Invest Like the Best with Patrick O'Shaughnessy
00:55:21 · S3, Sarah Guo
[00:55:21] S3: For everywhere else. [00:55:22] S2: Everywhere else. And we see it in our companies where I'm thinking about in one of our portfolio companies, the marketing department is like a person in the house. This is a company that serves lots of customers. They need to do very traditional things, sales enablement content. What happened was the guy in charge of marketing is interested in creating leverage for himself. And he's like, I made an autonomous marketing department for us, the company. In every function as you learn faster, do less of the mundane, you will repurpose that time somehow. Do you work less now that you are more productive with AI? Yeah. I work more. And I think this is like a core wisdom of Jensen's, which is we're all gonna be more employed. And we need to make sure that people are given access and education to the tooling that will allow that to happen. [00:56:21] S3: What you've built is incredible. We've loved through the Colossus side getting to know your whole world. It's so distinctive. You are a great example that there's always room for great. Meaning, there's plenty of early stage investment firms when you started conviction. And yet here we are four years later or whatever and if you ask the people you've worked with, you've made a real huge difference in their lives. There's just always room for great. I think that's like a great awesome lesson, especially because I love how you described the early pitch was not like here's how we're differentiated every level of the funnel. We're just gonna run at this thing.
00:56:21 · S3, Sarah Guo
[00:56:21] S3: What you've built is incredible. We've loved through the Colossus side getting to know your whole world. It's so distinctive. You are a great example that there's always room for great. Meaning, there's plenty of early stage investment firms when you started conviction. And yet here we are four years later or whatever and if you ask the people you've worked with, you've made a real huge difference in their lives. There's just always room for great. I think that's like a great awesome lesson, especially because I love how you described the early pitch was not like here's how we're differentiated every level of the funnel. We're just gonna run at this thing. [00:56:52] S2: By the end, I got so frustrated that I was just like it's an execution game. [00:56:55] S3: Totally. I ask everyone the same traditional closing question. What is the kindest thing that anyone's ever done for you?
00:57:00 · Sarah Guo
[00:57:00] S2: I love this question. I'm gonna give like a collective answer. I think there are so many people who are extraordinarily accomplished in Silicon Valley who care very little for pedigree as soon as they have conversation with you. And they're like, maybe you can help me or you have an interesting idea or maybe I just think you're promising. And the dominant factor in their own willingness to invest in a relationship or a person is just their assessment of the idea in the person. I think that's amazing. That is not how most ecosystems work. And so Ashim Chaudhna and Anil Busseri and Joseph Fansonelli and Reid Hoffman who hired me at Greylock, I started when I was 23. People love to make fun of young VCs where they're like, what a barnacle on the ecosystem. It's a terrible experience for entrepreneurs. They don't know anything. They're trying to advise people. Who gave this kid money? And I'm like, well, one, my job is just to make other people successful at the time. You can take any task in any job and just try to be great at a task with mimicry and first principles thinking. We hire earlier career people at my firm, but I do think, oh my goodness, thank you for taking a shot on some random person and then investing the time to like teach me how to be an investor. I think there were a few people who gave me advice starting the firm who I think they would think of this as entirely trivial. I'm just giving you my opinion. But Ravi Gupta who is now co CEO of a new thing called Ithaca, Dylan Field and Elena Nadelinski, John Lilly who's been a longtime partner and friend. There are a few folks who were just like, you can definitely do it. I was gonna do it either way. But having the encouragement of people who believed that there was room to be great and including some of our first LPs, I will be forever grateful to, I guess, the people who took risk with me.
00:58:56 · S3, Sarah Guo
[00:58:56] S3: It's beautiful the world runs on faith, belief without evidence yet, and still conviction in someone's ability to do something. Pretty cool. [00:59:03] S2: It's faith in people. And we talked a lot about how people's ideas and our opinions of them are intertwined. But I think that's a beautiful thing because you don't need any particular advantage to have an idea. The fact that folks will evaluate that and put faith in us, I could not be more grateful. [00:59:22] S3: I've learned a lot watching you operate and talking to you. This has been really fun. Thanks for having me. [00:59:28] S2: Thanks.
00:59:30 · Patrick O'Shaughnessy
[00:59:30] 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/subscribe. 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.