Ep. 26: Cyan Banister - A Fool's Dérive Cyan Banister (@cyantist) is an investor, artist, and co-founder and General Partner of @LongJourneyVC. Previously, Cyan spent four years at @foundersfund 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. Timestamps: 3:45 - Cyan's "Church" 16:21 - Stillness, Mindfulness, and Introspection 28:47 - Learning to See in Original Ways 39:38 - People: When the "Light is On," "Collecting Minds," and Conjuring Friends 46:55 - Cultivating Childlike Joy and Refusing to be a Victim 52:30 - Radical Accountability 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 --- Quick note on video: Yes, it is here! 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. --- All links and transcript avail below.