The Social

Twitter just closed a massive funding round that reportedly has given it a billion-dollar valuation. Meanwhile, co-founder and chairman Jack Dorsey is making investments of his own: he's one of the undisclosed angel investors in geolocation start-up Foursquare, quite a few sources have told CNET News.

News of the New York-based Foursquare's venture round, led by Union Square Ventures, leaked earlier this month via an SEC filing. A source with knowledge of the deal's terms said that about $200,000 of that $1.35 million in funding was taken up by the angel investors, including Dorsey, but that there are quite a few hats in the ring so none of them has a particularly huge stake in the company.

Foursquare's executives have chosen to keep the names on the list quiet.

Twitter and Foursquare already have an investor in common: Union Square Ventures, which participated in Twitter's Series A and B rounds but sat out on the most recent one. AllThingD's Peter Kafka speculates that a $100 million funding round may have been out of the question for Union Square, which specializes in early-stage investments.

Jack Dorsey, meanwhile, was Twitter's inaugural CEO, but stepped down in favor of fellow co-founder Evan Williams, a more seasoned tech industry veteran, about a year ago. Dorsey remains an important face of the company even as he works on his next company, reportedly a mobile payment gadget start-up code-named "Squirrel."

A source with knowledge of New York's start-up scene says that Squirrel's real name will actually be "Square." No relation to Foursquare. We think. (Dorsey wasn't immediately available for comment.)

Side note: Squirrel, or Square, or whatever its final name is, may be headquartered in New York rather than the Bay Area. That may have been what set into motion some erroneous rumors this month that Twitter itself would be relocating to New York. Twitter's definitely hunting for new office space to house its rapidly growing workforce, we hear, but it's staying in its home city of San Francisco.

But back to Foursquare. What's interesting is that Twitter's application program interface (API) will soon expand to include geolocation data, something that could potentially make it compete with the core business of Foursquare--a tiny start-up that was basically built from the ashes of ill-fated Google acquisition Dodgeball and launched this year at the South by Southwest Interactive Festival. Dorsey's investment is obviously personal, not on behalf of Twitter, but now he's got a stake in both companies' success.

UPDATE at 8:26 a.m. PT: This post was updated to clarify that the name of Dorsey's new start-up may be "Square."

UPDATE at 12:16 p.m. PT: Business Insider reports that veteran angel investor Ron Conway is also one of Foursquare's numerous individual investors.

Ashton Kutcher at the Brainstorm conference earlier this year

(Credit: Ina Fried/CNET News)

Everybody panic!

Seemingly unable to let any hot social media start-up escape his hunky clutches, it appears that actor and prolific Twitter oversharer Ashton Kutcher is now using where-you-at, ping-your-friends city guide app Foursquare. A tipster pointed me to a Foursquare account for user "aplusk," the same handle that Kutcher uses on Twitter for his 3 million-plus followers.

Is it real? Well, his friends include Digg founder (and occasional bromancer) Kevin Rose, videoblogging personality Justine Ezarik, and "mrskutcher," which is the Twitter username for his wife, actress Demi Moore. Since Foursquare requires mutual approval of friend connections, this would indicate that the likes of Rose and Moore believe the account to be legit. And since Kutcher's Twitter account is linked to the Foursquare profile, which requires using the Twitter log-in credentials, it's either legit or Kutcher's Twitter account has been hacked. (And there have been no indications as to the latter.)

So why is this important? Well, it could be pretty momentous for Foursquare if Ashton Kutcher sticks around.

All joking aside, the 31-year-old Kutcher has been a prominent, and admittedly important figure when it comes to bringing social-media tools into the mainstream. His race to beat CNN to 1 million Twitter followers (he won) was one of the publicity blitzes that put the name of the microblogging service on the pop-culture map. Foursquare, a tiny New York-based start-up that launched only six months ago out of the ashes of the ill-fated Dodgeball and still hasn't wrapped up a round of venture funding (though I hear they're working on it) could really get a boost from this--assuming their servers are ready for it.

But it also raises an important security question. Unless they're using Foursquare to broadcast their locations for promotional purposes (as some party photographers and DJs in NYC are already doing, and it'd be certainly interesting if Kutcher did something like this), celebrities using any kind of GPS-based or geolocation app could be making themselves vulnerable to varying degrees of annoyance ranging from pesky fans with cameras to full-on stalking. It could also make Foursquare an appealing target for hackers.

