However, history hinted at what was to come, as Apple inched toward dominance and eventually overtook Microsoft in the computing market by 2010.
A full decade at odds
By the mid-2000s, Jobs had returned to his old ways, and he chastised Microsoft for "copying Google and Apple" despite having a $5 billion annual research and development budget.
A seminal moment occurred in 2007 when Gates and Jobs jointly took the stage for an interview at the D5 conference. The appearance is considered one of the most significant moments in the history of technology. But before the panel with Gates, Jobs couldn't resist taking a jab at Microsoft during a one-on-one interview with journalist Walt Mossberg. "We've got cards and letters from lots of people that say iTunes is their favorite app on Windows," Jobs said. "It's like giving a glass of ice water to somebody in hell."
Later, the joint interview kicked off with a question about the companies' contributions to the PC and technology industries. Jobs leaned forward, scratched his head, and said: "Bill built the first software company in the industry … Bill was really focused on software really before anybody else had a clue it was the software."
Gates offer clear praise in his response. "What Steve's done is quite phenomenal," he said.
Jobs warmed up eventually and acknowledged the long, rocky relationship between the two men when asked to describe the their greatest misunderstanding. "I think of most things in life as either a Bob Dylan or a Beatles song, but there's that one line in that one Beatles song — 'You and I have memories longer than the road that stretches out ahead' — and that's clearly very true here," he said.
Opportunities in enterprise rekindle old flames
A new era of partnership buoyed by opportunities in the enterprise blossomed during the past couple years. With new leaders at the helm of both companies came an end to the insults and grandstanding … for now, at least. The past month saw three separate events that demonstrate the companies' new commitment to compromise and combined efforts.
At Apple's September 2015 new product event in San Francisco, the company invited a Microsoft executive on stage to demonstrate Office 365 apps working in split-screen mode on an iPad Pro. At Salesforce's Dreamforce conference a week later, Microsoft CEO Satya Nadella demoed the company's iOS apps on an iPhone. And finally, during a keynote at cloud-storage company Box's BoxWorks conference in late September, when asked about the company's renewed relationship with Microsoft Apple CEO Tim Cook said he doesn't believe in holding grudges.
Microsoft's surprise on-stage presence at an Apple product event showed just how cordial relations have become between the two tech giants. When Nadella used an iPhone on stage at Dreamforce, he acknowledged such a thing would have been unheard of in the past but also used the opportunity to pump up his own company. "I like to call it the iPhone Pro because it has all the Microsoft software and applications on it … It's pretty amazing."
Sign up for CIO Asia eNewsletters.