How his ego helped him: Colbert got to lampoon an unpopular sitting president to his face in front of a live audience to a degree that would have gotten a jester killed in the Middle Ages.
How it hurt him: Stephen Colbert jumped the shark from parodying guys with huge egos to being a guy with a huge ego when he tried to get on the Democratic ticket in South Carolina via a Facebook campaign. Oh he said is was a joke, but we know better. We know.
How his ego helped him: While every mainsteam media company was busy sneering at "bloggers," Nick Denton built a new media empire. Now, despite his sites being just over 5-years-old, Denton already comes off as the next Ted Turner.
How his ego hurt him: Denton seems unable to keep an editor on his flagship site, Gawker, for over a year. Also, the pink slips he sends around to his employees have an annoying habit of popping up on the Internet.
How her ego helped Her: Ariana Huffington managed to turn her Blackberry address book into creating what is consistently the most linked to blog on the web.
How her ego hurts her: In 2003, Ariana Huffington ran for governor of California and received .6 of the vote. Dead candidates have done better than that.
How her ego helped her: For a medium filled with actual porn, we can't imagine it is easy to claw your way to the top of the pile by being a sex columnist.
How her ego hurt her: Don't be fooled by Allison naming her new website Nonsociety, Allison is the new world order socialite of the first degree and has a long list of nasty insults attached to her name to prove it such as "B-list mediocrity," a la Radar Online or if you prefer the Gawker, you might refer to her as a "professional drama factory."
How his ego helped him: Forget revolutionizing celebrity journalism, Harvey Levin might just changed the face of all journalism. Utilizing one man news reporting teams TMZ is top dog not just because they're the nastiest celeb blog, but also because they can get pretty much every story up faster than anyone else.
How his ego hurt him: Recently, Levin has been accused of driving off some of his top talent, specifically general manager, Alan Citron and Gillian Sheldon TMZ's supervising producer, by refusing to compromises.
How his ego helped him: From working at a 7 Eleven to being perhaps the most successful "journalist" of new media, Drudge's ego has allowed him to survive scathing attacks, break news before major media outlets and make a fortune.
How his ego hurt him: Frequently posting stories without verifying their truth has hurt him, hurt his credibility, yet doesn't seem to have affect his popularity.
How their egos helped them: Reading this using Firefox? Someone sent you the link from a Gmail account? Stumbled home this AM with the aid of Google Maps? The Google guys have a more insidious reach into your online nethers than your untrusting girlfriend, leaving their mark on any and everything their collective billions can buy up and re-brand.
How their egos hurt them: Google search "Google Day Care" as see what comes up for the answer to this one.
How his ego helped him: Mark Cuban made the Guinness Book of World records for the largest e-commerce transaction for the purchase of a $40 Million dollar jet. Not bad, sir, not bad.
How his ego hurt him: Borderline illegal activity. Cuban's site Sharesleuth.com investigates shady companies then they make money when Cuban takes position in the shares of the companies he investigates before publishing damning information about them.
How his ego helps him: Who's list? Craig's List. By making pretty much every function of Craigslist simple and free, Craig Newmark created one of the most popular and useful websites to date.
How his ego hurts him: Ebay and Craigslist were started roughly around the same time, the founder of Ebay is now worth $7.7 Billion. In comparison all of Craigslist earned a measly $80 million in 2008.
How his ego helped him: He became one of the richest people in the world by playing Robin to Bill Gates Batman. Now, with Bill Gates focusing on charity, he finally gets to drive the Bat mobile.
How his ego hurt him: Before "Chocolate Rain" and Lolcatz, there was "Dance Monkeyboy."