Chris Bevilacqua from Simplebet on taking risks and making odds

When sports industry executive Chris Bevilacqua founded his sports betting company, Simple bet, in 2018, he wasn’t concerned that a pair of high rollers known as DraftKings and FanDuel could run the table. “If you want to be an businessroundups.org, the most important quality is that you can’t be afraid of failure,” he says. “It never occurred to me that I would.”

Five years later, Bevilacqua’s risk appetite has catapulted the company into a major player with a unique twist: microbetting. 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, such as who will win or how many points will be scored, Simplebet allows fans to bet on individual games in real time. Users can place bets on whether a field goal will be good seconds before it is kicked, or whether a basketball player will shoot a three-pointer on the next possession. While Bevilacqua has never been a gambler in the traditional, Vegas-esque sense, he sees great potential for success in the gamification of live sporting events.

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“Everyone 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 field, and it’s going to be over 97 mph,'” he says. “Not everyone bets on sports, but everyone has an opinion on what’s going to happen. That’s where you get the mass market opportunity.”

With raised equity of $80 million, investors are betting big on Simplebet. Given his track record, that’s no surprise. In 2001, the former nationally ranked college wrestler founded College Sports TV, the first-ever 24-hour college sports network. In addition to being a co-founder of Simplebet, Bevilacqua is the CEO and co-founder of the media and commercial rights company Bevilacqua Helfant Ventures and a prominent figure in the sports and media industry.

An unexpected business trip begins

In 1986, just a year into 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 his senior year. After graduating from Penn State with a BS in marketing and a twice-reconstructed shoulder, Bevilacqua didn’t know what to do with his life. All he knew was that he wanted to work in sports. Bevilacqua asked around and eventually found a friend of a friend who knew Gray Seamans, an executive at NBC Sports. He met Seamans at New York’s iconic 30 Rock Building and soon landed his first freelance job on NBC’s video production team, helping to create weekly promos for NBA and NFL games.

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Bevilacqua stayed with NBC for several years and, ironically, ended up working as an associate producer on the 1988 Olympics he had originally wanted to participate in, winning an Emmy Award for Best Live Special in the process. It wasn’t the award he set out to win, but it was a catalyst that accelerated his career. In the mid-1990s, he worked for Major League Baseball, where he “learned how to sell.” One of his clients was Nike, where he was eventually hired as Global Negotiations Director. “During all that, I was building relationships and learning how the sports business ecosystem worked,” he recalls. His on-the-job training paid off. He spearheaded the company’s college sports marketing campaign, helped transform Nike into the dominant footwear and apparel brand for college 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 took his idea to Nike and was promptly rejected. “They told me they don’t sell TV — they sell shoes and clothes,” Bevilacqua recalls. “That was the moment I decided to become an businessroundups.org.” He quit his job at Nike, taught himself PowerPoint and wrote a business plan for what eventually 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 then about everything that can go wrong,” he recalls. “But looking back, I’m glad it never occurred to me that I would fail. Usually, in business and in life, if you’re not afraid of failure, and you’re not outcompeted, you’ll get there as the best.”

Of course, Bevilacqua recognizes that every businessroundups.org will fail in one way or another. As a friend told him early in his career, “Being an businessroundups.org means you have some of the best days of your life, and some of the worst days. And sometimes it will be the same day.” Expecting perfection, he believes, is an obligation – an attitude he also brings to the negotiating table. “Negotiation is give and take,” he says. “Both sides must be a bit unhappy with the final 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, is being promoted by Sports video group, and the company’s own app, Playbook, is now available for both iOS and Android. Despite all the success, Bevilacqua remains humble. “I’m never the smartest person in the room at my business meetings,” he says, “but I do know how to build a business.” Asked to explain, 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, let me 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 businessroundups.org, I have to find really smart people and coach them. And then they coach the people around them.”