![[26-Cyan_Banister.jpg]] *Dialectic Episode 26: Cyan Banister - A Fool’s Derive - is available on [Spotify](https://open.spotify.com/episode/6rX6uNyBsO83Fh5ZuzmdeG?si=e393f621bd0a4cbd), [Apple Podcasts](https://podcasts.apple.com/us/podcast/26-cyan-banister-a-fools-d%C3%A9rive/id1780282402?i=1000722742633), and [YouTube](https://youtu.be/lcO4shsZP08?si=7pWFH9hyFBiZJTUV), and all podcast platforms.* <iframe data-testid="embed-iframe" style="border-radius:12px" src="https://open.spotify.com/embed/episode/6rX6uNyBsO83Fh5ZuzmdeG/video?utm_source=generator" width="496" height="279" frameBorder="0" allowfullscreen="" allow="autoplay; clipboard-write; encrypted-media; fullscreen; picture-in-picture" loading="lazy"></iframe> <iframe width="560" height="315" src="https://www.youtube.com/embed/lcO4shsZP08?si=rhhqiJoepId4Q7-2" title="YouTube video player" frameborder="0" allow="accelerometer; autoplay; clipboard-write; encrypted-media; gyroscope; picture-in-picture; web-share" referrerpolicy="strict-origin-when-cross-origin" allowfullscreen></iframe> <iframe allow="autoplay *; encrypted-media *; fullscreen *; clipboard-write" frameborder="0" height="175" style="width:100%;max-width:660px;overflow:hidden;border-radius:10px;" sandbox="allow-forms allow-popups allow-same-origin allow-scripts allow-storage-access-by-user-activation allow-top-navigation-by-user-activation" src="https://embed.podcasts.apple.com/us/podcast/26-cyan-banister-a-fools-d%C3%A9rive/id1780282402?i=1000722742633"></iframe> # Description Cyan Banister ([Website](https://cyanbanister.com/), [X](https://x.com/cyantist), [Substack](https://uglyduckling.substack.com/)) is an investor, artist, and co-founder and General Partner of [Long Journey Ventures](https://www.longjourney.vc/). Previously, Cyan spent four years at [Founders Fund](https://foundersfund.com/) and has a legendary angel investing track record alongside her husband, Scott, including early rounds in SpaceX, Uber, and DeepMind. Cyan is as original as they come: she grew up on a Navajo reservation and was homeless by 15, with a series of unlikely serendipitous moments combined with optimism, agency, and love of capitalism taking her to a very different life than the one she grew up with. I focused this conversation not on Cyan's work, but her unique approach to living. We begin with Cyan’s “church”: a weekly visit to see Bobby McFerrin and co. do live, jazz acapella in Berkeley, CA. We discuss how this space ties to presence, openness, and play, and then talk about the tension between novelty and consistency as she continues on her own path toward self-love and mindfulness. She also tells me about her radical approach to accountability and the empowering results of assuming that everything is her fault. One of Cyan's favorite words is the French *dérive,* or an intentional drift, and it embodies her approach to the world. She moves with childlike wonder, seeking to see things and people from new perspectives and challenging others to react beyond their default settings. She daydreams about the outcomes she wants and has remarkable conviction and faith even when others do not believe her. We wrap with a grab bag representative of Cyan's diverse interests, from filmmaking and performance art to the US Constitution to Bill Murray. Cyan manages to combine randomness and intentionality, naiveté and sober-minded awareness, humility and conviction. I hope you are are as inspired as I am to live more playfully, seriously, and courageously. --- Quick note on video: Yes, it is here! I’ve been putting it off for lots of reasons, and today’s episode isn’t perfect (a one-off set in a friend’s space, some audio-video sync issues, imperfect camera angles, so on). Alas, I’m ripping the bandaid off and you can expect some future episodes to include video versions. Feedback is welcome. # Timestamps - 0:03:45: Cyan's "Church" - 0:16:21: Stillness, Mindfulness, and Introspection - 0:28:47: Learning to See in Original Ways - 0:39:38: People: When the "Light is On," "Collecting Minds," and Conjuring Friends - 0:46:55: Cultivating Childlike Joy and Refusing to be a Victim - 0:52:30: Radical Accountability - 0:56:28: Randomness, Faith, and Experimentation - 1:06:22: Conviction and Peter Thiel - 1:12:54: Returning to Seed Investing and Long Journey Ventures - 1:18:23: Thoughts on Art - 1:23:42: Performance Art - 1:26:37: Cyan's Creative Projects - 1:32:51: Boredom - 1:36:06: Living Around Elderly People - 1:42:14: Pete Buttigieg - 1:45:57: Being a Role Model - 1:48:26: Young People's Future - 1:52:46: Scott Banister and Lessons for Her Kids - 1:55:35: "It Just Doesn't Matter" And Who Pulls the Strings # Links & References - [Cyan - by Kevin Gee and Dan Scott - Cloud Valley](https://cloudvalley.substack.com/p/cyan) - [Cyan Banister — From Homeless and Broke to Top Angel Investor - Tim Ferriss](https://tim.blog/2024/11/28/cyan-banister/) - [Investing for a Higher Purpose - Invest like the Best](https://joincolossus.com/episode/banister-investing-for-a-higher-purpose/) - [Bobby McFerrin](https://open.spotify.com/artist/2FjkZT851ez950cyPjeYid?si=b7buiA7wShCdGwUGV7y2fg) - [I make my bed every day as a love letter to my future self.](https://x.com/cyantist/status/1943729296117575832) - [University of Texas at Austin 2014 Commencement Address - Admiral William H. McRaven](https://www.youtube.com/watch?v=pxBQLFLei70) - [Example of Motion and Bobby's performance](https://www.youtube.com/watch?v=bojmGnsPNUc) - [The Magic Glasses - Frank Harris](https://www.goodreads.com/en/book/show/7096867-the-magic-glasses) - [The Magic Glasses by Frank Harris (Part 1 of 3)](https://www.youtube.com/watch?v=SKLld47t4TA) - [‎Little Miss Sunshine (2006)](https://letterboxd.com/film/little-miss-sunshine/) - [My Life and Loves - Frank Harris](https://www.goodreads.com/book/show/560318.My_Life_and_Loves) - [Steven Banks](https://www.imdb.com/name/nm0052246/) - [The cart path with Lawrence Krauss - Cyan Banister](https://uglyduckling.substack.com/p/the-cart-path) - [Man's Search for Meaning - Viktor E. Frankl](https://www.goodreads.com/book/show/4069.Man_s_Search_for_Meaning) - [The hardest thing is taking responsibility for everything in your life. It is also the most liberating thing. - Kamal Ravikant](https://x.com/kamalravikant/status/1952388306710286792) - [‎The Matrix (1999)](https://letterboxd.com/film/the-matrix/) - [Leaves of Grass - Walt Whitman](https://www.goodreads.com/book/show/27494.Leaves_of_Grass) - [Dune - Frank Herbert ](https://www.goodreads.com/book/show/44767458-dune) - [Lee Jacobs](https://x.com/leejacobs?lang=en) - [‎American Beauty (1999)](https://letterboxd.com/film/american-beauty/) - [The Constitution of the United States: A Transcription](https://www.archives.gov/founding-docs/constitution-transcript) - [The world is a museum of passion projects. - John Collison](https://x.com/collision/status/1529452415346302976) - [The Song of the Lark - The Art Institute of Chicago](https://www.artic.edu/artworks/94841/the-song-of-the-lark) - [BILL MURRAY TALKS ABOUT THE PAINTING THAT SAVED HIS LIFE](https://www.youtube.com/watch?v=-d9soehNJJU) - [Birds Aren't Real](https://en.wikipedia.org/wiki/Birds_Aren%27t_Real) - [Jane Thomas Anderson, 93](https://www.valleycenter.com/articles/jane-thomas-anderson-93/) - [Edge Esmeralda 2025](https://www.edgeesmeralda.com/) - [Halt and Catch Fire](https://en.wikipedia.org/wiki/Halt_and_Catch_Fire_(TV_series)) - [The Diamond Age: Or, a Young Lady's Illustrated Primer - Neal Stephenson](https://www.goodreads.com/en/book/show/827.The_Diamond_Age) - [It Just Doesn't Matter! - Meatballs (1979)](https://www.youtube.com/watch?v=-TogGxzlfhM) - [‎The Razor's Edge (1984)](https://letterboxd.com/film/the-razors-edge-1984/) - [Bill Murray gives a surprising and meaningful answer you might not expect. (Charlie Rose)](https://youtu.be/o9TvFkiLLMo?si=yfsII5IDuaMlD4Q5) # Transcript **Jackson**: Cyan Banister. **Cyan:** Hello. **Jackson:** It's really a pleasure to be with you. **Cyan:** It's a pleasure to be here. Thank you for having me. ## [00:03:45] Cyan's "Church" **Jackson:** We met in the spring through our mutual friend Kevin. I was in San Francisco, and on last-minute notice one Sunday night, he asked if I wanted to go to an event with you the next day. He didn't tell me what it was; he just said it was a surprise. So I show up in Berkeley, California. We drive across the bridge and get to this old theater. I'm very confused. We run into you, and I still don't know what I'm getting myself into. We walk in, and there are four people on stage, including Bobby McFerrin, who is a legendary composer and musician. They proceed to start singing jazz acapella. I then find out that this is what you call your church. It was a really special experience. I'm partial because I love music, but it was a spiritual room. **Cyan:** Absolutely. **Jackson:** You've also described yourself as infinitely curious, very novelty-seeking, and broadly chasing serendipity rather than consistency. You make decisions with dice to choose random things. And yet, this seems to be a place you go to quite often. **Cyan:** Yes. **Jackson:** I'm curious what makes that place so magical to you, and two, why it's the type of place that could bring you back and act as a sort of church for you. **Cyan:** I went to Bhutan recently, and a lot of the feedback that I got from the monks there was that I needed to work on consistency. In order to progress in my practice, I had to adopt rituals that help ground me, that helped me remember to be awake. I love going through life by the seat of my pants. If I were a tarot card, I'm the fool. I walk off ledges and I'm comfortable in that space. I am deeply, deeply uncomfortable with schedules, with recurring meetings, with anything that happens with any kind of regular repetition. It's almost like an allergy. I get really upset. But this is a growth area. It started with making my bed. My co-founder and my partner at Long Journey brought up that he had talked to somebody about making beds and how if you make your bed every day, it's a transformative habit if you can figure out how to enjoy it. Then our mutual friend Kevin played this commencement speech from a naval officer or some military guy who talks about, if you do only one thing to change yourself, start by making your bed. The way that I look at bed making is that it's a love letter to your future self. In the morning, I make my bed, and then I say something to myself that's going to return in the evening about how I would like my day to go, how I would like to see myself that day, how I'd like to show up in the world. You might call it an intention-setting exercise. At the end of the day, when I get into bed, I'm grateful and thankful for the day that I had, as well as the morning person who remembered me. It's been a really, really fun ritual. Mystical, Magical, Musical Mondays is what I call what I do on Mondays. This happened because I also have another practice of talking to strangers. I will talk to people from all walks of life. It doesn't matter to me. I think that all human beings are a portal into your inner world. They're a mirror of sorts, and they can tell you a lot about yourself. I tend to be very open, probably more open than people are accustomed to, and it can be very shocking if you're hanging out with me. I was at a Bill Murray concert. He was playing with his blood brothers at the Great American Music Hall. At the end of the show, this guy stumbled up to me, and you might have assumed that he was drinking or drunk or stoned. Everybody was distant towards him and was moving further away. It was like stranger danger. But I did not get a sense from him that he was dangerous. I got a sense that he was really, really trying his hardest to get us to pay attention to something that he wanted to tell us that was special. **Jackson:** He had something to say. **Cyan:** He came over and stood next to me and he said, "Cyan, that's your name, right? You like Bobby McFerrin?" And I was like, "Don't Worry, Be Happy Bobby McFerrin?" He goes, "Yeah. He's playing in a couple days on Monday, and if you would stop by in Berkeley, that would be awesome." I was like, "Yeah, maybe. Let's exchange phone numbers." So we exchanged phone numbers, and my friends were like, "You're crazy. Why are you giving that guy your phone number? Are you nuts?" I'm like, "No. I have a weird feeling. I have a feeling it's going to work out beautifully." I don't know why, but I just do. I get these weird feelings, and I trust them. I trust my gut, my North Star, and my intuition. A week went by, and I was in a bookstore going through books when I saw this little sign that said, "Don't Worry, Be Happy." It reminded me of this guy Dan, who's now my friend. I texted him a picture of it, and he was like, "So nice of you to think of me. Would you come on Mondays?" I was like, "Okay, fine." **Jackson:** Can't get out of this one. **Cyan:** You got me. You lured me in. I started listening to some Bobby McFerrin songs to get ready because I needed to brush up on his catalog. I