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What he’s missing is that the cable companies buy their channels in bundles too. They don’t get just ESPN, they get the whole ESPN package (2, News, Deportes, Classic, U) plus Disney and ABC Family all at a “cut rate”. This is why they sell in bundles, it’s all wrapped up in the contracts they’re getting from the channel companies. Until the cable companies can buy ala carte (which the channels won’t do because it’s he best way to push their cheap channels that are all profit even with few viewers) they will be contractually unable to sell ala carte.

I'm not sure where you got your information but it is not entirely accurate, and no I don't work for a cable company. I work for an integrator and our job is to update cable company headends and telco central offices.
Lets take ESPN/Disney for example. Not only do operators have to pay for each channel individually, they also have to carry second tier channels they don't want AND have pay for those also. That's why there are so many channels no one cares about.
OK, Comcast, Charter, Time Warner, etc decide $4.08 is too much for ESPN and refuse to pay. Disney doesn't budge so the operator drops ESPN from the line-up. It would take a grand total of 5 minutes for their CSR’s to be overwhelmed with angry customers. The programmers know this so they just wait the operators out.
But don't fret. If your patient enough you'll start seeing voice, video, and data sold in blocks of usage instead of the current “broadcast” package. For instance, 40 hours of on-demand video product (TV series, movies, sports), 40 hours of Internet access plus unlimited voice for $X. As soon as the competition between switched digital video and IPTV plays out (IPTV will eventually win) I think something similar to what I described will take place.