same face.

• 17:37Molly O'Shea?

  I didn't know that.

• 17:38Speaker 01

  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.

• 17:43Molly O'Shea?

  No way. Oh, my God.

• 17:46Speaker 01

  Yeah, so it'd be super cool if we got some of those folks on.

• 17:49Molly O'Shea?

  Yeah, you guys should have recreated that.

• 17:51Speaker 01

  I would love to see Raboy and, you know, Peter.

• 17:53Molly O'Shea?

  Yeah.

• 17:54Speaker 01

  That would be so cool. That'd be so cool.

• 17:56Molly O'Shea?

  So cool.

• 17:56Speaker 01

  I don't know if Peter would do it, but who knows? You never know.

• 17:59Molly O'Shea?

  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.

• 18:10Speaker 01

  Nope.

• 18:11Molly O'Shea?

  Some of us do not talk to each other anymore.

• 18:13Speaker 01

  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, 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, it's kind of like a Mafia because they really, really help each other out.

• 18:53Molly O'Shea?

  I feel like Elon would go.

• 18:55Speaker 01

  Mm-hmm. I think he would.

• 18:58Molly O'Shea?

  So 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.

• 19:06Speaker 01

  Yeah, I don't know if I'm allowed to say because it might get me in trouble.

• 19:09Molly O'Shea?

  Probably.

• 19:10Speaker 01

  But yeah, there was some really spicy moments between a few of the people and they got cut.

• 19:15Molly O'Shea?

  Dude.

• 19:15Speaker 01

  So maybe someday Solana can do like an outtake of some of the things.

• 19:20Molly O'Shea?

  It sounds like a quick blooper reel.

• 19:24Speaker 01

  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 to 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 you imagine there's like a lot more of it.

• 19:46Molly O'Shea?

  Oh, my God.

• 19:47Speaker 01

  And...

• 19:49Speaker 01

  Just really funny comments and side comments. You know, some fun stuff which I won't get into with Palmer and Sam Altman.

• 19:59Speaker 01

  They're friendly. It wasn't bad. 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?

• 20:06Molly O'Shea?

  Yeah.

• 20:07Speaker 01

  This is crazy.

• 20:09Speaker 01

  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.

• 20:17Molly O'Shea?

  Yeah.

• 20:18Speaker 01

  So maybe they'll do like a blooper reel or something like that someday.

• 20:20Molly O'Shea?

  It'd be fun. I'm excited. Hopefully, Solana, you make a season two.

• 20:25Speaker 01

  Oh, I hope so.

• 20:26Molly O'Shea?

  I would hope so.

• 20:26Speaker 01

  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.

• 20:34Molly O'Shea?

  No. Really?

• 20:35Speaker 01

  And so we were sworn to secrecy. We couldn't tell anybody anything. I didn't even tell my partners here about it.

• 20:41Molly O'Shea?

  What?

• 20:41Speaker 01

  And I actually was really proud of not telling anybody because the whole firm got to be surprised by it. Like, just on the random ones they have afternoon, they were like texting me, they're like, "What?" I'm like, "Surprise." I just knew you'd love it, so, yeah.

• 20:58Molly O'Shea?

  So why did he wait so long to release it?

• 21:01Speaker 01

  Editing.

• 21:02Molly O'Shea?

  Really?

• 21:02Speaker 01

  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?

• 21:21Molly O'Shea?

  Yeah.

• 21:21Speaker 01

  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.

• 21:35Molly O'Shea?

  Yeah.

• 21:36Speaker 01

  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.

• 21:54Molly O'Shea?

  Yeah.

• 21:54Speaker 01

  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.

• 22:04Molly O'Shea?

  Wow.

• 22:05Speaker 01

  Yeah, it looked simple, but it was definitely not simple. It would be very hard to produce that show.

• 22:10Molly O'Shea?

  I would imagine, yeah.

• 22:12Speaker 01

  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.

• 22:19Molly O'Shea?

  Yeah.

• 22:19Speaker 01

  This is not the first time, you know, Chris Saka and a couple of other people tried to make it with Werewolf.

• 22:25Molly O'Shea?

  Mm-hmm.

• 22:25Speaker 01

  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.

• 22:33Molly O'Shea?

  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 like confessionals.

• 22:56Speaker 01

  Ooh.

• 22:57Molly O'Shea?

  You're missing the confessionals.

