William Leonard
Hey everyone. Welcome back to the Atlanta Startup Podcast, your host here, William Leonard. And I am excited about the conversation that we’re going to have today with Nassir Chris, who is a principal at Sixty8 Capital. Nassir, welcome to the podcast.
Nassir Criss
Good morning. I’m excited for this. It’s been a long time coming. Well, thank you for having me.
William Leonard
Yeah, I was thinking, before we got on like this is at least a year and a half, two years in the making. And the fact that it’s happening now I think the timing is, is perfect. And I want to talk a little bit about Sixty8. Here to start, the firm is Indiana-based, and I love the thesis of Sixty8. And what you all are doing, maybe you can level set for our audience what Sixty8 Capital is doing, who your team is, and a little bit more about your thesis.
Nassir Criss
For sure, so we aim to be one of the best-performing funds, first checks into underrepresented founders. And so I think that thesis has kind of evolved a little bit over the last couple of years. It originally started as a we invest in black and brown and LGBTQ plus women founding teams. But as we’ve kind of seen some of the climate change a bit, we haven’t changed our thesis. But I think we’re telling a broader story to make sure that we’re encompassing enough kind of concerning parties that are looking at specific areas of what underrepresented means. And so I think that we’ve kind of found that that definition is fairly loose. For some people, it could be underrepresented that they live in an overlooked geography and could be underrepresented that they went to a public school instead of an Ivy League. And so all in all, like with us, in keeping with, hey, we want to propel more black and brown founders, more female founders, we said, hey, we’re investing in the bottom 5% of founders that get capital allocation on an annual basis. And when you kind of shake out the demographics of what those things are, and where those founders are, it’s typically black, brown, LGBTQ plus women, between the coasts, right, so outside of your major cities like Boston, New York, San Francisco, LA Miami, we invest with the pre-seed and seed stage. So we believe in being kind of the first institutional check into a company. We’re a little bit further along than the idea stage, per se, we’d like to see some sort of traction and a finished product that’s been tested in the market in some capacity. But we do like to come in as early as possible into those companies. We’re industry agnostic, and kind of vertical agnostic, but find ourselves these days skewing a little bit more towards direct-to-consumer and CPG, we learned some pretty valuable lessons in our fund one about how those companies work, what their unit economics should look like, what success versus failure versus plateauing. And I think some of our portfolio companies that are in those segments have done really well. So that’s kind of a quick synopsis of us and how we think about where we want to invest timing, and then the stage that we’d like to be mentioned.
William Leonard
Yeah, I’m glad you defined, you know, how you will invest at the preceding seed stage, I think it’s sort of a black box these days in terms of what PreSeed is and what Seed is, and I think is based off of where your fund is, geographically. Because a seed in the bay is different from a seed in Kansas City, Indiana, or even Atlanta. So totally understand that. And one of the things that I admire about Sixty8, as a firm is how you all operate at such a high level with a very, very lean team. So I would love to dive into, you know, firm structure a little bit and any insights that you and your team have on operating in an incredibly lean fashion, and how that may serve as a competitive advantage for you all.