didn't know a lot of Bobby McFerrin. I showed up on a Monday, and let's just say that nothing prepares you for it. I was changed as a person. I cried, I danced, I sang, and I felt a spiritual presence that's hard to explain. It would be very similar to what someone would describe as going to church. This was probably the closest I felt to church since I was a little kid, where I felt light, love, community, and joy—all the things you're supposed to go to church for, without the control or being told you're a sinner. God is not even talked about. What happens there is a radical encouragement of being nonjudgmental towards yourself and others in childlike play. I think it's so important that people get in touch with that part of themselves, especially if they're creatives or building something. You sometimes have to imagine a world that no one else can see, and who's better at that than kids? I purposely put myself in a position where I can be childlike once a week. I've made it a practice, and I've now gone dozens of times. I try to bring people with me, so every now and then I'll invite 20 or 30 people and tell them nothing about what they're going to experience. I don't even tell them that Bobby's going to be there. **Jackson:** I didn't know either. **Cyan:** Some people have no idea who he is, especially the younger generation. The musical performers he performs with are called Motion, and they're some of the best musicians in the world. They make instruments—they make trumpet sounds, drum sounds, guitar sounds, and saxophones. Then there's an open mic. I don't know what kind of open mic you experienced, but it's different every time. **Jackson:** I was there when the five-year-old French kid got up on stage. **Cyan:** Yes. **Jackson:** And just started singing. **Cyan:** Yes. There was one where a kid was singing about tacos. **Jackson:** Oh my God. **Cyan:** We get people who come in with drums. Sometimes people come in with something rehearsed, which is discouraged. You really want to feel a calling to something. We just hired this group to come out for Reverie for our founders. We did something that we don't do on Mondays : we took out all the chairs and tables, and it turned into a roving circle of different people singing different parts and walking around for 30 minutes. It was phenomenal. There was one person at the very end who just belted out this tune. Afterwards we asked, "What was that?" And he said, "I don't know. I just felt called to it. It just came out of me." That's the thing I want people to get in touch with. There's a type of knowledge inside all of us that's dormant because we forget that we have bodies and what you might call a spirit. We spend all of our time in virtual reality. We're absorbed into our phones; we're not here. It turns out we live in this amazing, incredible world, and it can be absolutely magical. But it takes a type of vision or senses to experience it. **Jackson:** Yes. **Cyan:** It's like being in Plato's cave. **Jackson:** That room had a vibration. Obviously, music vibrates, but you would have to really try to close yourself off to whatever was happening there. **Cyan:** The lessons are endless. A lot of people, when they go the first time, will say, "I was seated next to a person that was completely off tune and offbeat, and it was driving me crazy. They were making bird sounds." You have to remember that for some people, this is their first time expressing themselves in a long time, or it's the only way they know how. It teaches you this empathy and this compassion. Then you find it joyful and figure out how the instrument they're coming up with fits in oddly. It creates a little bit of discomfort, and that's okay. For example, when children get up there, they don't care. They'll just belt out whatever and sing about a hot dog and a truck. They just don't care, and it's delightful. **Jackson:** Bobby and his group were so wonderful. They were so good at receiving whatever people did when they went up on stage; they would just go with it. A really beautiful lesson there. **Cyan:** Thank you for coming. It's very special. If you're listening to this and you're free on Mondays at 11:45, stop by the Freight & Salvage. I'm going to promote this because it's really a labor of love. They don't make any money. Bobby also has Parkinson's. The other beautiful thing to witness when you go is how we could be treating the elderly population. We could be giving them meaning and purpose and putting them in charge of these types of community events. His strongest singing times are between 11:00 and 3:00, and after that, he doesn't sing as well. This gives him a place where he can interact with the public and really enjoy himself. You can also see how they interact with him. It's a really great lesson on how you could treat your parents, loved ones, family members, or even strangers who are experiencing memory changes or cerebral changes of some kind. It opens up your empathy for that and how we could live in a different future. **Jackson:** It's really special. ## [00:16:21] Stillness, Mindfulness, and Introspection **Jackson:** Speaking of spaces, you seem to be very into presence and paying attention. A couple of quotes from you are : "I hate knowing what time it is," and "Everything I do is a waste of time." You often talk about remembering that you're going to die and how that affects perspective and presence. One more quote: "The moment I cease running experiments on my life is when the true experiment begins. What if all my searching was merely the cosmos teaching me how to be still enough to receive what was already mine? The dice roll themselves when I am truly present." This ties into what we talked about at the beginning with Bhutan. How have you learned, or what have you learned, about stillness? **Cyan:** One of my favorite quotes is something like: "Enlightenment resides in the stillness between thoughts." It's very true. When you hear something like that and get into meditation or mindfulness, your very first tendency—at least for me and for many people when I started teaching mindfulness classes about presence—is to treat it like a quantified thing that you're doing. It's a little competitive because we have this with Duolingo, Calm, and all these other apps that we're using. It's how we're trained. **Jackson:** There's a mindfulness score. **Cyan:** There's got to be a score. The first mistake you'll make is thinking, "I have to quiet all these thoughts. If I don't, then I'm doing it wrong." Then you get into this horrible loop where you're punishing yourself because you couldn't quiet your thoughts. I was going at it like that constantly and finally realized I needed to surrender that idea and instead observe my thoughts. That was a huge shift because I started to realize and start asking questions about those thoughts. "How do they occur anyway?" "Why are they floating past like a cloud now?" "Are they my thoughts?" You start going down these rabbit holes, and you turn over as many stones as you can. I think it was Plato that said that a life not examined is not worth living. We look outside externally to the cosmos, to the world, to the ocean—not as much as we should—but we rarely look inside and go deep into the universe within. When you go inside and you start asking these questions, you start realizing there's a lot more to the world than you could even fathom. Forget about what's outside, just inside. You start to understand what the ego is, what it's not. When you say, "I am," who is "I" anyway? What self is speaking then? Which of my selves? You could be multi-fragmented. Many of us are. Then you also start to realize you're sleepwalking through life. This introspection started about 25 years ago. I was asked a question by my dear friend Tom here in San Francisco. Over on Divisadero street, there was this cafe called Cafe of Beer. I think it might be gone. They had beanbags. We were sitting in the bean bags, and he said, "Cyan, how did you survive?" I just lied to him. I made something up because I actually don't know. We do this all the time. I'm a middle child. I was mostly left to my own devices. These things you say are a social thing so you can continue the conversation, but you don't really know. You just make it up because it seems like it makes sense. When I went home that night, I felt very uneasy. I had no idea how to answer that question because I really don't know the answer. So I started asking myself, who along my journey helped? What were the inflection points along my life's path where if that person wasn't perfectly there at the right moment, I wouldn't have survived? They start highlighting in the timeline. You start to see them. The first realization is, we are not alone. We think that we're individuals and that everything that we do is through our own will and might. We're geniuses. All of our thoughts are ours. These are things that the ego does to play tricks on you. It's not like I spent every moment on this thought, but if I had an idle moment—I told you when we met that I'm infinitely curious—I will sit there and ask questions and try to come up with answers because there's so much to think about. I can never be bored. So I started going down that rabbit hole, and then about the pandemic. Art is amazing, and it can often reach you at the exact right moment where you need it. You might watch a movie and then walk out of the theater, and suddenly everything is a little brighter, and you just have this aha moment, this epiphany. I try to immerse myself in as much randomness and art and experiences that I possibly can so I can receive these epiphanies. I had one such epiphany after the pandemic. I like to think of the pandemic as this great shock. It's a moment where you fell into a couple of categories. One, you were isolated and at home, or two, you had to work in the public or the hospital, and you didn't get a break at all. You actually worked more than everybody else. Those poor people still probably haven't had a break. Think about it. **Jackson:** It was a pause for most people, and I hadn't paused. **Cyan:** No pause for some. When you come out of that, you have a type of trauma and suffering that is universal, that happened to all of us at once. The questions that come after that are typically: if there is a God, why would God create a virus? Why would we have a pandemic? Why would this even be allowed to happen? You'd think that a lot of people would turn out to be atheists and say, "There is no God." But the interesting thing is, a lot of people turned to spirituality. Bible sales went through the roof because people went inward and started discovering things about themselves that they didn't even realize. I'm one of those people. I had an experience that completely shifted my view of the world and of reality, and I haven't been the same since. I just learned a French word I'm probably going to butcher: dérive, which means to drift intentionally. **Jackson:** Wow. **Cyan:** I felt very seen. They have amazing words that we don't have that so beautifully describe something. **Jackson:** There are all these words in different languages that are only captured in that language. There are all these Japanese words, for example. **Cyan:** Japanese words are amazing, too. They have words for shadows that come through leaves. **Jackson:** Komorebi. **Cyan:** Exactly. We don't have that. **Jackson:** I know. **Cyan:** In Finland, they have words for all the sounds of snow when you walk on it. They have 15. **Jackson:** They need those words. **Cyan:** But we don't. English is amazing, but we don't have something like dérive. I'm a wanderer. I am tethered by some of my life's choices, but in general, I like to roll around like a tumbleweed. A lot of my decisions, my gut instinct, and what I like to do comes out of that random space. My mindfulness practice has taught me how to trust my instincts more. That's one of the things I would love for people to realize : a practice that is only two minutes a day can change your life. You don't need to meditate for hours, go to a silent retreat for seven days, or do ayahuasca. I see all these people doing ayahuasca, and they're not changing. They're not happier or better. They're not going inward like they should, surgically dissolving some of these false selves and integrating the lessons they're getting. I feel it's imperative that people start being more mindful. It can come through forms—we were talking about Bobby McFerrin. It can come through moving your body or singing, a daily exercise of walking, making your bed—in so many different ways. I honestly think that founders would be better leaders. They would have more clarity around their mission and purpose and be less distracted by things that don't serve them. They'll find that accomplishing everything they want to accomplish is a lot easier than they think it is. **Jackson:** Less resistance. **Cyan:** A lot less resistance. **Jackson:** In this theme of waking up and mindfulness, sometimes people hear those words and their