Ultimately, both men claim quite a legacy: Jobs built Apple into what is now the most valuable company in the world, while Gates is the world's richest man.
The two actually reconciled close to the end of Jobs' life, with Gates becoming a personal friend of the Apple founder. 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."
Source: New York Post
And Jobs once said of Gates: "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."
Source: "Steve Jobs" by Walter Isaacson.
Still, in a weird way, the two men clearly respected each other. Appearing on stage together at a 2007 conference, Gates said, "I’d give a lot to have Steve’s taste."
You can watch them together here.
Jobs still didn't have any mercy when Gates decided to quit Microsoft in 2006 to focus more on his foundation. "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.
Source: "Steve Jobs" by Walter Isaacson.
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."
Source: "Steve Jobs" by Walter Isaacson.
And Gates didn't think too 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.'"
Source: CBS.
Conversely, Gates thought much of Apple's post-iPhone success came from Jobs himself, and not from Apple's "closed" philosophy. "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.
Source: "Steve Jobs" by Walter Isaacson.
But Jobs was still pretty down on Microsoft, especially after Steve Ballmer took over from Bill Gates as CEO in 2000. "They've clearly fallen from their dominance," Jobs said. "They’ve become mostly irrelevant ... I don’t think anything will change at Microsoft as long as Ballmer is running it."
Source: "Steve Jobs" by Walter Isaacson.
But in that same e-mail, he called for Microsoft to go on the offensive: "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."
Source: Gizmodo.
Gates clearly admired Jobs, even if they didn't always see eye to eye. When Apple introduced iTunes in 2003, Gates sent an internal email to his employees saying, "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."
Source: Gizmodo.
By 1997, Jobs became Apple CEO, and had to get over his distaste for Microsoft to make sure the company survived. At his first Macworld keynote, with Bill Gates appearing behind him on a huge screen via satellite uplink, he announced Apple had accepted an investment from Microsoft. The audience booed. Jobs later said he regretted allowing Gates' huge head to loom over him on stage.
Source: "Steve Jobs" by Walter Isaacson.
Gates 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 ... He doesn’t know anything about engineering, and 99% of what he says and thinks is wrong. What the hell are you buying that garbage for?"
Source: "Steve Jobs" by Walter Isaacson.
By the late '90s, Apple was in serious danger of bankruptcy. 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.
Source: "Steve Jobs" by Walter Isaacson.
Jobs continued, in the 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."
You can watch the documentary here.
Fast forward to 1996. Jobs appeared in a PBS documentary called "Triumph of the Nerds" and ripped into Gates and Microsoft, saying that they make "third-rate products."
You can read a transcript of the documentary here.
But Windows was already winning the war. By the late '80s, it became clear that Microsoft was just about unstoppable on the PC.
If NeXT lost and Microsoft Windows won, Jobs thought "we are going to enter a computer Dark Ages for about twenty years."
Source: "Steve Jobs: The Journey is the Reward" by Jeffrey S. Young.
In 1985, Steve Jobs resigned from Apple to start another computer company, NeXT. But even though Jobs was no longer working for Microsoft's biggest competitor, relations between the two didn't improve.
Source: "Steve Jobs" by Walter Isaacson.
Gates respected Jobs' knack for design: "He really never knew much about technology, but he had an amazing instinct for what works."
Source: "Steve Jobs" by Walter Isaacson.
Gates thought Jobs was "fundamentally odd" and "weirdly flawed as a human being."
Source: "Steve Jobs" by Walter Isaacson.
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."
Source: The New York Times.
To which Gates replied: "If he believes that, he really has entered into one of his own reality distortion fields."
Source: "The Innovators" by Walter Isaacson.
From there, the gloves were off between the two founders. "They just ripped us off completely, because Gates has no shame," Jobs once said.
Source: "The Innovators" by Walter Isaacson.
Besides, Gates knew full well that the Macintosh's graphical interface was inspired by one developed by Xerox's Palo Alto Research Center, an institution they both admired. 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.”
This is a story told by early Apple engineer Andy Hertzfeld.
A furious Jobs accused Gates and Microsoft of ripping off the Macintosh. But Gates didn't care — he knew graphical interfaces would be big and didn't think Apple had the exclusive rights to the idea.
Source: "Steve Jobs" by Walter Isaacson.
Their relationship, already kind of rocky, fell apart when Microsoft announced the first version of Windows in 1985.
Source: "Steve Jobs" by Walter Isaacson.
For the first few years after the Macintosh's launch, Microsoft and Apple worked closely together. At one point, Gates quipped that he had more people working on the Mac than Jobs did.
Source: Computerworld.
Still, Gates appeared alongside Jobs in a 1983 video — a "Dating Game" riff — screened for Apple employees ahead of the Macintosh's launch. In that video, Gates compliments the Mac, saying it "really captures people's imagination."
You can watch a clip here.
Gates wasn't particularly impressed with what he saw as a limited platform — or Jobs' attitude. “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 said later.
Source: Fortune.