“Several billionaires got their first stakes in poker games. Kirk Kerkorian funded his first business, the charter airline Los Angeles Air Service, with poker winnings. H.L. Hunt bet everything he had in a poker game and won his first oil well. Bill Gates, John Kluge, Texas oil mogul Clint Murchison, and corporate raider Carl Icahn all played poker for large stakes before they got rich. It’s not just billionaires: Richard Nixon paid for his first congressional campaign with poker winnings and parlayed that into the presidency, where he continued to make risky bets but with less success. History is filled with people who began their routes to success with gambling winnings. You won’t find as many equally successful people whose first stake was a bank loan or money raised from issuing securities. Even the losers can benefit. Writers from Dostoyevsky to Mario Puzo credited gambling losses for both the inspiration and the motivation to complete some of their greatest works.”
- Aaron Brown, The Poker Face of Wall Street
Barring the inheritance of a substantial family fortune — or being handed the reins of an extremely lucrative business — it is hard to become exceptionally wealthy without taking aggressive calculated risks. Knowing how to position for upside while managing the downside is thus a highly desirable skillset.
In that light, why might poker figure prominently in the biographies of billionaires? Did the game hone and shape their instincts… or did their natures instinctively draw them to the game… or both?
Calculated risk is the mother’s milk of poker and trading — two zero sum (actually minus sum) games in which variance dominates short term, but skill dominates long term.
Do you remember the last aggressive calculated risk you took? Do you think about trading in these terms?
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