TechTalk: The Golden VC Firm: Unlocking Deal Flow with Key Differentiator

Pablo Casilimas:

Thank you for having me, Fritz. Excited for the conversation.

Fritz Spencer:

Always a pleasure. To get us started, I would love if you could quickly give us a brief background on yourself.

Pablo Casilimas:

Sure. Yeah. I don't know how far back you want me to go, but I was born and raised in Miami. Ended up going up to University of Florida and over there caught the entrepreneurial bug, started my first company, which was a marketing agency. Then I realized there was a lot of engineering talent at University of Florida, but there wasn't anybody teaching people how to build startups, or how to raise capital. And so I got really inspired and started hosting these meetups to help connect people in the community. That turned into workshops, which turned into round tables, and eventually a formal accelerator program. After helping 40 companies raise over $13 million and one of them got acquired within a two-year span. After the pandemic hit, we decided to launch our own fund, and we had our first close about two and a half years ago. We've now invested our first 2.7 million and we have 13 portfolio companies so far. So that is in a nutshell how I got to where I am today and a little bit about OneSixOne Ventures, but happy to go further.

Fritz Spencer:

Yeah, I love it. No, I love it. Gave us the quick and dirty rundown and OneSixOne, obviously, that's what we're here to talk about. I'd love to hear more about the history of it. What does it mean? Who's working on it with you? Tell us more about some of the dynamics.

Pablo Casilimas:

Yeah, absolutely. So the name actually comes from the Fibonacci Sequence, so it's the golden ratio, which is 1.61. And naturalists say it's the most efficient ratio for growth to occur. It actually occurs in nature. So plants, animals, even humans, the ratios of how long our limbs are to how tall we are, it's all the Fibonacci Sequence and we wanted to create a community for startups to grow as efficiently as possible. So that's where the name comes from. . And so we're OneSixOne. As far as OneSixOne the firm, we initially, again, started back in 2017 hosting meetups. And in those days, it was a couple of months after I had met who was my co-founder, Justis Mendez at University of Florida, and we both saw the same opportunity. So actually I was already hosting these little mastermind sessions with some of the smartest engineers and founders in my network, and he was doing the same thing. And so when we met, we actually combined efforts. Well, there was a pivotal moment that led us to combine efforts and start hosting these events, it's a little bit of a longer story, but happy to go into detail on that if you'd like. But yeah, it was February of 2017 that we hosted our first event. And back in those days it was literally a bunch of college kids in a backyard talking about ideas and startups. And we had our mentor, Martin Schaffel, who had also come out. He was a professor at UF. And then it just grew and grew and grew. And about a year and a half later, we started getting city commissioners coming out, one of the largest real estate developers in town. And any investors that were in town would come out to our events and they became the most popular startup events in the north central Florida region. So that was how we got started. And there was a couple of others involved. Back in those days, we never had any intention of starting a fund. In fact, in those days we knew very little about venture capital. But that sort of progressed and came about later on.

Fritz Spencer:

I love how you talk about it from the nature standpoint, the Fibonacci Sequence and how it ties into everything and  the seedling of OneSixOne and where that started. Tell us a little bit more about where you guys are today. I've seen you guys are getting a lot of press, you're investing into different sectors all within the technology space, but tell me a little bit more about how it's evolved and where you're kind of taking the fund.

Pablo Casilimas:

