272. Staying Competitive in the Seed Fund Boom, Success Metrics at the Fund Level, and the Shifting Equilibrium of Investors and Founders (David Goldberg)

David Goldberg Alpaca VC

David Goldberg of Alpaca VC joins Nick to discuss Staying Competitive in the Seed Fund Boom, Success Metrics at the Fund Level, and the Shifting Equilibrium of Investors and Founders. In this episode, we cover:

  • Walk us through your background and path to VC
  • Tell us about your shift from law to finance and to becoming a founder of FreshNeck?
  • Whatโ€™s the thesis at  Alpaca VC?
  • Talk to us about your Field Studies and why you do them.
  • How do you develop a thesis on consumer behavior, trends, and how they will evolve in the coming years?
  • Similar to us you do a lot of OKR and KPI measurement and tracking as a firm… what are some of the most important metrics you track that should ultimately lead to the right progress?
  • What about w/ the portfolio companies?
  • Do you have systems and processes on the front-end, pre-investment
  • You are a remote team of fund managers in NY, CO, and FL… what are the advantages and drawbacks for startups with w/ remote teams?
  • Do you think the center of gravity is shifting away from the Valley?
  • You recently invested $2.5M of your personal capital into 6 Black and Latin fund managers – what drove this decision?
  • What are your thoughts on Carta X and new liquidity for late-stage equity?

Guest Links:

Transcribed with AI:

David Goldberg joins us today from Miami Beach. He is a general partner at alpaca VC, a seed stage venture fund investing in consumer b2b marketplaces and global commerce infrastructure. Prior to alpaca, he was a founder and CEO at fresh neck, a subscription based men’s accessory exchange service. David, welcome to the show.

Hey, Nick, thanks for having me.

Of course, can you talk us through your background sort of your path to to fresh neck and subsequently alpaca?

Sure. I don’t know how far you want me to go back. It’s it’s a bit of a winding untraditional path. But I graduated school University of Miami went right back to school, I did a JD MBA in New York City at Fordham. I practice law for a couple years, I was an assistant district attorney and Kings County, which is Brooklyn, for those who aren’t familiar, then fell back on my finance degree spent a couple years at Merrill Lynch than over at Jeffrey’s the global investment bank before sort of letting the startup pitch get to me. And as you mentioned, founded fresh neck, I believe in 2010. Build that company to seven figures revenue at about three and a half years before ultimately selling at the end of 2013. From there met my partner, my original partner, Ryan Friedman, we started what is now alpaca formerly known as corrigin ventures, and we’ve been building it out for seven years since that’s awesome.

That’s awesome. Can you can you talk more about your shift, you know, from sort of the business in the finance world to, to founding this company fresh? Not?

Sure. I mean, I think you know, these days, if you want to be a founder, there are so many resources, you know, whether it’s people to talk to blog posts, to read forums, to join events to go to, that really didn’t exist that like back then it was trial by fire. And so I thought I wanted to do this, I jumped in, I made every mistake that you could probably make. And I figured it out as I went. But ultimately I took you know my experience as a customer and potential customer, I understood my own pain points about, you know, being a professional worker who didn’t really have the ability and access to the wardrobe that I wanted. And so I created the solution that I wish exist for myself.

Awesome. Awesome. And that journey was a how many years until exit. You saw

it from beginning to end. It was probably about four years, the first six or seven months, I was doing part time while still working at Jeffrey’s. And ultimately after taking enough, you know, meetings in the bathroom and sick days. I left on my one year anniversary to run it full time and then raise a little bit of capital.

Cool. and talk to us more about alpaca You know what, what funder Yon how how’s the progression been? You know, has the thesis evolved?

Yeah, so we are finishing up the investment period of our second fund. I’d say it’s been a gradual evolution in terms of strategy. Right. So one thing that separates us is that all three partners and we added a third partner last year, her name is Aubrey pagano. We have all been successful founders, CEOs from the New York tech ecosystem, right. So a big part of our ethos is, you know, being a real partner in the trenches, who has been on that journey before and who can inject some of that second time founder DNA, you know, into someone doing this likely for the first time, I’d say the real evolution is, you know, first fund, we were more of a participatory check, you know, writing a couple $100,000 often not leading, we’re now in fun to writing larger checks, giving out term sheets, setting terms, taking board seats, and really being that first phone call for founders

still at the early seed stage.

