Y2Ka-ching!

J. David Stewart has big plans to cash in on doomsday. Come the new millennium, he'll be "Y2KMAN" (as the vanity plates on his '68 Corvette convertible announce), driving fast and furious into "Y2CHAOS" (as the tags on his '69 Ferrari 365 GT put it) and snatching huge profits from the jaws of calamity.

That's "Y2K" as in Year 2000, a reference to the so-called millennium bug -- the global computer glitch that's either been underestimated or over-hyped, depending on whether you believe it will bring the world to its collective knees or pass as a minor data hiccup.

And Stewart's just one in a clutch of Y2K investment gurus betting on the disaster scenario. "Entrepreneurs of apocalypse," you might call them -- and they're galloping to a bookstore near you faster than the four horsemen. Surprisingly, none of these guys has a late-night infomercial. They do, however, have the latter-day equivalent: Web sites promoting their books. You see, they all offer self-published tomes that promise to make you a king's mint off the Y2K disaster. In the true spirit of American enterprise, Stewart, along with other authors like David Steelsmith Elliott and Charles Steed, has discovered an upside to the "end of the world as we know it." Y2Ka-ching!

Stewart, a securities analyst whose home, business and yacht are anchored in Dana Point, Calif., was the first to market, with his evocatively titled "Date Rape 2000: Investing in the Crime of the Century." Though the trade paperback will set you back $29.95, that's apparently a small price to pay for "capitalizing fully on the spectacular payday immediately ahead."

Elliott, an ex-Navy man in Tacoma, Wash., and Steed, a survival-minded real estate speculator who hails from farther north in rural Puget Sound, subsequently weighed in with their own takes on fiscal Armageddon. Elliott's book, "Everybody's Guide to Making a Million Dollars in the Year 2000 Computer Crash," assures readers that they can amass "$15,000 to 2 MILLION DOLLARS" off the coming crisis. Steed's entry, "Crash Course 2000: How to Prepare for and Prosper From the Y2K Computer Crash," combines predictions of inner-city rioting with "sure-fire real estate investment techniques" to make you rich when the bottom drops out of civilization.

To be sure, all three are hunkering down for the run-of-the-mill, Irwin Allen-style disasters that preoccupy most Y2K soothsayers: the power outages, the frozen elevators, the food shortages. But what sets these guys apart from other digital millennarians -- like the folks doing a fast business in canned victuals and butane stoves -- is their interest in the big picture. Forget about the expected traumas of Jan. 1 or 2; these guys are looking ahead to an ample calendar year's worth of business upheavals -- and the profits they plan to make off them.

The three make no apologies for banking on disaster. Stewart is particularly proud of his acumen when it comes to "finding opportunity in calamity," as he puts it. "Personally, I enjoy crisis investing," he writes, "and frankly, I seem to have a knack for it." Not only did he "make a killing of my own" by buying deflated Johnson & Johnson stock in the wake of the "Tylenol-poisoning tragedy," he struck gold after the space shuttle Challenger explosion, "by shorting Rockwell -- almost before their rocket motors hit the ocean."

If onlookers find fault with the authors' ambulance-chasing styles, so be it. What galls these guys is not moralistic tongue-clucking but the suggestion that they might be wrong about the potential Y2K fallout. Stewart, along with Y2K consultants Kevin Schick and Peter de Jager, has been accused of exaggerating the scope of the Y2K problem. As early as 1996, Fortune magazine labeled Stewart the person "most responsible for unleashing the Year 2000 problem on the investing public."

Elliott, too, has taken his share of hits from critics. "But I've got more hours investigating Y2K than most people out there," he bridles over the phone, "including all the reporters I've talked to."

By way of vindication, Elliott points to a May 24 stock market drop in response to a Wall Street analyst's unusual report recommending that investors unload multinational banking stocks. According to the Credit Suisse First Boston report, those bank stocks could be vulnerable to Y2K problems abroad. If that report alone was enough to knock the Dow Jones industrial average down by 174 points, says Elliott, imagine what will happen when the real Y2K shock kicks in.

As further evidence that the potential for disaster has been greatly underplayed, both Elliott and Stewart are eager to cite recent reports that government agencies and corporations are alarmingly ill-prepared when it comes to fixing their Y2K bugs. For instance, notes Elliott, the Weiss Ratings, which monitor corporate Y2K readiness, reported early in May that some of the nation's largest companies -- including telecommunications giants and two of the Big Three automobile makers -- are far behind on their Y2K repairs. Martin Weiss, chairman of Weiss Ratings Inc., put it this way: "The poor progress made by so many of America's largest companies comes as quite a shock, implying potentially serious disruptions in the operations and profits of at least some of these companies."

So it seems that Stewart, Elliott and company may be somewhat closer to the mark than their critics have given them credit for.

And what, exactly, are Stewart, Elliott and Steed predicting? Basically, a worldwide depression. "Y2K," announces Elliott, "is multifaceted, any one facet of which could crash the stock market."

Stewart and Elliott both make persuasive cases for the boggling degree to which the Y2K-susceptible machines that govern our daily lives are intimately interconnected. As many a programmer has found since news of the millennium bug first broke, all it takes is one ill-prepared system to create a ripple effect with broad consequences across the rest of the world.

"Fifty percent of Germany's corporations aren't going to be ready for Y2K," says Elliott. "If Germany gets whacked by Y2K, what happens to our stock market? Japan's economy is totally dependent on imported oil. If Japan doesn't get that oil, it will have direct repercussions on our own economy."

