The Successful Gamble that Paid Off for Gambling.com’s Founder

Charles Gillespie, the founder and CEO of Gambling.com Group, took a big gamble that paid off in a big way. Starting his entrepreneurial journey with a risky bet, Gillespie now leads the world’s leading online gambling affiliate network with over 50 media sites under its belt.

Describing his decision as “almost beautifully stupid,” Gillespie’s risk-taking attitude has led to tremendous success. Gambling.com Group operates as a performance marketing company, driving high-value traffic to its clients in the online gambling industry. Gillespie emphasizes the importance of connecting customers to the best options that fit their needs, much like hotels.com does for accommodations.

Before diving into the online gambling world, Gillespie was a skilled online poker player, using his expertise to build his first affiliate site in 2003. Despite facing challenges with US regulations, Gillespie persevered and eventually found success in the UK market. When the US legalized online gambling in 2018, Gillespie pivoted his focus back to his home country, leading to significant revenue growth.

Today, Gambling.com Group generates $108 million in total revenue, with the US market accounting for $60 million. Gillespie’s journey from a college dorm room to a publicly traded company in the online gambling industry serves as a testament to the power of taking risks and betting on oneself.

Reflecting on his entrepreneurial journey, Gillespie acknowledges the naivety and recklessness of some of his early decisions but emphasizes the valuable lesson he learned: the best bet you can make is one on yourself.