This clips is from my interview with Chris MacAskill, who worked for Steve Jobs at NeXT Computer. Today, Chris is the co-founder of SmugMug, a family-owned photo sharing site that makes pictures look incredible.

Transcript below. (And you should hear the full interview.)

The story:

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The transcript:

Andrew: How about the Canon story? How did [Steve Jobs] sell Canon on investing in his business?

Chris: I’m not sure he’d appreciate me telling this. I wasn’t as close to Canon as some of the other stories, but I do remember that he put on quite a show and started crying in front of the Canon guy.

When Canon wanted to put up some much lower number than Steve hoped for — and I thought the number was pretty big, something like $25 million. I don’t remember exactly.

But he started crying. I think he would have been an A-list actor if he could have been. Whether it’s genuine or not, I don’t know. I suspect it was part of Steve’s act, but he does it all so very well.

Anyway, he came up with this $100 million. I could give you a few other ones that he did that were just phenomenal.

Andrew: I’d love it, but I’ve got to ask you this crying. Usually, if there’s crying in business, people lose respect, the crier lose respect. How did he do it in a way that got him the deal instead of getting him laughed at?

Chris: I’ve heard it told that it was a manner of losing face for the Japanese. This guy was sent to do this deal and he’s got the CEO breaking down, one of the great ones of the industry, who’s larger than life, who founded Apple and so on. He’s got him breaking down, and there’s a lot of face lost there, so that’s how he did it.

Continue to the full interview >>