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The print version of Who Wants to Marry a Billionaire? stars MicroStrategy’s Michael Saylor—a newspaper dream date with a big mouth, endless ambitions, and wired gazillions. The Washington Post, for one, hasn’t played coy: Oh yes, Michael, tell us about your fabulous Oscar party and your 50-acre front yard. Bring on those aphorisms about how the miracle of “data mining” will set us free while collecting our most private information. And while you’re at it, explain how the velocity of digital business outstrips the capacities of common accounting principles.

Saylor is apparently programmed to never shut up. In the midst of a “quiet period” mandated by the Securities and Exchange Commission after the company filed an additional public stock offering on March 6, Saylor used the Post, his ever-attendant paramour (and business partner—but more on that later), for a front-page announcement of his new $100 million online university. Saylor also penned an Op-Ed shilling for a version of the future that would accrue to MicroStrategy’s bottom line.

Oh, and he did something else sort of newsworthy: On Monday, March 20, Saylor suffered a one-day personal loss of $6 billion in paper wealth. John Paul Getty used to say that if a guy could count his money, he wasn’t really wealthy. By that standard, Saylor is royally flush. After last week’s macrocorrection at MicroStrategy, his billions have become temporarily ineffable.

A Post editorial on Wednesday blamed MicroStrategy’s outside auditors, never mind the people inside the company who had approved overheated revenues. People like Ralph Terkowitz, who serves on MicroStrategy’s board and was one of two people on the audit committee who OKed both the numbers and the auditors, according to sources familiar with the company. In his day job, Terkowitz serves as vice president of technology at the Washington Post Co. His name never managed to come up in all of the coverage, though.

That isn’t the only part of the story the Post missed or chose not to tell.

For whatever reasons, like would-be Mrs. Millionaire Darva Conger, the Post ignored ample signs that things were getting ugly backstage. The paper underreported the implications of MicroStrategy’s recent business decisions and continued to treat Saylor more like Marlene Cooke than Bill Gates. The Post’s celebrity-sniffing tendencies and growing conflicts leave it underequipped to report on the thermodynamics of the new economy, which will require a market drop as mighty and awe-inspiring as the run-up.

There’s something sad about seeing the first dot-com tycoon the Washington Post really fell for tumble so fast. (OK, his stock has rebounded, and you still need eight figures to get to the end of his net worth, but the smirk has been supplanted.) Until MicroStrategy’s Black Monday, Post readers knew Saylor primarily through steaming Saylor-facts in the Reliable Source and craven ass-kissing in the Download, the Post’s weekly tech-worshiper column.

“I think that we let the cult of personality carry the story for the last three years, and we need to get beyond the gee-whiz stuff about rich guys and demonstrate the kind of rigor that you’d expect when you are covering businesses that are going to change people’s lives,” says one reporter at the paper.

“Everybody in the business confronts the same problem,” says Kara Swisher, the Wall Street Journal Boom Town columnist who was once a Post reporter and is the author of aol.com. “[In Silicon Valley,] we have 19 magazines that read like corporate porn. We all should think hard about how we are covering these guys, because the money is so huge that it’s hard not to be overwhelmed by it. It’s easy to mistake money for intelligence,” she says.

Swisher remembers a time at the Post when she switched from covering one generation of Washington wealth—the Hafts—to the next generation—Steve Case and America Online. “There wasn’t a commitment at the time. The editors at the Post kept waiting for me to write the story about the death of AOL, and I kept telling them that AOL was going to have their market cap one day.”

Back when people had to buy and sell goods to get rich, newspapers didn’t have much trouble keeping track of them. It was especially easy in Washington, a town where the coin of the realm wasn’t coin, but power. As Slate’s Jack Shafer points out, there were just a handful of families in pre-tech Washington—the Hechingers, the Hafts, the Cafritzes—and if they bought or sold one of their enterprises, or got divorced, or croaked, well, you just wrote ’em up.

Covering the digitally wealthy is tougher business. Because of the scale involved, when they screw up, the consequences are market-shaking. It’s hard to get used to the fact that anybody in Washington besides Alan Greenspan can have a financial impact on the rest of the world.

