Pablo Casilimas, co-founder and managing partner of One Six One Ventures, joins Vlad Cazacu, co-founder and CEO of Flowlie, to discuss his unconventional journey from an engineering student, through content marketing and event organizing, to founding 161 Ventures alongside a close friend.
Pablo Casilimas, co-founder and managing partner of One Six One Ventures, joins Vlad Cazacu, co-founder and CEO of Flowlie, to discuss his unconventional journey from an engineering student, through content marketing and event organizing, to founding 161 Ventures alongside a close friend. We cover strategies for sourcing and funding startups, the significance of founder-market fit, and insights into maintaining a venture fund's integrity by wisely managing GP entity ownership.
00:00 Welcome to VC Architects: Unveiling the Blueprint of 161 Ventures
01:06 The Genesis of 161 Ventures: From Engineering to Entrepreneurship
01:56 The Evolution of Gainesville's Startup Ecosystem
03:19 Pivoting from Engineering to Content Marketing: A Founder's Journey
06:32 Leveraging Events for Growth and Networking
09:06 The Birth of 161 Ventures: From Accelerator to Venture Fund
11:49 Securing the First Investors: Turning Vision into Reality
17:29 Navigating the Venture Fund Landscape: Insights and Strategies
20:36 The Art of Attracting Dual-Use GovTech Startups
21:55 Decoding Success in Enterprise Tech and GovTech
28:09 Lessons Learned and the Path Forward for Emerging Fund Managers
41:35 Gratitude and Reflections: The People Behind the Journey
You can find Pablo Casilimas on LinkedIn at https://www.linkedin.com/in/pablo-casilimas-1707a9113/ and on Twitter at https://twitter.com/pablo_casilimas and learn more about OneSixOne Ventures at https://www.onesixone.ventures/.
Learn more about Flowlie and how the platform can help you screen deals faster and discover the right connections from your network at https://www.flowlie.com.
Stay up-to-date with all our episodes by checking our website at https://www.thevcarchitects.com, following us on Twitter at https://twitter.com/thevcarchitects, and on Instagram at https://www.instagram.com/thevcarchitects.
The VC Architetcs (Ep. 11) - Pablo Casilimas (OneSixOne Ventures)
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Pablo Casilimas: [00:00:00] Hi, I'm Pablo Casilimas, the co founder and managing partner of 161 Ventures. We're a Florida based pre seed venture capital firm focused on enterprise software and government tech startups.
Vlad Cazacu: Hey everyone, thanks for tuning in and welcome to the VC Architects, the podcast where we share the real stories behind new VC fund managers and the blueprints used to make them successful. My name is Vlad Cazacu and I'll be your host today as we interview Pablo Casilimas and listen to his story from an engineering student who pivoted into content marketing To eventually start an accelerator before raising his first fund alongside a dear friend.
Vlad Cazacu: This is such a unique story with a person who followed his passion and didn't let anything stand in the way of him making an impact. For more information about starting and growing your venture fund, including show notes, highlight clips, and exclusive scenes, follow us on Twitter and Instagram at @TheVCArchitects, as well as on our website at thevcarchitects.com. This episode is brought to you by Flowlie, the number one fundraising and financing hub for [00:01:00] early stage founders using over 50 countries around the world. Now let's dive
Vlad Cazacu: right in.
Vlad Cazacu: Pablo, such a pleasure to have you on the podcast. Thank you so much for joining us.
Pablo Casilimas: Thank you so much for having me. I'm excited for this.
Vlad Cazacu: Man, it's been an exciting friendship so far. And I remember last time we had an engagement, a speaking engagement together, I was actually there in Gainesville with you guys at your last conference. This was an exciting, exciting time. And really appreciate everything that you're doing for the entrepreneurial ecosystem there. Really excited to have you on the podcast today.
Pablo Casilimas: Absolutely. Yeah. That was Gainesville tech week back in February. Now we're planning our next big event in October. And, but yeah, excited to be on here and chat more about it.
Vlad Cazacu: I think a lot of people are going to benefit from learning a little bit more about your background, 161 ventures and what you're really doing in Gainesville. Because I'm not even sure, I mean, I'll, I'll, I'll speak personally, a lot of people knew of Gainesville and the entrepreneurs scene there before meeting you or interacting with one of your programs.
Vlad Cazacu: So I'd actually like to start there, right? You've been [00:02:00] in Gainesville for quite a period of time, from your UF days. Tell us a little bit more about your journey into Gainesville, a little bit of the entrepreneurial magic that you've seen happen there over the past decade.
Pablo Casilimas: Yeah, absolutely. So I started at university of Florida back in 2013 and lived there for most of the past decade.
