Invest Like the Best with Patrick O'Shaughnessy
01:01:49 · Martin Casado
[01:01:49] S1: Yeah, a lot. Mean, I think most investors go through this, especially when you come from the operating world, you have to learn how to listen as an investor. And then you also have to learn how to ask the questions that you really care about so that you can answer the questions to yourself. It's a very delicate balance. I do feel like a lot of meetings with founders tend to be pretty performative on both sides. Like you don't know what to ask and so you'll be like, who's your competition? And then a lot of it is just asking questions for asking questions' sake but like it doesn't actually inform your decision. And then especially if you're an operator, you'll hear something you disagree with and you kind of want to fix that problem but that's kind of not your job. I have learned, and I'm not perfect, but the primary job is just to listen. A founder will tell you what they believe. If you disagree, you disagree, but that's what they believe. So often they'll say something like, well, but I would do it better and therefore like it's a good investment. It's truly an art. You have to make a decision based on that meeting. There's a lot of silly questions you could ask that are not really gonna inform that decision. What if Amazon does that? What does OpenAI? Like, whatever. You can answer that yourself. Maybe you can figure out how they think. But there are key questions that you really wanna know and kind of knowing which ones those are during the time of the meeting and getting those in is a hard thing to do. And I think I've really refined my ability to do that.
01:03:10 · Patrick O'Shaughnessy
[01:03:10] S0: Maybe a fun place to close is just to ask what has you most excited? We've talked about lots of the magic of this new era of technology and things that weren't possible before, bottlenecks that are now gone. I know all of that excites you but if you had to just step all the way back and describe why this job is so incredibly fun right now and why you're most excited.
01:03:32 · Martin Casado, Patrick O'Shaughnessy
[01:03:32] S1: I'm more and more of the belief that this is an industrial revolution level shift and for me the industrial revolution went from basically a zero sum world to like a non zero sum where value is being created, net new value is being created and I think this is a very similar shift where before to solve problems, you had to solve very complex engineering problems which basically didn't scale and were very tough and then you'd have to maintain them and that's why all software has always sucked to basically being a capital problem. I don't know about the real world yet. I think we'll get there but I think we've turned this into a capital resourcing problem and we're capital allocators. And so I just feel like we're just in this very, very strategic position to help drive the future in a much, much more direct way than we ever have been before because I think this is a scale up capital game that causes that to happen. I don't believe private markets have limited TAM. I think they have unlimited TAM and the more money that goes into them, the more value that would be created. So I just feel like we're in this very privileged position, very key to the innovation chain, and we're both very lucky to be here. [01:04:34] S0: I love the every two year schedule that we're on. I hope we get to do it again in another two years. I can only imagine what the world's gonna look like two years from now. [01:04:41] S1: We'll have our Grokbots talk. [01:04:42] S0: Thank you so much for your time. [01:04:44] S1: Thank you.
01:04:44 · Martin Casado, Patrick O'Shaughnessy, S2
[01:04:44] S1: Thank you. [01:04:45] S0: If you enjoyed this episode, visit colossus.com. You'll find every episode of this podcast complete with hand edited transcripts. You can also subscribe to Colossus, our quarterly print, digital, and private audio publication featuring in-depth profiles of the founders, investors, and companies that we admire most. Learn more at colossus.com slash subscribe. [01:05:06] S2: Patrick O'Shaughnessy is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of PositiveSum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc.
01:05:49 · Patrick O'Shaughnessy
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