Yeah, absolutely. So we invest in pre-seed and seed enterprise software, government tech, and we're really interested in infrastructure for AI and cloud. So as I mentioned, we've invested about 2.7 million, we have 13 portfolio companies total, and happy to go into detail about some of these companies. But the other thing that I'll mention is one of our core differentiators as a firm is our ability to host highly curated programs and events. So going back to our roots of how we started just doing these little meetups in a backyard in Gainesville, now we're hosting summits, we're hosting tech weeks, we're hosting massive events from Miami to Gainesville to Seattle, Cleveland, New York. And really what's come of it is these events serve as a platform to be able to help connect founders with investors, potential customers, give them an opportunity to pitch and get exposure, but also it brings us deal flow because the founders are coming to our events because they want to learn and connect, and we're getting the opportunity to build a relationship with them. So we're getting deal flow through it. We're also establishing a brand and a reputation. So our events are building a little bit of a reputation for bringing in high quality speakers and having good people in the room. And so in Seattle, for example, in the past 12 months, we've actually hosted five sold out events. On average, about a hundred people come out. And we've had some incredible speakers including the global director of generative AI at Accenture. We had the director of AI strategy at Oracle Net Suite, the AI chief technologist at Boeing. We've brought in some pretty remarkable entrepreneurs and tech leaders, and again, we're meeting some great founders through this. And then just to go into quick detail about some of the portfolio companies, so maybe I'll touch on some of the recent ones. So this year we've made two investments and we're going to be closing on our third one pretty soon. So the two that we've made so far, one of them is called Rain AI. And what's so cool about Rain AI is that this is a very full circle moment for us because we were really good friends with the co-founders, Jack Kendall and Gordon Wilson back at University of Florida during our undergrad. And when they left to go through Y Combinator back in 2018, this was one of the key drivers and motivators for what we were doing with the workshops and the round tables. Because we realized these are geniuses, these kids were so smart, and if we had any money back then, we would've definitely given them a check, but we had no capital back then. And so we said we got to keep building this ecosystem because otherwise we're going to keep losing the best entrepreneurs and the best engineers that we have here. Fast-forward to about late last year, we caught up with them. We would catch up usually once a year, and we caught up in December, and they had  this article come out about how Sam Altman was an investor, which we already knew about. But then more importantly, that OpenAI signed a letter of intent to purchase $51 million worth of chips from this company. And Rain AI, their whole mission is to build the most energy efficient chips for AI on the planet. And so at that point, we realized this opportunity was too big for us to not participate, especially given that it is so tied to the origin story of OneSixOne. And so this was a series A extension round. We tend to only do pre-seed and seed, but in this particular case, what's interesting about Rain AI is that even though the valuation was a lot higher and it was a series A extension, they're actually a similar stage in a way to a lot of the companies that we tend to invest in. So pre-product or maybe just post-product, pre-revenue, still pretty early, right? They're going to launch their first chip in a couple of months, but the valuation is a lot higher because they have some very strong IP and they obviously have Sam Altman on the cap table as well as a lot of other very impressive angels. That was our first investment of the year. We closed in February and were very, very optimistic about what the team is doing. They're getting some very notable traction because this year they started licensing some of their IP and they're getting some really good traction with some enterprises. And then the other one that we invested in is actually a Seattle-based company, which again, going back to the events that we're hosting, it's really been helpful for us connecting with other VCs that can share deal flow as well as great founders here. So this one is called Hedgehog and it's an open networking fabric for data centers. The founders are former Cisco executives. One of them actually built and sold a company called Insieme Networks, sold to Cisco for $863 million in less than two years after being founded. So the founders are pretty sharp, and have a great track record. Both of them have had multiple exits. And this deal was sent to us by a guy named Kirby Winfield here. He's one of the most well-known early-stage VCs. He's actually the most active pre-seed investor in the Pacific Northwest and he has built four companies. Two of them had IPOs and two of them were acquired. He's got an incredible track record and  areally great person overall. He sent us the deal, and so I was thinking we got to take a look at this. This is a very great source to receive a deal from. This was obviously very technical, Justis and I are not technical, so we actually brought in the former CIO at T-Mobile to help us vet this deal. And that's somebody that we met through the ecosystem here in Seattle actually. And then we also brought in a good mentor of ours named Marvin Wheeler. He was the COO at Teramark, which sold to Verizon for $2.3 billion. So we had the two of them on a call for an hour long with the founder and CEO of this company. And they're just grilling him. They're going deep technically, and about 15 minutes in, they're like, "He has a technical side down for sure," and then 30 minutes in the former CIO of T-Mobile says, "Can I invest? Is there more allocation?"

Pablo Casilimas:

so at that point we realized that they were on something pretty big and we talked to a lot of other people and what they were building is something that a lot of people are trying to solve for, but this just turns out to be a really good team to build this. So we invested in Hedgehog that closed in April, and now they're getting some really notable traction. They're already raising a seed at a significantly higher valuation. They're close to closing some enterprise deals that are pretty large, and they have some good traction on their seed raise so far. So those are the two that we've done this year.

Fritz Spencer:

Awesome. Thanks so much for those details. That's really interesting to hear about what you guys are actively investing in. And obviously the biggest buzzword right now is AI, so I'm glad to hear that you guys are investing in it, but investing in a way that's informed. I'd love to know more about how you feel about the advancement of AI and what it really means to you. Because now that it's blown up, it's become more of a buzzword and there's so much fluff around it now and it's really hard to understand what it really is and what it actually looks like. Is that something you could share with us?

