Anderson Cooper, Harold Ford Jr. and Bob Guccione Jr.

After a long holiday weekend left the usual Wednesday lunch crowd without their weekly power lunch fix, the town car set who could tear themselves away from their Hampton cottages returned to Michael’s today. I say we outlaw any more midweek July 4th holidays. Too confusing!

I was joined today by Bob Guccione Jr. who I met last year when we weighed in on the ever expanding culture of celebrity for a journalism panel for Names Not Numbers. After crossing paths in this dining room several times over the past year, we decided it was time for a proper Michael’s lunch once and for all.

I wasn’t disappointed. Bob ventured in for our lunch and some other important business in town from his home in rural Pennsylvania (“I’m one postage stamp away from being the Unabomber!’). A few years ago, having grown “sick of New York” he decamped to Mississippi to teach journalism and has decided country life beats living in Manhattan hands down. “It’s so peaceful,” he says.

Bob tells a terrific tale of his fascinating career in media that started at the age of 18 in the UK when he became Britain’s youngest ever publisher. A year later, he launched Rock Superstars, making him the youngest publisher in America. As the son of one of publishing’s most colorful figures, it seems his career path was predetermined but, says Bob, “I knew I loved it. I wanted to be a writer but I had no life experience.”

That changed pretty quickly. In 1985, he launched SPIN, sold it in 1997 t0 Vibe Ventures, and launched Gear in 1998. Then, in 2005 he bought Discover from Disney. He remembers the moment well. “The staff regarded  me with some trepidation. When I told them  ‘We’re in the entertainment business,’ there was an audible gasp in the room.” By the time he stepped down as chairman two years later, the magazine had returned to profitability.

Diane Clehane and Bob Guccione

Our conversation revolved around passion for the business and the elusive quest for profitability and Bob had plenty to say on both fronts. Besides being incredibly funny (sorry, but his best remarks are off the record), the tireless entrepreneur proved to be a fascinating lunch date as he shared his extremely well-reasoned take on why he believes writers will one day be able to make a living online and why magazines are far from over. “Everything about digital media happened too fast, and people back the wrong model too quickly,” he told me. Exhibit A: The Huffington Post, which Bob says is “doomed to fail” and called it “a white elephant — it’s the default model.”

The future sucesses online, says Bob, is in recognizing that quality begets quality. In order to be profitable online, publishers “have to produce superior content, and smart people realize you have to pay for that.” Of the plethora of blogs that give writers “exposure” instead of a fair wage he says, “Just because you can get someone to do something for free doesn’t mean someone else is going to patronize that site. Cheaper is never better.” Too much of the content written for free  is “self-referential and self-promotional — even good writers can fall into that trap. It’s like processed food. It’s filling, but it’s not good for you.”

So, says Bob, well-written, interesting content – and the writers who get paid to write it – will be the deciding factor of winners and losers online. Those writers might want to send Bob their resumes. He tells me he’s working on two startups, a luxury travel site and, a wine site with a “heavy commerce component” that “won’t be snobbish about wine.” Both are scheduled to launch within the next six months. He is also hard at work on a new food magazine for print which will, of course, have an online component. (The site’s content will be exclusive and different from the print edition). Here’s a tasty tidbit about the project: Bob tells me he’s working on the project with a “brilliant famous chef” as his co-editor. “It’s someone who really understands media.” It’s too soon to say more, says Bob, so let the guessing game begin! “When people say ‘magazines are over’ I say, ‘Not the good ones!'” he reasons. “Gourmet folded because it wasn’t a good magazine. Too much of the stuff was self-referential and it wasn’t entertaining.” He points to New York magazine as an example of a magazine that’s “doing its job.” Says Bob: “Not everyone reads it, but those who do enjoy it.”