Cyan Banister & Lee Jacobs Investing in the Magically Weird | SpaceX, Uber, Anduril, Crusoe

In this episode, Molly O'Shea speaks with Cyan Banister and Lee Jacobs to discuss the unique investment strategy of Long Journey Ventures, focusing on their ethos of 'Magically Weird.' Their investments include breakout companies like SpaceX, Uber, Anduril, Crusoe, Notion, DeepMind, Loom, Postmates, and more. We explore how they build a community of independent thinkers, create memorable events, and foster authentic connections among founders. "We're looking for misfits, free thinking people." - Cyan The conversation also goes deep on the rise of spirituality, the importance of aligning profit with purpose, and the shift in venture capital sentiment, highlighting the cynicism among founders and investors. The dialogue culminates in reflections on the future of startups and the significance of community and shared values in achieving meaningful success. Molly on X: https://x.com/MollySOShea Cyan on X: https://x.com/cyantist Lee on X: https://x.com/LeeJacobs Follow Sourcery for the latest updates! https://www.sourcery.vc/ TIMESTAMPS:

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

• 0:00Molly O'Shea?

  Well, hello. Hi, Cyan. Hi, Lee. It's great to have you on. I think this is an exclusive. I don't know if I've seen both of you on a podcast before, but I'm so happy to have both of you here. We're hopefully gonna have the full Long Journey team in the future, but this will be a really fun conversation.

• 0:19Speaker 01

  Yeah, I thought it was a great idea. No one ever asked us to do both of us. And I was like, yeah, let's do it. Because Cyan and I have a really fun and history and fun relationship, and hopefully that'll come across today.

• 0:32Molly O'Shea?

  So I want to dive deep into Long Journey's unique strategy. You've built out a brand, a community, and to start, let's really break this down into what the magically weird is. Lee, what is the ethos behind magically weird?

• 0:49Speaker 01

  Yeah, great question. You know, when we look back, a few years ago, we look back at sort of like, what are the best investments that I had been a part of? And I don't say at the time, what had she had been a part of, what had her husband Scott been a part of, what have Naval, who I used to work for at Angelus? And there was never any theme of like, it was really a hot space, or, you know, it was a hot round, or, you know, it was any particular theme. The only thing that really kept coming up was that the company looked quite weird at the time. You know, Cyan likes to tell the story, which I'll let her tell, but when Uber got started, who was going to get into other people's cars? The black market, the black car market was really small. This is not a thing.

• 1:33Speaker 01

  Niantic is a good example of, you know, there's going to be Pokemon walking around the streets of San Francisco. That sounds a little nuts. When Creo Show got started, they're gonna do, they're gonna mine Bitcoin in the middle of North Dakota with like, fire that comes out of the ground? That sounds a little insane. So we've really honed in on what we think great companies look like at the time in which we invest, which is the pre-seed and seed. We think they look quite weird at the time. So what that manifests in is it can be frontier, kind of weird looking things, but we also do, you know, magically boring businesses run by crazy people. And that itself is a weird thing to do, to actually want to work on something like government RFPs. Why would someone want to do that? Well, it has to be kind of crazy and weird to do it.

• 2:16Speaker 01

  And that, I think, creates its own defensibility. So yeah, that's what magically weird means to us. And yeah, happy to go into it further if you want. Cyan, do you want to add anything to that?

• 2:28Speaker 02

  Yeah, I mean, I think it's a siren call as well. You know, we, we only, not only did we notice it, but we started realizing that we want to be a home for these people. So that when they, they realize they're going out and pitching people and people just aren't getting it. You know, if you've pitched a 20 VCs or angel investors and they're like, I don't quite understand what it is that you're building, or it's too soon, or it's a lot of things. We really love that phone call. We love getting the phone call of, you know, another VC calls us and says, I just got this weird thing that landed in my inbox and it seems interesting, but I don't understand it. I think you guys will.

• 3:05Speaker 01

  And I think Cypher is a very good point. It's, it's, we're looking for is that a little glimmer of intuition that someone has where they're like, I think this is interesting, but I'm not sure I can, I can express it or I'm not sure I can tell my friends or I'm not sure I can tell my boss.

• 3:20Speaker 01

  Those things tend to be the things that are really interesting. Cause if it was easy to talk about, or if it was something that everyone's going to like, by definition, it might be consensus or it might be actually, you know, it might be a, be too obvious an idea. If it's something that you have an inkling on, that you have a feeling about, we pay attention to that. So yeah, we're looking for things that other people are not really paying much attention to.

• 3:43Speaker 02

  How are you finding them? Oh, gosh.

• 3:46Speaker 01

  All different places. I think, um, yeah, I mean, Cyan has had so many interesting stories. We've all had great ways of finding companies. I think, um, one thing that I think is true is that we've really built a brand for doing that kind of thing. I think people, I actually have an inbox, I looked at my email five minutes ago and there is an email that says, I have a weird one for you. I mean, that is, that happens quite a bit these days where people are like, you know, the only people we can really think about sending this to is you guys. And then when you invest in these people that are really independent thinkers and they end up in interesting companies and start great things, they tend to have friends like that. And so it really compounds on itself.

• 4:26Speaker 01

  So you kind of get into the game of these independent type of founders that are doing out their things. And then they also have other people who, you know, frankly, those people can be lonely. And if they, they find friends and other people like them. And so that really, that really compounds itself.

• 4:41Speaker 02

  And I think through events is another big way that we do this, you know, it, coming back to the compounding nature of this, once you, we have a flock, if you will.

• 4:52Speaker 02

  Well, we're part of the flock, but we have this flock of people that we, you know, we gather and we get together and we have events and, and, you know, we invite others into it and people get to see what our values and our mission are and live them. And that sort of thing radiates and just compounds over time.

• 5:11Speaker 01

  I like to say, we're never going to do an event that's like a boring AI event, where it's like seven VCs and two founders and your job is to like, talk about the future of AI. And someone's like, oh, I was going to do this. And it's just, everyone's been to those dinners and they suck. We want our events to be memorable. And we're really trying to put people in a position where they are comfortable to be themselves. Because I think founders are looking to work with people that they want to build long-term relationships with. And the only way you get to do that is to actually be a set, create a setting, people can be authentic. And then the other side, if you're really looking for things that other people aren't going to find, you need to know who these people are. Because if they're just going to say what the future of AI is, they, it's not a great way to get to know someone.

