【Cheese Touch game crossed fingers】NYC 2025: Odds Holdings CEO Matt Restivo on failed M&A and the stress of a $160m deal

When Gambling.com Group announced its acquisition of Odds Holdings — the parent company of OddsJam — last December, it marked the culmination of a long and, at times, challenging M&A process.

However the final deal, valued at up to $160m, closed at breakneck pace, completing in just 60 days by 1 January.

Speaking at the NEXT Summit New York 2025, Restivo shared insights on the highs and lows of building a business, failed mergers, and the immense stress that accompanied the eventual sale.

The trials of failed M&A

Before landing in the Gambling.com portfolio, Odds Holdings endured multiple failed M&A attempts — each one taking a toll on both the business and its leadership.

“We walked away from one process, and another one didn’t end favourably for us,” Restivo recalled, adding that the complexities of selling the company while maintaining its operational efficiency proved to be one of the toughest challenges.

“I think it’s very hard to run an M&A process and your business at the same time. You’re either operating it, or you’re selling it — you can’t do both,” he said.

“The first time we went through a sale process, we got incredibly distracted. We took our eye off the ball. And you’d think we’d learn our lesson — but each time we emerged from a failed deal, we realised we didn’t have as tight a grasp on the business as we should have.”

Restivo likens the process to capital raising in start-ups.

“In early-stage start-ups, you typically have a CEO responsible for securing capital while everyone else focuses on building and operating the business. The same principle applies to M&A.”

Who fits our DNA?

Restivo explained that the company’s executive team — founders Ankit Goyal and Alex Monahan, Restivo himself and a few key colleagues — had identified early on that “there was going to be more synergy recognised from a third party owning and operating this business over time than we could sort of bootstrap our way to.

“We had decided that we didn’t want to take outside capital. We just wanted to bootstrap, and that really puts a ceiling on how hard you can go at things,” Restivo said.

So, in late 2023 and early 2024, the company set out to find a banking partner.

“We found a banking partner we really liked, but the process took three months just to prepare our materials,” Restivo said. “That forced us to analyse our business at a granular level.”

“Then came another three months of meetings, flying around the world, trying to determine the right long-term partner.

“We built relationships with many people — some who would have been great buyers and others who wouldn’t have been the right fit.

“But it really took a long time to understand who fits our DNA,” he said.

The stress of closing the deal

When Gambling.com stepped in, the process moved at lightning speed.

“They’re elite at M&A,” Restivo said. “They were on us, on our bankers, pushing everything forward. I think I lost 10 pounds in December alone, being awake from 7am to 11pm, locked in the office.”

The sheer pace of the deal added another layer of intensity, while the fact that Gambling.com Group is a public company meant it wasn’t just about negotiating numbers — it was deep due diligence, structuring terms, legal work, and ensuring everything was aligned for a public company acquisition.

Despite the pressure, the deal closed successfully. In just two months, they signed an LOI, announced the deal to the public markets, and finalised the transaction.

Life after the acquisition

Now under the umbrella of a publicly traded company, Odds Holdings faces new challenges and opportunities.

“It’s a multi-year partnership, and we’re very mindful of their needs,” Restivo said. “In a private company, you don’t answer to anyone. You just build. But now, about 10% of our time is allocated to corporate processes.”

Being part of a larger entity means navigating new structures and expectations.

At the same time, Gambling.com Group brings synergies and resources the business didn’t have before.

Despite the changes, the team remains focused. “This was a sales big event, and it got a lot of attention. But at the end of the day, we have to put our heads down and execute at the same pace we have for the past two years.

“It took a few cycles to get everyone back into that intensity, but now, we’re finding our stride.”