Ever wonder how much computer-book publisher Tim O'Reilly gets to flap his mouth at conferences about how everything should be free? His flack revealed it to the world last night via Twitter (of course).

The economy might be imploding, but Tumblr is RICH! The microblogging service/hipster nerve center raised $4.5 million in a round led by Union Square Ventures and Spark Capital, which means the company is worth $15 million, on paper, even though it doesn't make any money, at all. But next year it's going to start…

Jason Calacanis, the mop-haired founder of Mahalo, an overfunded Web directory, is musing on Twitter about "tickers and rallies past" — a Proustian substitution of stock markets for madeleines. But what, exactly, does he have to be nostalgic for?

"It pretty much is a perfect analogy. It's functional, rational and logical. But it looks like shit and I don't get it." So says photographer eyeliam of the carved-ice vodka tap at Microsoft's Web 2.0 Expo party last night. Care to improve the headline? Write a new one in the comments and we'll replace it with our…

Putting the "social" in "social media" are Tacit Knowledge VP Oz Sultan, left and Yerba Buena Center Webmaster James Im, right — with both mauling online marketeer and TechSet party cohost Stephanie Agresta, center. They were probably trying to kiss their way to free drinks, since the cash bar was charging $9 for…

Fred Wilson of Union Square Ventures carrying his own lunch order from Shake Shack in Manhattan's Madison Square to a group of tables where he was entertaining wantrepreneurs in New York for the O'Reilly Web 2.0 Expo. Not pictured: Lane Becker, president of online customer-service startup Get Satisfaction, who kept…

O'Reilly publishing has set up the company's annual bazaar of of bizarre business models at the Javitz Center in Manhattan, but the festivities truly kicked off with last night's Ignite PowerPoint presentation spectacular hosted by O'Reilly Radar's Brady Forrest and Etsy's Bre Pettis. Pettis and friends used…

Weary of the ad-supported world of Web 2.0? Outside the echo chamber of Silicon Valley, there are software developers who write code that won't change the world, but that customers will pay real, five-figure license fees for — enough to sustain a growing, private business. It's all about finding a market that works…

MTV has decided to try the novel strategy of actually running some music videos on their network, something that hasn't been seen there since the inception of The Real World. But they've added an annoying, faux-modern twist in their new show FNMTV (ha): not only will they show music videos, they'll provide a place for…

What if Facebook let you properly express your rage against the tool who just added you to the "Buying and Selling Friends" app? What if Netflix knew you'd skip to the dirty bits? I paid Jay Hathaway a slave's wage to draw up what this would look like.

Country music singer (and former Renee Zellweger husband) Kenny Chesney was "honored but upset" to win the Academy of Country Music's Entertainer of the Year Award for the fourth time. Why? Because this year, it was someone's idea to decide the thing by a freaking online vote, instead of by Academy members. That's…

In Silicon Valley, it's all about keeping score. The question entrepreneurs are asking about Sarah Lacy's Web 2.0 book: Am I in it? And how many pages? Michael Wolff's chronicle of the first Web bubble, Burn Rate, had a clever conceit: The index was published online at burnrate.com, driving people online to see if…

Remember Amanda "Rocketboom" Congdon, that thing with boobs that did stuff on the internet and parlayed her success into a job at ABC News? Yeah neither do I. Well, whoever she is she lost her job at ABC because nobody cared and she's now returned, sad little pink hat in hand, to the internet. She's launching a new…

CollegeHumor cofounder Ricky Van Veen has decided to short the word "douche."

Cube-dwelling funny pages favorite "Dilbert" from Scott Adams has a redesigned website, sporting the now-ubiquitous "beta" label, offering widgets and buying into the user-generated content fad — you can now create "mashups" and work out your own corporate-minion frustrations within the confines of speech bubbles. […

It's starting to feel like 1988 around here, and not just because Rick Astley is back in the news. No, it's because old analog-like tech is making a virtual comeback online. Muxtape, the latest project from Vimeo's Justin Ouellette, allows aging alt-rockers and hip-hoppers to create mix tapes for their crushes like…

"And you make money for that?" is the first question I get when I tell my extended family about my life as a professional sweatpants-wearer. I'm not too good on the numbers, but some bloggers do get paid and apparently quite well. I think it has something to do with page views? This amazing AP clip about bloggers who…

Yesterday, I very earnestly asked who you commenters are and what you get out of the whole commenting experience. Except for a few people who fairly criticized me for just trying to drum up comments, almost everyone responded with equal earnestness. For the most part, people seem to just enjoy the community in the…

I've never used, or even felt anything approaching ZOMG until I heard that Facebook was launching a chat program. According to Wiktionary, ZOMG is an "overzealous typo of OMG, resulting from the proximity of z to the shift key." That sort of reminds me of the Facebook group, "I Prematurely Release The Shift Key!!1",…