Contrarian Investing and Personal Growth

This chapter explores the concept of contrarian investing, highlighting how unique perspectives can uncover overlooked opportunities. It features a personal narrative about the author's journey in the investment world, discussing the challenges of transitioning between early and later-stage investing. The chapter also reflects on the importance of resilience and personal experiences in shaping an investor's philosophy and approach to empowering others.

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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.

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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.

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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