That’s all we do. And that’s probably all we’ll ever do

in any geographic constraints.

US and Canada, though, you know, based on our networks, especially pre COVID, all six of us three partners and three Junior folks being in New York. It’s about 50%, New York, 25%, Los Angeles, Boston, and then the rest kind of split across the country, including SF Miami, Chicago, Minneapolis, Charlottesville, Toronto and Austin, probably missing one or two in there now,

Charlottesville in there. Now, it’s been a couple years at school there. Talk to us, David, about your your field studies sort of approach and why you do those?

Yeah, I don’t think it’s a secret that the venture landscape has gotten more competitive. I don’t know the latest data number of how many seed funds, they’re out there, but it’s somewhere in the hundreds, I’d say yes. So while everyone will champion their networks and how great their deal flow is, and we’re no different we think to really get ahead of the game, you need to manufacture your own deal flow. And for us, that means getting really smart on a space getting to know everybody and coming with some referred to as a prepared mind to space before we actually meet the companies who are doing interesting things. So it starts with a hypothesis. We will then do what what is typically a 90 day sprint. We will talk to incumbents, customers, founders, investors will map the entire landscape. And we’ll build a pretty strong opinion on what we’re looking for what the red flags are, what the proper business model is. And about half the time it uncovers an immediate investment opportunity that we’ll take advantage of in real time. And the other half I’d say it leaves us armed with the information and prepared mind to act aggressively. When that opportunity does cross our desk.

How do you choose which areas to do these deep dozen or Sprint’s?

I, I’d say it’s really like the intersection of where we have expertise, passion and where you know, the tailwinds are going, you know, so right now, for example, we’re seeing a lot in remote work. I look at a lot of marketplaces. So trying to understand where the intersection of that maybe

got it. And I know you as a firm do a lot in the consumer space. How do you try and get a good read on, you know, consumer behavior, the trends, and where those are going, you know, over the next over the coming years?

It’s a great question. And I’ll just sort of give a caveat, right, we don’t do a lot of what I’d call a true consumer brands, right, we’re doing more infrastructure for e commerce or more digital consumer type companies. I think it’s really a combination of just like staying on top of the world and doing a lot of research. And that’s everything from understanding the incumbents, and what they’re seeing both financially and anecdotally, but also understanding what is going on, quarterback on on the streets or at the ground level and understanding leading indicators of consumer behavior. And we will interview customers, interview founders, interview investors, that ultimately we see about 1500 deals a year, and while we only invest in a hundreds of them, you know, provide important information of what’s going on at the earliest stages in their various sectors.

Got it? Got it, you know, similar to us, I was doing some research on you guys. And, you know, similar to us, you guys do a lot of okrs, and KPIs and, and measurement tracking, at your firm level, even, you know, what are some of the most important metrics that you track at alpaca? That, you know, if you win with those metrics, they ultimately will lead to sort of the right progress for your firm?

Yeah, it’s, it’s a great question. It’s something that’s pretty unique to us, we kind of geek out on some of that stuff. I think it just comes from our operator background. I mean, obviously, at the high level, you know, you’re tracking true performance of your portfolio. But but that’s typically a lagging indicator. And so for us, we’re trying to understand, like the success rate, or the leading indicators of a lot of our underlying portfolio companies, so for example, understanding growth rates, turns in retention, and then graduation rates, right from like, seed stage to series A, and then at a more granular level, like these will evolve every quarter based on what our priorities are, right. So for example, maybe we’re making a push into our own brand. And we’ll set KPIs around getting on podcasts, getting press quotes, we’ll try and quantify our networks and think about what series A and Series B investors, we want to build out a relationship, how much deal flow are we seeing from them, and we track all of this stuff in our database in our Salesforce?

Hopefully, we can be one of those, those little data points that that hit the dashboard, you know, at some point

gets a notch on the belt date. Well,

let’s so let’s go a level deeper. So you I imagine you also work with the portfolio companies in this manner as well, right? You You’re taking lead investments, I’m sure you sit down with them and at a strategic level, try and figure out where to focus and what to measure. Can you talk us through that process? how you approach it, how you think through it? And maybe is it customized, depending on every portfolio company? Or is it kind of a similar playbook?

