McLuhan had some ideas that stood the test of time, but his writing was always a bit of a joke. This article quotes a paragraph that brings back memories of youthful days spent trying to figure out just what he was going on about. Like much of the art of the era, McLuhan's writing had the appeal of being different and even a bit wild. Readers felt cool, swimming in hippy-dippy confusion without having to drop acid.
Reading McLuhan has had definite returns for me. The most bang for the buck is _Understanding_Media_.
People complain about its difficulty, its seriousness, etc. It's not that hard. He does use a few jargon terms, like "hot" and "cold." And their meanings do change, but don't forget, the media have changed.
For example, Web 2.0 and search engines shifted the web medium to hot, from cold.
In cool media, you have to fill in details yourself and "run it" yourself. It's there with you in the same room, but it's not actively seizing your attention. In hot media, every square inch and second is filled in.
I will say, though, that sometimes his writing reveals too much. When you realize just how utterly different our world is now from the pre-print-era, it can be overwhelming. Most of us are just barely clinging to a piece of stability in its whirlpool, but if we step off that platform for a moment and observe the complexity of the world, we realize just how much we depend on our complex media.
Step off the main drag in a foreign country and you'll see just how isolated and disconnected we are from everything else.
Anyway, I'm still not sure just how McLuhan relates to start-ups at this time... I'd have to ponder it more, but for example, we can see that the superfluidity of web media is shaking up ways of doing business and breaking up some of the large companies and creating more temporary work and less pensioned and union-protected work. The unions and pensions were dependent on stable media. It will be some years, 10-20, before current media are stable enough.
If you like McLuhan you'll love Castells, the world's top communications scholar today. His stuff is hugely relevant to the internet society. Start with Communication Power.