Running With Tech: the Athlete Venture Capitalist

As tech becomes ever more central to the future of society, athletes and sports leaders are becoming engaged. Why does Jets star Enunwa care so much about tech?
The following transcript has been lightly edited and condensed for ease of reading.
 
David Kirkpatrick: I think many of you are eager to see the wide receiver for the New York Jets. Great to have you, so glad to have you. And my friend, Rudy Cline-Thomas, who is—I was looking at your bio because—founder and managing partner of Mastry, which—but you do so many things. I can’t even keep track of all the things you do. But you help technology companies, you help sports figures, you do investing, and you also run a sports and technology conference every year. So you have sort of become the glue between the sports, especially basketball and football, I think, industry and technology and business. So I’ll let Richard talk more, but eager to hear the discussion. Thank you.
Richard Bradley: Thanks, David. Hey, Rudy, it’s weird, he didn’t say that we were the ones they came to see. [laughter] No, that’s all right, we’ll get over it.
So we’re here to talk about the intersection of sports and investing in technology. And let me start with you, Rudy, because you—as David suggested, you’ve kind of become a mentor in that space for athletes. And that’s not really how you started your career and I wonder if you could just walk us through how you got to that point and why.
Rudy Cline-Thomas: Sure. I started as a sports agent, so I started in 2000 out of Providence College and I was a finance and accounting major and I thought the only way to apply my two passions, which were sports and finance, was to possibly be an agent. I’ve always had the idea of helping athletes become businessmen, you know? I’d always had a penchant for finance and for entrepreneurship and the fact that I didn’t, you know, play professional sports, I always wanted to help these guys.
Bradley: Yeah, so let me pause. You said you’ve always had that idea of helping athletes become businessmen. That’s not—it’s not like wanting to become an astronaut or something. How did you get that? Where did that come from?
Cline: I think I always realized the power that the athletes had that they weren’t really exercising, so I realized that at a very young age. And again, I thought the only way to do that was as a sports agent and I realized very quickly that I was being a babysitter more so than applying what I’d learned in school so I quickly pivoted after a couple years to being a wealth planner and did that for ten years before getting into tech.
Bradley: And then from a wealth planner to a kind of a more of an investor being part of your identity.
Cline: Correct.
Bradley: I mean, you’ve invested in Allbirds, and Uber and LimeBike and Casper and a whole bunch of things. Talk about that transition from wealth manager to investor.
Cline: So around 2007, we realized—my partners and I realized that most of our returns were coming from tech companies and I just had a penchant to say, “You know what, we need to get in here a little bit earlier.” So I literally just started going out to San Francisco on my own to as many conferences as possible and started making relationships with the right VCs, and luckily enough, I met Josh Kopelman in 2008. He was in Philadelphia at the same time and he taught me the entire business and was—my rolodex started from that standpoint on.
Bradley: So Quincy, I want to hear a little bit about your side of the story. So I automatically liked Quincy when we met outside because I confessed to him that I’m a lifelong Giants fan and he forgave me for that, so—but I’m coming over. He’s winning me over. I know you’re from California originally, you went to Nebraska. You had the longest pass completion, 99 yards, right? That’s a record there.
Cline: I didn’t even realize you were that fast.
Bradley: And the offensive player of the year your senior year. And then you got drafted sixth (round). And that’s, you know, not a terrible draft, but it’s not like number one. But you’ve really, like, made yourself an important part of the team. Like talk a little about that and then how you kind of came to work with Rudy and that journey.
Quincy Enunwa: Yeah, so I’d say, I guess being the son of immigrants, I’ve always—that kind of hard work and passion has always been kind of instilled in me.
Bradley: Where are your parents from?
Enunwa: Nigeria. My mom actually came about a month and a half before I was born. I don’t know if you’re really supposed to do that, but [LAUGHTER] she was determined.
Bradley: I think you’re not, actually.
Enunwa: But, yeah, I think, you know, just always, you know, having that hard work put in me, it kind of just made me fight that much harder than everybody else. Being a sixth round draft pick, you see guys that get cut all the time. It’s a cutthroat business, you know. The guys that were drafted with me—I got drafted with 12 guys and I’m the only one left now, you know, six years later. So it’s really tough out there and I think that kind of has made me become who I am today. And so it’s always made me kind of want to do more, become more, be a better person. So starting about two years ago, I actually was injured and I was out for the whole year. I had neck surgery.
Bradley: That must have been pretty scary.
Enunwa: Yeah, very scary. And so for me it was like, okay, well, I’ve kind of planned my whole life around being a football player but now football can actually be done, you know. I could not be a football player anymore. So my next thing was like, okay, who am I as a person? What can I do? Who can I meet? You know, I’m in New York, I’m in a great area, and so I started off by doing an internship. I spent three weeks in San Francisco, did an internship with StubHub. And I learned a lot about myself.