But I assume Kutcher, who seems like a pretty smart guy, will be careful with who he lets onto his friends list. Now for the real question: how long before he unlocks a "Crunked" badge?

UPDATE (1:06 p.m. PT): Just to clarify, a few people were under the impression Kutcher had already deleted his Foursquare account. That was actually due to a broken link in this blog post; Kutcher is, for the time being, still on Foursquare. (My bad.)

On a completely different note, I recommend reading this follow-up post on branding consultant Matt Spangler's blog about what Ashton Kutcher means for Foursquare.

Seriously, how much is Facebook worth? It's been an enigma in tech gossip for years now, as the social-networking company grows bigger and bigger and yet remains privately held. And some of Facebook's most rapid growth has taken place in the midst of a stormy economic climate that could batter any company's balance sheet. So here's a rundown of what tech blogs, news outlets, investors, and Valley gadflies have said thus far about just how much Facebook is worth.

Are all these numbers accurate? In a word, no. Some of them were rumors (albeit decently strong ones, as we've omitted some of the more ridiculous ones), and others refer to Facebook's preferred-stock valuation, which as we learned during its legal tiff with onetime rival ConnectU, that isn't necessarily anywhere close to the company's paper valuation.

One thing that's interesting: Take a look at the trajectory. Facebook's perceived valuation keeps climbing and climbing and climbing right up to its $240 million investment by Microsoft. Then, once the hype dies down (and the market starts to sputter) it tanks. It's not until, perhaps not coincidentally, the departure of chief financial officer Gideon Yu and the stronger likelihood of a new investment round that Facebook's valuation starts to climb again.

What's next? Digital Sky Technologies' investment in Facebook assumed a preferred-stock valuation of $10 billion, and employee stock trades have started at about a $6.5 billion valuation. It's not yet clear how much more the company's worth will fluctuate before, at long last, founder and CEO Mark Zuckerberg and his team decide to take it public. That is, of course, assuming that actually happens.

It's like a splashy celebrity drama: according to PaidContent, AOL subsidiary TMZ.com will no longer use AOL to sell its ads and instead will be taking those operations in-house. Television ads will be handled through Telepictures, the Time Warner division that teamed up with AOL to launch TMZ in the first place.

The reasoning, according to PaidContent, is that the Hollywood news and gossip site--which was the first to break the news of Michael Jackson's death--has simply gotten too big for AOL's Platform-A technology. TMZ has been one of AOL's foremost success stories of late, and has served as an indicator of how the once-mighty tech company could reinvent itself as a successful digital publishing power under the auspices of new CEO Tim Armstrong.

This could be a messy breakup on the ad sales front. AOL is in the midst of being spun off formally from Time Warner, with which it became joined at the hip in a massive 2000 merger. Platform-A has gone through one management change after another, and though it has significant reach across the Web, still struggles for legitimate industry cred when it comes to both Silicon Valley and Madison Avenue.

Losing a major player like TMZ will be another blow to Platform-A's image. The bigger question will be whether, as PaidContent suggests, TMZ itself may spin off from AOL--something that seems ludicrous, given AOL's plans to be a digital-age Conde Nast or Time Inc.

But things might actually be simpler: as a PaidContent commenter noted, TMZ might be hunting for advertisers willing to work with content a little bit racier than the family-friendly AOL norm. You know, like hard-hitting investigative reports about just how see-through Megan Fox's outfit was at some L.A. nightclub the other night.

Memo to Twitter: If you're really going to be making money with sponsored direct messages, as a New York Times article hints, please make sure it doesn't get annoying.

Twitter investor Todd Chaffee of Institutional Venture Partners told the Times that "e-commerce, including links to products and turnkey payment mechanisms, is a likely revenue stream for Twitter." That's not too surprising. Some companies have touted real success with Twitter-only deals: electronics manufacturer Dell, for example, says it's racked up a few million in sales. Airlines JetBlue and Southwest sometimes advertise special fares on Twitter. It's pretty logical that Twitter would want a slice of this; the catch for the company's team would be how to charge for this sort of thing without taking away features that are already offered for free.

