Tom Waterhouse: Betting on Legacy

Back in June 2024, I had the chance to chat with Tom Waterhouse on The Troubleshooters Podcast. We covered a lot of ground, but one topic really stuck with me—the big question most business owners face after selling: what’s next? It’s something I hear all the time from clients, and Tom’s experience sheds light on that exact dilemma.

Tom didn’t just inherit a family legacy in racing; his situation demanded that he pivot, which he did very successfully, making his own mark into the world of investments. After selling his family’s business, and later after running his course with the new owners, he set up a fund that’s all about putting money to work. Tom didn’t jump miles away from his expertise. Instead, his move saw him leverage that expertise and family legacy in gaming as a basis to evaluate opportunities in a specific niche, allowing him to seek out and invest in tomorrow’s winners – it worked, his investment platform is seeing extraordinary returns.

For any business owners wondering what to do after an exit, Tom’s story is a great example of how to do something different yet at the same time get clear on what you’re good at and be able to leverage that by bringing it to a new situation. Whether you develop a new venture, or simply put money to work so you don’t have to, Tom’s story is well worth examining closely.

During our conversation, he shared the three pillars Waterhouse VC deploy:  

1. Diversification: Tom’s approach is about not putting all your eggs in one basket. Not relying on one thing but spreading your investment risk – this hedging strategy and the intelligent use of the fund’s capital through the instrument of “options” is a key element in producing a leveraged effect.  
2. Long-Term Thinking: Instead of focusing on quick wins, Tom emphasised the importance of playing the long game. His fund is about sustainable growth over the long haul, something that resonates with anybody who has built something from scratch. It takes time to do something well. His global equities strategy via the S&P 500, underpinned by strict investment criteria when choosing equities, has so far delivered the Waterhouse VC Fund a great return on the cash not deployed, because of the intelligent use of options, which by definition preserves cash.          
3. Investing in syndicates: Tom has clearly leveraged his gaming heritage allowing him to find and pick individuals with the talent to successfully run a betting syndicate. This is not a big club; many would think this is risky but to Tom its just another day at the office.

For anyone selling a business, this conversation was a reminder to keep building a broader team especially as you contemplate the next chapter. Finally, and perhaps most importantly, is Toms obvious focus, he knows what his fund does and is good at and he refuses to be distracted.   

Selling a business is often a rollercoaster of emotions—excitement, relief, and sometimes that nagging feeling of “Now What?” But Tom’s journey demonstrates that with the right thinking, the next step can be even better than what came before – Tom thinks he will be doing this for the rest of his career, that’s a clear sign that Tom’s is in the right spot, he simply can’t imagine doing anything else!

For any business owner considering an exit, unsure what to do afterwards, take a listen to my discussion with Tom Waterhouse, you can also talk to me or one of our Partners – we have literally dozens of examples of clients, like Tom, who got creative and have found a new situation which they love.