Long Journey Ventures

Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of 1 conversations with N of 1 people. There aren't many people like Cyan Banister. Her life story is remarkable. She was homeless at a young age, dropped out of high school, and five years ago she suffered an extremely rare stroke. Yet, in spite of everything, she is one of the most optimistic and curious people you can hope to meet. Cyan is also one of the great angel investors of this era, having invested early in SpaceX, Uber, Postmates, and Deepmind to name a few winners. She became the first female investing partner at Peter Thiel’s Founders Fund and now invests at Long Journey Ventures. Our conversation is as much about investing as it is about the essence of life and how connecting with that will help us in our professional pursuits. It is also full of awesome stories about people and companies like SpaceX and Bill Murray. Please enjoy this great conversation with Cyan Banister. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by ⁠WorkOS⁠. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. With a single API, developers can implement essential enterprise capabilities that typically require months of engineering work. By handling the complex infrastructure of enterprise features, WorkOS allows developers to focus on their core product while meeting the security and compliance requirements of Fortune 500 companies. Visit ⁠WorkOS.com⁠ to Transform your application into an enterprise-ready solution in minutes, not months. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.  Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: [00:00:00] Welcome to Invest Like the Best [00:04:06] Contrarian Thinking in Investing [00:05:30] Joining Founders Fund and Learning from Peter Thiel [00:11:15] Investing in Companies that Change Lives [00:14:00] The Importance of Overcoming Adversity for Founders [00:16:02] Personal Journey and Choosing Hope [00:20:56] Embracing Curiosity and Wonder in the Face of Adversity [00:21:20] Reconnecting with Our Inner Child [00:24:46] The Interruption and Resumption of the Conversation [00:27:20] The Power of Intuition in Business Decisions [00:32:28] The Story Behind the Investment in Uber [00:38:46] Conclusion: Following the White Rabbit of Curiosity [00:39:08] Investing in Uber: The Beginning [00:41:50] The Impact of Success: Personal Wealth and Privacy [00:50:22] The Intersection of Spirituality and Investing [00:59:34] The Bill Murray Experience: A Lesson in Presence [01:09:54] The Violin Kid: A Tale of Curiosity and Generosity [01:12:43] The Evolution of Investing: A Personal Journey [01:16:34] The Philosophy of Giving: The Universe's Return [01:17:36] The Spirit of a Venture Firm: Founders Fund [01:23:09] The Power of Integral Family Systems [01:28:41] The Trillion Dollar Question: Disrupting Hollywood [01:36:05] The Future of Artistry: AI and Creativity [01:41:39] The Power of Kindness

Cyan Banister

Angel Investor

Long Journey VenturesFounders Fund

(0:00) Welcoming Cyan Banister and David Sacks! (3:23) Behind the scenes of the Besties in DC: White House, cabinet interviews, and more (33:00) How M&A will be unleashed, Google buys Wiz for $32B, Tim Walz on Tesla (49:09) Deep dive on Google/Wiz: breakup fee, impact on VC, ROIC, cloud advantage (1:00:28) Treasury vs Fed tension, Bond markets, consumers, deregulation (1:12:57) Space rescue, SpaceX vs China, lunar landing Thanks to our partners for making this happen: Hims: https://www.hims.com | https://www.forhers.com Gemini: https://www.gemini.com/allin iTrustCapital (use code allin): https://www.itrustcapital.com/allin Follow Cyan: https://x.com/cyantist Follow the besties: https://x.com/chamath https://x.com/Jason https://x.com/DavidSacks https://x.com/friedberg Follow on X: https://x.com/theallinpod Follow on Instagram: https://www.instagram.com/theallinpod Follow on TikTok: https://www.tiktok.com/@theallinpod Follow on LinkedIn: https://www.linkedin.com/company/allinpod Intro Music Credit: https://rb.gy/tppkzl https://x.com/yung_spielburg Intro Video Credit: https://x.com/TheZachEffect Referenced in the show: Bessent interview: https://youtu.be/lSma9suyp24 Lutnick interview: https://youtu.be/182ckTL2KBA https://www.cnbc.com/2025/03/18/google-to-acquire-cloud-security-startup-wiz-for-32-billion.html https://x.com/Tim_Walz/status/1902197581586833643 https://www.nbcnews.com/politics/politics-news/democratic-party-hits-new-polling-lowvoters-want-fight-trump-harder-rcna196161 https://x.com/elonmusk/status/1519735033950470144 https://www.ft.com/content/e6f516e8-2262-44d2-a030-7071b62b0be7 https://x.com/thesamparr/status/1902385138308104685 https://www.wsj.com/economy/central-banking/interest-rates-decision-federal-reserve-ed172223 https://www.cnbc.com/quotes/US10Y https://www.nytimes.com/2025/03/10/technology/eric-schmidt-relativity-space.html https://arstechnica.com/space/2024/11/chinas-long-term-lunar-plans-now-depend-on-developing-its-own-starship https://www.nbcnews.com/politics/elections/steve-kornacki-white-men-white-women-gap-gender-gap-rcna196791