eyes glaze over, or they have a loaded connotation around meditation. I know you've studied Gurdjieff a little bit. I'm not deeply familiar, but I know there's one idea he has that is this triptych of mind or head, body, and heart. you have a frame you would offer people for what captures everything you just said? Maybe people have tried meditation and they struggle. What is the organizing thing there? What is the core part? Is it simply observing your own thoughts? Is it time alone? **Cyan:** The very first step is observing your own thoughts. If you do nothing else, do that. Everything else comes after. When you observe your own thoughts, let's start with happy. You're happy and you say, "I am happy." It's almost like a magic spell. You self-identify with happy and you will magically become happier. It's weird. You say, "I am happy." **Jackson:** You're hypnotizing yourself. **Cyan:** Then you have to ask yourself : "But who is I?" I really love this trick. You say : "It is happy." **Jackson:** Whoa. **Cyan:** That changes everything, because then if it is happy, who am I? Then you start to realize that you might be the observer, or you might be the true I. I would go down that rabbit hole as far as you can go, so you can figure out who yourself is and meet yourself. You might discover that there's this self that thinks all kinds of things that are just false. It might hold on to memories of the past or projections to the future that are complete illusions. This is why presence is so important, because presence is real. The future doesn't exist and the past is gone. The sooner that we can realize that these are stories or fiction, or part of our great work of our life, and we change our relationship to these stories and even the stuff in the future, the better off we're going to be for each other, for ourselves, and in the world. **Jackson:** The original question was about stillness, but you captured stillness and presence. ## [00:28:47] Learning to See in Original Ways **Jackson:** This ties into something I'd love to talk about: seeing. Seeing with a new perspective or a reframe. In the first interview I ever listened to you on, with Patrick O'Shaughnessy, I wrote in my journal: "Toward the end she spoke about how the world is magical if you look. That's been a recurring theme in various places lately. The extra sense that allows you to tune into a different frequency, or perhaps is as simple as awareness and a desire to look." You've also referenced "The Magic Glasses" by Frank Harris. There's a bit in there where a painter with distorted vision says, "If my eyes had been all right from the beginning, I might perhaps have been contented with what I saw. But as my eyes were imperfect, I tried to see things as my soul saw them and so invented looks and gestures that the real world would never have given me." How have you learned to see? You have a unique background. Has that enhanced your ability to see? Are there different ways of seeing more, seeing better, or seeing differently? **Cyan:** Yes, without a doubt, my background has shaped my vision. There are a lot of things I don't understand. Some people have described me as an alien creature. **Jackson:** An alien who really likes people. **Cyan:** That really likes people. I'm here on Earth and I really like you guys. There are a lot of human behaviors that make no sense to me, and I laugh at them because I don't know what else to do. People project their inner worlds onto others and make assumptions. They assume I'm judgmental when I'm not being judgmental at all. Or they assume I'm aloof or unhappy because they want to please me, but that's not my reality on the inside. **Cyan:** When I was growing up, I was non-verbal for the first five years of my life. When people spoke, the words had weight and gravity. An adult would say something, and suddenly motion would happen. People would move or change rooms. They seemed like magic spells or commands. I observed people using words and how others would react to them, and I made a pact with myself that I wouldn't speak, even though I knew how. **Jackson:** You were deliberately non-verbal? **Cyan:** I was deliberately non-verbal. It turns out there are a lot of us. When I started speaking about this, multiple engineers have come up to me and said, "That was me, too." Some chose not to speak until they were 12 or 13, some all the way into adulthood. **Jackson:** Have you ever seen Little Miss Sunshine? **Cyan:** I have. **Jackson:** It reminds me of Paul Dano in that movie. He takes a vow of silence for specific reasons. **Jackson:** Well I took a vow of silence! And part of it was really delightful because I loved watching how people would treat me. They would treat me as if I was incapable of rational thought or a lot of things. They made a lot of assumptions about this child that doesn't speak. It must mean that she's slow, not very smart, or incapable of understanding what you're talking about. **Cyan:** That part was really bizarre because they would have conversations that no child should listen to. This made me a deep observer. I learned through watching people, and I still do. A lot of the time, I will go and sit at a mall or in a park. I'll sit at the airport, and I will just watch people. I watch the conversations that they have, how they interact with each other, the devices they're using, how they're dressed, and the phrases that they're using. It's just a fun thing to watch people because it informs a lot of my views, the things I want to invest in, and the things I want to work on. I love to immerse myself in humanity. That story hit me during the pandemic. I was one of those people that took a pause. In my early life, I didn't read a lot of books. I read a few science fiction books and then mostly technical manuals for my job. Really boring, dry stuff to most people. Very exciting to me. During the pandemic, I decided that since I had never given myself the luxury of reading philosophy or classics, I was going to try. Interestingly, they gripped me. I was not expecting that. I started going down these rabbit holes of weird, esoteric stuff and found that Frank Harris story. If you look up Frank Harris, I'm going to warn you that he is a troubled individual who wrote the most notorious smut book of the time. **Jackson:** Wow. **Cyan:** He details all of his loves. It's called My Life and Loves, and it's very graphic. **Jackson:** This is late 1800s. **Cyan:** Late 1800s, early 1900s. The book was banned everywhere. It's one of the banned books. He was a ranchman, and he—I think—killed people. If you go and read about him, you'd wonder how this story changed my life. **Jackson:** Not a pure endorsement. **Cyan:** Not a pure endorsement. I'll just put that disclaimer out there. But this story did change my life. It made me realize that we all live in different realities, and it really brought it home. If you ask anyone if they have an inner monologue, you might discover that some people don't have one. If you ask people whether they can visualize something, some people cannot. If you ask people if they see color, sometimes they see color differently. If you're someone like me, I think in pictures and video, and I have very immersive VR experiences when I think about problems. We're all in this very different reality, and it's shaped by how we view the world, what we believe in, our ideology, and our experiences in life. That story is really about this question: if you could try on a new perspective, how would you see the world? That blew my mind. I threw this party with Mike Wang, who's my collaborator at Long Journey. Everyone that came to this dinner party had to try on a pair of spectacles, and the spectacles had a role that they had to play written on the side. **Jackson:** Cool. **Cyan:** Maybe you had to be an optimist, or maybe you had to be a pessimist, or maybe you had to act like you're a child. What was really interesting was how seriously everybody took their role, and they got into it. There was someone who was a critic. They were supposed to critique the food and act like they were displeased with everything. We gave that role to a person who's a people pleaser. **Jackson:** So you hand-picked every role? **Cyan:** Yes. For this one, we knew the people and we knew their personalities, so we gave them a personality that didn't suit them. **Jackson:** One of the lovely things about games is that people are so willing to opt into something so seemingly ridiculous, as long as you scope it or call it a game or a party. **Cyan:** It was so fun. We had this eye doctor, a friend of mine, and she worked the eye doctor station. What people didn't realize is that we already had their prescription filled for them. They thought it was random. I hang out with magicians, and we do something called Magician's Choice, where you make it look random, but it's not. We had these dice they would roll for a color, and it would land on a box. From that box, they were able to pick out a pair of glasses. It turned out that every box was the same, and there was a pair of glasses for them in every box. It was a force. They got what they thought was a random prescription, put the glasses on, and immediately got into character. There was a guy who was supposed to be five years old, and he kept demanding bowls of sugar. He was saying, "I want sugar and I want it now." There was a person we blindfolded, so they couldn't see and had to eat their whole meal blindfolded. The person sitting next to them was supposed to help. This is a person that doesn't like to help anyone and is deeply uncomfortable with that role, but he got into it. **Jackson:** You're a sort of group therapist/party host. **Cyan:** I have **I have a motto:** a motto: you should never throw **Cyan:** an event if it doesn't change people and give them a memory that will last for the rest of their lives. It's a high bar. If you start to do that, you become an artist and can play with reality in a way that's just delightful. You become a fun prankster for good. After that amazing meal, everyone said it was really transformative. It was crazy. I was inspired to turn that short story into a movie. It's been adapted into a full-length feature film script, and we're almost done with it. **Jackson:** Oh my gosh, you're producing. **Cyan:** Yes. **Jackson:** Wow. **Cyan:** I'm very, very excited about it. **Jackson:** The Magic Glasses. **Cyan:** The Magic Glasses. It's probably going to be called something else, but the current working title is The Magic Glasses. **Jackson:** Wow, cool. Any timeline? **Cyan:** Right now, I'm learning about scriptwriting. I hired an amazing collaborator and scriptwriter, a man named Steven Banks, who was one of the lead writers of SpongeBob. He's fun to work with. I told him about my vision. It was my first time collaborating with someone in this way, and I realized I could bring my ideas to life by working with someone who has a skill set I don't have. **Jackson:** Yes. **Cyan:** We've been getting along great. We're on our fourth turn. The other realization I had is that it's like sculpting. You get a skeleton, then you start packing on meat, and eventually, you get to the finer details of the script. We're in the finer details now. Once we're done, we'll go into production. I don't know who is going to direct it. Ideally, it would be him, but he has to be available. It's really nice if the person who writes it is also the director. **Jackson:** I want to come back to that later. ## [00:39:38] People: When the "Light is On," "Collecting Minds," and Conjuring Friends **Jackson:** On the note of seeing people, there's a quote. You're talking about Lawrence, who you also interviewed. You say, "I've never met someone more astonished by the world around him. He was walking along a cart path and looking at plants with the wonder of a kid who just discovered photosynthesis when he suddenly looked up at me and smiled, then said hello. His light was and is on." "His light was and is on" is a pretty amazing line. **Cyan:** Yes. **Jackson:** Can you say more about what that means? **Cyan:** Sometimes you meet people in life where they're present and they're really taking in something, and you know that their light is on. I don't know how else to describe it, but they look out. They see you. When you walk around on the street and you try to make eye contact with people, you'll find that people will either actively avoid your eyes or they won't notice you're looking at them at all. They're in these reality tunnels where they're thinking about their to-do list, what they have to do when they get home, someone they disappointed, or replaying a conversation. All of these things that are not real. **Jackson:** Or they have AirPods or literally their phone in their face. **Cyan:** In that moment, when I saw him, he was deeply involved with a plant. He was really taking in that plant and noticing everything about it. He looked up and he noticed me and noticed the surroundings. It was really delightful to see that. I've continued to see