Pablo Casilimas: And what I have seen has been absolutely incredible. It started in the beginning when I, when I first got into the entrepreneurship world during my freshman, sophomore year, there was a big company at the time, big startup that was generating a lot of buzz called the group shark. It was kind of like a sound cloud or Spotify is today. And ultimately that company ended up going under. But that led a movement in Gainesville and the startup ecosystem just started to take off. So once Grooveshark went under a lot of the former leadership engineers spun off other startups out of there. And there's been quite a bit of activity there.
Pablo Casilimas: The thing that we saw that was [00:03:00] missing was capital. And we kept hearing this, you know, when I was a student, when I was starting my first company, uh, there's no capital here. If you want to start a startup, you got to go to Silicon Valley or you got to go to New York. Um, and you know, it's, it's really excited to come full circle and now be investing in startups in Gainesville through our venture fund.
Vlad Cazacu: Absolutely. And before we get to your investing career, I want to spend a little bit of time on your entrepreneurial career. Because while you were in college and afterwards as well, you started your own content marketing agency, Rutex.
Vlad Cazacu: So I'm curious what prompted that decision, because if I remember correctly, you were an engineer at that time and decided to make a Full pivot into advertising and entrepreneurship. So walk us a little bit for that decision and how it evolved over the years.
Pablo Casilimas: Yeah. So it actually starts when I was a kid.
Pablo Casilimas: So when I was a kid, I was always fascinated by entrepreneurship, startups, innovation. But the reality is that both my parents are immigrants and they really cared about security. And so growing up, my parents [00:04:00] always told me there's only three real careers. You got to be a doctor, a lawyer, or an engineer.
Pablo Casilimas: And so even though I was fascinated with business and entrepreneurship, that didn't seem like a viable option. And, and so. I hated reading and writing, so I wasn't going to be a lawyer. I couldn't stand being in a hospital or the sight of blood, so I wasn't going to be a doctor. So I said, all right, I've always been pretty good at math and science, so I'll be an engineer. And two years into my college career, I got my first internship with a fortune 50 company called Pratt & Whitney. And. They make jet engines for commercial and military jets.
Pablo Casilimas: And just about one month into that, I was miserable. I said, I don't want to do this. I don't want to be an engineer. I don't want to work nine to five and I don't want to work for a corporation. And I immediately started thinking, I realized I'm at a crossroads. I'm halfway through my college career, but I'm about to start over. And so why not just go after. What I've wanted to do my whole life, which is start a company or innovate something.
Pablo Casilimas: And so I started a content marketing [00:05:00] agency, root techs, because I thought back, okay, people always said you have to love what you do, right? That's the only way to do great work. You know, Steve jobs said that. And for me, I realized. Growing up. I always loved when I, whenever I was assigned a video project in high school or even in college, I would always go above and beyond because I was having so much fun with it.
Pablo Casilimas: The other thing that I wanted to do was pick a field that would have value no matter what, even if I failed, I would have a valuable skillset or it would allow me to build a network and I realized every company needs marketing. It doesn't matter who you are. Everybody could benefit from having content, whether it's internal or external.
Pablo Casilimas: So I said, all right, this is the path. And I think the best thing that I did was just, I jumped off the cliff immediately. I said, let's, let's go, let's do it. So I bought a camera, I created a company name and website, everything and started doing work. So it was really, you know, going back to my roots, it was, it was in my, in my DNA, I always wanted to get into entrepreneurship and business, but it wasn't until I had that pivotal moment where I [00:06:00] realized, whoa, I'm not going to be an engineer for the rest of my life that I had the courage to really go after it. And that's why I chose to start that marketing agency, which was a pivotal moment in my life.
Vlad Cazacu: And I'm curious to hear, because you mentioned how getting the skillset that will always be helpful right now, looking you as an investor and startup supporter and helping your portfolio companies, are you still leveraging a lot of the work and the network and the skillset from the content marketing agency nowadays in your day to day work or
Pablo Casilimas: not?
Pablo Casilimas: Somewhat. So, What ended up happening after we started the, after I started the marketing agency is I obviously struggled like any other business, how do I get clients? And that led me down this other path of hosting events. I realized if I could attend events, I could meet a lot of people by networking.
Pablo Casilimas: But if you host your own events, that's like a networking hack because then people come to your event and they want to get to know you. Right. Similar to like what you're doing with a podcast, like people, you're doing the podcast. People want to be on your show. And [00:07:00] so I started doing these events and I teamed up with, uh, my now co founder and co founding partner at one six one ventures, Justis, and a couple of other friends that had startups at the time. And this is back in 2017, early 2017, we started hosting meetups for founders, for business leaders, and these events just took off. They three years later. Most popular events for startup founders every single month in the North Central Florida region.
Pablo Casilimas: And, and then COVID hit, which made us have to pivot, but fast forwarding to now, events is a core part of everything that we do at one six one, because it allows us to put our portfolio companies on a platform. So we've gotten really good at doing highly curated quality events, That have an impressive lineup of business leaders, executives, partners at firms.
