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Secondary Thoughts by Siena: Interview with Tim Heath
This is Secondary Thoughts by Siena — an interview series where legendary entrepreneurs and investors reflect on their investments and broader professional journeys, speaking openly about their wins and losses.
Today’s guest is Tim Heath, an Australian serial entrepreneur based in Tallinn. He is the Founder of Yolo Group and a General Partner at Yolo Investments. Tim’s journey has been extraordinary — from being nearly broke, traveling to the other side of the world, and playing poker to survive, to building one of the leading crypto, iGaming, and investment powerhouses, with close to $1 billion in assets under management (AUM).
The series is produced by Siena, a boutique VC fund focused on secondary investments in high-growth scaleups from the CEE and Nordics. Its portfolio includes success stories such as Bolt, Oura, and Booksy.
Tim Heath, the Founder of Yolo Group and General Partner at Yolo Investments
Tell us a little bit about Yolo Group and Yolo Investments. What is your vision for the group?
Yolo Group was founded more than a decade ago on a simple concept: that we could deliver a better gaming experience to players with crypto than they were getting from traditional fiat operators.
We began with the basics, such as faster withdrawal times, but we soon realised that we could go much further if we owned the ecosystem around our gaming brands. That led to the creation of Yolo Investments, providing the opportunity to invest in dozens of exciting companies at the cutting edge of gaming, blockchain, and fintech.
The vision we have is two-fold. We primarily invest in disruptive businesses across frontier tech. Secondly, we aim to add genuine value along the way. We don’t see our job ending the moment we sign a cheque. We’ve built up a great deal of expertise and a deep network over the years given the own startups we founded, along to the businesses we have managed and then gone on to sell, which has enabled us to have a strong track record of supercharging the growth and returns of the companies we invest in.
We’ve just completed our €100 million raise for our Fund II, which is already backing 12 exciting winners. Over the coming months, we’ll be making further investments.
What excites you these days? Are there any companies on your radar – or perhaps topics or industries – in which you're developing a growing interest?
The thing that got me interested in crypto all those years ago is actually what still keeps me excited. When you boil this down to the fundamentals, it's about finding better ways to move money.
When you take that as a starting point and then think about how to apply it across different industries, you’ll realise this is probably the biggest opportunity right now.
There are a few specific areas I’m watching very closely, and where Yolo Investments is already making moves.
Embedded finance is one. This is mainly a UX issue. Why should people have to leave the app or whatever is it they are doing to make a payment? I see a future where payments are completely seamless and don’t disrupt the user experience. Chatting with a friend and you need to pay them back for dinner? That should be one click from within the messaging app.
Onboarding more users to blockchain-based products is another area. For me, the next breakthrough is one of abstraction. People shouldn’t need to even be aware they are using a crypto product. It’s about delivering the benefits without the need to worry about private keys, gas fees or which network I’m using - all of that should be managed behind the scenes.
And tokenisation is a clear trend that’s only going to accelerate. We’re already seeing company shares being tokenised, which enable 24/7 trading and global access, but that’s only the beginning. There’s very little that can’t be tokenised and brought onchain.
But again, all this comes back to that simple question of making it easier for people to move money.
Looking back at the investments that you have made, which of them have surprised you the most – either by outperforming your expectations or falling short?
It’s tough to single out one or two, as we’ve had so many successes. But if pushed, ONE.io is a great example of how we work.
We started out as a customer simply because the team was offering something we needed. They had a clear vision to simplify end-to-end financial services for corporate clients and importantly for us, they had integrated crypto deep into their product offering.
We loved the service they were providing us, and as we got to know the team and founder, it became clear there was a deep strategic partnership to be formed. It’s an organic way to invest that’s paid off hugely for us. And I’m not just talking in terms of raw ROI. As ONE has grown, we’ve been able to utilise their products and services to an even greater degree.
What have been some regrets in your professional life where you wish you invested more (time or money) but didn’t at the time? How do you feel about them now looking back in time?
When I first arrived in Europe, I kept myself afloat playing poker. If poker teaches you one thing, it’s that you can’t dwell too much on “what ifs”. You will win and lose hands, but your focus needs to be on consistently making the right decision, regardless of the result. If you do that over a large enough sample size, the math takes care of the rest.
Yes, I’ve missed opportunities over the years. But nothing really stands out because it’s not like we’re short of opportunities right now. This is such an exciting time to be an investor. We know where we’re strong, we have conviction in our thesis, and that means I can look forward without regrets!
What’s always in your carry-on?
Not much to be honest. In a world where you can do just about anything from your phone, it’s easy to travel light.
What’s your most irrational habit?
Thinking the Socceroos (Australian national football team) won’t end up disappointing.
If you weren’t doing this, you’d be…?
Playing poker, betting on the horses, trying to find an edge wherever I can.
One app you wish didn’t exist?
Other than LinkedIn, I don’t really use social apps, so it wouldn’t bother me if they were shut down.
What’s one thing you collect (on purpose or not)
Tee times. I love a round of golf and I’m fortunate to have played on some great courses all over the world.