On a much larger scale and with images SnapChat does the same.

It's an image chat app that is apparently very popular with youngsters and is euphemistically called the Sexting app.

There is doubtfully a crypto component to it besides ssl. But images autoexpire quickly. You can still take screenshots though, which is the main problem with it.

I followed the OODA link to wikipedia to read up to its tenets, ending up in a presentation by J.R. Boyd himself: http://www.dnipogo.org/boyd/organic_design.pdf

At the third slide he states why security in c&c (army that is) is necessary: to remain unpredictable.

I find that goal hard to reconcile with "security" goals in civil society, where continuity, reliability and predictability are considered to be important virtues, at least for businesses.

The adversary perspective may be exists between competing businesses, but not between a business an its patronage. There the aforementioned virtues are paramount for success.