Invest Like the Best with Patrick O'Shaughnessy
· Patrick O'Shaughnessy, Kareem Amin
[00:00:00] S0: And feeling like shit. [00:00:00] S1: Yeah. I actually felt like I related, and we’re obviously in a much smaller spot, but even early on when we raised our Series A, I remember having that sensation of, if you’re doing this to get adulation or to get prestige or to make some money, there’s no end to that. It’s kind of like an empty thing that passes. The only judge of anything is yourself and your own self-respect. You have to be doing it so that you feel like what you’ve done is interesting and worthwhile. When you’re an ambitious person, your judgment is actually way higher than anyone else, because you know everything that you’re thinking and you know everything that you’ve done. So I know everything that I’m thinking about or doing, and my standards are higher than anyone else. [00:00:00] S0: There’s this thing I like to do where, when I spend some time with somebody, I wait an hour, and then I write down notes in my phone. I benefit from the hour. It’s like a cleansing function — whatever lasts in my brain through that hour. When we were last together, the one thing I wrote down was this notion of optimizing for self-respect over everything else, as the North Star for behaving. I’m curious how that relates back to risk and courage. Do you think those things are related? Do you think it’s possible to help people become more courageous and take more risk?
· Kareem Amin
[00:00:00] S1: For sure. In order to do that, you just need to understand your mind and your motivations more, and be more honest about them. So again, back to the saying — simple things, honestly. It’s very hard to admit to yourself why you’re doing something. Even if you look at the narratives for companies, none of them have any relation to the motivation of the founders, and we don’t talk about that in public. For me for example, it’s like, why am I building a company? Do I think that I will be more liked or loved if I do something that is a success at a world-class level? Can I get that now? I’ve had friends come up to me that are like, hey, I don’t care if you succeed or fail, I love you. And I was like, wow, that’s actually helpful. I didn’t think it would be, but it’s feeding — some part of my desire must be fueled by that, but I can get that right now. And now I can start to take real risks where I’m thinking about the business and not trying to fill this particular need. VCs have this common trope that is, hey, we invest in someone that has a chip on their shoulder, or has some kind of lack that they’re trying to fulfill. And this is common across creative work. The trope is, you’re depressed or you’re anxious or whatever, and you’re trying to fill that, and you’re actually afraid to lose that depression or anxiety or whatever it is, because you feel like you’ll be less productive or creative. Through my journey, I had this moment where I was like, you know what, I’m not going to create from a place of lack anymore. And I went around probably pretty annoyingly telling people, I have everything I need. I’m good.
· Patrick O'Shaughnessy, Kareem Amin
[00:00:00] S0: Post-lack. [00:00:00] S1: Post-lack, yeah. It’s a great negotiation leverage, because there’s nothing you can give me. I feel great. I’m already complete. From there, you can still create. I think people are tremendously misunderstanding this, in my opinion. If we were in a post-scarcity world, no one will do anything. Everybody will just be hanging out. And I was like, have you been to Burning Man? People are still doing stuff and they have things. You can create from a place of wholeness. And in fact, you will be less destructive in the world. I think you’ll create less damage. We keep thinking here, hey, let’s think of our customers. What are we trying to give them? Why do people keep saying customers first? It’s because when you’re in a company, things start to happen where it’s like, this person’s thinking about their career, or this person wants to please this other person. They’re not thinking about the customer, they’re just thinking about the internal dynamics. The more whole you can be, I think the more risks you can take and the more courage you will have, because you have nothing to lose.
· Patrick O'Shaughnessy
[00:00:00] S0: It’s funny to me that perhaps the most interesting duo in modern business history, Jony Ive and Steve Jobs, were almost undoubtedly creating from this generative place. I don’t know if they used the same terminology or something, but you read it all — it’s all there. They’re the most adored, but maybe the least emulated. It demands the question — the things that got you to this sense of wholeness from this place of lack. There’s been much strange debate about the role of introspection in business and in general. Naively, I would say it’s introspection. It’s a key tool in the toolkit to get from one to the other. Curious what your experience has been, or what you would offer about that.
· Kareem Amin, Patrick O'Shaughnessy
[00:00:00] S1: I kind of understand the motivation here, because one thing I talk a lot about here, and have thought about for myself, is that the balance between doing and meta-analysis can sometimes flip. So you should be doing 90% of the time and then meta-analyzing 10% of the time. At work, we’ve had this happen a lot, and I talk to the team a lot about it, where people are like — hey, what is going to happen in one year? Why are we building this feature instead of that feature? And I’m like, is that stopping you from taking the next step in your job? If not, then you’re procrastinating. My sense is, in his conversation around that, I think his example was Walmart. If you’re trying to build more Walmarts, yes, you should always be thinking, wake up in the morning, build more Walmarts. But at some scale, when Walmart is affecting all of us, if you don’t think about why you’re building Walmart, or what more Walmarts do to us or to a shared environment, that responsibility is on you. The more you make and the more successful you become, it is part of your responsibility back to all of us to think about what you’re doing, that you’re our representative now. You’re not a completely independent actor. And in fact, we have the power to pull some of that stuff back from you. [00:00:00] S0: So is there anything you did in particular, going from lack to wholeness?
· Kareem Amin
[00:00:00] S1: For me, the introspection was a journey to understand — why ambition? So I was suspicious of my own ambition. I was like, what am I trying to get out of this? Part of why the company took some time to take off was because I was grappling with that. And that led me to investigate which parts of me are trying to be expressed through this. And that was just my own personal interest. I just found that I couldn’t just do something without understanding my motivation for it, because I was looking at people who are further ahead in my field. If you’re a great business person, or you built a great company, I was like, do I want that? I think it’s also coming from valuing my time and myself. I was having this experience where I’m like, what if I took myself really seriously? You could take yourself lightly and just be like, well, these are just thoughts. I want to do something big. So do other people. Or take it really seriously and ask: why do I want to do that? What would I actually offer the world if I was able to do that? And then thinking, hey, you can succeed and create a lot of damage in the world. I think a lot about death. On your deathbed, what are you thinking? How does it feel in that moment? If you had a moment to reflect, how do you judge yourself? And there’s the experience of every day, living a life that you feel is worthwhile on a day-to-day basis. And there’s also, how did you impact the world, if you did impact it? I wanted to make sure that I felt like I really grappled with that correctly. And I didn’t just try to accumulate resources and just be like — hey, I did something big, I accumulated some resources. It does go back to this justice principle. It’s like — if you’re going to do something big, you need to think about the consequences of you taking that role, because it’s just a role.