How I put myself through school by writing to two of the richest men in Canada

MAGGIE GILMOUR November 24 2008


How I put myself through school by writing to two of the richest men in Canada

MAGGIE GILMOUR November 24 2008


How I put myself through school by writing to two of the richest men in Canada


In September 2005, I left Toronto for grad school in Berkeley. In my bags, along with a copy of Joan Didion’s Slouching Towards Bethlehem and several pairs of regulation California flip-flops, I had two cheques totalling $26,000. The cheques were from Canadian millionaires I’d never met. They’d promised to send me money to pay for grad school, provided I write to them

once a month. They also asked me to keep the arrangement confidential.

I kept half of my promise.

What follows is the story of how one girl (me) put herself through school by writing to two of the richest men in Canada.

April 2005.1 was at my friend Rachel’s house, sitting at her kitchen table with Shuah, her lovely bespectacled friend. It was a spring day in Toronto.

I needed money. Not for an abortion or a car or anything ghastly like that. I’d just applied to one of America’s most expensive graduate schools and had gotten in. They

were offering me $5,000 in scholarships, which would cover the cost of coffee and sunscreen for a few months. I needed more, and I needed it fast.

“Who has money?” I asked, into the air.

Rachel and Shuah looked at me. “Rich people have money,” Rachel said.

We didn’t have any money, that was for sure. Rachel was dating a soft-hearted grad student from a poor town in the Maritimes and Shuah was law-school-thousands-of-dollars-in-debtpoor. Me, I was still paying off student loans from my undergrad years at McGill.

My mother worked a government job at an arts agency, and though she would have given me her last cent even if it meant she’d have to live in a tent across the street, she couldn’t spare much. I needed $40,000 at least. My dad was a full-time writer. He’s also pretty successful, but he’d just gotten married and bought a house and I knew every cent was headed in that direction. I needed to widen my contacts. I needed rich people.

“Okay, so how do I get money from them,” I said.

We mulled it over.

“I suppose you could just ask them,” said Rachel.

A scheme started to take shape. I knew I could write a funny letter if I needed to. I also knew from reading magazine profiles of millionaires and from watching Annie that rich people were often eccentric. I did some creative visualization, Shakti Gawain style: I pictured a big man sitting in a chair, reading my letter, and reaching for his chequebook. I pictured him calling out to his secretary: “Put this in the mail, Gladys. This girl’s got spunk.”

Rachel was working for a business magazine at the time. She left the room and came back holding an issue. Canadian Business Richest 100. “They do it every year,” she said. “It’s a list of all the richest people in Canada.” It was a start.

A few days later, I got started on my letter. I’d made the mistake of telling my friend Amy my plan: I wanted to write letters to the 100 richest people in Canada asking them for money for grad school. She told me to drop it. “At the very most you’ll make $200. And you’ll be royally embarrassed.”

I couldn’t picture the big, cigar-smoking man in my fantasies sending such a pathetic sum. “Two hundred!” He’d laugh. “That’s one caviar spoon for me! This girl deserves more.”

So I wrote the letter in one sitting, making my case as convincingly as I could. I told them about my poor parents, about all the scholarships I’d applied to that had rejected me. Canadian scholarships were out because I wanted to study in the States, and American scholarships were hard to snare, unless you had astonishingly high marks and several decades of community service under your belt. I had neither. The unwritten code seemed clear: arty writer types with pretensions need not apply.

“Greetings rich, kind and generous bene-

factor-to-be,” my letter began. “I am pretty close to desperate, and, short of selling matches like a certain heroine in a Hans Christian Andersen fairy tale, I’m plum out of ideas. Could you find it in your heart to support this rather unlikely cause? As in, me?” And then the pitch: my great love for journalism, my desire to travel to Africa and report on the AIDS epidemic (at the time, a totally sincere ambition), my early days as the editor of a high-school paper. And then the personal touch: a few well-chosen details I’d culled from research: “Your work ethic, of course, is legendary ... starting out as a newspaper boy at age 12, then working on the railroads for 10 years,” etc. It was important to me that every letter seemed personalized. And finally, the Return on Investment. I promised to send my benefactor a funny letter once a month. And they would have the satisfaction of knowing they’d helped a young person with her dream.

It wasn’t much, but it was all I could promise. (I chose not to send a photograph of myself, despite suggestions from friends. I wanted them to be intrigued by my words, not my face.)

