I would never work for Jason Calacanis - There, I said it

Say what you will about him or his style but my experience was was a net positive and if you turn the clock back and I'd do it again.

It's the self-obsession inherent in the way he keeps referring to his own (self-perceived) good qualities as the ideals to which others should try to live up to.

It's the pointless bragging. "Oh, I've only been tired a few times in my life, usually after a marathon". Cool story, bro!

It's the way he gives the impression that the only thing he seems to value in his employees is how much they're willing to kill themselves for the sake of the company.

Above all, it's this apparent feeling of entitlement that he deserves to have the best people in the world working for him. This might be justified if he'd sold his last two companies for ten billion dollars a piece and made all his employees rich. But according to wikipedia he's sold one company for the $30 million range; presumably enough to make the founders rich but only to give a modest payoff to the employees. If the best he can say is that some of his employees make $100K after getting $30K for the first few years (compared to a big company where they'd instead make $100K after getting $75K for the first few years...) then I'm really not sure where this sense of entitlement is coming from.

Jason is totally demanding and pushes everyone around him to their limits. Yes. True.

But, underneath all the bulldog, seriously the guy has a heart of gold. Sometimes he doesn't show it, and even he'd admit some level of narcissism, but from personal experience, I can fully say that working with Jason changed my career for the better in every way.

I originally worked with Jason at Weblogs, Inc., and as we were acquired by AOL, worked with him on the relaunch of Netscape. I went through a personal tragedy during the launch of the site, and Jason / the team were instrumental in me coming out of that with my wits about me.

To be clear: Jason is hard to work with. He does joust publicly, which I would attribute to his form of marketing.

I have absolutely no inside knowledge of his actual tactics, but my guess is he takes on someone who he knows people don't like, then points out their flaws over time, figuring eventually he'll come out on top since his side of the story looks so rosy by comparison. Oh, and he does this by being fairly hyperbolic. (Mainstream media, junkets in journalism, Gawker, Pay-to-play angels, SEOs, off the top of my head.)

That all aside, I think working with Jason set me up to have a wide-eyed view of startups. I treasured the experience, and while I think everyone should evaluate their personal limits carefully before embarking on a career with someone who will literally push all of them, I don't think anyone who's worked with him has regret the time they spent with Jason. That doesn't mean all of them want to work with him again... but I heartily encourage anyone who wants to be pushed to work with him. It will be a hugely rewarding experience professionally. It was for me, anyway.

I actually have worked for one startup before and am doing my own right now.

I know about long nights, tight deadlines, and no money.

I know about creativity due to constraints and responding quickly.

I also know about abusive bosses and unproductive labor practices.

I would be hard pressed to find ANY software developer that agrees that they perform best under a boss like Jason.

I realize this may result in "I don't get tired" but for my two cents, chemical augmentation isn't really the same thing.

Or maybe that's a more accurate description of Olympic athletes than I'd like to admit.