• 5:55Molly O'Shea?

  I have to admit, I think you guys are drumming up some demand and some FOMO for these events, because I keep on hearing about these dinners from multiple people all over the country. So you're definitely doing a really good job there, creating unique atmospheres for people to get to know one another. But I want to know, like, what is the recipe for this event? Like, how do you construct these unique dinners or community building efforts where people can be themselves and not just talk about what's ever happening in AI land?

• 6:29Speaker 02

  Yeah, I'll happily take this one. When Lee and I founded the firm, we sat down and talked about all of the things in our careers so far that we didn't like, and that what we wanted to be different about. And one of the things I hate more than anything, and Lee does too, is going to these network events where you're walking around with your drink and you come up to someone and you're like, and it's the same question over and over again, which is, what are you excited about? And I remember Peter Thiel once told me, he said, when someone says, what are you excited about? It's because they don't know what to be excited about themselves. And so they're fishing you to try to get excited about something because they lack

• 7:11Speaker 02

  it in their lives. And, and so they're doing, they're outsourcing their work to you. And so he asked, what are you upset about? You know, what keeps you up at night? What worries you? And so we, and I really like that. And I really like that about, about Peter and one of, one of the things I learned from him. But we started thinking about, okay, is there a way that we can build our firm that's values driven, but also have events that when we invite people to them, it really aligns with our values, but it's also super fun, so fun that you don't even feel like you're working. But at the same time, when everybody leaves this event, they're like, what the heck did I just go to? That was

• 7:53Speaker 02

  so amazing. I made, I made a good friend. I, I found a co-founder. I came up with an idea I never thought I would have before, and I solved a problem I didn't even realize I would solve it. So how you do that, and you know, we, we figured we got to bring somebody in to help with this. And so we brought in Mike Wing. And Mike Wing is an amazing experience designer. And he, he calls these recipes, you know, every time we do one of these events, he comes up with a recipe. And he's taught me this language, which I really love, which is every event has ingredients, just like in making a soup has ingredients, right? You have your broth, you maybe you have carrots or onions or whatever. And every

• 8:35Speaker 02

  event that you normally go to has these base ingredients, but what they don't do is spice it up a bit or make it much more interesting so that you remember it as the best soup you've ever had in your life. And so we have all the key ingredients, but what we do is we say, okay, instead of it going this way, what if we turn it on its head? What if we, you know, eliminate small talk? So from the very get go, we're like, do not walk around and do this. Instead, we're going to give you a prompt. And this prompt is going to open you up in ways, for example, we had a dinner one time that talked about superstitions. And we went around the table and people confessed all their superstitions. And what was really interesting was that everyone had one. And some of them were fascinating, absolutely fascinating.

• 9:18Speaker 02

  And, um, and then there was games that we play at these dinners and there's a lot of things that we do. And at the end, people are disarmed and authentic. So the authenticity comes out. People are, you know, able to be themselves. Uh, we're able to surprise and delight them. And then most importantly, we show them a different way of living. And they can then steal that idea. We want people to steal the ideas of they come to one of our events and they see something and they're like, wow. I want to do this with my team at work or I want to my next offsite retreat to be like this. By all means, do it because that's why we do it is we're trying to show companies, founders, um, colleagues, LPs, that there's a different way that you can live life.

• 10:01Speaker 02

  There's a different way that you can conduct a business in that you really truly enjoy it. And it lifts your spirit and it makes you excited to do what you do every day. And you make meaningful connections and meaningful memories out of it. An example I like to give is we did this movie screening and this came about because Mike and I and all of us were riffing on this concept of free will. And we were wondering like, you know, everyone's talking about whether we have free will or not. Well, how do we express that? Do we write a blog post? Do we get on a podcast? I was like, why don't we have a movie festival and start showing movies that, you know, discuss the concept of free will and leave it kind of up to them. But if you just do a movie screening on its own and you hand out popcorn, then you're in the land of boring again. Right?

• 10:45Speaker 02

  So the first one that we did, right before the movie started, we had a second screening. Uh, where right before the movie started, we said, well, in order to discuss the concept of free will, we're going to give you an option B. You didn't even know existed, which is you can stand up right now, leave this movie, go to a theater that's a little outside next door, where you're going to see a movie that you have no idea what it is. Um, but we're going to vote on it. So when you go over there, we're going to hold up some movies and we're going to vote. And so the first movie was Arrival and I showed up in an Arrival suit, wearing the contamination unit outfit. And, um, but then I left the theater and what was interesting is about 30 people got up and went with me.

• 11:29Speaker 02

  And we ended up watching the game. And two separate conversations happened in both of those rooms that were equally as important, but right for the right people that stayed in them and it had a profound impact on some people and they're still talking about it to this day. And then the second one was The Matrix, which is a classic one. You know, if you're talking about free will. And right when Neo is about to take the red or blue pill or make the choice when Morpheus hands those pills over, we stopped the movie. We brought the house lights up a little bit and then a phone on the stage that was a rotary phone started ringing. And our idea was to let it ring and ring and ring and ring forever if we had to until somebody answered it. And then the person who answered it, they were given a choice, which is you take the

• 12:14Speaker 02

  blue pill, you go back to your seat, you eat your popcorn, life goes on as normal, you watch The Matrix, that's what you came for. Or you take the red pill, you gather all your things, you leave the theater and you're going to go to some undisclosed location and you have no idea what's about to happen. And this guy didn't hesitate and he said, red pill. He's like, can I bring my wife? We're like, yes. And so outside, we had a limo where we swept him away to a one-star Michelin pop-up experience that only existed for one night where he got to eat Chinese-Mexican Michelin star food. And what was really, really fascinating about it was just before he ran up to the stage,

• 12:55Speaker 02

  he said to his wife, they were discussing what an NPC is. And he said, am I an NPC? And she said, no, you're not an NPC. And he's like, well, what is an NPC? And she explained it. And he said, you know, if an opportunity arrives in the world, I'm going to answer the call.

