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Steve Jobs Bill Gates

Steve Jobs, left, and Bill Gates, right, were alternately allies and enemies throughout their tenures at Apple and Microsoft, respectively. Beck Diefenbach/Reuters; Mike Cohen/Getty Images for The New York Times
  • Microsoft’s Bill Gates and Apple’s Steve Jobs never quite saw eye-to-eye.
  • They went from cautious allies to bitter rivals to something almost approaching friends — sometimes, they were all three at the same time.
  • It seems unlikely that Apple would be where it is today without Microsoft, or Microsoft without Apple.

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Steve Jobs and Bill Gates were alternately allies and enemies throughout their tenures at the helm of Apple and Microsoft.

They’d gone back and forth complimenting and criticizing each other and each other’s companies. Still, the successes of their companies were undeniably intertwined.

Here’s a look at Jobs’ and Gates’ love-hate relationship over the years:

Bill Gates and Steve Jobs weren’t always enemies.

Microsoft and Apple were early collaborators. Flickr/Robert Scoble

Microsoft made software early on for the mega-popular Apple II PC, and Gates would routinely fly down to Cupertino, California, to see what Apple was working on, according to Walter Isaacson’s biography of Jobs.

In the early ’80s, Jobs flew up to Washington to sell Gates on the possibility of making Microsoft software for the Apple Macintosh computer, with its revolutionary graphical user interface, according to the biography. Gates wasn’t particularly impressed with what he saw as a limited platform — or Jobs’ attitude.

Steve Jobs leaning on the Macintosh personal computer following a shareholder’s meeting in Cupertino, California. AP Photo/Paul Sakuma

“It was kind of a weird seduction visit where Steve was saying we don’t really need you and we’re doing this great thing, and it’s under the cover. He’s in his Steve Jobs sales mode, but kind of the sales mode that also says, ‘I don’t need you, but I might let you be involved,'” Gates later said.

Still, Gates appeared alongside Jobs in a 1983 video — a “Dating Game” riff — screened for Apple employees ahead of the Macintosh’s launch.

The original “Dating Game” first aired in the 1960s. YouTube/All Things D

In that video, Gates compliments the Mac, saying that it “really captures people’s imagination.”

Microsoft and Apple worked hand-in-hand for the first few years of the Macintosh.

Gates’ and Jobs’ companies worked together at first. Paul Sakuma/AP

At one point, Gates quipped that he had more people working on the Mac than Jobs did.

Their relationship, already kind of rocky, fell apart when Microsoft announced the first version of Windows in 1985. A furious Jobs accused Gates and Microsoft of ripping off the Macintosh.

Their relationship took a turn in 1985. Reuters/Jeff Christensen

But Gates didn’t care — he knew that graphical interfaces would be big, and didn’t think Apple had the exclusive rights to the idea, according to the biography.

Besides, Gates knew full well that Apple took the idea for the graphical interface from the Xerox PARC labs, a research institution they both admired.

The two fought over the graphical user interface. REUTERS/Chip East

When Jobs accused Gates of stealing the idea, he famously answered: “Well, Steve, I think there’s more than one way of looking at it. I think it’s more like we both had this rich neighbor named Xerox and I broke into his house to steal the TV set and found out that you had already stolen it.”

From there, the gloves were off between the two founders.

Jobs and Gates argued over who laid claim to the GUI. Kristy MacDonald/AP

“They just ripped us off completely, because Gates has no shame,” Jobs once said. To which Gates replied: “If he believes that, he really has entered into one of his own reality distortion fields.”

Jobs thought that Gates was a stick-in-the-mud, far too focused on business. “He’d be a broader guy if he had dropped acid once or gone off to an ashram when he was younger.”

They also took digs at each other’s personalities. Justin Sullivan/Getty Images

Gates, meanwhile, said Jobs was “fundamentally odd” and “weirdly flawed as a human being.”

But Gates respected Jobs’ knack for design.

Jobs with an early version of the iPhone. Alessia Pierdomenico / Reuters

“He really never knew much about technology, but he had an amazing instinct for what works,” Gates said of Jobs.

In 1985, Steve Jobs resigned from Apple after a power shift to start his own computer company, NeXT. But even though Jobs was no longer working for Microsoft’s biggest competitor, it didn’t improve relations between the two.

Jobs resigned from Apple in 1985. AP Images

Jobs told Playboy in 1985 that if NeXT lost and Microsoft Windows won, “we are going to enter a computer Dark Ages for about 20 years.”

Still, Windows was winning.

Windows was becoming a dominant force in personal computing. AP Photo

By the late ’80s, it became clear that Microsoft was just about unstoppable on the PC.