• 22:58Speaker 01

  Confessionals.

• 22:59Molly O'Shea?

  Yeah.

• 23:00Speaker 01

  That would be great. Ah, we should add that.

• 23:02Molly O'Shea?

  Mm-hmm.

• 23:03Speaker 01

  Yeah, I, um, 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.

• 23:27Molly O'Shea?

  Mm-hmm.

• 23:27Speaker 01

  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.

• 23:38Molly O'Shea?

  Yeah.

• 23:38Speaker 01

  It's a really interesting thing. Um, 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.

• 23:52Molly O'Shea?

  Yeah. Yeah, that is really fun. I, um, I recently had Brian Singerman on, who gave you a really great shout out.

• 23:59Speaker 01

  Love Brian.

• 24:00Molly O'Shea?

  Yeah, he's awesome.

• 24:02Speaker 01

  He's the best.

• 24:02Molly O'Shea?

  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.

• 24:17Speaker 01

  He got me into board games.

• 24:18Molly O'Shea?

  Really?

• 24:18Speaker 01

  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 a board game of the month club and they would pay me $40 a month.

• 24:29Molly O'Shea?

  $40 a month?

• 24:30Speaker 01

  And then what I would do-

• 24:31Molly O'Shea?

  Diane, what are you doing?

• 24:33Speaker 01

  You know, I got this as 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.

• 24:57Molly O'Shea?

  Yeah.

• 24:58Speaker 01

  It's not fun, especially if you're really into board games. And so Splinter ended up being one of our favorite games. Machikooru, 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 like-

• 25:25Molly O'Shea?

  Oh my god.

• 25:26Speaker 01

  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 Brian Singerman.

• 25:36Molly O'Shea?

  Really?

• 25:37Speaker 01

  Yeah, he's the best.

• 25:38Molly O'Shea?

  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, 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, 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.

• 26:23Molly O'Shea?

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• 27:05Molly O'Shea?

  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?

• 27:34Speaker 01

  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 like, 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's 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, 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. 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?

• 28:19Speaker 01

  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. You know, there's people who have like 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 of 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.

• 29:03Speaker 01

  So, it just really depends, but I think it, it's a great reflection of their inner world.

• 29:10Molly O'Shea?

  You're also a prolific poker player.

• 29:15Molly O'Shea?

  I've seen some videos.

• 29:16Speaker 01

  Yeah, I am, I, that, it'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 Ed Jez Merelda. 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, 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.

• 29:49Molly O'Shea?

  Really?

• 29:49Speaker 01

  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 I, one, I didn't realize the thing was live. I did not realize people were watching.

• 30:19Molly O'Shea?

  No.

• 30:20Speaker 01

  I had no idea. None. Two, and, and then I didn't find out till the commercial break or whatever the break was. We like 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?"

• 30:42Molly O'Shea?

  Oh my god.

• 30:43Speaker 01

  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 one, two cards you could have. And he's like, do you have them? Which means he doesn't have them. Right? So, so he's on tilt and he's like,

• 31:26Speaker 01

  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.

• 31:36Molly O'Shea?

  How do you find yourself in these situations?

• 31:40Speaker 01

  That's kind of my life. My life is a series of these types of events. 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.

• 31:57Speaker 01

  I walk off ledges expecting everything's going to be fine. Not literal ledges, but you know what I mean.

• 32:01Molly O'Shea?

  Yeah.

• 32:01Speaker 01

  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.

• 32:36Molly O'Shea?

  Really?

• 32:36Speaker 01

  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 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?

• 33:04Molly O'Shea?

  No.

• 33:04Speaker 01

  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. 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 happening. That's really neat. That's interesting. And I just kind of roll with it.

• 33:37Molly O'Shea?

  What has that taught you about human behavior, though? Because most people don't live like you. They're not as optimistic.

• 33:44Speaker 01

  They could be.

• 33:46Molly O'Shea?

  How can they be?

• 33:48Speaker 01

  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.

• 34:33Speaker 01

  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.

• 34:42Speaker 01

  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? You know, if I say, like, I'm an honest person. 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? 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, 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.

• 35:24Speaker 01

  And I 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. And I would say that's false. That's just a like a limiting thought. And you can change that at any time, it's just it takes a little bit of effort.

• 35:42Molly O'Shea?

  Why do you think people might be afraid to do that?

