552 Killing It Creative Destruction

Welcome to Breaking Banks. The number one. Connecting.

Show. On this episode of Killing It, our guests went from being a software engineer, to an investment banker, to founding a community that supported the next generation of FinTech founders. He’s then brought on to become an advisor and eventually a founder of the FinTech team at Andreessen Horowitz, better known as A16Z.

And now he decided, rather than stay with one of the premier firms, he wanted to venture out on his own. And he is now the solo general partner and founder of the FinTech investing angel precedence C-stage fund Cambrian Ventures. Meet Rex Salisbury, backing early stage companies as he shares his journey and founder stories, his path, motivation, and the sport that ultimately led him to being a solo fund founder, after clearly being bitten by the FinTech bug.

He shares his thoughts on putting talents and strengths to good use, creative destruction, and how he thinks about failure to get you where you want. And in short, he’s killing it. Okay, so we are delighted to have Rex Salisbury of Cambrian Ventures joining us.

Rex, thanks for being here. Good to be here. Thanks for having me.

Well, we are delighted. We know you’ve been killing it out there for a long time. So we appreciate the opportunity to chat with you.

When you say killing it, given the subject of the podcast, I don’t know if you’re suggesting that I’m doing terribly or well. It’s hard to, but the ambiguity is enlightening and enjoyable. Exactly.

That’s what we’re gonna parse out over the next 30, 40 minutes. So to start with that, maybe for context, Rex, could you give us just a little bit on kind of your journey into fintech and specifically relative to some of the other folks we’ve talked to as part of this podcast series, your entry point into fintech was a little bit different, more of a community-oriented entry into the fintech ecosystem. So can you kind of give us the quick explanation on how that happened? Yeah, so I built a community and then accidentally that pulled me into investing and advising.

I’ll touch on that, but I’ll give you kind of a full story to help orient you, if that sounds good. So I’m actually calling in from Jackson Square right now, downtown San Francisco. And my first job in fintech is just about two blocks from here where I helped start, not a founder, but just as a software engineer, a direct consumer mortgage company called Syndio.

And that was in early 2010. So a long time ago, I was an investment banker. I learned a lot and I hated it, which I think a lot of people who’ve done investment banking can relate to.

And while I was doing investment banking, I was watching how fintech was starting to change the world of financial services. This is in the very early 2010s, right after the Great Recession. And you could see that innovation was starting to climb up the stack from the low value, high volume transactions to higher value, slightly lower volume transactions.

So at the time Lending Club has happened, SoFi was working and I’m like, I know what’s next, mortgage. And so I was working on one of the co-founders of SoFi. He was the CTO of this new company, Syndio.

I worked on a direct consumer mortgage company and we failed. I wouldn’t say miserably because I actually had a great time, but we failed. It turns out mortgage, while a much bigger market is a very, very hard market.

I still love the mortgage market. I’ve done some investing in it, but as many operators have spent time in this space and then become investors, you have kind of a love-hate relationship. So anyways, just a few blocks from here, back in the early twenties, was working on that company.

And that was a really special time in the ecosystem because a lot of other early companies in FinTech were just starting to reach scale. So like the Robinhoods, the Credit Karmas, the Stripes were going from maybe 60 to 100 to 200 to 300 people. And for the first time you had a bunch of technologists that were learning about financial services at some degree of scale, co-located in a certain area.

And I was like, I wanna talk to these people who are building really interesting things. So I started a community called Cambrian, where we bring together really interesting people to talk about something they built in the last three, six months, a year. Could be a new product or feature, or often it’s an early stage company.

And so the story is the company that they’re building. And that community is called Cambrian. We did monthly events in San Francisco and New York and just grew really large over time.

I loved my day job as a software engineer, but I realized I was getting a lot more energy from doing ecosystem level work. And so in 2019, Cambrian’s running monthly events in San Francisco and in New York, doing biannual summits, quarterly job fairs, biannual co-founder match. We have like 20,000 folks on a newsletter.

We have 2000 founders in the Slack community today. And I’m like, look, I’m just getting more energy. I started doing angel investing.

I’m getting more energy from this ecosystem level work than I am from working at a specific company. And so I quit my day job with the intention of raising a fund. And I got to know the Andreessen Horowitz team.