• 13:09Molly O'Shea?

  Oh, my God.

• 13:11Speaker 02

  Exactly. So he did just that. And these are the types of, you know, afterwards, he told us it was one of the best nights, if not the best night of his life. And if you can do that for somebody, if you can give somebody the best night of their life, you know, that's far more important than than just an event. Right? Like you've changed fundamentally changed someone's life and the perspective of how they can have fun and how they can engage with people. Like now this person and I text back and forth and I didn't know him before this. This was somebody we invited that spoke at an event previously and we were not friends yet, but now we're friends and we have a meaningful connection. Whereas before, had we gone up to each other and just clinked our glasses together?

• 13:56Speaker 02

  It wouldn't have been that meaningful, but now I know more about him and his wife and his family and his plight in this world because we had that intimate moment of realness where we were hyper-present with one another.

• 14:07Speaker 01

  Our strategy is just to make more friends.

• 14:09Speaker 02

  Make more friends. We just want to make more friends.

• 14:11Speaker 01

  Yeah, make more friends. Yeah.

• 14:13Molly O'Shea?

  Yeah, that's incredible. That is an incredible story. And I love the questions getting, I love getting asked questions like that, like really abstract, but like kind of goofy, not really goofy, but they're just, you wouldn't expect it, kind of questions, dinners or work events, whether it's superstitions or like phobias, and then you're just going around the table and you're like, I had no idea you had a phobia of like candles. That's crazy. You know, simple things like that, but it does, it helps break down the barrier and like get, get down to your more creative self, which I think is really important.

• 14:50Speaker 02

  I do have a phobia of candles.

• 14:52Molly O'Shea?

  Oh.

• 14:53Speaker 01

  Really?

• 14:54Speaker 02

  Yeah.

• 14:54Speaker 01

  New facts from Cyan today. I write that one down. I keep a list of things that are very special about Cyan and that's going, it's going in there.

• 15:02Speaker 02

  Yeah, people keep asking me, why do I have any candles? It's because I, it's funny you should bring that one up because that is my number one phobia, candles.

• 15:10Molly O'Shea?

  Oh, gosh.

• 15:11Speaker 01

  Can you explain, is it about starting a fire or?

• 15:14Speaker 02

  Yeah.

• 15:14Speaker 01

  I'm sorry for, I'm interviewing our, my apartment.

• 15:17Molly O'Shea?

  Yeah, no, go for it.

• 15:19Speaker 01

  Yeah, yeah, yeah.

• 15:21Speaker 02

  It's because when I was little, I was told this story about how my mother accidentally set her house on fire playing with candles and it caught a curtain on fire, on fire. And, and so it got really drilled into me that candles are dangerous and if you don't mind them, the bad things can happen. And so I have not kept candles around ever since and I don't like being around them and I don't, it's like, I know where it came from and I know, I know that if you tend to a candle, it's not going to light your house on fire. Like I can understand the logic behind a safe candle. I just don't keep any, if anyone gives me one, I give it away immediately.

• 15:57Molly O'Shea?

  Fireplaces, matches, lighters, where does fire stand?

• 16:03Speaker 02

  Yeah. I mean, I have a fire stove, but I'm, I'm, I tend to it, right? Like you have to be very mindful and present with a stove. You can burn a house down with stove. So I, I don't like lighting fireplaces. I don't like. I just think fire belongs in certain settings and I try to keep it away from me.

• 16:22Molly O'Shea?

  I respect that. Lee, do you have any phobias you want to talk about?

• 16:25Speaker 01

  Um, ah, man, I don't.

• 16:28Speaker 02

  Pros?

• 16:29Speaker 01

  I don't think I have any. Oh, well, a good one. Yeah. Yeah. So I was walking in Austin with Ariel, our other partner, about a year and a half ago, and we had just met a pretty well-known founder. And, and we were just talking about that and that was really interesting. And a crow landed on my head out of nowhere. And I, and the way that I experienced it was I felt this weird thing. And then I looked at someone who was looking, walking towards me and they were just like, what, what's going on? They were shocked. And then I realized that this crow just came on my head and fell off. And of course, Ariel, who I love, all she could do was laugh. She wasn't going to help me. There was, she wasn't like, hey, there's a crow on

• 17:14Speaker 01

  your head. She just started cracking up and watched this crow on my head. So I have noticed that in the last, you know, ever since that, there are crows all over the place and they're always kind of following me. I think my, I have a number of theories. I think it's because I, I once heard a pigeon a long time ago by throwing a pen at it. It was in an area that it shouldn't have been and it hit, it hit the pigeon and the pigeon wasn't very happy. And pigeons and crows are friends, like everyone knows. And I'm just dealing with that. So anyway, it scratched the top of my head. And, um, you know, there's a theory could be thought that it was my hair's a nest. We don't know. But a crow did land on my head. So that is a first time telling that story publicly. So.

• 17:59Speaker 02

  I got the text message right afterwards and I was like, what is going on?

• 18:04Speaker 01

  Yeah, it's so ridiculous.

• 18:06Molly O'Shea?

  Might be good luck. Could be impressive. I don't know. Maybe it's your spirit animal.

• 18:11Speaker 01

  Yeah. Well, now that it's out there, maybe someone could tell me what they think it means.

• 18:15Molly O'Shea?

  Yeah. Let us know. Comment and let us know what the, what the crow means.

• 18:20Speaker 01

  Yeah, that'd be good.

• 18:21Molly O'Shea?

  Well, I love that. So the strategy, the, the, the strategy and the branding around magically weird. You know, I was thinking about this. It's like, marketing, you know, it attracts things. You typically draw in people from all these different places. So what does magically weird attract? Like, what does that look like? And how does that come together?

• 18:44Speaker 02

  Yeah, I mean, we're looking for misfits, free-thinking people, people who didn't fit in in a company. You know, they couldn't be employed. Like, a lot of, I forget what Breck says, but he says, what did he say? He's never been hired, only been fired?

• 18:59Speaker 01

  It's something like that, yeah. That's actually true. Yes, exactly. Yeah, that's right. He's only been hired.

