The demise of Conde Nast's scrapbook site for teenaged girls, Flip.com, was a reminder. How is that other big website launch of 2007 going? 23/6, a joint venture between Barry Diller's IAC and Kenny Lerer's Huffington Post, was two years in the making. The political humor launched in November to lackluster reviews; but maybe it's caught fire since, what with the elections and all. Who are we kidding? A quick search on Compete.com shows 23/6 is as stillborn as Time Inc's Office Pirates, Viacom's Virtual Lower East Side — and every other site that springs from the loins of New York's media titans. They really should have read The Innovator's Dilemma, that standard reference book for young-at-heart moguls, more carefully.

Working for Barry Diller is a harrowing experience. Just take a look at Jim Lanzone, the former CEO of Ask.com, before he joined IAC, and after. Even so, we're reconsidering our sympathetic view of Lanzone. We hear that one big reason he was fired was the slipping schedule on an Ask.com news site. Despite putting 20 people nearly full-time on the project, and getting help from Digg, Lanzone missed a December deadline for the site, now slated for a February launch.

Are New York's established media companies entirely incapable of developing web properties? Barry Diller's IAC just fired the head of Ask.com after the search engine's obscure "algorithm" campaign failed to eat into Google's lead among web users. Now, word that Conde Nast is laying off staff on Flip.com, a social network for teen girls which was the magazine group's biggest greenfield web initiative. Flip.com attracts less than 20% of the audience it had last April. The new plan, we hear: let Flip scrapbooks be embedded in other more successful West Coast social networks such as Facebook and Myspace. This is what New York media is reduced to: a widget. (Anyone have the Flip.com layoff email? Forward it me!)

Bloody Diller. IAC's Ask.com has a new CEO, Jim Safka, who was swiftly installed in the place of Jim Lanzone. Lanzone was fired by Barry Diller, according to sources. And so yet another talented entrepreneurial type makes way for a Diller yes-man. The cover story is that Lanzone left to accept a position as entrepreneur-in-residence at Redpoint Ventures — a cozy, face-saving sort of holding tank for CEOs in between jobs.

Primal Ventures, IAC's corporate venture arm, is "gearing up to launch a new child-oriented portal and interactive entertainment company," according to a job listing on DevBistro. Sounds like Barry Diller & Co. are developing a virtual world targeted to children, joining Viacom, Disney, Warner Bros., and just about every other media company on the planet in following the trend started by Webkinz and Club Penguin. Imagine that: An unoriginal, me-too Internet project, coming late to the party, from Barry Diller. (Photo by Getty Images)

Not only has Barry Diller exiled his former IAC No. 2, Doug Lebda, to LendingTree; he's officially washing his hands of Lebda's company. After he finishes splitting IAC into five parts, Diller plans to stay involved only with the new IAC and Ticketmaster, as well as Expedia, the online travel agent he spun off in 2005. A source close to Lebda believes he's just as glad to be through with Diller.

Left in the wake of Barry Diller's acquisitive empire: a flotsam of discarded executives. Doug Lebda, IAC's president and COO since 2003, now joins them. According to an internal memo obtained by Valleywag, Lebda has been appointed CEO of IAC's mortgage and finance businesses, which are soon to be spun off. This can hardly be welcome news to Lebda, who's essentially returning to LendingTree, a business he founded in 1996 and sold to Diller in 2003. Here's the memo.

Julia Allison, the ex-girlfriend of Jakob Lodwick, agreed to chat with her sadmirers on sister site Gawker. In the comments, she revealed the real reason why the attention-seeker was fired from his own company Vimeo:

Amateur attention seeker and entrepreneur Jakob Lodwick may be releasing a new project soon with David Karp, the creator of blogging tool Tumblr. Lodwick recently cut ties with both his beau, Julia Allison, and Connected Ventures, the startup he founded, now controlled by IAC and best known for Vimeo and College Humor. Without Barry Diller's backing or Allison's cleavage, how will the pasty, shirtless hipster generate the buzz he's grown to expect but rarely deserves? By mocking the homeless.

The herd of day traders is debating whether to buy Apple before Steve Jobs's keynote at Macworld Expo. But following the herd is a strategy that generally leads to getting trampled. Eric Savitz of Barron's spots a smarter strategy: Buy Amazon.com, and sell — or at least avoid — Barry Diller's IAC. Citigroup analyst Mark Mahaney says IAC has "few countercyclical hedges to protect against a potentially material economic slowdown in the U.S." What does that mean?