Pablo Casilimas: And if we can put together a rockstar lineup and then have some of our portfolio companies come on the stage and present their startups, [00:08:00] that could lead to potential partnerships. I could lead to new investors. I could lead to new contracts, whatever it is. And so that's exactly what we're doing now at one 61 ventures.
Pablo Casilimas: This year alone, we've done four high quality events. Not just in Florida, we did a Gainesville tech week, which you spoke at and you're familiar with, but we also did a startup bootcamp in Cleveland. Uh, and then this summer we did two big events in Seattle, Seattle venture day hosted at Madrona and Seattle angel investor round table.
Pablo Casilimas: And at those two events, even Seattle, like opposite side of the country, we had two portfolio companies present at each one of those events. So a total of four different portfolio companies got to present. One of them already closed a new investor from presenting there. One of them just got like six introductions by one of, uh, a very, uh, Widely recognized, uh, community ecosystem leader in Seattle.
Pablo Casilimas: So they're benefiting from these opportunities. And so it's one of those things that you don't think about at the time, but hosting events is how we [00:09:00] started. And it was such a valuable skillset that now we leverage quite a bit. Now that we have a venture fund.
Vlad Cazacu: Fantastic. And at what point in that journey did you go from events and community building to a fund? At what point did one six one ventures really came to be as an entity, but also as an idea in your heads about, no, like we should invest in companies?
Pablo Casilimas: It all started right after COVID hit. When COVID hit, it was kind of like the rug was pulled out from underneath us. We, we were like, well, all we've done for the past three and a half years is events and there was such a need for it and there were such high quality events. How can we continue to support startup founders? And we said, all right, well, we had a five year goal of launching an accelerator, why don't we just launch it now virtually, and so 10 weeks later we did. And that was June of 2020.
Pablo Casilimas: And, you know, we still weren't thinking about launching a fund. We were just thinking, how can we add value to startup founders? Actually, we didn't think that was even a realistic possibility [00:10:00] of launching a fund. We said, maybe 10 to 15 years from now, we'll launch a fund. And about less than two years later, we had helped 40 companies raise over 13 million, did it all for free through our virtual program.
Pablo Casilimas: As we were helping these companies and connecting them to venture capital firms, we were asking the firms, Hey, can you give us a finder's fee or a scout fee? And the majority of them actually said no. And so at that point it was almost out of like anger and. The seed was planted in our head at that, at that moment.
Pablo Casilimas: You know, this is like actually this is only about seven, eight months into launching our accelerator because we had already done two cohorts and we had gotten some really interesting opportunities through those cohorts. And we had sourced some really good deals. And so the seed was planted at that point, but obviously we were not ready to raise a fund.
Pablo Casilimas: And so, About six months later, we did it. We spent a lot of time doing reading, watching [00:11:00] videos, learning everything that we could, and about six months later, we said, all right, let's the only way we're ever going to be able to do this is if we start just like we did with our accelerator. And so this is probably the beginning of summer of 2021 when we officially started pitching.
Pablo Casilimas: And in those days we said, Let's pitch anybody and everybody who's, who will take a meeting with us. It's all we could do. And it was also helping us refine our pitch and get the messaging right. And, and also all while we were doing that, we were also making progress with our accelerator, right? Getting more deals, the deals that we previously sourced were progressing and growing and doing a lot better.
Pablo Casilimas: And that was really how he started, but the seed was planted in January of 2021, just seven months after launching our accelerator.
Vlad Cazacu: And I'm very curious, who was the first person to say yes? Because you're coming out of this event into an accelerator, into a fund trajectory with some [00:12:00] Really high quality startups in your, uh, kind of near sphere, with high quality people behind the fund. Someone at some point had to say, yes, I agree with everything that you said, here's my money and let's make this a reality.
Pablo Casilimas: So the truth is that because we've been doing events for so long. And the other thing is that the opportunity that we saw, we weren't the only ones who saw it, any business leader in Gainesville or any founder that built a successful company in Gainesville, saw the same opportunity that we saw. It's just, nobody had ever done anything about it, right? Most of the sharpest founders and engineers would just leave Gainesville and go start their own companies elsewhere. And we were the first that said, okay, we're going to stay here and we're going to build the ecosystem because there's an opportunity here.
Pablo Casilimas: And so the first yes, or first couple of yeses that we got, it didn't take a lot of meetings, actually. It was people that as soon as we brought it up, they said yes immediately because [00:13:00] they knew us already through the ecosystem and they saw the opportunity that we saw. The first two was Two of our mentors in the ecosystem. So Paul Prusikowski co founded the largest software company for prosthetics and orthotics clinics in the country and based in Gainesville, right? Uh, and then the other one was a co founder of a company called Infinite Energy, which was the largest natural gas retailer and supplier in Florida. And they scaled the company to 600 million a year in revenue. And then They just sold it two years ago. So these are two individuals that knew us through the community because of the events that we've been hosting. They had mentored us. They've been involved in some of the things that we were doing, whether it was speaking at an event or collaborating on an event.
