Union Square was the lead investor in Twitter’s first funding round in July 2007, and participated in subsequent rounds in May 2008 and February of this year. In that last round, Union Square said it was re-upping “to maintain our ownership position.”

What happened this round?

Union Square partner Fred Wilson, who is a Twitter board member and a tireless Twitter advocate (and Twitterer) declined to comment. So I’ll hazard an Occam’s Razor guess: The $1 billion valuation that Twitter achieved in this round priced out Wilson’s fund.

If that’s the case, it’s a high-class problem to have. Union Square is a relatively small venture player (the two funds it manages have a total commitment of $281 million). It specializes in early-round investing in which the bets are comparatively low stakes–a few million dollars here and there. If things go well, those bets are enough to get the company to an exit–in the old days, that meant an IPO, these days, a sale to Microsoft (MSFT), Yahoo (YHOO) or Google (GOOG).

But as the valuations increase, so do the amounts a start-up’s investors need to pay to keep their ownership stake, which is why angels and other early investors usually drop away. A player Union Square’s size can play up to a point, but then has to step aside or it would end up with most of its portfolio invested in a single company.

In order to re-up at this level, Union Square would have needed to make a much larger bet than it is used to making, and perhaps more than it is able to make. The new round, which raised $100 million, is nearly twice as much as the $55 million Twitter had raised to date. Which means Union Square’s bet would likely have to double as well.

[Image credit: Steve Jurvetson]

Even when the M&A market was shut down, Wall Street couldn’t stop speculating about GE’s intentions for its NBC Universal unit. And now that it’s deal-making time again, the chatter is getting very noisy.

Hence the flurry of coverage over yesterday’s remarks by Vivendi CEO Jean-Bernard Levy, in which he said…not very much.

But even Levy’s noncomments are important, since his company may have a good deal to say about the fate of NBCU. That’s because Vivendi owns a 20 percent stake in the company, and it looks increasingly likely to sell this year. And that could trigger a whole series of moves. The Wall Street Journal:

Vivendi, the Paris-based entertainment conglomerate, has an annual option to unload its NBCU stake which it is allowed to exercise beginning each November. The option was part of a deal made in 2003 when Vivendi sold its theme parks and television assets in the U.S. to GE for cash and stock.

If Vivendi exercises the option this year, Mr. Levy said, it will plan to offer the shares in the public stock market unless GE exercises its right to buy the stake.

If Vivendi says it will exercise the option this year, GE would have nine months to pony up an estimated $4 billion to $5 billion if it chooses to buy Vivendi’s stake at a time when it already is struggling to shore up its financial position. Otherwise, Vivendi’s minority stake in NBCU could be put in play, raising a host of potential complications for GE’s ownership of the media company.

Yet another option: GE (GE) and Vivendi work together to sell off all of NBC via a direct sale–Comcast (CMCSA) and Time Warner (TWX) are the names you always hear as obvious strategic buyers, though I’m not sure that’s the case–or even via an IPO.

The big picture: Even though Facebook’s official valuation has slid from $15 billion–November 2007, when Microsoft (MSFT) invested–to $10 billion, Zuckerberg is OK with that, arguing that 1) that deal was done at the peak of the market and 2) the pact was never really a financial deal, but a way for Microsoft to partner up with Facebook–and, though he didn’t say it, to box out Google (GOOG). That sounds pretty reasonable.

Zuckerberg’s main talking points were that his company didn’t need the money, but it sure was nice to have, both to fund growth and make any M&A easier to pull off. And when it came to his new partners, he argued that DST’s existing portfolio, which includes several other social networks, would provide models/examples for his company as it continued to expand outside the U.S.

Earlier:

Facebook and its newest investors Digital Sky Technologies, are holding a teleconference to discuss the $200 million at 10 billion valuation deal the two parties just announced. I’ll be covering the call live.

Call starting “momentarily.”

On the call: Facebook Mark Zuckerberg, DST CEO Yuri Milner. Also, via phone (from D7!): Facebook COO Sheryl Sandberg and DST’s Alexander Tamas.

Zuckerberg reading statement that more or less tracks press release: “Advertising product” improving, “our business is doing really well” and we’re on track to create a “nice” business, and that’s why investors want in. DST approached us, has interesting profile and experience and insight into social networks. “We found their thinking and their leadership to be really impressive.”

Money provides “cash buffer” to support our continued growth, also possible other moves. No specific plans to talk about “but nice to have flexibility.”

Milner: “I realize not all the participants on the call are familiar with us.” Goes over DST portfolio. “We have now started to actively expand abroad.” We’re a holding company, have raised and invested more than $1 billion since 2005. Rattling off portfolio companies now.

