First of all, this guy has started two successful media companies. That deserves respect. Secondly, he has guts, and he speaks his mind, and he is adamant about his causes, and he likes to get into meaningful discussion and debate. A simple Google search will show dozens of stories about Jason, I'm sure, and I bet most of them give him praise.
I read Jason's blog, calacanis.com regularly and I think people can really get some good direction from this guy. I wouldn't reccomend doing exactly what he did, because he does what he does extremely well, but he has some great principles. He lets his writers keep their words, he doesn't censor the bloggers, he pays people based on effort (and other things), he never builds a company to sell it, and much much more.
In a recent blog post about Jeff Jarvis, a famous blogger from about.com and other places, he was challenged by a commenter about insulting Jarvis, and he was asked to apologize. In response, he wrote:
"I don't expect people to sugar coat it when they come after me for my statements and positions--BRING IT ON! I love it... let's debate it, let's fight it out... that's how business/society/people move forward. I'll debate any one, any time... and if I lose the debate I'm a winner because I've learned something. That's really how I think... if I'm being an idiot and someone can prove it, well, good for both of us!"
I like that way of looking at a debate. It is something I would say if I had that thought. I am a huge porponent for learning something new every day, no matter what the source. And on sugar-coating, I can say that if I feel comfortable, I will simply be blunt, to the point of being insulting, just because I feel better expressing a raw thought instead of trying to filter it. While I would like to express myself in this way more often, because I feel like I am being more honest, I know there are some situations where a small amount of tact is required.
I'm sure the future will bring many more quotes and insights from the Jason Calacanis blog, interviews with Jason and his company WIN (Weblogs, Inc.).