In this edition of Breakfast with NEXT, Yolo Entertainment CEO Matthew D’Emanuele talks about the company’s evolving identity, its expansion plans, and the tough decision to exit Brazil.
Matthew D’Emanuele doesn’t mince words. As CEO of Yolo Entertainment, he’s spent the past 15 months leading the company through an intense transformation — one that’s forcing the fast-moving gaming business to rethink how it scales.
“We’ve always worked at speed, but sometimes we’ve mistaken fast for chaotic,” he admits.
“Now, it’s about making sure our execution is part of a clear roadmap — where every team member understands their role in that bigger picture.”
The company, founded by Tim Heath, undertook a strategic overhaul in 2023 which involved the creation of three key divisions: Yolo Entertainment, Yolo Platform and Yolo Investments.
As part of the restructure, Yolo hired D’Emanuele to the new position of CEO of Yolo Entertainment.
Career so far
D’Emanuele isn’t your typical iGaming CEO. He has worked in senior roles across industries — from automotive to investments to gaming.
One of his earliest roles involved selling cars online. “At the time, I remember thinking, ‘Who would buy a car online without seeing it first?’” he recalls. “This was back in 2001. When I joined, we were selling around 13 or 14 cars a month. When I left five years later, we were selling around 600 a month.”
Later on, he moved from the UK to Oman to join a major conglomerate that juggled automotive, oil, gas, hotels, and top-tier brands like Bose and Tiffany’s.
“It was a really, really big learning curve. It was really exciting, interesting working with those brands in a very new market,” he recalls.
He then transitioned into investments as chief operations officer for Oxford International Financial Holdings, relocating to Malta — a familiar destination he had frequently visited due to family ties.
He left the business in 2016. A non-compete led him to iGaming, where he first joined GiG and later became CEO of Eastrock Group, a B2B company specialised in casino brands in Asia.
By 2023, ready for a new challenge, a call from Heath changed everything. Three months later, he was CEO of Yolo Entertainment, driving its next phase of growth.
Scaling Yolo Entertainment
Yolo Entertainment — home to Sportsbet.io, Bitcasino.io, and affiliate business Partners.io — has grown to around 250 employees spread across Estonia, the Isle of Man, Guernsey, Australia, Spain, and the UK.
But D’Emanuele is focused on more than just expansion; he’s determined to build a sustainable business.
“It’s been a lot of work understanding where we are, what we’re trying to achieve, and what our DNA is now,” he says.
A key focus is expanding Yolo’s regulated market presence. “We’re looking at securing four new licences over the next 10 to 12 months. It depends on regulators, but we’re in a strong position to move quickly.”
While details are still being finalised, he confirms that Ontario and key European and Southeast Asian markets are on the radar.
“Scaling into new markets requires infrastructure, and that’s where we’re investing. Regulation is a core part of our strategy — it’s about gaining expertise and operating freely in key jurisdictions.”
The Brazil exit
One of Yolo’s recent decisions was exiting the Brazilian market.
“We spent a lot of time analysing the market’s potential. We had success, even started the licensing process, but when we looked deeper at the marketing requirements and competitiveness, we felt there were other opportunities more worthy of our focus,” D’Emanuele explains.
“Some markets offer lower-hanging fruit, and we need to be strategic about where we focus.”
That said, Brazil isn’t off the table forever. “It’s a strong market, and we’ll always have the ability to return when the time is right.”
The iPhone moment
As a crypto-first company, Yolo Entertainment sees digital currencies as more than just a payment method — they’re an integral part of its ecosystem.
“Crypto isn’t mainstream yet, but it’s growing fast,” D’Emanuele says. “Most people now know someone who holds crypto. That’s already a shift in momentum. That awareness is the first hurdle.”
For Yolo, the goal isn’t just to accept crypto but to embed it seamlessly into the user experience.
“Many companies see crypto as a way to reduce payment costs, but we see it as something bigger — removing friction in gaming,” he explains. “We’re investing in technology to integrate crypto deeper into the customer experience, not just as a cashier option.”
D’Emanuele believes mass adoption will take off once a major retailer, like Amazon, fully embraces crypto.
“We’re waiting for that ‘Apple iPhone moment’ — the tipping point where crypto moves from niche to mainstream,” he says. “It’s coming, and we want to be ready.”
Operational discipline
In the meantime, D’Emanuele is on a mission to sharpen Yolo Entertainment’s focus, strengthen its structure, and build a team driven by purpose rather than perks.
His career across multiple industries has shaped his leadership approach, and he firmly rejects the idea that any sector is truly unique.
“Every industry likes to think it’s different, but at the core, they all operate on the same fundamentals — product, service, and talent,” he says.
“Gaming is no exception. Success comes down to optimising processes, having clear policies, and building a team that believes in the vision.”
When he entered the iGaming sector, he saw an industry brimming with potential yet lacking operational discipline.
“At GiG, I joined just after a major acquisition and immediately saw an opportunity to bring more structure and clarity,” he recalls.
“One of the biggest shifts across the customer operations we made was in how we approached hiring. At the time, it was common that people would even choose companies based on the types of perks they offered. I wanted them to choose us because they believed in what we were building”
As he looks ahead, two priorities stand out: confidence and focus.
“As a company, we have everything we need — our own game studios, content aggregators, odds compilers. We need to recognise our strengths and believe in our potential,” he says.
“At the same time, we must be sharper in our objectives. At the end of each day, we should know whether we’ve had a good day or a bad one.”
“Brilliant at the basics”
With Yolo Entertainment on solid financial footing, D’Emanuele is now focused on reinforcing its performance by fine-tuning internal processes.
“We’ve had a fantastic year financially, but sustained success is about embedding the right behaviours and ensuring new talent brings fresh energy,” he says. “For me, it’s about being brilliant at the basics.”
On a personal level, he’s evolving as a leader, adjusting to the demands of steering a growing company.
“I used to be very hands-on, but as CEO of Yolo Entertainment, I can’t be in every detail,” he admits. “My role now is to ensure our leadership team embodies that same philosophy — fostering communication, aligning strategy, and driving the business forward.”
Learning from the next generation
Away from work, D’Emanuele’s home life — with four children aged between nine and 17 — gives him unique insight into changing consumer behaviours.
“The way my kids consume content is totally different from how we used to,” he says. “They’ll watch hours of short-form videos, absorbing information in bite-sized bursts.”
“It’s something we need to understand better because their expectations will shape the future of our industry.”
D’Emanuele also sees an irony in how gaming is regulated compared to other forms of digital entertainment.
“My nine-year-old son could spend €500 on loot boxes in a day — we obviously don’t let him — yet our industry faces so much scrutiny,” he notes.
“As much as I try to stay ahead of industry trends, sometimes my kids teach me more in a day — without even realising it — than I could learn in two days of meetings,” D’Emanuele reflects.
Staying curious, whether in business or at home, is the key to staying ahead.