Q&A:

What does this mean for possible IPO? Zuckerberg: “Our approach to financing has really been that we want to take money and work with partners”…”for a lot of start-ups, you get the feeling that the IPO is really the end goal…that’s not the case for us…we’re not rushing toward it…that’s really all I have to say about that today.”

What’s valuation for common stock? Zuckerberg: No comment. “There are different transactions that we’ve structured differently…we hope that there will be different things in the future…probably sometime in the next few months.”

What does this say about Microsoft’s $15 billion valuation? Zuckerberg: We did that deal at the peak of the market. That was part of a broader relationship. That investment was just one piece of it. This is also a relationship that we’re forming with DST…we hope we will work with other things over time.

“We feel really good about the progress we made…we feel this is  a good and fair valuation for us.” The Microsoft deal was at peak of market and was a strategic deal. “The world was in a pretty different place at that time.”

The international audience is 70 percent of our users. How do you monetize that? Zuckerberg: I have a few things to say, but want Yuri to talk, too. Milner: We have invested in five social networks in Europe. They have been able to monetize better than Facebook because they’re further along the curve than Facebook, which is a global company. But we think that Facebook will improve. Money will come from micropayments and advertising.

Zuckerberg: We can do advertising and have been experimenting with payments. Social networks in DST’s portfolio all monetize in different ways. Each is doing well, with a different model. We’re still growing. Online and direct advertising are growing the quickest, but over time, we expect to be able to build out a large number of these things.

What is your ad revenue going to be? Zuckerberg: A couple of months ago, we felt that everyone outside the company was underestimating our performance. We’ve been EBITDA-profitable for five straight quarters coming on six. Revenue growth has been 70 percent. Cash-flow positive sometime in 2010. That’s important because it means this investment is pure buffer. I realize those aren’t absolute numbers, but those are the ones we’re talking about.

Will DST be involved in management? Milner: We have our own businesses to run. We’ll keep in touch.

Questions about micropayments. Zuckerberg: We’ve tested a lot of things. It’s not a big part of our business, could be greater one day. They create a lot of value for users, and there are ways to monetize them. I’m looking forward to learning how these models are working.

Please talk about common stock/employee stock purchase plans. Zuckerberg: Going back to first question re. IPO. We want to make sure that we can continually make it so employees can be focused on the long term. We felt that if we let people have a little bit of liquidity, it can take some of the pressure off and let people focus on making company as good as it could be. We started to do this last year and had to hold off. Now we hope to be able to do it again.

Will that be the only way you are allowing employees or ex-employees to sell shares? Zuckerberg: Still talking about.

Is current Facebook ad business to be the main business going forward? Doesn’t mean it will be main business in the long term. You guys know everything that we’re talking about now.

Why aren’t you running big brand ad campaigns? We’re very interested in it. We have a big ad sales team. Building out offices internationally: U.K., France, a few more coming up. We think the best way to serve advertisers is to create ads that people interact with, that are “social and engaging.” I don’t want anyone to think that this isn’t a big part of our business, because it is.

Sandberg: Heavily engaged with brands. Ads specifically designed for Facebook, so they look different and behave differently than other ads on other sites, and that’s a good thing.

Preferred shares–are these are substantially similar to the ones Microsoft bought? Zuckberg: “I’m gonna duck that one.”

Does the company have any debt? Zuckerberg: [pause] There’s been some information that’s been public about debt we have for operating equipment. Beyond that, we do equity deals.

Will you do other investment deals? How many did you look at? Zuckerberg: He doesn’t really answer this question; instead he goes on to praise DST. Milner: We see things that other people don’t see, which is monetization that other social networks have been able to do. So we “kind of feel comfortable with that valuation.”

Is this largest foreign investment in Facebook? Zuckerberg: Um… [pause]. There’s been some public information about other folks we’ve worked with, but I think from reading some of the records you can get the answer to your question.

Other new deals? Zuckerberg: It was really at our option to find someone we were comfortable with. We didn’t feel like we needed to take an investment, and now we feel like we have the buffer we want.

Working on video chat product? More international products? Zuckerberg Yes. There are lots of things like that that we’re working on now. We want the site to be available in every country. We’re not translating the site. Users translate the site themselves. And a lot of the features are universally applicable.

Call finished.

That’s the possibility floated, albeit in an offhand way, via Bernstein Research’s Jeffrey Lindsay in a note published this morning: “We would likely expect further divestments of non-core businesses, possibly including StubHub.”

I understand why the auction site dropped StumbleUpon, a Web 2.0 publishing business with a novel and unproven revenue model. And it makes sense to stop carrying Skype, a telecom business that requires a lot of time, money and maintenance.

But Stubhub, which eBay bought for $307 million a little more than two years ago, seemed like a bona fide fit: The ticket resale business mirrors eBay’s (EBAY) core auction in pretty obvious ways. I’ve asked Lindsay to tease out his thinking for us, and will update if he does.

