April 4, 1975: Childhood friends Bill Gates and Paul Allen found Microsoft Corporation, a software company destined to become a tech behemoth — and a major Apple frenemy.
A few years later, Microsoft will break through to the mainstream with Excel and Word, becoming a key developer of Macintosh software. Then comes the Windows operating system, looking suspiciously Apple-like. After that, Microsoft and Apple will embark upon a long-running feud.
March 17, 1988: Apple sues Microsoft for allegedly stealing 189 different elements of its Macintosh operating system to create Windows 2.0.
The incident, which causes a deep rift between Apple and one of its top developers, paves the way for an epic battle between the two companies that will rage for years.
February 11, 2010: With iPad excitement reaching a fever pitch, Steve Jobs’ old frenemy Bill Gates wades in with his own opinion of Apple’s tablet.
His view? It’s kinda meh.
“There’s nothing on the iPad I look at and say, ‘Oh, I wish Microsoft had done it,'” he tells one interviewer.
January 13, 2000: Steve Jobs’ longtime frenemy Bill Gates steps down from his role as Microsoft CEO, a month after his company’s stock hit its all-time high.
The news coincides with a turning point in the long-running battle between the two tech powerhouses. Microsoft begins a long decline from its previous dominance, while Apple continues its rise to the top.
December 30, 1999: Microsoft hits the height of its 1990s dominance and begins its early-2000s decline, clearing a gap at the top for Apple.
After hitting its all-time high of $53.60, Microsoft stock starts to fall. Less than a year later, Microsoft shares fall more than 60% in value to $20.
November 26, 1984: “The next generation of interesting software will be done on the Macintosh, not the IBM PC,” claims Microsoft co-founder Bill Gates in a BusinessWeek cover story.
The claim would seem almost unthinkable coming out of Gates’ mouth just a few years later. But it comes at a time when Microsoft is best known as one of the biggest Mac developers.
November 21, 1985: Following Steve Jobs’ departure, Apple comes close to signing its own death warrant by licensing the Macintosh’s look and feel to Microsoft.
The deal, between Microsoft co-founder Bill Gates and Apple CEO John Sculley, comes hot on the heels of the Windows operating system’s release. The pact gives Microsoft a “non-exclusive, worldwide, royalty-free, perpetual, nontransferable license to use [parts of the Mac technology] in present and future software programs, and to license them to and through third parties for use in their software programs.”
Oh, boy!
August 26, 1991: In their first joint interview, Steve Jobs and Bill Gates trade barbs and debate “the future of the PC” in Fortune magazine.
The spirited discussion marks 10 years since the first IBM PC shipped. The piece also looks at what the future holds for both men — described as the former “boy wonders of computing, now thirtysomething.”
The companies they helped found might have been sworn enemies at times, but Steve Jobs and Bill Gates didn’t hate one another. In fact, as the former Microsoft boss admitted on a recent podcast, he was actually jealous of Steve Jobs.
Appearing on the Armchair Expert podcast, Gates told actor and podcast host Dax Shepard that Jobs was a “wizard” when it came to motivating people. “I was a minor wizard so I couldn’t fall under his spells,” Gates said. “But I could see him casting the spells, and then I would look at people and see them mesmerized … I was so jealous.”
August 21, 2008: Microsoft recruits comedian Jerry Seinfeld for a series of ads. It’s a naked attempt to shake the company’s reputation as a stodgy oldster (as opposed to Apple’s trendsetting hipster image).
Microsoft pays Seinfeld a reported $10 million for the ads. However, thanks to the Mac’s appearance in virtually every episode of Seinfeld over the years, the comedian remains the world’s most famous Apple fanboy.
