Poker, and tournament poker in particular, is all about taking the opportunity to invest a small amount of money and turn it into a far greater sum.
Phil Hellmuth has built a career and significant wealth in that pursuit, notably turning his $10,000 buy-in in the 1989 World Series of Poker Main Event into a $755,000 first-place payday and €10,450 in the 2012 WSOP Europe Main Event into €1,022,376 among his many poker accomplishments.
The 17-time WSOP gold bracelet winner and Poker Hall of Famer has also parlayed his poker successes and notoriety into relationships with some of the most recognizable faces in the business world. Hellmuth has helped to shepherd businesses on the rise by making connections with venture capitalists and entrepreneurs who can provide vital resources.
But even with all of Hellmuth's business dealings and connections to the foremost figures in the space, no one connects at a 100% rate — and there was one occasion in which a miss measured out to $80 million - more than twice as much as Hellmuth has cashed for in all of the poker tournaments he's ever played.
How Keating tried to bring Hellmuth in
During a recent three-hour interview with Doug Polk, Alan Keating touched on a broad range of topics including his own YouTube channel and a variety of poker-centric topics. But two hours into the proceedings, Keating and Polk touched on what may well have been the most fascinating topic of the evening: a business deal that Keating attempted to foster between a company he'd personally invested in and Hellmuth.
"This guy starting a business, I don't want to say which one, he reaches out to me and he's like, 'Hey, I really want to get to know these important investors,'" said Keating. "He thinks very highly of them — the All In podcast guys, and things of that nature. I don't want them to think I'm leveraging our relationship, so I'm not comfortable making this connection [where] it's clear you'll give me something for doing it, and I don't want to position myself that way.
"But I know someone who will."
Keating reached out to Hellmuth with the kind of proposal Hellmuth has fielded on a number of different occasions, where he receives a certain percentage of the company in exchange for brokering relationships and connections with major financiers.
"I called Hellmuth and I said, 'I'm invested in this thing. I'm a believer.' I negotiated a deal for him where he has to put in $15,000 to get 4% of this business. He's buying at a 99% discount and he's got all these advisor shares. I did him good, and the counterparty was happy about it, too."
Hellmuth misses out on an all-time spin-up
Keating went on to describe how Hellmuth has excelled in this type of relationship and arrangement, and how Hellmuth was happy to open the line of communication to the prospective investors.
"He shows it to all these guys, maybe a half-dozen guys. All the who's who's," said Keating. "And all of them pass. And so Hellmuth calls me and he goes, 'Hey, they all passed. I'm not gonna put the $15,000.' To his credit, these guys are crazy sharp. Smarter than me in, like, every way, and if they didn't like it, it probably isn't a great investment, I guess."
Jumping ahead in time, Keating then recounted to Polk an interaction he had late last year regarding his own personal shares that he'd maintained in the company.
"I got an offer in November of last year from this secondary broker for my shares in this business, and they valued the business at $2 billion. And so, his 4% at that time is now worth $80 million."
From Keating's retelling of the story, Hellmuth was "irate" for four or five days upon having this revelation. And while he's often been known to utilize long strings of dialogue to convey his emotional state at the poker table, Hellmuth's reaction to the video on social media was summed up in a single word.