Pablo Casilimas: And so those were easy. Yes, is for them. The first game changing yes, which came from somebody that we didn't know, that was not part of our immediate network, and it was our first substantial check, came probably about I would [00:14:00] say five months after we started fundraising. And that was a founding partner at a venture fund based in Tampa.
Pablo Casilimas: The way we approached that or the way we got connected there was we were connected by another founding partner at another venture fund. The firm is Tampa Bay Ventures. I had met one of the other partners at Tampa Bay Ventures through clubhouse. So back in the clubhouse days, I was very active connecting with people on there all the time.
Pablo Casilimas: And then we got that partner into our accelerator demo days. He was seeing what we were doing and the deal flow we were generating. And so, you know, we had two really credible sources pushing this, this one person. And. Yeah, it took, uh, it was again, this was actually just one meeting. He actually flew to Gainesville on his plane, met with us. We sat down for lunch, 10 minutes into lunch. He said, all right, I'm in. And he said, I'll start with a quarter million and, you know, and then the rest is history. So that was, that was the moment where it became real. That was the moment where we were like. Wow. [00:15:00] Like we have a venture fund, like we could actually do something here.
Vlad Cazacu: Fantastic. Out of that period between the very first yes and the first kind of outside of the network check, were there ever a period where you were doubting if this venture fund is really going to happen? If you made kind of the wrong choice, deciding to go the venture route and maybe acceleration was a better path.
Pablo Casilimas: So I, I think it's just such a difficult journey that. I think doubt is just, it's like one of those things that just, it comes up every now and then it's just like, we're all human, right? Some days you don't sleep enough and some days you're having a bad day. And sometimes doubt creeps into your mind on those days.
Pablo Casilimas: Right. And that's just normal, but you know, we saw the longterm and I think the biggest thing is that my partner, my co founder Justis and I, We both were used to hearing that we both, you know, we came from very untraditional backgrounds, we didn't have mentors, we didn't have a foundation for [00:16:00] this is how you start a company.
Pablo Casilimas: And we'd both just try it and figured it out on our own. Right. And so I think because we were used to dealing with the adversity, we knew that it would be difficult and it ended up being more difficult, way more difficult than we thought it would be. But we never got to a point where we said, should we quit? I think what kept us going was we were doing a lot of work aside from the fundraising. Cause there's two things, you know, venture firms are doing a lot of things, right? So like you're sourcing the deals and then you're also raising capital. And so for us, what really kept us going is that we had the accelerator and the accelerator continued to get quality companies.
Pablo Casilimas: You know, we had a company that in those first two years ended up getting acquired just less than a year after going through our program. Uh, we had one company that when they were going through our accelerator, They were doing less than 10, 000 a month in revenue and the revenue kept climbing every single month.[00:17:00]
Pablo Casilimas: I mean, last month they did over 15 million in revenue and we just kept seeing this and we're, and we, it just, you know, in the back of our heads, we were both thinking like, if we quit, We're gonna keep sending all these high quality deals to other firms. We're gonna keep making these rich guys richer and doing all this free work.
Pablo Casilimas: Like we have to find a way to get into these deals. And I think because we kept seeing the opportunity there, that kept us going.
Vlad Cazacu: Fantastic. And now you have a fund, right? Like you have the first LPs, you have the foundation for the fund and you're thinking, okay, what's going to be our complete thesis, our portfolio allocation, what's exactly the target of the fund. Were all of these things decided before you started the very first dollar or were those things that you discovered on the way, uh, as you were pitching LPs and you were perfecting kind of the strategy behind what one six, one ventures end up [00:18:00] becoming to be?
Pablo Casilimas: The blessing for us is that we started with the accelerator. So in a way it was almost as if we were running a venture fund for two years before we ever actually had a venture fund, because we got to learn a lot of things about what founder profiles tended to work or what founder profiles we were interested in working with. We found things like, what are the companies that don't end up going anywhere? What are the commonalities there? What are the commonalities on the breakthrough companies?
Pablo Casilimas: so for us, we actually had refined most of our thesis and focus before we had that first close, but, I mean, I would imagine like every other venture fund, especially in the early days, you continue to refine, you continue to learn, you never want to stop learning and growing.
Pablo Casilimas: It's been about a year and a half since we had that first close and obviously there's been so much more data that we've had with companies that have pitched us, working with our, our initial portfolio companies and so we continue to [00:19:00] refine, but when we were starting, we did have interest in both enterprise software and government tech. We just didn't really know how to communicate it as well as we do now. The way we Say our fund focuses on this particular sector. In those early days, it was like, this is what we were interested in, but we didn't have a super clear way to communicate that, I think that was the biggest difference.
