26: Cyan Banister - A Fool’s Dérive

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Aug 20, 2025

Cyan Banister, an investor and artist known for backing SpaceX and Uber, shares her unconventional journey from a childhood on a Navajo reservation to becoming a successful entrepreneur. She discusses the profound impact of music on community and personal growth and emphasizes the importance of mindfulness and self-discovery. Cyan's concept of 'dérive' encourages a playful, childlike approach to life, challenging perceptions and promoting personal accountability. She explores the balance of wonder and responsibility, inspiring listeners to embrace curiosity while navigating adult complexities.

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ANECDOTE

Musical Mondays Became Her Church

Cyan describes how a chance encounter led her to weekly Bobby McFerrin sessions she calls her "church."
She says those sessions restore childlike play, community, and presence that other religion-like spaces lacked.

ADVICE

Start Days By Making Your Bed

Make your bed each morning as an intention-setting ritual and a love letter to your future self.
Use the evening to reflect with gratitude on how that morning intention shaped your day.

INSIGHT

Observe Thoughts To Find Stillness

Observing thoughts, not forcing silence, unlocks deeper stillness and self-inquiry.
Asking "Who is I?" exposes fragmented selves and reveals presence as the only real moment.

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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. 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.

Full transcript is available at https://dialectic.fm/cyan-banister

Timestamps

0:01:23: Intro
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

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