that in him. He's human, just like all people. He falls asleep just like the rest of us. But when he is aware and awake and really looking at the world, he sees it in a way that I find profound. I noticed that about him, and I endeavor to be like that. **Jackson:** One more quote in this vein: "It is just something you notice when you collect minds like I do. I found a remarkable one, like a rare Pokemon, and I was excited." What does it mean to collect minds? **Cyan:** I collect minds. Everyone is individual and unique, but there are some people who are just more unique than others. I don't know why. Some people give themselves permission to really discover who they are and what they're not and have a strong sense of that. I'll meet people, and they have an essence. I describe it as an essence—a unique signature to them. It's not a smell, but a unique fire that every person has. I know when I meet someone that they're different than anyone else I've ever met, and I immediately want to collect them. "Would you please be in my life? I don't have a mind like yours yet." **Jackson:** Wow. **Cyan:** Every mind is a mirror. Ever since I was young, I used to have this space. It's a green field. I still have it. A green field with a picnic table or bench in it. I go to this picnic table or bench and invite friends, and they sit down with me and model out the world with me. When I am asking these questions and talking to people, I'm not talking to myself. I'm talking to a model of a person I'm bringing into this world. Every mind I collect becomes one of these voices. I'll ask myself: "what would Jackson think of this? How would Jackson view this?" Or Kevin, or anyone. Kevin's very unique. **Jackson:** He is. **Cyan:** Bringing in his mind into something is a whole other tool set. There's only one Kevin. Every now and then, I summon Kevin to the bench because I really want Kevin's ideas. There are all sorts of friends that I have summoned to the picnic bench. You can look at it a few ways. The person I'm conjuring might be their higher self, and they might actually be there. Or it's my mental model of them and how I would think that they would behave or react to something based on my observation of how they go through the world. A lot of what I do is summon someone I admire and say, how would my friend Pin handle this? Or how would a child handle this? Or Marc Andreessen? You can bring them in. **Jackson:** Can you do this with people you haven't met? **Cyan:** To some degree. I think it's harder because people don't always show you who they are in public, so you're not getting a real glimpse into the authenticity of that person. If you spend time with someone long enough, you start to notice the gait of how they walk. You start to notice the pauses that they take. You start to notice when they're putting on a facade. You start to notice the real truth of them, which you're not going to get off Twitter. Twitter's definitely not real. **Jackson:** What would the line be between doing this in your head versus actually calling them? **Cyan:** If you call somebody, you are taking up their now; you're taking up their time. I try to be judicious with that because it's life energy, it's life force. But if I'm really stumped and I can't figure out what someone would think, then I call. I say, "Hey, I was working through this problem, and this is what I thought you might say, but I was wondering what you would actually say." **Jackson:** Cool. **Cyan:** They'll workshop it with me, and it's really delightful. I have a handful of those friends that I do that with. ChatGPT has actually been a great friend. People are talking about ChatGPT psychosis and how this could go awry with a sycophantic voice, so I always have to remember it's a sycophant. Every now and then, I'll take some text that someone sends me, run it through ChatGPT, and ask it to decipher it for me. I don't like to make assumptions about people. If I read something that is not very direct and is subtle, has any kind of ambiguity, or could be taken 20 different ways, I don't know what to do with that information. Sometimes someone will send me a text message and I'll just run it through ChatGPT and ask, "What does this mean?" **Jackson:** Gut checking? **Cyan:** Depending on their mental model, it could mean a lot of different things. Sometimes I'll just use it as a sanity check. **Jackson:** Collecting minds. ## [00:46:55] Cultivating Childlike Joy and Refusing to be a Victim **Jackson:** One last bit here. You are someone who has a childlike wonder. In Kevin's piece on you for Cloud Valley, this amazing long profile which I would recommend people read, he says, "but most people whom she encounters like her—'like a flame to moths,' her husband Scott says, Cyan Banister suspects it's because she reminds people of something they've lost. 'Everyone wants their childhood back,' she says." You had a complicated and in many ways painful childhood, and yet you radiate this childlike joy and wonder. What are you pulling from? **Cyan:** It was those first five years where I was alone in my mind. When did I lose my innocence? When did I start listening to adults that I should grow up and get rid of my foolish nature? When did I decide to start cosplaying? Because we all do. We all have this mental model of what we were supposed to be when we were grown up. If you look back, everyone would always ask you : what are you gonna do when you grow up? You might have a fantasy. I had fantasies, and I remember those fantasies of what I was gonna be, how I saw myself in the future. Adults around us in society and culture stamp it out of us. They tell us that it's wrong to be foolish, it's wrong to play. At some point, it's very discouraged. We create these masks. **Jackson:** Stay in line. **Cyan:** Stay in line. I chose at a very young age to never give it up. I want to be true to myself and authentically me, and I don't want to ever lose this sense of wonder and childlike curiosity that I have. It served me well. It's been my companion in lonely times and hard times. How I got through all of those hard moments, including the stroke I had five or six years ago, is by looking at it with questions and just saying, "Why am I in this situation?" Instead of saying I'm a victim of the situation, I would say, "What are all the external factors that led to this occurring? Is it really just targeted at me?" No, it turns out I'm part of this big ecosystem. My mother probably has mental health issues. I haven't been able to identify what sort of trauma she faced in her life that turned her into who she is, but my dad's trauma is very clear. When you start to look at trauma as cyclical, and family members reenact the trauma that they experience themselves, you realize that they couldn't help themselves. When you realize that people are mechanical and they're not even awake—it doesn't mean a whole lot until you've experienced it. Sam Harris and a bunch of people talk about how people don't have free will. For the most part, we don't because we're not conscious or aware of what we're doing at any given time. 99% of the time, we don't know what we're doing. But in those rare moments where you are conscious, mindful, and present—you know where you are on this planet and you will something into existence—then you might have free will. A lot of my success actually comes from this reckless abandon that I have. It looks counterintuitive. People say, "She didn't grind away at university. She didn't follow the path that everyone's supposed to follow," yet I ended up in the same place. That should tell you something. Am I an outlier, or is everyone cosplaying and afraid? **Jackson:** Maybe both. **Cyan:** It could be both. Life is not as hard as people want to make it out to be. When I say that, people say, "Say that to someone who's in prison, or say that to someone who's starving." I've been starving. **Jackson:** You're a better messenger for that story than most people. **Cyan:** Read \*Man's Search for Meaning\*, which is probably one of the most powerful books ever. You can be in the darkest place, think that there's no hope whatsoever, and still find joy, something to learn, and your love for humanity, because it's still there. As long as you can find those things, you can survive anything. For me, it's a survival tool, and it's served me well. You'll never hear me say I'm a victim of anything, because I always say to look at the ecosystem, look at everything that happened to get you to where you are. You'll realize this was just some dumb luck, or I got a bad luck of the draw with my parents. But I survived, and now I can take control of that. I don't have to live in that narrative anymore. My advice to people is to just be infinitely curious. I think you could turn your life around in major ways if you do. ## [00:52:30] Radical Accountability **Jackson:** On that note of childlike wonder, you can be quite childlike, but you are not childish. And regarding the victim mindset, you are wildly accountable to yourself. **Cyan:** Yes. **Jackson:** There's a quote you shared recently from Kamal Ravikant, who said, "The hardest thing is taking responsibility for everything in your life. It is also the most liberating thing." You have another line from an interview where you say you're aiming to embody the frame of "everything is my fault." **Cyan:** Yes. **Jackson:** I'd be curious for you to talk specifically about accountability and ownership. Agency is a very popular word these days, and it seems this kind of accountability is upstream of agency. **Cyan:** This type of accountability is pretty radical. I recommend that you try it as a thought experiment. All these things are thought experiments. If you ask yourself to be really honest and you say, "This situation that's causing me great pain and unrest, how was it my fault?" you will discover, almost without fail, it's your fault. I'll give you an example. Let's say that you hire a junior employee. For six months you're in the honeymoon phase, but then after the honeymoon phase, you start to see their juniorness. It starts to grade on you. You start to think, "How could they make that mistake? Such a rookie thing." You start this narrative, but if you stop and realize, "I'm annoyed, but I signed up for this. I chose to be a mentor for a young, inexperienced person. I made the bed," you start to realize, "I'm supposed to show up as a better manager. If they're not succeeding, it's because of me." The other thought experiment I like to run is to pretend that every day that you wake up and you get out of bed, you're in a movie and you're the main character. And right now, Jackson, I'm your side character. If you're an actor and you've just been cast in a role, you could be a villain, you could be a good guy, you could be a comedian—you could be a lot of things. But one of the things you should look at is how do you appear in everybody else's story? How do you show up? Every one of my actions could profoundly impact someone else's life. Am I perfect? No. But taking accountability at least allows you to have sympathy and empathy for the human experience that's around you. Almost without fail, I will discover the truth of how somehow I was responsible for what is happening to me. Then you realize what feelings are real and not real. You realize, "Okay, this frustration is just completely made up. I am manufacturing it." **Jackson:** And as soon as you take accountability, it's frustrated. **Cyan:** It is frustrated. But once you realize that, it just dissolves. Then you're like, "Wow, if that could dissolve, what else could dissolve? What else is real and not real?" Start with the thought experiment : I am responsible and to blame for everything. **Jackson:** But it also manifests in this radical freedom to act, which is one of the reasons why you've been able to do so much. ## [00:56:28] Randomness, Faith, and Experimentation **Jackson:** I talked about agency briefly. I know you love \*The Matrix\*. In \*The Matrix\*, Morpheus is continually offering Neo these choices to escape or be free—to be agentic. You are clearly a wildly agentic person. You've done amazing things, you're really good at making decisions quickly, and you're wildly accountable to yourself. You also are really into randomness and coincidences. A couple of quick quotes. You say, "I treat coincidences like the glitches in the matrix. If you see the same cat twice, pay attention." And then, "My life has only been improved by taking myself out of the decision making process because I am a hindrance." **Cyan:** Yes. **Jackson:** You've talked about randomness being this way to break up our bad patterns. It's a healthy, cool thing to roll dice to do things. You've said you don't like the word "believe" and you prefer "suspect." And you're wildly experimental and iterative. I'm not sure that they're actually at odds. But on the surface, there's a notion that this letting go and randomness—the idea that "I'm not the decision maker"—is at odds with conviction and agency. So my real question