That’s the path that Jason Herskowitz has chosen. Old job: VP of product management at Total Music, Universal Music and Sony’s (SNE) attempt to create a service that offered either free downloads or free streaming music as a way to combat file-sharing. It collapsed earlier this year and Project Playlist bought some of its parts.

New job: VP of product management at LimeWire, one of the last (one of the only?) high-profile peer-to-peer file-sharing companies based in the U.S. Not surprisingly, the service was embroiled with industry lawsuits for three years running.

Here’s Herskowitz’s blog post announcing his new job and his pending move to Brooklyn (Welcome, Jason! Pretty sure we’re neighbors.) from Washington D.C. It’s not a crazy career move: A job is a job and there aren’t that many in digital music these days. Besides, I hear that LimeWire has nice offices.

Which reminds me: How is it, exactly, that LimeWire stays afloat when the labels have been able to force so many of its peers to shut down? Good question. I’ve asked around and heard murmurings that the labels and the file-sharing service may be able to work out some kind of agreement, but I’ve heard that every 12 months or so. So I’ll believe it in when I see it.

In the meantime, LimeWire continues to allow you to download just about any song (and many other things) you can imagine over the Web for free, without paying anyone a cent. Though if you do try to download a copyrighted song, you do get this stern warning from the service. I take it in the same spirit as the warnings head shops give you when they say the bong they’re selling is for tobacco use only (click to enlarge):

But the lawsuits have yet to be resolved.

Confusing? Of course.

Here’s Project Playlist’s description of the deal, which references layoffs at the company to eliminate redundancies with the new acquisition, but doesn’t specify how many folks are being let go. Given that Total Music only employed about 30 folks at its peak and was essentially shut down last winter, it’s hard to see how many Total Music employees are coming aboard–I’m guessing fewer than a dozen, and am trying to confirm.

We recently acquired assets and employees from TotalMusic LLC, a digital catalog management and reporting system. This acquisition is an important platform that will allow us to host a streaming music service, help us with e-commerce solutions and provide a set of application programming interfaces that will be invaluable to us as we offer next generation digital music services to our users.

Today we are integrating the assets of TotalMusic into our Playlist operation. As a result we have to address some overlap in certain areas and let some employees go both from Playlist and Total Music. This is no reflection on the talent of the people we had to release, rather a responsibility we have to run a lean organization with no redundancies and clear lines of reporting.  This often happens when two companies merge, but it is never easy.

On a positive note, we are very excited about the progress we are making. With the Total Music acquisition and our recent licensing agreements with Sony ATV and EMI Publishing, we are developing new features and services everyday that will form an even deeper bond with our 45 million loyal users and create new revenue opportunities for our company as well as our music content partners. More to come, watch this Space!!

Total Music, which Universal started in the fall of 2007 and shut down this February after joining up with Sony along the way, was supposed to be a subscription music service that got bundled in with devices or with ISPs/cable guys/telcos, etc. Given that it never, to my understanding, streamed a single song or collected a penny in revenue, it’s interesting to see that Project Playlist thinks there’s something there worth buying.

The bigger picture: It’s hard to see how this company can move forward until new CEO John Sykes, who replaced Owen Van Natta when he decamped to run MySpace for News Corp. (NWS), can clear up lawsuits with Universal and Warner and then get Facebook and MySpace to let it back onto their respective sites. The social services were crucial to Playlist since they generated the majority of its visitors, but they cut them off last fall, presumably under pressure from the labels.

Given that Van Natta is now running MySpace and that Playlist was at least able to negotiate an asset purchase from Universal, perhaps there’s a shot at getting all of that accomplished. Then the service could concentrate on the even tougher task of trying to make money in digital music.

MySpace owner News Corp. (NWS) didn’t name a successor to DeWolfe, but sources said the company is close to bringing in Owen Van Natta, the former COO at Facebook and current CEO of Project Playlist, as a replacement.

(News Corp. also owns Dow Jones, which owns this Web site.)

In addition, News Corp. said that it is in talks to move aside Tom Anderson, DeWolfe’s longtime partner and MySpace co-founder, from his current position as president.

Here’s the memo:

Chris DeWolfe to Step Down as CEO of MySpace

Will serve as strategic advisor to Company
______________________

Los Angeles, CA, April 22, 2009 – MySpace CEO Chris DeWolfe and News Corporation’s Chief Digital Officer Jonathan Miller, announced today that, by mutual agreement, Mr. DeWolfe will not be renewing his contract and will be stepping down in the near future. Mr. DeWolfe will continue to serve on the board of MySpace China and will be a strategic advisor to the Company.

Additionally, Mr. Miller announced that he was in discussions with Tom Anderson, MySpace’s president, about Mr. Anderson assuming a new role in the organization.

“Chris and Tom are true pioneers and we greatly value the tremendous job they’ve done in growing MySpace into what it is today,” said Mr. Miller.  “Thanks largely to their vision, MySpace has become a vibrant creative community with 130 million passionate followers worldwide.  It is an enormously successful property and we look forward to building on its achievements with a new management structure we’ll announce in the near future.”

