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SAN JOSE, Calif. - Bill Gates and Steve Jobs will share a stage Wednesday night for the first time in more than 20 years to talk about technology’s present and future, but it’s their intertwined and competitive past that makes the historic event so dramatic.


Longtime rivals, the two have had distinctively different approaches to technology since the birth of the personal-computer industry. Gates, as co-founder of industry heavyweight Microsoft, has long sought dominance over the desktop with products that strive for ubiquity, not uniqueness. Jobs, as co-founder and now chief executive of Apple, revels in his company’s penchant for path-breaking design, even as its market share lagged far behind his bigger rival.


Given that history, the audience for the sold-out show in Carlsbad, Calif., that is part of the D: All Things Digital conference, an event sponsored by the Wall Street Journal and hosted by high-profile technology columnist Walt Mossberg, will be hoping for something momentous. Even at an event billed as a public “conversation,” Gates and Jobs could fight to define the industry’s future.


“Both have had differing visions of the world,” said Rob Enderle, principal analyst at the Enderle Group, a consulting firm in San Jose. “There’s a certain amount of aggravation (with each other) that’s carried through over the years.”


Their history is the industry’s history. Each started his company when a PC was little more than a gadget for geeks. Each man’s company in its own way helped bring the PC to the mass market, bringing down its cost and complexity for the end user.


But they had distinctly different ways of doing that. Apple and Jobs cultivated the role of the rebel, the iconoclast, the aesthete. Under Jobs, the company willingly abandoned old technology, old ideas, even old users in the cause of design elegance or improved ease of use.


Though Microsoft was an upstart like Apple, it took a different route under Gates. Instead of challenging the establishment, Microsoft cooperated with it almost from the beginning, getting its first big break by joining with IBM to load Microsoft’s operating system on IBM’s PCs.


That’s not to say Microsoft - or Gates - always played well with others. The company’s relationship with IBM soured in the late 1980s, for instance, and it was sharply criticized by rivals and partners alike for its business practices during its 1990s antitrust trial.


But the company became a behemoth by working with partners to make sure its DOS and Windows operating systems were the PC standard.


The result: Jobs’ company made the simple but elegant machine that most everyone loved but few used; Gates made the software that everyone used but few loved.


Like their companies, the two men have distinct personalities, which perhaps can be seen best in their public appearances. Widely regarded as a master showman, Jobs seems never so comfortable as when he’s on a stage in front of thousands, touting his latest product. In contrast, Gates often appears awkward or uncomfortable on stage, even when he’s giving his vision of the future.


But for all their differences, the two - and their companies - have some remarkable similarities. They’re about the same age. Both are college dropouts. They’re widely regarded as brilliant and creative. They both can be charming, but have reputations for being frequently difficult or even abrasive. And they’re both arrogant and extremely ambitious.


That latter trait most likely served their respective companies well. They not only founded two of the seminal companies of the PC era, but they each helped ensure that their companies survived and thrived.


And despite their well-known professional rivalry, the two were friends, at least for a time. In the 1980s, they even double-dated and were close enough that Gates jokingly left prank phone messages on Jobs’ answering machine, said Alan Deutschman, author of “The Second Coming of Steve Jobs.”


“They have always had a complicated relationship,” Deutschman said. “They were never bare-your-soul confidants, but they were always intrigued with the other.”


Their joint appearance comes at a moment of transition. Since the mid-1970s when the two companies were founded, the PC business has grown into a mature industry.


Microsoft still dominates the PC software business, but it is investing heavily in other areas, from video game consoles to mobile phone operating systems to software for set-top boxes.


Apple, too, is changing. The bulk of its sales growth in recent years has come from its iPod music players. And now it’s adding a mobile phone and a set-top box to its lineup of products. The company even dropped “Computer” from its official name in January.


The two tech titans come to the conference - and will leave it - heading in distinctly different directions. Gates is increasingly focused on his foundation, to which he has committed the bulk of his wealth. While Jobs is still steering Apple, the company’s direction is shifting increasingly away from the PC and toward the media and consumer electronics industries.


That’s not to say that either man has set aside his ambition. Indeed, both appear merely to have taken up new challenges. Jobs is angling for Apple to be the dominant player in the digital media industry, building on its early lead with the iPod.


Gates, meanwhile, wants nothing more than to change the world, using his largess to attack poverty and disease in Africa and the Third World.


“They both still have the fire. They’re not just going off and playing golf somewhere,” Deutschman said. “These are guys that like being behind big change. It’s what drives them.”

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