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In the latest edition of Breakfast with NEXT, Charles Gillespie takes a trip down memory lane.

In conversation with Sonja Lindenberg, he talks domain acquisition strategies and explains why it’s never too late to enter a market.

The $2.5m gamble

It was a Monday morning in April 2011, when Gillespie received the call that would alter the fate of his company forever.

As he answered the phone, he was told that his bid for the gambling.com domain had been accepted – an asset that had once been worth a staggering $20m.

Media Corporation, the UK-based company that previously owned the domain, had struggled to reinvent it for the UK market following the passage of the Unlawful Internet Gambling Enforcement Act in the US.

Consequently, the value of the domain had plummeted, and Media Corp decided to sell it. They set a reserve price of $9m, but were unable to attract a single bid.

“They started calling around the industry to get some bids through. I think they were under great pressure to raise some cash for the business in a fairly short time,” Gillespie recalls.

“They indicated that they would accept a lot less, so we put in a bid for $2.5m. We didn’t exactly have that money lying around. We pulled all the cushions off the sofa and spoke with our major investor to finance it, and that came together very quickly, thankfully.”

“That call was certainly a pivotal moment in the company’s history and my life,” Gillespie reflects.

Just one NDC

Everything happened so quickly, Gillespie didn’t even have a website ready. Luckily, the domain’s previous owners allowed them to use the their old site while Gillespie’s team worked on a new one.

Even with the legacy site up and running, “the first two months yielded only one new depositing customer,” Gillespie laughs.

However, one year later, gambling.com had become the group’s largest website, and in May 2017, the company rebranded from KAX Media to Gambling.com Group.

An end to a long process

Today, Gillespie lives in Monaco. On his office wall are photos from the bell ringing ceremony marking Gambling.com’s IPO on Nasdaq in New York in 2021.

“This was the highlight in our journey so far, and I am a little bit proud of it,” Gillespie says.

He spoke about the challenging IPO process before, which he describes as “really intense and long”.

“It didn’t quite come together exactly the way we had anticipated. The bell ringing ceremony was delayed due to the pandemic, but it put a formal end to the IPO process, and it was a day I will never forget,” he says.

Turning the ship around

Today, the group employs around 450 people, across various offices in the US and Europe.

Its domain gambling.com is still the group’s most important asset. “It continues to surprise us every day how powerful and successful the site is,” Gillespie says.

After acquiring the domain, Gillespie says, the company did everything to make it successful in the UK.

He recalls how first they had “to convince the world and Google that this was a UK website and not a US website”.

When the US market opened in 2018, the group had to change strategy again.

“I used to say that it was an oil tanker, which we had to point back at the US. Thankfully now many years on, it’s succeeding in the US as well, and it’s truly an international site.”

A new domain

The ship that is Gambling.com (to borrow Gillespie’s own analogy) is powering full speed ahead.

In November last year, the group acquired the domain casinos.com from Caesars, and Gillespie already announced that he expects the new domain to surpass the value of gambling.com.

“This is obviously not going to happen overnight,” he clarifies. “However, casinos.com is way more focused than gambling.com.

“It also lends itself more easily to land-based opportunities, which makes it attractive for people looking for such options.

“We have always considered the possibility of expanding into different business models beyond online gambling affiliation, such as travel affiliation, which is a huge industry. While it won’t happen soon, we see a clearer path to growth beyond pure gambling affiliation with casinos.com compared to gambling.com,” he says.

Refusing to lose

According to Gillespie, staying focused is the key to success.

He’s been running his company for 17 years and knows firsthand the danger of trying to do too much at once.

“There were times when we would experiment by going into different markets at the same time, but that’s like throwing a bunch of spaghetti at the wall and seeing what sticks. It doesn’t work.

“I think this is good advice for any entrepreneur, particularly someone who’s just starting up.

“Do the research, figure out which one of those 10 markets is the best opportunity for you and then commit and refuse to lose in that single market. Win each battle before you go on to the next one.”

No rush

What does that mean for the future of gambling.com?

“Everybody’s talking about Latam and wants to move on to the next thing,” he says.

“We are still growing in the UK, the world’s most mature online gambling market, and the US continues to expand at a breakneck pace. So we just look at those two markets. There’s no lack of opportunity or things to do.”

Gillespie recalls that when the company entered the UK in 2009, they had a “real serious conversation” about whether it was too late because other big affiliates had built up a position.

“Now, 12 years later, that’s hilarious. The market has just grown leaps and bounds. It wasn’t easy, but we still managed to break into the UK market.”

“If somebody runs in first and gets a little bit of a leg up and in Brazil, I’m not too bothered about that. It doesn’t necessarily mean there are greater opportunities in less developed markets. You can always enter them later. That seems to work just fine too,” he says.

Opportunity knocks

While Gillespie is willing to take his time to ensure success, he’s also open to seizing unexpected opportunities that come his way.

One such opportunity arose during a board meeting when Gillespie was asked about the best domain that could be added to the group’s portfolio.

“Without hesitation, I said, ‘casinos.com. I think Caesars has got it.’ As luck would have it, my general counsel used to work at Caesars and knew the right people to contact.

“It took some negotiation. There’s always bit of a dance involved, but we got there in the end.”

The right advice

According to Gillespie, he is not competitive in life (“When I play golf, I really don’t care about my score”), but in business, he’s all about the competition.

Looking back, Gillespie expresses gratitude for finding professional investors right at the start of the company’s journey.

They provided invaluable guidance on how to raise money and negotiate deals.

Gillespie, and co-founder Kevin McCrystle, were still very young when they set up the first company – the predecessor of Gambling.com – in 2006.

The duo met in high school and attended university in North Carolina together.

Gillespie credits some of the company’s success to the financing decisions he and McCrystle made early on, with the help of their mentors.

“As entrepreneurs, we needed to protect ourselves and make sure that we maintained enough upside potential to win when we eventually reached the point we are at now, where we are publicly traded and operating at scale.

“If you get diluted too much during the journey, it may no longer be compelling for you.

“We also gained access to kind of a different universe of knowledge, people and connections.

“That has really forced us to think big – and it has paid off,” he concludes.

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