Invest Like the Best with Patrick O'Shaughnessy
00:43:00 · Gabe Stengel
[00:43:00] S1: I worked during COVID so I didn't even get to see what an office looked like. John, my co founder and I used to joke that it's a very expensive business school education. So you're just doing everything wrong. Didn't know how to hire, didn't know how to fire, didn't know how to mentor, didn't know how to manage, didn't know how to give feedback, didn't know how to set direction. And a lot of the people problems that arise with scaling quickly feel like eating glass to me anyway. And so when people quit, when you have retention issues, when you spend six months recruiting Canon, they don't join, that's chewing glass. When you spend a bunch of time working on a product that gets completely washed over by the next model that comes out and makes you feel like an idiot for spending all that time and capacity on something that was the wrong call, chewing glass. When you get rejected by 40 investors in a row before you're able to raise capital, chewing glass. And my experience of startup building is it's like a roller coaster where you have to feel the extreme highs and feel the extreme lows and I'm a super emotional guy. And I try not to let the team feel it but I will feel on top of the world at the high and like everything is cataclysmic at the low. But then if I look back at the journey, the lows get lower, the highs get much higher. And I look back three months ago at the low I was dealing with or the high I was dealing with, I was like I could do that in my sleep now. And I think it's just about modulating those things and channeling the emotion to push the business forward but not letting it distract you.
00:44:27 · Patrick O'Shaughnessy, Gabe Stengel
[00:44:27] S3: What about aggression? [00:44:28] S1: Like that seems kind of like a trope. You've interviewed Pat Grady. Pat Grady was at our board meeting on Wednesday and we presented what was it extremely aggressive plan for next year in terms of hiring goals, commercial goals, product goals. And one of the reasons I love Pat is because he boils everything down into like two bullet points and it's logically infallible. And, you know, he's just like premise one, premise two, this is the result. And he goes, Gabe, well, if everyone in finance is gonna make a buying decision on AI in the next eighteen months. And they are definitely gonna buy something no matter what even if you're not there. Then the only thing that matters is that you can blitz the market as quickly as possible to make sure that you are there. Given that, do you think this plan is aggressive enough or no? The answer was no. And the reason it wasn't aggressive enough is because I was being soft. And I think the reality is you need to be so so so aggressive and underwrite all that risk and know the game that you're playing. And my goal is if that enter back business is to increase the tails of the distribution. It's fine if it gets 30% more likelihood that I fail if the odds that I become a $100,000,000,000 company also increase by 20%. But you actually have to be okay with raising both of those tails at the same time.
00:45:39 · S0, Patrick O'Shaughnessy
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00:46:39 · Gabe Stengel
[00:46:39] S1: When we were raising our series a, we didn't have any star investors in our cap table yet. But there was a great investor, David Tisch at Box Group who was an early pre seed seed investor who introduced me to a bunch of all time greats for the series. And I thought, wow. I've seen what it does to get a blue chip investor in your cap table, what it does for recruiting talent, becoming more of a black hole for brand and customers and so on. This is finally the opportunity we're gonna have to do that. We've been building for two and a half years. And David introduced us to 40 investors and I met with everybody. I met with Sequoia, Kleiner, Benchmark, everybody. And 40 people passed. And it wasn't just like you got the email with the deck and it's not exciting. It was like, oh, is interesting. Let me meet Gabe. Oh, I kinda like Gabe. Let me spend an hour with him. Oh, Gabe, come to IC. Oh, Gabe, let's go to dinner. Oh, Gabe, come in for the weekend afterwards. You know what? We're gonna pass. And it's so personal because at that stage, has nothing to do with anything but you. Right? It's like somewhat... It's like being broken up with by 40 girlfriends who like every time you fell in love and then every time they said, not for you. And that was actually Thrive too at the series a. Thrive spent so much time with me. We went to dinner with Avery and Vince, fell in love with them and the firm because they were awesome and then crushing blow. And luckily Keith for boy came basically a month after everyone else had rejected us and Keith was like, Gabe, this isn't a contrarian bet. It's basically just Harvey for finance. Why would I do it? And I said Keith, if it's not contrarian, why did every single one of your friends just say say it was a bad idea and not believe in me?
00:48:13 · Patrick O'Shaughnessy, Gabe Stengel
[00:48:13] S3: Why do you think they didn't believe? [00:48:15] S1: For a lot of reasons. I think people underappreciated the TAM in finance which was silly but it's partly because I think SF has less intuition for finance because they didn't fund ION Group or Bloomberg or SMP or FactSet or PitchBook Morningstar and so on. And so there actually haven't been great venture backed businesses in this market and so there's no intuition for the kind of contours of the market and how large it is. Two is the product was terrible. And so every investor said, oh, I work in finance. Let me use it. Is it gonna transform what I do? And they tried it and it was wrong half the time. They go, this is never gonna work. And it's like guys, you know we're on the exponential. It's gonna work in six months or twelve months or eighteen months or whatever it is. I'm going to figure it out. And the final reason was people didn't think I could figure it out. People didn't have enough data points of watching me issue glass and watching me figure out what the next iteration would be. [00:49:08] S3: What do you think changed after that? Because now it's a who's who of CapDibble.
00:49:08 · Patrick O'Shaughnessy, Gabe Stengel
[00:49:08] S3: What do you think changed after that? Because now it's a who's who of CapDibble. [00:49:12] S1: Well, because I met all these guys very early on and I met them at every single round. And so every time I said, hey, we're gonna do this. And they said, yeah, there's no way. And then every time we would do it. And by the way, a lot of the times it would manifest in a different way, You would actually lose the key employee you needed or that actually excellent customer that you thought you were in land totally dissipated. But we kept figuring out what to do and kept navigating the market. And I think when you're investing in a market like today, especially at Applied AI where it's so turbulent, so ambiguous, you need to underwrite the founders being able to be extremely dynamic. [00:49:48] S3: Why do you think there aren't more credible financial services competitors?