I don’t want to represent that I have a comprehensive understanding of the history of business, but I can say that in my lifetime, the single greatest corporate failure was America Online not following AOL Instant Messenger to its obvious conclusion.

AIM was the place where an entire generation, the first generation of Digital Natives™ (with experience of the prior world of rotary payphones), connected with one another online, and AOL got nothing from it. The failure is truly astounding.

AIM was where all kids lucky enough to have computers lived, particularly during those awkward sit-on-the-phone-for-hours-sometimes-in-silence-with-boys/girls years. AIM let us conduct multiple conversations with boys/girls simultaneously.

So addicted were most of us to AOL Instant Messenger that, when there was no one around, we would look at each other’s AWAY MESSAGES. These could be styled in different colors.

An entire generation of, the FIRST generation, of web citizens, spent hours curating AWAY MESSAGES.


All these kids were screaming, in bRiGht, cOlorFUL, aLteRnATe CAPS, for a Facebook timeline, for a place to post. AOL had them all!

It’s no wonder they became the first company to fail at trying to own the Internet.

To run AOL Instant Messenger the way it ran in the late 90s is leaving a trillion dollars (actual approximate number) in cash sitting in your car (and not even locking the door because you don’t want to have to fish the key out, yes we unlocked car doors with a key back then).

You can tell me if you think you’ve seen a bigger, more obvious miss. A more catastrophic result of business incompetence. A more spectacular wildfire of hundred dollar bills just from pure negligent oblivion.

I have never seen one. AOL’s failure is truly astonishing.