Never Tell Him the Odds

SHALOM MECKENZIE made a $1.4 billion fortune after merging his gambling software company with DraftKings. Now he's rolling the dice on Amp, an at-home exercise machine startup. It's a long-shot bet-but he has a good reason to make it.

- By Will Yakowicz

In October 2020, Shalom Meckenzie was playing poker with his employees on a 192-foot yacht off the coast of Greece, celebrating that his gambling software company, the Isle of Man-based SBTech, had merged with DraftKings to go public via a SPAC in a $975 million deal a few months earlier. As the largest shareholder of DraftKings, Meckenzie became a billionaire that May when its share price passed $25. During one of the poker hands, he made a losing bet that would cost him hundreds of thousands of dollars—and inspire his next venture.

One of his top product executives in Bulgaria weighed 280 pounds but had never been motivated to lose weight. Meckenzie, feeling flush with success, proposed a big wager. “I told him that if by the first of January you're below [220 pounds] I'm going to take a 300-foot yacht in the Caribbean, and you're going to choose all the people that are going to go on the yacht, and you're going to have the craziest and most fun week you will ever have,” says the 48-year-old Meckenzie from his home office outside Tel Aviv, Israel.

The employee, Ian Bradley, accepted the wager. The other executives sitting on the yacht realized that if their colleague won, they would get a vacation invitation and decided to help him lose the weight. Back in Bulgaria, they put a stationary bike in Bradley’s living room, threw out the junk food in his pantry and hired a chef and personal trainer. The trainer was told he would get a big bonus if Bradley lost 60 pounds over the next few months. He lost the weight and won the bet.

“It was one of the best bets I’ve lost in my life,” says Meckenzie, who is in great shape for any age, let alone a man nearing his 50th birthday. Meckenzie flew Bradley and ten others on a private jet to Dubai, where they stayed at a five-star hotel and partied for five days. “I think it ended up costing much more than a yacht in the Caribbean,” Meckenzie says, laughing.