In Part One of this essay, I laid out my own personal ride with Condé Nast Portfolio, Si Newhouse’s ill-fated venture into business media. Like baseball managers, magazine writers are hired to be fired, so aside from the shock of that layoff being my very first, I harbor no special animosity towards the magazine or anyone who worked there. But since the magazine was about business, it’s not unreasonable to dissect, from that perspective, the failings therein. As I see it, there were three major ones (Dan Gross sees four):

  • An emphasis on print over web.

Lipman came to Condé Nast from the Wall Street Journal to run a print magazine. Although the website was much touted, it was a secondary thought to her and her top editorial staff. When a directive went out from the then Managing Editor that all hands were expected to contribute to the website, that directive was remanded by Lipman for her top tier contract writers. She wanted to save their talents for the magazine, she explained. But in 2007, the future of any publication has to include a plan for the web. And that plan had to be the web. Portfolio was touted within Condé Nast as being a non-CondéNet operation. CondéNet is the Politburo for all the magazine websites in the Condé Nast stable. With its own editors, production staff and advertising personnel, its centralized approach has led most magazines within 4 Times Square to devote little if any of their resources to the websites. And why would they? They receive no benefit, no cut of advertising, and no praise for doing so.

Lately, the tide has slowly turned, as more sharing of content and personnel is happening, and magazines are held accountable for their sites, whether under CondéNet or not. But thanks to the fragmented structure of the company, determined largely by the creation of fiefdoms for each of the younger generation of Newhouses working there, the institutional default is still to keep the magazine and web separate. So while Portfolio’s website structure was a major advance within the company, it was still archaic compared how tightly integrated the website of say New York magazine is to the printed product.

When robust websites play such a huge role as they do in media today, Portfolio’s was a fundamental flaw in the structure of the magazine. An editor and publisher more focused on a tight integration of the two parts might have found they were greater than their sum. But when the time came to make cuts last year it was the website that was sacrificed. At the time, I heard that publisher William Li told the laid off staff that even though the website was doing better than the magazine, it would never meet the company’s financial goals for the combined product. And as long as Condé Nast considers itself primarily a print operation, it will run into that problem with all of its websites.

  • Spare no expense.

The gilded age of media is over. Though one former Journal reporter recently recounted in The New York Times how he was admonished in the early 80’s for flying business rather than first class to South America, print media as a cash machine is yesterday’s news. Yet spending at Portfolio was epic. I heard more than once from staffers about $100,000 photo shoots that were shelved or thrown out when the corresponding articles fell out of favor. In some ways, this is the Condé Nast way– this is the company that brought Annie Leibovitz into the mainstream, and spared no expense to set up her iconic Vanity Fair shoots. While Vanity Fair traffics in Hollywood and glamour, Portfolio attempted to bring the same gloss to business. When I started working at Portfolio, I told sources on the phone that we were like Vanity Fair or The New Yorker, but for business journalism. (It was a common refrain since few people recognized our name at the time.) This may have been a convenient phrase for staffers, but as a model for a photography budget, it was a bit much. Portfolio ran some stunning pictures– but there are many more you’ll never see, because they died an expensive death. Ultimately the readership was not interested in vanity shots of Summer Redstone and Barry Diller.

  • Fragmentation.

As I wrote in Part 1, Portfolio was given every chance and resource to be a big, important new magazine. But the truth is, the era of that kind of publication may have passed. Based on the wild undulations in content from issue to issue, and the varying directives I got for the somewhat regular Demystifier column that I helped conceive and write, it felt as if we tried to please too many people in too many different ways, ultimately pleasing no one. A public that has grown used to finding exactly the type of niche content it wants from blogs and websites online, especially in the business realm, was probably not going to give Portfolio the time it needed to show it could make long form business profile journalism relevant again.

This is where the website comes in. An editorial staff of nearly a hundred is looking for more space than a magazine can normally provide. A website can provide that space, and if content is coordinated properly, it can play off the magazine, rather than merely mimic it. But in my experiences in planning features at the magazine (admittedly limited), a comprehensive strategy for print articles to hit the web with additional content, additional photos, etc, didn’t exist. Instead the web team was left to pick up the pieces of the print staff, and scrounge together a plan for repurposing and adding content, with little or no help from the original writer or editor. Wired with its massive blog network, is a Condé Nast title that has invested heavily in capturing fragmented audiences online, and steering them to the magazine. Of course, Wired has also faced a precipitous drop in print advertising, and its online operation has also faced staff cuts.

Condé Nast is not going out of business anytime soon, and at the very least, its flagship titles will probably exist in perpetuity. But its future moves will say a lot about whether it learned its lesson with Portfolio. Surely the economy will recover, and the Newhouses will attempt to grow their business once again. But in that future, when the opportunities are ripe, the path may be just as obscured as it is now.

Two thoughts of advice to the Newhouse family and other media billionaires under whose beneficence we work:

One, if you’re going to chase a fragmented audience like the business one, be prepared to sink huge resources into channeling a thousand streams of different types of readers to the mothership by creating niche content that appeals to them. The blog network of Portfolio.com was the closest thing to this approach they had, but since it probably wasn’t seen in this light, it was sacrificed to save the already crumbling parent.

Two, don’t build a rocket ship to the moon. There are thousands of journalists looking for jobs (and this is not a personal plea for reemployment) and thousands more in journalism school who are trained in new media. Want a big new idea from your executives? Start a Condé Nast incubator and make them read the proposals for funding that come in. That’s how the world’s most successful new media enterprises, from Twitter to Yelp to Facebook, are being built. (And if you don’t think those are media, you are beyond help.) I promise you, the next Vanity Fair is not coming from the executive suite. But it may come from a writer or editor who’s currently out on the street. (Last thing: if they tell you it’s going to cost a $150 million dollars to launch, run.)