Earlier this year, Lucra Sports founder and CEO Dylan Robbins did something no one had ever done before.
He secured prominent public investor Cathie Wood and her ARK Invest Venture Fund to lead the startup funding round.
Lucra announced last month that it had raised $20 million in Series B led by ARK Fund with participation from several other VC firms. Robbins brought ARK in despite the fund's previous failure with a similar esports company. Skillz is a skill-based gaming platform that the fund invested heavily in and then sold at a loss.
On top of that, Dylan landed this big catch as an investor even though his company isn't in AI, a field that all venture capitalists are currently pursuing.
Lucra offers white-label interactive gaming contests as a new type of loyalty program for businesses serving consumers. Rather than earning points towards coupons, for example, Lucra's customers offer online tournaments for prizes and support friendly bets between customers on who will win the game. The company's customers include Five Iron Golf, Dave & Buster's, and Chess King.
Robbins said there are two secrets to how he overcame these challenges and secured big-name investors.
1. Be friendly to everyone, no matter where you are. You never know when a casual conversation will turn into a hot topic with your major investors.
2. You don't need to be a famous AI scientist or build AI, such as models or agents, to use AI to lead your pitch.
The seeds of Lukla's fundraising efforts began when Robbins was playing darts at a bar in New York. He met another guy at the dartboard and they enjoyed a few games together.
“Six months later, we ran into each other again at a bar, the same darts bar. I was like, 'Nice to meet you. How's it going?'” Then we started talking and I asked him what he did for work. And he told me he worked at the Ark,'' Robbins recalled.
Robbins told him about Lukla, and that contact introduced him to ARK's investment team, who ended up writing a small check for the Series A round.
“My first piece of advice about all of this is you never know who you're talking to. Just walk around, be nice, meet people, and have fun,” Robbins says. That will lead to good conversations, which will lead to introductions, he said.
Fast forward a few years to the end of 2025, and AI was overtaking venture capital like honeysuckle.
Lucra Sports has carved out a niche for itself with white label services. The company was poised to launch a Series B to drive growth and encourage new ideas such as adding mini-games to the service. (Lucra just invested in a minigame development partner to build this feature.)
But Robins kept running into walls in the form of AI.
“We were raising money in the fourth quarter of 2025, which was, and still is, kind of the peak of AI disruption,” Robbins said. “One in three calls, the first thing I do is stop the meeting and say, oh, we're just investing in AI right now, we don't want to waste our time. They wouldn't even let me pitch.”
The rest told him they would just invest in AI after hearing the pitch.
So Robbins tried a new tactic. He tailored his pitch and deck to be ready to discuss AI. The revised pitch argued that if AI worked, people would have more free time to play games with friends in bars or online, meaning his business would be a winner, and if it didn't work, non-AI betting would start to look like a smart diversification. Either way it was a hedge.
“A few people took it seriously,” he said of his pitch. Luckily, ARK was one of them. Once committed, the lead investor introduced other VCs to help close the round.
Underpinning all of this, he said, are good business fundamentals, including “consistent year-on-year growth, not a one-off spurt.”
The final lesson Robbins learned is that VCs want to hear big dreams, especially for non-AI businesses. Robbins had one. It's an addressable market for people who play all kinds of games, from pickleball to wordle.
“So our TAM is pretty much every American between the ages of 18 and 70, right?” Robbins said. Still, he had one VC send a rejection letter, which he printed and stuck on his wall.
“I sent them our growth chart and our TAM. It was tremendous, showing decent growth potential. Billions of TAM. And the reply was, 'The TAM is too small.'” That was the answer. Similarly, our growth rate has been too slow,” he said.
He said it was a “reminder” to “think bigger”.
“If I want to raise venture capital funding, I have to put myself in that mindset and really try,” he added.
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