Invest Like the Best with Patrick O'Shaughnessy
01:03:47 · Jeremy Giffon
[01:03:47] S2: I certainly care about productivity. For me, by far the most generative thing is conversations, which I guess are downstream of relationships. Part of the reason my book reading has gone down is I'm friends with a lot of people that read a lot of books. If I can only keep one thing, it would be conversations with people that I find interesting. But I also think like I'm uniquely tolerant of distasteful and weird people. I get asked for a minute like what's your media diet and conversations are my answer and it always feels like the answer falls flat with people. And I think it's because they're not friends with like weirdos. A lot of my friends I think are sort of people would largely find strange at best, distasteful at worst. If I can't predict what the person's gonna say after knowing them for a while, I like them a lot and that's a very high variance thing. Old books are good. I think YouTube remains underrated. There's a lot of really obscure things on YouTube that I really enjoy listening to. YouTube sort of remains the library of Alexandria of our time maybe of ever. But yeah, YouTube doesn't feel generative. I think the only thing that's generative is conversations so far in early twenty twenty six. I would say chatbots can lull you into feeling generative, but if I actually look at like the actions that I've taken, you can feel really productive after like a good two hour session on a chatbot, but I actually don't think they're that generative.
01:05:11 · Patrick O'Shaughnessy
[01:05:11] S0: If you think about great investing ideas, what is the right balance between simplicity and complexity? Both in the ones that you've done yourself but also studied.
01:05:22 · Jeremy Giffon
[01:05:22] S2: I really do think people value complexity for the sake of complexity a lot. I think a lot of investors are in the like feel clever, look smart game more than the money game. Personally I think this has been a big area of self development for me which is the clever thing is not always the thing that makes money obviously. You either have to say I am looking for investment ideas that are so complex that no one is gonna do them or it should actually be quite simple. I'm a bigger and bigger believer in the simplicity which is you probably want to be long Elon Musk. That level of idea, I actually think the gift is being able to sell that idea and maybe even dress up this. I think a lot of the investing media actually serves for the people who are really good to dress up those ideas in a way that makes them feel differentiated and smart enough to what is actually sort of long Elon or long Bitcoin. I think of a guy that I know who exclusively does bankruptcies. He makes a lot of money. That's very complex and very difficult, but it's a tremendous amount of work. It's grimy. It's difficult. There's a lot of risk and personal stuff and that to me is like an example of getting paid for complexity. Whereas a good example of simplicity is you should just buy big companies when they're at their two hundred week moving average. I love that idea because it's just so simple but it's right. One story that I absolutely love cutting through the mess and getting to like complete clarity on how to evaluate an investment is from Richard Rainwater which is there's these stories about him that you would basically come into his office with a yellow legal pad and you would write out your thesis on one page and then you would tell them what percentage of your net worth you're gonna put in the deal and based on your one page thesis and the percentage of net worth that was gonna put in he would say yes or no and I think that's genius. People don't do that because that's really hard. It makes things way harder. First of all, it's hard to write a compelling thesis in a page, much easier to do it in a 400 page slide deck. And second of all, no one wants to say well I'm only putting 3% of my net worth in this. To me that's one of the most simple, clear examples of really cutting to is this a good investment or not that I've ever heard.
01:07:36 · Patrick O'Shaughnessy
[01:07:36] S0: One of the I think natural points of leverage now is the ability to hire extraordinarily well, which means two things, attract an amazing differentiated talent pool and then select from that group effectively. That's something that you thought a ton about in building your business and it seems like a skill that if you got good at it would be unbelievably valuable in this era specifically, where the returns to like outlier talent seem to be going up and up and up. What did you learn about the two stages of that process? I'm especially interested in attracting a unique pool of talent in the first place.
01:08:13 · Jeremy Giffon
[01:08:13] S2: Maybe the most practical thing is that I think is very low hanging fruit is just a job description. I think job descriptions are one of these things where they are written for nobody to be read by nobody and they're sort of this like token document. It's more about does the job description exist is more the question versus like what's written in the job description. I tried to write one that followed a very simple rule which was a) obviously I was gonna post it on Twitter and LinkedIn, anything you post has to be a good standalone post. It can't be something that you wouldn't share if you didn't know me. I think what's so important in any sales pitch which is what a job description should be is disqualifying who you don't want. And the nice thing about a divisive statement is that when it resonates it deeply resonates with the person and so I just try to think of okay like what are all the traits that I would want someone to have and try and make them again to go back to the like how you do one thing is how you do everything that would make them the type of person I was interested obviously the skills and the experience was gonna be table stakes. I tried to write out traits and ideas that would really be inspiring and for the right person to be like, woah, like this person really gets me, understands me and would make people mad. One of the things that I posted the funniest was or got the most reaction was you're an ideological minority at a top 10 school. And what I love about that is that it's entirely open for interpretation. I would get people who would be many different things, who'd be angry that I only want a top 10 school. The nice thing about top ten school is it's a fully ambiguous statement. What I love about it is a) there's some schools that I think uncontroversially are top 10 and so I get those people. You can also just sort of assert that your school is a top 10 and I had a few people from schools that I would not say were anywhere close just sort of assert that and I thought that was great. I had people select out because they were sort of like, oh, don't know if my school is, I'm not gonna apply, that's great because I don't want those people. And then ideological minority was really interesting.
01:10:16 · Jeremy Giffon, Patrick O'Shaughnessy
I had a certain idea in mind but people gave me all kinds of answers about ideological because you know I didn't necessarily political, there was all kind of answers around how that person stood out at their school and so those statements are great because they're like highly ambiguous. There's a bit of an inherent test of confidence. I would even get a few posts that were like, I think this is bullshit, should hire me, I didn't go to a top 10 school, you're an idiot and I love that person too. The more you can do statements like that where they like get this sort of reaction is great. Imagine what you would have to do in an interview to like get at all of those various traits. Statements like that I think are underutilized in these job descriptions. [01:10:57] S0: It's a cool idea of baking the interview into the job post itself. It seems to me like an underrated area of inquiry today that I know you're interested in is the cultural and intellectual traditions behind major movements. I think that that has certainly been true in this wave of technology. And it's not something I see talked about, written about very much. And I'd love you to just riff on your interpretation of the key sets of beliefs behind the people and the institutions that are ushering in the biggest wave of technology change that we've probably ever seen.