#780: Cyan Banister — From Homeless and Broke to Top Angel Investor (Uber, SpaceX, and 100+ More)

#780: Cyan Banister — From Homeless and Broke to Top Angel Investor (Uber, SpaceX, and 100+ More)

Cyan Banister (@cyantist) is a general partner at Long Journey Ventures, an early-stage venture capital firm focused on early and new investments. Cyan was an early investor in Uber, SpaceX, DeepMind, Flexport, and Affirm and has invested in more than 100 companies. Prior to that, she was at Founders Fund, a top-tier fund in San Francisco. Subscribe to Cyan's Substack at uglyduckling.substack.com.

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Timestamps:

[00:00] Start

[06:16] Early life and education as a white minority on a Navajo reservation.

[11:18] Strained family dynamics and a cycle of neglect.

[18:20] The intervention of Officer Pratt and becoming a ward of the state at 15.

[22:46] Crusty punk survival strategies and life on the streets.

[32:02] The positive influence of Cyan's "second" mother.

[34:17] Crass, Chris Collins, and computers.

[38:03] An unorthodox path to angel investment beginning with Uber.

[48:13] Niantic/Pokemon GO.

[56:27] How stalking Garrett Langley led to a Flock Security investment.

[01:00:07] GameCrush, activist investors, and lessons learned.

[01:07:00] Sales lessons from the street.

[01:10:08] A mindful approach to questioning narratives.

[01:15:35] The pre-OnlyFans story of Zivity.

[01:24:44] Views on sex and relationships.

[01:28:47] Magic glasses, esoteric rabbit holes, and rolling the dice.

[01:44:02] How Aleister Crowley and Bill Murray paved a path to ex-atheism.

[02:02:21] Cyan's billboard.

[02:04:41] Enduring a stroke and its aftermath.

[02:08:31] Meditation, throat-singing, and philosophy.

[02:17:50] The Boston spiritual experience and duck boat baptism.

[02:40:53] A book in the works, the Ugly Duckling Substack, and parting thoughts.

*

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#837: How to Simplify Your Life in 2026 — New Tips from Derek Sivers, Seth Godin, and Martha Beck

#837: How to Simplify Your Life in 2026 — New Tips from Derek Sivers, Seth Godin, and Martha Beck

As we head into the new year, many of us feel like we’re drowning in invisible complexity. So I wanted to hit pause and ask a simple question: What are 1-3 decisions that could dramatically simplify m...

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This time around, we have a bit of a different format, featuring the book that started it all for me, The 4-Hour Workweek. Readers and listeners often ask me what I would change or update, but an equa...

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Ben Patrick, better known as “Kneesovertoesguy” (@kneesovertoesguy), is the founder of Athletic Truth Group (ATG), an online and brick-and-mortar training system rooted in rehabilitative strength and ...

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#834: David Baszucki, Co-Founder of Roblox — The Path to 150M+ Daily Users, Critical Business Decisions, Ketogenic Therapy for Brain Health, Daily Routines, The Roblox Economy, and More

#834: David Baszucki, Co-Founder of Roblox — The Path to 150M+ Daily Users, Critical Business Decisions, Ketogenic Therapy for Brain Health, Daily Routines, The Roblox Economy, and More

David Baszucki is the founder and CEO of Roblox. TIME named Roblox one of the “100 Most Influential Companies,” and it has been recognized by Fast Company for innovation on their “Most Innovative Comp...

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