Underdog CEO: “If we can be the best at building product, we’ll build the biggest company in this space.”

Underdog CEO Jeremy Levine sat down with Masters of Scale earlier this month, offering a founder’s-eye view of building—and rebuilding—companies in one of the most turbulent corners of tech.

The conversation traced Levine’s path from hustling on Craigslist to launch his first startup, to navigating the bruising daily fantasy sports (DFS) regulatory battles, to now steering Underdog with a product-first philosophy. His arc mirrors the evolution of modern sports betting itself—early chaos, existential legal fights, and now billion-dollar businesses chasing product differentiation.

Early hustle: DFS survival

Levine’s entrepreneurial streak started with StarStreet, a sports stock market built with engineers he found moonlighting on Craigslist. As DFS gained traction, he pivoted into daily contests and in 2014 sold the company to DraftKings.

That same year, DFS nearly collapsed. The New York Attorney General ruled the format illegal gambling, and a wave of states followed. Operators banded together under the Fantasy Sports Trade Association to fight back, culminating in a 2016 late-night New York Senate vote that legalized the contests. For Levine, it underscored a lasting truth: in regulated industries, survival often depends on collaboration—even among competitors.

Levine’s next venture, Draft, leaned into mobile-first design and a more social, simplified fantasy format. It scaled quickly, and in 2017 was acquired by Flutter (then Paddy Power Betfair) in the largest fantasy exit at the time. But when Flutter’s leadership changed, Draft was folded into FanDuel and its vision dissolved.

“The lesson was clear,” Levine said. “When you sell, leadership matters more than promises.”

Underdog: Product above all else

By 2020, Levine was ready for a third act. Along with six teammates from Draft, he launched Underdog, betting that product velocity would matter more than marketing spend.

“At Underdog, we prioritize two things above all else: people and product,” Levine says. “If we can be the best at building product, we’ll build the biggest company in this space.”

That thesis has held. The company grew from niche “Best Ball” contests into one of the fastest-scaling operators in the space, valued at $1.3B just two years after launch. Levine sums up the approach: “Games, not transactions.”

Whereas incumbents imported European-style sportsbooks and leaned on promotions, Underdog built around the rhythms of U.S. fandom—stop-and-go action, player-first culture, March Madness-style brackets.

New frontiers: Women’s sports & prediction markets

Two growth bets stand out. First, women’s sports: Underdog reports WNBA entries were up ~4x year-over-year, with activity spiking when Caitlin Clark plays. It’s a sign that women’s sports are becoming a mainstream driver of engagement, not just an add-on.

Second, prediction markets: Underdog recently partnered with Crypto.com to let fans back teams as well as players, pushing into territory few operators have touched—and doing so through a federally regulated fantasy framework.

Guard Dog: Responsible gaming with teeth

Beyond growth, Underdog has tried to lead on responsible gaming. In 2022 it launched Guard Dog, a fund investing in startups building safer-play technologies. One portfolio company, ID Pair, enables self-exclusion across multiple operators, rather than siloed compliance.

“It’s not enough for one company to do the right thing,” Levine said. “We need technology and regulation that work across the whole industry.”

Why it matters: Levine’s journey offers a set of lessons for betting startup founders.

• Resilience matters: rejection and regulatory setbacks are inevitable — keep iterating.

• Product velocity beats promos: incumbents can outspend you on marketing, but not on ideas.

• Regulation is part of the strategy: embrace it, don’t dodge it.

Underdog’s unicorn valuation, bets on women’s sports, push into prediction markets, and investments in responsible gaming all point in the same direction: the next wave of winners in this space won’t just be the biggest spenders, but the builders who adapt fastest.