is : what is your relationship to faith? Is faith what's happening here? **Cyan:** It is a kind of faith. You're trusting that if you step off a ledge, you're not going to fall. Going back to the tarot card, I'm the Fool. You're also trusting your conviction in feeling or knowing on a level that defies logic. For example, I have all of these things that just magically happen. The world speaks to me in poetry. If what I just said doesn't make sense to you, that's fine. If you go back to Plato's cave—if you're in a cave and everybody tells you that there's this world outside that can speak in poetry—it makes zero sense. Whitman used to make no sense to me in Blades of Grass, until I started seeing the poetry everywhere. I always say "suspect" because I can't tell you that I know how any of this works, but I think there's a non-zero chance that we're in a simulation. If you take this thought experiment out and say there's a simulation, then obviously there's an architect of some kind. Call it God, an engineer, a magician, whatever you want, but there's something that started the simulation. What could that something be? You start thinking about it. The only thing that's perfect in the universe is nothing. So maybe that something is nothing. You start going down that hole and start thinking about it. Then you also start thinking, if I'm in a game—this game called Life—there are rules to this game. I'm a hacker by background. I come from a security background, and I hung out with hackers. I like to poke holes in things. What happens if you go left instead of right? What happens if you introduce dice? What happens if you analyze a thought and wonder if it's yours? What happens if you look at a sign, you feel something, and you decide to follow whatever that sign says? What happens if you stand in one spot and you do nothing at all, but just stand there for hours? Does the person that you most want an answer from suddenly walk up to you? You won't know until you try these things. And I have. **Jackson:** And so every time you choose to try them? **Cyan:** In many ways, yes. **Cyan:** There is agency and there is conviction in these things. It looks like there's no conviction, but it's actually really strong conviction in something that's seemingly insane. I'll give you an example of what might look insane. I decided at an A16Z speedrun the other day to just say it, because it's what I'm doing right now, and it's working. They asked how I get deals, and I said, "Well, I'm going to say something nutty, but lately I've been daydreaming." I think about how the world could be better, I think about what people could be creating, and I imagine it in all the various ways I can with my perception. Then I let go of my attachment to it. Because I used to be a founder, I used to think, "I want to go build that. I want to do that," or give it to a friend. Instead, maybe I'm giving it to some kind of collective subconscious and putting it in a cloud. Maybe someone gets that spark, and maybe they decide that's the company they want to build. Then maybe they show up on my doorstep, and then maybe they tell me exactly what I want to hear : what I want to invest in. It turns out that's been happening. I don't know if this is how this is happening, but I know that I think about something I want to invest in and it shows up. So do I really need to go out to every demo day? Do I really need to grind away and look at every presentation? Or do I need to daydream? Do I need to make believe? Do I need to use my childlike mind? Then suddenly, someone is inspired by that thing or independently has nothing to do with me, and they just show up. I just happen to be good at timing. I don't know. But I know it's way more fun to live this way, and it doesn't harm anyone. I'm finding deals, writing checks, and I'm really excited about these companies. It feels a lot different than my early career where I just went to party after party, grinded, and went to demo day. You can't argue with some of my results. I did well back then, but I'm still doing well with less of that now. Maybe it's because my brand profile is stronger or I'm more well known. There's a lot of factors I have to factor into this. But I do think that some of the experiments I'm running have nothing to do with my job. I'll just say I want to meet an artist, and suddenly within a week, I'm talking to that artist. Not because I sent an email, not because I contacted an agent, but because I ran into them at Starbucks. When you start getting into this and it gets really weird, possibly the simulation is conspiring in your favor. And if so, how do you affect that? How do you impact that? It turns out words had weight. My very first observation of humanity was that words had weight. So what we say about ourselves and the world around us changes our perception of it and quite possibly the reality of it itself. **Jackson:** Casting spells. Correct. Attention. **Cyan:** Again, this is all theory. I never like to say that I'm a guru or that I believe these things, but I experiment with them and I get repeatable results. So I don't know what that is. **Jackson:** It's funny, there's this phenomenon with technologies or inventions where they show up in a few different parts of the world on the same time horizon, arbitrarily or without coordination. It sort of feels semi-connected to that. There's one bit of this that I'd love to ask about. You were telling this very crazy story about Tim Ferriss going to Boston. **Cyan:** Oh, yeah. **Jackson:** There's a part in the story, and this ties into faith, where after the game, this whole trip is you purely following the signs. You go back and you try to charge a candy bar to the hotel room. I was driving in the car a couple of days ago, relistening to this, and maybe hearing this part for the first time. The person looks you in the eye and tells you you don't exist. **Cyan:** Yes. **Jackson:** While I was listening to this, I got a chill down my spine. It was a bit like the fear I had when I was alone in the house at night as a kid. It was fear, almost a spookiness. What it prompted for me is that you have a lot of faith and you're trusting. It goes back to the cliff analogy. Is fear a part of this? Are you just totally at ease with it? **Cyan:** I'm trying to ditch fear. I'm sure you've watched or read \*Dune\*. Fear is the mind-killer. It limits you. I think we have very little to fear. The more you go down this path of self-discovery or spiritual work, you fear death a lot less. You fear change a lot less. You embrace it; you welcome it because it's a lesson. Every bad thing that happens to me is now a lesson. And that's exciting. So it's like, okay, this shitty thing just happened. What was I doing? How could I correct that next time? And what can I learn from this situation? **Jackson:** It's more of an infinite game. **Cyan:** It's an infinite game. ## [01:06:22] Conviction and Peter Thiel **Jackson:** One last note on the conviction front. You used the phrase a few minutes ago where you talked about feeling and knowing. You've talked about your departure from Founders Fund, dating back to this conversation with Peter where he pulls you aside early on. He says: "Cyan, you're really good at feeling, but I need you to get better at knowing." **Cyan:** I've asked him for clarity on that recently, but I didn't get a response. Sometimes people can teach you with silence. **Jackson:** There's another anecdote from Founders Fund, which I think is from Kevin's piece, around Niantic. You had angel invested in Niantic, Pokémon GO. There's this back and forth and this little excerpt where Peter finally bends and he says, "'This is a one-time deal just for Cyan,' Thiel told everyone else in the room, 'No one else can ever do this again.'" This is a specific allocation of how much money you got from your personal whatever. "Banister smiled at the memory. 'People don't know what to do when you have that level of conviction,' she says." **Cyan:** A bit theatrical sometimes, but sometimes you've got to make a point. **Jackson:** I'm curious about those two things. I'd be curious for you to reflect on the difference between feeling and knowing, to the extent you still feel there is one. Peter Thiel is a person who has deep, deep conviction as well. **Jackson:** I'm curious about your conviction and Peter's conviction. Could you compare or contrast or just reflect on that dichotomy and what you learned from that? **Cyan:** Peter is religious, and I think a lot of people may not know that. If you talk to him about his beliefs, they're the most unique set of beliefs I've ever encountered. It's really interesting because when he's trying to solve a problem or thinking about what to do, he will often close his eyes and stay still for long periods of time—way past your comfort level. I usually tell people if you meet Peter and he does that, give him space. Don't try to fill the space. Let him do it because it's a gift. When he does that, he's never verbalized what he's searching for, how his thought process works, or how he arrives at something. But every now and then, he'll open his eyes and just say, "We're going to do this thing." It'll sometimes be the most jarring, possibly life-altering decision with crazy amounts of money that you're just like, "How did you come up with that decision that quickly?" I've seen him do that over and over again. But interestingly, people are mirrors. I do the same thing. The first thing was we were coming back from an investment team meeting and he offered to give me a ride back to the office. The ride was mostly quiet. Then he said, "Cyan, I want to tell you something." I said, "Okay." And he said, "You're really good at feeling, not so good at knowing." He looked at me, and there was this unspoken, "You got it?" Nothing else was said. I didn't ask any questions. I just looked at him and said, "Got it." And he goes, "Okay." His house was very close to Founders Fund; it's a five-minute ride. Then he dropped me off in front of Founders Fund and said, "See you later." That statement kept me up for many, many nights because I was wondering what kind of knowing he was talking about. This was before my spiritual moment in Boston, before understanding that there is a type of knowing that is not words—that feelings can be knowing. How you can know if a feeling is accurate or not takes a level of discernment and understanding your inner world a bit more than I did at the time. I asked him a clarifying question recently, and he didn't respond yet. Maybe he'll respond someday in person. I said, "Were you talking about financial acumen?" Because that's the way I took it. I took it as I have to become a data room junkie, get better at spreadsheets, and be able to rattle off numbers to justify my decisions. I have to become more quantitative. But what if he didn't mean that? I don't know now. I actually don't know what he meant, but it did result in me quitting. The ego gets in there, and the ego's like, "Wow, you are terrible at looking in data rooms and quantifying your decisions." There's this bizarre path that you take to get to where you are. To even explain to people how I arrived at a decision is just exhausting. You just can't. I took it as I need to go follow my path and do what I'm good at, and unapologetically so, because that's what I like to be. So I resigned. It was that one conversation. Peter has this surgical precision that he can deploy at any time where he gives feedback, and it's just really profound. He's one of the best teachers I've ever had. The Niantic thing was really great. At Founders Fund, we had this thing called a sub-fund, and you got special privileges on anything you invested out of that sub-fund if it did well. Once you were in the money and you returned the money, then there were these hurdles—multipliers that were much more attractive than the main fund if you did it out of there. What Kevin wrote about was, I told Peter I wanted to take my whole sub-fund and put it into Niantic. **Jackson:** How long you been there at that point? **Cyan:** Two or three years. I'm not a growth stage person. In hindsight, Niantic's done well—it just sold to Scopely—but that investment was not a fund returner. Every investment you make should be a fund returner. He was right about the economics, and I could have learned something from him in that situation. They didn't lose money; they made money. But that level of conviction can come across and help you when you know you're onto something and you want to move something forward. It was like a poker table, and I was going all in. He had everybody sit down. He said: "Okay, sit down. This has never happened before." And he did say, "Never again. No one else is doing this." One time, I drove the LPAC crazy at Founders Fund. I'm notorious for being the person who broke the most rules. If there are boundaries, I will test them all. **Jackson:** That might have to come on another podcast; I'm sure there's a lot there. ## [01:12:54] Returning to Seed Investing and Long Journey Ventures **Jackson:** This leads into the decision to leave and return to what you knew you were great at. You've said: "We like to think we can do anything, but at some point, you have to face reality when you can't do something. And when you can't do something, you should realize what you are really good at. So today I'm going back to that." That was right when you left. This ties to what we were talking about at the beginning of the conversation. In an interview, you said, "I wish I had a thousand of me. I'm just so curious. I wish I could live all these lives. I wish I was scalable." **Cyan:** I still wish that. **Jackson:** I'm sure you do. On one hand, it's not mutually exclusive, but returning to seed investing was like returning to something. Obviously, you're building a new firm and you guys are doing great, and it's new in a lot of ways. I'm curious what that was like to return to something you knew. Maybe I'm conflating things, but it gets into this notion of life where you keep climbing the ladder and you keep climbing new ladders. This was maybe a horizontal ladder rather than a vertical one. I'm curious what that was like. **Cyan:** This was a strange shift because as an angel investor, for the most part, I can get on any cap table. There's no competition. I can just walk in and say, "I want to be in this company." And most people are excited or happy to have my name on the company, which is great. It's such a privilege and an honor to be that person. But when you're with a fund, it's different because a fund has a lot of responsibility for whether they follow on, what kind of signal that sends, and it implies that there was a consensus between the partners. It implies a lot. Deciding to strike out and start a venture fund with Lee was a decision I had to make because I wanted to grow. I could be solo. I can deploy my own capital and run my own fund. But you don't get that water cooler thinking, you don't get that team that you can bounce ideas off of, and you don't get a chance to have people point out your flaws. One of the things I love about Long Journey is we have a coach and we are constantly pushing each other to be better people, to resolve conflicts, to think about our egos, and the types of things we want to invest in. Even the LP base that we have is all intentional. A lot of this is an exercise in consistency, which I told you I'm terrible at. I have to show up every Wednesday. I have to be in the standup Tack meetings, which is what we call them—the absurd committee where we decide what we're investing in. I have to show up on Mondays for the standup. I have to do things that are very uncomfortable and unnatural for me in order to build this organization. And I do want it to exist long after I'm gone, if it's possible. Those types of institutions are hard to build and everything's impermanent, so eventually everything will be gone. But if I could infuse some of this randomness and this thinking in my spirit into a form of capitalism, that would be really cool, because I do think I'm a contradiction. People like me typically are not capitalists. They don't love venture. I'm deeply aware that normally an artist-type person like me does not get involved in a field like this. I think there could be a different way to do it and there could be a different way to enjoy and love capitalism and to see it in a different light through a different set of lenses of how it can actually reshape the world. **Jackson:** There's something cool about that. Investing for yourself, investing your own money, and joining an existing firm are both great, but there isn't that thing you spoke to, which is actually starting something and building something that might be able to endure and compound. That's cool. **Cyan:** I'm getting ready to write a value around this for our site and for our firm, which is called Win-Win-Win. The idea is that for every minute that you spend in your life, what if you could compound it and make it more impactful? For example, if I'm investing a dollar into a company, I'm not just investing a dollar; I'm investing a dollar on behalf of institutions and nonprofits that are trying to solve some of the world's most difficult problems. Then I could get the returns, and I am a philanthropist who can give that money away in the end of my life, which I plan on doing anyway. There's another compounded win. Then you think about all the people that are going to have jobs because of that dollar or what that company's going to solve because of that dollar. You've added another win. You just write down all the wins, and the more wins the better. You're really maximizing your time for the dent you're going to leave in the universe. ## [01:18:23] Thoughts on Art **Jackson:** I want to talk a little bit about art. It came up earlier, and you've talked a lot about it. You brought up the notion that art has this way of finding you when it's supposed to. I think the first time I heard you mention that was about \*American Beauty\*, which is a crazy movie that had an impact on you. You've also talked about the feeling of seeing yourself in a painting. I think it was specifically Bill Murray or a specific film. How rich that is. Two other quotes. One, you say, "Art moves the needle on culture and opens people's minds and hearts to subjects they otherwise might not have thought about." And then you say, "Business is art. The US Constitution is art. Contracts and code are art. Capitalism isn't just an idea. It's art." What are the bounds of art? What kind of art moves you most? **Cyan:** I really like the unsung hero art that's on the fringe, that doesn't see the light of day, that hardly anyone knows. That stuff I really, really like. In that sense, for example, the US Constitution is something that impacts us all day to day. It is a conspiracy that everyone in this country, for the most part, agrees to. And it is the prevailing laws that keep everything in order, to some extent. But it's just a document with some words written in ink. We've all decided that we're going to uphold it with something called belief. We believe in this document. And if you think about the power of that, it is one of the most powerful pieces of art on the planet. It's worth defending, it's worth interpreting, it's worth valuing, because there's no other country in this world that has something like it. America is an art experiment. We're young. We have not been around as long as other countries, and we are now reaching a point in history where we're going to have to test that document. We're going to have to see whether or not the branches of government we have and the types of powers that were envisioned by our forefathers actually hold and whether or not we will have freedom of speech. We can't have freedom of art without that document. I think very deeply about the Constitution and about how it gives us certain freedoms that I think are human rights, that don't extend to other places, and how those freedoms are being eroded and what the implications of that are. Because I view everything as art— **Jackson:** Everything? **Cyan:** Just about everything. If you look around this room, everything in this room was created by a human being. And that human being contributed their experience of it potentially to a collective subconscious, and so they made it a reality. But if a tree falls in a forest and no one's around to hear it, did it actually fall? Does this room really exist? Or are we conspiring to keep it in place because we accept it as reality? This is art, too. You may say it's uninspired. You may say it lacks meaning. But that's not true. Someone could come in here and the walls remind them of something from their past, and it opens up a whole new gateway and an understanding of life that they never had before. It's such a subjective experience, art, that I'm hesitant to say what's good art or bad art or what's art and what's not, which is one of those arguments that everyone has. But some art is more impactful than others. Some of it deeply, deeply moves us and changes us as humans and allows us to try on those different lenses to perceive life in a different way. The most successful art can do that. I'd rather talk about art as successful art versus unsuccessful art, because some of it's just unsuccessful. It's an attempt. **Jackson:** It prompts something. **Cyan:** It didn't land, but sometimes it gives birth to its final form. Maybe it's just the throwing of the clay and eventually it becomes the pot, but you've got to start somewhere. You've got to throw. I always marvel at ceiling fans. There's some person who looks at a ceiling fan and says, "The world needs another ceiling fan." It's a problem that we've solved, but yet we somehow aesthetically want a different one, or a spoon or a glass. Those are the entrepreneurs that blow my mind. Who are you and why are you doing this? Because it's really a race to the bottom. I marvel at you. I want to meet these people. But there's an example of a piece of art that someone wanted to will into existence in the world: the ceiling fan. **Jackson:** John Collison has this line that the world is a museum of passion projects. **Cyan:** Yes. **Jackson:** Which captures the upper echelon of that. But it's true. **Cyan:** It's very true. ## [01:23:42] Peformance Art **Jackson:** Why do you love performance art? **Cyan:** I love performance art because it goes back to that childlike wonder. We wear clothes that allow people to form a quick opinion of you. If you wear a suit, you might be a professional. If you wear a doctor's outfit, you might be medical. If you are wearing a fast food uniform, somebody might make assumptions about you. I like challenging people's assumptions and pushing people to wonder. You use these things just to get along in society, with culture, and with people around you. To be a neighbor, you sometimes have to make very quick judgments. But which judgments should you challenge? Sometimes I'll go into a really fancy store on Rodeo Avenue wearing clothes that look like I'm a bum to challenge their assumptions about me. I wear fast food uniforms on golf courses. **Jackson:** Specific brands? **Cyan:** IKEA uniforms are the best. They're the funniest. They're blue and yellow, and you can really see me out there. This was inspired by a friend of mine who played golf with us one day in Las Vegas and didn't have an outfit, so he wore this red polo. My friend kept calling him Target. I thought to myself, "What's wrong with Target employees' outfits?" That could be a whole thing. I started buying all these Target employee outfits. I have Wendy's, Taco Bell, and a bunch of McDonald's uniforms. **Jackson:** Wow. Talk about cultural appropriation. **Cyan:** If you go into a golf club wearing a McDonald's fast food drive-in outfit, they're going to tell you that you can't have it. But if you push them on it, it has a collar. These are chinos. If it's good enough for McDonald's, it's good enough for here. It doesn't break any of the dress codes. Maybe you have to force them to update the dress code that says, "No fast food uniforms." That's your contribution. I'm not always doing performance art, but every now and then I am. It allows you to play with the world a little bit, to bring some levity to a situation, or to teach people how they can play. **Jackson:** Did you get into golf after you met Bill Murray? **Cyan:** The day I met Bill Murray. **Jackson:** But in that story, you said you'd never played golf. You now play. **Jackson:** You play enough to have robust fast food uniforms? **Cyan:** I play enough to be silly and to have fun on the golf course. I've made two pars in my life so far, which is not a lot. **Jackson:** We'll take it. ## [01:26:37] Cyan's Creative Projects **Jackson:** You said you want to make a piece of art, something like \*Song of the Lark\*, which is a reference to a painting that Bill Murray talks about. "I don't know if it's a building, a painting, a film, a sculpture, a piece of theater, or what. Something that moves people." We talked a little bit about this with magic glasses. I know you've been working on a number of film projects. You could literally answer the question, what are you hoping to make? But more specifically, I'm curious what you're hoping to say. **Cyan:** I don't know what I'm hoping to say yet. With magic glasses, I want the end result to be that you wonder which pair of lenses you're looking at the world through, and could you change them? If you walk away with that concept alone, then we've done our job. Or if you said, "That's the weirdest movie I've ever seen. What did I just watch?" that also could do the job. There are other stories I am exploring around euthanasia. I am fascinated by this concept of the right to die. When do you have that right? What are the religious, spiritual, societal, and contract implications of an adult person deciding they want to do this? A couple of the stories I'm working on explore those topics pretty deeply, and I'm really excited about those. **Jackson:** Why are you drawn to