Pablo Casilimas: And then I think the other thing is that when we were running the accelerator, what was interesting is that we saw that we didn't know anything about government tech, right? This is, it's a space that a lot of VCs don't touch. And a lot of VCs are not interested in and stay away from actually, but we actually had a lot of companies that went through our program that were in the government tech space. And what we noticed as we were getting ready to have that first close is that the market started to pull This is like February of 2022. So market started to come down and About three years ago, anybody who had an enterprise software company could raise money with a blindfold on, they could [00:20:00] close deals with a blindfold on. All these companies were scaling and everything was working right. All of a sudden things started to pull back and it no longer was that easy. But what we realized at that time is that selling to government is in a way a hedge. Versus the companies that are only selling to enterprise. And then the other thing is companies that are dual use tech, which is what we're really focused on, they just have a larger TAM and then they're more recession proof as well and so that's really what we're focused on now is the dual use technology, startups, companies that can sell to both enterprise and government.
Vlad Cazacu: And how are you attracting these types of companies? I mean, it's a very specific subset of venture and there's as much marketing that you can do of like, we are the dual use GovTech investor.
Vlad Cazacu: So I'm curious from your strategy of the fund, what worked the best on attracting the type of company that you were looking to attract in order to make investments?
Pablo Casilimas: That's a [00:21:00] great question. And it's not something that happens overnight. I think that we have put it out there that this is what we are focused on investing in.
Pablo Casilimas: And so we get a lot of inbound, but there's only so much quality you're going to get through only getting inbound as your deal flow strategy. And so we attend tons of events. We're constantly getting out there and meeting people, networking, meeting other VCs. The cool thing is that because most VCs don't touch government tech, when we tell them that we do, they immediately, they always remember that.
Pablo Casilimas: And they sometimes already have deals off the top of their head that they want to connect us to. The other thing is we host a lot of events and by hosting events, it gives us an opportunity to get in front of a lot of people and let them know, this is what we're focused on. This is what's different about our firm. This is how we do things. And that ultimately leads to us getting deal flow.
Vlad Cazacu: And you mentioned a few minutes back around getting more data points now [00:22:00] that you've been in the fund for a little bit about, you know, what works and what doesn't, I'm curious because the audience of this podcast is both emerging managers, VCs, but also founders.
Vlad Cazacu: Let's take a second to discuss a little bit what works in enterprise tech, dual use and GovTech. In terms of the company that you've seen have that breakout moment. What was the commonality there?
Pablo Casilimas: Absolutely. I think a lot of the things that we see here are actually very similar to just any successful founder profile, right?
Pablo Casilimas: I think there needs to be a, some type of passion or attachment or founder market fit there. Usually it'd be very odd to have a founder who's never been in the GovTech space saying, Hey, I want to build this product for police departments with no connection to police. And so there usually needs to be some type of connection there.
Pablo Casilimas: To give you an example, our first portfolio company is EaseAlert. They actually went through our [00:23:00] first accelerator cohort about three and a half years ago, and we saw them continue to progress. But what EaseAlert does is they created a wearable device that gives a gentle pre alert before the alarms go off at the fire station for firefighters.
Pablo Casilimas: And Blake's father was in the fire service for over a decade, and he, his dad would always come home stressed. And he asked, he started doing research, and he found that the leading cause of death in the line of duty for firefighters, Is actually a heart attack and firefighters are actually 14 times more likely to have a heart attack when the alarms are going off at the station.
Pablo Casilimas: And so this is a key insight that you wouldn't be able to, you wouldn't know this if you didn't have some type of connection to it. Right. And his whole mission is to help reduce the rate of heart attacks on duty in the fire service and give more years to our heroes that are helping save lives. And the other things that we look for or that most firms look for in founders, regardless of industry, we are very interested in [00:24:00] funding companies that are led by teams that can both build and sell. So usually at least two co founders typically, uh, usually one highly technical co founder and then one with great communication skills.
Pablo Casilimas: And so those are things that we look for, which Again, I think this is applicable to just about any industry, but yeah, these are some of the things that we have started to see that are commonalities amongst the ones that end up being the breakout companies.
Vlad Cazacu: What was one thing that you wish you knew around venture investing specifically in picking and sourcing companies before you even started, not the fund, but actually the accelerator altogether?
Pablo Casilimas: Yeah, that's a great, that's a great question. I would say the biggest thing for us is in the beginning, like you oftentimes can be very, you can be drawn in to somebody who maybe has a lot of confidence and they seem like they have a [00:25:00] very clear vision and they know what they're doing, but if you dig a little deeper, there's not really found a market fit there. They're just chasing a wave per se, right? They're just chasing an opportunity to just trying to make money. Right. I think that was one of the biggest insights that we gleaned from running our accelerator for two years, two and a half years is that the founder profile that ends up at least continuing to grow and, and potentially lead a breakout company is not the one who's overconfident and has a clear vision and is taking advantage of this new wave or opportunity. It's the one who's, uh, some founder market fit, some, some connection to the industry and some key insight that maybe others don't have and is willing to spend weeks on end years on end working 80 hour work weeks, right?
