Lessons from Tina Brown on the art of failing upwards

Shortly after I started working at Vanity Fair in the mid-1990s, I suggested to my boss Graydon Carter that I write an article about the number of New York society types who were bankrupt. Not morally bankrupt, but up to their eyeballs in debt. ‘Let’s get a team of researchers to go through the financials of everyone on the guest list of the annual costume ball at the Met,’ I suggested. ‘We could publish a list, like the Forbes 400, but the exact opposite: America’s most indebted billionaires.’

Graydon didn’t go for it, and not just because he was worried about its impact on his social life. ‘Like who?’ he said. I rattled off a list of names, but he pooh-poohed every one. ‘This is just wishful thinking, Toby,’ he said. ‘The truth is, they are all rich. Much richer than you or I will ever be.’

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