The "older doofuses who didn’t understand the Web" seemed to have done pretty well with CollegeHumor and Vimeo without Jake. If they had run them into the ground, I imagine he'd write an article about how being acquired is always success.
The existing businesses were nurtured and optimized reasonably well. I was lamenting the loss of the creative spirit that generated those two businesses in the first place -- the larger, more valuable core of the company.
I kid because the title seems designed to be provocative. It's not always failure to sell out. Quite the opposite in my case, but I hear you. You "sold out" and lost something in the process. They have been good stewards of Vimeo. It's one of the quality sites on the web, so I wouldn't fret too much. You created something wonderful. That's more than most people.