• 19:04Speaker 02

  Because every company he's ever built that he's been acquired, he ends up like, and there's certain traits to a founder, right? They're, they don't fit in places for a reason. They think about the world differently. They think about, you know, they're not trying to fit in, they're actually trying to break things in and or remold things to this vision that they have. And so, you know, I think that every fund has its own flavor. I mean, I don't know if you ever watched Mad Men? Did you ever watch Mad Men, the show? Might be too long ago. But there's this one episode where they talk about, they talk about the cigarette company that they're trying to brand, and they say that, you know, all cigarettes

• 19:46Speaker 02

  at that point are fungible. And they say, well, we're gonna call your cigarette toasted. Well, if you think about it, all VCs are kind of, we have money, it's the same, right? It's not, the money's not different. So what makes us stand apart is our ethics and who we are and what we stand for and our, our compass. And then the siren call that we're putting out for the types of people we want to show up at our doorstep. And so we're looking for people who are really, really independent thinkers that are dreaming big in ways that are gonna reshape humanity, you know? If you look at Airbnb, the founder said, you know, people are gonna sleep on strangers' couches. And everybody said, well, you're insane. You know, those are the types of people we want. You know, the people who

• 20:30Speaker 02

  just have this insight that whatever it is that they're gonna work on is gonna change how everything's done. I mean, you think, maybe you could talk about Chase, like when he showed up at your door and tried to convince you to go to South Dakota and jump on a plane with him to harness energy from Gas flares, like what did you?

• 20:50Speaker 01

  Yeah, yeah, it's I don't know how much people know about the business Prusso. It's an AI data center business at the moment, but when it started, he showed up. Yeah, we had a nice conversation at Dan Deline Talklet and he basically was like, I, there's all this gas that comes out of the ground in places like North Dakota, and it's wasted and it's burnt away and it's in these huge fireballs. And there's, so that's one problem. And the other side of it at the time, since 2017, 18, Bitcoin was just kind of continuing to ramp up and was very energy intensive. And it's a huge problem for the industry. And so he was sort of in, it was at Polychain at the time.

• 21:35Speaker 01

  He grew up in with a friend that was in the oil and gas industry and he kind of learned about that, the flaring issue. And so he was like, yeah, I took a, basically like a truck with a bunch of servers and moved them out into the middle of North Dakota and started mining Bitcoin in like oil and gas world. And everyone in the oil and gas world was like, what are these crazy nerds doing? And then no one in the crypto world was like, oh, it seems like a great idea. I'm going to put some servers in, you know, the middle of North Dakota and see what happens. So I remember thinking, that's one of the more absurd things I've ever heard. Like, tell me more. And so that's a great example of, you know, the kind of thing we look for, which is often something you've never heard before. It could be easily dismissed. It was certainly dismissed at the time.

• 22:19Speaker 01

  But if you look past and you're willing to like, really think about what, why is this person so excited about it? What's actually behind there? You can, you can discover secrets. And then the follow, the other piece of that is actually something that I really, really respect Cyan for is willing to stick your neck out for things when, even if it's not popular. And so I think that's a big piece of what we do at Long Journey. We're willing to put our neck out there and it's a reinforcing thing. We encourage each other. If you believe in something and we want to, we want to support everyone to do that.

• 22:52Speaker 02

  Yeah, the other thing is we're looking for people that this is their life mission. You know, maybe they had a certain type of upbringing or they grew up in a certain region of the world that impacted this decision that gives them a unique insight that nobody else could have. You know, that that's the boat.

• 23:08Speaker 01

  Totally. And which ties back to what we were talking about earlier with the events, which is you put people in these experiences, these moments where they can, you can really understand, as you said, Molly, like these creative moments and they're thinking about things creatively, you can see inklings of like what it is about for them. And often those things that when they're relaxed and they're thinking about something interesting, there's often a tieback to like what is they're doing and why they're working on that thing. And those are the things you want to discover, not just like, hey, I've got a business plan and I'm gonna go and sell SASSRA, you know, things, it's gonna be $9.99 and people are gonna love it. Like, everyone says that. There's no alpha in that. You're looking for like, what's, what's a little interesting, what's a little out there about what's going

• 23:51Speaker 01

  on? You can only figure that out if you put people in a good, in a good environment.

• 23:55Speaker 02

  Yeah, that's true.

• 23:56Molly O'Shea?

  Absolutely. And that's, that's so important at the earliest stages too, when story is, is probably one of the number one driving factors of why things get funded, founders and the story. And for Long Journey Ventures, you guys have evolved from early stage to later stage too. I'd love to unpack more of the originations of the fund and what that looked like, what that looked like to today.

• 24:25Speaker 01

  Yeah, sure. Yeah, I mean, I, I think about it as like, we want to have as the biggest impact as, as we can, but we want to grow in an organic and responsive way. And, you know, we're, as Sane said, we're very values oriented and one of our values is it's not monopoly money. And so, the origin of kind of going from super early stage, which is never going to change, we're always going to do that and be a big part of what we do, from doing more follow-on checks at slightly later stages, is we saw a lot of our companies mature. The Crusoes, the Flock Securities, the Andorals, the Diamond Foundries, all these things that we, we continued to, you know, very early on, and, and continue to have

• 25:10Speaker 01

  a good relationship with. And we saw that there were still, they were still misunderstood. They were still magically weird, even after raising. Using a series B or C, so they were still alpha there. So initially, we just, in my roots at Angelus, you know, I did the first Angelus Syndicate and did a lot of SPVs. I knew that there was this mechanism which we could start investing in some of these companies that were not pre-seed and seed, but we still thought there was a lot of upside in. So we started doing, in 2020, when I found the fund, we started doing some SPVs in some of these opportunities. We did Anduril in that period and a few others.

• 25:47Speaker 01

  And as that strategy grew and it started working and those companies went on to, you know, continue to grow, we designed a strategy and a fund around it. But what it wasn't, it wasn't like, oh, we're going to raise like a $200 million fund. We think there's all these, we can do this strategy and we'll just, we'll just try it. You know, it was more a very thoughtful and meticulous way of building this thing out. And that's kind of how we've grown AUM in that direction and that's why we've done it. We want to, we want to continue to support the businesses that we really believe in and think we have a really incredible strategy for them. Ariel was a huge part of that too, and she brought her on.

