The service took one step toward wider distribution today when Apple (AAPL) approved its iPhone app (for a glimpse of the app, see the video at the bottom of this post). But that won’t help U.S. users until the big music labels–Warner Music Group (WMG), Sony (SNE), EMI and Universal Music Group–agree to American distribution deals.

But before we get to that, let’s back up and explain what Spotify is: A streaming-music service that lets you listen to whatever you want whenever you want, as long as you have a Web connection. A free version comes with ads, and if you want to do away with those, you can pay for a subscription.

Does that sound familiar? It should. There are plenty of models like this available in the U.S. right now, from RealNetworks’s (RNWK) Rhapsody to MySpace Music, a joint venture owned by News Corp.’s (NWS) social network and the big labels. For various reasons, equivalent (and legal) models have been much harder to come by in Europe, which explains part of the appeal there. The other explanation is that Spotify works beautifully.

But don’t take my word for it. Ask Slate.com columnist Farhad Manjoo (“The best streaming music service in the world”). Or better yet, Facebook CEO Mark Zuckerberg (“Spotify is so good”).

Meanwhile, investors–primarily European ones–have been throwing money at Spotify, and the big music labels’ international arms are enthusiastic partners (and equity shareholders). And the company’s boosters have been pointing to a U.S. launch as early as the fourth quarter of this year.

So let’s assume this happens. What then? The problem with the digital music business, as company after company has found out, is that it’s a miserable business:

• Selling music by the track is a low-margin affair that only works if you have enormous scale–Apple sells some two billion songs a year.
• It’s been nearly impossible to get more than a few hundred thousand people to pay a monthly fee for music–ask Rhapsody or Best Buy’s (BBY) Napster, which have been slogging away at this for years without gaining any traction.
• And it’s been impossible to support a free service with advertising while ponying up big licensing fees to the labels–ask Imeem, et al.

So why will Spotify be any different? Depends on whom you ask. Some figure that it has the best chance of working as a mobile service and that since phone users aren’t used to the idea of getting all the music they can eat on their phones for free, they’ll pay up if given the chance. Others think the big labels have gotten wiser and/or more benevolent about their licensing fees and are willing to wring less out of Spotify at the start in the hope that it will pay off down the road.

Still others just shrug and figure it will work out somehow because…well, one of these days, someone has to figure out how to make this work. “Everybody loves the product,” says an industry executive familiar with the company’s plans. “And there’s a hope that the business model is realistic.”

I have heard rumbling that not all of the big labels are equally enthusiastic about a U.S. licensing deal. It’s unclear whether that’s due to something specific about the U.S. market or to internecine squabbles at particular labels. But Spotify will need at least three of the big four to play along. And then we can see just how realistic the model really is.

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.

DST will not get a board seat or “special observer rights” in return for its money. The two companies are holding a press conference shortly, so we may be able to extract a few more details.

The $10 billion valuation is comedown from the $15 billion figure that accompanied Microsoft’s (MSFT) 2007 investment, but no one expected that figure to hold up–in large part that deal was driven by a bidding war with Google (GOOG) and not much else.

Facebook and its newest investors are conducting a conference call to discuss the deal; I’ll be covering the call live.

FACEBOOK RECEIVES INVESTMENT FROM DIGITAL SKY TECHNOLOGIES

Passive Investment Includes Stake in Preferred Stock, Common Stock and Support for Facebook’s Continued Global Growth

PALO ALTO, Calif. — May 26, 2009 — Facebook today announced that Digital Sky Technologies (DST), one of the leading internet investment groups globally with significant stakes in Eastern European and Russian internet businesses, has made a $200 million investment in Facebook in exchange for preferred stock, representing a 1.96 percent equity stake at a $10 billion valuation.

In addition, DST has indicated that it is planning to offer to purchase at least $100 million of Facebook common stock from existing common stockholders that would facilitate liquidity for current and former employees’ vested shares in the company. The details of the plan are expected to be announced to eligible participants during the summer. Consistent with Facebook’s practice with other recent investors, DST will not be represented on the Facebook board or hold special observer rights.