that? **Cyan:** I'm curious about life and mortality in general. I don't fear dying. I don't welcome it and I don't want it; I want to experience as much of this life as possible. But I'm very comfortable with it because I have a unique understanding of what my life is now. I understand why I'm here, or at least I think I do. Because of that, I want to explore if someone is just ready to check out and they're done. If they waited five years and could convince a psychiatrist that they've really thought about it, should we allow them to do it? Under what circumstances should that be allowed? Terminal illness, deep amounts of pain, suffering. We allow it for animals, but we don't allow it for humans. Is there an honest exchange in which two consenting adults could, like Romeo and Juliet, take each other's lives? I'm exploring it with a story that involves an elderly couple as well as a young woman who you would think has absolutely no reason to take her life. She's not sick; she's not anything that you would imagine. It explores the moral implications behind that and will hopefully challenge somebody's feelings about mortality and when it is okay to take a life, or your own. It's a little Dexter-y. It's not a horror film, but it does involve some horror. That's one that I'm working on. The other thing is, I like the idea of creating fake stores. I haven't done this yet, and it's a fantasy that I want to do. I like the idea of a shopping experience that isn't what it seems. **Jackson:** Okay? **Cyan:** Maybe it takes a while, like boiling the frog, for you to realize you're in something that's not real. Then you wonder, are these products real? Is this something I can use? It makes you question reality or your purchasing choices. There's some vein there that I'm exploring. The most controversial thing I've come up with is a robot brothel. **Jackson:** Okay. **Cyan:** Someone has tried that in Japan or somewhere. **Jackson:** Now is the time. **Cyan:** The idea is that it's not real. I'm giving it away, so it doesn't really matter. I probably will never do this. This is a fantasy that I had, which is you rent a space in San Francisco, someplace where there's libertine people, where it would be expected to exist. Not like Marfa, Texas. You put it here, and if you look through the window, it looks really legit. It's got a phone number for making appointments. Then maybe people come and go and they act really weird. You create this lore that this thing exists, but it really doesn't. It's just to test the idea of how society would feel about the legalization of an AI robot who is not human. Is there a rights issue? It's just to really explore that concept. **Jackson:** Performance art. **Cyan:** It's performance art. Those are the types of things, and I've got a long list of them. That's just one of the many things I would like to try, including parties that are fake and protests that are fake, just to start a conversation. I really love billboards. There's a group of artists that make these really confrontational and funny billboards that make you think. I like Confusion marketing. It's a type of marketing that makes no sense. Some religious person put up these signs that said they were from God. And it was like, "You think it's hot here? Try hell. - God." But it doesn't say which church did it. It really gets you thinking. You're like, who did this? And why? And why that font and why here? Anything that jolts someone out of the reality they think they're in into a new one is my goal. **Jackson:** My friend Peter, you would like him, started this thing called Birds Aren't Real. **Cyan:** I love Birds Aren't Real. I discovered them because of a sign on a telephone pole, and it said, Birds Aren't Real. I think it was in Flagstaff, Arizona. I was looking at it, and that is hilarious. I went to the website and bought all the shirts. **Jackson:** It's world building, right? **Cyan:** Stickers. **Jackson:** Very Andy Kaufman. **Cyan:** That's a great artist group. Hats off to your friend. Big fan. **Jackson:** I have a smattering of miscellaneous topics before we wrap up. **Cyan:** Okay. ## [01:32:51] Boredom **Jackson:** When we met, we talked about boredom, and I think we disagreed a little bit. You have a line from your sister where she says being bored is an insult to your intelligence. **Cyan:** Yes. **Jackson:** I had brought up the notion that I'm trying to be bored more. You said earlier in the conversation that you're never bored. Why are you against boredom? Can we redeem boredom? **Cyan:** I've been thinking about that conversation since we had it, because I was very combative with you and very adamant that being bored was not a good thing. And then I have to question that, because every belief that you hold or any assumption that you hold, you should challenge it. You are challenging it, and I'm challenging yours. It's a fascinating exchange where there's this tension, and both of those things could be true, and we have to hold them in tension. I was very bored when my sister said that. And I really wanted to be intelligent, and I prized that as a trait that I should have and should strive to be. When she told me that, I was determined from that day forward to never be bored, because I realized it was a choice to be bored or not bored. I do things that other people would find boring, which is the dereve I was telling you about, where you drift and you walk around. Because I'm always observing, it's almost nearly impossible for me to be bored. But somebody else might call that boredom. I don't have the feeling of boredom. I'm not even sure I can get it anymore. I'm not even sure it's possible for me. **Jackson:** I think, to be honest, when I say boredom, I'm pointing at something more like dérive. I am pointing at this deliberate idleness that can open up. **Cyan:** We agree that intentional idleness, intentional drift, is a very good thing. I think when you sit around and allow yourself to wait, procrastinate, and feel all these horrible feelings that come along with boredom just to get an epiphany of what you should be doing, that is self-destructive. But maybe someone could make an argument that it's not. You have limited yourself so much that you're waiting for that aha. As long as you get it. **Jackson:** You're never bored when you're meditating? You said you can meditate for six hours. **Cyan:** Six hours or more. **Jackson:** Not bored at all. **Cyan:** Not bored at all, because there's so much to observe. **Jackson:** The difference between you and a normal person is that you can find something to observe in any context, even if you're alone with yourself in the dark. **Cyan:** Yes. I love it when people are late for a meeting. I think it's great because I can spend all this time observing and being with myself. Not that I want everyone to cancel meetings with me, but I do love it when it happens. I love that time being reclaimed where I can do what I love the most. It's impossible for me to be bored. ## [01:36:06] Living Around Elderly People **Jackson:** You live with a bunch of 70- to 90-year-olds, or maybe you used to. **Cyan:** I still do. **Jackson:** You still do. You said, "This is perfect content for my retirement community. (Yes, I deliberately live among seventy to ninety year-olds. That's another story, but picture an intentional living space where artists and free thinkers can keep being reborn)" which is beautiful. What has been unexpected about living with a group of people in that age group? **Cyan:** Some people don't plan well for their end of life, and so they're financially insecure. You see that across the board. Sometimes they can model behaviors for you. There was this woman who died when she was 93, named Jane Anderson. She was an amazing woman and was fiercely independent to the very end. You could not take her keys away for her golf cart. The biggest danger was trying to keep the keys away from her car because at some point she drove the car on the golf course. That's a little dangerous. Eventually, you start to lose touch with what you can or should do. That problem happens in communities like this; sometimes you lose touch with reality. I've witnessed with Jane that she saw people, she was able to predict that someone was coming over before they came over. She was talking to people that we couldn't see as if they were there. She was saying really profound things that were very meaningful. You can't get those experiences unless you're in that community and can be there at the right time to witness these amazing end-of-life stories. She was so inspirational to me. She was the first female golfer to ever play co-ed competitive golf, so she broke ceilings. If you asked to carry her bag, she's like, "No, thank you." She was unapologetically Jane. She was fierce, but also very kind. She was a schoolteacher and an amazing role model. In the end, I had dinner parties with her with invisible guests. I put out plates and food, and we were having the time of our life. I really enjoy this. This is why I spend time intentionally around an aging population. Health is the great equalizer, and we are all going to die, or at least our bodies are. We could spend more time, especially as entrepreneurs, analyzing what that end-of-life care looks like and how much a community can take on. We tend to take a person who is difficult to take care of, put them in a home, and make it someone else's problem. With Jane, that didn't happen. She did have an in-home caretaker, but for the most part, the community really did rise and make sure that everyone came together like neighbors. One of the neighbors who really valued his friendship with her built her a big window, for example, so she could look out on the golf course. People could come in and say hi to her while they were out there golfing and keep her company. People all through the community would bring her milkshakes or stop by and sing to her. I honestly think until her last breath, she lived a very good life. That's what I want for myself, for all the people I love, and for people I don't know. I still love you. I want it for you. I want people to experience this if they're not going to be taken out in a car accident or something like that and you have the privilege of being able to decide how you die. It goes back to the euthanasia stuff. Why wouldn't you put a bit more intention into it, and joy, and community? For example, we're building a drive-in movie theater for golf carts with the old little talk boxes that you can roll up to. **Jackson:** So cool. **Cyan:** We have a movie theater screen. The idea is if every house contributed an activity like that, imagine you won't need a clubhouse or a management team. You could just say it's Taco Tuesdays over at Rob's house. Or there's a tiki lounge in a tree that's only open on Thursdays. Someone can open an underground jazz club. The other thing I love about older people is they remember how to be kids again. **Cyan:** Because they give no Fs. They're just : We got five years left. Let's make the most of it. **Jackson:** I think there's a lot all communities could learn, especially from those last few things you said. We can just do Taco Tuesday at Rob's house. **Cyan:** You can. **Jackson:** You don't have to be in the old folks community either. **Cyan:** You just can. I'm looking forward to people figuring this out. These unconferences, Edge Esmeralda and Deep Tech Week, put together all of these events that are happening all over the city at different people's houses. It forms a decentralized event. There's no reason why we can't do that as a society. I'd like to prove this out as a concept. The hardest things have been disputes between individuals. When you form a community, there are people that you can't ask to leave. They live there. **Cyan:** If they start not getting along with you or they start drama, how do you navigate drama? It's tough. It's really, really tough. That's one thing that I have not enjoyed about it : the people issues that can arise. If everyone could just get along, that would be really amazing. ## [01:42:14] Pete Buttigieg **Jackson:** This is a quote: **Jackson:** "I get paid to see abnormalities in the marketplace. Pete Buttigieg is an outlier. I knew the moment I met him that he was going to be president one day." **Cyan:** I still think he is. **Jackson:** What's special about him? **Cyan:** I went on this tour when I worked at Angellist or Founders Fund. They called it Comeback Cities. We went to Flint, Michigan, and Detroit, and South Bend, Indiana, was one of the stops. **Jackson:** This was Founders Fund. Apparently you tried to get a Founders Fund office in South Bend. **Cyan:** I did. It was Founders Fund. I went to South Bend and part of the tour was meeting Mayor Pete, and he showed us these data centers he was building at the time to mine bitcoin. He turned a car company plant into a data center. We went in there, and it was great to see a public official understand how technology works and how he should be investing in bitcoin back then. Think about what