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Kumar.com Founder and CEO of the Group Charles Gillespie started his entrepreneurial journey in the most appropriate way possible. With a big bet. Eighteen years later, Gillespie describes his decision as “almost too stupid,” but it's hard to deny that his gamble paid off.
The Gambling.com Group is the world's leading online gambling affiliate network, with a portfolio of over 50 media sites offering gambling-related content and instant links to online casinos. Gillespie compares his business model to hotels.com in that both services connect customers with the best local options to suit their needs, whether that means a bed or a baccarat table. “We get paid by online gambling companies for referring new customers to them,” explains Gillespie.
At its core, Gambling.com Group is a performance marketing company. It aims to drive what Gillespie calls “high-value traffic” to her customers. In the online gambling industry, high value traffic means more than just bringing in high reels; it also depends on the customers looking to bet instantly.
“It's about aiming high,” says Gillespie. “People looking for things like the best sportsbook promotions, the best online sportsbooks, things that really show the intent for that user to understand not only what options are out there, but what's the best for their circumstances.”
Before he became a major player in online gambling, Gillespie was a major player. Raised in North Carolina, the self-described “geek” spent his youth building websites and eventually bumped into some people with a penchant for online poker. In time, Gillespie and his friends became quite good at the game; at one point, poker became his main source of income for several years.
After launching his first gambling affiliate site in 2003, Gillespie decided to push all his chips into the industry. He started working on his company in 2006 from his dorm room in Ruffin Hall 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 opportunities for a domestic gambling industry in the United States.
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Despite the bad shot, Gillespie didn't flinch. Instead, he tried to achieve 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 who want to gamble.” The 22-year-old postgraduate made his biggest bet yet, booking a one-way flight to China with nothing more than a few lines of computer code and a dream. Upon arrival, Gillespie hired 25 people to help him and his co-founder build what became a multimillion-page sports betting content website.
“Starting our career in China taught us to learn quickly,” says Gillespie. “We cut our teeth in one of the most competitive business environments imaginable.” He recalls meeting a prominent investor early in his time in China, where the investor told him, “These people make American capitalists look like amateurs. They are infinitely more capitalistic and aggressive than any competition in the United States.” According to Gillespie, he was right. The tough business environment taught the new CEO to narrow his focus. “If you chase too many rabbits in at the same time, you won't catch any of them,” he said.
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After getting the company off the ground, Gillespie set his sights on the UK, the world's largest properly regulated online gambling market. He moved away from sports betting and towards online casino games. “We got all into the UK market and that's when our fortunes started to change. We got some traction, started making significant money and also got the opportunity to buy the gambling.com domain name in 2011,” said Gillespie.
By then, Gillespie had given up on the United States figuring out how to regulate online gambling. He had moved on to greener, less clogged 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 situation around.” And they returned. Shunning serious consideration of a European IPO, Gillespie committed to bringing his company back to the United States, even if he had to wait a few years. Today, the US accounts for most of the total revenue of $108 million, accounting for $60 million. According to Gillespie, Gambling.com Group is the only publicly traded online gambling affiliate in the US that was built, not bought. In retrospect, Gillespie looks back at some of his early days The Risks as naive and reckless. However, these risks taught him a valuable lesson that resonates with any entrepreneur: the best bet you can make is one on yourself.