“This investment demonstrates Facebook’s ongoing success at creating a global network for people to share and connect,” said Facebook CEO Mark Zuckerberg. “We’ve worked hard to bring more than 200 million people — 70 percent outside of the U.S. — onto Facebook to share with friends, family and co-workers. A number of firms approached us, but DST stood out because of the global perspective they bring — backed up by the impressive growth and financial achievements of their internet investments. We’re looking forward to working with the DST team.”

“Our investment experience in other regions reveals the tremendous value social networking companies create as they redefine how people communicate and interact,” said Yuri Milner, chief executive of DST.  “By every important metric — user growth and engagement, technological innovation and financial performance — Facebook is on a similar trajectory, though on a much more global scale. We’re delighted to invest in Facebook, Mark and his management team as they make the world more open and connected.”

Based in London and Moscow, DST is a well-respected investor in a number of successful internet companies, holding significant interests in Russia and Eastern Europe, such as Mail.ru, Forticom and vKontakte.  DST’s main assets account for over 70 percent of all page views in the Russian-speaking internet and its social networks are the market leaders in more than 13 countries, addressing a combined population of more than 350 million.

DST is run by its three partners who have complementary backgrounds in operations, investments and finance: Yuri Milner, previously CEO of Mail.ru, the #1 Russian language website; Gregory Finger, previously head of the Moscow office of NCH, a multi-billion dollar hedge fund; and Alexander Tamas, previously co-head of internet and software coverage in EMEA for the Investment Banking Division of Goldman Sachs. With its advanced understanding of opportunities in technology and social media, DST is a good fit for Facebook and an insightful partner that can help unlock additional growth opportunities.

Reached for comment, Facebook spokesperson Brandee Barker offered up the boilerplate no comment: “Facebook is a private company, so as a matter of policy, we don’t typically share details about our financial plans or comment on rumor and speculation.”

But everyone else has been speculating about the value that Facebook and outside investors place on the company, and whether Facebook needs to raise any money at all.

We do know that in 2007, Microsoft (MSFT) beat out Google (GOOG) for the right to invest some $250 million in the Facebook, placing a $15 billion valuation on the company’s preferred stock. Preferred stock is typically more expensive than common stock because it gives owners the ability to recoup their money before other investors. Facebook later raised another $60 million from Hong Kong billionaire Li Ka-shing and $10 million or so from the Samwer brothers of Germany.

And various reports have suggested that employees and others who own Facebook common stock have been recently selling it on the private market for prices that value the company in the $4 billion range.

Facebook has repeatedly said that it doesn’t need additional cash to keep going and that it expects to generate $500 million in revenue this year and begin breaking even in 2010. Last year, the company felt flush enough to offer to buy Twitter for $500 million–$100 million of which would have been in cash.

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]

Last week Mark Zuckberg’s company sued Power.com, a social network aggregator, because the company allowed Facebook users to plug into the site without actually visiting Facebook itself. Today, instant-messaging aggregator Meebo is unplugging itself from Facebook.

No idea if legal threats were brought up in this case, but the parallel seems pretty clear: Facebook will offer outside sites access to its user base, but only on its own terms.

In both cases, Facebook wanted the would-be partner sites to use its recently launched Facebook Connect service. Last week, Power.com founder Steve Vacahni told me that he and Facebook had “resolved” their issues, and that Facebook’s lawyers had told him the suit would be dropped shortly. But as far as I know Facebook has yet to withdraw its complaint.

Which has probably served as an effective warning for Meebo CEO Seth Sternberg, who sent out this memo to his users tonight:

Hi Meebo,

Got some bad news.

As a bunch of you already know (because you’ve been using it), we recently added Facebook Chat into Meebo.

We have been speaking to the Facebook team, and it turns out, they’d like us to connect to their network in a different way. In the interim, they asked us take Facebook off Meebo, and we said ‘okay.’

However, we were glad to hear that the Facebook team was genuinely excited to see their network on Meebo, especially since they already have plans to open Facebook Chat. They also committed resources from their Chat and Facebook Connect teams to do extra work with us to get Facebook Chat back on Meebo ‘really, really soon.’

