I'll see your $50 and raise you a ride on my corporate jet.

Photographer: Mehdi Fedouach/AFP/Getty Images

Why CEOs Ace Poker

James McManus is the author of "Positively Fifth Street" and "Cowboys Full: The Story of Poker." He has written about the game for the New York Times, Harper's, the New Yorker, Foreign Policy, Esquire and Grantland. He teaches writing and literature at the School of the Art Institute of Chicago.
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Texas Hold'em tables often serve as less-genteel clubs for blue-chip businessmen. Instead of walking down fairways 30 yards apart from each other, or quietly hunting pheasant or muskie, poker buddies are elbow to elbow all night, competing and talking. The experience can tell them a lot about the other fellows' ability to make sound decisions under pressure. The quantitative and psychological acumen required by their day jobs also serve them well when a tight player check-raises them $2.50 or $25,000.

Bill Gates and Steve Ballmer aren't the only entrepreneurs to have honed their business-planning skills in dorm-room poker games. "In poker," Gates has written, "a player collects different pieces of information -- who's betting boldly, what cards are showing, what this guy's pattern of betting and bluffing is -- and then crunches all that data together to devise a plan for his own hand. I got pretty good at this kind of information processing." While Gates seems to play mainly bridge now, David Einhorn, Alexandra Lebenthal, Bill Perkins, Farshad Fardad of GlobalWide Media and Michelle Smith of Source Financial Advisors are just a small sample of executives who play poker for fun and often for charity.

Curt Kohlberg, the 56-year-old CEO of Kohlberg & Associates, is another one. He faces off about once a month with the toughest poker pros on the circuit, most of whom are less than half his age. Kohlberg has won $2,821,604, making him one of the most successful businessmen in tournament poker.

He doesn't need the money. His company, a consulting firm, has 200 clients with aggregate assets exceeding $3 trillion. "I'm a competition junkie," he tells me. "Gotta have that dopamine rush." (He's also a squash stud: He finished fourth in last year's U.S. Squash Masters the same month he made the final table the World Poker Tour Championship.)

Although Kohlberg plays fewer events than his competition, he can afford top-notch coaches, who’ve helped him compile hundreds of pages of hand histories into "a database of patterns to identify strong and weak betting lines" and determine "under which circumstances bluffing or value betting has a higher chance of success." He devours strategy books, subscribes to an online training site, and talks tactics with the likes of Jason Koon, Scott Seiver and Chris Moorman, young pros who play for nosebleed stakes.

I asked him which talents transfer most readily from boardroom to felt. "Negotiating business deals can be grueling," he said, "but you need the same concentration and stamina to go deep in a weeklong tournament. Sizing up opponents, being right far more often than not, adjusting tactics based on incomplete information to new players sitting across from you. At some point you have to go all-in with a hand or a bluff. Being wrong can be very expensive."

Biggest differences? "In business I want my `opponent,' the vendor, to make a fair profit. Once he's a client, the service K&A provides has to be ultra-high-quality, so I want my reputation to be `aggressive yet fair.' Whereas in poker my job is to take every last chip -- snatch the babies' candy right out of their cherubic little mitts. Instead of earning their trust, I want them to fear me. A lot."

He went on: "Most pros who don't know me peg me as Conservative Old Dude, but I usually start building my stack by targeting amateurs, and my cards then are often irrelevant." When he makes it to a final table he takes on the role of Psycho Ninja, donning "gangsta" attire and cracking weird jokes to keep other players off balance.

He wouldn't get that chance at the 2015 PokerStars Caribbean Adventure tournament, where I was also competing this month. I ran into him after he busted, and if he had a tail, it would've been tucked between squash-toned legs. It took awhile, but I eventually dragged the sorry tale out of him. He had built a 30,000-chip starting stack up to 73,000 and was the chip leader at his table -- until a Russian he'd never played with was high-carded to his immediate left with a whopping 150,000.

Kohlberg, in his grief over what happened next, was impressively granular. "The blinds are 100/200, 25 antes. A woman who's been playing straightforward raises to 500 with 45,000 behind. I flat-call with ace-king offsuit in the small blind. When the Russian tosses in a call, we're three-handed. The flop comes ace-10-6 with two diamonds, giving me top-pair/top-kicker. I check, Russian guy checks, the woman bets half the pot; I call and the Russian squeezes." That is, he check-raises, trying to win the pot right away. "The woman folds and I call, thinking he's trying to bully me, the Old Dude, with his huge stack."

The next card dealt, he said, "brings the queen of diamonds, completing the straight and the flush" -- for anyone holding king-jack or two diamonds -- "so I check. The Russian insta-checks, which can mean weakness or strength."

The final card from the dealer was the 10 of spades. "My hand obviously now has only bluff-catching value, yet instead of checking with the intention of calling or folding -- both of which are reasonable with stacks this deep -- I somehow manage, with my degree from MIT and experience in 100 tournaments, to have a massive brain-cramp: I assume the Russian's range includes only bluffs and weak 10s, ignoring the 16 combinations of full houses he could easily have (with 6-6, ace-10, 10-10, queen-10) given his betting line."

The regret is etched in mauve below Kohlberg's brown eyes. "So, I feign weakness with a head fake and a frown, tank for awhile, deciding to bet with the intention of shoving all-in to a raise, as my stack is right for this play and it would look super-strong. He accommodates me with a raise, I shove, and he tanks for five minutes before calling with 6-6. While he was tanking I realized my insanely impatient mistake and went into prayer mode. And before you can say `Kohlberg's a moron,' I'm taking the Walk of Shame, when I saw you."

He groans. "The worst thing is, I made this totally unforced error on Day One of the first tournament of the year in which I was gonna raise my game to new levels."

I do my best to commiserate, noting that all strong players make fatal misreads, but Kohlberg is having precisely none of it, as he heads to his hotel for a workout before catching a flight back to Boston.

He'll still be very good at his day job, though he'll have to wait until the next World Poker Tour event, at the Borgata, for his next surge of dopamine.

This column does not necessarily reflect the opinion of Bloomberg View's editorial board or Bloomberg LP, its owners and investors.

To contact the author on this story:
James McManus at arramc@msn.com

To contact the editor on this story:
Timothy Lavin at tlavin1@bloomberg.net