Invest Like the Best with Patrick O'Shaughnessy
· 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.
· Patrick O'Shaughnessy
[00:00:00] S0: It’s a really cool thought exercise to say, okay, play out the thing I’m doing to its natural extreme. Do I want that state? Probably no one does that.
· Kareem Amin
[00:00:00] S1: One time, when I was much younger, I was like, oh, I want to make a lot of money and then I’ll be a philanthropist. And I’m like, is that actually useful? There are a lot of philanthropists. Is it working? Are they actually impacting the world? Could we move faster with some other kind of formula or setup? Or is it just that I want the control to pick the causes that I want? Maybe one more thing on the death thing that I think is kind of interesting was my own insight that I had. I went on this 10-day silent retreat a while back. I thought I was going to just go think. It was not that. It was kind of a spiritual experience. It was called Hridaya — not like a Vipassana. Their approach there is a non-dual approach to meditation. Typically you meditate on your breath or some object, whereas in non-dual traditions it’s called the direct path. And in the direct path, you meditate on the space between the breaths, or you ask the question, who am I? A very frustrating question. I would not recommend it. But anyway, I’m doing this thing. On the fifth day, I have this big insight where I’m like, I figured it out. I got it. Then on the seventh day, I’m like, okay, what now? I start imagining going back and telling my friends about this insight, but I’m like, oh, I’m not here. I’m just imagining the future. I kept wanting to go towards the end. And then I had this big flash of insight that I try to remember, but it said, whenever you’re picturing the future or anticipating the future, it’s kind of like Freud’s death drive. The only thing that happens in the future is you die — the far future, whatever it is. And so you’re accelerating that. And as soon as I had that thought, it’s kind of the death drive. Thinking about the future is the death drive. And so I immediately felt back in my own body, in the moment, and felt the boredom of where I was. And I was like, wow, this is such delicious boredom. I finally got that insight, which is, I’m so grateful to be bored right now because it’s so amazing. I also realized that I have this scarcity — food scarcity. I was thinking constantly about food and, where am I going to eat? And then I just had this one pea and it exploded in my head. I was like, this is too much. I can’t. But I realized that I have an accumulation tendency where I’m like, where’s the food going to come from?
· Kareem Amin, Patrick O'Shaughnessy
And in the company, I noticed I’m like, where’s the next one going to come from? Now I’m aware of that, and I’m aware of when I have enough, and then I can take more risk. I don’t need to accumulate something way beyond what we actually need. [00:00:00] S0: What was the day five insight, or was that the insight itself? [00:00:00] S1: It’s hard to describe because it’s an experiential thing. I think it was a momentary experience of understanding what matters, because I felt like, oh, I’m connected to all things — really bizarrely — just feeling like, hey, I’m a component, or part of this whole thing, and I’m connected to all things and they all matter. I had this thought of, one, I’m no better and no worse than anyone else, but also it made me feel this real empathy when I see someone who’s suffering. I’m just like, oh, they’re also me. Not that I empathize with them as if I were them. I’m like, this is actually me. That’s kind of a really out-there thought, or belief. [00:00:00] S0: The strange thing is, it’s actually not at all — it’s like the longest-lasting set of beliefs in the deepest, richest philosophical traditions. [00:00:00] S1: Yeah. Today it’s still niche. [00:00:00] S0: It’s this abstract idea today, but quite an old one.