
Earlier this year, Lucra Sports founder and CEO Dylan Robbins did something no one had ever done before.
He tapped prominent public investor Cathie Wood and her ARK Invest Venture Fund to lead the startup’s funding round.
Lucra announced last month that it had raised a $20 million Series B led by ARK Fund, with participation from several other VCs. Robbins previously attracted ARK despite a major loss of funds at a similar esports company, Skillz. Skillz is a skills-based gaming platform in which the fund invested heavily before taking losses.
Moreover, Dylan caught this big fish as an investor even though his company is not in AI, a field that every VC is currently chasing.
Lucra offers white label interactive gaming competitions as a new kind of loyalty program for businesses serving consumers. For example, instead of earning points through coupons, Lucra’s customers offer online tournaments for prizes or support friendly betting between customers on who will win the game. Customers include Five Iron Golf, Dave & Buster’s and Chess King.
Despite the odds, Robbins said there are two secrets to how he attracts big-name investors.
1. Be kind to everyone, everywhere Because you never know when a casual conversation might turn into a major investor.
2. Drive your presentation with AI This is true even if you are not a famous AI scientist and are not building models, agents, or AI.
First, the seeds of Lucra’s fundraising journey began when Robbins was playing darts in a New York bar. He met another man at the dartboard and they enjoyed playing a few games together.
“Six months later, we ran into each other again at the same darts bar. It was like, ‘Nice to meet you. How are you?’ It felt the same. And we got talking and I asked him what he did for work. And he said he worked at ARK,” Robbins recalled.
Robbins told him about Lucra, and the representative introduced him to ARK’s investment team, which resulted in him writing a small check in the Series A round.
“My first piece of advice for all of this is you never know who you’re talking to. Just wander around, be friendly, meet people, and have fun,” says Robbins. He said that will lead to good conversation, which will lead to referrals.
In just a few years, by the end of 2025, AI will surpass venture capital like Honeysuckle.
Lucra Sports has truly found its way with its white labeling services. We’re ready to raise our Series B to fuel growth and bring new ideas to the table, like adding mini-games to our product. (We invested in a minigame development partner to build this feature called Luke.)
But Robbins kept running into AI-shaped walls.
“We were raising for the fourth quarter of 2025, which was still the peak of the AI disruption,” Robbins said. “One in three calls, on the first line, they interrupt the meeting and say, “Oh, we’re only investing in AI right now. I don’t want to waste time. “To the point where they wouldn’t even let me present,” he said.
The rest told him they were investing in AI only after hearing the presentation.
So Robbins tried a new tactic. He tailored his pitch and deck to discuss AI right out of the gate. The amendment argued that if AI works, people will have more free time to play games with friends in bars or online, and thus his business will be a winner, and if not, non-AI betting is starting to look like a wise diversification. It was a fence either way.
“It was a small group of people who took it seriously,” he said of his pitch. Fortunately, ARK was one of them. Once committed, the lead investor introduced other VCs to help build the round.
Underpinning all of this were good business fundamentals, including “consistent growth year after year, not just one-off growth,” he said.
The final lesson Robbins learned is that VCs want to hear big dreams, especially for non-AI businesses. Robbins had an entire market for anyone playing any kind of game, from pickleball to Wordle.
“So our TAM is pretty much all Americans ages 18 to 70, right?” Robbins said. Nonetheless, he had one VC send him a rejection message, which he printed and posted on his wall.
“I sent them our growth charts and our TAM. We had crazy, huge growth potential, huge, big billions of TAMs. And the response was, ‘Your TAM is too small.’ That was the response. Our growth was too slow,” he said.
He said it was a “wake-up call” for him to “think bigger.”
“If you want to raise venture capital money, you have to have that mindset and really move for the fences,” he added.
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