Investor Stories 481: Lessons Learned from Centana Growth, a16z, and Emergence: Trusting Management, Spotting Original Thinkers, and Investing Before Revenue (Byunn, Ulevitch, Saper)

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Nick Moran: Welcome to the podcast about venture capital, where investors and founders alike can learn how VCs make decisions and reach conv. Your host is Nick Moran, and this is the full ratchet.

Host: Welcome back to tfr. On today's special segment, we ask guests to tell the most important lesson that they've learned in their career. Here's the segment called lessons learned. On, uh, today's special segment, we have Eric Biun of Santana Growth. Eric, what is the biggest mistake or hardest lesson you've learned as an investor?

Jake Saper: What's the story behind it?

Nick Moran: Yeah, I came to investing business from opera, from a series of operating roles where I've been a manager in a company. That lesson that was very hard at the beginning and which I still have to remind myself from time to time, is management is management. They are spending quite a bit all of their mind share on the issues and problems of advancing their company. We, as investors, it can be easy to kind of sit back and be like, oh, I have a clear point of view of this. I've seen 50 companies in this space or in this category or in this situation, and you always have to do this. I just think that lesson is always, you got to work with, you got to trust management. They have a perspective, they have a view. There's a reason for that. I think most management teams are very good about trying to understand the perspectives of their investors. And, and I think investors as a whole, whether it's myself or others that I sit on boards with, we sometimes forget that we should do the same.

Host: On today's special segment, we have David Ulovich, GP of Andreessen Horowitz, American dynamism. David, what is the biggest mistake or hardest lesson you've learned as an investor?

David Ulevitch: There's probably two people that I interviewed on the team early on who I didn't hire, who have since gone on to become competitors. So I wish I had hired them.

Host: I guess that. What'd you miss in the hiring session cycle?

David Ulevitch: What did I miss? That is a. That is a good question that I actually am still trying to figure out the answer to. I think in the case of one of them, I failed to understand how high agency this person was and how much of an original thinker. He was. I think I didn't interview deeply enough to understand that he was not a herd thinker, but was really an original thinker at his own point of view. You know, I'm very lucky. I have a partner, Katherine Boyle, who, she started the American Dynamism practice with me. She is truly an original thinker and so I benefit from that on a daily basis and I think that's an important attribute in venture. And I think I underestimated, um, actually with both candidates just how original their thinking was and how they kind of came at things from a first principles view and how high agency they were to be able to articulate those things. I don't think I interviewed them deep enough or asked the right questions to really identify that which is now very apparent from observing them as investors.

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Host: On uh, today's special segment we have Jake Saper of emergence. Jake, what is the biggest mistake or hardest lesson you've learned as an investor? What's the story behind it?

Jake Saper: Well, I mentioned the figma passing. I think that when you overly rotate on monetization and you under rotate on leading indicators of value creation, that's where you mess up. There's a place you mess up. As an early stage investor, if I'm investing just based upon commercial success, then in some ways I've missed the boat because my job is to bet on the company before the commercialization is truly obvious to everybody. My job is to bet when I have a unique thesis, um, before the rest of the market. Mechanical Orchard is a good example. We invested in that company in 2023 and it was a services business. And people were like what? And I remember actually being apologetic as I was explaining it to people, including these. I remember showing up at a VC thing a few weeks after I did it and people were like what's the most recent investment you've done? And I was like well I did the services business. And people were like what? That's stupid. And I mean they didn't say it but you could see in their faces. But I think leading indicators there were interesting. And following this hunch that AI Native services is going to be a thing was the right so far. It was the right bet. Who knows obviously how that whole AI Native services thing will play out, but I'm betting a lot of my time and money on it.

Host: I love that lesson. I feel like if you're not doing investments that make people furrow their brow, maybe you're not pushing the boundaries enough.

Jake Saper: I'm literally going to my first board meeting today for, um, a company called Bedrock Robotics, which is aiming to be wayo for construction.

Nick Moran: Wow.

Jake Saper: And I think similarly, I kind of get, like, looks where it's like, what? How is I even like, does that make sense? Like, and, uh, like, I don't know if it will make sense or not, but hopefully people will be listening to this podcast in five years and be like, oh, yeah, Better Robotics. Way more for construction. Of course that happened.

Host: Amazing. That will conclude this installment of Investor Stories. If you're enjoying the program and would like to see it continue, take a moment and leave a five star review in itunes. Okay, that will wrap things up for today. Until next time over. Prepare, choose carefully and invest confidently. Thanks for joining me.

Jake Saper: It's m.