I’d say we try and systematize the process as much as possible. That being said, companies are different personalities are different, and level of buying can potentially be different. But but we try and kind of set expectations up front and invest in like minded individuals. Before I get into the process, I’ll give a little bit of like the why and where this came from. Right. So on one example, and where this really started, was really because we thought this was most valuable for founders to have accountability to sort of prevent them from chasing shiny objects to get the entire team aligned with transparency, like all rowing in the same direction. And that’s worked out very well for us. And obviously, for them. The collateral benefit that we saw coming out of this, which really got us to double down is the level of granularity and confidence that we were then getting as an investor into how these portfolio companies were doing. Right. So when follow on decisions are potentially liquidity decisions came, we didn’t have to scramble to go look through years of financials and piece together a story that’s likely been framed in some way. We have these, like 90 day frameworks of here’s what we said we were going to do. And here’s how we performed. And then when that repeats, every quarter, we summarize them, we give our voiceover, we actually score them. So when you then look at it on an entire portfolio view, it’s very easy to plan out our cash flows as to here are the five top performers where we know we need to get as much money as possible. Here, maybe the bottom five, where we know we’ll never need to get more money into. And here’s everyone else that’s in between that is likely moving up and down on a quarterly basis. Got it? I love it.

How about on your investment process, you know, pre investment as you’re you’re bringing in top of funnel opportunities, filtering those taking meetings, you know, progressing some into diligence. Do you also have sort of a systematic and process based approach there? Or is it is it you know, more, everyone’s kind of just running their own deals and trying to find great founders?

I’d say it’s, it’s a systemized process as a seed stage deal sort of can be. You know, it obviously starts with some level of just screening, right? Like, does this fit our literal framework? Is it in a sector, we look at a geography we looked at and is the size of the round in terms directionally kind of what we do? And then I’d say, and what’s a little bit unique to us is, you know, we refer to the process as continual escalation, right. So instead of one partner or junior person, kind of running in their own swim lane from first meeting, all the way through, like deal metal and partners meeting and then bringing in the rest of the team to make a decision. We are continually doing temperature checks, understanding kind of how compelling an investment may be, what resources on the team may be helpful in either adding value and diligence in that investment. And so we’re pulling in team members on a constant basis, right? So in our weekly, all hands meeting, we’ll talk about 10 companies will decide as a company the two to three that are interesting, and what are the different chess pieces that we need to do to move that company forward as fast as possible, right, because at the end of the day, speed matters. When it comes to investing at the seed stage, I think the data shows that like, the first term sheet often wins the deal, something like 70% of the time, that’s not actually true at later stages. But for us, it’s very important to be able to get as much diligence done as possible in a shorter period of time. And obviously, there’s a balance to strike there.

And just to clarify, for the audience, you know, how do you how do you define the seed stage?

That’s a great question. And that’s evolving on a, on a monthly basis, it seems at this point, I think, for us, it’s, you know, a company that has a fleshed out product, right. And that doesn’t mean that maybe it’s built, but at least they know what they’re going to build versus, you know, smart founder, I don’t know what I want to build. But it’s something in this space. I think that’s a little actually too early for us and more, you know, Angel type money. But they haven’t found product market fit, right. So maybe they’ve raised a couple 100,000, maybe a million or two of they’ve raised a pre seed round, you know, and they’re raising now between one and $5 million to find that product market fit to test that product to find some distribution channels before call it raising a five to $12 million, series A, which is really about scaling on what’s already working.

Got it? Got it. You guys are a remote team of fund managers. I think the three partners are based in New York, Colorado and Florida, yourself being in Florida. What are the advantages of the remote team structure? And what are its drawbacks?

