Timing is everything, right?

Facebook’s purchase of WhatsApp for $19 billion had a familiar ring to me, like I’ve seen this movie before. Then I realized why when I saw former AOL executive Ted Leonsis’s post on his Revolutionary Views blog.

Back in the day, during the go-go dot-com era, America Online was eagerly snapping up whatever the kids wanted, whether it was the early digital music player Winamp or the instant messaging service ICQ.

There was a time when the only way I could call my boys to dinner was to IM them, this was before “texting” really entered the vocabulary. Instant messaging was B-I-G, just like AOL’s MapQuest service seemed to own the monopoly on helping you get from here to there.

The suite of products was all part of a “walled garden” strategy to make you never want to leave AOL’s land of digital delights.

Except it never quite worked. Some blamed execution, but the truth is a lot of these innovations were early, before we knew what an Internet cloud was or that a phone could be smart.

Perhaps the passage of time, and the evolution of technology, means Facebook is not doomed to repeat history. Maybe scale matters.

Listen to Leonsis:

“Same stuff, just bigger, as the number of people online today measures at about 2.5 billion, with only 250 million or so connections being U.S.-based. Global is the game now. When I first got online, there were about 1 million people connected online around the globe. When I joined AOL, we were on a March To A Million Members. We topped out at 36 million paying subscribers.

“Time will tell whether this was a smart acquisition by Facebook. When AOL had created great value, communications à la mail and messaging and chat were core and central to its members, so I understand the rationale.

“Who knew that the ‘Walled Garden’ and platform strategy of yesterday would end up relevant and worth more than $100 billion today?”