Pablo Casilimas:

I do think that we're pretty early on. In a way, it's like the early days of the dot.com boom where you had all these internet startups. And in those days, I can imagine it was very hard to tell who was going to be different, right? Google was the 11th search engine, if that's what I recall seeing. Amazon was not the first to market selling stuff online. So it was a crazy time with people building all these applications. And I think now we're seeing that with AI. And so what we're using as a guideline or as a compass to differentiate and sort through and filter is I believe that founder market fit is more important than ever before. Just a couple of weeks ago at our enterprise AI day event that we had here in Seattle, we had Yuval Neeman speaking, he's a managing director at Trilogy Equity Partners. He said this directly, he said, "Domain expertise is more important than ever before." Because now it's like that quote that you have from The Incredibles where the villain is like, "When we give everybody superpowers, then nobody will be super, right?" So everybody has access to AI, so the technology, and everybody can build stuff with it, but what is the core differentiator? What can you do on top of that? So that comes down to domain expertise and quality of data. So those are, I think two of the most important things. So is there a unique differentiator in the team? And then do you have some type of unique data set that you can train your model on or a unique data set that you can do things with your AI applications that others cannot do? So these are some of the things that we're seeing. And then the last piece is, for example, AI applications, there's so many of them and it's so hard to sort through which one is going to be the winner, and they have teams that are incredibly smart on both sides. But with AI infrastructure, there's obviously a need for it. It's not a question of whether this is going to be a thing, it is a question of which one is going to be the best one. But I think there's less competition there because more people are focused on the sexy things and the glamorous AI applications. So I think there's less to sort through. And at that point, you could just filter by IP, by team, founder market fit, these types of things. So the Rain AI and the Hedgehog are both examples for us of AI cloud infrastructure that we've backed this year, and we believe there's something different about the team and we believe there's something different about the technology that they've built so far.

Fritz Spencer:

Yeah, I love that analogy about The Incredibles too, everyone has the superpowers, everyone has access to AI now, and they just have no idea how to use it. So they're just throwing it into everything. So weeding out what makes sense to you guys, seems like you mentioned your compass is really set to a true north there. I love to hear that. And to close us off, I'd love to know, you mentioned a lot about the community and culture that you grow around your business, not only for deal flow, but for also the local communities that you guys are in. You're in Seattle now, you're based out of Miami, Justis is in Cleveland, so you're doing things everywhere. Tell me a little bit more about the events that you guys are hosting and love to hear about what's coming up soon.

Pablo Casilimas:

So as far as events coming up, we actually have the Gainesville Innovation Summit happening on October 18th, which is the day before the homecoming game at University of Florida. So this is an opportunity to bring in a bunch of alumni to speak, mentor student entrepreneurs, and then also come and have a great time, go to the Gator Growl, a homecoming concert, go to the homecoming game, and just be around a lot of great alumni and great energy. So the innovation summit is going to feature several keynote panels. We're going to have some pitches. It's a full-day event, and then we'll also have a VIP event afterward for the speakers, sponsors, and VIPs. So yeah, super excited about that one. We're going to be hosting another big event in December in Miami during Art Basel or Tech Basel as we're calling it now. So that one is still TBD, so we'll keep you posted on the details. We'll be sharing that on LinkedIn once we have more. And then the last thing is our Starved Lunch competition, which we do every fall at the University of Florida. We're teaching students every single week through the business college how to build an MVP, how to talk to users, how to ramp up those first 100 customers or users, how to put together a pitch deck, raise capital, all these things. So that's ongoing throughout the fall, and we're going to finish that up the first week of December as well. And then right after Tech Basel, we come back to Gainesville and we host the actual demo day event. So we'll be bringing in several angel investors, and VCs to be judges for that, and then we're going to give a big cash prize to the winners there. So those are two that we have coming up. And yeah, I think the best thing to do is connect with us on LinkedIn or Instagram because we're constantly posting any of the events that we're doing. And now and then we will spontaneously say, "Hey, we're hosting an event here, and it's a week away, two weeks away," so you definitely want to stay up to date with what we got.

Fritz Spencer:

Awesome. You know I definitely will. I want to be there. So I'm going to make sure that me and my colleagues are in attendance at the next OneSixOne event 'cause we know it's always a good time. Well, listen, Pablo, I want to thank you so much for joining me to have this conversation today. It was an absolute pleasure.

Pablo Casilimas:

Thank you so much for having me, Fritz. Appreciate you.

Fritz Spencer:

Of course, man. Of course. And thanks again to our listeners for tuning into TechTalk, the entrepreneurs and innovators who turn to EisnerAmper for accounting, tax, and advisory solutions to help propel their success. Subscribe to EisnerAmper podcast, to listen to more TechTalk episodes, or visit eisneramper.com for more tech news that you can use.

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