It was an amazing team. Through the work I’d done with Cambrian, the community. And they’re like, look, we’re gonna build and scale our FinTech practice.

Why don’t you join us and help do that? And so I did that for two and a half years. And then Jason was earlier saying, I made the irrational decision to leave a really great team and a really great space to go and start my own thing. But Jason, starting any company is a bit of an irrational act.

You can’t. That is entirely fair. But I mean, talk about the most 16 recognizable letters in the alphabet is Andreessen Horowitz.

How did your wife take this? What did your mother say when you said, I’m leaving from the top, but I’m gonna go not only go do something hard, I’m gonna go do it solo. For anyone who has a life partner, they know that the life partner is a silent co-founder of any endeavor. And so she was very supportive.

And we were fortunate that she was, she’s an executive at Guild Education. Everything was going well there. And so we were in a good position for me to be able to go out the risk spectrum.

I’m curious. I’m curious what it felt like to leave such a recognized brand where entrepreneurs flock to you, you can pick up the phone and every co-investor would respond. Was it harder when you got out solo? I mean, the Cambrian brand was known, Rex is known as a person, but it’s certainly not like having Goliath behind you.

Yeah. So when I was at A16Z, it was focused more on like A’s and B’s, occasionally seeds. That’s a different part of the ecosystem.

I like to think I have like a decent brand, certainly not as universal as A16Z brand, but for like people in the know, at Pre-Seed and Seed and FinTech, I have at least like a reasonably good brand and connectivity. And so to me, actually, what was surprising is many ways in which my day-to-day did not change. I’m still spending most of my time talking to entrepreneurs.

And one thing that I love about my job is that now I actually get to spend even more time with founders than I did at A16Z, just because the model that I built, and this is one of the reasons I started my firm, affords that. Specifically, it means that instead of writing two checks a year into two Series A’s companies, maybe a little bit more, maybe a little bit less, I now write about 10 checks a year at the Pre-Seed and Seed into companies. And so I spent a lot more of my time working with founders and seeing all sorts of different parts of the market and different business models being tested.

And as someone who really loves learning, I think one of the best ways to learn is A, to just have a broad purview and lens into the ecosystem, which being an investor reports that, but also is having a seat at the table for the companies that you support. And you’re able to do that better at the Pre-Seed and Seed where you write more checks than when you write just a few checks. And this was ultimately pretty early in my venture career.

I was like, this is something I’m more excited about to do for the next 10 years than like a much smaller number of deals. And that also aligns well by strategy. At the Pre-Seed and Seed, my goal is, I provide network connectivity.

And so I’m very involved in the early years of the company’s formation, trying to provide connectivity to customers, first hires, channel partners, infrastructure providers. You know, I send you both companies in my portfolio, but also companies I’m talking to who are selling to banks because I’m like, Jason is an amazing person to talk to because it turns out he has connectivity to over 70 banks and his whole job is help them find great tech to implement, right? And so I spent a lot of time just collaborating with the rest of the ecosystem. So I find it’s been a good, the theory was that I would enjoy doing it.

It’s very stressful for a period of time, but now I found actual practice has been that. I get to spend a lot of my time supporting entrepreneurs, which is awesome. So- Was there ever a point when you were starting the fundraising that you questioned where you’re just like, what the hell have I done? I mean, fundraising is always hard.

And I think, you know, perhaps nowhere near as hard is to build a fund as it is to find product market fit in the company. But I find raising from LPs can be a little bit harder because you don’t have product and pain that they can appreciate. And they have lots of choices on where it could go.

Is there anywhere in that journey you’re just like, yeah, this was a bad idea? So I will say one thing that’s very hard about making the decision to start a fund, you know, starting a fund versus starting a company, there are different things. It’s not completely apples to apples. I think there’s a lot that makes it harder in terms of starting an actual company than starting a venture firm.

But one dimension along which you can have more existential angst about it is the time horizon for starting a fund. Starting a company, if it doesn’t go well, it’s two, three, four years. If it goes well, it can be much longer than that.

And you’re gonna have like some really steep, you know, peaks and valleys along the way. For fund is much more stable, usually, almost always, because, you know, raise a fund, you deploy for 10 years. But you are making a very long-term commitment.