UPDATE: Here’s Lindsay, via email: “It seems that eBay is going right back to basics, and is dispensing with the ‘we are an auction company’ ethos that got them into so much trouble. We see StubHub as coming out of that era. We think the market in tickets is changing rapidly and there is a chance to sell StubHub at the very top. They might well take it and pursue a much more pure play retail/second hand portfolio and go back to geographic expansion of the marketplaces/PayPal core.”

Meanwhile, if eBay does decide to jettison StubHub, now would be a very interesting time to do so. TicketsNow, its primary competitor, is likely to go on the block in the near future: Parent company Ticketmaster (TKTM), which acquired the business for $265 million a year ago, has said it would dump the business in order to mollify antitrust critics (and Bruce Springsteen fans) who want to stop the company’s proposed merger with Live Nation (LYV).

Anyone want to corner the market on the ticket-scalping industry?

[Image credit: Hyrck]

How about this instead: Some brief reminiscing, via this June 2004 Harvard Crimson article, written “nearly a semester after” 20-year-old Mark Zuckerberg had launched thefacebook.com. At the time, it had 160,000 users.

It’s a great story (thanks to the excellent Nieman Journalism Lab for pointing this out via its Twitter feed), but let’s just zoom right ahead to the end:

Zuckerberg participated in a live television interview for CNBC, and says he has been wined and dined in Harvard Square by representatives from major software companies.

Still, he is maintaining the same approach: don’t sell.

“That’s just like not something we’re really interested in,” he says, referring to selling out thefacebook.com. “I mean, yeah, we can make a bunch of money—that’s not the goal…I mean, like, anyone from Harvard can get a job and make a bunch of money. Not everyone at Harvard can have a social network. I value that more as a resource more than like any money.”…

“My goal is to not have a job,” he says matter-of-factly. “Making cool things is just something I love doing, and not having someone tell me what to do or a timeframe in which to do it is the luxury I am looking for in my life.”…”I assume eventually I’ll make something that is profitable,” he allows.

The site is currently running some advertisements, but Zuckerberg says they are only being used to offset server costs. Nonetheless, the facebook’s business manager has posted notices soliciting ads on multiple websites, and a thefacebook.com rate card shows that the site is interested in attracting national advertisers….

“There are a couple ads on the facebook because [the site] costs money and servers don’t grow on trees,” Zuckerberg says.

But will the facebook ever be auctioned off to the highest bidder?

“Maybe when I’m bored with it, then we’ll work something out,” he says. “But I don’t see that happening anytime in the near future.”

Cool foreshadowing, huh? (Harvard kids! So smart!) But let’s put Facebook’s success in context–by comparing it to Silicon Valley’s most successful start-up of the last couple of decades. Here’s how Facebook today stacks up against the Google of 2003, when that company was 5 years old.

I’ve pulled the Facebook stats from various sources, so please consider them estimates. The Google (GOOG) stats are much more solid: I’ve pulled most of them from the company’s 2004 IPO prospectus.

Facebook:
Workforce: 700+
Revenue: $260 – $300 million
Net income: None (EBITDA of perhaps $50 million)
Valuation: Something in the $4 billion range, based on reports of share sales
Motto: “Facebook is about helping people to share information and share themselves.”

Google:
Workforce: 1,907 (as of March 2004)
Revenue: $962 million
Net income: $106 million
Valuation: Something in the $20 billion range, based on press reports
Motto: “Don’t be evil. We believe strongly that in the long term, we will be better served–as shareholders and in all other ways–by a company that does good things for the world even if we forgo some short term gains. This is an important aspect of our culture and is broadly shared within the company.”

So take a bow, Mark Zuckerberg. You’ve built something really cool. But if you want to keep up with Larry and Sergey, you’d better get back to work.

[Image Credit: deneyterrio]

The answer: It gives it away.

Or at least, that’s what Adult FriendFinder was planning on doing with the Ferrari it bought from founder Andrew Conru. The car was supposed to be awarded to one of the company’s many “affiliates”–tens of thousands of Web sites that refer traffic to Adult FriendFinder for a fee–that won a 2006 “top growth” contest.

Thanks to MediaMemo reader Tommy New for (not so gently) pointing out the contest to me (don’t click on this link unless you’re up for rough language as you read about the online porn business). Another MediaMemo reader tells me that the reason that the company still owns the Ferrari, which was originally valued at $125,000, is that the Web site owner who won the contest took cash instead of the car.

I’m still waiting to hear back from Andrew Conru or Adult FriendFinders’ current management, which just registered the company for a $460 million IPO, to confirm this. But those answers make plenty of sense to me. Affiliates are a key part of the company’s business: It paid out $46.4 million to some 110,000 participants during the first nine months of 2008, according to the company’s prospecttus. That’s nearly 20 percent of its net revenue during that period.