“In a little under six years we’ve grown MySpace from a small operation with seven people to a very profitable business with over 1,600 employees,” said Mr. DeWolfe.  “It’s been one of the best experiences of my life and we’re proud of, and grateful to, the team of talented people who helped us along the way.  We thank them, as well as the MySpace community for making our vision a reality.”

“From the very beginning, our driving passion has been simple – to create and foster a platform where people across the globe can not only meet and interact, but share music, videos, thoughts and ideas,” said Mr. Anderson.  I look forward to working with Jon.  I love this business, and look forward to its next chapter.”

People familiar with the matter tell me that DeWolfe and News Corp., specifically new digital boss Jon Miller, are discussing a leadership change today. News Corp. (NWS) officials declined to comment. (News Corp. is the owner of Dow Jones, which owns this Web site.)

Sources tell me Miller hadn’t been planning on getting rid of DeWolfe (pictured above) in the near future, and that until yesterday he was still evaluating his options. News Corp. CEO Rupert Murdoch had once treated DeWolfe as a favorite and gave him significant autonomy at MySpace. But Murdoch, who brought Miller on earlier this month, has been leaning toward a change as MySpace’s traffic has stagnated and its buzz and momentum have moved to Facebook.

Still, Murdoch had left the decision about the site’s leadership to Miller, his new hire, sources said. One possibility: Elevating DeWolfe to a nonexecutive advisory position.

Those options narrowed last night once TechCrunch ran a story claiming that News Corp. had hired a headhunting firm to “scour for possible replacements” for DeWolfe.

News Corp. hadn’t actually hired a headhunter, I’m told by multiple sources. But I’m also told that the report was enough to spook DeWolfe into calling Miller to ask what his plans were. That conversation led to today’s negotiations, which will likely lead to his stepping down as CEO, although he may remain affiliated with MySpace in some capacity.

Meanwhile, News Corp. has been talking to Van Natta (pictured here) about taking DeWolfe’s place. Van Natta, who had been a highly regarded executive at Facebook, was at one point the leading candidate to head up MySpace Music, which launched last fall, and the two sides held extensive conversations.

But Van Natta, like many other potential hires for that position, bristled at the job’s org chart: Rather than a standalone company, a la Hulu, the site News Corp. set up with GE’s (GE) NBC, MySpace Music is simply a unit of MySpace, reporting to DeWolfe. MTV executive Courtney Holt eventually took the job.

But Van Natta’s fate has remained closely intertwined with MySpace anyway. Project Playlist, the free music-streaming site he took over last fall, has seen traffic plummet after MySpace, along with Facebook, cut off the site’s access to their users, a move prompted by lawsuits from several major music companies.

Van Natta has made some headway at extracting the company from its legal mess, which predated his hiring, and he has hammered out a settlement with EMI Music Group. But Playlist is still being sued by Warner Music Group (WMG) and Vivendi’s Universal Music Group, and even music sites that aren’t in legal trouble are struggling to keep their heads above water. Plenty of Silicon Valley watchers wonder why Van Natta landed at Playlist in the first place and think that he has been looking for a way out.

Here’s a video of DeWolfe talking with BoomTown’s Kara Swisher a little more than a year ago when MySpace opened a new office in San Francisco. Below that is a video of Van Natta talking to Swisher in 2007 about Facebook’s ill-fated “Beacon” project.

No terms were disclosed. The settlement, in conjunction with an earlier deal struck with Sony’s Sony Music Entertainment (SNE), means that Project Playlist now has deals with two of the big four music labels. But Warner Music Group (WMG) and Vivendi’s Universal Music Group are still suing the company.

Just as important: Project Playlist hasn’t been reinstated by MySpace and Facebook, both of which booted the service off their social networks last November. Since Project Playlist depended on those sites to drive traffic to its site, it’s hard to see how it can gain much traction unless it can sweet-talk the two other labels into coming aboard.

My expectation was that a settlement was in the works last fall because that’s when former Facebook COO Owen Van Natta joined the company as CEO and investor Bob Pittman poured several millions of dollars into it. Neither of those men, I assumed, was betting on a prolonged lawsuit.

Project Playlist isn’t the only music start-up struggling these days–even those that haven’t been sued by the labels, or have deals with them or even investments from them, are trying to figure out how to survive. Most assumed they’d be able to make money via advertising, but that was a hard sell even before the recession/depression.

Still, better to have a deal than a lawsuit.

Preprepared quotes from both sides:

Van Natta: “It is crucial for us to continue connecting our users with more of their favorite music. This partnership will provide us with a wide-ranging selection of content to satisfy our users’ appetites to share and purchase music. We are excited to now have both EMI and SONY BMG Music catalogs available and we hope to continue to expand and enhance our service.”

Ronn Werre, EMI Music’s President, Music Services worldwide: “Making our music available on a fan favorite like Project Playlist is part of EMI Music’s mission to connect artists and fans and to give fans more ways to discover new artists. Project Playlist is becoming a fan favorite. Our artists also know that word-of-mouth among friends is a powerful part of music discovery.”