• 26:26Speaker 01

  You know, she had a traditional background at Co2 and Kleiner and was used to writing those slightly later stage checks than we are.

• 26:34Speaker 02

  Going back to the origination story, Lee and I's roots are in angel investing and we both met at Angelus. We're both Angelus alumni. And, you know, we had a remarkable time there together and that's how Lee and I started collaborating at first, which was, you know, how do we solve this problem where we can make access available to people for deals that they didn't previously have access to? We both wanted to serve this higher calling. One was him to find the next emerging fund managers. But most importantly, at the end of the day, was to share the deals with other investors, other angel investors, who, who maybe they're not, they're just getting started and they could write micro checks.

• 27:17Speaker 02

  But micro checks, as we know, add up into larger checks. But we also knew that founders didn't want to deal with all these people on the cap table. And so Naval had this Brilliant. And all of the engineers there had this brilliant insight that they could build a platform around this. And I was angel investing at the time. And I decided, you know what? I want to share my deal flow. I want to go join Naval and help him. Build this. And that's where we met. And then when I went on to Founder's Fund, Lee and I collaborated a lot. And the only deals that really stood out when I was there that were differentiated from everybody else's were coming from Lee. And, you know, he was sending.

• 27:56Speaker 02

  Whenever there's a wave and there's a consensus wave, you get all of the same things. So like, right now, the consensus wave might be. Defense or AI. And so you're going to get a lot of stuff coming in. Like, you'll notice the weird ones that come in that aren't out of central casting. And you're like, what is that? And that was Lee.

• 28:16Speaker 02

  I'm going to bring in these companies from Brazil. No one was looking in Brazil at the time. And he was bringing the best companies from Brazil to us. Or I'm going to bring Crusoe, you know, this, this gas flaring business or Mindbloom. Or, you know, the list just goes on and on. Modern Animal. And it just, these were not companies that were coming our direction. And so some of our best deals at Founder's Fund came from Lee. And so when I left and I wanted to do something different, I just thought that I can't think of anybody better to work with. And so I reached out to him and he was like, duh.

• 28:53Speaker 01

  That's my, that's my exact quote. I was like, duh. Well, I, I had, we had this great energy and I just, um. I thought that there was, there was a world in which we would work together and it was really, um. An honor and she asked, but I kind of like. I, I, I knew it was gonna happen and I'm glad it has. It's been such an incredible journey and we're, uh. Yeah, we're just getting started. I mean, it's been. About almost five years of working together formally, but more and more.

• 29:23Speaker 02

  Our fund, One Together is fun too. We had a micro fund and had already established Long Journey by the time I joined and, you know, so if anything, he had momentum going already and I got to hop along on the ride of the momentum. But, uh, but it was a great time to join because we got to sit down and really put our heads together and think about how we wanted to build this and build the firm of our dreams that we want to show up to every day. And that makes us proud of our work and what we do.

• 29:53Molly O'Shea?

  It certainly seems like you guys have known each other for forever. Like there's there's real compatibility there.

• 30:01Speaker 01

  Yeah, well, I don't know. Do you believe in other lives? Maybe we were friends in other lives too.

• 30:06Molly O'Shea?

  Maybe you were just two crows.

• 30:08Speaker 01

  There you go. Huh. Yeah, yeah, yeah. Well, now we're now we're transitioning. I know you want to talk about spirituality. So maybe that's the easiest way to do it.

• 30:18Molly O'Shea?

  Should we go right into spirituality now?

• 30:20Speaker 01

  It's your call. It's your show, Molly. You get to decide.

• 30:23Molly O'Shea?

  You're right. Thank you. Okay, yes. So let's go into that because I think that it's it's very aligned with our conversation in general, whether it's bringing people together or like thinking of something different, just being a part of something. So spirituality has been taking a shift in Silicon Valley. Maybe it's more than Silicon Valley, but here I am in my echo chamber and I'm seeing, you know, Trey Stevens and Gary Tan, and I'm seeing the El Segundo crew as well, taking on different meanings of bringing back spirituality. So what does this mean for you guys? And what have you noticed?

• 31:03Speaker 02

  Yeah, it's a nationwide trend. It is not just in Silicon Valley. I think I saw a statistic the other day that Bible sales are on the rise by like 28% and most of those are first time readers. And I think what happened is the pandemic. You know, there's two types of people during the pandemic. There were the people that were first responders who had to get up in the morning and go to work and work through it and be in the public. And they dealt with their own kind of suffering and trauma as a result of that. And then there's the second group, which had to withdraw from the world and hide. And that was also traumatic in its own weird way. And so I think everyone had to reflect on that period and wonder how, okay, one, you have to ask yourself, if there's a God, how could a pandemic happen?

• 31:49Speaker 02

  How could we be in this position to begin with? And then you start asking all kinds of questions, which is, you know, why do we exist? What is the meaning of life? What is my purpose? And the list goes on and on and on and on. And not everybody just became a bread maker, you know? Like, a lot of people, you also saw these people learn how to make bread or fire up pizzas or whatever, and or start a garden or... But I think people unplugged for a period of time or disconnected from the world that they knew for long enough that they actually started to let something inside that they'd never let in before. And that was the belief that there's something bigger than themselves. And so I think what we're seeing right now, and there's, you know,

• 32:33Speaker 02

  I personally believe that there is a truth, and it's like a mirror. And the mirror has fallen to the ground and there's fragments all over the place. And certain religions and certain beliefs come and they take that fragment and they build something on top of it. But they all lead up the mountain to the truth. And so it doesn't matter what flavor you pick. It could be Buddhism, it can be Christianity, it could be whatever it is. But sometimes just relinquishing the control of the ego, of the mind, that you are somehow in charge of everything and that you're responsible for everything. And moving into this mindset that there's, you're part of a greater whole or a greater cause, a part of humanity, is what people are starting to realize.

• 33:18Speaker 02

  And I'm excited, I'm here for it, because I do think that, you know...

