Earlier this year Business Sports founder and CEO Dylan Robbins did something no one else had done.
He tapped well-known public investor Cathie Wood and her ARK Invest Venture Fund to lead the startup fundraising round.
Lucra announced last month It said it raised a $20 million Series B round led by the ARK fundwith the participation of several other VCs. Robbins attracted ARK even though the fund had previously burned out on a similar eSports company: Skillz, the skill-based gaming platform that the fund is based on. invested heavily before leaving with a loss.
What’s more, Dylan landed this big fish as an investor, even though his company isn’t in an area that all VCs are chasing right now: AI.
Lucra offers white-label interactive gaming contests as a new type of loyalty program for consumer service businesses. For example, instead of earning points for a coupon, Lucra’s customers offer online tournaments for prizes or support friendly bets between their customers on who will win a game. His clients include Five Iron Golf, Dave & Buster’s and Chess King.
Robbins told us that he has two secrets to winning a major investor against such odds:
1. Be friends with everyone, everywhere because you never know when a casual conversation will turn into your main investor.
2. Guide your speech with artificial intelligence even if you’re not a famous AI scientist and don’t deal with models, agents or AI.
To the first point, the seeds of Lucra’s fundraising journey began when Robbins was playing darts in a New York bar. Met another guy on the dartboard and they enjoyed a few games together.
“Six months later, we ran into each other again in a bar. The same darts bar. It was, ‘Nice to see you. How’s it going?’We talked and I asked him what he did for work. And he told me he worked at ARK,” Robbins recalled.
Robbins told him about Lucra, and the connection introduced him to the investment team at ARK, which started writing a small check in the Series A round.
“My first piece of advice in all of this is you never know who you’re talking to. Just walk around, be friendly, meet people, have fun,” Robbins says. Let it lead to good conversations, which will lead to introductions, he said.
Flash forward a few years to the end of 2025, when AI will overtake venture funding like honeysuckle.
Lucra Sports has really hit the ground running with its white labeling service. It was ready to raise a Series B to fuel growth and new ideas like adding minigames to its offerings. (Lucra just invested in a minigame development partner to develop this capability.)
But Robbins kept running into an AI-shaped wall.
“We were growing in the fourth quarter of 2025, which was the peak of artificial intelligence then as it is now,” Robbins said. “One in three calls, the first line, they cut the meeting and said, ‘We’re only investing in AI right now, I don’t want to waste your time.’ To the point where they wouldn’t even let me talk.”
The rest told him they only invested in AI after hearing the voice.
So Robbins tried a new tactic. He set up his pitch and deck to discuss AI out of the gate. The revised pitch argued that if AI worked, people would have more free time to play games with friends at the bar or online – so his business would be a winner – and if it didn’t, the non-AI bets were starting to look like a smart diversification. It was a hedge either way.
“It was a small group of people who would take it really seriously,” he said. ARK, fortunately, was one of them. After the analysis, the lead investor made pitches to other VCs to help fill the round.
Underlying all of this, he said, are good business fundamentals, including “not just a boost, but steady year-over-year growth.”
The last lesson Robbins learned was that VCs want to hear a big dream, especially for non-AI businesses. Robbins was one: a general-address market of anyone who played anything from pickleball to Wordle.
“So our TAM is pretty much every American between 18 and 70, right?” Robbins said. Nevertheless, he sent a rejection letter from a VC, which he printed and posted on the wall.
“I sent them our growth chart and the crazy TAM to the right growth potential, huge, big, billion TAM. The response was, ‘TAM is too small.’ This was the answer. As our growth rate was very slow.
He said it was a “reminder” for him to “think bigger.”
“I have to put myself in that mindset and really swing for the fences if I want to raise venture capital money,” he said.
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