The bigger challenge, however, is not making it annoying. The other day I posted to Twitter about difficulties with my iPhone. I appreciated getting responses from people who were able to inform me that all I had to do to keep my iPhone from skipping songs was to turn off the "shake to shuffle" feature that's new in the iPhone 3.0 software, but I'm not sure if I would want quasi-unsolicited offers from tech support outlets or the like popping up as direct messages in my Twitter feed. Twitter would have to tread very carefully if it plans to be this intrusive--many people receive direct messages as SMS, for example.

Now, there's reason to take the whole thing with a grain of salt, because "sponsored messages" are just the latest potential Twitter business model we've heard about from people affiliated with the service. Last we heard, Twitter was going to be offering some kind of analytics or customer relations management suite for businesses that want to use it more effectively. There have been whispers about search ads, too.

So maybe, when it comes to business plans, Twitter is pretty much throwing ideas at the wall and seeing what sticks. Especially since Twitter co-founder and CEO Evan Williams left a comment on a Business Insider post about Chaffee's remarks that make the whole thing seem much less likely.

"To be clear: Todd is a Twitter investor and a very smart and helpful guy," Williams wrote. "However, he is not actually on Twitter's board and, in this article, he's brainstorming on his own. These are not in the least bit concrete plans of the company."

But if we want to turn to the "juicy gossip" side of things, consider this: Twitter's executives have been very laissez-faire about allowing the users to shape the service before determining the best way to make money off it. Seems like its investors might not be in the same camp.

John Mayer's deep thoughts on Twitter.

(Credit: Twitter)

So I once went on a movie date with a guy who thought it was sort of weird that I posted to Twitter about the movie in mid-date. In retrospect, it probably was weird, and a bit rude, and I wouldn't do it again (and no, there was no second date). But get a load of this one.

Sources quoted in Star magazine and rehashed by the U.K.'s Telegraph (we can tell this anonymous source is just rock solid) claim that the highly publicized relationship between pop singer John Mayer and actress Jennifer Aniston fizzled because of the evil forces of...Twitter!

"People claiming to be friends of (Aniston) have told Star magazine that she finished the affair after discovering Mayer, 31, spent hours on the networking website, despite telling her he was too busy to get in touch with her," the Telegraph report alleged.

Mayer has become an extremely avid user of the microblogging service (username is @johncmayer), along with fellow celebrities like basketball player Shaquille O'Neal, comedians Jimmy Fallon and John Hodgman, and actor Ashton Kutcher (who famously got his wife, actress Demi Moore, to join Twitter as well).

But now it looks like the celebrity Twitterers may be getting a glimpse of what many of us in the tech industry know already: Chronicling your life in constant 140-character updates doesn't leave much wiggle room once you've gotten used to always telling the world what you're doing. I'm sure more than a few people have gotten in trouble because they Twittered about watching sports at a bar when they'd informed their bosses that they were holed up in bed with the flu.

A concluding note to John Mayer: Look on the bright side. At least this time the tabloids aren't blaming a breakup on infidelity, drug addiction, or the failure to disclose a venereal disease. I know plenty of nice, smart girls who wouldn't mind a Twitter-addicted beau.

I don't think I can come close to beating Kara Swisher's headline at All Things Digital, "Is Wonderwall Gonna Be the One That Saves MSN?"

So I'll just cut to the chase: in a move that seems to be way, way, way out in left field, Microsoft's MSN division has partnered with media company BermanBraun to launch an entertainment news site called Wonderwall.

Geared toward a slightly more highbrow breed of entertainment fan than the Perez Hilton set, Wonderwall primarily aggregates content from other entertainment sites but has an editorial team spearheaded by pop-culture veteran Alex Blagg. (He's on Twitter, natch.)

The launch of Wonderwall comes right before Sunday's Grammy Awards ceremony. It also happens to be timed perfectly to fit two high-profile celebrity scandals, the Michael Phelps up-in-smoke fiasco and the Christian Bale audio freakout.

So--why? Well, big tech players seem to want to have an in-house celebrity news hub, for one reason or another. Time Warner's AOL has the hugely successful TMZ, Yahoo has OMG (and indeed, the interface looks a bit like OMG), and Google has...um...the "entertainment" section of Google News.