The Post has done a better job of e-skepticism beyond its delivery area. On March 19, the day before MicroStrategy’s historic free fall, the Post’s David Hilzenrath wrote a smart takeout on how some dot-coms—including a North Carolina company called SciQuest—puffed up revenue to keep stock prices skyrocketing. Unfortunately for Post readers and MicroStrategy investors, Hilzenrath didn’t mention the obvious local exemplar of creative revenue management.

The story was already out there. In early March, Forbes writer David Raymond suggested that MicroStrategy’s general aggressiveness included booking long-term contracts to short-term ends. Finally, under pressure from its auditors, Saylor’s company announced that it was lowering 1999 revenue estimates by $50 million. The market, ever responsive to Saylor’s whims, hammered the company’s share price down from a close of $226 on Friday, March 17, to $72 the day of the announcement. Its $23 billion market cap became a much smaller beanie, falling to a little more than $5 billion.

“We would have loved to have had something about MicroStrategy before it happened,” says Post Business Editor Jill Dutt, “but we hadn’t yet confirmed what Forbes reported. We assigned David [Hilzenrath] to do something about aggressive accounting at Internet companies, and SciQuest was the best example we had good facts for.”

When the crash came, Hilzenrath did a postmortem that offered a good portrait of how the runaway stock went flying off the tracks, but the story shared front-page space with a curious mood piece about the boy billionaire. “It feels like nothing, actually,” the man who had just lost $6 billion in vapor wealth told the Post’s Mark Leibovich. MicroStrategy Chief Operating Officer Sanju Bansal described the folks at the data-mining firm as “unexplainably buoyant.”

Investors who participated in the $18 billion haircut probably didn’t have the same bounce in their steps. The day of the drop, five law firms filed suit on MicroStrategy investors’ behalf, alleging that the firm had filed “materially false and misleading financial statements that materially overstated the Company’s revenue, earnings and income,” according to Keith Perine’s Industry Standard story.

Saylor told reporters that the company had “clarified” earnings to make sure it was compliant with new SEC rules. But a SmartMoney.com story that same Monday said that auditors PriceWaterhouseCoopers had threatened to withhold approval of previous financial statements if Saylor & Co. didn’t report revenues in a way that reflected actual fiscal realities.

Like any good propellerhead, Saylor had a technical excuse for the fiasco, suggesting that the new economy just won’t fall easily into the template of old-economy accounting. And he had some help from Terkowitz.

Terkowitz did not return calls for comment, but Post Managing Editor Leonard Downie says that Terkowitz works for the parent company on technology matters and has nothing to do with the paper or its coverage. And although the paper failed to mention that Terkowitz had played a role in approving the now-disputed audits, it did disclose in passing that “a Post Co. vice president” is on MicroStrategy’s board and that the company does business with MicroStrategy in something called the Strategy.com Network.

One of the downsides of “convergence” is that a newspaper that is also a big media company isn’t going to report business news for long without bumping into itself. The presence of Terkowitz at the heart of the MicroStrategy story seems especially troubling. Will he be named personally in the shareholder suits? Will the paper cover them aggressively if he is?

Saylor has said that he has many “levers” to achieve financial objectives and that inking deals near or just past the end of the quarter was one way the company was able to demonstrate a continual growth in revenues. Unfortunately for its investors, many of those deals were “back-scratchers,” transactions in which the company was merely trading or bartering services with another company and booking the transaction as pure revenue.

Post business writer Jerry Knight did touch on the Forbes report, but it was buried on Page 7 of the Monday Business tabloid. And other parts of the franchise were still granting Saylor permissions. Editorial Page Editor Fred Hiatt says he sees nothing wrong with the decision to give Saylor an Op-Ed column on March 14. The Post grants the courtesy to heads of state, he says, so why not captains of industry? “I think one of the legitimate uses of our page is to give space to different points of view, and the people who are the new corporate leads in the Washington area are voices worth giving exposure to. Our readers are capable of deciding how much self-interest is at work,” he says.

Other people at the paper say they were embarrassed. “[Saylor] has some absurd ideas and some good ideas, but we let him off the hook. The work his company does raises significant privacy issues, his accounting practices have been raising eyebrows for a while, and there is something really creepy about his corporate culture. I’m not sure we want somebody who is so much a part of the news to be writing for our paper,” says one staffer.

