How an eSports startup raised $20M by pitching VCs obsessed with AI

Earlier this year, Lucra Sports founder and CEO Dylan Robbins pulled off a fundraising feat no other startup leader had managed before. He convinced Cathie Wood, the high-profile public investor, and her ARK Invest Venture Fund to lead his company’s latest capital raise. In March, Lucra announced a $20 million Series B round, with ARK as the lead investor alongside several other venture capital firms. This was a surprising move, given that ARK had previously taken a major hit on a similar eSports and skill-based gaming platform, Skillz, after investing heavily and later divesting at a loss.

What makes Robbins’s achievement even more remarkable is that Lucra operates far from the one sector consuming nearly all VC attention right now: AI. Instead, Lucra provides white-label interactive gaming competitions as a novel loyalty program for consumer-facing businesses. Rather than earning points toward a discount, clients like Five Iron Golf, Dave & Buster’s, and Chess King use Lucra’s platform to host online tournaments for prizes or enable friendly wagers between customers on game outcomes. It is a clever, non-AI bet in a market obsessed with artificial intelligence.

So how did Robbins land a name-brand investor against such long odds? He shared two key strategies.

First, be friendly to everyone, everywhere , you never know when a casual chat can turn into a major investment. The seeds of this deal were planted when Robbins was playing darts at a New York bar. He struck up a game with a stranger, and they enjoyed a few rounds together. “Six months later, we ran into each other at the bar again. The same darts bar. It’s like, ‘Good to see you. How’s it going?’ And we got to talking and I asked him what he did for work. And he told me he worked at ARK,” Robbins recalled. That connection led to an introduction to ARK’s investment team, which eventually wrote a small check in Lucra’s Series A. “My first piece of advice on all of this is you never know who you’re talking to. Just go around, be nice, meet people, have fun,” Robbins says. Those positive interactions lead to good conversations, which lead to introductions.

Second, lead your pitch with AI even if you aren’t building AI. By late 2025, AI had completely overtaken venture funding. Lucra had found its stride with its white-label service and was ready to raise a Series B to fuel growth and develop new features like mini-games. But Robbins kept hitting an AI-shaped wall. “We were raising in Q4 of 2025, which was then, like even now, kind of peak AI mayhem,” he said. “One out of every three calls, the first line, they would stop the meeting and say, oh, we’re only investing in AI now, I don’t want to waste your time. To the point where they wouldn’t even let me pitch.” The rest told him the same after hearing his pitch.

So Robbins changed his approach. He rewrote his pitch and deck to discuss AI right from the start. His revised argument was a hedge: if AI succeeds, people will have more free time to play games with friends at bars or online, making Lucra a winner. If AI fails, a non-AI bet looks like smart diversification. “It was a small cohort of people that would really take it seriously,” he said of his AI-led pitch. ARK was one of those few. Once committed, the lead investor introduced Robbins to other VCs to fill out the round.

Underpinning all of this were strong business fundamentals, including “consistent year over year growth, not just one spurt,” Robbins noted. The final lesson he learned was that, especially for a non-AI business, VCs want a big dream. Robbins had one: a total addressable market of anyone who plays any kind of game, from pickleball to Wordle. “So our TAM is almost every American that’s 18 to 70, right?” he said. Even so, one VC sent a rejection he printed out and posted to the wall. “I sent them our growth chart and our TAM, which was like crazy, up into the right growth potential, huge, big, billions of TAM. And the response was: ‘TAM’s too small.’ That was the response. Like, our growth rate was too slow,” he recalled. That rejection served as a “reminder” to “think even bigger.” Robbins added, “I have to put myself in that mindset and really swing for the fences if I want to raise venture capital money.”