I think they're making a more specific, snide point about how Microsoft employees would watch IBM become less and less relevant for general consumers and think on some level that they were less vulnerable to the same fate.

In general, I'm sure you're right. Even today, IBM and Bell Labs still represent the majority of the private side of innovation in computing history.

It wouldn't surprise me that Bill Gates admired the IBM of the 50's through 70's. They dominated the computer industry and did lots of amazing things.

The IBM the earned such derision from Microsoft was the IBM of the mid-80s and 90s. IBM steadily lost it dominance in computers (mainframes) to smaller computers (minicomputers and microcomputers). It seemed to be so mired in bureaucracy and their successful past that they couldn't do anything about it.

Microsoft of 2012 looks similar to IBM of 1982: their monopoly in computers (PCs) is threatened by smaller computers (smart phones and tablets). They are desperately trying to stay relevant, but are still stuck in their successful past (Windows) and can't abandon it. So as Mr. Hill said, it looks like they've become the thing that they hated so much.