Fast-forward to 1996, when Jobs appeared in a PBS documentary called “Triumph of the Nerds” and ripped into Gates and Microsoft, saying that they made “third-rate products.”

Jobs didn’t hold back in “Triumph of the Nerds.” Lou Dematteis/Reuters

Jobs went on in that same documentary: “The only problem with Microsoft is they just have no taste. They have absolutely no taste. And I don’t mean that in a small way, I mean that in a big way, in the sense that they don’t think of original ideas, and they don’t bring much culture into their products.”

By the late ’90s, Apple was in serious danger of going under. When then-Apple CEO Gil Amelio moved to buy NeXT in 1996 and bring Jobs back to Apple, Gates tried to talk him out of it, according to the biography.

Gates reportedly tried to discourage then-Apple CEO Gil Amelio from bringing Jobs back to the company. AP

Gates reportedly said this to Amelio: “I know his technology, it’s nothing but a warmed-over UNIX, and you’ll never be able to make it work on your machines. Don’t you understand that Steve doesn’t know anything about technology? He’s just a super salesman. I can’t believe you’re making such a stupid decision.”

Gates clearly admired Jobs, even if they didn’t always see eye-to-eye.

Some internal emails at Microsoft showed Gates respected Jobs. Mousse Mousse/Reuters

When Apple introduced iTunes, Gates sent an internal email to Microsoft that said, “Steve Jobs’ ability to focus in on a few things that count, get people who get user interface right, and market things as revolutionary are amazing things.”

When Apple introduced the iPod in 2001, Gates sent another email: “I think we need some plan to prove that, even though Jobs has us a bit flat footed again, we can move quick and both match and do stuff better.”

Gates has also said before that he envied that Jobs was a “natural” when it came to commanding an audience.

“It was always fun to watch him rehearse because part of his genius was, when he would finally do it, he would make it look like he’s just thinking it up right there,” he told Dax Shepard on the Armchair Expert podcast. “I’ll never achieve that level.”

“He was such a wizard at over-motivating people — I was a minor wizard so I couldn’t fall under his spells — but I could see him casting the spells, and then I would look at people and see them mesmerized,” Gates continued in the podcast. “I was so jealous.”

But Jobs was still pretty down on Microsoft, especially after Steve Ballmer took over from Bill Gates as CEO in 2000.

Jobs also wasn’t confident in Steve Ballmer’s abilities as Gates’ successor. AP

“They’ve clearly fallen from their dominance. They’ve become mostly irrelevant,” Jobs once said. “I don’t think anything will change at Microsoft as long as Ballmer is running it.”

Conversely, Gates thought much of Apple’s post-iPhone success came from Jobs himself, and not from Apple’s “closed” philosophy.

Gates was also not confident in Apple’s success once Jobs was no longer in charge. Getty Images/Tim Matsui

“The integrated approach works well when Steve is at the helm. But it doesn’t mean it will win many rounds in the future,” Gates said.

They’ve taken swipes at products from each other’s companies.

Jobs and Gates have traded many insults about each other’s products. Getty Images News

Gates didn’t think much of the iPad.

“[I]t’s not like I sit there and feel the same way I did with iPhone where I say, ‘Oh my God, Microsoft didn’t aim high enough,'” he said.

But Jobs didn’t think much of the Windows ecosystem, either: “Of course, his fragmented model worked, but it didn’t make really great products. It produced crappy products.”

Jobs didn’t hold back when Gates decided to quit Microsoft in 2006 to focus more on his foundation.

Jobs has called Gates “unimaginative.” Justin Sullivan/Getty Images

“Bill is basically unimaginative and has never invented anything, which is why I think he’s more comfortable now in philanthropy than technology,” Jobs said, according to the Isaacson biography.

Still, in a weird way, the two men clearly respected each other.

They’ve praised each other in interviews, too, though. The Wall Street Journal

Appearing on stage together at the 2007 AllThingsD conference, Gates said, “I’d give a lot to have Steve’s taste.”

And Jobs once said, “I admire him for the company he built — it’s impressive — and I enjoyed working with him. He’s bright and actually has a good sense of humor.”

After Jobs died, Gates said, “I respect Steve, we got to work together. We spurred each other on, even as competitors. None of [what he said] bothers me at all.”

Ultimately, both men claim quite a legacy: Each built his company into one of the most valuable in the world.

Their companies’ histories are inextricably linked. Mario Tama / Getty

Their competition continues: In recent months, Microsoft and Apple have taken turns leapfrogging each other for the title of the world’s most valuable publicly traded company.

Matt Weinberger contributed to an earlier version of this story.

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