Pablo Casilimas: They're, they're working their butts off because they have a mission, right? They're, they're mission driven. The other thing that [00:26:00] we learned from the accelerator days is there's a particular founder profile that at least in our experience did not work very well. And we stopped accepting these types of founders into our accelerator and we don't fund these types of founders and the profile that I'm talking about is somebody who, and this is, I have to be careful what I say here because this is not always the case for this type of person, but typically somebody who comes from a lot of Wealth, or maybe they were raised by a family who had made a lot of money and they just see starting a company as I'm going to hire somebody to do this. I'm going to hire somebody to do this. And maybe they have a lot of access to resources, but they're not willing to roll up their sleeves and get down and dirty and actually, you know, do 50 cold calls in a day and send 100 cold emails over the weekend. They want to spend 10, 000 on a marketing campaign and create buzz and be on the news and get [00:27:00] featured in the publicity.
Pablo Casilimas: They're not, they're not willing to put in the work and the crazy hours. So that was the founder profile that we saw. We had a couple of those that went through our program and the companies did never really amounted to anything because they would just hire somebody to build the product. They would hire somebody to market. We don't fund companies that are out completely outsourcing the development of their product because we want somebody who has skin in the game. We want, we want somebody building the product that is doing it for equity. They're doing it because they see the longterm promise and opportunity.
Pablo Casilimas: They're not doing it because. So you're getting paid a couple thousand dollars a month, right? And then you've got 30 other projects that you're also doing simultaneously. So it's not really a priority.
Vlad Cazacu: I'm really glad you brought that up because the alignment of incentives inside the organization and kind of that grit and hustle specifically at pre seed and seed, which are, some of the areas that you also touch are probably one of the biggest determinants of you [00:28:00] surviving for another day and then another day and then another day, and then hopefully get enough funding to and enough revenue to then scale up. So I'm glad you touched upon that. I'm curious from a operational and fundraising standpoint, coming back to right before the decision, uh, to create one six one ventures as a fund happened.
Vlad Cazacu: What would have you advised yourself or taught yourself in advance to hopefully avoid some mistakes down the road?
Pablo Casilimas: So this is something that thankfully we actually have avoided, but it did waste some of our time over the past two years, entertaining potential opportunities that really we should not have been entertaining. So one thing that I wish I would have just known from the start is. You don't want to give up any part of your GP entity in the beginning, meaning you don't want to give up ownership of your fund to anybody.[00:29:00]
Pablo Casilimas: It doesn't matter how much value they could bring in the early days. I think that that you want to treat it like gold. I mean, I'm not saying you can never give it away, but you just need to be very, very selective and careful with that because Building a firm is a very long term thing. I mean, we're talking about one fund is 10 years and some of them have been going on to 15 years, right?
Pablo Casilimas: So if you're building a firm, I mean, you're talking about 30, 40, 50 years, right? This is, this is what we're building. We're building this for the rest of our lives. And. Your GP entity, your firm equity is gold. And one thing that we have had many times has been somebody who appears to be very, very experienced and connected that has tried to convince us to give them part of that. Maybe they've agreed to invest a little bit, but get, you know, some advisory shares or whatever it [00:30:00] is. And then there's others who we actually look up to and who are incredibly accomplished individuals, in other cases that they see the opportunity and they want to work with us and they also asked us to, to be part of that GP entity to get some type of advisory shares. Right. Uh, and you know, we, we've declined all the opportunities because Justis and I have a particular vision for what we're building. And like I said, it's a very long term thing. We both were very aligned because we started doing events together seven years ago, I mean, before we ever knew we would ever be running a venture fund.
Pablo Casilimas: And we got a lot of time to be able to work together, build that relationship together and we have a very clear vision for what we're building. And we're both on the same page. And so when you think about bringing other people into that GP entity, it's It can deviate that vision, right?
Pablo Casilimas: It can make you get distracted from what you're going after and what you're pursuing. Uh, and then also you don't have that chemistry, right? If it's somebody that maybe is a mentor or maybe [00:31:00] you do have a relationship with, it's not the same type of relationship. Because you haven't spent five years getting to know them and work side by side with them.
Pablo Casilimas: And that's one of the things that we have personally avoided in our firm. We have not brought on anybody else. It's just Justis and I, but this is something that I see. There's a lot of people trying to take advantage and it's a challenge for emerging fund managers because, you know, raising that first fund is so difficult. And when you're raising, you're in a position of vulnerability because You're going to have bad days. You're going to have days where it's like, are we going to be able to pull us off? Like we haven't gotten any yeses in a while. Like, and so when you're vulnerable, somebody else can take advantage.
