Who

A failed entrepreneur, former New York columnist, and the author of several books, these days Wolff pens a media column for Vanity Fair.

Backstory

Wolff never built the media empire he'd always hoped to, but he's managed to turn his ill-fated business career into a pretty successful one as a media pundit and columnist. A New Jersey native and Vassar grad, Wolff started his working life as a copy boy at the Times before moving on to write for Esquire and the New Times, publishing his first book, White Kids, in 1979.

Then came a slew of ill-fated media projects: He tried to take over the National Lampoon (it didn't happen); attempted to launch a travel magazine (his investors backed out, he turned the experience into a book); and then landed a lucrative contract to write a novel (he never finished it). An early web adopter, in 1994 he founded an online publishing company, Wolff New Media, and spent the middle part of the 1990s trying to get it off the ground. Like his previous projects, though, the venture never panned out and it was shuttered in 1997 amid controversy. But Wolff managed to once again turn the experience into a book, 1999's Burn Rate, a gossipy account of his company's demise.

In 1999, Wolff was tapped by former New York editor Caroline Miller to serve as a media columnist for the mag. Another bid for mogul status followed when he attempted take over New York after it was put up for sale by Primedia in 2003. Despite Wolff rounding up some of the biggest names in town (Mort Zuckerman, Harvey Weinstein, Nelson Peltz, Donny Deutsch, Jeffrey Epstein), Bruce Wasserstein snatched the mag away from the consortium at the last minute. Wolf landed at Graydon Carter's Vanity Fair shortly thereafter.

Of note

It's a touch ironic that a man who never managed to achieve any success in the business world spends his days critiquing and second-guessing people who, for the most part, have succeeded. But while Wolff may be a doomed businessman, his observations about the media business are often spot on—assuming, that is, that you can get through his exceedingly self-indulgent writing. Unfortunately, the lesson Wolf should have learned during the past three decades—that he's better off typing at a keyboard than running a business—has yet to sink in. In 2007, he launched Newser.com, an online content aggregator. Ironically, Wolff ripped his own business model to shreds in the pages of New York several years ago: "I have seen this business plan many times—numerous entrepreneurs believe that the market demands a way to regulate the anarchy of content. We need a global editor (editor-in-chief of the world) to tell us what information we can trust." Who knows, perhaps the 6th time will be the charm.

In print

Wolff has published a number of books since Burn Rate. He earned a reported $750,000 advance for his Autumn of the Moguls in 2003, which Publishers Weekly described as a "tremendous display of ego slathered over superficial analysis." His next book, for which he earned an equally lavish sum from Doubleday, will be a biography of Rupert Murdoch.

Grudges

Given his tendency to tear up media personalities, it's no surprise that Wolff has collected a few enemies over the years. He attended college with Judith Regan and they were once very close friends; Regan even hired Wolff's wife as her divorce attorney. After he wrote a column critical of her, though, the relationship dissolved and the name-calling began. (Among other things, Regan said Wolff was obsessed with "money and position and success," and resented her for achieving so much more than him.) Wolff also feuded with Steve Brill several years ago. When the CourtTV founder questioned some of the claims in Burn Rate, Wolff fired back with a stinging column and a war of words ensued. One other person Wolff has long despised: venture capitalist Alan Patricof, who invested in Wolff New Media and then helped shut it down.

Personal

Wolff is married to Alison Anthoine, a fellow Vassar grad and a lawyer. They have three children and live on East 74th Street.