26: Cyan Banister - A Fool’s Dérive
Cyan Banister (Website, X, Substack) is an investor, artist, and co-founder and General Partner of Long Journey Ventures. Previously, Cyan spent four years at Founders Fund 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.
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Speaker A: I've been thinking about this, like, 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? Yeah, because we all do. Yes, we all have this. I don't know if you have a mental model of what you were supposed to be when you were grown up, but if you look back, if everybody looks back, everyone would always ask you, like, what are you gonna do when you grow up?
And you might have a fantasy, and 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 stamps 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. And so we create these masks. I chose at a very young age to never, ever give it up. I don't want to ever lose this sense of wonder and childlike curiosity that I have. It served me well.
A lot of my success actually comes from this reckless abandon that I have, and it looks counterintuitive. Like, to a lot of people, they're like, she didn't grind away at university, she didn't follow the path that everyone's supposed to follow, but yet I ended up in the same place. That should tell you something. Am I an outlier, or is everyone cosplaying and afraid? Speaker B: Welcome to Dialectic, episode 26 with Cyan Bannister. Cyan is a hard one to pin down. Formally, she's an investor. She's invested in all kinds of startups, both as an angel investor and as a professional venture capitalist.
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