Rumors of problems at Portfolio began long before the Conde Nast business magazine folded Monday. Media watchers have been obsessively analyzing Portfolio's every move since the title launched in April 2007 and much of the criticism has focused on editor-in-chief Joanne Lipman. Observers say Lipman, who came to Portfolio by way of the Wall Street Journal had a troubled relationship with her staff, spent too much money, and didn't get the Internet. According to others inside the embattled business book, Portfolio's demise may have also stemmed from poor planning and organization, a missed opportunity with its critically-lauded Web site, and falling newspaper revenues at Conde Nast parent company Advance Publications.

Finance blogger Felix Salmon was one of the many marquee hires Portfolio made upon launching two years ago. While Salmon left the magazine earlier this month to blog for Reuters, he says he "was deliriously happy at Portfolio" and hadn't been looking to jump ship. "There are lots of people who had a lot of issues with [Lipman], but I think it's clearly a little bit much to blame the demise of the magazine on her because it wasn't her idea." At last night's panel on "The NEW, New journalism" at NYU Portfolio's Washington editor Matt Cooper told the audience that he liked the concept behind Portfolio but that it "was a great idea at a bad time." We've also heard from three other former Portfolio insiders who cited the initial concept and timing among the magazine's flaws.

Lipman's critics contend that her overspending, editorial choices, and management style were central to the demise of the magazine. FishbowlNY alum Elizabeth Spiers wrote that Conde hired the "wrong editor" for Portfolio, recalling her own 2005 interview with Lipman that she left thinking "I could never, ever work for this person." For his part, Salmon didn't find Spiers' take to hold much water, deeming her "just not one of life's natural employees." However, Spiers is far from only media watcher connecting Portfolio's closure to the beleaguered EIC: At Monday's Matrix Awards, a media vet of multiple decades opined that "a different editor might have resulted in a different outcome" at Portfolio. (Lipman did not respond to request for comment on this story.)

Much of the coverage of the rise and fall of Portfolio made mention of the magazine's extravagant $100 million budget. Daily Beast editor Tina Brown, who has her own history of pricey media launches, lamented Conde Nast publisher Si Newhouse's unwillingness to continue spending money on Portfolio, and deemed the title's closure the "the magazine world's last big believer, Si Newhouse, exhibiting what looks like signs of throwing in the towel." Salmon theorizes that Newhouse would have been willing to continue losing money on Portfolio, were it not for problems at the newspaper division of Conde Nast parent company Advance Publications. Newhouse "always had the ability to bleed however many millions of dollars it would take to keep Portfolio going," Salmon said, adding that historically, "Conde was the glamorous, headline-grabbing magazine arm" of Advance and that "newspapers are really where the money came in." With Advance's newspaper business in trouble Salmon suspects that "suddenly Si has to be much more serious about making money than he ever was in the past." As a result, according to Salmon, "it wasn't really Portfolio that was the problem, it was the Advance newspapers that were the problem."

Aside from overspending, problems with Portfolio's Web site were another major miss by the magazine: Newsweek's Daniel Gross echoed the conventional wisdom when he criticized Portfolio for having a "somewhat retro" attitude about the Web, in which the site was an afterthought and "the magazine was clearly the show." However, Salmon rejects the notion that the Web site wasn't integral to Portfolio's strategy, pointing out that Portfolio.com was "run in a sort of maximalist true Conde manner" with a "massive budget" and a "massive infrastructure" of "25 editorial staff, another 15 business and development staff" and "their own dedicated tech team" that was separate from CondeNet, the Web publishing division of Conde Nast.

Despite all the resources, the site was hamstrung by its size and setup. "It was always really hard to change things," Salmon said of the site and its development, owing to organizational issues between CondeNet and the Portfolio team. Costs at the site also proved to be an issue, and most of the magazine's digital staff was fired in a round of budget cuts last fall. In the end, Salmon thinks Conde Nast "learned a lot from Portfolio" though he acknowledges "it's not yet clear that they know how to run a successful Web site."