As a textbook example of the ripple effects of foreign Y2K fallout on U.S. soil, Stewart and Elliott both single out the Detroit auto industry. The Big Three automakers all rely on an extremely complex chain of offshore vendors to supply the parts necessary to build a car. Even if Detroit manages to fix its own Y2K bugs by January 2000, it's not likely that many of the foreign suppliers will.

With that supply of parts at risk, says Elliott, "I predict that General Motors is not going to be making an automobile from January through March 2000. I'm going to be buying put options on General Motors, Ford and Chrysler," he says -- betting that their stock will plummet in the new year.

Then there's the issue of transportation: "The railroads are the scariest of all," says Stewart, referring to the fact that piloting people and freight in the United States is now totally reliant on complicated, computer-controlled routing systems. In the past, freight cars were coupled and routed to their destinations manually, by switchmen in switching yards. A decade ago, however, the old system was entirely dismantled.

"We don't have any switching yards," says Stewart after lighting up another in an endless series of Marlboros. "We don't have any switchmen! It's a computerized activity. Without the computers nothing happens. Even if all the nations were Y2K compliant, and if Detroit got all the parts, from all the nations, and if all the embedded microchips in all the robots that make the cars were fixed -- if!" he shouts. "Could they actually get the trains to get the cars to the West Coast, to sell the product?"

And with businesses going sour in thousands of similar ways, wouldn't the entire economy be tanking? he asks. "In the Y2K economy, do you think that there are going to be people with money to even buy these cars?! Get real!"

Of course, as critics have pointed out, there are enough mitigating factors to make the most dire Y2K predictions unlikely. For starters, although the bug is widespread, the fixes are relatively easy to implement; and with so many programmers focused on the task, the worst scenarios now seem unlikely. (Earlier concern over "embedded chips" -- microchips inside appliances like VCRs, stoplights and factory equipment -- has eased in recent months. Even Y2K watchdog Peter de Jager says that "most [embedded systems] won't fail.") In the meantime, stock exchanges, airports and others have been fixing their systems, pushing their clocks ahead to January, testing -- and passing with flying colors.

Still, Stewart and Elliott dismiss such arguments as being woefully less well-researched than their own authoritative conclusions.

Stewart calls all this "the kind of scenario that makes for ugly reading, but beautiful profits." And despite the obvious trauma that his forecast entails -- the fall of governments, the urban rioting, the global depression -- Stewart can't help sounding a bit gleeful. "This is going to be the greatest transference of wealth in the history of mankind, period!" he enthuses.

Does that mean he plans to be lighting fat-cat stogies from flaming hard drives while the rest of the world burns? No, sir. He insists that he really wants to help people make the best of a tragedy. "Even someone as mercenary as myself," he explains, "realizes that you and I have a responsibility that sincerely extends to people's welfare. We're all going to be severely inconvenienced by Y2K, so we may as well profit from it. And we may as well try to do it with some style."

Stewart -- who favors a ponytail, goatee and highly amplified classic rock from the '70s -- is all about style. A near-life-size limited edition Cibachrome print of the Marilyn Monroe centerfold from the very first issue of Playboy, signed by Hugh Hefner, adorns a wall in his office. In fact, Stewart says he has endeavored to model his life on that of Hefner, his idol. And like Hef, who "had the courage to take art across state lines when it was very illegal," Stewart isn't much concerned with uptight busybodies who might take a dim view of his own morally ambiguous plans to create major cash flow. In short, he cuts rather an unlikely figure as a high financier.

Still, a well-heeled phalanx of Wall Street fund managers, stockbrokers and accountants subscribe to his investment newsletter, the Stewart Report, which specializes in hedges against a potential Y2K meltdown. No less an authority in the Y2K world than Rep. Constance Morella, R-Md., chairwoman of the technology subcommittee of the House Science Committee, takes Stewart's newsletter. A number of onetime celebrities eager to hang onto their capital gains are also subscribers, including Henry "the Fonz" Winkler, Chad "Medical Center" Everett and Tommy "not Cheech but the other guy" Chong.

Stewart's advice to erstwhile celebs and average people alike: Dump your blue-chip stocks immediately. He predicts a major stock market plunge well before Jan. 1, 2000 -- when Wall Street finally figures out the true breadth of the Y2K problem. Unload your real estate before that market collapses, too. Then go on a home-buying spree next year, snapping up deals at fire-sale prices, "when cash is king!"

Elliott and Steed offer basically the same advice -- and claim to be practicing what they preach. All three say they have dumped or plan to dump most of their real estate holdings. Steed explains that he's hanging onto his rural ranch as a safe haven from urban upheaval. Elliott and Stewart plan to whisk themselves away from "Y2CHAOS" on board their respective yachts.

All three also advise savvy Y2K survivors to invest in gold and silver, buy put options on stocks that are going to be headed down and grab up stocks they believe will actually increase in value. (Elliott thinks that domestic oil companies will do well because foreign oil will be dicey; Steed sees mining concerns as sure-thing investments, expecting gold and silver to soar in value.)

Beyond all that and stockpiling storage units with bottled water, Stewart advises Y2K warriors to have a ball while "turning a lemon into lemonade."

"I'm going to go bargain hunting, post-Y2K," says Stewart. "That's the whole name of the game, to get liquid, to get really relaxed, to go have some fun. Wait for it to fall out of bed. Because whatever you buy in the year 2000, you're buying at the bottom."