• 33:25Speaker 02

  The other opposite of that side of the coin is to believe that you are responsible, you are, that all brilliance and everything flows through you and all of these things. And that's just the ego talking, right? It's a very ego-driven activity. And when you start destroying the ego and removing the ego is when real magic starts to happen. When you actually can see the world differently, when you can actually start to look at your neighbor differently, you know, the person down the street differently. And this is how we get and maintain world peace is through love. And some, you know, some religions don't preach love and you should run away from any religion that doesn't preach love.

• 34:08Speaker 02

  If love is not the core tenet of the religion or the spirituality practice, then I would argue that, you know, it's not the right one. But we should love one another and we should try to build things and we should try to make things that promote that. And so a lot of what I do, and I've been very passionate about this, and Leah is very passionate about it too, is encouraging every member of our team and all of the partners to have a higher purpose that they serve. It doesn't matter what flavor it is, it doesn't matter what it is, as long as it's higher than themselves. And so that's usually charitable causes, educational causes, it could be whatever it

• 34:51Speaker 02

  is, but align your profit with your purpose. And when you are, when you do that, I really honestly feel that doors just start to open for you. They just open in your favor because if there is a power out there, or if there is energy or a universe or God or whatever you want to call it, you, it's almost as if you're rewarded tenfold when you do good for the world.

• 35:14Speaker 01

  Yeah, I agree with everything Cyan said, and I'd add that while I think it is a new thing to talk about it, it is something that has been going on in the best, I'll call them endeavors, not those businesses, but the, but all of human achievement, the best human achievement is, has had this. This motivation and the singular idea behind it. I mean, in our industry, we didn't mention Chicoia. I mean, they, obviously, they're the best have done it historically for many years. If you go into their offices, you walk in, all the conference names are their LPs. It's Ford Foundation or whomever else is the sort of the causal that backed them.

• 35:56Speaker 01

  And whenever they have an IPO, the CEO of the company is on the front of the page. But there's also like, here's what this money goes towards. And it's, it becomes extremely aligning when you have that type of, call it a mission, but call it beyond your, a reason beyond yourself. Sian said, that is what I think a lot of spirituality is. And then you do good work as a consequence. You know, I'd be interesting to, I can't really do a counterfactual of this, but after the giving pledge, and Sian turned me on to this a few years ago, you know, that basically all of these billionaires basically said, we're going to give X percent. I think it's more than 50% of their wealth.

• 36:38Speaker 01

  There's a pretty strong correlation between those, a lot of those businesses and those CEOs continuing to build a lot of value after doing that. And I wonder, is there, is there a causal, is there a causal reason there?

• 36:52Molly O'Shea?

  It's super interesting. I was just listening to Morgan Housel on Dr. Huberman's podcast, and they were, they were both discussing this as well. The giving back and all the billionaires donating up to, you know, almost 99% of their wealth back and what the meaning of purpose is and carrying on legacy or, you know, building something for your own. And it's, it's like quite an interesting question for at least like America and capitalism, which I love capitalism, which is great. But running towards just building something for wealth or building something for meaning? Like, there's two different things.

• 37:35Molly O'Shea?

  And from founders or people I've heard that have had, that are post-exit and that just really purely built it for the wealth, felt completely empty the day after they sold it. And there was just a really clear bifurcation between the two.

• 37:50Speaker 02

  It's the same thing for musicians, actors and everybody else, right? Like, when you have your hit and then what? It's like, okay, now what? Like, I did all of this. I, because it's a game, then they, they achieve the game. And they thought that it was over, but then they were sitting there with all this money and they're like, I can only drink so many Mai Tais and sit on so many beaches and buy so many cars. You're a steward of the capital. It's not yours.

• 38:16Speaker 02

  You don't get to really die with it, right? So if anything, it's fuel for a fire. And what fire do you, you know, a good fire? What fire do you want to burn? You know, what?

• 38:27Speaker 01

  Not, not of a candle.

• 38:29Speaker 02

  Not a candle, yes. But what fire do you want to burn and what do you want your fuel to be a part of? And that, I mean,

• 38:38Speaker 02

  those, those reasons are as, as individual as thumbprints, right? Like, you know, um, for me, I'm very, very passionate about the first amendment. And most of the causes I donate to are first amendment related, or second amendment, or fourth amendment, anything constitutional. And, but for our partners, it's, it's different. And so, you know, I would advise every founder, before you start your company, think about the higher purpose that you want to serve. So that when you are finally successful and you reach that endpoint, you know exactly what that money's for. And that way you're like, yep, that was just a stepping stone to get to this bigger thing than I actually want to do.

• 39:16Speaker 02

  Which is, I want to give everyone a bicycle, or I want to solve water in Africa, or I want to solve, you know, it doesn't matter what it is, as long as it's for other people and it's bigger than yourself.

• 39:29Speaker 01

  There is, um, there was a movement, maybe 10, 15 years ago that came out, and I think it's worth noting because there can be a distortion of this concept, which, I don't know how to call it, social impact investing, or, or just a focus on, the businesses that had to be a certain way to, to terministically decide how the world had to be. And then that became the, the goal. And from our perspective, we think of ourselves as a social impacted, uh, fund because we, we do believe in businesses themselves will do really good things for the world and we are going to do good things with the. The money that we we earn, but I do think there's a distortion around if you're trying to do.

• 40:14Speaker 01

  Actually, Trey Stevens has this great chart that I think he's talked about where it's feels good. There's this quadrant, basically, and if it's like feels good and is good or actually feels feels good and might not and might and is bad. That that is actually a potentially a distortion and if it's I it's not a good business, but it feels good to do it. That actually doesn't have an impact at all. So I think you can go the wrong way if you're not careful. So that I think is worth mentioning.

• 40:42Speaker 02

  Yeah, you think almost all investing is is, you know, what was that word that you used against social?

• 40:48Speaker 01

  Social impact, social impact. Yeah.

• 40:50Speaker 02

  All all investing is it can be socially impactful and capitalism itself is socially impactful. And and I know people wanted to brand and put a flavor on it because again, it's toasted like cigarettes. But really, they're really fundamentally what we're all doing is making the world a better place if we choose to, you know, choose to do so. And so we get to choose where we put our dollars and our effort and our time. And it doesn't mean that every company that we do on the surface, when you look at it, you might ask yourself like, how is this serving the greater good? But really, you know, if we have to make this argument when, you know, I believe that we have to make this argument every time we write a check, which is how is it serving the greater good?

