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Gambling.com Group Founder and CEO Charles Gillespie began his entrepreneurial journey in the most fitting way possible. With a big bet. Eighteen years later, Gillespie describes his decision as “almost pretty stupid,” but there’s little denying that his gamble was worth it.
Gambling.com Group is the world’s leading online gambling affiliate network with a portfolio of over 50 media sites providing gambling-related content and an instant connection to online casinos. Gillespie compares his business model to Hotels.com because both services connect customers with the best local options that fit their needs, be it a bed or a baccarat table. “We are paid by the online gambling companies to refer them new customers,” explains Gillespie.
At its core, Gambling.com Group is a performance marketing company. The goal is to provide its customers with what Gillespie calls “high-quality traffic.” In the online gambling industry, quality traffic means more than just attracting high rollers; It also depends on the fact that customers want to bet immediately.
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“It’s about high intentions,” Gillespie says. “People are looking for things like the best sports betting promotions, the best online sportsbooks, things that really show the intent of the user to understand not only what options are out there, but which one is best for their circumstances. “
Before Gillespie became a major online gambling operator, he was one of the key players. Growing up in North Carolina, the self-proclaimed “geek” spent his youth building websites and eventually came across some people who had a penchant for online poker. Over time, Gillespie and his friends became pretty good at the game; At some point, poker became his main source of income for a few years.
After Gillespie opened his first online gambling affiliate website in 2003, he decided to put all his chips into the industry. He began working on his company in 2006 in his dorm room in Ruffin Hall at UNC, à la Mark Zuckerberg, writing lines of code between classes. Unfortunately for him, the US government was less interested in the concept of legalized online gambling. Congress passed the Illegal Internet Gambling Enforcement Act in late 2006, which Gillespie blames for destroying the early chances of a domestic online gambling industry in the United States.
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Despite the bad beat, Gillespie didn’t give up. Instead, he did everything he could to make his dream come true. “We didn’t have a lot of money and we couldn’t make it in the U.S.,” Gillespie said. “So we decided to go to the next biggest market in the world, which is full of people who love to gamble.” The 22-year-old postgraduate made his biggest bet yet on himself, booking a one-way flight to China with nothing but a few lines of computer code and a dream. Upon his arrival, Gillespie hired 25 people to help him and his co-founder build a million-page sports betting content website.
“Starting our careers in China taught us to learn quickly,” says Gillespie. “We have made a name for ourselves in one of the most competitive business environments imaginable.” He recalls a meeting with a prominent investor early in his time in China, in which the investor told him: “These people leave American ones “Capitalists look like amateurs.” They are infinitely more capitalist and more 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 do it.” “Catch one of them,” he said.
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After founding the company, Gillespie set his sights on the UK, the world’s largest properly regulated online gambling market. He turned away from sports betting and towards online casino games. “We went all in on the UK market and that’s when our fortunes started to change. We got some traction, made a lot of money and also got the opportunity to buy the domain name Gambling.com in 2011,” Gillespie said.
By this point, Gillespie had already given up seeking regulation of online gambling in the United States. He had moved on to greener, less deadlocked pastures. When the Supreme Court ruled in favor of online gambling in 2018, Gillespie was surprised. “We have focused on the UK, Irish and European markets,” Gillespie said. “So we had to turn the whole thing around.” And they turned around. After seriously considering an IPO in Europe, Gillespie committed to returning his company to the U.S., even if he had to wait a few years. Today, the US generates the largest share of its total revenue of $108 million, at $60 million. Gillespie said Gambling.com Group is the only publicly traded online gambling affiliate in the U.S. that was built rather than purchased. In retrospect, Gillespie sees 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 on yourself.