When Mitchell Garber, CEO of online gaming company PartyGaming, the Gibraltar-based owner of Party Poker, stood up to speak at a recent seminar, he was met by many a sympathetic ear.

After all, it’s not often a CEO wakes up one morning to find that 80% of his customer base has been obliterated during the night due to forces entirely beyond his control – in this case the controversial bill passed by US congress in September, outlawing internet gaming in the country.

Little did the audience realise, however, the true extent of Garber’s seemingly life-long ill fortune. As he went on to reveal, during the dotcom boom Garber had been friends with Sabeer Bhatia, the founder of the then little known free email service provider Hotmail.

“I was in Sabeer’s office in 1997 and he was trying to convince me to invest in his company and buy 10%. I’m looking at his office and all the servers were held together with string; there was dust and fans. It looked like you wouldn’t invest $8, never mind $8.5 million,” Garber recalls. “I said: ‘I have to go now’, and I went off to play golf at Pebble Beach. He sold Hotmail to Microsoft four weeks later for $350 million.”

Worse still, Garber admits, “I made the same mistake with Mark Cuban”. Founder of Internet radio company Audionet, Cuban went on to sell his start-up to Yahoo for $5.04 billion in stock, to become, in the view of many, the quintessential dotcom entrepreneur.

And Garber’s bad luck shows no signs of abating. The associated costs alone of having to withdraw PartyGaming from the US online market have topped $250 million. As Garber concedes of his tenure at the helm of the company, it could arguably stand as “the worst stretch of luck in a seven month history of a CEO.”