Cyan Banister

Angel Investor

Long Journey VenturesFounders Fund

(0:00) The Besties welcome Cyan Banister! (9:16) Reacting to the LA wildfires: broken incentives, leadership failures, lessons learned (36:51) Insurance issues, rebuilding headwinds, reclaiming the government (59:44) Zuck goes full free speech, fires third-party fact-checkers, opts for Community Notes model (1:20:19) Nvidia goes consumer at CES: market cap impact, most interesting vertical (1:34:49) Why Trump wants Greenland (1:40:05) Conspiracy Corner: Who built the pyramids? Follow the Besties: https://x.com/chamath https://x.com/Jason https://x.com/DavidSacks https://x.com/friedberg Follow Cyan Banister: https://x.com/cyantist Follow on X: https://x.com/theallinpod Follow on Instagram: https://www.instagram.com/theallinpod Follow on TikTok: https://www.tiktok.com/@theallinpod Follow on LinkedIn: https://www.linkedin.com/company/allinpod Intro Music Credit: https://rb.gy/tppkzl https://x.com/yung_spielburg Intro Video Credit: https://x.com/TheZachEffect Referenced in the show: https://www.youtube.com/watch?v=_SQ_myzmV_Q https://www.cnrfc.noaa.gov/awipsProducts/RNORR4RSA.php https://x.com/JonVigliotti/status/1877020919475884110 https://x.com/FearedBuck/status/1877355797245514085 https://www.youtube.com/watch?v=vKJ5WeBc7Us https://x.com/CrazyyHub/status/1823574726738092402 https://www.latimes.com/visuals/photography/la-me-fw-archives-the-1961-bel-air-brush-fire-20170419-story.html https://www.rainmaker.com https://www.ksbw.com/article/california-fire-evacuation-maps/63382651 https://x.com/shaunmmaguire/status/1877366727547433382 https://x.com/WorldTimesWT/status/1876887200526111017 https://x.com/ericabbenante/status/1877207054105886836 https://x.com/laurapowellesq/status/1877143625588682940 https://x.com/jeremykauffman/status/1877128641802285064 https://x.com/deb8rr/status/1877539354802876576 https://x.com/Jason/status/1877183155821494513 https://about.fb.com/news/2025/01/meta-more-speech-fewer-mistakes https://www.americanrhetoric.com/speeches/PDFFiles/Mark-Zuckerberg-Letter-on-Govt-Censorship.pdf https://x.com/townhallcom/status/1876684277787873397 https://www.wsj.com/tech/ai/nvidia-ceo-pitches-robotics-cars-as-growth-areas-to-consumer-electronics-audience-68905f2d https://www.nvidia.com/en-us/project-digits https://polymarket.com/markets/creators/all-in

Cyan Banister

Angel Investor

Long Journey VenturesFounders Fund

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. Sponsors: Eight Sleep’s Pod 4 Ultra sleeping solution for dynamic cooling and heating: https://eightsleep.com/tim (save between $400 and $600 on the Pod 4 Ultra) AG1 all-in-one nutritional supplement: https://DrinkAG1.com/Tim (1-year supply of Vitamin D (and 5 free AG1 travel packs) with your first subscription purchase.) Wealthfront high-yield cash account: https://Wealthfront.com/Tim (Start earning 3.75% Annual Percentage Yield (APY) from program banks on your short-term cash until you’re ready to invest. And when new clients open an account, they can get an extra fifty-dollar bonus with a deposit of five hundred dollars or more.) Terms & Conditions apply. The APY on cash deposits as of 09/26/25 is representative, subject to change, and requires no minimum. Tim Ferriss receives cash compensation from Wealthfront Brokerage LLC for advertising and holds a non-controlling equity interest in the corporate parent of Wealthfront Brokerage. See full disclosures here. 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. * For show notes and past guests on The Tim Ferriss Show, please visit tim.blog/podcast. For deals from sponsors of The Tim Ferriss Show, please visit tim.blog/podcast-sponsors Sign up for Tim’s email newsletter (5-Bullet Friday) at tim.blog/friday. For transcripts of episodes, go to tim.blog/transcripts. Discover Tim’s books: tim.blog/books. Follow Tim: Twitter: twitter.com/tferriss Instagram: instagram.com/timferriss YouTube: youtube.com/timferriss Facebook: facebook.com/timferriss LinkedIn: linkedin.com/in/timferriss Past guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, Margaret Atwood, Mark Zuckerberg, Peter Thiel, Dr. Gabor Maté, Anne Lamott, Sarah Silverman, Dr. Andrew Huberman, and many more. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Cyan Banister

