Jay Penske Builds West Coast Blog Empire One Link at a Time

Does Jay Penske want to be the next Nick Denton? Or maybe the next Si Newhouse, as Denton's own Gawker described the 30-year-old would-be mogul in June. Penske's certainly throwing a lot of money around the Web, acquiring, developing, and re-branding sites like someone who wants to make a big splash in the already crowded shallow end of the Web content pool.

Penske is the son of billionaire Roger Penske (he of the eponymous auto-racing team and soon-to-be owner of GM's Saturn brand) and the owner of Mail.com an AOL-like portal that offers free email accounts and Web-based data storage. According to Paid Content, Mail.com's parent company, Mail.com Media Company, secured $35 million in funding from Quadrangle Capital Partners, WI Harper Group, and Novel TMT Ventures in 2008.

So, what did Penske do with that money? Go on a spending spree, of course! In June MMC acquired Deadline Hollywood Daily, Nikki Finke's always addictive, often authoritative, sometimes abrasive site for industry news and gossip. The Los Angeles Times' Company Town reported at the time that Finke received "a low seven-figure sum." In an A1 story in today's New York Times, David Carr spoke to Finke (via telephone—Finke rarely makes appearances or takes meetings in person) and described the deal as follows: "Ms. Finke stands to make more than $5 million in the next eight years, and her deal could go as high as $10 million, according to one of the people involved in the deal who declined to be quoted citing the private nature of the negotiations."

Finke also addressed her reputation as something of a barracuda, telling Carr, “I don’t bully and terrify people… I’m not mean, I just write mean.” (As someone who's been on the receiving end of Finke's calls and emails, I can tell you she actually does terrify at least one person: this reporter.)

Also in The Times, Carr talks to former Us Weekly editor Bonnie Fuller who's setting up shop online with—Guess who!?—Jay Penske's Mail.com. Fuller, like Finke, is a figure both admired and sometimes criticized in media circles for her ambition, her canny understanding of her niche (celebrities' divorces and visible cellulite), and her unsinkable career. Carr reports that Fuller will be heading up Penske's revamped Hollywood Life out of New York, which is the celebrity-obsessed sister site of Movieline.com, which Penske re-launched recently with the help of several former editors of Gawker Media's Defamer.com.

So, what's Penske's long-term goal—besides the usual "world domination" dreams young media barons seem to indulge so freely? Watch this space as we try to keep up with him.