Phil Hellmuth has overall had a poker career full of highs but along the way there has been plenty of bad beats as well. But it turns out, the largest bad beat of his career may have come off of the felt.
In a recent Doug Polk Podcast episode, high stakes poker cash game regular Alan Keating revealed a story that detailed a huge investment chance that left Hellmuth cursing his decision-making.
Polk, who has experience with investments of his own, led the discussion with Keating as Hellmuth became the center of the conversation.
Keating recalled how he had been approached by an entrepreneur who wanted to gather investors for a business, which remained nameless. Keating eventually set up an offer for Hellmuth to get involved: $15,000 for a 4% stake in the fledgling company.

It seemed like a solid deal for Hellmuth according to Keating who said he also got some extra perks for Hellmuth as well. But after much deliberation, Hellmuth and other investors decided to decline the chance as they did not deem it worth the risk.
After over a year, Keating was contacted by from a broker who revealed that the business was now valued at $2 billion, which means Hellmuth’s $15,000 stake would be worth $80 million today, an amount of money that is likely beyond the realm of any professional poker player out there.
Hellmuth’s Reaction
“He was irate for four or five days when he kind of figured it out,” Keating said. And who could blame him? Realizing that $15,000 could have turned into $80 million has to hurt, even if you’re Phil Hellmuth.
Safe to say that this type of revelation would stick with anyone for a while, thinking about the fortune they could have received as well as the prestige of being in on such a prominent business.
Hellmuth has always been someone to be willing to promote businesses and brands. Much like positions in poker he is always looking to position himself into something new and cutting edge, so this type of missed chance has to pack a little bit of extra hurt for him.
Arguably an even more painful experience for Hellmuth than a one-outer in a WSOP event.