Angel Investor

Long Journey VenturesFounders Fund

My guest today is Cyan Banister. Cyan’s life story is remarkable. She was homeless at a young age, dropped out of high school, and five years ago she suffered an extremely rare stroke. Yet, in spite of everything, she is one of the most optimistic and curious people you can hope to meet. Cyan is also one of the great angel investors of this era, having invested early in SpaceX, Uber, Postmates, and Deepmind to name a few winners. She became the first female investing partner at Peter Thiel’s Founders Fund and now invests at Long Journey Ventures. Our conversation is as much about investing as it is about the essence of life and how connecting with that will help us in our professional pursuits. It is also full of awesome stories about people and companies like SpaceX and Bill Murray. Please enjoy this great conversation with Cyan Banister. Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the only investment research platform built for the investor. With traditional research vendors, the diligence process is slow, fragmented, and expensive. That leaves investors competing on how well they can aggregate data — not on their unique ability to analyze insights and make great investment decisions. Tegus offers an end-to-end platform with all the data you need to get up to speed on a company or market: up-to-the-minute financials, customizable models, management and culture checks, and, of course, our vast and growing library of expert call transcripts. Tegus is changing the world of expert research. Learn more and get your free trial at tegus.com/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.  Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:04:03) First question - Spirituality as an Investable Category (00:06:51) Journey to Founders Fund (00:12:13) Overcoming Adversity and Embracing Optimism (00:14:28) The Power of Authenticity and Curiosity (00:25:28) The Skill of Feeling in Business (00:30:26) Investing in Uber (00:36:18) The Changing Dynamics of Early-Stage Investment (00:39:07) The Philosophy of 'Set it and Forget It' (00:42:24) The SpaceX Story: A Leap of Faith (00:48:02) Cyan’s Spiritual Awakening (00:61:34) Her Story of the Violin Kid (01:05:36) The Art of Trusting Your Gut in Business (01:07:47) The Spirit of Founders Fund and the Future of Venture Firms (01:15:16) What She Would Do With 1 Trillion Dollars (01:24:05) The Kindest Thing Anyone Has Ever Done For Cyan

Cyan Banister

Angel Investor

Long Journey VenturesFounders Fund

Cyan Banister is one of the most successful and renowned early-stage investors of the last decade. Her portfolio includes the likes of SpaceX, Uber, Affirm, Opendoor Postmates, Niantic and Thumbtack to name a few. Today Cyan is a Partner @ Long Journey Ventures, joining the team there following a 4-year stint @ Founders Fund where she led deals in both Niantic and HQ Trivia. Prior to Founders Fund, Cyan was a super successful operator and angel, co-founding Zivity and before that being an early employee at Ironport, leading to their acquisition by Oracle. In Today's Episode You Will Learn: 1.) How Cyan made her way into the world of startups? How SpaceX came to be her 1st angel investment? How that led to her joining the world of VC? 2.) How does Cyan think about and assess her relationship to money? Why does someone believe she had a fear or loathing of money? What made Cyan the capitalist she is today? How does Cyan analyse her relationship to risk? Has Cyan always trusted her own convictions? 3.) How does Cyan think about her own investment decision-making process? What were Cyan's biggest lessons from her experience with HQ Trivia? How did she change how she interacts with founders pre-investment? Why does Cyan never Google someone before meeting? 4.) How does Cyan think about price sensitivity today? Why does she believe there will be a reckoning? How will this shake out in terms of who succeeds and who fails? Why is Cyan in favour of party rounds? How does she think about VCs with sharp elbows? 5.) Why does Cyan believe SF is eating itself? What can be done to reinvigorate the city positively? What can be done to solve much of the homelessness problem? Why does Chesa Boudin never convict anyone? Why does Cyan believe her "BLM tweet is not spicy"? Why is Cyan fundamentally sad and worried for the current state of the world? Items Mentioned In Today's Show: Cyan's Fave Book: Snow Crash As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Cyan Banister

Angel Investor

Long Journey VenturesFounders Fund