Consider that he'd already moved to Sri Lanka in the 1950s, ostensibly out of his love for diving. He was primed to see the benefits of WFH and telecommunication, and certainly able to exploit the flexibility in his own life and career.

Ironically, with his adventurism and individualism, perhaps his imagination was too limited to think that many people are self-limiting. The companies you speak of are not abstract entities forcing the poor humans to live unwanted lives. They are the people---identifying with the rituals of office life and demanding conformance from one another.