Steve Jobs first approached Dell back when he founded NeXT back in 1985, where he wanted Dell to partner with his new company and run the NeXT operating system on Dell PCs.
At the time, the former Apple CEO said that the NeXT operating system was superior to Windows, but Dell founder and current CEO Michael Dell said he told Jobs at the time that it just wasn't going to happen because there was no software for it and "zero customer interest".
Dell talked about Jobs in his new book "Play Nice But Win" where Dell talks about how as a teenager, he was in love with the Apple II. He talks about meeting Jobs and how he asked Dell to license the Mac operating system and use it on Intel-based Dell PCs. In the end, Dell and Apple became competitors and both have enjoyed meteoric rises over the last couple of decades since Jobs asked Dell to put Mac OS on Dell systems powered with Intel processors.
"He said, look at this - we've got this Dell desktop and it's running Mac OS. Why don't you license the Mac OS?"
Dell smiles when he tells the story, adding: "The royalty he was talking about would amount to hundreds of millions of dollars, and the math just didn't work, because most of our customers, especially larger business customers, didn't really want the Mac operating system," he writes. "Steve's proposal would have been interesting if it was just us saying, "OK, we'll pay you every time we use the Mac OS" - but to pay him for every time we didn't use it ... well, nice try, Steve!"
You can read more about Dell and Jobs in this story here.