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When veteran sports industry executive Chris Bevilacqua launched his sports betting company, Simplebet, back in 2018, he wasn’t worried that a couple of high rollers known as DraftKings and FanDuel might run the table. “If you want to be an entrepreneur, the single most important attribute is you can’t be afraid to fail,” he says. “It never once crossed my mind that I would.”
Five years later, Bevilacqua’s risk-on attitude has catapulted the company into a major player with a unique twist: micro-betting. Simplebet, originally a business-to-business product development company, launched its own free-to-play app called Playbook in 2021. Instead of betting on the usual outcomes, like who will win or how many points will be scored, Simplebet allows fans to wager on individual plays in real time. Users can place bets on whether a field goal will be good just seconds before it is kicked, or if a basketball player is going to shoot a three-pointer during the next possession. Though Bevilacqua has never been a gambling man in the traditional, Vegas-y sense, he sees great odds of success in the gamification of live sporting events.
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“Everybody likes to watch a game with their friends and be the one who says, ‘I know Garret Cole is going to throw a fastball on this pitch, and it’s going to be over 97 mph,'” he says. “Not everybody bets on sports, but everybody has an opinion on what’s going to happen. That’s where you get the mass market opportunity.”
With $80 million raised in equity capital, investors are betting big on Simplebet. Given his track record, it’s not a surprise. In 2001, the former nationally ranked college wrestler founded College Sports TV, the first-ever 24-hour college sports network. In addition to co-founding Simplebet, Bevilacqua is the CEO and co-founder of media and commercial rights company Bevilacqua Helfant Ventures and a prominent figure in the sports and media industry.
An unexpected business journey begins
In 1986, just one year out of college, Bevilacqua had visions of becoming a professional athlete himself. He was a two-time All-American wrestler at Penn State and nearly competed in the 1988 Olympics. Unfortunately, his Olympic dreams were shattered by a shoulder injury in his senior year. After graduating from Penn State with a BS in marketing and a twice-reconstructed shoulder, Bevilacqua was unsure of what to do with his life. The one thing he knew was that he wanted to work in sports. Bevilacqua asked around and eventually found a friend of a friend who knew Grey Seamans, an executive at NBC Sports. He met Seamans at the iconic 30 Rock Building in New York, and soon scored his first freelance job with NBC’s video production team, helping to make weekly promos for NBA and NFL games.
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Bevilacqua continued at NBC for several years, and, ironically, ended up working as an associate producer at the 1988 Olympics he had originally intended to compete in, and winning an Emmy Award for best live special in the process. It wasn’t the award he had planned on winning, but it was a catalyst that fast-tracked his career. By the mid-’90s, he was working at Major League Baseball, where he “learned how to sell.” One of his clients was Nike, where he was eventually hired as the Global Negotiations Director. “Throughout all of that, I was making relationships, and learning the entirety of how the sports business ecosystem worked,” he recalls. His on-the-job education paid off. Leading the company’s college sports marketing campaign, he helped transform Nike into the dominant footwear and apparel brand for university teams and even bought the rights to put Nike’s swoosh on NCAA athletic uniforms.
Taking the entrepreneurial leap
Building on his momentum, the time was right to pitch his next big idea: A 24-hour college sports TV network. He went to Nike with his idea and was promptly rejected. “They told me they don’t sell TV — they sell shoes and clothes,” Bevilacqua remembers. “That was the moment I decided to become an entrepreneur.” He resigned from Nike, taught himself PowerPoint, and wrote up a business plan for what ultimately became College Sports Television.
Quitting your high-level position at an industry behemoth is a risky move. But Bevilacqua, in case you hadn’t noticed, embraces risk. He credits playing sports for helping build his admittedly irrational confidence and competitive fire. Not to mention blissful ignorance. “There was a lot I didn’t know back then about everything that can go wrong,” he recalls. “Looking back, though, I’m glad it never crossed my mind that I’d fail. Most of the time, in business and in life, if you’re not afraid to fail, and you don’t get outcompeted, you come out on top.”
Of course, Bevilacqua acknowledges that every entrepreneur is bound to experience failure in some form. As a friend told him early in his career, “Being an entrepreneur means having some of the best days of your life, and some of the worst days. And sometimes it’s going to be the same day.” Expecting perfection, he believes, is a liability—an attitude he brings to the negotiating table as well. “A negotiation is a give-and-take,” he says. “Both sides have to be a little unhappy with the ultimate outcome.”
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Simplebet has been well received early on. The ‘Pick-and-Play’ partnership with the Yankee Entertainment and Sports (YES) Network, which allows users to place bets in the YES app while watching a sporting event, has been described as “revolutionary” by Sports Video Group, and the company’s own app, Playbook, is now available on both IOS and Android. Despite all the success, Bevilacqua remains humble. “I’m never, ever, the smartest person in the room during my business meetings,” he says, “but I do know how to build a company.” Asked to elaborate, the former jock recalls a conversation he once had with legendary FSU NCAA football coach Bobby Bowden. At the time, Bowden was the most successful college football coach ever, and Bevilacqua wanted to know his secret. “He said, ‘Chris, lemme tell you something. A lot of people think I coach my players. I don’t. I coach my coaches.'”
Bevilacqua was only about 30 years old at the time, but those words have stuck with him throughout his career. “As an entrepreneur, I’ve got to find really smart people and coach them up. And then they coach up the people around them.”