High-stakes regular Alan Keating recently shared an eye-opening story on the Doug Polk Podcast, revealing how Phil Hellmuth may have missed out on one of the biggest financial opportunities of his life.
According to Keating, he was invited to invest in a startup alongside other early backers. The company’s founder, recognizing Hellmuth’s immense promotional value, offered him a 4% equity stake for just $15,000 — a massive discount on the company’s valuation. As PokerNews reported, it amounted to a 99% discount.
But Hellmuth hesitated. After learning that several experienced investors had already declined, he ultimately decided to pass on the deal.
Just a year later, Keating received a call from a secondary broker looking to buy his shares. The company’s valuation had skyrocketed to $2 billion, meaning Hellmuth’s would-be 4% stake was now worth $80 million.
Keating said Hellmuth was devastated. “It took him several days to recover,” he noted, suggesting the poker legend was overwhelmed not only by the financial loss but also by the blow to his confidence. As Doug Polk put it:
“I think part of Phil’s personality is like being right at things. And when you take an L like that, the L hurts almost more than the money does to Phil.”
Of course, as any poker player knows, decisions are easiest to judge in hindsight. Based on the information Hellmuth had at the time, turning down the offer might have seemed reasonable — but this time, it cost him dearly.
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