The Exchanges

Q Were you poached by the team at USV or did it just magically happen over a couple of dinners or lunches?

A A couple months after Uh, Fundera was acquired by NerdWallet. I kind of Normally what happens after you sell your company in one of these businesses is you, you work really hard for a couple months, and then you're kind of like, ooh, things are kind of on autopilot and things are going well, and you gradually extract yourself from the business and start thinking about what a succession plan would look like. Um, and while I was doing that, I reached out to Andy Weissman, who's a partner here and been a friend of mine for a long time, who is actually the, the lead investor in GroupMe's first round of financing when he was at Betaworks. And Andy and I have also sat on the board of a company called splice, which was founded by my group, me co-founder Steve Martosi, who is a two time usb founder. Um, so we've known each other for awhile. I reached out to Andy and I, I said, Hey, can I be your intern? Um, I've got some free time. Um, I'm not going anywhere for awhile, but I would, you know, love to come in. Occasionally and help you and hang out. You know, I had been angel investing, uh, in tech startups for over a decade then. I had been an investor, uh, and an LP in USB's funds for over a decade as well. So, was intimately familiar with the firm and the people here. I was very curious to learn more about how USB worked internally. I felt like I had a really good idea of what everyt…

AI assessment note: “I reached out to Andy and I, I said, Hey, can I be your intern?”

Q Does it make you miss being an entrepreneur? Like, do you get energized when you're meeting with, with entrepreneurs and you're like, ah, dang, like, I wish I had my team around me. I wish, you know, we were like celebrating new launches or something like that. Like, how has that aspect like changed your personal mindset? Uh, because this is a completely different kind of career.

A Um, sometimes I miss it. Uh, you know, when you, when you reflect on your experience building companies, you really romanticize it a lot. You kind of remember all the glorious achievements and fun times and like milestones, and you suppress all the terrible shit that you've endured and all the fucking trauma that you've accumulated and hardship. And by the way, Somewhere between, like, 90 to 99% of it is that shit. It's that hardship. It's the really difficult stuff that, for some reason, like, you've just, like, pocketed in some corner, and you never really go and revisit. And only one percent of it is like the, yeah, we did it, everybody. But for some reason, you only think about the, yeah, we did it, everybody moments. I don't know. That's just, I think it's just, like, a funny reality of it all. So, um, yeah, I think about the, like, yeah, we did it moments a lot, but I also like to remind myself of, you know, the 90 to 99% of the time of where life wasn't like that. And you're kind of just wondering, what are you doing? Why are you doing this? What's going on here? Uh, so sometimes I have moments, you know, if I'm like sitting in an entrepreneur's office and there's like eight people all sitting there in the same room next to each other. And they're like pointing at each other's monitors being like, look at this, we're about to ship this. Or what if we do that? Or why don'…

AI assessment note: “sometimes I miss it. Uh, you know, when you, when you reflect on your experience”

Q amazing team. Uh, it's the real deal, like, it's, it's really phenomenal. Um, what have you, like, what do you think, given your experience, Being in the founder seat, working, you know, getting funded by different funds. What do you think USV does different and what do you think they do better? And is it a secret sauce or is it, you know, they're just, they just have some magic.

A Well, There is a magic and I think the magic is a bit of a secret sauce. I think it's a, it's a, it's one that is constantly evolving too. So I will give you, um, my point of view from before when I joined USV. Um, because I think there's two different things. One is, uh, how does the firm operate after it makes an investment? And then there's the, what happens before, um, USV makes an investment. I think that USB's reputation, and I'm gonna, again, this is through the lens of me before joining the firm, like why I love the place so much. You know, I, I sat on the board with USB for a long period of time, I guess still do, uh, in my co-founder's company, and I've seen how the partnership behaves through good and bad. And I have compared and contrasted that with my own experience building companies and the ways in which The partners here collectively, not even as individuals, support entrepreneurs is somewhat bewildering to me. And in some instances, almost irrational, um, with regards to like how kind and supportive and endearing and genuinely reverent they are towards entrepreneurs. So, um, a couple of examples. One is how, um, partners behave in board meetings. And I can kind of go back to that Brad example. Uh, from back at Tumblr where it's like, no, it's not about being the loudest voice in the room. It's actually just about listening, synthesizing, and then contributing w…

AI assessment note: “how kind and supportive and endearing and genuinely reverent they are towards entrepreneurs”

Q Yeah. Yeah. As we wrap up, so two more questions. Uh, you're in New York. You've been in New York for a while. You've been a part of the tech scene. You're part of the fabric of the tech scene of New York. How has it changed in the last couple of years? Has it been resurrected after COVID? What does it feel like being in New York City?