Those payouts are crucial, because Adult FriendFinder’s subscribers, who make up the bulk of its revenues, are always on their way out: Monthly churn hovers around the 20 percent mark. Adult FriendFinder says affiliates help generate about 44 percent of Adult FriendFinder’s business.

Thus, contests and promotions to entice affiliates are standard operating practice at Adult FriendFinder. This month’s contest promises the winner $40,000 and a trip to Los Angeles to hang out with some Penthouse Pets.

So that’s one mystery resolved. Except I still don’t understand why Adult FriendFinder bought the Ferrari from its founder in the first place. I’ll let you know when the company returns my calls.

I still haven’t heard back from FriendFinder Networks or Andrew Conru, who appears to be the founder who sold his company his car in 2006. But MediaMemo readers tell me the car in question is a Ferrari 360 Modena, similar to this model on sale, via eBay (EBAY), at Excel Auto of Boca Raton, Fla. (click image to enlarge):

I thought this car might actually be the same one that FriendFinder owns, since it says the car in question is being held for sale, and because FriendFinder is also based in Boca Raton. But a manager at Excel tells me that’s not the case.

Disclaimer: I need to note that while I appreciate the tips MediaMemo readers have passed along, they remain unconfirmed. So it could be that FriendFinder owns a different kind of car that it purchased for $125,000 two years ago and now values at $95,000.

The bigger question: Why would FriendFinder buy a Ferrari (or any other kind of car) from its founder a couple of years ago? And what has it done with it since? Did employees of the month get to take it for a spin? Has it been mothballed? Did it sit parked in front of the company’s HQ as an incentive to work harder and longer?

(UPDATE: A partial answer — the car was supposed to have been given away as a contest prize.)

As always, if you’ve got thoughts on the matter, you can comment below, or reach me directly at peter@allthingsd.com. If you want to be completely anonymous, you can use the blind tip box here.

But the FriendFinder prospectus may turn out to have multiple Christmas gifts for those who work their way through it. For instance, Nick Wingfield, my corporate cousin at The Wall Street Journal, dug up this gem under “related party transactions”:

In another interesting tidbit, the company says [predecessor company] Various purchased an automobile from the founder of Various for $125,000 on October 27, 2006 (the founder in question appears to be Andrew Conru.) The company doesn’t say what kind of car it is or why it bought it, but it doesn’t appear to have gotten a very good deal. The filing says the vehicle is currently ‘being held for sale and in 2006 was written down to its estimated net realizable value of $95,000.’ A FriendFinder spokesman didn’t immediately return a call for comment.”

I’ve also lobbed queries in to Andrew Conru and to FriendFinder’s corporate HQ, but haven’t heard back. But perhaps MediaMemo readers who are more autocentric than I am (I’ve owned one car in my life–a 1994 Toyota Tercel with vinyl seats and no air conditioning) can help answer one of my questions: What kind of used car can you get for $95,000?

Please share your thoughts with us via the comments section below; if you find the registration process too onerous, you can leave an anonymous comment via the tip box. (UPDATE: Some readers tell me it’s a Ferrari 360 Modena).

In the meantime, I’ve made my own rudimentary attempt to gauge the market for $95,000 cars: A trip to eBay’s (EBAY) Motors showroom. Here’s a sampling of what’s available in the $90,000 to $95,000 range today (click on each image to enlarge).

2006 Bentley Continental Spur. Starting bid: $95,000

2003 Ferrari 575. Starting bid: $95,000

2007 Porsche 911. Starting bid: $95,000

1970 Ford Mustang Boss. Starting bid: $90,000

2004 Lamborghini Gallardo. Starting bid: $95,000

That’s the story behind yesterday’s filing by FriendFinder Networks Inc., a collection of porn sites and adult networks that wants to raise $460 million via the public markets.

Given that the media industry is in the dumps, the tech IPO market was closed even before the economy’s collapse and that the prospects of floating any kind of offering in the public markets is dicey at best, it would be hard to find a worse time to try this route. But FriendFinder doesn’t have much choice: It has very little cash and a lot of debt.

The details: The money-losing company has $43 million in cash, and $420 million in short-term debt. Some of that debt is already in default and the company has breached loan covenants for some loans as well. Presumably the company can’t find anyone to lend it that much, so it’s hoping that the equity markets step up.

If investors bail it out, almost all of the IPO proceeds will go to paying down that debt. If not… well, that “could have a material adverse effect on our ability to continue as a going concern.”

Anyone still thinking about helping out Daniel C. Staton and Marc H. Bell, who run the company and own more than half of its equity? Read the full registration statement here.

[UPDATE: FriendFinder investors get a bonus: Partial ownership of a $95,000 car the company bought from a founder a couple years ago for $125,000.]