• 41:35Speaker 02

  And, you know, what are the ambitions of this founder and what does this unlock and what does this do? And I think when you start thinking this way, you make different decisions, you know, you. And if if somebody else might say, I don't really care about that piece when it comes to the companies. I just want to make as much money as possible so that when I, you know, I get paid, I can go do this with the money. And that's also OK, too. You know, you don't have to say that every single company that you invest in has to make a dent in the world. But but I would argue that you do.

• 42:07Molly O'Shea?

  Yeah, and that's absolutely OK. If you want to make as much money as possible, that's like totally acceptable. But, you know, don't forget to make friends along the way.

• 42:16Speaker 01

  Totally.

• 42:17Molly O'Shea?

  As we shift over to market sentiment, there is a lot of cynicism in venture capital right now on both the startup side and fundings and then also on the emerging manager side, too. So to break this down, I'd love to start up. I'd love to start on the startup side. So what are I I'd love to get your perspective on this. What are you seeing, hearing, and what do you believe to be true or not true about this cynicism out there?

• 42:47Speaker 02

  I think some of the cynicism has to do with the lack of exits. You know, we've been hearing this over and over again, but I think that's about to change potentially. Where M and A might open up in public markets, you know, you might see more companies go public than has been in the past last four years. But I think, you know, LPs are increasingly

• 43:12Speaker 02

  uncomfortable with the lack of capital returned. And so that's why you see sort of the cynicism for new emerging fund managers. And it's not that new emerging fund managers are bad. It's just that the ecosystem has not it slowed down where people are not, you know, the liquidity is not coming as fast as it ought to.

• 43:33Speaker 01

  I think that's totally right, especially for, you know, everything sort of comes down from the LP ecosystem to the emerging and emerging managers are often the folks that are quote unquote, the riskiest and the hardest to get funded. And then when there is a dried up pool of capital on one side of it, it just doesn't doesn't trickle into the emerging manager as much. And yeah, that's unfortunate. But I think these things change. It's a cyclical business. And so that's kind of how I think about emerging manager side and the startup side. I'm curious, are you

• 44:07Speaker 01

  do you feel like founders are cynical or people who are evaluating companies are cynical? What's the, what do you think, Molly?

• 44:16Molly O'Shea?

  Hearing it from all sides, I'm hearing founders are cynical. You have to be an AI company or defense.

• 44:25Speaker 01

  I see.

• 44:26Molly O'Shea?

  That, you know, it's harder to get dollars.

• 44:31Speaker 01

  I see.

• 44:32Molly O'Shea?

  Because some managers can't actually deploy any capital, all sorts of, all sorts of stories.

• 44:40Speaker 02

  Yeah, there's a lot of, for lack of a better term, zombie managers out there. Because they are able to raise, but they still have a fund. And they're still taking meetings because if you don't take meetings, then you can't get deals, right? And you can't raise more money. It gets to be this horrible cycle. Or they have to be more judicious with the money, right? Like they're, they realize they're being watched like a hawk, watching them. And so every check-

• 45:05Speaker 01

  Like a crow.

• 45:06Speaker 02

  Like a crow.

• 45:09Speaker 02

  They're being watched and you know, their performance is being evaluated more than ever before. And so they're really, really hesitant to strike on a lot of things. Then you've got this Cambrian explosion of AI, right? Like when, it used to be that when somebody would build a company, you knew the engineering efforts that went behind it. You knew what it would take.

• 45:30Speaker 02

  But now there's all sorts of things emerging where you have to like really think for yourself and you have to really, you can't look at social proof. You can't look at, you know, there's just so many startups, just like, there's so many, there's not a shortage of people trying to start companies, which is incredible. And so I think that's giving people a bit of pause because they're, they're not sure where to invest. You know, it's like, yes, AI is obviously a thing. We chose picks and shovels. And we invested heavily in the infrastructure of AI. I do think that was the right choice. And, um, but there's going to be a lot of companies that, where the first mover advantage is not in their favor at all.

• 46:14Speaker 02

  And so I think people are holding their bets back and waiting to try to see how that all sorts out. And then defense, I think is a little bit ahead of its skis.

• 46:24Speaker 02

  You know, we were just having a conversation earlier, Lee and I about this is, you know, selling into the government is really hard. And I think people don't understand that, like it, and this may change with the new administration. And it may not, they may get in there and discover just how difficult it is to unseat some of these, you know, entrenched, established people and organizations that do not have any incentive to lead. And, um, so, and Dural took a long time to figure out how to sell into the government. And, you know, at some point, you know, maybe that process speeds up.

• 47:01Speaker 02

  You know, we were discussing this earlier, but- It's not going to be right away. And I think that, you know, there's a lot of capital being deployed in that area. And it just sort of remains to be seen of whether or not they have the chops to do those kinds of sales. And because I think people underestimate how hard it is to do an enterprise sale or a government sale. Like, those are two very, very difficult things that take a long time.

• 47:24Speaker 01

  I think you're still dealing with the hangover of 20 to 23 or so from a while there wasn't liquidity, there was there's a movement of like, an early stage manager gets to invest in this thing, and then their deal quickly got marked up. And then, wow, all I have to do is go get my deal get marked up. I kind of see what this other people like doing. I should do more of this AI thing, or whatever the thing of the moment is. And then they get the the feedback cycle was quite positive. They were getting, you know, positive feedback from that system working in the way it did. And now that, you know, the exits aren't happening, it's all kind of coming down to some extent. And profitability

• 48:07Speaker 01

  matters. And all the things that used to matter about businesses are mattering. And so therefore, the fund managers aren't getting marked up as much. And then the startups themselves are suffering from a more conservative set of early stage investors who are reacting to the fact that they're not getting that juice, that dopamine hit, that that markup that they used to. And that's probably why a lot of people are upset about how, oh, if I'm AI startup, that's the only way that I'm getting funded. It's a consequence of cheap and consensus thinking, I think, within a group of people who are rewarded a certain way. And from our perspective, we've always tried to be like, let's just not get involved

• 48:52Speaker 01

  in that as much as we can, and run when others are run into different areas that others are, you know, are running for are running toward running away from things that people are running towards.

