Anna Wintour

Context matters here.

Madonna in 1989 had just released Like a Prayer, Burning Cross's romantic scenes with a black saint.

Pepsi pulled her sponsorship.

Religious groups wanted boycotts.

She represented everything Vogue readers theoretically rejected.

Anna put her on the May cover.

You need to be culturally relevant, important, and controversial from time to time, she later explained.

The numbers told the story.

200,000 more copies sold than previous May.

But that's not the lesson.

The real lesson is about information asymmetry.

When everyone knows something would never work, they stop testing it.

That creates an opportunity.

Within five years, every fashion magazine featured celebrities.

Anna didn't predict the future, she created it by doing what nobody else would test.

Sometimes the best strategy isn't finding what people want, it's showing them what they didn't know they were allowed to want.

The early 1990s belonged to supermodels, Naomi Campbell, Kate Moss.

They commanded massive fees and magazine covers.

Anna killed them off.

It wasn't personal, it was business.