The Art of the Parlay: John Gruber shows once again why he’s worth every penny of the “Daring Fireball” membership fee. (Having said that, where’s my blasted T-shirt, hey?)

In this long article, he argues that the Macintosh’s marginal market share was not because Apple refused to licence the OS to other computer manufacturers, but rather because Apple didn’t provide an upgrade path for its enormous Apple II user base — in other words, Apple didn’t leverage its existing marketshare but instead essentially started from scratch. To move to the Mac, Apple II users had to leave all their hardware, peripherals and software behind — whereas MS-DOS users were able to migrate to Windows “slowly and incrementally.” Had Apple done otherwise, Gruber argues, the Mac might have been more successful in a marketshare sense, but less revolutionary. (Imagine if there had been a successor to the Apple IIgs.)

Now, Gruber’s article struck a chord with me because it echoes my family’s experience. In the mid-1980s we each had an Apple II+ or a IIe. By the late 1980s we each had an Apple IIgs. By the early 1990s we each had a 386- or 486-class PC. What happened? Without a post-IIgs upgrade path, switching to a PC was no more onerous than switching to a Mac, and it was less expensive. I imagine that a lot of Apple’s customers were lost this way. In the end, my father and his brothers were pissed at Apple for killing the Apple II line, and when you talk to them about it today, they’re still mad at them for it. There is a reason why I’m the only Mac user in my family!