Nassir Criss
Yeah, I can’t take credit for it. I think that’s something like Kelly Jones, our Managing Director and co-founder has been super intentional about over the last couple of years. I mean, when you’re operating a smaller fund, the reality is you just have fewer resources. And so we raised about a $20 million fund one. You know, some people might kind of use that all and people with personnel resources, we’ve chosen to use it in our infrastructure resources. So the thing is that supports us to be kind of the best versions of ourselves and then be able to connect our founders to the best resources. And so I think some of the advantages of it are, you know, hey, we operate on a two-person team, essentially, it’s Kelly and myself. They’re on the investment team. And then our back office is run by Julie Whitehead, who’s our CFO. She manages the back office of both Alice ventures which is our sister front of sorts, if you want to call it that, and Sixty8 capital, so she helps us with everything from capital costs to financing transactions to kind of doing our end-of-year audits and compiling financial information from our portfolio company. She’s incredible. I don’t know Oh, what we would do without her, because she’s just a phenomenon who has been a huge help. But I think having that type of structure allows us to do something that I think is a differentiator in investing, which is moving quickly and decisively like we don’t have time to kind of bicker back and forth or have a bunch of hands in the pie. Well, we decided to like something, we went fast. And that is kind of an advantage. And I think strategic alignment for us. Because when we find a company that we like, we can move from first conversation to close, you know, on average, somewhere between 30 to 45 days, so we’re not leaving founders kind of stringing along or asking tons of questions or need, we have a pretty comprehensive due diligence process that we say, Hey, these are all the things that we’re looking for. And now that we’ve figured out the way that we evaluate things, we move quickly. So that’s kind of the first piece of it, I think we’re you know, I want to talk about all the incredible things that maybe some of the limitations are is, you know, you have two people that are constantly working, right. And I do think that we have kind of stretched beyond our partners if you want to call it that. And as we think about now going into fun, too, and executing on fun, too, which is a reality today, we are thinking about okay, like, what does that team expansion look like? Where are we strongest where are we weakest? And where can we sort of add value around those things? You know, Kelly and I both collectively sit on a couple of different boards of our portfolio companies as well. And so we’re having to really think through what that looks like, because we’ve serviced our portfolio companies in a lot of different ways. And so just wanting to continue to be a value add, wanting to continue to be strategic, and then wanting to continue to be very fast and decisive and making sure that we can invest in the companies we like.
William Leonard
I agree with that. 100%. And one thing that you mentioned, I think, Julie, she’s kind of eager CFO, back office, secret weapon. And we have something similar like that at Valor, John Luke van Hall sees, you know, our back office, you know, doing all the dirty work, all the auditing those types of things. And I think that helps the firm scale, especially when that function is in-house internally. It just adds such a seamless dynamic of communication and transparency from a fun reporting, capital call perspective. So, you kind of hit the nail on the head with that. And now you have such a fascinating story of true hustle, right? You’ve been on both sides of the equation here, you’ve built, you know, a startup before you built multiple startups before, I believe. You’ve seen companies grow scale, you’ve seen companies die. And now here you are, as a principal, and investor helping companies grow and scale from many of the lessons that I’m sure you learned in building your company. And also, investing in seeing other companies just naturally die out as they do in this thing that we do called venture capital. So, tell us a little bit about your story and how you broke into VC.
Nassir Criss
I think that people try not to rely on luck as a thing. But I think luck is a symptom of timing, right? Like, sometimes the right thing just happens at the right time. And I’m a man of faith. And I do believe that everything happens the way it’s supposed to. But there’s just been some situations I’ve been in man where I’ve just been like, wow, like, I’m very fortunate that I was in that place at that time to be able to do that thing. Because if you look at my career, it’s like a zigzagging like, reveal. Like, it’s like, I’m not supposed to be here, I don’t have any of the foundational qualifications. And I didn’t go to business school, yet. So all in all, I think that everything that I’ve done, and everything I’ve tried to learn has stacked on top of itself, to get to the ultimate goal. So I think when I was in college, and I had, I had two goals, I was sitting down with one of my mentors, and I said, I want to be the best CEO that I can be. My dream job has always been to be the CEO of Apple. So I don’t know if anyone listens to this at Apple, maybe 10 years from now we can make that a reality. And then the other thing that I said Will and I didn’t even know what PE or venture capital was at the time was I wanted to buy and sell multiple companies like that is I said those things before I even knew what the structure of it was. And so those