Earlier this year, Work Sports founder and CEO Dylan Robbins did something that no one else has ever done: He landed famed public investor Cathie Wood and her ARK Invest Venture Fund as a lead in a startup fundraising round.
Lucra announced last month that it raised a $20 million Series B, led by the ARK fundwith participation from several other VCs.Robbins attracted ARK even though the fund had previously gotten badly burned on a similar esports company: Skillz, a skill-based gaming platform in which the fund invested heavily before divesting at a loss.
On top of that, Dylan landed this big fish as an investor even though his company is not in the one area that all VCs are currently chasing: AI.
Lucra offers white-label interactive gaming competitions as a novel kind of loyalty program for businesses that serve consumers. Rather than, say, earning points toward a coupon, Lucra’s clients offer online tournaments for prizes, or support friendly wagers between their customers on who will win games. Its customers include Five Iron Golf, Dave & Buster’s, and Chess King.
Robbins told us there were two secrets in how he landed a big-name investor against such odds:
1. Be friendly to everyone, anywhere because you never know when a casual conversation will turn into your major investor.
2. Lead your pitch with AI even if you aren’t a famed AI scientist and aren’t building models, agents, or anything AI.
To the first point, the seeds to Lucra’s fundraising journey began when Robbins was playing darts in a New York bar. He met another guy at the dartboard, and they enjoyed a few games together.
“Six months later, we ran into each other at the bar again. The samedartsbar.It’slike, ‘Good to see you.How’sit going?’ And we got totalkingand I asked him what he did for work. And he told me he workedatARK,” Robbins recalled.
Robbins told him about Lucra and the contact introduced him to the investment team at ARK, which wound up writing a small check in his Series A round.
“My first piece of advice on all of thisisyou never know whoyou’retalking to. Just go around, be nice, meet people, havefun,” Robbins says. Let that lead to good conversations, which will lead to introductions, he said.
Flash forward a few years to the end of 2025, when AI had overtaken venture funding like honeysuckle.
Lucra Sports had really found its lane with its white-labeling service. It was ready to raise a Series B to fuel growth and new ideas like adding mini-games into its offerings. (Lucra just invested in a mini-game development partner to build out this capability.)
But Robbins kept running into an AI-shaped wall.
“We were raising in Q4 of 2025, which was then, like even now, kind of peak AI mayhem,” Robbins 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 they were only investing in AI after they heard the pitch.
So Robbins tried a new tactic. He adjusted his pitch and his deck to discuss AI right out of the gate. The revised pitch argued that if AI works, people are going to have more free time to play games with friends at the bar or online — hence his business will be a winner — and if it doesn’t, a non-AI bet starts to look like smart diversification. It was a hedge either way.
“It was a small cohort of people thatwould really take itseriously,” he said of his pitch. ARK, fortunately, was one of them. Once committed, the lead investor made introductions to other VCs to help fill out the round.
Underpinning all of this were good business fundamentals, including “consistent year-over-year growth, not just one spurt,” he said.
The final lesson Robbins learned was that, especially for a non-AI business, VCs want to hear a big dream. Robbins had one: a total addressable market of anyone who plays games of any kind, from pickleball to Wordle.
“Soour TAM isalmost everyAmericanthat’s18 to 70, right?” Robbins said. Even so, he had one VC send a rejection that 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 said.
He said this was a “reminder” to him “to think even bigger.”
“I have to put myself in that mindset and really swing for the fences if I want to raise venture capital money,” he added.
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