At last, an explanation for the renewed rumors of a Digg sale. Digg has hired Allen & Co., the boutique investment bank which specializes in media deals, according to VentureBeat. Which makes sense, since Digg CEO Jay Adelson got an invite to this year's exclusive Allen & Co. conference in Sun Valley. The wave of buzz about a Digg sale is likely explained by Allen bankers' discreet inquiries. The company, as we'd heard, is seeking a price tag of $300 million. One possible acquirer, IAC, which had previously expressed interest but has backed off before. One reason for the renewed interest now: We hear that Barry Diller's online conglomerate is secretly working with Digg on some kind of project — possibly a white-label version of Digg's social news site. (Photo by Lane Hartwell)

In Silicon Valley, VCs talk about building wealth for your great-grandchildren. But for Manhattan's tech entrepreneurs, success is measured by being able to immerse yourself in bubbly water at home. Connected Ventures cofounder Ricky Van Veen — yes, one of those "silly kids" in New York I cover way too much — just bought a new pad. Paul Boutin's response: "Who?" Owen's: "Wake me when you have photos of Mark Zuckerberg's new condo at the Ritz." Whatevs. Check out the hot real estate porn.

The television and film writers' strike over Internet pay was supposed to be a boon for Internet-only content creators. But according to CollegeHumor cofounder Ricky Van Veen, that's not been the case.

Connected Ventures cofounder Zach Klein did fly out to California to interview for a gig at MySpace, but it wasn't the right fit for him. Or he wasn't the right fit for MySpace. Hard to tell which. So what's the designer behind BustedTees and Vimeo up to next? Think geckos and real estate.

Barry Diller likes to talk up how New Yorky his Manhattan-headquartered IAC is, but in fact, his most important online businesses are based in California, like Ask.com. San Francisco-area IAC workers are having their holiday party tonight at the Independent, 628 Divisadero St. "Bonus points to anyone who videos themselves gaining entry as Vimeo staff wearing their best American Apparel hoodie and art-skool glasses," says a Grinch of a tipster.

IAC, after it spins off all its boring businesses like HSN and LendingTree, will be left with a motley collection of questionably successful startups with so-cute-you-could-pinch-them names like Vimeo and Zwinky. In an interview with the New York Observer, Diller saves special favor for Very Short List, a daily email newsletter which sells one thing a day, with just two employees. Think of it as a Woot.com, but for aging billionaires. He claims to have bought 30 items off the list. "Without Very Short List, I would be much diminished," Diller tells the Observer. But as the newspaper points out, IAC's market cap has shrunk from $22 billion in 2003, before it spun off Expedia, to $8 billion today. A bit too late for an email to stop his diminution, I think.

IAC-owner and New Media Mogul Barry Diller went from the man who created the Fox network and greenlighted The Simpsons to the dude who owns Zwinky.com. He's still filthy rich and owns the biggest yacht ever and never needs to leave his gigantic office atop his Frank Gehry castle, but his former boss and current sorta-rival Rupert Murdoch just continues amassing power and influence and Presidents while Diller is creating and buying little funny (but sometimes hugely profitable!) websites. Does that bug him? According to a profile by the Observer's Doree Shafrir... maybe?

Put your tinfoil hats back on, folks. IAC's search engine Ask.com has announced a new feature called AskEraser, as expected. It's supposed to be a privacy control allowing users to delete their queries from Ask's server logs, a move meant to set Ask apart in the market. But it won't really do either. Like Ask's television commercials, AskEraser is at once ineffective and confounding. Here's why.

Here, in an October video, ousted Vimeo cofounder Jakob Lodwick explains how Connected Ventures keeps the office young. His opening thought is the kind of thing that's best both read and viewed. So, here. For your pleasure.

Rumor is Julia Allison is on to her next geek, Connected Ventures cofounder Ricky Van Veen. But don't worry, the family's fine. Van Veen is pictured here with his significant other and some girl. "Her name is Anna," Van Veen tells me. "And before she was my girlfriend, she was a model for our T-shirt site, BustedTees." We're not going to see a RickyandAnna.com anytime soon, are we? "We shall not," Van Veen says. Promises, promises.