I remember in the 1980s Branson flew almost entirely across the Atlantic by balloon only to crash off the coast of Ireland. Plus the powerboats, Breitling Orbiter and most bravely I think: appearing in drag to promote his wedding business.
Even he now admits that "Virgin Brides" (actual name) wasn't his strongest idea :-D
It sounds like he thought it would be funny, and was willing to throw a few million dollars at trolling. Not hard for somebody who can throw more tens of millions at a joyride in a rocket.
At the other end of the spectrum is the anxiety about what other people think and say about us and how well we will do when faced with a challenge or change we brought on ourselves, especially when we really stick our necks out on something completely new.
HN is full of people who are maestras and maestros of technology who are sticking their necks out in the capricious people-centric world of business. It’s a site built for entrepreneurs even if the majority of us visitors (myself included) are tech janitors.
And in terms of the transformation the most surprising part, I think, wasn’t the dress. It was the lipstick.