Pablo Casilimas: And I think it's important to always remind yourself of the long term vision and why you set out to build this because you could have, I mean, any emerging fund manager, as long as they've been able to make some progress, they'd be able to get hired at another firm because the amount of [00:32:00] work and talent it takes to raise your own fund it's incredible. I mean, it's, it's, it's a lot. So there's a reason they chose to go build
Pablo Casilimas: Always remind yourself why you chose to build your, why you chose to build your own firm and what's different about where you're headed and always keep that in the back of your head when things get tough and somebody else's offering to be the golden ladder for you and, you know, help you raise 2 million in exchange for part of your GP entity. Treat it like gold.
Vlad Cazacu: And where do you go for advice on some of these more complicated issues? Because those are not things that you just read in a book. Those are life experiences and scars that probably others have lived through and, you know, live to tell the story. So in your case specifically, who was a person that was a more like guiding post on your journey for you and justice as you were building this fund and learning about some of these nuances?
Pablo Casilimas: There's two [00:33:00] in particular, and these are individuals that we connected with early on in our journey. Well, one in particular we connected with when we were first launching the accelerator, and that was Mark Hall. He was the former head of partnerships for, uh, venture capital and startups at Google and now he's a partnerships lead at Sequoia. And so he has known about our, what we've been doing since day one. We called him before we launched that first Accelerator cohort, and we asked for advice and perspective. And he's actually personally invested in companies that have come out of our Accelerator.
Pablo Casilimas: And so he has been instrumental in helping us have that long term vision and mindset for what we're doing. And the second one is Yusuf Khan, who's actually, he was the first advisor for Zoom, and he's a partner at Ridge VC. So we connected with him maybe after we had our first close, but when we were still in that fundraising journey and we got the chance to actually meet with him in person when we were in San Francisco last year and he was advising and supporting, he was a CIO by [00:34:00] trade. He had his whole career CIO and he was advising Eric, the co founder of zoom in the early days. And. Eric one day said, Hey, we want to give you some advisory shares. And he said, no, no, I just want to help you out. Like it's not a big deal. And Eric said, no, no, take the advisory shares.
Pablo Casilimas: And so Eric kept insisting and he took the advisory shares and he said it was life changing for him. And, but what it made me realize is that there are so many people out there that have achieved remarkable things that are willing to help for free because they see the long term opportunity. They see the value in investing per se.
Pablo Casilimas: You could say investing without giving you cash, but they're giving you their time in those early days, if they can be one of the first people to help you, well, maybe 10 years from now, 20 years from now, when you're getting the best deal flow, You're going to get access to that. And so I realized that there's people like that, that we can just keep [00:35:00] leaning on and finding to support us and help us deal with those more intricate details and challenging things that comes with launching a venture fund.
Vlad Cazacu: And before we wrap it up and go to the rapid fire section, I'm really curious to ask this question, which is how do you vet those people? Because we have this dichotomy in the conversation of, you know, making sure that you don't give away things that other people may want to take advantage of you for and search for advice and a lot of people are willing to give free advice and be helpful, but there's this like gray area of like, who do you trust and who do you listen to? So how have you navigated that journey specifically over the past three years with 161 Ventures? Yeah,
Pablo Casilimas: I think it's something that comes with experience and, for us, because we came from a place where we didn't have that experience starting out, it's It's been a lot of, uh, time deliberating and thinking and trying to make the best [00:36:00] decision and a lot of intuition as well. And that is one thing that I would encourage every emerging fund manager to always stick to your intuition, because there is, again, going back to this, when you're in this vulnerable place, it's a lot easier for somebody to come in and say, Hey, we're going to help you raise all this money.
Pablo Casilimas: Give us part of your, give us part of your firm. Uh, it's a lot easier to be convinced, right? But. If you follow your intuition, oftentimes you will be able to smell something a little bit off about some of these individuals. You'll be able to hear something that doesn't feel right or doesn't sit right with you.
Pablo Casilimas: And the reality is, The people who truly have the ability to help you the most, they don't need anything from you. And so oftentimes they're willing to help again because they see the long term promise or because they just want to help somebody else because a lot of people help them in their journey.
Pablo Casilimas: And so if there's anybody who's really pushing you [00:37:00] to give them something And it seems like they're in a position of power and they're connected and they can really help you a lot. I would question that. And I would, I would, you know, follow your intuition and if it doesn't feel right, don't move forward with that.
Vlad Cazacu: I really love that. And it's specifically the one piece where you said that people who want to pay it forward and want to do it for the right reason. Most of them, they actually don't need something in return for. So use that as a proxy to also see how. How much emphasis do they put on the get versus on the give, and then, you know, take it from there.
Vlad Cazacu: Absolutely. So in the last part of the episode, we want to dig in some rapid fire questions on you personally, not just you as the 161, GP. So we usually like to start with this question, which is what is one thing that people don't usually know, or not a lot of people know about Pablo Casillimas that they should know.