Because when you raise the first fund, it’s a 10-year vehicle, two, one-year extension. That’s 12 years. But really what you’re doing is the LPs who are investing in your fund, they’re saying, we’re taking a bet on you.

This is your first fund, right? You don’t have as material of a track record. Even if you have a track record outside of this fund, you don’t have a track record for you running your own brand and your own strategy. So we’re taking a risk on you.

And when you’re successful or start to be successful, we want you to raise subsequent funds. So really, when you’re raising that first fund, you’re signaling to the folks supporting you, you’re gonna raise three funds. So really what you’re doing is you’re saying, I’m gonna do this for at least 15 to 20 years.

And that, I think, is the most stressful dimension for people who wanna get in venture. And that is the thing that I kind of reflected on and early on gave me the most stress, is like, I’m pretty sure I wanna do this, but like, man, 15 plus years is a long time. Now that I’m two and a half years into it, I will say I feel very comfortable with that.

Ask me another two and a half years, and maybe I’ll be like, oh man, I don’t know 15 years. I’m kidding, but so that is one dimensional, which I kind of reflected probably the most. So one thing that’s interesting to me about the move from, as you were saying, kind of series A, series B to earlier stage is, as you indicated this, you’re writing more checks.

The expectation is that you’re gonna swing more and miss more. How do you think about like process versus results, especially over such a long time horizon where it’s like, ah, I feel good about these investments, but there’s no way to know. And along the way, I would imagine that you as an investor, and then obviously the founders that you’re working with experience a lot of like negative signals and doubts and, oh God, I don’t know if this is gonna work or we have to pivot.

Like, what’s it been like navigating the psychology of investing early stage versus later, particularly leaving sort of that well-feathered nest that you came out of with Andreessen? Yeah, so when you’re going earlier, if you’re a pre-seed and seed fund, one thing I like about it is I just invest the pre-seed and seed. I’m not somebody who’s gonna then go on and lead the A or the B. So you can just have a very honest and open relationship with the founder from day one about, is this working? Do we need to change the direction? Should you raise the round? If so, how much? Should we shut things down? And so you’re aligned in terms of being able to be very open about the direction of the company, because there’s not like, oh, I have to posture with my board member because if they did the seed, I have to have them in the A. And if they don’t go in the A, it’s gonna be negative signaling risk. And so that was something else I thought about in terms of how you structure the fund is making sure you create the incentives where you can be very open and honest, bilaterally with the founders that you support.

What about the personal element of that? I’m feeling this, because I’ve got a lot of the inbounds now where I was an angel or from the fund into some of these early stage deals, and they feel like they’re letting me the person down, which I find so hard, right? Because I’m like, we bet on them, but want them to be mentally healthy and not carry that like a scarlet dollar sign upon their soul that they have to keep trying to do something that’s impossible. Yeah, and I think part of that is just how you show up every day, week, month, however often you interact with them and just the kind of dialogue you have. And so I will have some folks who I think soon at some point in the portfolio, get to a point where it’s like, okay, we’re not really sure if it’s gonna keep working.

As long as you’ve had an open and honest dialogue beforehand, I think it’s harder with like angel checks because angel checks, you might not have been as involved with the company, whereas I’m pretty involved with them and I’m pretty open dialogue. And so those actually can be the hardest ones because you’re not really, the founder isn’t actually sure where you stand on the spectrum. But one thing I like too, again, this goes back to finding a model where you can be very supportive of the founders is, if you have a model that accommodates having losses, like that’s okay.

You can be very open and honest with it and you don’t have this existential angst. It can actually be very hard inside of a large firm. If you’re making a few bets, you’re kind of signaling that you have high conviction that things won’t go wrong.

And so you are incentivized to be like, oh no, like everything’s fine, right? Especially when you’re just getting started. And so I think that’s often why founders will have more stressful relationships with partners at bigger firms. And even though the firm itself is very comfortable absorbing losses, that individual partner has a smaller book and it’s much more meaningful for their career if one of them goes wrong earlier on.

