Following former Facebook No. 2 Owen Van Natta's decision to take the top job at music startup Project Playlist, New York Times technology columnist Saul Hansell asks, "What does Owen Van Natta know about how to make money from music on the Internet that hundreds of others before him couldn't figure out?" Project Playlist, after all, is yet another fast growing music site that record companies are accusing of promoting piracy. "From the original Napster to Rhapsody and iMeem today, music has been the Bermuda Triangle of the Internet, swallowing anyone foolhardy enough to try to navigate its treacherous …

Are YouTube and Hulu destined to become movie destinations? It's an avenue the companies are certainly exploring, but the real question, Cnet's Greg Sandoval says, is how to exploit it. For one thing, there are concerns about ad-supported business models, and whether studios can match or exceed the kind of returns they've seen from pay-TV, DVD sales, and digital services like iTunes. Among the challenges: consumers balking at the idea of watching two-hour long films on their PC, or clicking away if asked to sit through the same number of commercials that are shown on traditional TV. Also, in the …

Facebook may have passed MySpace in terms of worldwide audience, but the social networking giant has struggled to sell ads as effectively as its competitor. Today, the Palo Alto company is unveiling its latest ad format, called "engagement ads" which prompt a user to do something within the ad unit, such as post a comment about a product or RSVP to watch a TV show. Once a user engages with an ad, a message would then be sent through the news feed to his or her friends list. As the Journal points out, Facebook has a lot to prove …

New York Times technology writer Saul Hansell says Google's recent move to put feature-length films and TV shows on YouTube is -- like most of the online video giant's forays into professional content -- more show than substance. Hansell claims that Google is merely intimating that the professional video market could become a core moneymaking strategy for YouTube, without really making the commitment to it. Meanwhile, Hulu.com, the joint venture from NBC and Fox, is starting to establish itself as the most prominent site for professional TV shows and movies. As Jim Packer, MGM's co-president, tells the Times, "We …

Online retailers are bracing themselves for a tough holiday season, a Shop.org holiday survey finds. Thirty percent of the marketers surveyed said they were trimming their marketing budgets in response to lower than expected sales, while 16% said they were reducing promotional spending. "(Retailers) are looking to save costs wherever they can," Scott Silverman, executive director of Shop.org told Ad Age. "And they're investing in some of the tactics that they know are going to pay off." Free shipping, for example. A whopping 45% of retailers said their budgets for free-shipping promotions were either significantly or somewhat higher compared …

Who says the venture capital market is dead? HomeAway, an online vacation rental marketplace, just raised the biggest round of VC funding of any technology company since 2000, in a $250 million round brings the four-year-old startup's total venture funding to $405 million, The New York Times reports. HomeAway operates under the simple concept of connecting second homeowners in the United States and Western Europe with prospects who want to rent their homes. In its four years of operation, HomeAway has leapt to the top of the vacation rental pile thanks to an aggressive acquisition strategy. The site has …

Former Facebook COO Owen Van Natta has resurfaced as the CEO of music discovery site Playlist, Kara Swisher at All Things Digital reports. It had been widely suggested that Van Natta might take the vacant position as head of MySpace Music, but Van Natta ultimately opted for the smaller music discovery site. The former Facebook executive's arrival was coupled with the announcement that former AOL exec Bob Pittman will be joining the company's board, with his company, Pilot Investment Group, investing an undisclosed amount of money in the music startup. Swisher says the new funding is in the $18-$20 …