When Charles Gillespie was 22 years old, he bought a one-way ticket to China. He left America with a laptop, a few lines of code, and the determination needed to build something lasting. It was a move many called reckless, but Gillespie believed in himself and took the risk. Nearly 20 years later, he is wise enough to realize just how big that risk was, but successful enough to prove that betting on yourself isn’t a bad idea.
Gillespie boarded the flight after the Unlawful Internet Gambling Enforcement Act of 2006 brought the online gambling website he was working on to a halt. Moving to China, Gillespie had to learn fast. There, he founded the Gambling.com Group.
Gillespie still serves as the company CEO and has overseen the company from its days as a ballsy startup through going public on the NASDAQ exchange in July 2021. Gillespie’s ascent in the online gambling world is a testament to resilience, embracing calculated risks, and prioritizing the end user.
Building From Scratch in the World’s Most Competitive Market
Gillespie grew up in North Carolina and was a self-described “geek” from an early age. He started building websites in his spare time. Exposure to the web led Gillespie to discover online gambling, specifically poker. The game not only inspired Gillespie on his entrepreneurial journey but also served as his main source of income for a few years. However, it wasn’t long before his entrepreneurial spirit led him to start building his own gambling website.
After the US clamped down on online gambling, Gillespie decided to emigrate and take on the next biggest gambling market in the world. After settling in China, Gillespie hired 25 other people, and together they built a multi-million-dollar company.
Cutting his teeth as a foreign entrepreneur in China was a baptism of fire for Gillespie, who found himself in one of the most competitive and unfriendly business environments in the world. During one meeting, an investor warned Gillespie that Chinese capitalists would not take kindly to an American in their market. However, his time spent in China taught Gillespie the discipline and focus that he needed to excel in his career.
The Pivot That Changed Everything
Gillespie made the conscious decision to point his early focus towards the UK market. For years, this plan worked, and Gillespie continued to build and grow his business. However, the gambling industry was evolving, and it was clear that the future of online gambling lay in the US.
This required a significant change in the Gambling.com Group, as its holding company was based in Malta. No Maltese company had ever gone public in the US. So, Gillespie packed up and moved the group’s holding company to Jersey, in the Channel Islands. While this was not a straightforward affair, it was a move that proved to be exactly what Gillespie needed to take the next step on his entrepreneurial journey.
The Road to NASDAQ
Entering the American market meant making the push to go public. Gillespie has made no attempts to hide the fact that the IPO process was expensive and incredibly tedious. However, on July 23, 2021, the Gambling.com Group started trading on the NASDAQ Global Market. In doing so, it became the first online gambling company to become publicly traded in the United States.
Another thing that sets Gambling.com Group apart from its competitors is that it was not bought. Rather, it was built from the ground up by Gillespie and his team. This is an important consideration as it means the company was built with organic reach and strategic purposes rather than being the result of a high-cost acquisition strategy.
Strategic Growth Through Smart Acquisitions
Organic growth was the cornerstone of Gillespie’s business strategy at the Gambling.com Group. However, always bold and willing to trust his instincts, he has also proven adept at identifying strategic acquisitions to help the company grow. In January 2022, the group acquired RotoWire, a fantasy sports platform, for $27.5 million. This was followed the next month by the $69 million acquisition of BonusFinder.
The most notable acquisition was made later that same year when the Gambling.com Group purchased the domain for Casinos.com, where it joined a growing list of sites that included Gambling.com, Bookmakers.com, and Bookies.com. The site was rebuilt and launched in July 2023, marking the first time the domain had been active since its registration in 1994.
Gillespie’s success is not just down to his investment acumen, but also his belief in the customer experience.
A User-First Philosophy That Builds Loyalty
Throughout his career, Gillespie has never stopped operating on a user-first philosophy. He uses his platforms to connect customers with the best local options that suit their needs at any given time. The Gambling.com Group operates similarly to Hotels.com, where gambling site operators pay a commission for customer referrals. However, Gillespie understands that sustained success is about quality over quantity.
The intent is to direct customers to a site where they can place a bet immediately. This is certainly obvious on Casinos.com, which aims to connect players with sites that offer the fewest entry barriers. Entry points like sites offering top-rated no-deposit deals ensure new users are instantly encouraged to create an account and explore the site without any immediate financial risk.
Gillespie’s commitment to the customer-first mentality not only created a more transparent and trustworthy model but also gave the Gambling.com Group a significant competitive advantage in a niche where trust is pivotal.
Lessons From the Trenches
Much of Charles Gillespie’s success can be traced back to one key moment: the decision to move and chase down his vision. He backed himself, and while he freely admits he was naïve and reckless, those traits also taught him that to be successful you need to believe in yourself because nobody is going to do it for you. Gillespie has grown his company to global prominence and rightly earned the Sports Betting Community Leader of the Year in 2019.
Growing a company from a small startup in China to ringing the NASDAQ bell takes resilience and adaptability. It also shows that it is possible to build a successful business with a strong user-first foundation. However, Gillespie was also willing to pivot when necessary, showing how vital it is for companies to avoid getting bogged down with a tunnel-vision-driven approach.
For entrepreneurs waiting for the right moment to take the next step, Gillespie’s story has a clear message: be bold. Take calculated risks and never forget that user value is priceless. Most importantly, if you wait for the right time, it might never arrive. Believe in yourself and your ability to succeed.
