We know D.C. Get our free newsletter to stay in the know.

The standard Internet booster script casts the Web as the new frontier, and its new-economy leaders as modern-day Lewis & Clarks. The fanfare, of course, ignores a key fact about the age of discovery: Plenty of people got lost along the way.

These days, that downside of the high-tech wilderness is manifesting itself with a vengeance at the offices of WashingtonPost.Newsweek Interactive (WPNI), the local paper of record’s effort to turn itself into an online powerhouse. By one inside account, WPNI lost both the night editor and the midday PM Extra editor recently. And within the last year, the deputy managing editor, the metro editor, the business editor, the national editor, and a ton of technical people have exited the Washington Post’s frontier wagon train to take advantage of manifest opportunities for the digitally savvy.

Next week, the chief navigator for all the uncharted territory will follow them over the dot-com horizon. As CEO, Marc Teren was charged with making the Post brand ubiquitous in digital realms.

Though businesses with a dot in the middle usually don’t assess performance on the basis of trifles like whether a guy helped his firm make money, Teren did accomplish a couple of things beyond simply spending Don Graham’s inheritance. He leveraged the paper’s chief asset—the credibility and value of the Post news franchise—into a lot of traffic. Washingtonpost.com is among the top six news sites in the country. Teren also managed to form what may—fickle Internet Gods willing—be important strategic alliances with MSNBC and NBC News.

Perhaps most important, he didn’t embarrass the news organization, as many feared he would when Teren arrived from Disney. Using the Web, he leaned on and added a little electronic pixie dust to the Post name without sullying it.

But the Post Co. had hoped to grow a local tribe of dedicated users that could be sold to advertisers throughout the region. When it came up with channels that offered entertainment and service listings, along with a micro-local portal called onwashington.com, the Post figured that the ad money would be just a few clicks away. Let’s just say that it didn’t happen in the last millennium, and it may not happen in the next.

Teren will be leaving to become CEO of Cahners Business Information, owned by global info-giant Reed Elsevier. Cahners owns 140 business publications that occupy niches from furniture to retailing. Business-to-business communication on the Web offers a much riper opportunity: You don’t have to spend time gathering a tribe of customers—you already own them. You just need to figure out how to compel them to spend time and money on your site, looking for new talent, deals on equipment, or minute-by-minute trend updates.

“I loved working for the Post, but I think I’m going to a phenomenal opportunity,” Teren said in a phone interview. Christopher Schroeder, who arrived at WPNI last October from the Post Co.’s Legi-Slate subsidiary, will be taking over for him. He was asked what magic he possesses that Teren didn’t. “That’s not really the question,” Schroeder says. “Marc and I are very congruent in the vision for this site. The question of making our site a key community resource is one of execution, and I think the people here have a religious commitment to making that happen.” (Executive Editor Christopher Ma will move to the corporate side of the company as a vice president, where he will reportedly hunt for still more electronic alliances.)

Teren admits that the company has some miles to go before finding gold in the territory it already owns. “I think the most difficult part of the job is cracking the code on local solutions—bringing along small and medium-sized businesses that need to embrace the Web,” he says.

The company’s biggest asset—its strong brand in news—becomes the site’s biggest weakness when it comes to repositioning for a broader slice of the market. Visitors to washingtonpost.com stop in, see the news of the day, and then keep moving.

In cyberspace, a big robust media company like the Post is actually a piker. That’s because the people it’s competing with are financed by IPOs, stupid money that doesn’t have to show a return anytime soon. It’s a mismatch—one that the Post’s brethren at the New York Times’ digital component have decided to remedy by cooking up their own IPO, according to the current issue of Wired magazine.

Any IPO at WPNI would obviously raise significant practical and cultural issues at the company. Right now, the work product of a union shop—the Washington Post on paper—is transmitted to a nonunion shop in right-to-work Northern Virginia. How might some of those notebook-toting schlubs feel if their industrious output were used to build an IPO at a newly atomized WPNI?

Teren says taking a portion of the company public is among the universe of possibilities the Washington Post Co. will have to consider in an age when options are handed out to dot-com employees like so many Christmas turkeys.

But potentially enriching options aren’t the only reason that people are fleeing the Arlington office of WPNI. Says one who left for a large tech company, “I didn’t come here for the money. The boom is over here, anyway. I came here because there are a lot more career options here, and I really don’t think [WPNI] ever figured out what they wanted to be.”

“It’s a tough position to be in,” the former staffer continues. “They want to be a portal for local entertainment and shopping, but that’s not how people think of the Post.”

Erin O’Shea Starzynski, communications director for WPNI, doesn’t see the departures as out of line for a digital enterprise. “It’s pretty typical for us, and for the rest of this industry, to have high turnover,” she says. “It’s more difficult to compete when you can’t offer a piece of the pie, like a lot of other folks that work in this industry…but I don’t think that in today’s economy, people expect to be going here, or anywhere, for life,” she says.

Highly Regardied Monday’s MLK holiday left most phones unanswered, but Bill Regardie picked up his on the first ring.

So, Bill, your only two editorial people quit, your ads might finance a brochure, and the distribution of your mag is almost as screwed up as Talk’s. What do you have to say for yourself?

“You got time for lunch?”