And despite this whole "advertising recession" thing, we've seen big tech companies increasingly investing in ad-supported content. Perhaps as blog networks find themselves strapped for cash and print media companies find themselves smacking into financial icebergs, the tech companies see a potential gap in the market.

AOL rolled up all its content properties into a conglomeration called MediaGlow recently. We can only wonder if MSN's Wonderwall is the start of something similar in Redmond.

In what's probably one part prank and one part ironic statement, New York society-pages site Cityfile announced Friday that over the past few months it has been quietly snapping up domain names corresponding to the people it covers.

You may not have heard of many of the people on the list: the obsessively name-dropping Cityfile's terrain is more focused on Gotham's business and media leaders than the likes of Britney and Paris. But among those on the list are Warner Music chief Edgar Bronfman Jr. (Cityfile now owns edgarbronfmanjr.com), Greycroft Partners' Alan Patricof, and Nerve.com founder Rufus Griscom.

Domain name speculation has been the subject of much debate for over a decade now, but the gossip site doesn't plan to simply hoard them (and there's no indication yet as to whether the site plans to sell them back to the notable people in question at a premium). The domain names now redirect to the celebrities' Cityfile-created profiles, which are rather comprehensive listings of all sorts of both savory and unsavory details pertaining to the person in question. That means more traffic--and ad revenue--for Cityfile itself. Quite shrewd of them. But there's also an ironic twist to it.

"Given the lengths to which prominent New Yorkers go to control their public profiles, you'd think they would have purchased their domain names by now," the site explained. "It's a $4 investment, which we're pretty sure billionaires like Jonathan Tisch, Steve Feinberg or Edgar Bronfman, Jr. can afford, even if this is the greatest depression ever."

Three words: Ha, ha, ha.

On the same day that he published a detailed missive about his dire predictions for the online ad market, Gawker Media overlord Nick Denton made public his decision to shut down Valleywag, the blog network's Silicon Valley gossip title. Valleywag was launched early in 2006.

Valleywag editor Owen Thomas will have his job folded into a column on the Gawker.com flagship title, a gossip blog focused primarily on the New York media industry. Denton explained in an e-mail to CNET News that Thomas will remain full-time and that the Valleywag brand (as well as Valleywag.com) will stay alive.

Presumably, this means that Thomas' posts will be syndicated to Valleywag.com even though their chief destination will now be Gawker.com.

A recession seems like a great time to be running a gossip blog about the tech business, given all the juicy photos of sad, laid-off employees and rumors of badly-behaved CEOs mismanaging their companies that inevitably fly around. But the reason for Valleywag's shutdown was Denton's notoriously doom-and-gloom vision of the future--Internet ad spending will decline a full 40 percent, he predicts--and Valleywag was one of the company's less lucrative titles.

"Valleywag's traffic isn't enough to pay for two writers, even with Ketel One ads on every page," wrote Valleywag senior writer Paul Boutin, who will not stay full-time at Gawker Media.

It was a tough sell for advertisers, given its niche audience, and many tech companies would be hesitant to advertise on a publication dedicated to ridiculing tech companies. And then there was the fact that you just can't turn the average Valley exec or VC into a Perez Hilton-style celebrity. The likes of Mark Zuckerberg, Peter Thiel, and Elon Musk simply don't add up to Britney Spears-like followings.

Reactions in the tech community will probably be mixed. Valleywag is mean, to be sure, but it can also be hilarious, and writers Thomas and Boutin were tech-press regulars long before their Gawker gigs.

Denton's handling of Gawker has been frugal, continually consolidating resources toward the blogs that were pulling in traffic and ad dollars and not hesitating to shut down the underperformers. In April, Gawker Media sold off three of its smallest blogs, and Denton has now announced that another, Consumerist, is on the block.

Early in October, Denton orchestrated a personnel shuffling that saw 14 percent of the company's editorial staff laid off but new hires made at some of the most successful titles like gadget blog Gizmodo and feminist chronicle Jezebel.

Also on Wednesday, AllThingsD's Peter Kafka reporter that Gawker Media managing editor Noah Robischon was leaving for Fast Company.

This post was expanded at 11:51 a.m. PT on Thursday.