• 35:47Speaker 01

  People are afraid to show who they really are. You know, 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 is 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.

• 36:30Speaker 01

  But it turns out they're so caught up in their own shit that they don't care.

• 36:34Molly O'Shea?

  Yeah.

• 36:34Speaker 01

  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.

• 36:47Molly O'Shea?

  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, 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, so I don't have to be like stiff, just asking questions like another like VC intro viewer, like, I can make a little funny jokes.

• 37:08Speaker 01

  Yep, you can just be you.

• 37:09Molly O'Shea?

  Pretending I didn't know Jack and Sam were related ends up becoming like a viral video every month.

• 37:15Speaker 01

  Right.

• 37:16Molly O'Shea?

  This is really funny. For people, like, I mean, I think like change is probably the hardest part and is like a biggest limiter.

• 37:27Molly O'Shea?

  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?

• 37:45Speaker 01

  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. And if you watch my X feed, from time to time, I post like openings for Awake Academy 101. And, 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. 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.

• 38:21Speaker 01

  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.

• 39:03Speaker 01

  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. If you spend five minutes a day doing that, you're off to a good start. The next thing is, you know, when you take a shower, is a great time to be really, really mindful about washing your body, washing your hair, you know, the water, the ritual of showering. Don't just be in a hurry. Don't just like jump in there and shower every day.

• 39:48Speaker 01

  You know, make sure that you put that time aside for yourself and really do it right. 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? 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 gonna feel my toes. That's all I'm gonna do, just gonna sit there and feel my toes. And they're there.

• 40:30Speaker 01

  It sounds silly, but a lot of us forget we even have toes. And before you even step out of bed, you know, 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, 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.

• 41:07Molly O'Shea?

  Is that like 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 is commonality?

• 41:18Speaker 01

  Yeah, the number one thing that people have issue with is... Do you like Rick Rubin? Yeah. Okay. So, a lot of people have read Rick Rubin, and 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.

• 42:03Speaker 01

  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, 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, 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. 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,

• 42:48Speaker 01

  "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 gonna get the same results. But if you shake things up, you do things a little differently, you're gonna 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 on to 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.

• 43:33Speaker 01

  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.

• 43:56Molly O'Shea?

  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.

• 44:13Speaker 01

  Oh, it's really wonderful.

• 44:14Molly O'Shea?

  Discover amazing things. So in terms of investments, how has that led you? I mean, you've invested in SpaceX, Uber, Andorol, 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?

• 44:33Speaker 01

  I think 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 Ingris. 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.

• 45:18Speaker 01

  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.

• 46:02Speaker 01

  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 like, I realize it's kind of like a web of thought. I was at Hint Water, 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. And so I stopped for a moment and I'm like, I don't mean to pry. I'm not really reading your tickets, like, don't want to invade privacy. But like, 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 in the bottle caps.

• 46:46Speaker 01

  So right when Niantic spun out of Alphabet, I realized I had to email her. It's not 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 Cara 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.

• 47:30Speaker 01

  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.

• 47:49Molly O'Shea?

  Wow.

• 47:50Speaker 01

  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. Really? 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.

• 48:33Speaker 01

  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, you know, 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 like a bat out of hell and I think I'm gonna die? Like, and what you do is you ask them. You say, hey, what's your life like? Like, what is your day like? And the taxi drivers would tell me, like, well, I wake up, I go to the taxi yard, I give them $200. I'm in the hole $200 from the moment I walk in.

• 49:18Speaker 01

  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. Yeah. 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, you know? 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.

• 50:03Speaker 01

  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 gonna make you a better investor, it's gonna 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 gonna go, especially if it's like a science fiction sort of scenario, and just play with it and make believe,

• 50:45Speaker 01

  and it'll lead you to these amazing outcomes.

• 50:49Molly O'Shea?

  Do you find it interesting that a lot of things that happen in sci-fi movies become real?

• 50:54Speaker 01

  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 turned into reality. Let's just hope that Terminator isn't one of them. We don't want that reality.

• 51:10Molly O'Shea?

  People really like to bring up Skynet all the time.

• 51:12Speaker 01

  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 Founder's Fund, and it's a very important question because what excites you is interesting, but what worries you is also interesting. And I am worried about us moving more and more into a surveillance state that is operated by AI and there's robotics.

• 51:38Speaker 01

  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're in a country that isn't America, it starts to get kind of weird.