Work began this week, so stay tuned. We expect some all nighters on both sides!

Seth

P.S. Meebo grew in December. We reached close to 45 million people, a new record, including 2.5 million via Meebo Community IM. So it’s not all bad news… “

Update — here’s comment from Facebook:

We are excited to be working with Meebo to implement Facebook Chat using Facebook Connect. Their current integration was launched without meeting the policies we have in place to assure the trust users have established on Facebook is maintained when they interact with their Facebook friends around the Web.

We announced our plans to open Facebook Chat to third-party Websites in 2008 and are working closely with Meebo to create a great experience for Facebook users that use their service.

Turns out that many of them were doing the same thing–the Facebook part, that is. Web traffic-watcher Hitwise says Mark Zuckerberg’s site accounted for 1.93 percent of all U.S. Internet visits on New Year’s Eve. That’s up 75 percent from a year ago, when 1.11 percent of you checked in at the site at some point in the day.

But New Year’s wasn’t Facebook’s busiest day last month. That distinction belongs to Christmas Eve, when it set a site record of 2.18 percent of U.S. Internet visits, up from 1.42 percent in 2007.

You can draw your own conclusions about what those stats mean, or read Hitwise analyst Heather Hopkins’s theories here–she thinks snowstorms in the Northeast kept people trapped in their homes with nothing to do but post on their pals’ walls.

But I think the best explanation here is the simplest one: Contrary to predictions that Facebook would burn out as its core college audience grew tired of it, the site has continued to grow–it now claims 140 million active users worldwide. So you’re going to see records like this broken a few times a year.

The Recording Industry Association of America (RIAA) initially contacted Facebook last summer requesting the removal of the Project Playlist application for copyright violation, and recently reopened those communications. We have forwarded the RIAA’s letters to Project Playlist so it can work directly with that organization and music labels on a resolution. In the meantime, the application must be removed to comply with the Facebook Platform Terms of Service. Our hope and expectation is that the parties can resolve their disagreements in a manner that satisfies the developer and copyright holder, that continues to offer a great experience to music fans, and that doesn’t discourage other developers from using Platform to share their creativity and test new ideas.”

The only surprise here is that it took Facebook this long to face up to reality: There was next to no upside for Mark Zuckerberg and company in fighting the big music labels, three of whom are suing Project Playlist. But there was plenty of downside: At best, the social network would end up squaring off against potential partners; at worst, it’s conceivable that it could end up being sued by the labels as well.

Facebook’s move is also less important than the one that MySpace made last week. That’s because Project Playlist is first and foremost a music service geared toward users of News Corp.’s (NWS) social network.

It’s also not surprising that MySpace was the first to bail on Project Playlist at the labels’ request: Not only does the network have its own competing music service–MySpace Music–but its partners in that service are the four major labels– Sony (SNE), Warner Music Group (WMG), Universal Music Group and EMI.

Most important is what the big labels who are suing Project Playlist– Warner, UMG and EMI–hope to accomplish by forcing the social networks to cut it off at the knees. The boilerplate answer from the labels is that Project Playlist violates copyright, and that they’d complained to MySpace and Facebook before, etc, etc.

But that’s a silly argument: The labels have also been trying to negotiate a deal with Project Playlist for some time, which is why investor Bob Pittman sank up to $20 million into the company earlier this year and former Facebook executive Owen Van Natta came aboard as CEO last month. I’m told that those talks had reached advanced stages this month.

So that leaves us with two possible conclusions:

1. This is just another negotiating move by the labels, which have previously sued Web services before partnering with them (see: Warner/Imeem, Universal/MySpace). But since they’ve already sued Project Playlist, cutting off their oxygen is more effective.
2. The labels have decided that ad-supported, free music services like MySpace Music, Imeem and Project Playlist just aren’t going to work, period, and that’s there’s no point in even trying to let new ones thrive.

For now, I’m going with No. 1, just because it’s the most obvious answer. But I’m willing to hear other arguments: Sound off in comments below or drop me a line at peter@allthingsd.com.