So we were not remote for the first six years. And really, we went remote March and we were a little bit nervous. Very quickly, we found ourselves being probably even more productive and those advantages outweighing the disadvantages, I think the disadvantages I seem to really come about. One is when dealing with founders missing out on some of those kind of cues, especially between founders, right? Like when you’re talking to three different founders on zoom, and they all have their little tiles on top, you know, it’s hard to understand their dynamics together. Whereas when you’re all sitting in a room, you can see who looks at who who’s interrupting who, whereas in zoom, everybody’s always interrupting somebody because, you know, there’s lags and it’s not actually their fault. You know, there’s there’s a bit of a personal backstory and personal value system that you can certainly ask the questions on a zoom meeting, but when you go grab a drink or a meal with somebody, there’s just another layer that you could pull with The second thing and this is more internally, I’d say is our junior team members, right? Who typically learn by osmosis, we used to sit in more of an open floor plan, you know, and after a phone call, he would pick up on something. And this is I’m referring to a specific junior team member on my team, who would say, Hey, I heard you mentioned this term, I heard you talk about retention this way. Can you help me understand what you meant? Right? Or I would hear him talking to a company and say, Hey, it sounds like you’re talking to a company that does x, have you spoken to y and z. And now we’re kind of missing out on that. So we’re trying to figure out a way how to force function that a little bit and create a little bit more one on one time sort of recreate that water cooler talk. But they haven’t really been big bottlenecks. On the advantage side, I think one, just every individual has been more productive and just happier, right? I think there’s a little bit of work life balance and flexibility. I know myself, I’ve shaved about an hour and a half a day off of commute and travel, you know, I get to actually have a meal or two a day with my kids, and can kind of go in and out of work at my pace and get things done. The other thing that’s nice is like, and this is a bit contrary to what you think. But we actually collaborate faster, because we’re not bottlenecked by needing to get together in a boardroom in the office. So what used to happen is like, Hey, we want to call them Investment Committee. Let’s look at our calendars and see what are all available at the office at the same time. Okay, Thursday afternoon, we’re now it’s Tuesday. And we literally jumped on a FaceTime call at 8pm on a Tuesday night, because we didn’t feel like we needed to do it in the office. And you know, that 48 hours getting that deal done may be the difference between winning or losing that deal.

Do you think there’s any unique challenges with the startups getting from zero to one or getting from, let’s say, seed to series A, that are remote versus those that aren’t?

The let me just make sure I’m understanding the question that the startups themselves by being remote versus not remote. Is there challenges in sort of hitting their milestones?

No, I, the question is more Yes, yes. About the startups, but founding teams that are remote. Right. So we talked about how you guys are remote and you started out together? Right? So your zero to one, largely speaking was together. So you could forge those relationships, you know, bonds and stuff. And a lot of startup founders know each other. Right? They come from a background, they didn’t just, you know, get put together by a recruiter, hopefully. But you know, I don’t know, have you observed? Or have you witnessed, like any differences in sort of that that progress in that process? You know, for the remote teams versus the non remote.

I’ve actually seen it play out both ways, right. And I don’t think there’s a right or wrong way to do things. But I think founders need to be self aware about their strengths, their weaknesses, and their culture. Right. I’ve seen some teams thrive in remote. And I’ve seen others. I don’t want to say crumble, but you see, the cracks in the armor really, really appear. I think the ones that struggle the most are ones who built out intentional in office cultures for certain reasons, and then we’re forced to go remote.

Mm hmm. Yep.

Personally, I’ve found like our team is remote Now, of course, because of the pandemic, and I found that the speed of progress is like, rapid, like, we’re moving at lightning pace, and our metrics have never been better. But every once a while we fall out of sync. And culturally, I don’t know, culturally, you know, it feels like a bit of a standstill instead of like a ton of progress. And so you know, I have no answers here. All I have is questions, but

it’s good. I’ve seen the same thing, I think, right? Your firm, my firm are similar in that we were not built intentionally to be remote. And I don’t know about you, but I don’t have a ton of experience of building and managing a remote team. I think that’s actually a skill set. And an experience that’s going to be in very high demand. Right? If you have built out I’ve seen this with engineering teams over the years, right, if you are a CTO, or VP of energy that has purposely built remote engineering teams, that is very different than a company just decided we’re going to go find cheap engineers in Europe, and having like someone not familiar with that, try and manage that. And so I think that’s what you’ll start to see sort of the ones who do it properly, and the ones who do it intentionally will have a tremendous competitive advantage and the others will be at a disadvantage.