My desperation to get out of town wasn’t as simple as I put it in the letter. I didn’t want to put in all my motives: some of them seemed less than noble. I was still numb from the end of a love affair with a much

older, much involved man and couldn’t imagine walking around the city anymore without him. I was working as a researcher at a groaning monolith of a public broadcaster: people my age seemed to disappear inside its walls as associate producers and emerge 20 years later with only slight job changes and not much more money. Also, I worked in a unit full of women who spent their days waiting for feedback from a taciturn, mustachioed tyrant: producers always came out of meetings wringing their hands and wondering, “What can we do to make


M. like it?” It was a dead end and I knew it.

Also, two years at school in California sounded pretty spectacular. I’d visited California a year earlier and had stayed in my friend’s filthy commune. I’d spent a day on Berkeley’s journalism school campus: an enchanting collection of Craftsman buildings with a sunny courtyard where students in jeans

and sundresses smoked cigarettes with their profs. I sat in on a class and listened as the students discussed Anne Lamott’s Bird by Bird and a few New Yorker profiles. And then there was the climate (80° F every day, no snow), a climate that made all other climates seem unreasonable and just plain cruel.

I copied down the names of the millionaires from Canadian Business, and spent the next few weeks looking up the addresses of rich people. Most of this sleuthing was simple:

I looked up the addresses of the companies they owned and then sent a letter to that address. A lot of envelopes went to banks in the Bahamas. The richest 100 were an interesting mix: media barons, tech geniuses, oil tycoons. Some of them had stories I thought suitable for rich people: Jimmy Pattison, No. 5 on the list, had narrowly escaped death when a fire broke out on his yacht. Some sounded nutty: Jeff Skoll, No. 3, used to run eBay and now wanted to make epic films in the tradition of Gandhi. Some had exoticsounding names: Carlos Fidani, a real-estate tycoon who made his fortune in Orlando, was someone I imagined lunching with people like Uma Thurman and wearing sunglasses and driving sleek, dangerous cars.

The rejection letters started arriving in May 2005.1 collected them and reread them when I wanted to feel tragic and like my plan had no legs. Charles Bronfman’s secretary sent me a nice letter saying I had obvious writing talents and a sense of humour but that he didn’t give to individuals, or to the Foundation of Maggie. George Weston’s assistant sent me a form rejection letter. Lino Saputo’s assistant sent me a form letter saying that they preferred to direct their resources toward organizations involved with sports, family activities and healthy living. I thought I qualified for healthy living. Saul Feldberg, a “media shy” founder of Teknion Corp., the office furniture company that first produced a tilting chair for under $100, said no. No elaboration on that one.

And those were the ones who replied. Mostly, I got no responses to my letters.

I started to feel depressed and embarrassed (as Amy had predicted). One thing cheered me: considering the circles I travelled in, it was unlikely I’d ever run into these folks at a party.

In the middle of May 2005,1 got a letter from a real-estate tycoon who wanted to know more about my plan. (He’s asked me not to name him, so I’ll call him S.)

I wrote back, and told S. that I needed $10,000. I sent him a copy of my admission letter and my budget. He wrote back three days later. “I like your style,” the letter said. “You have my commitment for the CDN$10,000 as requested. Maggie Gilmour, pack your bags. You’re going to Berkeley.” I went out for a glass of champagne but told no one. My benefactor, as I would soon start to call him, said I was welcome to the cash, but he wanted to keep it secret.

Two months later, I got an email from the personal assistant to an oil tycoon. The oil tycoon promised $16,000, on the condition that I communicate with him through his personal assistant and commit to doing well at my studies. I agreed and 10 days later got a cheque in the mail for $16,000.

I was going to school. And all I had to do was write letters. (I warned them I couldn’t provide them with expert political or economic analysis of the situation in California, but I could provide them with breezy, firstperson accounts of a Canadian abroad, studying in America. Sort of like Daisy Miller, but not in Europe and without the galloping consumption.)

I arrived in Berkeley in September 2005, and started writing my benefactor letters exactly one month later. I wrote about the million orientations I had to attend, including the international one, in which we were warned, like Jews in German-occupied Europe, to never travel without our paperwork: this visa, this stamp, this passport—keep them close. I wrote about meeting a forlorn group of exchange students who told us what to expect when socializing with “superficially friendly” Americans: “When an American says they will call you,” said a sad-faced girl from Israel, “it doesn’t mean they will call you. It also doesn’t mean they are your friend.”

Writing the letters was easy, a writer’s dream

assignment, in fact. I was writing for an audience that I already knew liked me and was fond of my style (or they wouldn’t have bankrolled me). After the first few I sent out, it became clear that I wasn’t going to be burdened with any of the details from my benefactors’ lives. I poured out the details of mine, and got not much in return except for a few thank yous and “keep it up”s. I got the occasional reply that highlighted the surreal nature of our relationship: “Glad to receive your letter, I am headed to Egypt,” or, “Have received your letter but have been unable to reply; am playing polo in South America.”