two kinds of items being my North Star, is what led me to want to start a company is what led to even though we’ve you know, relatively failed in that company from an exit or liquidity standpoint, we succeeded in that we got to fall in love with entrepreneurship and figure out okay, how do we roll these learnings into the next thing? And so that’s a little bit about you know, kind of kind of where I come from and why my mindset is the way it is, you know, I tell people that the true foundation of even that if you’ve been wanting to start something and build it it’s predicated on the fact that, you know, I come from a family that started from humble needs. And we are by no means kind of where I think our family should be, we’ve gotten a lot better over the generation that I’ve been a part of. But in a lot of ways, you know, I’m kind of out in front. And I’m only 27, you know, and there are people in my family that are 75. And so I take it very seriously the economic kind of health of my family, and what the generation after us might look like. And then beyond that, I’ve always been deeply invested in the community. So people that look like us people that come from places that I come from people that, again, don’t have the credentials to be in the rooms, but maybe have the talent or the sheer drive to be. And so a lot of my motivation has been tied to wanting to create opportunities for other people who weren’t adequately given those things. And then the last piece that I’ll just touch on a man, a kind of learning lesson that I’ve gotten along the way is I think when I realized I was capable of creating, I think everybody has this moment, right? Like, where you’re like, oh, I have this power as I can, I can do things, if people like the things I do, or people are interacting with the things I do, your ego starts to take over, you start to think that like, I’m so great, or like everything I’m doing is so great. And most of the time when I tried to do things on my own, under that pretense, they failed. The things that I’ve been a part of that have been successful, was that I came in and played a role very similar to any team, right, like you’ve played sports. When you come in, you play your role. Well, you know, that’s when you can be a part of a team that’s building something substantial. And that’s where I was a part of the first successful startup and went on to raise multiple rounds of capital. That was when I went into PE and saw them close on a billion-dollar fund. That’s why I went to Sixty8 Capital and helped the founding team get off the ground and continue to grow. And so I think that I’m now starting to understand my true talent, my true value, and my true role in a team, but also understand that to create this vision of a better future tomorrow that I see to be the CEO of a company to be buying and selling companies, you have to kind of kill the ego a bit and be willing to work alongside others that are just as brilliant, if not more.
William Leonard
Yeah. And I would love to double-click on that, and maybe dive in a bit further on that point. Because, you know, playing your part, in playing your role early on, is so important to how you grow in progress. Because you become known for something and I think it’s good right now that, you know, you and I are both at relatively small firms and were able to touch a lot of the day-to-day execution and operations of firm building, investing, deploying capital. And, you know, what are some of your general thoughts and learnings on progressing your career as a young junior VC? And, how does being the sort of Swiss Army Knife play an important role in the natural progression of, you know, the venture hierarchy from analysts to associate to senior associate to principal to VP, whatever each refresh respective firms track is like, how do you see this being a Swiss Army Knife plays an important part in that?
Nassir Criss
VC in particular, and maybe even like PE or investment banking, finance, in general, I think it’s like an apprentice game. Right? Like you can go to school, you can get the qualifications. But at the end of the day, you have to demonstrate that you can do the work. And work is very hard. And it’s very arduous. And it takes a long time. And there are different components. There’s finance, there’s business development, there’s operational efficiency, there’s some legalities of it. And so you have to demonstrate in this industry that not only are you capable of doing the work and doing it well, you’re capable of doing it over a long time. And I think that translates to really any industry, but specifically NVC. And so when you’re a junior person, it took me a long time to realize it, but sometimes it’s okay to be little bro. Because you’re getting the practice, right, like you’re getting to practice alongside other people that have been doing it for longer than you and for us, man, like you’re talking about an industry that has what 2000 investment professionals globally, like this, is still like a fairly nascent industry, right? So we talked about this the other day on the phone, like for us to be in the positions that we are I look at you will, like you’re gonna need to be the position you are like, is incredible, right? Because like you’re getting to come in where your partners have maybe spent the last 1520 years learning this game. But they started at a much further threshold, right? They were probably in their late 30s, mid-30s, whatever it may be. I mean, you’re already 10 years ahead, but now getting the knowledge that they have from the previous 20 years and So when I say to myself, like sometimes it’s okay to be little bro, it’s our trajectory. And you know, God