It could get worse. Sally Quinn, the Post institution whose profiles amount to the final word on what Georgetown salon society thinks, has been working on an admiring piece whose essential premise appears to be this: Good Lord! There are rich people in Washington who haven’t ever been to my house for dinner! Quinn’s story is still lurking in the paper’s publishing queue, where more than a few staffers hope it will stay. Which isn’t to say that there haven’t been some in-office readings of the epic. “Now, the realization that those people across the river could, might, probably will have a major impact on the capital of the United States has many people wondering about their own status,” the story reads.

Do tell.

Downie says the paper’s neither insecure about nor romanced by electronic industrialists. “I think that if you ask the people at AOL, they will suggest that we have been pretty rough on them,” he says. “We have a lot of history of being pretty skeptical and aggressive about these issues.”

The Post is clearly still figuring out how to cover this financial insurgency in its back yard. Much of the coverage has been cultural, as opposed to financial. Watch Ted Leonsis buy a hockey team. Notice Mario Morino play pool and venture capitalist at the same time. Watch in amazement as Post tech columnist Shannon Henry gleefully dives into yet another roomful of filthy-rich nerds.

Having missed the nascent AOL story, a tectonic event that went off just up the road, the paper made significant steps in terms of staffing and resources under both previous Business Editor David Ignatius and Dutt.

And when it comes to regulatory matters—government continues to be a sweet spot for the franchise—the Post remains king. Its coverage of the Microsoft trial was unsurpassed. But institutional cluelessness still shines through. It can’t go tactical and do the kind of big, synthetic analysis that drives so much good business coverage these days. The bloodlust that defines its reporters on the political beat hasn’t infected many of the reporters on the business side. And the ubiquitous local presence of AOL didn’t save the paper from getting beat on the merger story by the Wall Street Journal.

God, it’s said, expresses his contempt for wealth by those upon whom he chooses to bestow it, but the combination of callow youth and limitless millions is a tough one to resist. “These are outsize characters that are intrinsically interesting, and we are always grateful for subjects our readers are going to find interesting,” admits Downie.

Saylor, for his part, may be up to his eyeballs in shareholder suits and under the microscope at the SEC, but don’t look for the meteor to come back to Earth. Apart from being a loudmouth, he’s brilliant, and unlike a lot of Net geniuses, he’s actually got a valuable proprietary technology. He seemed to anticipate the big ride—and the bumps that would go with it—almost a year ago in the Post, back in the dark ages when his stock was priced at just $25 a share.

“When the stock goes down, you get stripped of your resources, and the resources you need would be the people, the capital, and the attention and the credibility, and all of those things disappear if my stock crashes. On the other hand, if my stock soars, I get more of those things. If it’s in a range, it doesn’t really much matter,” Saylor said in a Q & A with the Post.

MicroStrategy’s stock closed down by 2 and a quarter on Wednesday afternoon.

Victimized Last Monday, Rufus Stancil showed up in a Post Metro story as “a well-to-do African American entrepreneur” who was discriminated against by the good old boys of Charles County when they blocked his effort to put together a post office building in La Plata. That’s news to some of his tenants back here in the District. And the city’s Water and Sewer Authority probably shared their surprise.

Stancil owes $200,000 in water and sewer bills on his various residential properties here. And according to Sczerina Perot, staff attorney at the Washington Legal Clinic for the Homeless, her clients at Stancil’s building at 2922 Sherman Ave. NW are about to get kicked out because the building is condemned as of April 19. “He doesn’t pay his utility bills, he has outstanding debts, and he doesn’t make repairs on his buildings. He’s victimized a lot of minorities back here in the District,” says Perot.

The reporter, Todd Shields, might have been forgiven for not looking into Stancil’s background—except that he wouldn’t exactly have had to come all the way from his suburban beat into D.C. to do it. All he’d have had to do was pick up his own newspaper. Two weeks before, Metro had reported the salient facts about Stancil’s properties in the District in a story about what the Post calls “reputed slumlords.” —David Carr

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