Matthew D’Emanuele cuts a relaxed figure in his office in the Estonian capital of Tallinn. The CEO of Yolo Entertainment has settled into his new role since joining the crypto-first operator last year – and he has big plans. He joined the group last year from Eastrock Group following a restructure which saw Yolo Group split into three distinct arms. Yolo Entertainment houses the group’s B2C operations, Yolo Platform is the B2B division while Yolo Investments remains on the hunt for striking startups in the sector.

D’Emanuele, who also spent time with Gaming Innovation Group, is relishing the chance to get stuck into his new field. Speaking to EGR, D’Emanuele lays out his plans for Yolo Entertainment as he reflects on his journey to the top job. Touching on conversations with the company’s founder, Tim Heath, the CEO explains that the pair’s aligned vision for the company was a key factor for bringing him onboard.

With a global reach and growing talent base, Yolo Entertainment appears to be well placed. Here, D’Emanuele suggests crypto sits on the precipice of mainstream explosion as he explains how the firm is ready to cash in on the boom.

EGR: How did the opportunity to join Yolo Entertainment as CEO come about, how did that process unfold and what were your feelings?

Matthew D’Emanuele (MDE): It was definitely a feeling of excitement. It came at the right time as I felt very ready to take that next step. Now, what that next step may have been at the time, I wasn’t quite sure admittedly. By pure coincidence in a space of a week, somebody reached out to me. The following day, another call came in. Then a third call came in or a message and I spoke to an old colleague of mine [for some advice] and he said: ‘I think I’m about to make your life a little bit more complicated, Because I think Tim [Heath, Yolo Group’s founder] wants to have a chat.’

That next day, we had a call booked. We ended up spending an hour and a half on the phone. The initial plan was to come across to Tallinn for an interview but I then spent the next two days meeting talent from around the organisation.

I’ll be honest, when it was mentioned that Tim would like to have a chat, I think my mind was made up. I’d been working with Yolo Group as a customer and was lucky enough to have been invited to various investment events that they held and I was fascinated by that ecosystem. I was really intrigued by how wide and how diverse it was but also the opportunity it possessed. This was something that really enticed me.

EGR: What were those conversations like with Tim that convinced you to come onboard?

MDE: I appreciated how honest and genuine our discussions were. I was ready for that next stage in terms of a bigger organisation and the demands that brought, being able to have more control over the projects and influencing the direction and vision of the organisation. There was a board desire for the organisation to go through a series of structural changes and I felt I could really contribute to that.

I’ve been lucky enough to have worked across different industries within senior management so that the leadership side of things and the understanding of organisations and how they work was something I was very comfortable with.

I still see myself as relatively new to gaming and I had said this to Tim. I had asked him whether he was concerned that I am not a gaming specialist per se or indeed a crypto specialist. He confidently said absolutely not.

He wanted somebody to come in and help build the organisational structure in a way that we had the ability to execute the vision while continuing to be as innovative as we like to be. You can have all the aspirations in the world but if you don’t have that support system and infrastructure to be able to carry those off it will be very difficult to achieve.

EGR: Was the lack of crypto experience a daunting factor when coming into the role?

MDE: I think it would be fair to say there was an element of ‘can I do this?’ It is very natural, especially when taking a step up or in a different direction. But I’m a firm believer that you always take on a challenge that’s slightly bigger than what you’ve been used to. The size of the talent base didn’t concern me or the numbers. I knew I would enjoy working closely with Tim, who is clearly a visionary in the space. The fact the conversations were so in-depth and I could see how aligned we were with many elements, but also where we were not in agreement, it was a healthy and constructive discussion. That’s ultimately what sealed the deal for me.

EGR: Looking at your first few months as CEO, what would be three words you’d use to describe the experience? And is it what you expected it to be?

MDE: Intense, exciting and engaging. And it has been everything I expected. I use the word intense in a real positive manner. I embrace that intensity and I love the fact we move as quickly as we do. I am however focused on ensuring each time we innovate we support this by having clear policy and procedure. It can be hard to find the balance but that’s part of the fun.

EGR: Could you delve into some of the core markets you are focusing on? And does the future for Yolo Entertainment lie in the regulated space?

MDE: We’re lucky enough to have a global focus. We are changing our strategic focus to where we see crypto adoption. If we see a particular territory that is demonstrating increased crypto take up, then that’s a territory we want to explore more and see how we can stimulate those players. It is more ‘following the coin’ rather than the industry.

I’ve always been very positive around pre-regulated markets as it allows us to gain an understanding of how the market works and importantly what stimulates the customer base before their needs and desires are heavily restricted for them. Naturally, we embrace regulation, we very much believe in creating an environment that protects customers. I, however, think in many instances, regulations at the moment are not protective of the player.

If anything, I think they are driving players into a different sphere that has bad actors. Irrespective of the jurisdiction, it’s about how do we put our best foot forward and create an offering that is fun, fast and fair.

EGR: Since the Yolo Group restructure, how is the B2C arm working with the B2B and Yolo Investments division in a cohesive way?

MDE: We have a responsibility to make sure that we create some separation between the business models. We have a really successful B2B model and part of that is the level of trust in that structure from our loyal customers.

