Invest Like the Best with Patrick O'Shaughnessy
Cyan Banister - Investing for a Higher Purpose - [Invest Like the Best, CLASSICS]
25 Apr 2025
Chapter 1: What makes Cyan Banister's story unique?
Welcome to this classic episode. Classics are my favorite episodes from the past 10 years published once a month. These are end of one conversations with end of one people. There are many people like Cyan 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 better invest both your time and your money.
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Chapter 2: How is spirituality seen as an investable category?
One of the things that Justin Maris told me to ask you about was integral family systems. I'm fascinated to know what you've learned there.
So I was talking to Justin and my partner and they said, you really should look into IFS and try it out. So then I tried it out and I went in skeptical and came out realizing, oh my gosh, how amazing is that? For people that don't know what IFS is, you basically view all your parts of your personality as there are no bad parts involved.
Every part is there to serve you, including the ones you might not like. And they come online to serve you because they're trying to defend you and protect you, yourself, that's underneath all of that stuff.
And when you start treating them as separate entities and have curiosity about them and start having conversations with them, you start to realize they're automatic processes that come online that you can then give them other jobs to do. And you can change your personality permanently for the better.
I've gotten rid of some behaviors that I thought were unchangeable through IFS, nervousness, types of nervousness, types of reactions to people talking to me and realizing that these were all just automatic functions of how I show up and react to any kind of perception or stimulus in the world. And it wasn't about the person I was dealing with. It was about me.
In general, it's usually all about how you... handle anything coming at you. A friend of mine said something really powerful to me once, which was, if people are coming with you with anything but love, it's not about you.
Do you still feel fundamentally flawed in any way?
Absolutely. Absolutely. I feel flawed. You're going to hear people talk about when they talk about spirituality, about being asleep and And what being asleep means is going back into your mechanical automatic reflexes of reacting to life and just sort of not being truly present. And if I have a flaw, it's just the flaw of being human and not realizing that I'm not being present in the moment.
And so that's something that I want to grind away at and fix over time. I think that sometimes I can be reactive to things in ways that I wish I wasn't. So I'm working on those things. None of us is perfect. I think the whole experiment of life, if you are an infinite being, let's just pause at this for a moment.
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Chapter 6: How does Cyan approach intuition in investment decisions?
And that becomes very difficult when you're trying to talk to quants or people who think about a world in data rooms and spreadsheets and wanting an answer to how you decided that you want to invest in something because you're trusting your gut or you've thought about the world a certain way, or you've been looking for this answer to appear in front of you may look
To others is if you're impulsive because you want to move quickly and they want to be deliberate and want to get in the data room and want to know more about the company.
And oftentimes at the early stages of a business, you know, very little, you know, that you've got a good founder in front of you, you know, that they have an idea and they have a shot, but all of that data is not going to be there. And so you've got two different types of investor types of minds that And that can be difficult to navigate and frustrating.
It was actually kind of soul crushing for me. I tend to like to be incredibly optimistic. And usually when you get into the quantitative realm of the world, you're dealing with a lot more pessimism. And so for me, I'm an intuitive thinker. And I think that if you're an intuitive thinker and you
have sort of a gut feeling about things and you really deeply think about the world, then early stage is probably the best avenue for you.
So obviously at the time when you joined, you had a ridiculous seed investing track record. We'll talk about some of those companies in a few minutes.
But if you had to abstract away the track record, like the obvious evidence that you were good at doing this, what do you think Peter would have said before you joined about what made you interesting and special relative to say, you know, other people? I'm sure Peter's reference class is pretty good. So qualitatively, what would he have said? Quantitatively, you were great.
Peter gave me one of the best pieces of feedback. One of the things I love about Peter is he's so precise. He can give you like an amazing piece of feedback if you're willing to listen to it and really digest it. And he took me on a car ride one day and he simply said one sentence to me and it changed my life. And it actually led to me quitting the firm.
He said, Cyan, you're really good at feeling, but you're not really good at knowing yet. That was it. And I looked at him and I understood exactly what he was telling me. And I marinated on it and marinated on it. And I said, do I really want to know? Do I really want that skill set? Do I really want to learn these things that are so uncomfortable and unnatural to me?
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