• 51:54Molly O'Shea?

  Yeah.

• 51:54Speaker 01

  You know, 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 gonna shut your Waymo down. And not only that, but I'm gonna lock you inside. You know, 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. You know, AI is the same. And so, we really have to think about how to be responsible and how to... You know, I'm all about acceleration, but I'm also about thinking through...

• 52:40Speaker 01

  Should any of this fall into the wrong hands, how could it be used? And so 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, you know, 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.

• 53:25Speaker 01

  That's dangerous.

• 53:28Molly O'Shea?

  Wow. Damn.

• 53:31Speaker 01

  Yeah, sorry.

• 53:32Molly O'Shea?

  That is a worry.

• 53:33Speaker 01

  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 gonna 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.

• 54:01Molly O'Shea?

  Really?

• 54:02Speaker 01

  Yeah, I don't think so.

• 54:03Molly O'Shea?

  What should they be doing?

• 54:05Speaker 01

  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.

• 54:15Molly O'Shea?

  Okay.

• 54:16Speaker 01

  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 wanna 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 gonna see a lot of, maybe not venture scalable businesses, but a lot of newly minted millionaires that are gonna figure out how this all works. And they're gonna set up a completely agenticized business where there's no, no real employees. That's gonna happen. And they're gonna do it from their basement.

• 55:01Speaker 01

  And I'm really excited about that future. I don't, 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, on art and, and basically stole art for training data. Eventually, after a hundred years, all art becomes part of public domain. You can train on it anyway, so it's kind of like, if not now, it was gonna happen. And then, what's really gonna happen is China will sell our art back to us. So they're gonna steal it all anyway, cuz they don't care. And they're just gonna basically come back to us with these models,

• 55:42Speaker 01

  which we've seen with DeepSeek and everything else that's trained on our, our IP, and then they're gonna sell it back to us. So we're gonna be buy, it's gonna be kind of hilarious that we're gonna 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 we're, this is, right now, we're in a period where it's the worst it'll ever be.

• 56:25Speaker 01

  It's gonna be to the point later in the future where you're gonna be able to scan yourself and make a hundred different versions of your show. You know, in different languages and all sorts of stuff. You couldn't do that before. And you're gonna 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 gonna be really, really neat.

• 56:48Molly O'Shea?

  I think that is so, it is like very, um... 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. We 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 showerhead. 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.

• 57:32Molly O'Shea?

  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 don't really know, because maybe some of the schools, like, aren't letting you be an active player.

• 58:04Speaker 01

  I don't think they are.

• 58:05Molly O'Shea?

  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 the different and just go with think.

• 58:24Speaker 01

  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. And so, 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.

• 59:04Speaker 01

  And so, you know, I have friends who wrote scientific papers and used AI for it. And of course, people could tell, you know, 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 gonna have people who are gonna be dismissive of it no matter what, cuz they're gonna like it's hallucinating. It clearly can't be trusted, et cetera. So we're, 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 wanna learn about this philosopher, set me up a lesson, you know, and then I can interrogate.

• 59:45Speaker 01

  You know, 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.

• 59:55Molly O'Shea?

  Yeah.

• 59:55Speaker 01

  You can be self-taught. It's actually possible now.

• 59:58Molly O'Shea?

  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.

• 1:00:10Speaker 01

  Yes.

• 1:00:10Molly O'Shea?

  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.

• 1:00:22Speaker 01

  Thank you.

• 1:00:22Molly O'Shea?

  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.

• 1:00:37Speaker 01

  I think the two of us combined are definitely number one in the world.

• 1:00:40Molly O'Shea?

  Yeah.

• 1:00:40Speaker 01

  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 kinda 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. And but combined together, we're number one.

• 1:01:24Speaker 01

  And so it's just whether or not they're willing to combine us together. You know, TechCrunch gave us the Angel of the Year Award. And they originally weren't only going to let me accept it. And I said, you know, 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, how every the world is supposed to look.

• 1:01:52Molly O'Shea?

  Damn.

• 1:01:53Speaker 01

  But we're really good because we're a great team.

• 1:01:56Molly O'Shea?

  Well, I'm going to name some of those.

• 1:01:58Speaker 01

  OK.

• 1:01:59Molly O'Shea?

  You put it in a list, so I'm going to name all of them.

• 1:02:02Speaker 01

  Oh, dear.

• 1:02:03Molly O'Shea?