Bradley: While you were injured?
Enunwa: Yeah, yeah, yeah.
Bradley: That’s got to be kind of an unusual thing.
Enunwa: It definitely is. Guys always looked at me like, “Why don’t you just chill?” But it was like, you know, I don’t know if I’m going to be able to be the same person I was before. You know, I knew I had the hard work and the work ethic and all that other stuff, but it was like—
Bradley: So you were concerned about your ability to keep playing?
Enunwa: Exactly. And really, I was concerned about my future, you know, because a football career lasts maybe two, three years. So fast forward, you know, as I’ve been building up contacts and everything, I actually met Rudy through a mutual friend and he’s just been instilling so much information in me and it’s just been, you know, beneficial for myself. And hopefully, you know, I can get on the same level as him with investing, but at least if I can gain some knowledge and pass it on to the next guy, you know, I’ll feel great about myself.
Bradley: Let me throw a question to both of you. There’s been a lot of talk obviously about social media here. But athletes have a real specific connection to social media and we’ve talked a lot about how that is empowering athletes in a way that is different, that has given them more control over their brand. I wonder, for both of you, if you can talk about kind of how that’s affected the way you’ve built your business, and Quincy, about how it’s kind of expanded your sense of what you can do with your brand beyond football.
Cline: Well, me personally, I don’t have any social media at all, so it doesn’t affect me directly.
Bradley: You have a digital newsletter, that kind of counts.
Cline: That’s true, that’s true. That does count. But, you know, he and I always actually talk about the power of the athlete and how it’s growing exponentially. So one out of every three persons that actually, you know, are on social media follow an athlete. And their reach is extending further than it’s ever been before. I think they’re exercising that power in reference to business like never before. I know he’s doing a couple things right now in that sense of touching his fans and doing different things as well too, and extending that reach and building his business around that, so you can, you know.
Bradley: Quincy, I mean, among non-athletes, right, there’s obviously huge variation in attitudes toward social media. Some people are incredibly diligent, some people are pretty haphazard about it. Is that the same sort of situation in the locker room in the sense that you have people who are like, “This is—I’m making this a mission,” and other people are like, “That is not my thing.”
Enunwa: I’d definitely say that that’s what goes on in the locker room. I think you have so many personalities in the locker room. So you have guys like, say for instance Kawhi Leonard, you know, he’s not a football player, but you look at a guy like him who has no social media presence because it’s not really the type of person he is. Then you look at a guy on the football field like Juju Smith-Schuster and he’s all over social media. He has YouTube pages, he does everything. So I mean it’s a wide spectrum of guys, you know, just like there’s a wide spectrum of personalities.
Bradley: But is there a sense that there’s clearly a brand building and like business reason for being out there.
Enunwa: Of course. And I think, you know, as social media grows, you see so many people making money off of social media. So you can sell T-shirts, you can sell so many different things. And then you can also be a brand partner. And so guys definitely take advantage—I’ve taken advantage of that.
Bradley: Yeah, so tell us about that. What’s your experience like with social media?
Enunwa: Oh yeah, my experience has been—I mean, it’s a gift and a curse, right? Because it gives people access, and so a lot of times they give their opinions on your performance. But at the same time, you know, like I said, it’s a gift and it gives you an opportunity to kind of interact and really see who does love you as a player and appreciates your abilities, as well as the brands that appreciate you and really do their research on you and find out what they can do to kind of help you grow your brand as well.
Bradley: So I want to throw out a question, again, for both of you, which is, it’s kind of a general question about the level of financial savvy. We talked about tech savvy among athletes. Let’s talk about financial savvy. You know, in the space that I come in, “Worth” magazine, which does a lot of coverage of finance and wealth management, there was a period a few years ago where all of a sudden every financial firm was talking about how they had to recruit athletes and entertainers. And so a bunch of them came through our offices, the wealth managers who were doing this, and said, well, the big challenge is that, you know, athletes have like a posse that they come with and their people who come with them from the neighborhood or from the streets or whatever. Or they want to buy their mother a house the first contract they get. And it’s one of those things where it’s hard to tell where truth ends and stereotype begins, and possibly racist stereotype, right? Can you talk about what the reality of that situation actually is?
