Matthew D'Emanuele is the CEO of Yolo Entertainment, a division of Yolo Group. Yolo Group is the Tallinn-based gaming, fintech, investment, and blockchain innovation firm founded by Australian entrepreneur Timothy John Heath.
With a career spanning multiple industries, Matthew D'Emanuele brings a fresh perspective and a dynamic leadership style to the iGaming space. He has been at the helm of Yolo Entertainment since January 2024, and under his guidance, the company is scaling rapidly, expanding into new markets, and improving internal mechanisms.
A Diverse Career Before Yolo Group
Matthew D'Emanuele isn't your typical iGaming CEO. Across his career, he has worked in a wide variety of sectors, giving him a varied perspective as a leader. He began his career in contact centre outsourcing before moving to an online car selling company in 2001, where he saw a massive growth in the business.
After five years, he moved to Oman, working with a major conglomerate that managed businesses in oil, gas, hospitality, and high-end brands like Bose and Tiffany's.
Later, he transitioned into investments as Chief Operations Officer for Oxford International Financial Holdings, relocating to Malta, a place he had often visited due to family ties.
In 2016, after stepping away from finance, he entered the iGaming world. He started at Gaming Innovation Group (GiG) before becoming CEO of Eastrock Group, a B2B company specialising in casino brands across Asia.
Yolo Entertainment
By 2023, D'Emanuele decided that he was ready for a new challenge. When Tim Heath reached out with an opportunity, it was too good to pass up. Within three months, he was leading Yolo Entertainment and began driving its next phase of growth.
Since taking over, he has led the company through an intense period of transformation. Yolo Entertainment now has around 250 employees spread across Estonia, the Isle of Man, Guernsey, Australia, Spain, and the UK.
His strategic initiatives and commitment to innovation are cementing Yolo Group's core B2C brands, Bitcasino and Sportsbet.io, as the preferred choice of customers in key markets.
One of D'Emanuele's top priorities is increasing Yolo Entertainment's presence in regulated markets. While details are still being finalised, he has confirmed that Ontario and key European and Southeast Asian markets are on the radar.
Beyond expansion, D'Emanuele is focused on strengthening the company's performance and refining its internal processes. He believes in "being brilliant at the basics" and ensuring that Yolo Entertainment isn't just growing but growing the right way. His approach is all about fostering an innovative, purpose-driven culture and building a team that's motivated by more than just perks.
With Yolo Entertainment on solid financial footing under his strong stewardship, D'Emanuele has his sights locked on long-term success. He wants to ensure that the company remains resilient and innovative, not just adapting to industry trends but actively shaping them.
