He's not totally wrong
I think the point he's making (though maybe doesn't really want to admit) is that the younger generation expects and is used to so much less they'll see no problem dropping their services there. After all, Facebook, Twiiter, Google, MS, etc. have outages all the time and it's no big deal. Just invent some cute corporate equivalent of the "fail whale" and you're good to go.
He is right about one thing. When those of who keep hitting management over the head with the reliability and security arguments are gone, and there are no throttling voices left to remind the beancounters about enterprise risk, this stuff will all move to the cloud. And you know what? If everyone does it and failures are common for everyone, will it matter?
I am the guy he's talking about, and the reputation I've built over the last 35 years protecting the enterprise is still worth something today. Ten years from now, who knows? Luckily for Rackspace, I'll be out of the way by then.