  OK, all right, buckle up. We have SpaceX, Anduril. By the way, congrats on SpaceX.

• 1:02:08Speaker 01

  Thank you.

• 1:02:09Molly O'Shea?

  Big.

• 1:02:10Speaker 01

  That's my first check.

• 1:02:11Molly O'Shea?

  Do you get anything cool with that?

• 1:02:12Speaker 01

  Uh.

• 1:02:14Molly O'Shea?

  Are you still in lockup, probably?

• 1:02:15Speaker 01

  Still in lockup, yeah.

• 1:02:16Molly O'Shea?

  So SpaceX, Anduril, 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, Cargo Matic, Diamond Foundry. Very interesting. Upstart, Five Tran, Forge, Open Door, very, had a lot of fun with Kaz. We did a really fun, like, recent interview there. Calm, TruMed, and Crusoe.

• 1:02:50Speaker 01

  Yeah.

• 1:02:51Molly O'Shea?

  So what's your favorite?

• 1:02:52Speaker 01

  Ha, you can't, it's like children, you can't pick your favorite. I mean, there's CEOs in 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 and Earl and you know, it's like, whoa,

• 1:03:35Speaker 01

  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.

• 1:04:05Molly O'Shea?

  Very fun.

• 1:04:06Speaker 01

  And very fond of them and but they need disco balls. That's my gripe. My biggest complaint is they 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.

• 1:04:28Molly O'Shea?

  How did you get into SpaceX?

• 1:04:30Speaker 01

  Ah, how did I get into SpaceX? Luke Nosek.

• 1:04:33Molly O'Shea?

  Okay.

• 1:04:33Speaker 01

  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 Banister 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 and before you go to Silicon Valley. So Scott and Luke basically came out west together and they had walkie talkies because there's no cell phones at the time. I've got a fun picture of this, by the way.

• 1:05:13Speaker 01

  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 the 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

• 1:05:57Speaker 01

  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 ask me is, "What's it like to meet Elon?" And I'm like, "Well, I only see him at weddings."

• 1:06:13Molly O'Shea?

  Really?

• 1:06:13Speaker 01

  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.

• 1:06:19Molly O'Shea?

  Oh, my God.

• 1:06:20Speaker 01

  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, 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, "Banister, 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."

• 1:06:58Molly O'Shea?

  Oh, my God.

• 1:06:59Speaker 01

  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, "He'll 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?

• 1:07:43Speaker 01

  And so Luke and Scott convinced me to put everything that I made in Ironport when we sold to Cisco into SpaceX.

• 1:07:50Molly O'Shea?

  What?

• 1:07:51Speaker 01

  They basically said, if you're an able-bodied person, you're infinitely employable, you know, 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? You know? 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, you know, 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. It's completely changed the trajectory of my life.

• 1:08:33Speaker 01

  And yeah.

• 1:08:37Molly O'Shea?

  That is insane.

• 1:08:38Speaker 01

  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 fire.

• 1:08:44Molly O'Shea?

  And you didn't sell any of it?

• 1:08:45Speaker 01

  No.

• 1:08:46Molly O'Shea?

  What?

• 1:08:46Speaker 01

  No, not, not, I mean, I diversified a little bit, like, when I was at Founder's Fund, but for the most part, no.

• 1:08:52Molly O'Shea?

  Wow, I'm glad I asked that story.

• 1:08:55Speaker 01

  Yeah, it's a good one.

• 1:08:57Molly O'Shea?

  What did that, what did that teach you about risk?

• 1:08:59Speaker 01

  What did it teach me about risk? Well, you know, a lot of people already know my background story. I, 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, you know, the S and 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

• 1:09:41Speaker 01

  high-risk startups because the alphas there and they started 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

• 1:10:22Speaker 01

  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, 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

• 1:11:05Speaker 01

  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.

• 1:11:23Molly O'Shea?

  Today's episode is sponsored by V C X by Fundrise, the public ticker for private tech, allowing investors of all sizes to invest in venture capital. Learn more at getvcx.com.

• 1:11:37Molly O'Shea?

  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. Here's how it works. You type in an idea like AI-powered supply chain companies with positive free cash flow, or defense tech companies growing revenue over 25% year over year. Public's AI then dispatches a swarm of agents that scan every single US stock, evaluates them, and instantly builds a custom index around your thesis. What really stands out is how clearly it explains why each stock is included. And before you invest, you can even backtest your idea against the S and P 500. So you're making decisions with real context, not just guessing. And beyond Generated Assets, Public lets you invest in stocks, bonds, options, crypto, all in one place.

