Getting There: A Book of Mentors (2015)
VANITY FAIR EDITOR
I grew up in the suburbs of Ottawa, a model of Post-Edwardian protestant probity and the capital of Canada. I was interested in becoming a playwright or an editor, but I had no role models. Ottawa was a government town and most of the adults I came into contact with were either diplomats or civil servants. My parents were warm and loving, but they provided little in the way of career guidance. Their complete inattention to me and my brother and sister might have proved a blessing.
I’ve come to realize that having all the space and freedom they afforded me was actually a huge gift. A lot of kids today are overloaded with after-school and weekend lessons—piano or Mandarin Chinese, things like that. I do believe that one of the most important things you can do for your children is to not overschedule them. Children need time to be bored and daydream; it’s an important part of life. My daydreams motivated me and shaped my future.
Since I knew I’d eventually wind up with a white-collar job, I had a strong desire to taste life first—so I took on a number of blue-collar jobs when I was younger. In high school I worked for two weeks as a grave digger. When the weather turned cold in Canada, the ground would harden and so our local cemetery stockpiled the incoming beginning in October. When things began to thaw in the spring, they took on high school kids to help dig graves. I also sorted mail at the post office during Christmas breaks. One summer I worked in a bank and the next I stocked shelves in a big department store. For most of my high school summers I worked as a camp counselor and in the winters I was a ski instructor. I took a year off during college and worked for much of it as a lineman out in the Western Canadian prairies for the Canadian National Railroad. That was one of the most formative experiences of my life. I lived with twenty other men in a box car that had been outfitted as a bunkhouse. Most of the others had criminal records for minor nonviolent crimes such as grand theft auto. They were a colorful crew. I got along with all of them, though. I was a good listener and learned to take my time fitting in. I made strong friendships, and by the time I came home, I realized that I could talk to just about anybody about anything. I read constantly and loved being out in the wild surrounded by rough men with difficult pasts. I went into the job with a great fear of heights, and by the end, like the others, I could climb a forty-foot telegraph pole without a safety belt. The workday was long and brutally hard, but I don’t think I’ve ever loved a job so much. Also, I came back really fit.
I attended the University of Ottawa and Carleton University, but was eventually thrown out of both, due mainly to a general lack of attendance.
During my first year at the University of Ottawa, I ran into a clever, energetic fellow named Graham Pomeroy who taught me a great deal about turning an idea into a reality. He was starting a literary magazine called the Canadian Review and I signed on as his junior partner. My visions of the outside world were largely defined by magazines—Time, Life, Esquire, Harper’s, the New Yorker, and the like. I loved magazines back then—and I still do. So I had the passion to jump into a new start-up but had absolutely no idea what to do. This was the early 1970s, before the Internet, fax machines, and computers. Many magazines were still set in hot type back then. I learned as I went along and grew to love every aspect of it all. At first, the publication was scholarly and, truthfully, not much fun to read—but we slowly built it into a sophomore version of Harper’s, a magazine I admired. After a couple of years, Graham left and I became the sole editor. I poured everything I had into that magazine, working twelve to fifteen hours a day every day. I never took vacations and never went to class. I didn’t have the time. I knew in the back of my mind that working on the magazine was going to prove to be the most worthwhile use of my time.
Some of my professors wrote for the Canadian Review. They were certainly not happy about my habit of skipping class, but they let me hang in there for a couple of years. At a certain point, the point at which I had too many incompletes to ever graduate, the school basically said, “You cannot graduate from here so there is no point in staying.” I moved across town to Carleton University, where pretty much the same thing happened. The magazine took up most of my time, I never went to class, and after about a year and a half, I was asked to leave there as well.
Despite the fact that the Canadian Review had become quite popular, it did nothing but lose money. After giving it my all for five years, I sold our subscription list and assets to Saturday Night magazine, a competitor and a far superior publication. There is nothing worse than a long-term business failure. You pretty much know what’s going to happen long before it goes under, and that whole period (about a year and a half in my case) was wretchedly painful. But, at the same time, I did it in concert with two wonderfully funny and supportive colleagues, Kate White and John Watts, and I now look back on the entire experience, even the darker moments, with great fondness.
My Canadian Review failure taught me an important but simple lesson: To succeed, your business has to have a point. I don’t care what kind of a business it is; it has to provide something that others don’t, and it has to do it well. The Canadian Review didn’t have a point. It existed in large part because I wanted to have a magazine, and to the people who were our purported market that wasn’t enough. Publications that are only there because the person behind them wants them to be rarely do well. Of course, some things that have a point fail too, but I have tried to make sure that everything I’ve done since then has a purpose.
