Why Bill Gates says he was ‘so jealous’ of Steve Jobs

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Microsoft should have been Apple's biggest mobile challenger, Bill Gates says.
Gates says that, unlike Jobs, he wouldn't have been able to turn Apple around in the late 90s.
Photo: Statsministerens kontor/Flickr CC

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.”

Reflecting on Jobs’ turnaround of Apple in the late 1990s, Gates opined that: “No one else can do what he did there. I couldn’t have done that [and] I don’t know anyone who could have.” He called Jobs’ return “truly phenomenal.”

You can listen to the Armchair Expert episode in question here. This isn’t the only Apple-centric topic Gates discusses during the podcast. He also chimes in on the current investigations of tech giants by Congress. (Microsoft was famously the target of an antitrust case in 2001 that arguably slightly dislodged the company’s iron grip on the tech world.)

“If you are as successful as I am, or any of those people you are, you deserve rude, unfair, tough questions,” Gates said. “The government deserves to have shots at you. That type of grilling comes with the super-successful territory, it’s fine.”

Steve Jobs’ relationship with Bill Gates

Gates’ relationship with Steve Jobs — which has been the subject of plenty of books, documentaries and even the great movie Pirates of Silicon Valley — has always fascinated me. People tend to think of Jobs and Gates as rival bosses of tech giants. In fact, it’s a bit more complex than that.

Gates actually started out as a Mac developer. In fact, he was considered so valuable by Apple that Cupertino signed a terrible exclusivity deal with him that ultimately helped lay the groundwork for Windows. Gates actually recommended that Apple license out its Mac OS, which was the same strategy Microsoft ultimately used to conquer the tech world.

In the late 1990s, Gates’ Microsoft invested $150 million in Apple which, depending on who is telling the story, either helped save the company or was done to settle a QuickTime lawsuit (maybe both at once.)

Gates thinks Jobs was “magic”

Gates, particularly since he left Microsoft to focus on his philanthropy efforts, has been complimentary of Jobs. The Armchair Expert podcast also isn’t the first time he has used a magic metaphor to describe Jobs.

The most fascinating public meeting between Gates and Jobs was at a D5 conference in 2007 when both were interviewed together onstage. At one point, Gates said he would “give a lot to have Steve’s taste.” He said that, in their years working together, Gates would “see Steve make [decisions] based on a sense of people and product that … is hard for me to explain. The ways he does things is just different and I think it’s magical.”