willing, our lifetime tail is so long, that there’s so many things that we can learn. And there are so many ways that we can get better. And so the way that I’ve kind of cultivated my mindset is like, am I getting an opportunity to learn every single day new things? And currently, yes, right. But that doesn’t mean that I’m so short-sighted that I’m not thinking about, okay, how do I roll these learnings into the next thing, right? And so I’ve been able to now figure out what I’m good at what I’m not good at what I like to add value in what I don’t want to add value and how I can help portfolio companies operate. And I think that, as I kind of strategically plan for whatever’s next, it’s, I want to do this, but on a larger scale, right, like so. So I think that it’s a reframing of the mindset, right, like no one comes in, and it’s just automatically partner, we see the news headlines every day. But unless you were like a wanderlust kid, that at 21, sold the company for a billion dollars, like, people are still going to say, hey, you have to prove that you understand this work and that you can do it well. And that’s just the phase that we’re in. And so I used to kind of be stumped by it. Because I felt like, Ah, I’m not growing as fast as I want to. But I had to change my mindset. Sometimes growth is lateral versus just vertical. And sometimes growth even means taking a step back to be able to then take 10 steps forward. And so the reframing of that, and looking at other ways that I could kind of sharpen that that army, that Swiss army knife, you know, that we’re talking about in different ways to be a more rounded investor to be a more rounded operator, I think is what has helped me progress to leadership positions within the industry. Yeah,
William Leonard
I can double-click on that and deeply resonate with what you’re saying they’re not. And I want to transition the conversation here a bit, right? You spent some intentional time over the last few months, boots on the ground in many different cities like LA Denver, Charlotte, DC, and New York, and you were digital nomadic. And you wrote an incredible article on Medium about your time spent on the road, really immersed in these different cities. And you know, and one of the fascinating points that resonated with me in the article was your thoughts on finding outliers and pattern matching, and how essentially, investors are typically looking for the same things and in very recognizable patterns. So we’d love for you to expound on your thoughts here and how these insights around pattern matching versus finding outliers came to light during your time as a digital nomad. And also, it’d be awesome to understand the essence of wanting to digital nomad, as a VC.
Nassir Criss
Yeah, I guess I’ll start there. And then maybe I’ll get into a little bit of the pattern matching versus outliers, kind of a thesis that I came up with. But you know, I was leaving Kansas City. So I moved to Kansas City originally for Venture for America, which is a two-year fellowship, and entrepreneurship program for young people who are looking to build their own companies in the next three to five years. And so I was kind of placed in Kansas City, fell in love with the city fell in love with the community fell in love with their hunger for growth. But my two years were up. And so at that moment in time, I said, Okay, I’m either going to stay here in Kansas City and commit to building for several years, or I’m gonna go somewhere else, there’s been other places that have been on my radar, namely the West Coast. And so I was like, hey, like, maybe I’ll just go live other places, or maybe I’ll go home for a little bit. At that time, I had some mentors that I was kind of bouncing ideas off of which I frequently do. And one of them said to me, Hey, if you’re gonna be traveling and meeting people, you know, why don’t you put some intentionality behind it? And why don’t you write about it? And so, you know, collectively, we came up with this idea to travel to different, burgeoning, but also existing startup ecosystems, meet with their leaders across tech technology-enabled services, but also just like community leaders, right, like ecosystem builders, political leaders, etc. And just learn, like learn about the things that they were doing, that allowed their ecosystems to thrive and why maybe one seemed more successful than the other and what were the kind of measurements of success and things like that? And then I just did it. Like, I was like, okay, you know, I used my family’s home in Virginia as a home base, my grandmother’s house, but every like two weeks, I was on the road. And I would just spend time in these places. And the one thing overall that I started to learn is that no matter the geography, or the kind of backdrop we’re all in much more similar than I think we we choose to believe we are. Right. Like, I think that you’re in the southeast, and I’m in the Midwest. And there are some people in the Northeast, and there are some people in the West Coast. And while yes, the maybe cultures or customs are slightly different, or the way that we do things, or the way we define rounds are the way that we invest or strategies are different, like everyone is, namely looking for access, and education to be able to get kind of access. They’re looking for capital resources to then drive the things that they’re kind of thinking about and building. And then they’re looking for Kenick connectivity, you need a network of people that are going to help you get connected to partners, to customers, to strategic stakeholders to help you build your idea to reality. And so that was what I started to find. And I think that I