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How to be the most hated person on the Internet: Five role models

It's easy to be disliked and ignored, but it's quite another to be hated and obsessed over.

Dave Winer believes he is "one of the most hated people on the Internet" (full blog post). We tip our hats to him. It's quite an achievement. Considering all the trolls, jerks, and narcissists (yes, me too) who post like crazy on the Web, it's no mean feat to be hated by so many.

But there can be only one who is "most hated." And we wonder how one goes about achieving that distinction. Restricting the discussion to technology personalities who are active contributors of original content, we came up with five contenders, and what we think they are doing so well that we can all learn from.

Dave Winer
He was a big contributor to the inventions of blogging, RSS, and other key Web technologies. But to call him prickly when it comes to his place in the tech firmament is an understatement. Typical story: I wrote a how-to piece on RSS but neglected to mention his contribution, and then Winer posted a blog item in which he equated me to Dan Rather on 60 Minutes during the GM exploding fuel tank story. When I at first contacted him privately in an e-mail, he publicly demanded an apology. Winer's secret: Be smart, and then be abusive. See also: The Winer Number.

Where to find him: Scripting News. Twitter: DaveWiner.

Michael Arrington
He started TechCrunch, the right blog at the right time. Then he milked his position and growing power by bullying start-ups with threats of no coverage if he wasn't given exclusives, slamming The New York Times' ethics, and stating "If I'm first, I don't have to be...intelligent." A lawyer by training, Arrington uses a litigator's tactics: Make bold arguments that draw attention to your case but make people hate you in the process. They're less likely to forget you that way.

Where to find him: TechCrunch. Twitter: TechCrunch.

Jason Calacanis
A media entrepreneur whose big win so far is having sold the blog network behind Engadget to AOL, he has since taken to acting like a new-money rock star, publicly buying flashy cars, strutting around the conference he produced with Arrington with his two mascot bulldogs, calling his Twitter followers the "Jason Nation," and then telling bloggers he's too good for the medium, opting to write instead to a private e-mail list. His weapons of choice: arrogance and money.

Where to find him: CEO of Mahalo. E-mail list signup on Binhost. Blog: Twitter: JasonCalacanis.

Loren Feldman
In response to a now-forgotten slight, the grouchy videoblogger of 1938 Media started mocking PR consultant and social media guru Shel Israel mercilessly, via a video series featuring a sock puppet of Israel cluelessly interviewing online celebs. Feldman also registered and put up fake posts under Israel's name. The public divisiveness of the conflict delighted many, but the mean-spirited bludgeoning offended many others. Feldman is charming in public but has a unique skill: He not only knows how to hold a grudge, he can nurse it like it's a helpless kitten.

Where to find him: 1938 Media. Twitter: 1938media.

Owen Thomas
The chief blogger at Valleywag takes stabs at anyone and everyone in the tech world. Although arguably just doing the bidding of Nick Denton, CEO of Gawker Media and his employer, Thomas' Valleywag dishes out a lot of dirt, much of it highly personal and enough of it inaccurate. Owen's talent is having no boundaries. Everything in a tech person's life, true or not, is fair game on Valleywag.

Where to find him: Valleywag. Twitter: Valleywag.

Disclosure: Thomas used to work for me at Red Herring.

One has to ask...
Is being hated always a bad thing? It's working out well for the people on this list. Share your thoughts in the comments below.