You guys have been at this for for quite some time. Now. You’ve had success and things are progressing in the right direction. Right. Are you starting to see with this explosion of seed funds and everything I I just got done talking to Ed Sim, and you know, a number of other New York City investors. Are you are you seeing more more competition over time at seed stage.

Definitely. I mean, there’s no question about it. But the way that I’d say it is like, supply and I don’t know who the supply and demand are in this equation, I guess the demand is the startups. Both of them are up, right, like the number of startups and not just like numbers of companies created. I mean, like high quality, venture bankable, really smart people who, you know, used to be when I got into this over a decade ago, you were kind of a little bit of a quirky one, you know, or real, like technical person to get into startups. Now. They’re coming out of banking, P e, hedge funds, traditional companies consulting, so just the number of incredible companies and also the empowering technology to provide it. I actually think there’s room for both sort of the competition, and also the number of startups here. So like, I see it, but I don’t feel it in terms of like my underlying business, if that makes sense.

So it’s a good observation. I remember when I started doing this in 2013, or something, people would ask me, what do you do for a living? I’m a startup investor. A lot of people would say, what does that mean? And now like, if you say you’re a tech investor, or startup investor, most people get it immediately. David, do you think that the center of gravity is shifting away from the valley?

I do. And listen, I think for the foreseeable future, at least the next decade like that will still be the number one market. But I think the differential or delta between SF and everybody else has been shrinking, and will continue to shrink at an accelerating pace. And so going back to that question around, like supply and demand and the equilibrium between investors, and startups, I think there’s still a tremendous amount of investors. And we’ll be in those markets because of, you know, exit events and angel investors and spin up funds. But as access has gotten democratized, the places of value will actually be in all of the other call it tier two cities like Austin, Chicago, Miami, Charlottesville, places like that, where I think there’s opportunities where there’s going to be amazing companies built, especially with remote work as a catalyst. And there’s not yet a ton of investors who are playing in that pond.

Have you guys done an investment in Florida? yet?

We we did one investment in southern Florida before I was here. But it would not surprise me if another one gets done while I’m down here.

That’s great. It’s great. You all recently invested two and a half million of your personal capital into six black, black and Latin fund managers. What drove that decision?

I think it’s a couple things. Right. So I mean, one, we were all privy to what’s going on, you know, in the world. And I think we sort of realized how fortunate and privileged many of us were and, you know, we had access to systems that many don’t. And so we wanted to think about, how can we pay it forward in a way that really had maximum impact, right. And so we thought about everything from office hours, and mentorship and coaching to maybe hiring a junior employee, you know, to thinking about benchmarks in our own fund scout programs, venture programs. And ultimately, you know, I’m a big believer in my career, I’ll take a step back in my career, I was given an early opportunity to really deploy capital, right, and to be a Czech writer. And to me, that really accelerated my learning curve and the impact I was able to make both on my own career and in the ecosystem. So for us to be able to do that with rising stars and give them full sort of autonomy, to write 20, to 30 checks to build out their track records to have that trickle down to underlying underrepresented founders, to us was the best way to have impact secondarily, and selfishly, you know, we now have relationships with what we think are six of the rising stars who have networks and deal flow that look very different from ours and right, so to not only are they looking at different demographics of founders in different sectors, but they’re also geographically dispersed. One is in Cincinnati, one’s in Washington, DC. One is in Oakland. One is in San Francisco, one’s in New York. And so if we can just see, you know, what they’re doing and pick out one or two of the best from each fun, I mean, that’s 10 deals, you know, we only do 30 in a month.

That’s great. That’s great. You’re doing it if I’ll put you on the spot a bit, but if you could give these emerging fund managers or any emerging fund managers, like two to three pieces of advice, like if you nail it, you know, with these things, you can have some some success, you know, what are those, you know, salient lessons that that you’ve taken away from your almost 10 year career here that that you would provide to the nuclear

