Invest Like the Best with Patrick O'Shaughnessy
01:00:22 · Patrick O'Shaughnessy, Gabe Stengel
[01:00:22] S3: Why are you scared and insecure? [01:00:24] S1: I'm so paranoid about everything that can go wrong. Every day it feels like you're on the knife's edge of a thousand things collapsing. And I think the reality of this sort of business building is that it's a game of compounding momentum. How do you do every small thing to just race a little bit faster downhill and I'm just scared the momentum will stop. Or you hit a roadblock and then you go off course, and then you need to recatalyze momentum. And it's so clear to me how hard it is to actually build a machine that gathers momentum. So if there's any stumbling block that holds that velocity, if I wasn't constantly petrified of those moments, I wouldn't be doing everything under the sun to prepare for them. [01:01:01] S3: What have we missed? Like, what that you've learned about building a company like this in this era where everything feels like a jump ball? Like, it feels like there's gonna be a Rogo or a Harvey or whatever for every place that there can be, especially where the last mile wiring is hard and it's not just gonna be Anthropic, it's one company to rule them all or OpenAI. What else have we missed that you think is really important to the experience so far of building the business?
01:01:01 · Patrick O'Shaughnessy, Gabe Stengel
[01:01:01] S3: What have we missed? Like, what that you've learned about building a company like this in this era where everything feels like a jump ball? Like, it feels like there's gonna be a Rogo or a Harvey or whatever for every place that there can be, especially where the last mile wiring is hard and it's not just gonna be Anthropic, it's one company to rule them all or OpenAI. What else have we missed that you think is really important to the experience so far of building the business? [01:01:27] S1: I think that there are going to be businesses that solve all these problems. But the businesses that do it are gonna become black holes for talent and capital and brand and they're gonna be able to siphon in the resources to actually execute. Because AI is an amazing tailwind, but the execution bar is higher than it's ever been too to compete. And everyone is getting pulled into the big leagues and is having their welcome to the NFL moment. You have to move faster and be stronger and be more resilient and agile than you ever expected. And having the right team is more important than ever. And the right team these days is extremely extremely expensive. And so if you can't figure out what is the strategy to become a black hole for talent and capital as quickly as possible, I do think you are far more at risk at being roadkill of a lab or a company that can. [01:02:13] S3: When I do these, always ask my favorite question last. What is the kindest thing that anyone's ever done for you?
01:02:13 · Patrick O'Shaughnessy, Gabe Stengel
[01:02:13] S3: When I do these, always ask my favorite question last. What is the kindest thing that anyone's ever done for you? [01:02:19] S1: I benefited so much by having parents who were enormously kind and generous and selfless, but it showed up in such different ways for my mother versus my father. And my mother's version of kindness was no matter what I did, I was amazing and smart and could do no wrong even though growing up that was absolutely not the case. But she instilled in me the confidence to believe in myself even when you were in those low trajectories where it felt like everything was gonna go sideways 40 in a row. Anything right. 40 noes in a row, idiot failing out, flunking out, whatever it is. No matter what, she acted like I was maybe the smartest person on earth. That was irrational but you need some of that irrational confidence that comes from just undying love. My dad was very different. My dad, if I came home and I had done something wrong, was seething, could barely look at me, couldn't understand it. Right? Like he was someone who was so disciplined, so good, had such high standards. And so his version of kindness was figuring out how does he understand who I am and why I am failing at this thing and then help me. He would sit down and go over every detail with me even though he sometimes just couldn't even understand why I had the opportunities I had and I couldn't take advantage of them and take the time to make me better while staying true to his principles and his standards of excellence and his definitions of good too.
01:02:19 · Gabe Stengel, Patrick O'Shaughnessy
[01:02:19] S1: I benefited so much by having parents who were enormously kind and generous and selfless, but it showed up in such different ways for my mother versus my father. And my mother's version of kindness was no matter what I did, I was amazing and smart and could do no wrong even though growing up that was absolutely not the case. But she instilled in me the confidence to believe in myself even when you were in those low trajectories where it felt like everything was gonna go sideways 40 in a row. Anything right. 40 noes in a row, idiot failing out, flunking out, whatever it is. No matter what, she acted like I was maybe the smartest person on earth. That was irrational but you need some of that irrational confidence that comes from just undying love. My dad was very different. My dad, if I came home and I had done something wrong, was seething, could barely look at me, couldn't understand it. Right? Like he was someone who was so disciplined, so good, had such high standards. And so his version of kindness was figuring out how does he understand who I am and why I am failing at this thing and then help me. He would sit down and go over every detail with me even though he sometimes just couldn't even understand why I had the opportunities I had and I couldn't take advantage of them and take the time to make me better while staying true to his principles and his standards of excellence and his definitions of good too. [01:03:34] S3: You're building a fascinating business. It's been so cool to watch it get better. Thanks for doing this with me.
01:03:34 · Patrick O'Shaughnessy, Gabe Stengel
[01:03:34] S3: You're building a fascinating business. It's been so cool to watch it get better. Thanks for doing this with me. [01:03:40] S1: Thank you.
01:03:41 · S0
[01:03:41] 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. 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 PositiveSum. 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. You know how small advantages compound over time? That's true in investing, and just as true in how you run your company. Your spending system is your capital allocation strategy. Ramp makes it smarter by default. Better data, better decisions, better economics over time. See how at ramp.com/invest. As your business grows, Vanta scales with you, automating compliance and giving you a single source of truth for security and risk. Learn more at vanta.com/invest. The best AI and software companies from open AI to cursor to perplexity use WorkOS to become enterprise ready overnight, not in months. Visit workos.com to skip the unglamorous infrastructure work and focus on your product. Ridgeline is redefining asset management technology as a true partner, not just a software vendor. They've helped firms 5x in scale, enabling faster growth, smarter operations, and a competitive edge. Visit ridgelineapps.com to see what they can unlock for your firm. Every investment firm is unique and generic AI doesn't understand your process. Rogo does. It's an AI platform built specifically for Wall Street, connected to your data, understanding your process, and producing real outputs. Check them out at rogo.ai/invest.