That trust comes in the fact there’s no collusion, Yolo Entertainment is a customer of the B2B arm like other operators out there. Naturally, we share best practices when possible. There will be things they’re able to test and innovate with Yolo Entertainment, and if it works, we are committed to ensuring our B2B operators benefit. Ultimately our ecosystem is there to enable operators across the industry to continue delivering a fantastic customer experience to their customers.

I am included in various potential investment opportunities. Again, we’re a great user case. If it is something we feel could benefit Yolo Entertainment, we will always be open to it.

EGR: There has been a significant spike in the number of crypto casinos in the space but no major moves from established, traditional operators. Can you see this changing any time soon?

MDE: We’re still a relatively young industry in terms of the online aspect of gambling. I have seen a genuine concern by other large operators when it comes to crypto around how fair and transparent the processes are. One big learning I’ve had from crypto is that transparency is absolutely, fundamentally there. This is the benefit of the blockchain, you can see where the money is moving and how it’s moving. That’s a massive positive to the user experience.

Over the next 12 months, we’re going to see more inertia towards crypto and understanding the values and principles that sit behind crypto and how they can support customers better.

Ultimately, we’re here to deliver an outstanding customer experience and part of that experience is to ensure they get paid their winnings immediately, this is a real moment of truth for a customer when engaging with an online casino. We are in a position to be able to pay our customers out in seconds and minutes at most, whereas the traditional online operator is still at several hours, depending on the payment method.

At some point there’s going to be a business case for crypto. We’re on the edge of the precipice of crypto being more widely adopted. It’s a journey, but I think that’s what will help the big operators realise there’s an opportunity. It will not be long before some of the larger firms out there start accepting crypto and that will be the catalyst this technology deserves.

EGR: In terms of other innovations in the online gambling space, what do you think is the most important development at the moment?

MDE: The real innovation is coming through fintech. I think the online gaming space is a good beneficiary of the advancements made there. We’re investing heavily in fintech. If we create the right payment wallet and that frictionless environment, then that is a big enabler for us.

I think innovation can often be a buzz term. It can often be perceived very functionality such as ‘how slick we can make a bet builder?’ but it is far more comprehensive than that. It’s about creating a smooth and frictionless process. In terms of sports betting, that static environment we are used to when it comes to the way customers engage with their preferred sportsbook is going to move away and it will be far more about designing an intuitive customer journey.

EGR: How important is it for Yolo Entertainment to engage with Gen Z as a crypto-first operator?

MDE: I think this new audience coming through are far more educated in the Web3 crypto space than the vast majority of the industry. That brings a very new type of problem. Suddenly, we’re not educating players; we’re being educated by player demand by and by player expectations. That’s a shift for sure.

What’s key for us as an organisation is finding the type of talent now that can compete with customer expectations and that can make sure that we’re moving ahead of those expectations. Because I think the vast majority of the industry at this point have a very strong idea of what good looks like but I feel at times that image is pretty much what it has looked like the last 15 years. Customers deserve more.

We have that new audience coming through, the new player profile, wants to connect via MetaMask, they want to be NFT driven, they understand it. We really need to gather pace and make sure that we can mirror those expectations and help identify new ways to build engagement.

EGR: Within that, how does an operator go about creating a welcoming and attractive environment for Gen Z players?

MDE: There will always be a space for that traditional legacy. Because naturally, you’re going to have that customer base from 20 years ago that I’d like to think are still going to enjoy that experience over the next 10, 20, 30 years. Whether they want to change is a different story, they shouldn’t need to change, my style is that we allow them to continue doing that if that is what they prefer. Likewise, we then need to ensure we’re also thinking about that new type of customer coming through who consume and interact in a very different manner

What’s absolutely fundamental is that we create an environment that stimulates users. And that’s where that intuitive experience comes into it. That’s easier said than done, admittedly. But we can start to become a lot more understanding of how people have found our site and start to build some of that predictive modeling and based on the principles of how individuals hit the site. We then, very quickly, throughout their first transactions, try and build that understanding.

Netflix has pretty much done it; we all see the same Netflix homepage. But over time, we don’t all see the same TV series and films being projected, so it’s possible. It’s the same principle in gaming, we still haven’t accepted that that’s the way consumerism is going. They expect to see what they want to see.

EGR: What is the type of content that you see that demographic engaging with?

MDE: I think we can see the way gambling has matured over the last 30 years of making your bet at the start of the game and waiting until the end of the match to see whether you won or not. We have moved on, we are dealing with a generation that wants to be able to place several bets in real time, perhaps seconds before an event or within a game. This is why tennis is such a big stimulant. People like to be able to bet on the next point, they want that instant gratification. And that’s something that we really need to continue working with. So that’s why I think esports also has got a position to play. I don’t think we’ve really quite achieved anything of what we’re capable of when it comes to esports. Again, that younger generation coming through, I see it, [they] will happily sit and watch YouTube and watch FIFA being played on YouTube.

EGR: How do you envision the next several months of Yolo Entertainment under your leadership?

MDE: A key part of the last nine months has been restructuring the business to make sure we have the right roles, right responsibilities and the right talent to drive the business forward. We still have lots to achieve in 2024 but we are also now already planning what Yolo Entertainment looks like in 2025 and further on.

The post Q&A: Yolo Entertainment CEO on crypto’s continued growth and Gen Z first appeared on EGR Intel.