Invest Like the Best with Patrick O'Shaughnessy
00:36:31 · Patrick O'Shaughnessy, Christina Cacioppo
[00:36:31] S0: So as I visualize that, what that feels like to me is a constant penetration test. Yes. Where an agent is trying to break in like a white hack hacker agent all And the then every time they find something, it's got a buddy agent that's a patch of... [00:36:44] S1: Let's fix it. Yeah. [00:36:45] S0: Is that like the ultimate product vision then? [00:36:48] S1: For some parts of Vanta, yes. I think we can do that in very compelling ways for the bulk of our customers. I think CrowdStrike will do it better for an enterprise. This is where choosing where you play and what market segment is most important there. [00:37:03] S0: Is there a firm that's doing something now that you start to encroach on? Like of the traditional security... In [00:37:08] S1: different markets... Mean, a ongoing penetration tester and remediator fixer. We think we can do that for the cloud providers, like in AWS and Azure, like misconfigurations there. Classically, Wizz does that. Wizz will do it for its customers. Wizz's customer base starts at a multi thousand person company. And their price point count starts at a multi thousand person company. We're more thinking about the platform as where are we already embedded with customers? Where are they unlikely to go pay $150,000 for a whiz, but very well could pay 40 or 50 for something suited to them. Thinking through where are we already strong and where are the competitors focused elsewhere, but probably on a more upmarket segment. How has your
00:37:08 · Christina Cacioppo, Patrick O'Shaughnessy
[00:37:08] S1: different markets... Mean, a ongoing penetration tester and remediator fixer. We think we can do that for the cloud providers, like in AWS and Azure, like misconfigurations there. Classically, Wizz does that. Wizz will do it for its customers. Wizz's customer base starts at a multi thousand person company. And their price point count starts at a multi thousand person company. We're more thinking about the platform as where are we already embedded with customers? Where are they unlikely to go pay $150,000 for a whiz, but very well could pay 40 or 50 for something suited to them. Thinking through where are we already strong and where are the competitors focused elsewhere, but probably on a more upmarket segment. How has your [00:37:51] S0: personal motivation changed? You set out to build this thing. I remember talking to the first time about this very charming way you built the original product, Billy and Excel first, and this sort of seems very old school. Looking back on it, there's always like the dog that caught the car thing where like [00:38:05] S1: Yep. [00:38:06] S0: Alright, built like this huge software business. Amazing. How has your own motivation evolved or changed through all this? Why keep going?
00:38:06 · Patrick O'Shaughnessy, Christina Cacioppo
[00:38:06] S0: Alright, built like this huge software business. Amazing. How has your own motivation evolved or changed through all this? Why keep going? [00:38:13] S1: It's interesting and challenging and it changes all the time. I really like my job. Sometimes I feel like I'm good at it. Often I feel like I'm bad at it. That's fine. That's in some ways not the point. But it changes and it's different. And when I feel like I've gotten good at it, usually something happens. It just changes and then I feel bad at it again. And I really like that dynamic. In the beginning, I had a lot more of a feeling of People think I can't do this. I think I can and I'm going to show them. And I still have that. Even to the like, you don't think Vanda's gonna be 250,000,000,000? Like, let me show you. I still have it, but think you probably tell there's like less of a dark edge to it. Still a little dark edge, but like there's less of it. It's oh cool. We got here. Now we're just going to see how far we can run-in a way that feels a little bit more like fun and joyful. So my day to day is not always joyful. I don't mean that, but it feels more, oh cool. Let's see how far we can go with this. And I think we can go pretty damn far. Whereas I think in the beginning, it was more like, you don't think I can get off starting line. Let me show you.
00:39:17 · Patrick O'Shaughnessy
[00:39:17] S0: Your finance team isn't losing money on big mistakes. It's leaking through a thousand tiny decisions nobody's watching. Ramp puts guardrails on spending before it happens. Real time limits, automatic rules, zero firefighting. Try it 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. Ridgeline offers one unified platform that automates away the complexity across portfolio accounting, reconciliation, reporting, trading, compliance, and more, all at scale. Schedule a demo at ridgeline.ai. Every investment firm is unique, and generic AI chatbots don't understand your process. Rogo is built by finance professionals. It's connected to your data, learns your process, and quickly produces client ready outputs. Check them out at rogo.com/invest. The best AI and software companies from OpenAI 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. How surprised would the eight year old version of you be at some specific skill that you've developed in the way you've Probably surprised. Yeah. It's like the most surprising one that you're now good at that you... Oh, or old you would have said no way?
00:40:39 · Christina Cacioppo, Patrick O'Shaughnessy
[00:40:39] S1: I like go to market more than I ever would have guessed. You get to talk to like personable, friendly people all the time. And I was like a terrible public speaker. I would get the most nervous in front of my own team because I cared the most about what they thought about. And I was like, my god, I'm representing you. I want to do this so well. Exposure therapy was helpful on that one. You're too... You're like, you just do it and you do get better at it. But I think the like thought of being at kickoff or an all company get together in front of a thousand people on a stage. And I think I'd have been like, shit, like, I'm going be bad at that. I think the people around me would have been like, yeah, she'll be bad at that. How much coaching can she get? It's like anything else. It's like, yeah, if you work hard at developing a skill, you tend to get better at it. You just to put in the work. [00:41:24] S0: That one particular- in particular, I'm very interested in that one. It just seems always high leverage. What matters? You've given however many hundreds of these things. What makes one good?
00:41:24 · Patrick O'Shaughnessy, Christina Cacioppo
[00:41:24] S0: That one particular- in particular, I'm very interested in that one. It just seems always high leverage. What matters? You've given however many hundreds of these things. What makes one good? [00:41:33] S1: The trope of like no one remembers what you say, they remember how you felt. It's so annoying, but it is so true. I do have to believe in the content. And if I just get up, I feel like it is content less. I will also feel that way and it will be obvious to everyone. You kind have to figure out your version of it, which for me, I try to put real content in and then also hold in my head, no one's gonna remember any of these that's not the... So much more. Yeah. [00:41:57] S0: And the key to good heart is what? [00:41:59] S1: Believing in it yourself. Authenticity. One on one on a stage. People are pretty good at reading one another. When you feel like the person you're talking to is like going through the motions or doesn't really feel like it or is misleading you, maybe also misleading themselves. People can tell. They can't entirely articulate what's happening. Something seems off versus someone who is authentically into it. Even if they're into something kooky, ad just comes off. [00:42:28] S0: What are the big trade offs that you struggle with right now? You can't do everything. You got to make decisions. The stakes are higher than ever. It's easier to build than ever. It seems like a cool time to be doing what you're doing, but there must be big trade offs that you struggle with. What are those