The mythology of internet startups is all about big wins. But it's instructive, for prospective hustlers at least, to also look at the humiliating defeats — like this video of Web entrepreneur Jason Calacanis losing a $204,400 pot.

At least Calacanis had the good taste to lose to a big-time player, namely to ten-time World Series of Poker champion Doyle Brunson, who beat Calacanis' pair of kings with three sixes. But his big fail does tell us something about self-described poker addict Calacanis' tendency to overplay a strong hand. A more rational founder might have banked his proceeds after selling Weblogs, Inc. to AOL for $25 million five years ago; even after taxes and investors, that kind of money can set you up comfortably for life if spent prudently. But Calacanis has been living large, splurging on a Tesla Roaster, laying down money on his poker sideline and plowing money into his still unprofitable, still insanely risky sounding search startup Mahalo. Calacanis' accountant is probably already screaming this at him, but we'll join in: You can't afford too many of these big-losing hands Jason, the occasional big win notwithstanding. If you're going to try to bluster your way into the big leagues, at least learn to make your bets and bluffs a bit more frightening to the competition.

[TechCrunch]