A Well, when I started here, you could get everybody in tech at an event in, in Madison Square Park. Now it's the thing. All however many of us there were. 300? 400? And in fact, that happened like every year. I think Charlie O'Donnell used to host a Shake Shack event there. And now everyone seems to work in tech, or at least tech has touched everything. So, in some ways, you know, it's kind of like mission accomplished. Congrats, New York. In other ways, it's kind of sad where you went from a world where you kind of knew everybody, and it was this close-knit community, and now it's not that. Now, yes, there's a, this massive tech network in New York City, but there's all these kind of, like, microcosms of it across all these different industries, so it's split. You know, horizontally and vertically, and that's incredibly cool to witness and see. You know, there's always a little bit of me that has maybe a little bit of nostalgia for the way it once was, but we are where we are, and I think it's only going to get bigger and better, and it's just amazing to see how quickly everything changes. The other thing that is so fascinating to watch, you know, growing up here, You, you would always read these stories about kind of like these mafias that existed on the west coast. A group of renegades that start a company together, and they hire all these talented people, and then that compa…

AI assessment note: “Now, yes, there's a, this massive tech network in New York City”

Q Going from Fundera to taking a break, how did you manage your time while you were on a break? Did it take a while to transition into, like, okay, I'm not building anymore, like, let's take time to, like, slow down, or were you kind of still very active during that period?

A Yeah, well, I had never taken time off, um, in my entire career. Like, the day after I graduated from college, I started at Tumblr. The day after, you know, I left Tumblr, well, really, many days before I left Tumblr, like, GroupMe was out in the wild. And the day I left Microsoft, after having had sold GroupMe to Microsoft, I started Fundera, like incorporated Fundera. So there, there really wasn't a single day of my career where I didn't know what was coming next. And, um, you know, towards the end of my time at NerdWallet, I, I kind of got, I started to think, well, maybe I should think about venture. And I, I, I ended up talking to a large firm Um, for whom I have great respect for, and that process, starting that process kind of made me realize that, no, I need to pump the brakes and really clear my head to figure out what it was I was going to do next and try to be deliberate about it. Part of that was informed by the fact that, you know, when I left GroupMe to start Fundera, um, I, I very often felt While reflecting on that process that I didn't take enough time and I wasn't deliberate enough about what I wanted to do next and perhaps maybe even had picked the wrong idea or space and had I been more thoughtful about it, um, maybe life would have been easier and I would have picked a better idea, um, a better market perhaps. I don't know if that's true or not. And, um, I …

AI assessment note: “I need to pump the brakes and really clear my head to figure out”

Q exposure to the fund over the years, you've gotten to know them much Now you're on the inside, now you have exposure, and it's part of your day-to-day, um, being an investor. What's your perspective of being an investor now that you're kind of in it, and um, you're seeing the world through that lens? Are, are there any surprises? Are you liking it? What's, what's been the transition like?

A Let me think about the best way to answer this question. I think There are many ways to answer this question, and I can really only answer it through my own personal lens, which is, you know, being a venture partner here at USV, which I actually think is unique and probably quite different than being an investor most anywhere else. Um, and I'm new here, so I can say those things. This is a special place. Um, I love showing up to the office every single day and, and being able to interact with all these amazingly brilliant people in, in person, and I am in, Learning mode. It is an incredibly humbling experience in many ways. Um, because I am so new at this, you know, I've come from a thing where I got like reasonably okay at building companies, like had some semblance of an idea as to what I was doing and how to get something off the ground from zero to one, and then from one to, you know, somewhere beyond that. And now it's like, Wow. This is a, this is a totally new thing. So I'm just trying to be as much of a sponge as I possibly can be. Being a thesis driven firm actually means, um, hearing the conversations they have, uh, about supporting entrepreneurs that have been in the portfolio for over a decade. Um, it's, there are so many like novel vectors of like Things that I'm beginning to understand and learn and it's constant. Um, so the transition has been in many ways, extre…

AI assessment note: “the transition has been in many ways, extremely organic and fluid and seamless”