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Learn more at alloylabs.com. Alloy Labs, banking unbound. What do you find to be some of the, I guess, almost kind of like demographic differences from a founder perspective? Because the other thing I’ve been really curious about as it relates to just dealing with failure and sort of understanding the nature of the entrepreneurship journey is that a lot of folks, they’re starting their first company, they’re navigating a very different set of challenges in just terms of like learning how to be an entrepreneur, but doing it in a real setting with real stakes versus multiple time entrepreneurs or entrepreneurs who are sort of getting to it a little bit later in life. Do you have observations about just like, in terms of the nature of the founder themselves and their past experiences, how they deal with adversity or how they deal with losses? Because obviously it hits everybody, but I would imagine it hits a little different based on your experience.

Yeah, I would say about 70% of founders in the portfolio are repeat founders, which means they’ve lived, almost certainly lived through market cycles. And a lot of the folks who have been repeat founders, even if their company has been successful, they’ve been through some really hard times. And a lot of them, the first company was not a resounding success, right? It was not that thing they were going through.

So they’re just familiar with what that feels with, as well as just some of the nuts and bolts of starting a company, running a company. They don’t create quite as much existential angst. And so I think they are just more, you gotta focus more on the fundamentals of the business and making it work as opposed to other kinds of things.

Part of that is just, if you look at the ecosystem, I have a podcast, I interview founders of scaled companies. And if you talk to like Ken Lin from Credit Karma or John Stein from Betterment or really any founders getting started in like right around the great recession, there are all of these existential questions for the business. Like, okay, I’m starting a company.

Who should my co-founder be? I don’t know. I haven’t started a company before. There are no fintech companies.

Like, do I get another banker to be my co-founder? Do I get another technologist who doesn’t understand financial services? So it’s like, how do you put together the founding team? And that’s like, okay, how do you recruit the founders? Then how do you put together the founding team? Same question, but different set of people. And it’s like, who do you raise from? There are no fintech funds 10 or 15 years ago, right? And then it’s like, oh, I need to build this thing. I’m a wealth earner at Betterment.

I need access to an API for stock trading. Apex like just came online a little bit after or they were online, but they just opened up to the wealth earners at Betterment a little bit after those companies got started. And so they’re existential questions around infrastructure.

So founders, team, capital, infrastructure were all existential questions. Whereas today in the ecosystem, it’s not because the ecosystem has grown up so much more. These companies have lots of the existing successful companies have scaled and they’ve spit out individuals who actually understand how a lot of this stuff works.

And so it means you’re also just able to, as a fintech investor, find people who have more experience than was true 10 years ago because the ecosystem has more size to it. So question on that front, is it almost too easy to get into business now that so many barriers have come down that you see a lot of products and services that closely resemble each other, or you get started in one business and you move laterally and there’s a great convergence of too many things because you don’t have to commit too deeply to one idea? Yeah, if I look at my portfolio and it’s about 30 companies now, I put them in like 11 different categories. And a lot of those companies in each of those, so I just wanna say there’s a lot of different kinds of companies being built.

And then the companies that I’ve backed and there’s kind of like, they’re all very different from each other. So if you know where to look, there are a bunch of unique ideas. However, you are right that the infrastructure has made certain kinds of ideas very easy.

And like the old joke used to be, there are just hundreds of neobanks for every single different demographic. So that’s not happening anymore because something else is going on in the banking and service ecosystem that makes it harder to get partners. So there are gonna be certain categories that have lots of folks because it’s easier, but it’s important to remember there are also lots of other categories that are still unexplored and novel combination of products and ideas that are still unique.

And so you can both have certain areas like seeing too much and then lots of space that’s still unexplored. Yeah, I mean, the other part of that that I think is really kind of interesting is along with the infrastructure that’s now available. And to your point, like regulatory changes and other things that have made certain categories more difficult and opened up opportunities in other ones, the macro expectation around performance has changed, right? And I kind of find myself sometimes forgetting for a second that SPACs were a thing briefly.

And then I remember and I’m like, oh my God, this is crazy. Or I’ll come across a company that went public via SPAC and like I’ll flashback to the Halcyon days of 2021. But I mean, you’ve been investing over sort of Zerp and then kind of coming out of Zerp into this new environment.

How have the sort of macroeconomic changes affected LPs? How they affected founders? Like what’s that shift been like in navigating that? Because I get a macro level beyond the infrastructure point, that seems like the other thing that’s really changed over the last five to seven years. Yeah, I think there is just a much greater focus on capital efficiency from day zero. And I started investing on the fund right after the market corrected in 2022.