saw, I was starting to meet some awesome people. I mean, I have to shout out cities like Tulsa, which I think are, you’re seeing Tulsa grow from from inception, almost now that they’ve kind of committed to their tech ecosystem. But it’s just really cool to see how they’re throwing a ton of resources into the city and into having founders come and move there. So that was dope to see, Philadelphia, I think is setting the standard for how their educational institutions are funding programming around startup founders and ideas. I haven’t seen anyone else do it better. I mean, like Drexel, UPenn. Wharton, like Temple, has innovation schools and programs that are funded in real dollars that are the size of like microphones and other places to students that want to be building things. And so there’s so many different ways, I think, to figure out how we drive the innovation economy. And what I realized the hyper-successful people are doing is they’re not necessarily pattern matching, pattern matching is a thing that we as investors do to try and minimize risk, right? Because at the end of the day, our job is to mitigate that risk. But they were looking for things outside the box, right? So maybe it’s yes, I’m looking at AI. But instead of looking at a functional feature of something that might make one small thing better. I’m looking at who’s going to redefine the way we cognitively behave as a society over the next 25 years, right? And then how have they figured out how to commercialize that? Or maybe they haven’t, maybe those are things that we can add resources and value to. And so I think that, especially in the geographies we’re in, where we’re looking at, you know, specific kind of targeted returns and specific types of companies, we’ve gotten constrained to this idea of, hey, well, we see what works, let’s look for the next things that fit those patterns of what works versus are we looking for the things that are truly going to change the way we behave, act and interact as a society. Because typically, those are the things that are driving innovation, and then again, are the most lucrative. And so I got to learn a bunch of lessons about that, man, I did write some of the article, I even built a contact database of folks that I thought were kind of like need to know people in the cities that I’m happy to share with anyone that goes and reads the article.
William Leonard
Yeah, and I think it’s just your name, and see your Chris on the medium is your handle. Is that right? Yes. Yeah. Yep. Yep. And, man, that’s, that’s so profound. And I think it’s natural for us at this point, right? We’re humans, we’re creatures of habits, and we have patterns that we follow daily. And it’s like, we’re taught from adolescence, that behavior, behaving in a pattern is a good thing that helps us fit into society. But I think on the other side of that is, when you look at the realm of company building, I think to achieve outsized success, you have to champion and pattern-breaking. And I think from from a cognitive behavior standpoint, you look at, you know, companies like Airbnb, and Uber, that transformationly shifted how we think about hospitality and rideshare. And I think we’re going to see the next wave of companies that are transformationally shifting how we operate in day-to-day life, with AI built over the next, you know, three 510 years or so. And I’m excited for that. And, man, that article was great. I encourage everyone who’s listening now to go to go read it, check it out, and immerse yourselves and the Cirrus thoughts. Appreciate that. Thank you. Yeah, man. And you know, you’ve been with Sixty8 for some time now. And you’ve been able to help shape the direction of the firm. And I think a big part of shaping the direction of a firm is bringing deals and in executing those deals. So we’d love to talk about maybe one of your favorite deals that you’ve worked on so far. And how do you build conviction around doing a deal And winning internal buy-in from Kelly any, any others on the team?
Nassir Criss
For sure. It wasn’t easy. It took some time, it was both a combination of me getting a little bit more confident in my abilities, but also truly learning how the team works, right? You have to buy into the strategy of the team that you’re with. And then again, to kind of reference an earlier point, you have to kind of play your role. And I think doing that well has carved out a lane for me where I’ve been able to earn trust with the team Kelly, and then the rest of our kind of investment advisory board and committee. And then also with our founders, you know, I don’t like to pick favorites, because I think that all of our portfolio companies are great and doing things in phenomenal ways. But you know, I can talk about one of our companies that’s growing the fastest, I would say, and that is a prediction shrink. So we talked about this deal before. Well, I’m still trying to figure out how I can get you in on it. But it is the world’s first fantasy sports stock market. So think sports betting except different. It’s a game of skill, where you can trade virtual shares of your favorite athletes. So you know, I am a huge fan of LeBron James, I can look at LeBron James’s performance on the court, I can look at some things that he does off the court, whether that be you know, things that come up in the media or news or whatever, and it affects his stock value on the platform, I can then invest in him. Similar to the stock market, I will get marginal gains over time, as he either performs above or below what the market is predicting he’s going to do the market being a sports analyst, sports reporter, team, ESPN kind of major conglomerates that are