How a Big Bet Paid Off for’s Founder


Opinions expressed by Entrepreneur contributors are their own. Group founder and CEO Charles Gillespie started his entrepreneurial journey in the most fitting way possible. With a big bet. Eighteen years later, Gillespie describes his decision as “almost beautifully stupid,” but it’s hard to deny that his gamble paid off. Group is the world’s leading online gambling affiliate network, with a portfolio of over 50 media sites offering gambling-related content and instant connection to online casinos. Gillespie likens his business model to in that both services connect customers to the best local options to fit their needs, whether that means a bed or a baccarat table. “We get paid by the online gambling companies for referring new customers to them,” Gillespie explains.

At its core, Group is a performance marketing company. It aims to drive what Gillespie calls “high-value traffic” to its clients. In the online gambling industry, high-value traffic means more than just bringing in high rollers; it also depends on customers looking to wager immediately.

Related: ‘Every Billionaire Wants a Casino.’ Jay-Z Is Trying to Open a Caesars Palace in the Heart of Times Square.

“It’s all about high intent,” Gillespie says. “People searching things like best sports book promos, best online sportsbooks, things that really show intent for that user to understand not only what options are out there, but which one is best for their circumstances.”

Before becoming a major proprietor in online gambling, Gillespie was a major player. Growing up in North Carolina, the self-described “geek” spent his youth building websites and eventually stumbled across some people with a penchant for online poker. Over time, Gillespie and his friends got pretty good at the game; at one point, poker became his primary source of income for a few years.

After starting his first online gambling affiliate site in 2003, Gillespie decided to push all his chips into the industry. He began working on his company in 2006, out of his Ruffin Hall dorm room at UNC a la Mark Zuckerberg, writing lines of code between classes. Unfortunately for him, the US government was less keen on the concept of legalized online gambling. Congress passed the Unlawful Internet Gambling Enforcement Act in late 2006, which Gillespie blames for killing early chances of a homegrown online gambling industry in the States.

Related: ‘It Never Crossed My Mind That I Would Fail’: Chris Bevilacqua on the Launch of Simplebet

Despite the bad beat, Gillespie didn’t fold. Instead, he went all in on achieving his dream. “We didn’t have a lot of money, and we couldn’t do it in the U.S.,” Gillespie said. “So we decided to go to the next biggest market in the world full of people that love to gamble.” The 22-year-old post-grad made his biggest bet on himself yet, booking a one-way flight to China with nothing but some lines of computer code and a dream. Upon arrival, Gillespie hired 25 people to help him and his co-founder build what became a million-page sports betting content website.

“Starting our career in China taught us to learn fast,” Gillespie says. “We cut our teeth in one of the most competitive business environments imaginable.” He recalls meeting with a prominent investor early in his time in China, where the investor told him, ‘These people make American capitalists look amateurs. They are infinitely more capitalist and aggressive than any competition in the States.” According to Gillespie, he was right. The cutthroat business environment taught the young CEO to narrow his focus. “If you chase too many rabbits at once, you won’t catch any of them,” he said.

Related: The History of Online Gambling (Infographic)

After getting the company off the ground, Gillespie set his sights on the UK, the world’s largest properly regulated online gambling market. He pivoted away from sports betting and toward online casino games. “We went all in on the UK market, and that’s when our fortunes started to change. We got some traction, started making meaningful money, and also got the opportunity to buy the domain name in 2011,” Gillespie said.

By then, Gillespie had given up on the US figuring out how to regulate online gambling. He had moved on to greener, less gridlocked pastures. So, when the Supreme Court ruled in favor of online gambling in 2018, Gillespie was caught off guard. “We were focused on the UK, Ireland, European markets,” Gillespie said. “So we had to turn the whole thing around.” And turn around they did. Pivoting from seriously considering a European IPO, Gillespie committed to returning his company to the States, even if he had to wait a few years. Today, the US makes up most of its $108 million total revenue, accounting for $60 million. According to Gillespie, Group is the only publicly traded online gambling affiliate company in the US that was built rather than bought. In hindsight, Gillespie views some of his early risks as naive and reckless. However, these risks taught him a valuable lesson that resonates with every entrepreneur: the best bet you can make is one on yourself.

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