After the Canadian Review shut down, I came to New York. I was encumbered by my student loan, but I had enough cash to enroll in an editing and publishing program at Sarah Lawrence College. When that ended, I returned home to Canada with the intention of moving to New York. I didn’t have much money, just about $500 in cash and a credit card, but I figured that was probably enough to squeak out a month there looking for work. I wrote to everyone I had met through the Sarah Lawrence program (mainly magazine editors) and got appointments with most of them. I had never written a proper magazine article per se, but just as my money was running out, I was hired as a writer in the business section of Time. The Prince George Hotel on East Twenty-eighth Street had a special student rate of twenty-two dollars a night, so I moved there. I would leave in the morning dressed like a student then change into a suit when I got to the office. I’d change back into my student clothes before returning to the hotel. The twenty-two dollars was due every day. In cash.
Although I made some wonderful friends at Time, I had serious difficulties there and was in no way what you would call star material. In part, this was due to my own sweeping inadequacies. But it was also about the talent I was competing with. It was humbling to be surrounded by the extraordinary stable of young writers then working at the magazine: Michiko Kakutani, Frank Rich, Kurt Andersen, Walter Isaacson, Evan Thomas, Maureen Dowd, Alessandra Stanley, Jim Kelly, Steve Smith, Tom Sancton, and James Atlas. The list is long. All of them have gone on to have very distinguished careers.
At one point, Marshall Loeb, Time’s business editor, called me into his office and said, “Look, everyone really likes you, and you’re a wonderful person, but you’ll never make it in the magazine business. Maybe you should think about going into ad sales?” That was a low point. Still, I kept at it, working on my writing. (Fear of failure has always been a big motivating factor. I only got my American citizenship in 1999, so for most of my career, losing my job also meant the potential loss of my H-1B work visa, which would mean returning to Canada a failure.) My writing got better, but in the end I wasn’t Time material, and after five years I left.
It was while I was at Time that my colleague and friend Kurt Andersen and I began talking about starting our own magazine: a satirical monthly about New York. By the time we began making more formal plans, I had moved to Life magazine, a few floors away in the Time & Life Building. I had the title, Spy, and over many lunches, we formulated a rough idea of what the magazine would be about. We teamed up with a young banker from Goldman Sachs named Tom Phillips, raised money, and took office space in the Puck Building on Lafayette Street. Spy proved to be successful and highly influential. If there is more fun to be had in the magazine business, I would be surprised. A stand-alone magazine in a conglomerate age is a tough place to be, though. And we were constantly short of money. At one point it just ran out, and we sold the magazine after five years to the adman Charles Saatchi and the investor Jean Pigozzi.
At that point I began thinking about starting up a biweekly New York newspaper and went on a listening tour to figure out how to accomplish this. I bumped into a man named Arthur Carter who owned the New York Observer, which was, at that time, a sleepy backwater broadsheet printed on salmon-colored paper. It had little in the way of audience or influence. Arthur hired me to redo the paper. I formulated six-month, twelve-month, and eighteen-month plans and set to work. Within three or four months, people were beginning to read it. At the ten-month mark, it had reached some sort of critical mass and a lot of people I knew seemed to be reading it. I began sending complimentary copies to about one hundred people every week, including a number of overseas Condé Nast editors I knew. Si Newhouse, whose family owns Condé Nast, took a trip to Europe twice a year to visit many of his international properties. Everywhere he went he spotted a copy of the New York Observer on somebody’s desk. Not realizing that they were getting it for free (and probably not even reading it), he came back and asked if I’d like to meet with him. In 1992 Si hired me to be the editor of Vanity Fair, and I’ve been there ever since.
The first two years were, to put it mildly, rocky. Most of the advertisers and the staff looked on me with suspicion, and how could they not, given what we had written about many of them at Spy. The atmosphere was so poisonous that I didn’t like to bring my kids into the office. But I’m a decent person, and since I treated the staff with respect, it gradually got better, and then it got truly wonderful.
Si has been like a father to me. A true role model. He has a Socratic method of sorting through problems that has been invaluable. And his wisdom covers you like a blanket. There is no finer man to work for. And after owning two magazines, it’s a relief to have the financial aspects of a magazine in somebody else’s hands. It frees you up to do what editors do best: edit.
Nobody knows what they’re doing at first. You have to find something you are interested in, throw yourself at it, do the best you can, and pick things up as you go along. I never saw myself as having a career path. I’ve sort of muddled through from one thing to the next and, for most people, that’s just the way careers evolve.
You learn a lot more from mistakes than you do from successes. I tell my kids, “It’s almost certain that you are going to make mistakes along the way. Try to make small ones, if you can, and think of them as opportunities to learn.”
Even though I never ended up graduating from college, I think it’s important for young people to try to do so. It was less difficult to get by without a completed education back when I was in my twenties. Rent was cheaper then and it was easier to live.