Probably one of the most pompous, and yet somehow successful bloggers on the web I’ve encountered to date is Jason Calacanis. On the plus side, along with his partner Brian Alvey they have built up a significant blogging network WeblogsInc (WIN) and have a few outstanding blogs mixed in with a few lemons like the sparsely updated Tablet PC blog (need a few more writers there?). Most WIN blogs aren’t on par with their top and bottom 5%, although whenever Calacanis spins they are all gems in the slushpile. But I don’t fault him there. Rather, it is how he constantly broadcasts his successes to the rest of us. I know, I know, turn off the volume … but the reality is there is some signal worth keeping the station flowing. Damned if you do, damned if you don’t. I listen, agree and believe about 10% of what the guy says.

Disclaimer: I visit one of the WIN network blogs almost every day and several others throughout the week. Occasionally I’ll blog stories here from some of their blogs. I thank, applaud and genuinely admire and respect some of the content they’re producing and a lot of his writers (though I think the better ones could do a whole lot better financially by doing their own gig as opposed to going under the WIN umbrella, but that’s another story for another day).

But man oh man, Calacanis just cracks me up with stuff like his new Ask Jason feature. Who does this guy think he is? Dear Abby? Sure enough he has and will continue to have a few butt kissers willing to ask him questions. And actually, Jason’s answers so far are not all bad, although they aren’t all completely true in my experience dealing with him.

After making a post here recently calling one of the WIN sites out on advertising practices, Mr. Calacanis was quick to add me to his Skype and then respond here in the comments, going back and forth about how “crazy” I was … “but in a good way” (what the hell does that mean?). I’m sure the minute he reads this post — and I know he will — he’ll either dismiss this as further evidence that I’m some shallow wannabe blogger flaming him just to draw attention (trollish behavior) or he’ll ride in on the white horse to set the record straight. Or perhaps it will just give him a chuckle for the day. Hopefully it’s the latter, as life is too short.

The only thing I currently want to “Ask Jason” is how often he stops in front of every mirror and admires himself?

Nick from Threadwatch seems equally disgusted over this Ask Jason garbage:

Is it only me that finds the whole “Ask John, Ask Jason, etc” columns just a little bit icky? Jason is the latest in a long line of these things, and i have to say, i NEVER read them.

Nope, Nick, unless you are a celebrity or its your job to provide an advice column, this is pretentious. But hey, this is a free country and people can be as pretentious as they like. Then again, maybe Mr. Calacanis truly believes he is a celebrity?

I can see Ask Engadget or Ask the Editor, but Ask Jason? Puh-lease. I wonder if he talks about himself in the third person, too?

Fortunately, some people are nothing like they are/behave/write online and I’m really hoping that’s the deal with Jason Calacanis. I’m sure this post will rankle at least some of the Calacanis faithful, and perhaps Jason himself, but somebody needs to keep it real. Sorry, folks, I have no beef with anybody who writes for WIN or does business with WIN, or really Jason Calacanis the offline human being as I admittedly don’t know him personally, I just take issue with the man’s ego online.

Maybe in person offline he’s a swell guy that is fun to throw a few beverages back with and this whole Ask Jason thing isn’t meant to be annoying, it’s genuinely meant to be helpful.

Will leave it there on a positive note.

Did this post make you go hmm?

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