The return of the prodigal sons

I'm not talking about the venture capital hotshots like Vinod Khosla. Betting with other people's money takes nerve, insight and luck, but it's just not the same as founding a start-up-turned-megahit.

Tough to come up with an A-list, isn't it? Still, armchair historians have a rare opportunity now to judge whether two of technology's more storied PC entrepreneurs may make the list. Ted Waitt and Steve Jobs are giving it a second whirl at their former digs. So what better time to examine whether these guys are really as good as their early clips, or whether their early fame had to do with something other than sheer entrepreneurial genius.

No doubt much of the early successes enjoyed by Waitt and Jobs had to do with serendipity. In Waitt's case, for example, Gateway can thank IBM for the congenital wrong-headedness that passed for a PC strategy in the late 1980s and early 1990s, allowing a mail-order upstart--along with Dell Computer--to help turn the concept of PC marketing on its head.

The same might be said for Apple, which got into the market several years earlier, benefiting from an artificial lead time as other would-be entrepreneurs--as well as tech stalwarts like Big Blue and Hewlett-Packard--simply failed to recognize the potential of this boxy machine called a personal computer.

But it's also no dishonor to get dealt a good hand. Gateway and Apple were built on more than luck alone. Besides, you make your own good fortune, and if these two guys were really such dim bulbs, I dare say Waitt would be tending cattle back on the South Dakota range, and Jobs would be handling camera orders behind the counter at Fry's.

At different points in their careers, each company co-founder gave up his day job: Waitt left in January 2000 on his own terms, and Jobs was forced to yield to his erstwhile buddy John Scully in a messy, 1985 boardroom putsch.

Now they're both back at the helms of their respective companies. While it's still way too early to render a final judgment, sideline handicappers would have to give the nod--at least so far--to Jobs and Apple.

Here's why:

When Waitt returned to Gateway, he rid senior management of most of the faceless suits who took over during the abbreviated reign of Jeffrey Weizen, replacing them with handpicked vets. The idea was to get back to Gateway's roots.

The problem is that the industry has moved so far beyond Gateway's roots that it's not at all clear how a return to the company's origins helps. Gateway sugarcoated its announcement to whack 25 percent of its staff as a continuation of its "beyond the box" strategy. But the massive retrenchments were really about cutting expenses faster than the concomitant decline in revenue.

There's really nothing anymore that distinguishes Gateway boxes from the next guy's. It used to be that the company's goofy-yet-endearing print commercials and cow-spotted boxes inspired something of a cult following. More than that, Gateway often stayed ahead of the pack because of its close association with Intel and was thus among the first to market with aggressively priced systems that came out in faster speeds than those offered by rivals.

That's ancient history. These days everybody's to market at the same time when a new chip comes off the production line at Intel or AMD. And in the teeth of a withering price war, Gateway can't fall back on non-PC divisions to offset the crushing impact of beggar-thy-neighbor competition. Sorry, but selling training, software and services to consumers just isn't going to be enough to rescue Gateway from oblivion. There's got to be more, and it's up to Ted Waitt to figure that out--and fast.

On to Apple, where the company faces many of the same problems encountered by Gateway. But though Apple remains a minor computer player these days with finite customer appeal, that may be its biggest strength.

Mac users just dig the interface. Period. Don't bother engaging them in rational discussions about the respective merits of the PC vs. the Mac. It's a lifestyle thing, and that's the reason Apple ought to feel really good about the future--or at least a lot better than how Gateway must feel.

Under Jobs, the company has added a few cute bells and whistles in terms of design and color. Then there are the more substantive innovations embodied in Mac OS X and, especially, the iPod music player. It's still too early to gauge the potential success of the iPod, but, like the Palm, it just might take off as a tidy entry in the consumer electronics world.

Best of all, none of Apple's products may be cloned--not legally, at least. Early into his second coming at Apple, Jobs made sure to stop the clones dead in their tracks. For the wrong reasons, he'll probably turn out to have been right.

But Jobs' most indelible contribution to Apple's fortunes was the turnaround he engineered after conspiring to get the board to dump Gil ("Company Doctor") Amelio. Some of it was smoke and mirrors, but it worked. He did his damnedest to foster the perception that, yes, Apple products were better than run-of-the-mill PC products. And in the company's darkest hours, that helped spell the difference between survival and utter collapse.

Now Ted Waitt has to do something along the same lines. Only in his case, the challenge is five orders of magnitude more difficult.