• 1:12:23Molly O'Shea?

  They'll even give you an uncapped 1% match when you transfer your investments over from another platform. If you want to build a portfolio that actually reflects your thesis, visit public.com/sorcery. Paid for by Public Investing. Full disclosures in the description. Founders scale faster on Deal. Set up payroll for any country in minutes. Hire anyone, anywhere. Get visas handled fast and get back to building. Visit deal.com/sorcery. That's D E E L dot com slash sorcery. So 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?

• 1:13:01Speaker 01

  Oh, gosh.

• 1:13:03Molly O'Shea?

  There's no, there's no favorites, but yeah.

• 1:13:05Speaker 01

  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, and also industrial diamonds for cutting. And, you know, 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 use to fund the company. And they couldn't see past that. They were just like, you can only sell so many diamond rings. You know, 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.

• 1:13:50Speaker 01

  And seeing the AI and crypto was coming, which the founder saw. And so I think, you know, those three are probably my most exciting investments right now that are inflecting. But obviously, there's a lot of really smaller investments. Like, 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 a Labubu. But it's going to be actually useful, rather than this 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.

• 1:14:35Speaker 01

  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, you know, 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's going to change. If we can somehow work out our stuff with China, manufacturing will come back. Bi 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

• 1:15:19Speaker 01

  that company. I've had many pitches. None of them have panned out yet. What else am I excited about?

• 1:15:28Speaker 01

  Yeah, I think those three, I mean, bringing, bringing a computer, like,

• 1:15:34Speaker 01

  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.

• 1:15:48Molly O'Shea?

  Deep tech is cool.

• 1:15:49Speaker 01

  Yeah, it's very cool, very hard, but very cool.

• 1:15:52Molly O'Shea?

  I mean, you, especially with your track record, have been a strong proponent of America.

• 1:15:58Speaker 01

  Oh, yes.

• 1:15:59Molly O'Shea?

  And reindustrialization.

• 1:16:00Speaker 01

  Yes, from, from day one.

• 1:16:01Molly O'Shea?

  When does that consolidate down?

• 1:16:03Speaker 01

  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 a Varda, you know, for other types of startups to dream that they could even exist in that space. You know, it, 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, you know, satellites by non-allied countries collecting data, you know, and they're destroying some of our satellites. And there's this race to the moon.

• 1:16:44Speaker 01

  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, with countries that are not in our, don't have our interests. And so I think that's another reason of why now.

• 1:16:58Speaker 01

  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 battle bots is going to be a thing. And so like if you look at Anduril, for example, they have this product that can take out, you know, like a whole drone swarm in one go. We're going to start seeing things like that where, you know, 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 Anduril 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.

• 1:17:41Speaker 01

  So I think that's why now. I tend to not play in the why now space, though.

• 1:17:46Molly O'Shea?

  Yeah.

• 1:17:47Speaker 01

  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

• 1:18:31Speaker 01

  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. And so 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's 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.

• 1:19:09Molly O'Shea?

  So is that Cyan's secret to success?

• 1:19:11Speaker 01

  Yes, it should be all seed funds' secret to success, but it's not really.

• 1:19:16Molly O'Shea?

  So as we close out, I like to do our Brex question. So Brex is all about performance. Spending's faster, 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 mentored you a long time or inspired you. So for you, who are like a couple people, maybe one or two that have inspired you?

• 1:19:42Speaker 01

  Well, Peter Thiel, obviously, Mark Andreessen.

• 1:19:49Molly O'Shea?

  Despite.

• 1:19:49Speaker 01

  The two of them probably would not want to be in the same sentence together, being heralded, but Peter Thiel, hopefully it's obvious to people why I love him. And, you know, he was my partner for four years at Founders Fund. And I always liked 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.

• 1:20:23Molly O'Shea?

  Why do you think that?

• 1:20:25Speaker 01

  Because he's inaccessible, because he does weird things that are, that no one can predict, because he thinks really long, and he's also operating a thousand feet above everybody else, right? 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 cover of magazines. And what he, basically, he was, you know, the Netscape was his thing.