• 49:01Molly O'Shea?

  I have a selfish selfish question. How do you guys feel about the services enablement construct of? You know, companies and startups, there's a lot of venture dollars going towards like PE type companies like and applying AI to that. So what's your position on it?

• 49:20Speaker 01

  I tend to, I always think of things as like science or something about a thumbnail, a thumbnail or a fingerprint as a unique thing. I, I love that. I'd never heard you say that. I think of things as snowflakes, companies are snowflakes. So you have to really evaluate every company individually. So broadly speaking, I, you know, it's, I don't take nor, I'm neutral on, on that. I think it's, it just depends on the situation. But yeah, certainly there's new ways at which capital formation is happening. One of our partners, Pascal, who's a venture partner, also runs something called Meets the Labs, which is his going out and buying

• 50:04Speaker 01

  small SaaS businesses and being a small P fund. And it's, it's going quite well. So I think you can, you can do that. It can work.

• 50:13Molly O'Shea?

  Yeah, it's been an interesting, I was waiting for that.

• 50:20Speaker 02

  I'll take yours.

• 50:21Molly O'Shea?

  Okay.

• 50:24Speaker 01

  Awesome. You can have it.

• 50:25Speaker 02

  Yeah, I'll take yours.

• 50:28Speaker 01

  Yeah.

• 50:29Molly O'Shea?

  Awesome. Okay. So as we wrap up, I have one final question, but two parts. So I want to hear your highlight from 2024 and I want to hear what you're most excited about for 2025.

• 50:44Speaker 01

  My highlight, well, I think it's, we just spent an incredible time with our team and the team's families at a retreat. And it was just really amazing to celebrate all the things that have gone really well for, for the team and in ourselves personally, but also to get to experience it with our families. For my two daughters, to be playing with my, my partner's daughters and, or, you know, that it was just really a special time and an incredible atmosphere. And yeah, that, that was my highlight. I think it, for, for

• 51:24Speaker 01

  me, my life and work have always been so intertwined. At our, at my wife and I's wedding, I looked out at the, at the group of people. I love them all so much. And then I realized my Becca was like, You've worked with basically all of these people. And I was like, oh yeah, this person gave me money and then I gave them money. And then, you know, this person hired me once and I just, it's just this intertwining thing. And it's just, um, I, I, I really love that because I can spend time with people I love and friends and, and all the time. It's a way of integrating all of your things you care about into your, into your life. So that was my highlight. Thing I'm looking forward to, yeah, it's continuing to grow personally and learning how to work with other people because I think it's, and continue to work

• 52:09Speaker 01

  with other people. Because I think if you want to do really amazing things in the world, which I do, uh, you have to continue to be good at, um, working with others and, and, and exciting others and motivating others and getting other people and, and integrating their life, their hopes and dreams into your own and doing great work together. Because you can be pretty lonely if you just want to do things on your own. I just don't think you have as big of an impact. And for me, I'm a social person, so I need to do it with others. The solo GP thing was never gonna work.

• 52:43Speaker 02

  Before I came along, he was solo. And, uh, the two of us got together, we accidentally formed a venture firm. So, oops. We need to get somebody to run operations around here. And we need somebody to like, we need, we gotta do all this stuff now. Um, which I'm, I'm gonna go with the first, the very first picture that arrived in my mind with that question, because I'm a very visual thinker and it's gonna be a funny one. But, um, we throw this thing called Reverie and we did our very first founder Reverie. And I remember seeing the tent. Um, we had this tent that we all met in. And when I was walking up to

• 53:25Speaker 02

  the tent, I was filled with this enormous gratitude for this tent. Now, obviously I can afford to rent a tent and I can erect my own tent. But there was something about the fact that we built a company and built a venture firm that could afford a tent. You know, and that there were a hundred people underneath it.

• 53:43Speaker 01

  Uh huh.

• 53:44Speaker 02

  And that we were all gathering together that just really hit me hard. I remember I almost cried. I, I was so thankful and so happy about that darn tent. And so I think that leads to what I'm looking forward to, which is we have an office and we just got an office and it's our permanent.

• 54:03Molly O'Shea?

  Wow.

• 54:04Speaker 02

  And I'm looking forward to our housewarming party. Because our office is a home, uh, which is going to be kind of weird for some people when you come in. We have a fireplace and we might be baking cookies and you know, the, the, the memories that we create as a team, like this offsite that we just went on. We have shelves that we collected on the beach. They're going on the fireplace, just like a home would be. And there's something so special about having this hub and this home that we gather at. And we, I can't wait to see what comes out of it. And so I, I also can't wait to create more of these recipes for these events with Mike and with the team.

• 54:42Speaker 02

  And just seeing like where we can take this because at the end of the day, I am a capitalist, but I'm also an artist. And so being able to merge those two things together and to be a venture capitalist artist or a venture artist is a dream come true for me. And I think that Lee, one of the most remarkable things about being his co-founder is he has always celebrated and tried to honor and draw out my authenticity and who I am as a person. And he sees me, he's always seen me where other people have misunderstood me. And so giving me a campus and a place where I can play has been remarkable and very special. I'm glad that people around the world, as you say,

• 55:27Speaker 02

  are experiencing our events and seeing firsthand how if you treat life a little bit like immersive theater, which it is, one big theater. And as Shakespeare says, we are all actors and this is merely a play and every man and woman plays their part. Then you get to have a lot of fun. And so I'm really looking forward to how much fun we get to have as a team and all these magical moments we get to create together. And that's kind of what came to mind right away and is that darn tent. You know, I

• 55:58Speaker 01

  Hmm, more tense.

• 56:00Speaker 02

  It's a simple thing. It's a very simple thing, but we can afford it. So

• 56:06Molly O'Shea?

  It's amazing.

• 56:06Speaker 02

  It was just darn cool.

• 56:07Molly O'Shea?

  It's amazing. Well, Lee, Cyan, this was an incredibly magically weird conversation. And I loved it so much. It was so much fun. Thank you so much for your time.

• 56:19Speaker 01

  Thank you, Molly. It was really great.

• 56:21Speaker 02

  Thanks, Molly.