Lunch with Bill Regardie is one of the privileges of Washington life. He’s the rare smart guy in Washington who knows his own limits but remains supremely confident in spite of them. And he usually pays. We met at La Fourchette.

There is an odd disconnect in the current version of his magazine, dubbed Regardie’s Power. While all the news about the news seems bad, the news inside it is borderline spectacular.

The January/February issue is jam-packed with stories—there aren’t many ads to keep them apart—that hew to the old Regardie’s formula of businessman as hero, jerk, and tragic figure. The magazine pulls back the blankets on Federal City Council efforts to use Hill contacts to steal the old convention center site, tells the story behind the story of two cons disguised as businesspeople, and explains how satellite TV mogul Charles Ergen spent just enough time lobbying Congress to get screwed by a bunch of politicians who don’t earn the change in his pocket in a year. Never mind the unnecessary profile on tech-guru Mario Morino—I’m sorry to be among the hundreds of local journalists who have committed his name to paper—there’s a lot of other good stuff to behold, including a nuanced look at the Kabuki-like rituals between venture capitalists and start-up entrepreneurs penned by Regardie’s Power Editor Eric Felten.

Make that writer Eric Felten. Felten will help Regardie publish the next issue of the magazine and then move on to the Washington bureau of Reader’s Digest. Phillip Chalk, managing editor, will be leaving journalism to work with an organization that provides micro-loans to impoverished people, according to Felten. So Regardie has a well-edited magazine to show around, but no editors.

What, me worry? Regardie leans into a glass of red wine. “I’m not worried about finding a good editor in Washington. I need an experienced local reporter who covers business and politics. I would like him to be an exquisite writer, but who knows? It doesn’t concern me. I’ve got time,” he says.

“Eric left for one of the great jobs in Washington. Good money, campaign travel, and a lot less work. I would have told him to take it if he asked. And the other guy left because Eric left,” he says.

Regardie says that in terms of editorial development, he gives the magazine a “B, B-plus.” The advertising is a different story: “We are a little behind. I’m used to running a magazine that has 100 to 150 advertising pages in it, and we are a long way from that, but it’s not a big deal. We broke four major advertisers this week….They want in because they like what they see.”

Funny thing about Regardie: When he mentions that he’s hiring an art director, ironing out distribution problems, and publishing on more lavish paper stock, you believe him. He didn’t give up long afternoons in Palm Springs to throw a bunch of money down a rat hole. He and publisher/wife Renay think they can ride the next boom in Washington.

But all the brand recognition and credibility Regardie built up via previous iterations of his magazine are lost on local business’s new techie generation. They’re less image-conscious than the developers that Regardie’s used to cover, and many wouldn’t know Bill Regardie if he punched them in the nose. (And he’ll have a less than clean shot at them now that the Post has launched Washington Techway, a twice-a-month mag aimed at the same bunch.) But Regardie isn’t the least bit worried. Retirement didn’t suit him—”Who wants to start drinking at noon?”—and he’s got enough money at his current burn rate to last three years at least.

Lunch ended, and we flipped a coin to see who got the bill. Regardie lost, but then, he says his luck is changing.

Do as He Does For the past couple of years, most of Post Managing Editor Steve Coll’s writing has been confined to memos about the value of narrative. But he offered a slightly more powerful message when he assigned himself out to a Post Sunday magazine story about the political violence in Sierra Leone last year. Coll visited the country for two weeks and eventually found “General Mosquito” Bockarie, the Revolutionary United Front leader who apparently was one of the people who decided that chopping the limbs off of noncombatants constituted appropriate political discourse.

Coll wrote a really good story, full of the kind of storytelling he’s always chanting about. The first part was all gravitas and perspective—it’s hard to get to tricky when you are talking to people with no hands—but his meeting with Mosquito worked the gonzo literary space between Heart of Darkness and Fear and Loathing to nice effect.

Given all the pep talks he’s given on writing, you’d think Coll would be a little nervous about cracking the knuckles and sitting down to a blank screen. “I wasn’t worried about how it would be perceived in the newsroom, but I was worried about how rusty I would be. Five years is a long time. But it worked out, I think.” Coll plans on keeping his day job, but he says he would like to occasionally trade his editor’s pen for a reporter’s notebook.

A reporter at the paper who enjoyed the piece liked the symbolism, as well: “It sends a good message…that no matter how far you crawl up into the coil of this place, you still can still consider yourself a writer.”

Constitutional Amendment Nat Hentoff, whose constitutional-issues column started appearing in the Saturday Post about the time the Bill of Rights was first penned (1984, actually), is through. “[Editorial Page Editor] Fred Hiatt called and told me that he was thinking about running it every other week, and that’s when I knew that it was ‘So long, been good to know you.’ Then he told me that I could propose columns occasionally—which is a little like being an alien without a green card,” Hentoff says.

His column will continue to be syndicated to 250 papers, according to Hentoff, and he plans on appearing in the Washington Times locally if things work out. Hiatt, who was appointed editorial page editor in September, is even more circumspect about the change than he is in most of the editorials he publishes: “The Op-Ed page is going to continue to evolve, and that means bringing in new people, and you have to make room for some of those new voices.” —David Carr

E-mail Paper Trail at dcarr@washcp.com or call (202) 332-2100.