it's worth now. The other thing was getting rid of blight. This is controversial, but the city would buy back certain types of land that was in disrepair. They could free it up to become yards for buildings that were aesthetically better looking, which gets rid of the blight. If people don't live around blight, they naturally care for their communities more. You start to see the quality of those communities go up because there's not a pile of rubble that no one can afford to take away. He took away all of these dilapidated homes that were falling apart; the city would buy them and take them out. He also turned the city into a beta test, and he was very proud of it. A lot of the scooter share programs started out in South Bend, and he quickly identified that the unbanked couldn't use them. Then they had to develop a solution. When some college kids wanted to figure out how to do water filtration, he gave them use of the entire city's water filtration. **Jackson:** Very experimental. **Cyan:** Very experimental. The thing that impressed me the most was his ability to say, "I don't know." I would ask him how he was going to solve a problem, and he'd look at me and say, "Cyan, that's a very good question. I would bring in panels of experts, I would talk to as many people as possible, and I would try to get to the bottom of it. But to be honest with you, I don't know." And I thought, wow, how refreshing. **Jackson:** That's pretty rare. **Cyan:** It's so rare. Most politicians will tell you whatever they think you want to hear, and they lie. All politicians are flawed, including Pete, but I'll take a person who will admit that they don't know any day over anyone else. He was a military person, so he understands what it means to carry a firearm and what it means to be sent off to war and possibly killed. If we're going to be sending our sons and daughters off to war, we should at least understand what it's like. I would love our commander in chief to be trained by the military and to have served. Trump did not serve. It makes me uneasy when someone can make decisions that cost taxpayers tons of money and also cost lives without ever having to experience that themselves. ## [01:45:57] Being a Role Model **Jackson:** You were talking about \*Halt and Catch Fire\* and seeing yourself in Cameron Howe. You said : "My hero is a woman on the show, \*Halt and Catch Fire\*, named Cameron. She's the first character I've ever seen that when I'm watching her, I feel like I'm watching myself." **Cyan:** It was really jarring. **Jackson:** You've talked about having a lot of mentors, but I don't know if you've had as many role models that look like you or that represent where you've been. My suspicion is that you are the real version of Cameron Howe to a lot of young people today. I'm curious what that feels like. **Cyan:** I'm always shocked when people read anything that I write or pay attention to anything that I do, because I don't do it for that reason. When people comment on it or see themselves in me, it's like breaking the fourth wall. You realize, "Oh, that's right. I exist and I'm doing this." With Cameron, her background really echoed mine. Her behavior, how she acts, echoed how I act. I remember watching it and thinking it was a little too close for comfort. But it was remarkable to see myself reflected in art. The only other experience I've had like this was meeting Bill Murray. It was the first time that I saw myself reflected in someone I admired and looked up to. I wanted to know how someone like him could navigate a world and still remain human and present and be among us when everyone wants a piece of him, when everyone's clamoring for his attention. How is he able to be in it with us? And why? That was my interest in him. I have met Cameron Howe, who is Mackenzie Davis. I did ax throwing with her. It was fantastic. She was in Terminator also. Her real-life persona is not like me at all; it's just her fictional persona. ## [01:48:26] Young People's Future **Jackson:** You've talked about helping Gen Z and Gen Alpha feel like they have a future. I'm curious what you'd tell them, especially for those who are feeling lost in 2025. **Cyan:** We need to embrace change because the one thing that's constant is change. Every time we hold something dear and try to become protective of it, it gets ripped from us. This has been repeated throughout history. There have been entire industries displaced by technology or advancements. There's the printing press, the industrial revolution, the train, and the car that got rid of the horse buggy. It goes on and on. Photoshop disrupted photographers. We didn't predict that AI would come after knowledge workers first. If you were to go back in time and ask people which jobs would be displaced first, that was not what they thought. What we're going to experience is ego disruption on a massive scale—probably the biggest ego reset ever—where people are going to cling to concepts that will be ultimately challenged. We live in a world with different ecosystems, different governments, and different rules. If we don't build something or we outlaw something, it doesn't ultimately matter because someone else will build it. When you're in a petri dish like that, and it's going to be done anyway, my recommendation is to accept it and try to figure out what matters in a post-scarcity world. There's a book called The Diamond Age that I would recommend all kids read. I think it came out in 1999. **Jackson:** It's the one with the primer in it. **Cyan:** One of the things he predicts is that everything has AI. There are these matter compilers. You can print this table, I can print a microphone, I can print a chair. It's free. You don't have to pay for furniture. They can print food. **Jackson:** Pure abundance. **Cyan:** Pure abundance. In a world of pure abundance, which is what we're heading towards, what truly matters? Being an artist matters. The age of the artisan is coming. Human creativity, innovation, and production are finite, like gold. There are only so many of us on this planet. When we make things by hand, it's going to be like going to the store and buying organic. There's going to be organic, human-made stuff. **Jackson:** We're obsessed with ourselves. **Cyan:** We're obsessed with ourselves. I think there's going to be more millionaires who create Instagram or TikTok feeds, selling some niche product that they make at home with their hands. I see it all the time. I see people who launch jewelry brands, pants brands, and knitting shops. You see these micro-entrepreneurs. I think we're going to see more of that, and we should celebrate it. Not everyone needs to create a venture return business. They can create a lifestyle business that supports them and their family and gives them abundance, joy, and a sense of purpose because they're whittling spoons or whatever it is that they want to do. Not everyone's going to want something created by an AI that looks too polished or is too perfect. Human imperfection is a beautiful thing. I would recommend that young people do not despair and instead look at the world differently and how they can reimagine it. If your needs are met, what's next? Yes, there's going to be a lot of disruption, displacement, and potential poverty. These are all things that we can get together and try to solve. I'm hoping that we do. It's going to be interesting to see how these multitrillion-dollar businesses contribute to UBI through taxes. I don't know how this is all going to play out, but the world's about to change in a drastic way. ## [01:52:46] Scott Banister and Lessons for Her Kids **Jackson:** What's your favorite quality of Scott Banister? **Cyan:** I think of him as a grandfather clock. He's stationary, dependable, reliable, and an expert at what he does. If he breaks down, you need a specialist. He's my anchor, my tether to this earth. He's the opposite of me. He does not wander around. He's a bit random in his decision-making, and he has very good intuition and a very good gut. But he also indexes high on the logic and financial acumen that I thought I lacked. **Jackson:** That's a pretty good pairing between the two of you. **Cyan:** It's a really good pairing. **Jackson:** The results are pretty good, too. **Cyan:** When we pair us together, it's phenomenal. That's one of our strengths, because he's back office: compliance, legal, all of the various things that I don't enjoy that would take consistency and repetition. Instead, I get to wander around and come back with all these crazy ideas. Our idea of a good time is sitting around eating and talking about businesses and how they work or don't work. We'll talk about how much we love Chipotle because of how many SKUs it has. These are just things that we enjoy doing. The other thing I can say about Scott is he's very principled. He's an immovable object, like a grandfather clock. Once his mind is set on something, there is no moving that man. I like that because it means there are boundaries, lines I can't cross. He has a compass. You know what he stands for, what he fights for, and what he does anything for. I think that's remarkable. **Jackson:** Is there a quality you most hope to instill in your children? **Cyan:** How to learn? I think I've done a good job at that. As long as they can figure out how things are done and how things work, then they're set. If they can figure that part out, then it's just a matter of keeping them off drugs until later in life and preventing them from dying. Then you've pretty much done your job. I hear all these parents say, "I hope I don't fuck up my kids too much." We all fuck up our kids. No matter how hard you try, you're going to fuck up your kids on some level, in some way. That's our job. Our job is to experience trauma on Earth. If we don't experience it, we will invent it. **Jackson:** Part of Earth School. **Cyan:** We will just invent it. ## [01:55:35] "It Just Doesn't Matter" And Who Pulls the Strings **Jackson:** My final question. I have a few things for you before I ask it. First, a quote from you. I think you texted this to Lee: "A traveler lost in a land of endless mirrors only begins the true long journey when she sees not her reflection, but the strings that move her limbs." I was thinking about this quote, and then I was thinking about your favorite line from Bill: "It just doesn't matter." **Cyan:** Yes. **Jackson:** It comes up all the time in Bill Murray movies. Maybe you had this very specific moment with \*The Razor's Edge\*. There's another line from Bill in a Charlie Rose interview where he says, "We used to tell my brother, 'This is not a dress rehearsal. This is your life.'" **Cyan:** Yes. **Jackson:** I was reflecting on all of this. On the surface, "it just doesn't matter" is this nihilistic "nothing matters" idea. As you've noted, that is not what Bill is getting at. If anything, he's getting at the stakes of all of this. It's more like everything else doesn't matter because this does. **Cyan:** Correct. **Cyan:** It's the opposite of what people think it means. I had to try a lot of perspectives to figure that one out. The aha moment I had with one of his "it just doesn't matters" was from \*The Razor's Edge\*. There was a moment where he could have identified with the pain, the suffering, the sorrow of losing a loved one. He could have wallowed in it, and that could have become his identity. But then he decided, "She's gone, she's dead. It just doesn't matter. What matters is right now and the next step I take." And he does that. It's a really profound moment where you realize how much baggage and weight you are carrying around that no longer serves you. Does it matter? If it doesn't, let it go. Until you can truly let things go and you can sever those ties, you will not be free of it. It will weigh you down. That's when I realized what he was trying to teach. It was not nihilistic. A lot of people hear that phrase—I used to hear that phrase—and think, "Do whatever you want because nothing matters." That's not what he's saying at all. He's saying be conscious about what matters and what doesn't matter. **Jackson:** On that note, regarding "the strings that move her limbs:" What is it that does matter? **Cyan:** That's a statement about mechanical thinking and being mechanical. If we go through life just letting other people pull our strings and going towards the whims of others, the whims of nature, or the whims of our sleepwalking, we are not the puppeteer. We're being puppeted. Each mirror, every interaction we have with a person, is a reflection on that reality and a chance to take over to some degree. You can't be the complete puppeteer, but you can take over and at least determine the outcome of your life. That's why I wrote it to him. I'm really impressed that he sent it to you or shared it with you, however you got it. He keeps a file of "Cyanisms," and every time I say something, he files it away and keeps it and will remind me of it years later. That's one of them. **Jackson:** Thank you very much. **Cyan:** Thank you.