No. Not in the sad my-life-adds-up-to-nothing way, but more in the case study sense. I've been noticing how often optimistic analyses of proposed products and business models echo the same arguments used over the years for various underperforming enterprises and catastrophic failures, invariably without a flicker of recognition.
No doubt, this is partly due to a general lack of long-term memory in the pundit class, but the problem seem particularly acute when it comes to failure. There are exceptions like this well-thought-out analogy by Josh Marshall or this piece of historical context for Zucker's Leno debacle from Kliph Nesteroff, but as a rule, most journalists don't pay nearly enough attention to these counterexamples (which makes it all the more difficult to avoid repeating mistakes).
I'll try to add some more entries and drill down into some of the specifics, but in the meantime, here's a short list of some potentially useful examples ideas that seemed (and in some cases, actually were) good ideas at the time.
The aforementioned mentioned attempt to make Jerry Lewis king of the talk shows.
A late Eighties format that doubled the resolution of video tapes while being completely compatible with standard VHS.
An attempt to break the Seventies DC/Marvel duopoly.
An attempt to break the Coke/Pepsi duopoly (perhaps breaking duopolies deserves a subcategory).