When reading about the life of Steve Jobs, my favorite moments are those when I get to see him enjoying his work. A fascinating new book by Ken Segall, who worked with Jobs for seventeen years at NeXT and Apple, shares one such moment that I hadn’t heard of before:

At one of our regular agency meetings, about a year after the launch of iMac, Steve walked into the room giddy with enthusiasm for a new idea. . . . On this day he was pitching an idea to the rest of the room rather than the other way around.

According to Apple’s calculations, the one millionth iMac was about to be sold. That was huge news. Remember, Apple had undergone some tough times, and iMac was the first new computer to be launched by Steve upon his return to the company. To have sold a million iMacs in a relatively short time was proof that something very right was happening, and it deserved some serious fanfare.

Steve’s idea was to do a Willy Wonka routine with it. Just as Wonka does in the movie, Steve wanted to put a golden certificate representing the millionth iMac inside the box of one iMac, and publicize this fact. Whoever opened the lucky iMac box would be refunded the purchase price and then be flown to Cupertino, where he or she (and, presumably, the accompanying family) would be taken on a tour of the Apple campus.

Steve had already instructed his internal creative group to design a prototype golden certificate, which he shared with us. But the killer was that Steve wanted to go all out on this. He wanted to meet the lucky winner in full Willy Wonka garb. Yes, complete with top hat and tails.

It was one of those ideas that everyone in the room chuckled about, maybe more so because Steve seemed to be so enamored by it. He saw the potential to get massive PR for iMac and Apple, and he was more than willing to do his share by donning the costume. Unlike what happened in the movie, however, the winner would not become the new owner of Apple. He or she wouldn’t even get a junior assistant CEO position. It would all be for fun—along with the big, juicy headlines.

That made me smile when I first read it. It still does.

Why is this the first time you’ve heard about it? Surely it would have made the news, and the image of the one-millionth iMac buyer standing in awe next to Jobs in full Willy Wonka garb would have become a popular sign of the times. What happened to this wonderful idea?

Unfortunately, Apple couldn’t proceed with it, because the legal issues were too restrictive.

For one, California regulations required that this be classified as a sweepstakes, which meant that there had to be a “no purchase required” provision. It would be impossible to make that golden certificate work under these rules, so it would be more of a drawing. Which meant anyone off the street could win, and the odds were that whoever did win probably wouldn’t even have purchased an iMac. Faced with the restrictions imposed by lawyers, Steve decided it wasn’t worth it.

Such is the state of the regulatory nightmare in America today. Even something as simple and benevolent as a certificate for purchasing the one millionth iMac can’t be implemented without permission and mountains of red tape.

I expect Jobs let loose a torrent of expletives. He certainly had good reason to.

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