Pablo Casilimas: [00:38:00] Uh, that's a good one. I'll, I'll say two quick ones. I'm a salsa dancer and I do Brazilian Jiu Jitsu. But
Vlad Cazacu: not at the
Pablo Casilimas: same time. Not at the same time. Hopefully I will never have to do them both at the same time. I
Vlad Cazacu: sure hope so. Interesting. Haven't, haven't yet found a dancer in our guest list. We'll have to invite your next event though and then we'll, you'll have to show us the skills.
Vlad Cazacu: What is one person that you've consistently looked up to over your career and why?
Pablo Casilimas: There's a person named Marty Schaffel, and he was our first mentor at once. He was actually part of the reason that we started 161 Ventures. I mean, we may not exist today if it wasn't for him. He sold his company for multi nine figures, a hundred percent shareholder. It was called AVI SPL, largest integrator distributor of audio visual equipment in the world. And. [00:39:00] He would teach at UF every year. And he still does to this day, he donated a million dollars. They don't pay him. He runs his class how he wants to, and he just wants to give back and help students be successful.
Pablo Casilimas: But he was really instrumental in our journey. He's somebody that I constantly look, I would consider him a level five leader, which I, something that I personally think is very rare. There's, I think there's very few level five leaders out there. And. I've learned so much from him.
Vlad Cazacu: What is one recent book slash article slash conversation or other piece of content that really changed a previously held belief or the way you view the world?
Pablo Casilimas: There's a video that I just saw yesterday and it's an interview with Bill Gurley. That just came out about a month ago, because he, he just moved to Austin, Texas. And for those who don't know, Bill Gurley is a founding partner or a partner was former partner at benchmark capital, top tier firm. And in that video [00:40:00] he was talking about the hype cycles and the markets and how they change and ups and downs.
Pablo Casilimas: And he lived and worked through the. com bubble through 2008, 2009, and now through the downturn that we're currently in. And he was saying that the, the true entrepreneurs and the true investors are the ones that see the longterm and They operate based on that, right? So most VC firms, VC firms in general, when they make the returns is in this Sliver of the peak of the market, right?
Pablo Casilimas: If you only do one fund, if you only do a A few deals. If you only, if you don't have a lot of time diversity, you could miss that. And if you miss that, you miss out on the majority of the returns. And so the only way to ultimately have consistent returns is to be in it for the long haul. And to be constantly in there in the [00:41:00] arena doing deals, which also is so similar to what Warren Buffett has been saying since day one to write, which very different asset class, very different minds, both brilliant, but Warren Buffett says. You got to be in the market.
Vlad Cazacu: I like that. And you got to be in the market. It's very interesting advice for an industry that's based on, you know, 10 year cycles with very long feedback loops, because you, and specifically with the distribution of returns that we have in venture It's holds more truth, uh, in this news than probably in, in any other part of investing.
Vlad Cazacu: Last, but not least who would you like to say thank you for looking back at your career and everything you've achieved so far?
Pablo Casilimas: I would say thank you to Marty Shaffel, the mentor that I mentioned. He just three weeks after being in his class, he invited me and several of my friends at the time, one of those being [00:42:00] now my co founder and partner, uh, to this very exclusive event in Tampa. These are not networking events. These are just a lot of people that built nine figure plus businesses that get together and have a good time.
Pablo Casilimas: And going to this event was a pivotal moment in my life and in our trajectory. Because if I look back that was The moment that we, that the seed was planted for one, six, one, we were on the car ride back from this event. And I was just in awe at all the people that I had met. I said, we can't pretend this didn't just happen.
Pablo Casilimas: We need to do something about this. Let's start hosting our own events. And sure enough, within less than a month, we hosted the first event of what would ultimately become one, six, one ventures. So. I'll say, I'll say thank you to Marty Schaffel. Thank you so much for all your support. What a great
Vlad Cazacu: way to end this episode.
Vlad Cazacu: My thank you goes to you, Pablo. I really appreciate your friendship over the years and thank you so much for accepting [00:43:00] our invitation to share your story and the knowledge you acquired by building 161 Venture with our audience. And do hope to have you on the podcast again in a few years to discuss 161 Ventures Fund 2 and then look back at this conversation and see, you know, all the things that we learned, ever since. Really, really much appreciated for
Pablo Casilimas: you coming here. Thank you so much, Vlad. It's been an absolute pleasure. Really enjoyed the conversation and yeah, can't wait to run it back in a couple of years.
Vlad Cazacu: What a great conversation. If you enjoyed it, make sure to like and subscribe to our podcast and be on the lookout for a new episode in two weeks featuring another amazing fund manager and their story. This podcast was made possible by Flowlie. If you're a fund manager, angel investor, family office, or syndicate lead who receives a lot of deals, or simply wants help sorting through the noise, create a free account today on Flowlie at flowlie.com, that's FLOWLIE.com, and get access to an AI assisted deal screening engine and [00:44:00] network manager that will dramatically improve how you work.
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