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Welcome to this classic episode. Classics are my favorite episodes from the past ten years published once a month. These are n of one conversations with n of one people. There aren't many people like Sian Bannister. She has defied the odds to become one of the great angel investors of this era, and she will get you thinking about the purpose of your work, whether investing related or not. Please enjoy it. Hello and welcome, everyone. I'm Patrick O'Shaughnessy, and this is Invest Like the Best. This show is an open ended exploration of markets, ideas, stories, and strategies that will help you
Patrick O'Shaughnessy is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc.
My guest today is Cyan Bannister. 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 all of this, 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 very early in SpaceX, Uber, Postmates, DeepMind, just to name a few. 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
I absolutely think that spirituality is an investable category, and it's been long overlooked. So I remember when pray.com was raising and everybody thought, who's gonna actually use this? Which target demographic actually wants this? And I think that there are a lot of people, especially coming out of the pandemic, who spent two years wondering why is this happening to us? What is this all about? Why am I here? What is my purpose? And then looking inwards and then looking outwards. And I think people are seeking these answers more than ever before because when you look online and you read wha
How much of your investing thinking does the word contrarian describe? How do you identify with that word related to your investing strategy?
Peter always says Peter Thiel says, you know, it's okay to be contrarian, but you've gotta be contrarian and right. Being contrarian for contrarian's sake is probably not a good path to take, but people have labeled me or claimed me as contrarian. I don't know that I would be self described as contrarian, but I tend to think differently than other people do. And so when I identify an opportunity and I go out and try to convince other people that I found an opportunity and they consistently tell me, no. This isn't gonna work, which usually indicates to me that I'm on to something. I know someth
Before you joined Founders Fund, what did you see in Peter and in them, and what do you think they saw in you?
Well, I dropped out of high school. I did not go to university, and so I always like to joke that I went to Peter Thiel University. And it was a dream come true for me. I was working at AngelList at the time. I was an angel investor. I'd actively been investing at that point for probably about eight years. And when they reached out to me and asked me to join them, three, it was like a Cinderella story. I got to go and work with people that I look up to so much and be able to learn from them and to basically absorb knowledge ev
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