• 1:21:08Speaker 01

  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 gonna meet that guy someday. I'm gonna, I'm gonna sit in a room with him and he's gonna ask me a question and he's gonna value me. And I didn't meet him until that was true. And so, you know, I wouldn't say he's a mentor actively, but he's a, my mentors are far off. I like, you can learn a lot from people without ever knowing them, by just by watching them and observing them. And kind of like a meta-game in Mafia. You know, 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.

• 1:21:53Speaker 01

  And maybe you'll be in the same room with him someday, but for the most part, he can 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? You know, 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.

• 1:22:21Molly O'Shea?

  Okay.

• 1:22:22Speaker 01

  He's definitely one of my heroes. I love him. I've never met anybody in my life with more executive function.

• 1:22:29Speaker 01

  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.

• 1:22:55Molly O'Shea?

  Ooh.

• 1:22:57Speaker 01

  It is my dream, I'm gonna put it out in the universe, that I get to meet Rick Rubin someday, because 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.

• 1:23:21Molly O'Shea?

  I hope you guys meet.

• 1:23:23Speaker 01

  I hope so too. I really, really want to meet him.

• 1:23:25Molly O'Shea?

  He has a podcast. Why don't you go on it?

• 1:23:27Speaker 01

  I know. I don't know how to reach him. I don't know how to reach his team.

• 1:23:29Molly O'Shea?

  Really?

• 1:23:30Speaker 01

  I just keep putting it out in the universe and I figured it'll eventually happen.

• 1:23:33Molly O'Shea?

  Okay. We'll put it out right now.

• 1:23:34Speaker 01

  Yeah.

• 1:23:34Molly O'Shea?

  Tetra Gramaton. Or I hope I said it right.

• 1:23:37Speaker 01

  Yeah.

• 1:23:37Molly O'Shea?

  But you made a really hard word as your podcast name. Cyan needs to come on.

• 1:23:42Speaker 01

  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.

• 1:23:49Molly O'Shea?

  Oh.

• 1:23:49Speaker 01

  Hey.

• 1:23:50Molly O'Shea?

  Hey. That's the source.

• 1:23:52Speaker 01

  Maybe that'll get me on. I don't know. We'll see.

• 1:23:54Molly O'Shea?

  That's exciting. Okay, we'll put that out in the universe.

• 1:23:57Speaker 01

  Yeah. We'll put that out in the universe.

• 1:23:59Molly O'Shea?

  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, like.

• 1:24:26Speaker 01

  Go to events. Take the picture. 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, you know, 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? Like, you can be curious and for a place that like 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.

• 1:25:11Speaker 01

  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.

• 1:25:30Molly O'Shea?

  Yeah.

• 1:25:31Speaker 01

  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.

• 1:26:05Molly O'Shea?

  Yeah.

• 1:26:06Speaker 01

  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 going to 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...

• 1:26:25Speaker 01

  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. We call everyone a [bleep]. How are we going to find the real [bleep]? 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 going to change. And if it gets me canceled, I really don't care.

• 1:27:01Molly O'Shea?

  That was a banger. You do eat Mars babies.

• 1:27:04Speaker 01

  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.

• 1:27:10Molly O'Shea?

  No, that was hilarious.

• 1:27:11Speaker 01

  Because if they stop and think about it, there's like, there's no babies on Mars. Yeah, because 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.

• 1:27:23Molly O'Shea?

  Let's go.

• 1:27:24Speaker 01

  He's like, "I've [bleep] 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 a... 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.

• 1:27:52Molly O'Shea?

  Yeah.

• 1:27:53Speaker 01

  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.

• 1:28:29Molly O'Shea?

  That's amazing.

• 1:28:30Speaker 01

  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.

• 1:28:41Molly O'Shea?

  And this is why you must follow Cyan on X.

• 1:28:44Speaker 01

  Thank you.

• 1:28:45Molly O'Shea?

  And on Mafia. Hopefully, there's a next one.

• 1:28:47Speaker 01

  Yes, hopefully, there's another season. I don't know if I was interesting enough to come back, but we'll see.

• 1:28:50Molly O'Shea?

  I don't know. Silent killer over here.

• 1:28:52Speaker 01

  I'm a silent killer.

• 1:28:55Molly O'Shea?

  Thank you, Cyan.

• 1:28:56Speaker 01

  Thank you, Molly.

• 1:28:56Molly O'Shea?

  This is awesome. 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.