Cline: Well, I think, you know, from the general public standpoint and just propaganda, it’s always popular to talk about, you know, someone going broke versus success, right? So at the end of the day we’ll hear more of those stories than we’ll hear about the guys that are actually doing well. I think nowadays, you know, the athlete’s, you know, much more savvier. I think more athletes, and not to speak for you, Quincy, I think they’re more aware now of the pitfalls just—again, just because it’s widely reported, of the athletes. So there’s no athlete that comes into the league that doesn’t understand exactly what they’re coming up against, right? You know, no one’s blind to it whatsoever, right? So—and then you have gentlemen like this guy right here that are just totally aware of their opportunity and there’s more and more of them like that now. You know, I think these guys generally speaking, you know, pick up a “Forbes” magazine before they pick up a “Sports Illustrated,” and I don’t know if it’s because “Sports Illustrated” is dead now, but at the same time—you know, at the same time, they’re very, very much aware of the opportunities and just business.
Bradley: I think you actually meant to say “Worth” magazine.
Cline: “Worth” magazine, yeah, there you go. There you go.
Bradley: That’s okay, no worries.
Cline: And they are much more keen now to, again, just employing the different opportunities that they have out there.
Bradley: Right. Would you say the same?
Enunwa: Definitely. You know, there’s obviously, like I said, with the wide spectrum, there’s guys that still make those same decisions. Like I said while we were talking outside, you know, I know guys in college who were taking out loans to help their parents from back home, so the minute they made it to the league, you know, those same people were still reaching out trying to grab a piece. So you always have that, you know, and I think there’s going to be that in any field, right? If you hit the lottery, people are going to end up trying to get a piece of that. But you know, at the same time, there’s so much information out there, so much bad information about how many players go bankrupt, basketball, NFL, so guys try to make sure that they can prevent that for themselves.
Bradley: And Quincy, if you don’t mind, I’m going to make it a little personal for you. We were talking and you said, you know, the weird thing about being a pro player is that like everybody knows what you make.
Enunwa: Yeah.
Bradley: So I’m just going to say what do you make.
[LAUGHTER]
You signed a four-year contract not long ago for $34 million bucks. Congratulations, that’s awesome. I mean, I think when people know how football players risk their bodies, it doesn’t—you guys earn your money. And for a lot of folks that sounds like a lot of money compared to, say, athletes in the NBA, it’s significantly less. But when you actually figure in agents’ cuts, taxes—and you guys pay taxes all over the country, as I understand.
Enunwa: Yeah, every state we play in, we pay taxes.
Bradley: Does it give you a big feeling of security, knowing that your career is of indeterminate length, you don’t know how long you’re going to be able to play?
Enunwa: I mean, it definitely gives you more security. But even then, you still don’t feel 100% secure. You know, because for one, that money hasn’t—I haven’t touched any of that money yet. You know, it hasn’t hit my bank account and there’s—anything can happen, right? You know, and another thing is only a certain percentage of it is guaranteed.
Cline: Exactly.
Enunwa: You know, so as great as it looks up there, you know, it’s not exactly what I’m touching.
Bradley: As I said, I mean, I think you guys earn it more than in any other sport for sure.
Enunwa: I appreciate it.
Bradley: Let’s get back to the tech question, which is how do you find the companies that you like and what are the criteria that you look for?
Cline: Yeah, it started out with just listening to the right people. So I always say I’m not the smartest guy in the room, but I can identify who is. And I’ve been able to—
Bradley: You know, I always find that the smartest guys in the room are always the ones who say they’re not the smartest guys in the room.
[LAUGHTER]
Cline: So I was lucky enough to have some great advisors that allowed me to invest—co-invest alongside them, so, early enough, and just taught me along the way, you know, how to focus on the diligence in companies. And I basically focused on investing in stuff that I understand, you know. So you know, as I’ve gotten more experienced, you know, obviously you know you get to understand more and it’s widened the base, my investment base.
Bradley: I want to get two more questions in real quick and then let’s see if there’s some questions from the audience. One is you do an annual conference. Let’s hear a little bit about what you guys do there and who goes.
Cline: Sure. It’s called the Players Technology Summit. It’s in San Francisco. It’s a day and a half of curation of topics that I think the guys are really interested in, in reference to tech. So we try to bring top VC CEOs and athletes in one room for a day and correspond, you know, in reference to panel discussions.
Bradley: So the final question I’ve got is I’d love for both of you to talk about what this process of turning athletes into investors and equity holders means in a kind of bigger picture way. I mean we’ve all heard about, you know, the icons who’ve done this, LeBron, Magic, A-Rod, Michael Jordan, etcetera. But you’re trying to extend this to a broader group of folks who traditionally have just been employees whose career after their sport was uncertain, right? Lots of folks have had financial troubles after their retirement from pro sports. Or they might invest in, you know, a car wash or a restaurant or something. But what you’re really trying to do is empower a group of folks who may not, you know, have not necessarily been in that place before. Are you pretty conscious of that? This is a kind of a changing the world sort of thing you’re doing.
