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Want Bob Pittman’s Money? Start a Newsletter Business.

Are you an aspiring media entrepreneur trying to figure out how to  raise money during brutal times? Here’s one method: Start an email newsletter business, then give Bob Pittman a call.

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.

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Peter Kafka has been covering media and technology since 1997, when he joined the staff of Forbes magazine. Most recently, he has been the managing editor of the tech and media Web site, Silicon Alley Insider. Read more »

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