Pittman’s Pilot Group Ventures has already taken flyers on two of these things–DailyCandy, a shopping/events guide for cosmopolitan ladies, and Thrillist, a DailyCandy for the ladmag set. Now he’s done it again: He’s invested money in VitalJuice, a DailyCandy for fitness fans. Terms weren’t disclosed, but I’m told that Pilot invested $1 million in the company.

The New York-based company started up in the spring of 2007 and now has 50,000 subscribers; that number should increase as the company launches versions of the newsletter targeting Los Angeles and New York. Co-founder Amanda Freeman told me that she and partner Lisa Blau liked the DailyCandy model and thought it would work well for fitness and wellness tips.

“We felt that email was the perfect kind of delivery for this kind of content,” she says. “If you had a disease, you’d look up something on the Web. But healthy living isn’t something you seek out.”

I don’t know how much convincing Pittman required, but if anyone is a believer in the model, he is: He invested something like $3 million in DailyCandy in 2003 and sold it last summer to Comcast (CMCSA) for $125 million. It’s the biggest win to date for Pittman, who is well into a third career as a private media investor following earlier stints at Viacom’s (VIA) MTV and as one the major players during the ill-fated AOL-Time Warner (TWX) saga.

Some of Pilot’s other high-profile deals include stakes in Huffington Post and Project Playlist.

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.

It’s conceivable that iLike, led by brothers Hadi and Ali Partovi, is simultaneously pursuing funding options. But my understanding is that much like competitive music service iMeem, which is also on the block, iLike’s executives and investors are worried about keeping the company afloat as a standalone entity. Delivering free music on the Web has so far proven to be a high-cost, low-revenue endeavor, and that’s a difficult path to choose in this environment.

My sources couldn’t tell me what sale price iLike is hoping to get. It has raised about $16 million in two years. Most of that came from Ticketmaster (TKTM), which has now split off from Barry Diller’s IAC and trades as standalone company. A smaller slug came from Bob Pittman’s Pilot Group, which has taken a stab at other Web music start-ups, including a recent investment in Project Playlist. I’ve asked the Partovis and their PR rep for comment, but haven’t heard back.

Ticketmaster’s existing ownership makes it an obvious buyer. The company also has a relationship with RealNetworks (RNWK), which began powering a free music service for iLike this summer. And while I don’t have confirmation that the two companies have actually talked, the third very obvious buyer would be Facebook, which is responsible for the company’s success to date.

iLike originally started out as a music discovery service that promoted the homegrown music found on Garageband.com, another Partovi brother music start-up. But it really hit its stride with the launch of Facebook’s open developer platform in the spring of 2007. Since then it’s become one Facebook’s most popular apps, with more than 5.4 million active monthly users.

That hasn’t translated into huge revenue: The company hasn’t expended much effort trying to sell advertising on Facebook, which is a challenging environment to begin with. And while it generates referral fees when it sends concertgoers to Ticketmaster, those sales haven’t been significant enough to register on the company’s SEC filings so far.

Now Facebook is looking to create its own music service, and it’s conceivable that iLike could step in and take on that role for the company. One big problem: Facebook wants to provide users with a service that gives them the ability to listen to songs in their entirety, à la MySpace Music. But Facebook doesn’t actually have licenses with the big labels that allow it do that. Instead, it provides users with 30-second clips.

All Things Digital’s Kara Swisher visited with Hadi Partovi this summer; below the two talk about iLike’s history and ambitions.

Or maybe they’re just like us: When their 401k’s gets crushed in a once-in-a-lifetime market rout, they think twice before writing another check.

That appears to have happened in October, when VCs spent less money, on fewer companies, than they have in years. Details from Thomson Reuters/PE Week, via PE HUB:

The data show that U.S.-based venture firms invested in just 250 companies in October, down from 565 companies in September and 518 companies in October 2007. You have to go all the way back to January 2004 (when they invested in 232 companies) to find a lower number. The only other October with fewer deals was in 1993.

The amount of capital that VCs are investing also plummeted in October, when U.S.-based firms put $2.5 billion to work, down from $3.8 billion in September and $3.2 billion in October 2007. The October 2008 total is the smallest amount that U.S. VCs have invested since February 2006, when they invested about $2.4 billion. Looking only at October, the last time the monthly total was lower was in October 2004, when about $2.4 billion was invested.”

Recall that in addition to the market getting crushed last month, October also ushered in a flurry of look out! pronouncements from some of the VC world’s biggest names, including Sequoia Capital. So it’s understandable that deal flow might dry up.

But it’s not going away entirely. And it doesn’t mean that VCs are avoiding Web 2.0-like gambles. See, for instance, the $20 million or so that investors just pumped into Project Playlist, yet another music discovery services with both legal challenges (the music labels are suing it) and operational ones (there isn’t much revenue, and getting more will be tough).

Nor does it mean that the investors who fund VCs themselves are bailing out–yet. More on that later.