The New Yorker has a long and interesting (to me!) profile of Nick Denton, enigmatic impresario of Gawker Media, the blog company that publishes (in order of reported popularity) Gizmodo, Gawker, Lifehacker, Kotaku, Deadspin, Jezebel, io9, Jalopnik, and [NSFW] Fleshbot. Even if none of those sites floats your boat (though seriously: Brett Favre penis!), the article's discussion of 21st century publishing, examination of the entrepreneurial mindset, and journalistic genealogy with Spy magazine, are thought-provoking for those who are into such things.
I've been friends with Denton since the late '90s (I'm quoted in the piece for mostly semi-comic effect), so take the following with a grain of salt, but I think no other media figure has been more important in exposing three fundamental pathologies of turn-of-the-century American journalism: It was deathly boring, it grossly undervalued writing talent (especially eccentrics), and it didn't take proper advantage of the Interwebs. Also, I like this quote:
"If you're running Spy, at some point you have a choice: do you want to be the cute, unprofitable, ultimately doomed niche publication, or do you want to create something that's viable and lasting?" Denton said. "I didn't like the story of Spy. They failed."
Since the mic is on, one microscopic clarification that maybe two people in the world will care about: Former Hungarian parliamentarian Peter Molnar, who wrote his country's media law in the '90s (which I covered) and co-taught a Berkeley journalism course with Denton in the aughts, is described as sounding "less frustrated than nervous" when talking about Denton ("I don't want to say negative things about Nick"). But Molnar always sounds nervous. The end.