That’s a great question. One One, I’d say. And this is similar to how we think about founders working where you have to raise sort of funding in stages. every stage and in this case, it’s really every fund needs to be thought about of like, what are the proof points? What are the boxes that need to be checked, to get to the next fund, your first fund is not where you’re going to make the Midas list and get really wealthy. So maybe for you, it’s proving that you have expertise in a sector, maybe it’s proving that you can lead a deal. Maybe it’s getting allocation or working with certain co investors, everyone has a different strategy. But really think about what are those proof points per fund one? How does their step function then up to fund three, so on and so forth? Well, the second piece of advice I give is like, they’re all really, really smart. And I think they’re good call it investors, which means they can access good deals, and they can pick really well. But the part that’s often missing and was missing for me early in my career is learning the other side of the business, which is like the boring back end operations, administration portfolio construction. Right. There’s a difference, dude. Exactly. Exactly. And I’m still learning. You know, it’s it’s been a couple of years now. But I think it’s been really valuable, especially as you move from either Junior investor or angel investor to running your own fund. Yeah, it’s

it’s running a business. It’s not just running around cutting checks. I mean, it’s a totally different instantiation of what we do. Yep. What do you think about I mean, this is random, but news came out today. So I figured I’d ask you about it. Or maybe it was yesterday, you know, carta acts and sort of new liquidity and sort of the the latter later stage Marcus, whether it be for employees, founders, or maybe even folks like us, you know, what’s your quick take?

Quick take is like, it’s awesome. Yeah, I mean, it’s sort of been happening, call it on, like the underground black market for a while, right. And there’s these secondary firms and a lot of things going on behind the scenes. But anytime you have black markets like that, and lack of transparency, it’s going to be a really inefficient market and hard to get stuff done. So they can bring transparencies and efficiencies to the market in the same way that we’ve seen it across almost every single sector over the last couple of decades. To me, it’s it’s a win win, right? And for companies, founders and investors to have earlier liquidity options to me, will just attract more capital, and more intelligent, talented people to the ecosystem on both sides of the equation.

Yeah, I think we featured the carta guys known as he shares at the time, probably back in 2015, or maybe even 14, I don’t know. But I’m kicking myself for not banging down Henry’s door and getting them some money at the time.

Yeah, I don’t blame you. I, I’ll be honest, I scratched my head, I think at a couple of their rounds in the valuations. And I know there was only this like big long term roadmap that like if they had this wedge into really all the data of what’s going on on cap tables and rounds. And I think you’re starting to see it come to fruition as they get into third party fund administration and spvs. And now basically, like a secondary exchange.

Right, right. David, what resource Have you found really valuable that you would recommend the listeners? Um,

I think for me, and this is like a hard one to replicate. It’s not like just go to this website and read this book, build out a really strong peer group, right of people who are at similar stages in their experience or career, right, if you can get a couple people that level you up, and a couple people below you. So you can help them level up like people that you trust people who are willing to be vulnerable and pretend that they’re, you know, not always crushing it. That’s been super helpful to me, right? You can read all the stuff in the books in the conferences, but it’s the real time examples, getting different opinions of how to tackle them, to me is probably the biggest difference in in my seven years.

Well, our friends over at a equal Richard and Rick have have done a lot there. And that’s been super helpful. Yep, that’s right. David, what do you know, you need to get better at?

I think I’m still trying to figure out time management and like, you wear so many hats as an investor and especially as someone who owns and runs a firm, right? Like, I probably only spend 20% of my time like looking at new investments, right? And people think that’s all I do. Like I’m on Shark Tank and just sit there getting pitched and putting my thumb up or down. There’s so many different aspects now that I sit on a bunch of boards, have a bunch of founders that I need to help have Junior employees that I need to manage and coach and mentor. I need to go fundraise. I need to go network I need to do research and get smarter on spaces. I need to do stuff like this and build up my brand. And figuring out not only like how to spend my time, but tracking ROI, so I’m continually optimizing My time is not easy.

And finally, you know, what’s the best way for listeners to connect with you and follow along with what you’re doing at alpaca? Yeah, I

guess one just like, find us on all our social channels. You know, with our new brand alpaca, we’ve tried to had a little fun with it. We’re on Instagram, we’re on Twitter, you can email me directly at David alpaca.vc. And the advice I give if you are sending a pitch or even want to connect for anything, like, be pretty specific on why you’re reaching out to me specifically, why am I the right person to talk to? And why are you probably the right person to be building what you’re building?

Love it. If you love okrs reach out to David Goldberg at alpaca. David, this is a real pleasure. It’s a it’s great to connect and appreciate the insights today. Great. Thanks

for having me, Nick. This is fun.