The Mobile Wave
Saylor includes his own book with stated hesitation, for one reason: it is an applied exercise in reasoning from first principles. Written in 2012, it asked what would follow when computing went mobile, software dematerialised products and services, and billions of people gained continuous access to networked intelligence. The wider lesson: digital transformation rarely leaves an institution intact and merely faster. It usually dematerialises the institution, redistributes power, changes the economics, and produces something structurally different.
Read it as an auditable forecast, not an authority. Ask which predictions held, which were incomplete, which second-order effects were missed, and which analytical methods proved useful. Judge it against the world that actually followed.