saying, Oh, we think LeBron is going to average XYZ or play this many games or do XYZ. They’ve been a huge hit in the market. They have several 100,000 followers, or excuse me, users, they have a pretty good following as well. But they have several 100,000 users, they’ve been able to transact over 16 million in transactions, you know, the company’s only been around a few years. And so they’re seeing incredible kind of spikes and growth right now and recently closed on their Series A, there is a $10 million series A an evaluation is just incredible, like almost tripled their valuation since we have invested and so to see them do so well, in this kind of nascent market reminds me of a couple of different things. And I think that is how I build conviction. I also just want to shout out to Abhishek Crumbly, who’s that collab capital, which is in your neck of the woods, because she introduced me to the founding team, so shout out to be. But they’re doing the things that we talked about. So they were building in an industry that is well-known sports has been around, I mean, we saw on COVID-19, sports did it stop, people will throw their last dollars into watching sports games because it gives them some sort of confidence or, or excitement or happiness or peace. So they’re building in the sports industry. They’re using technology to scale quickly. And they’re doing something novel, right? And so we have founder archetypes broken up within the Sixty8 thesis of things that we like to see. So there’s the bootstrapper, there’s the community builder, and then there’s the market maker. And these are kind of three buckets that we kind of funnel our founders into. And they are market makers, they’re doing something that’s never been done before. There are two other competitors in the market outside Dri Guys with Mojo being one of them, but have not successfully figured out their user experience. And so we saw, hey, you guys have kind of figured out something by being the first to the market. Secondarily, they provide a unique value offering that keeps their users engaged daily. A lot of the times when I’m trying to build conviction, I’m trying to figure out what is mission-critical. As in are people going to use this every day to accomplish whatever it is they want to do? Whether that be for enjoyment. Or whether that be for progress and work? Or is it nice to have? And if it’s nice to have, then it’s okay. It’s not that relevant to what we’re trying to do. People are not going to pay for it eventually going to have people churn. I mean, that’s where like all your unit economics come in, but foundationally like is this a need to have, and they figured out a way to be extremely sticky. They built an exceptional community around their users, that allows them to engage daily. I’m trying to figure out how much to say without giving away too much secret sauce, but they built this exceptional community where they’re fully engaged in their team members who are engaged with the users daily. And then lastly, you know, have been very strategic about going and getting partnerships with agencies, with sports players, with athletes with teams, and all those things combined. You know, you throw in Devin and Brad, who I think are just brilliant, right? Devin is a Harvard JD grad as well. You know, Brad is just phenomenal work. in investment banking, before he went into technology, and they’re super capable, and they’re super determined, and the last piece I’ll just kind of say on this about conviction is, you know, the obvious things are you have to be smart, and you have to be capable. And you have to have a good idea. You know, but you also have to be determined. And I saw a clip the other day about Sam Altman, where he talked about, you know, founders don’t estimate the frequency and propensity of bad things that happen when you’re building a company. And the ability to push through those bad things regularly, and then not give up is actually what separates the good from the great. And I saw that in the founding team with prediction strike after spending just a short amount of time with them. And so that’s how we kind of evaluated the deal. And it’s incredible to see that they have done well and are one of our top-performing portfolio companies. And it’s kind of similar to how we evaluate other deals as well. Nice.
William Leonard
Yeah, that is a fascinating company. And you’re right, they’re operating in such a market that didn’t die throughout COVID. I think sports was one of the only markets that thrived during COVID. And you look at where it is now from a segment price picks FanDuel. All these markets are just on fire right now companies are growing tremendously shout out surprise picks. They’re an Atlanta-based company as well. So I love how you think about backing founders building visionary companies that are pushing the boundaries, of what’s possible today. And I think that’s so important as an investor, from it a general perspective, but also from a pre-seed and seed-stage perspective, where you’re, you’re working with ideas that have very early functionality. And there’s not a lot of proof points there. And you have to be so convicted, and that this team is going to take this little egg, grow it, and eventually hatch and scale. And so that’s the thing that I just love about the early stage, venture capital, Nas, and man, this has been an incredible conversation. We could talk all day about you know, your insights and in Sixty8 and how you see the world from your lands, but I think this is a great place to wrap and I appreciate you for joining me today, man.
Nassir Criss
Yeah, thank you so much.
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