Jeremy Levine was born into a golden era of sports in Boston. During his childhood in Cambridge, just across the Charles River from Boston, he grew up on the tail end of the Celtics dynasty. But maybe more important, the legendary Red Auerbach was very much still part of the Boston sports landscape.
In 1986, the Celtics won their third NBA title of the Larry Bird era, probably with one of the team’s greatest lineups of all time. Led by Auerbach, the Celtics were a dynasty that won 16 titles when he was a head coach, general manager or team president. Auerbach’s leadership style was based on team culture focused around teamwork and discipline. He had an eye for talent as well – 10 players from Aurerbach’s teams are hall of famers.
Levine, an energetic, 38-year-old serial entrepreneur and leader of Underdog Fantasy, brings a passion for people to the office every day. It’s not an in-your-face quality, but more the undying belief in doing things the right way. Underdog Fantasy, a daily fantasy sports platform that offers a variety of betting games, including Pick’em, Best Ball, and Battle Royale, was valued at $484 million in 2022.
As of October 2024, the company had more than 2.4 million active users, with most of the growth coming in states without sports betting like California and Texas.
The site, launched in 2020, has a wide range of investors, including former Dallas Mavericks owner Mark Cuban, Phoenix Suns forward Kevin Durant and Detroit Lions quarterback Jared Goff. The site and app are currently live in 31 states. Underdog Sports, the company’s wagering offering, is live in North Carolina and is licensed, but not live, in Ohio.
People and product are the mantra
For Levine, one of three founders of the site, Underdog is about more than creating a place where fans can place bets or participate in fantasy sports. It’s the focus of a continuous evolution, a learning process to be the best leader he can be.
“My company is probably very sick of me saying this, because I try to say it over and over again, but the two things we focus on are people and product,” he says.
“That’s where I try to spend as much of my time. I view my job as being the lead recruiter for the company. It’s my job to make sure we always have the best people at the company. … I think the thing I’m most proud of recently is the list of people who have chosen to join Underdog. It’s a lot of people with a lot of knowledge and experience in this space who really know the landscape and are making very educated decisions to join the company.”
In recent years, Levine has recruited engineers from DraftKings, executives from FanDuel, and the COO of PointsBet North America. “Universally, I’ve probably had 30 of these recruiting calls over the last nine months where it’s someone ready to make that decision (to join Underdog), and I’m that final call, and all but one of them have chosen to come to Underdog,” he says.
Evolving as a Leader
While many CEOs in the tech, iGaming or gambling spheres have profits and scalability at top of mind, Levine said he has another focus: People and product. In that order.
“I think one of Jeremy’s superpowers is that he identifies people’s strengths and weaknesses really well,” says Peter Jennings, a friend and co-founder of The Solver and board member of Unabated Sports. “I think as an entrepreneur he has this relentless optimism. And I think he inspires people to execute on their superpower, to go after the grand vision that he has. I think that just resonates, and people love being around him.”
One of the people who made that decision is Stacie Stern. Stern, the senior vice president of government affairs and partnerships at Underdog, first met Levine when he was fresh out of college and attended an industry association event in 2012.
“He was this young, vibrant, energetic, kind of whiz kid who had an idea for a fantasy game that was a stock market of sports,” Stern says. “This was really in the infancy of the daily fantasy sports boom, when FanDuel and DraftKings were kind of getting their feet wet.
“What struck me from that very first time I met him was how driven and energetic he was. You could just tell. One of my best friends in the industry, who’s been around since the inception of this association, said ‘Man, there was something special about Jeremy.’ There was something unique about Jeremy.”
Stern says they talked about his idea for what became StarStreet, but came away more impressed with the energy Levine brought to the discussion and the way he went about meeting people and listening to their advice.
“He was maybe 22 years old, but I was really impressed with his ability to listen and ask questions instead of coming in and acting like, ‘Oh, I’ve got the next big thing. And let me tell you how smart I am and how great I am,’ which we saw a lot of in the 2012 to 2014 daily fantasy sports boom,” she says.
Failure an Opportunity to Learn and Improve
Levine’s focus on soaking up information and using that to the best of his ability comes naturally. His parents modeled it for him at an early age. An only child, Levine saw first hand how passion for work can merge with the personal.
“My dad is still a criminal defense attorney. He just loves to work,” Levine says. “He refuses to retire. I remember when we were on a family vacation and he’s got the yellow legal pad out, sitting on the Spanish Steps in Rome, writing all day. He just loves to work in the same way.”
While it is fun when you are winning, it isn’t all sunshine and kittens for Levine. There have been failures as well. That first entry into the field, StarStreet, didn’t survive. But that failure was also a learning experience.
“I certainly learned by doing,” Levine said. “I don’t have any classical training on any of the things I do, but you just try to learn.”
Call Him ‘Unpredictably Rational’
But much like how Auerbach wasn’t born a great coach or manager, Levine learned by observing and listening to others. Described by a friend as “unpredictably rational,” Levine, like Auerbach, is a motivator in addition to having a bright business mind.
“I was perfectly happy at FanDuel when Jeremy approached me,” Stern says. “’I want you to come in and build out a government affairs department and work with me. I want to work with you,’ he said to me.
“But as I had watched him grow, I thought, ‘He’s doing things the right way. He treats people well, and I think he could be on to something.’”
That growth and care for people has earned Levine and Underdog recognition in the business community. LinkedIn named Underdog its No. 15 top startup emerging companies recently, citing the investment in GuardDog, the fund designed to support and scale innovation in responsible gaming.
And for the second year in a row, Goldman Sachs recognized Levine as one of the Most Exceptional Entrepreneurs of 2024 at its Builders and Innovators Summit in October.
Building relationships a successful model
The accolades are nice, but more like icing on the cake. Levine’s goal is to recruit talented people and then play to their strengths.
“I think the thing I’m proudest of recently is to look at the list of people who have chosen to join Underdog, and it’s a lot of people with a lot of knowledge and a lot of experience in this space who really know the landscape and are making very educated decisions,” he says.
“I’ve always stayed true to myself and always put people first. We don’t believe in non-compete (deals) at the company. It’s a company’s responsibility to be the best place for an individual, and if it’s not the best place for them, they shouldn’t be here, right?
“That’s something where just continuing to treat people the right way, like with Underdog, how much that’s paid us back, where people have trust and have faith. It’s part of the reason we’re able to get so many people from all these companies, because I’ve spent 15 years now building these relationships.”
