January 13, 2000: Steve Jobs’ longtime frenemy Bill Gates steps down from his role as Microsoft CEO, one month after his company hit its all-time share price high.

The news coincides with a turning point in the long-running battle between the two companies. Microsoft begins a long decline from its previous dominance, while Apple continues its rise to power.

Bill Gates and Steve Jobs: Parallel careers

For good reason, we focus on Apple events for this daily feature. With that said, Gates stepping down as Microsoft CEO did prove an important occasion for the entire PC industry.

Born in 1955, the same year as Jobs, Gates’ first major success was in his role developing applications for the original Macintosh.

These were viewed as so crucial to the Mac’s success that, after Jobs was pushed out of Apple, then-Apple CEO John Sculley signed a deal with Gates to give Microsoft “non-exclusive, worldwide, royalty-free, perpetual, nontransferable license to use [parts of the Mac technology] in present and future software programs” for the fledgling Windows operating system.

In return, Microsoft had to continue developing Word for Mac and delay porting Excel to Windows for one year.

It was a horrendously lopsided deal, as it turned out. And when Microsoft finally got its act together and started making Windows faintly competitive with Mac OS, the agreement triggered a long-running lawsuit over whether Microsoft was stealing the Mac’s “look and feel” to create Windows.

Microsoft came out on top. Throughout the 1990s, the company’s strategy to license its technology to third-party manufacturers rather than making hardware made Microsoft an almost unassailable tech giant. When Apple eventually gave in and tried the same strategy, it backfired — leading to the disastrous “clone Mac” era.

Microsoft and Apple: Great rivals

Gates and Jobs were often positioned publicly as enemies, although they were more like rivals. Both got in on the ground floor of the PC industry. And both received media coverage as individuals in a way that a lot of tech execs don’t today, when products tend to speak for themselves.

Both had seen plenty of ups and downs over the decade before Gates handed over the Microsoft CEO position to Steve Ballmer. For evidence, check out their first joint interview for a 1991 issue of Fortune magazine (which I wrote about here).

Just nine years before Gates quit as Microsoft CEO, he was riding high and Jobs was the man running two failing companies: NeXT and Pixar.

When Gates stepped down as CEO, he said he would stay on as “chief software architect.” He gave up day-to-day responsibilities at Microsoft in June 2008 to work on his charitable ventures.

One possible reason behind his decision to leave his job as CEO: Microsoft faced increased antitrust scrutiny, which undoubtedly made the job less fun than before.

Jobs, by comparison, stayed as CEO at Apple until just a few short months before his death in 2011.

Were you an Apple or a Windows user (or neither) in January 2000? Leave your comments below.

From chairman to chair man

Oh, and just because it’s the weekend, here’s a video of Bill Gates jumping over a chair:

Genius!