Among them was Australian bookmaking legend Tom Waterhouse, who shared his extraordinary ride from an on-course bookie to a betting industry powerhouse.
What started as a family trade turned into one of the fastest-growing online sports betting businesses in Australia—before he sold it to William Hill in 2013 for A$34m in cash with potential earn out of $70m.
A sudden wake-up call
Tom Waterhouse was born into bookmaking royalty. His great-grandfather was taking bets on horse races in the 1800s. His grandfather and father kept the tradition alive, and Waterhouse himself expected to do the same for life.
“I had a blueprint. My family had been in the business for generations, and I loved it. I thought I’d be on the racetrack forever,” he said.
But the game changed overnight. In 2008, Australia’s High Court ruling on Betfair shattered the old-school model. Suddenly, online bookmakers could legally, and the shift to digital betting took off like wildfire.
“Before 2008, I barely used a computer,” Waterhouse itted. “But I knew I had to pivot and go online.”
From 100 to 250,000 customers
That pivot led to TomWaterhouse.com. At first, it was just an attempt to retain his 100 on-course customers. What happened next was beyond anything he had imagined.
“In a little over a year, we had a quarter of a million customers,” he said. “We went from two people in a tiny office to over 100 employees.”
The timing was perfect. 3G internet launched, iPhones hit the market, and advertising restrictions eased. The digital betting boom was on, and Waterhouse rode the wave all the way to the top.
Buy or sell
By 2013, Australia’s betting market had become a battleground.
Giants like Ladbrokes, Bet365, and Paddy Power were throwing down millions in marketing and tech. The cost of staying competitive had skyrocketed.
“TomWaterhouse.com was very lucrative, but the costs and market dynamics changed significantly,” he said, likening it to the current situation in the US, where success depends on scale and operational leverage.
“The same thing happened in Australia,” he added.
“We were spending A$90m a year just on marketing. We needed scale—we either had to buy or sell,” Waterhouse said.
Enter William Hill, the British gambling titan, which acquired TomWaterhouse.com as part of a $700m buying spree.Waterhouse’s deal included an earn-out agreement, but he quickly grew frustrated.
“We kept writing to the board, saying, ‘We won’t hit our targets unless the business is structured differently.’” Within six months, William Hill handed him the reins.
“I’d never had a such job before,” he said. “But they said, ‘Do you want to run the whole business?’ And I thought, why not?”
The gamble paid off. As CEO of William Hill Australia, Waterhouse oversaw $2.5bn in turnover and led a 500-person team across multiple countries.
“It was an amazing journey,” he said.
The next bet
After William Hill sold its Australian operations to the Stars Group in 2018, Waterhouse decided to play a new game: venture capital.
He launched Waterhouse VC, focusing on the technology behind the gambling industry—data providers, mobile app builders, and platform innovators.
“The biggest shift has been product innovation,” he explained.
“It’s not just about placing a bet anymore—it’s about unique features like cash-out options, multi-bet builders, and in-play betting.
“At William Hill, we had over 500 different external products, but we could never prioritise or get them in quick enough.
“That’s when I realised the real edge in the gambling industry lies in understanding the product layer,” he said.
Lessons in scaling
Looking back, Waterhouse believes his biggest mistake was not hiring someone who had already built a similar business.
“I should have just hired someone from Paddy Power, William Hill, or Ladbrokes—someone five years ahead of our journey—who could have given me a blueprint for SEO, digital marketing, mobile development, and how to build a business,” he itted.
While he had built a dedicated team, they all faced a steep learning curve.
“Now, when we invest in start-ups, we give them a blueprint of how we think we could assist them,” he said.