And so all the men, again, about 70% of the founders are VP founders, so they’ve lived through cycles. They know the danger of overspending, especially if you’ve over-raised. And they also realized that overspending wasn’t necessarily that helpful for them to find product market fit.

So there is just much more in the water to think about like, what are the fundamental needs of the business? How do you do as much as you can with as little capital? And I’ve got some companies that are starting to scale and a lot of them are projecting cashflow break even in 12 months. Will they get there? Probably not. Totally fine.

But was that even part of the conversation two years ago? No. And so just that shift in attitude and expectation has been interesting to watch play out. For those that aren’t gonna make it to cashflow break even, right? Where the world becomes your oyster.

One of my favorite quotes from one of our first angel investors was revenue covers a lot of sins, profits cover all of them. And I think a lot of the market is learning that. For those that reach a turning point that they either need to make the decision to wind down, try and find a buyer, a soft landing, or frankly give the money back for what they have.

How do you help coach either those you advise or invest in? How to think about those decisions? Yeah, if you’re going through that process, part of it is just having a longstanding open dialogue where you’re revisiting what’s going on in the business every month. And so that’s not a surprise for either one of you where you’re like, look, it’s getting closer to maybe it’s not working. And figuring out what that’s like.

I’m also fortunate, like, I just don’t have any companies that have really hit that yet because it’s two years in. And we have a bunch of really great founders who have executed well. But once they start getting there, a lot of them will know it too, right? Like they’ll go through two or three pivots.

And then after that, it’s like, well, you’re still pivoting. Let’s try one more, but then let’s like figure out a timeline under which you’re gonna pursue alternatives. And again, because I don’t have like a, I am set up to be able to support people in that way, in a way that’s open and transparent.

It’s not something that I have too much angst about. And I feel like it’s gonna be, it’s not like people are gonna have to play hide the ball. It’s like, oh no, like things are totally fine.

You’re killing it. Yeah, yeah. Well, and I had forgotten this as well, but you actually invested in a company that helps to sort of speed up the process of shutting down a startup.

What, how does that part of the ecosystem kind of work today versus how might it work in the future? Because some of the other folks that Jason and I have talked to actually found that the process of like, okay, we’ve decided to shut down. We’ve decided to navigate this. It’s really like pulling teeth.

Like it’s an awful experience. There’s a ton of paperwork. It’s just really like unpleasant.

I think we don’t necessarily spend a lot of time thinking about how can we make the backend of the entrepreneurship journey a little easier and more painless. But tell us a little bit about that. Yeah, I think it’s probably one of my most known portfolio companies, but also most misunderstood.

But also if you’ve experienced it, you understand the problems. And let’s just start with the problem. If you shut down a company and I’ve had to shut down, just like a small holding company I have that I used to run the events out of.

And it took me like two years and my accountant tried to do it and it just sucked and it didn’t work. And then it turned out they did it wrong. And then I got like tax notices from I think California and Delaware.

Oh my God, this is so annoying. And this was like the simplest possible use case. If you’re shutting down a tech company or a FinTech company, especially that maybe has legal entities in like five to 10 to 50 states that has licenses, that has, it’s actually quite a bit of work and no law firm really wants to work with you because A, they don’t know how to do this very well.

And they’re not gonna be getting future billable hours because you’re going away. No accounting firm, they don’t really specialize in this either. So there’s actually very little support for something that can leave you as a founder personally exposed to a lot of legal liability at a time when you just want to move on.

And so the company’s gotten a lot of press because there’s kind of product moments that are like, oh my God, tech companies are shutting down. Here’s this company that’s like making money by helping shut companies down. But for anyone who’s been through the process, they understand that that’s actually something that’s very much needed.

And then for anyone who understands how the economy operates, you realize it’s not actually a thing about where we are in the tech cycle right now. There are about 700,000 businesses that are created every year. And the company, by the way, is called Simple Closure.

So simpleclosure.com. If you or someone you know is thinking about shutting down, you can go check it out. Dory’s the founder. He’ll probably reach out to you directly if you reach out on the website.

So 700,000 businesses are started every year. The natural part of having a dynamic economy is creative destruction. So we have about 700,000 businesses that shut down every year.

