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.’

There have been numerous occasions since when I wished I’d stuck to my guns. Turns out, I was right and Graydon was wrong and we wouldn’t have had to search very far to find examples of the phenomenon I was talking about. In 2004 it emerged that Annie Leibovitz, Vanity Fair’s in-house photographer, was underwater to the tune of $24 million. I daresay half the staff were flat broke, desperately trying to keep up appearances while their creditors circled.

L’Wren Scott, Mick Jagger’s girl-friend, is a case in point. After she committed suicide last week, it emerged that her fashion business was £6 million in debt. Not that you would have known it to hear her talk. ‘I always say luxury is a state of mind,’ she told the Sunday Times last November. ‘Because for me, it really is. It’s legroom, it’s a beautiful view, it’s great food at a great restaurant you’ve discovered because you obsessively read Zagat, as I do.