Jason Calacanis' Poker Face

In our ongoing coverage of the life and times of Jason Calacanis, the video below is instructive on many levels. Calacanis—who is an Internet entrepreneur (the CEO of Mahalo), conference organizer (our former partner in TechCrunch50), and Web celeb—loves to play high stakes poker.

In fact, this week he will be one of the players on The Big Game, airing on Fox, in which businessmen are paired up with pros.

In the clip below, Calacanis loses a $204,400 pot to ten-time World Series Of Poker champion Doyle Brunson, who beats his two kings with three sixes. Brunson ran the river card three times, and won each time. The look of disbelief on Calacanis’ face at the end is priceless. “It looks like the Internet millionaire just had a server crash,” intones one of the commentators. And before that, “Jason is not a very experienced player.” Ouch.

To be fair, Brunson is one of the best players in the world, and Calacanis squeezed out at least one moment of glory in another hand. He won’t tell me how he did overall, but notes that a “Mahalo logo on TV for 5 nights” and a sponsorship he finagled “means I’m protected on the downside.”