And you need to have a service, not just for tech companies, but for all sorts of companies that allows you to do that gracefully without exposing the founder to undue risk. And so that’s what Simple Closure does. Now, if only that had existed for fintechs, because let me tell you the fun of shutting down Perk Street where it was not a simple events company, but we had to move people’s money and close out PII and the everything else.

Yeah, yeah, totally. Not fun. So Rex, as you think about the direction where fintech is headed, what are you most excited about on new areas to explore? Yeah, so one is that there are just so many really good founders who have deep domain expertise and I get to talk to them and they get to teach me something new and exciting.

And so just the caliber of founder has gone up. So that’s awesome and very exciting. I also think it’s possible now to build multi-product companies from day one because the caliber of the founder has gone up and infrastructure that’s available to the right people with the right track records, right? It’s getting harder to get bank partners and that sort of thing right now.

But for the right founder, you can still get it done. The ability to build a multi-product company from day one is very exciting. You think about a lot of the companies that were successful in the last wave of fintech, there’s this famous picture of the Wells Fargo homepage from 2014 and it maps the fintech ecosystem on top of it and says like, oh, we’re unbundling the bank.

Here’s the point solution for all of these individual pieces. And that’s cool. But what’s really cool is actually re-bundling the bank, taking a few of those products, putting them in a novel bundle and then figuring out differentiated value proposition where maybe you commoditize or compliment in a way a bank could never offer you, you know, a very simple example, a high yield account.

It’s like, that’s how they make money. And you’re like, of course we have a high yield account because we’re a vertical SaaS company that offers workflow efficiency and maybe lending or payment processing and idle cash. Like we don’t really need it to generate flows.

And so like that re-bundling because you have better entrepreneurs built on top of better infrastructure is something I see across the portfolio. But what I really love is that within the portfolio, there’s so many different kinds of ideas getting started. I think as an outsider, it can be hard to see that this is happening because let’s say you don’t work in fintech ecosystem.

You like maybe hear about the same kind of big companies. You don’t hear about like the new small ones that are growing quickly or maybe you’re inside the fintech ecosystem and you have another observability bias problem, which is you work in sales at Plaid and you’re like, oh my God, all of these companies are the same. They’re like all doing the same things.

And then I talked to my friend who’s in sales at Plaid. So by the way, like less than 15% of the companies I’ve invested in use Plaid for anything, right? So you think you’re seeing like the universe of opportunities and really you’re just seeing a subset of the universe of opportunities. And so just the breadth of what’s going on, if you know where to look is very exciting, but it won’t become apparent to the outside world until some of these companies start to reach scale.

Awesome. Well, Rex, we wanna wrap up with one final question, I think, which is one that we always try to ask, which is based on everything we’ve been talking about, there’s someone who’s listening to this podcast who is sort of in the kind of ambiguous, as you said, sort of killing it mode where things might be kind of going well, but there are some of these sort of pressures that are pushing on them, or they’re feeling like they’re not quite sure kind of where to go, particularly for like early stage founders that are just trying to get to that product market fit and are maybe just not sure what they’re doing. What advice would you give to them for kind of how they can think more clearly about the path in front of them, how to think about failure, how to think about just sort of the ups and downs of that early stage journey? So one is that find someone else to share that burden with, that can be your co-founder, that can be other early investors.

And two is if you don’t feel like there’s anyone you can share that burden with, you might be more wrong than you realize in that other people are already aware that you probably have this burden, whether that’s your early investors, your co-founders, other folks. And talking about it openly with them is gonna be better for you, and it’s actually not gonna be as big of a shock as you might expect. So the biggest thing is just find people to talk to and reflect on this with.

I think that can be co-founders, the right early investors, and that can also be other founders in your network. Fantastic, Rex. Well, thanks for sharing the journey.

Excited to see Cambrian become the next powerhouse within the venture community, and excited to see all of the success you’ve enjoyed so far. Thanks, Jason. Thanks, Alice.

Thank you. That’s it for another week of the world’s number one fintech podcast and radio show, Breaking Banks. This episode was produced by a US-based production team, including producer, Lisbeth Severins, audio engineer, Kevin Hirsham, with social media support from Carlo Navarro and Sylvie Johnson.

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