I listen to TWiT every week and Jason Calacanis is a regular guest (though rarely when
Chauncey John C. Dvorak is on). The guy knows the tech industry inside out and backwards and is an astute businessman, and he’s not afraid to air his opinions on anything (which is probably why he and Dvorak don’t seem to get along – they both have strong “I’m right and you’re an idiot” beliefs). Calacanis seems to be one of those love-him-or-hate-him kind of guys, though I keep flip-flopping. He can sometimes be an annoying blowhard while other times be one of the most insightful tech guys around. I always enjoy TWiT when he’s on though since he’s always entertaining; he does a spot-on Christopher Walken impression.
He even showed up on a StackOverflow podcast a little while ago and spent the entire hour begin clever and insightful, so I’m wondering if the blowhard is kind of a persona that gets people talking about him – he certainly seems to subscribe to the old mantra “I don’t care what you’re saying about me, as long as you’re saying something”.