Slowly, the personalities of the two men began to emerge. S. was sympathetic, kind, and unabashedly on my side. When I was down, he’d tell me to believe in myself, and


that I could do anything. He signed his letters “fondly.” D. was gruff, to the point, and more military in his dispatches. “Received your letter,” “was pleased to hear,” etc. S. was personal, telling me I had spunk and chutzpah: and when a boyfriend dumped me, he became my personal Oprah, writing: “He blew his chance to be with you. His loss, not yours. Time to move on.” D. was cooler and less effusive. “Sorry to hear that,” he wrote. “Things will improve.”

They were both kind, especially so when I was suffering. Summer of first year we had to intern at a small paper. I chose one in Kentucky; naively, I thought I was headed to the soft and gentle South: I was going in search

of gentleman callers and dark cool porches where people sit in rocking chairs and drink mint juleps and tell endless charming stories. But when I got to “the South,” I wrote them letters describing what a disappointment it all was. I ended up in Louisville, Ky., and Louisville was anything but the hot, hushed Southern romance I imagined it would be when I read Truman Capote. It was a hot, stuffy town full of fat white people and angry black people. I wrote newspaper stories about eccentric graveyard managers and born-again Christians, but almost died of loneliness in my little studio, which was full of cockroaches (“They’re water bugs, honey,” my Southern landlady tried to tell me) and had a TV that only got two channels: local news and CMT. I dated an ex-Iraqi soldier who bragged that his kill ratio was 100 per cent (“I hate towelheads, and I don’t have a problem killing them”), who gave me the worst case of strep throat I’ve ever had, and then, when I called him from the hospital, said he couldn’t talk because he was with his girlfriend. I wrote my benefactors: “Forgive me, but I have to start this letter with a bit of tragedy...” and

then waxed about my suffering. S. responded by saying: “This is all part of the path. Be strong.” D told me to be brave, and that he knew I’d get through it. I sat at my desk and wept, grateful for their gruff kindness.

It wasn’t until June 2007 that I was put in the awkward position of having to say no to one of my benefactors.

In June 2007,1 was scheduled to graduate in an old-fashioned ceremony that involved caps and gowns, a long speech by a journalist who’d been blown up in Iraq and was just getting his life back on track, and patient relatives sitting baking in 100° F California sun. I’d finished my master’s project, an 8,000-

word chapter about NGO workers in Nicaragua (one of those projects you can pursue in graduate school before the icky realities of the marketplace dictate how you spend your time), and I was spending the last few days crying and trying to get out of my lease early. I rounded up a few family members to come to the ceremony—my mum, and my grandfather were coming—and then got an email from S. wondering if he could come.

I said no. “If you come, I will be so focused on you being there that I won’t be able to pay attention to my family,” I wrote. He responded gracefully: “I assure you I completely understand, and thank you for being honest. Might my consolation be to have you describe the occasion to me in your usual colourful manner?”

I regretted my decision and couldn’t sleep

for days afterward. I couldn’t imagine how awkward it would be and how I would navigate it: how would I introduce him to my friends? How would I explain him to my grandfather, who was travelling nine hours to see me graduate? Who would he talk to? But I should have found a way to make it work.

It wasn’t until more than a year later that I was able to apologize to him in person, when I met him for the first time, one lovely fall day in 2008.1 was in Montreal to see friends and I set up a lunch with S. at a French restaurant in Mile End. I didn’t sleep the night before. Would he be disappointed? Would I measure up to my letters? I arrived at the restaurant after nearly hyperventilating in the cab on the way there. S. was a short, pink-faced man in a striped suit with a tiny, brightly coloured sports car. He was polite in an Old World way,

choosing wine for us and telling me what I should order. We talked about the financial meltdown in the States, the Canadian election. I thanked him half a dozen times, and apologized for the graduation fiasco. He told me he understood, and left it at that. The lunch was impersonal in a way that made me think he’d either barely read, or forgotten, all my letters. I was slightly disappointed to realize that he didn’t know me, and I certainly didn’t know him. We ate salmon and green salad, and a perfect lemon tart. Over coffee, I asked him why he’d done what he did for me. His answer was simple: I liked your letter. He didn’t seem disappointed that I hadn’t landed a fancy, well-paid job right out of grad school. “Life rarely works out that way,” he said.

“You’ll figure things out,” he said kindly, and then added, “I’m just glad I could help.” M