Invest Like the Best with Patrick O'Shaughnessy
· Patrick O'Shaughnessy
[00:00:00] S0: Well, this essay that I wrote… I'm 40 now – I wrote when I was 28, because I wrote it on the train. I used to commute back and forth from New York City to Stamford, Connecticut. And I was about to have my first child, my son Pierce. And my dad, when I was 21, handed me this book of letters that he had been writing to me since I was born, and a lot of them were when I was like a baby, like the... And I've done the same thing for my son, and it's the same pattern. There's tons of letters in the first couple of years, and then it gets more spaced out, and now I do one on his birthday every year and things like this. And I'm going to give him a packet of letters as well when he turns 21. And I remember starting this process of wanting to write him a letter before he was born. And it got me wondering about, like, "What is good parenting? Like, what do I want to do as a dad?" And I believe deeply in showing, not telling. Like, I think maybe that's another reason I don't like being interviewed. I don't like telling, I'd rather just set an example. But, I was thinking, "What example do I want to show Pierce?" And then I don't remember my exact chain of thinking, but it ended up in this idea of everything I just talked about. So it was born of wondering, like, "What example do I want my son to see and emulate?" Because I'm sure you've learned this about kids as well, they don't do what you tell them. They do what you do. They just copy you. So how you behave is how you parent, and I was thinking about that at age 28 and wrote this thing. And so that's where it came from. So right around then is probably the first time I thought about it.
· David Senra, Patrick O'Shaughnessy
[00:00:00] S1: And then how long from 28 till you realized this is going to be the simple organizing principle of how I'm going to live my life and spend my time? [00:00:00] S0: I actually don't think I could have articulated the principle as I just laid it out until very recently. So I could have told you about the power of Bret Victor's Inventing on Principle starting 10 years ago or whenever I first saw it, but I would not have been able to articulate the principle to you cleanly, and that's because it's hard. It's hard to pin… for whatever reason, it's really hard to pin this down. Interestingly, I've never met Bret Victor. If he's listening, I'd love to meet him. I owe him an enormous debt of gratitude for one of my bigger career successes, which was... I took his principle, not my own, but his principle of instant feedback and applied it as the primary design principle to software that I built in my last business, which worked really well. The software itself worked really well, and the business grew a lot because of the software, and the software worked well because of his principle of instant feedback on choices being made by the user showing up in this case in a visual that described their portfolio. And so I actually, before I had my own principle, stole his principle to great effect, which just goes to show the power of a great principle. But I couldn't have articulated it for a really long time and I can't explain to you why that's the case. I don't know.
· David Senra
[00:00:00] S1: There's a great line from Alan Watts that I always think about. He's like, "People think that life is meant to be understood," and it's like, no, "Life is meant to be experienced." And I find that in my own self. Like, I do think… I can't explain. I have a lot of willie foo-foo part of... I know I always just say that line and you laugh, but I have this willie foo-foo part of me where I just go off feeling, like, an intuition for a lot of things that I do. And I don't want to have to describe why I believe this to be true or why I want to pursue this path or why I think this idea is interesting. I think it's just something inside of me that language cannot describe.
· Patrick O'Shaughnessy, David Senra
[00:00:00] S0: I don't know if it was Alan Watts that said this. He had such a way with words that maybe it was him. It might've been Joseph Campbell. But something to the effect of, we're not searching for the meaning of life but for the feeling of being alive. And I think that's correct. And I think a great... If you play red light, green light with principle, as you search for your principle, I think you could do a lot worse than knowing you're on the right path if the thing makes you feel more alive. Like, if you go in the direction… and people know what it's like to feel alive. They can call to mind these moments in their lives where they felt the most present and alive. And using those as a signpost to what your principle might be or what you should be doing, I think, is a really great thing. And that's certainly how I remember reading that line 15 years ago as well, and then starting to chase the feeling of being alive. Not a goal, but just that feeling. And everyone can answer this question, by the way. It's a really great way to have a conversation with someone, to kind of ask them where they feel this and then also why they're not doing more of whatever the answer happens to be. Which is a funny circumstance of humans, that they kind of know what makes them feel most alive and then they don't do it most of their lives. [00:00:00] S1: That's a very interesting question. What's your guess on why they don't?
· David Senra, Patrick O'Shaughnessy
[00:00:00] S1: That's a very interesting question. What's your guess on why they don't? [00:00:00] S0: Usually it's simple, which is fear. It's fear that by pursuing an original path... I have this idea that the best story always wins, and I actually spent the last couple of months really trying to figure out what do I think "best story" means. And the best principles for a great story that I could come up with were originality, hardship, and transformation. And if you dig into originality, that one is really interesting to me because people don't pursue original paths usually because they're fearful of the unknown. Because an original path, by definition, means it's all going to be on you. And that's uncomfortable and hard. And because an original path usually means leaving a very comfortable current existence in a way that's scary. And so I think when you really drill people on why not, they'll give reasons that add up to, "I'm afraid," and that's hard to get over. [00:00:00] S1: You've said to me before that you used to be a masochist for introspection. First of all, when did that stop? And then do you think that helped you find this organizing principle for your life?
· David Senra, Patrick O'Shaughnessy
[00:00:00] S1: You've said to me before that you used to be a masochist for introspection. First of all, when did that stop? And then do you think that helped you find this organizing principle for your life? [00:00:00] S0: It definitely helped me find it because I wanted to not waste life. When I was a little kid, young, five years old or whatever, I had this just crippling fear of death. Like, I remember my mom and dad would have to sit and hold my hand for me to fall asleep at night because... And the reason was I would just sit there spiraling on this crazy idea – maybe this is why I studied philosophy – that someday I would not exist, and that just freaked me out and did for decades. So that probably kicked off this introspective period of my life where I was very curious about philosophical traditions and religious traditions and metaphysics and all this kind of stuff because I wanted to know, what the hell is the point of all this? Like, what's the point? What's the meaning? What's the purpose? And otherwise, it's just terrifying, right? That we're here for a blip and then gone. [00:00:00] S1: Yeah.