Cline: Well, I don’t know if it’s changing the world, but I think the idea is, you know, I always tell him that my children will follow him and what he’s doing more so than me in the future, right? So these are the future leaders, so if I can have a hand in teaching him, you know, exactly how to take advantage of the opportunities and learn and lead, then I think that I’m doing something different, you know, so.
Bradley: But if you don’t mind me pushing a little bit, you know, the worlds of big money investing, of tech, these are pretty white spaces, right? To bring in a group of athletes, most of whom, I think most of whom are African American, it’s meaningful. Quincy, do you feel the same way?
Enunwa: Yeah, I definitely feel the same way. I think that—not only that, but it will also allow us to kind of put the money back in our own neighborhoods as well, you know, so if we’re able to then invest in ourselves, you know, then we can hopefully bring more people up to be doing the same thing.
Cline: Yeah, we talk about that all the time.
Bradley: Let’s take a couple questions. Yeah.
Audience 1: Quincy, what kind of services does the NFL have to help with wealth management and to help prevent some of the problems that we’ve seen in the past?
Enunwa: They actually offer a lot of things. We do business conferences. We do—like I said, the externship, I actually got that through the NFL PA. So our players union actually does a lot to try to help players out. It’s just, I think one of the biggest issues has been people not taking advantage of it. The resources are all there. Like contrary to popular belief, we have all the resources to be successful, it’s just that people don’t take advantage of it. You know, the thing about being in the NFL is that, you know, not only do you get money at such a young age and so much of it, but you also get a lot of access. And so it’s about what do you access, you know? Some guys access the night life and all those other things, so that kind of puts them behind the eight ball, you know? So I think it’s always out there. It’s just about taking advantage of it.
Bradley: I saw a question over here.
Audience 2: I’ve got one over here.
Bradley: Okay. I’m sorry, I saw this gentleman over here and then we’ll come right back.
Ellison: Sure. Hi, Mike Ellison. Two-part question. Should college athletes get paid? And then what can colleges in the NCAA do to sort of help them transition to kind of post-athletic life, you know, in the business world and investing in particular?
Cline: I’ll just say, I’ll start out by just saying definitely they need to get paid. The question is who gets paid and how much, right? So I think the consensus is definitely they should get paid. I think it’s just who do you divvy it up amongst and who gets more or is it equal. I think that’s actually the real question.
Enunwa: Definitely, I agree. And then on the other part, it’s hard to kind of focus on the investing—that’s what you asked, right?
Ellison: Yeah, investment, business and the sort of post—
Enunwa: Well, see, the problem is, like, you have a lot of people going to school for different reasons. And so you can’t always target the one person or the ten people that want to make it to the NFL or make it to the NBA because they also have other things on their plate. You know, you have to go to school, you have to—you know, you have families to take care of sometimes, and then you have football. So at that point, it’s hard to really then add on like, “Let’s try to work on investing,” you know what I mean? So I mean, I’m sure they could try to do it, but I’m not sure that many people would really jump into it.
Bradley: I think we have time for one more.
Audience 3: So since the conference is really focused on community and collaboration, I wanted to sort of flip the whole panel on its head. Because one of the things that’s happening right now is that, especially with sneakers, is sneaker culture is completely going towards consumers. They’re the people who are actually buying the sneakers, redesigning them, and selling them and creating a secondary market. So I’m curious, from your guys’ perspective, how it’s affecting your choices, how it’s affecting, like, whether you’re thinking now about how to enter the collaboration with the consumers, how you’re using social media to actually think about the downstream design effect so that—because how people are designing their own shoes is really like part of the deal. And it’s changing—from my perspective, it’s changing the whole economics of shoe design because the fundamental proceeds of the sale of the shoes is going to the consumers who are selling, buying pairs, creating them, changing them up, selling them, right? They’re making the money. The sneaker company is still making money too. It’s not like they’re getting cut out of the equation.
Bradley: So the question is how are you guys adapting to the power of the consumer and leverage through social media to drive a market, right?
Cline: Well, I mean, I think it starts with supply chain. So you know, you have to have a back end supply chain to support that. So you know, it’s easy to say, you know, from the front end, you know, you have all these followers and you can sell directly to them but, you know, there’s a business behind that. So that hasn’t caught up yet. You know, we see the Jenners taking full advantage of that with the back end supply chain help that they have, but I think that will multiply. But again, the sneaker market’s going to change. You know, it’s going to get taken away from the consumer I think sooner than later. And that secondary marketplace as well, that’s changing as we speak.
Enunwa: Yeah, somebody just bought a secondary market.
Bradley: I think that we could take a bunch more questions. I’m sorry I think—right, I think we need to wrap up. We’re standing between people and their alcohol, so. Gentlemen, I want to thank you both so much.
Cline: Thank you for having us.
Bradley: And thanks to all of you.
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