Down to My Last Five Hundred Dollars

In the spring of 1992 I sat down and started preparing my MBA applications.

Not because I wanted an MBA. Because I was six months into running my own company, I was down to my last five hundred dollars, and I needed an exit that wouldn't feel like surrender. Grad school is what quitting looks like when you're too proud to say the word.

I should back up. Further than you might expect.

Long before I started my own company, I spent weekends sitting in my father's office. It wasn't because I loved accounting. It was because I loved spending time with my father.

As far back as I can remember, I would sit in the guest chair across from his desk while he worked, my feet barely reaching the floor, and listen while he spoke on the telephone or met with clients. He had a quiet confidence about him. He wasn't loud, but when he spoke, people listened. Employees would stop by his office asking for his opinion or advice. I watched that happen over and over again.

What fascinated me wasn't accounting. It was competence. There was something powerful about seeing a person become someone others depended on.

My father used traditional accountant's columnar paper, the lined sheets with all the tiny boxes. I would take unused pages home and pretend to work at my own desk, filling in imaginary numbers, simply because that is what professionals did. I wasn't balancing anything. I was pretending to belong in that world.

Looking back now, I realize I wasn't trying to become an accountant. I was trying to become someone whose opinion mattered. Only much later would I understand that I had been chasing that feeling since I was a little boy sitting quietly in the guest chair across from my father's desk.

I opened the business in the fall of 1991. I was 23, fresh out of a business degree, and this wasn't technically my first company. Through university I had run a small irrigation business in the summers, and it had done well enough to convince me I knew what I was doing. So when I found my angle, bringing new voicemail technology to Canadian businesses, I spent months preparing.

At the time I was living and working in California, and seriously considering not returning to Toronto at all. My girlfriend wasn't ready to make that move. We talked it through, and I agreed to come home. She would follow shortly afterward. While I was still in California, she began looking for office space in Toronto on my behalf. She found a small office near Yonge and St. Clair, and I signed the lease remotely, without ever seeing it in person. Looking back, it seems completely reckless. At the time, it simply felt like momentum.

My startup capital didn't stretch very far. I bought a few inexpensive desks and lamps from IKEA. There wasn't much else. No staff. No customers. No certainty. Just an office and an idea.

The first morning is still vivid. I bought myself a coffee and took a slow walk down St. Clair. It was one of those crisp, sunny fall mornings that somehow becomes permanently attached to your memory. I don't know why I remember the weather so clearly, but I do. I unlocked the office door, walked inside, looked around the empty room, and actually said out loud: okay, let the phones ring.

There wasn't anyone there to hear me. I wasn't making a speech. I was trying to convince myself that a business had just begun.

If only it were so easy.

The Security Guard Months

The plan was direct: get in front of the CEOs of downtown Toronto and sell them. So every day I put on my suit and walked into the office towers, one after another, and asked the reception desk for a meeting with whoever ran the place.

And every day, security walked me out.

Not once or twice. For months. I would enter a building looking for a client, any client, and be not so gently encouraged to leave. Then I would cross the street and do it again in the next tower, because I had been taught that this is what determination looked like, and I believed in the business, and I didn't know what else to do.

By about the third month, the security guards recognized me. They would see me coming through the lobby and save us both some time. I would walk out.

Meanwhile the meter ran. Rent, utilities, the little marketing I could afford. Money going out every week, nothing coming in. I was getting roughly one phone call a day. Every time it rang I would sit up straighter. "Digitcom..." "Yeah... is Mary there?" No. Mary was not there. Neither, unfortunately, were any customers.

That's the part of entrepreneurship nobody puts in the brochure. From the outside it looks glamorous. From the inside, that first year, it was painful, risky, and ego-bruising in a way I have never experienced since. I watched my university friends climbing their corporate ladders, collecting paycheques. Hence the MBA applications.

The few wins I did have were fragile. One of my first installations was at Fellowes Manufacturing, a real customer, a real system, proof the business could work. Then in 1992 I drove back out there to remove it. Not because I had done a bad job. The technology simply wasn't ready yet, and the honest thing, the only thing, was to take it out. There is a particular flavour of failure in un-installing your own dream from a customer's wall.

I remember walking down the hallway carrying pieces of the equipment in my arms. I remember deliberately looking away from the receptionist as I passed her desk. I couldn't bear the thought of making eye contact. In my mind, everyone in that building knew I had failed. They probably didn't give me a second thought. At twenty-three, embarrassment has a way of convincing you that your failures are public events.

Outside, my girlfriend waited in the car. She is my wife now, we married in 1995, but that afternoon she was a young woman in a parking lot outside a manufacturing plant, watching me carry my own dream back to the car in pieces. I climbed in carrying far more than a box of equipment. I was terrified. Six months into the business, nearly out of money, I couldn't see how any of it was going to work. I remember wondering whether I had made the biggest mistake of my life. By the end of the drive home I had mentally planned my funeral.

Years later I asked her what she remembered about that day. Her answer surprised me. She doesn't remember failure. She remembers watching a young man who refused to quit. While I was sitting beside her wondering whether the business would survive, she was looking at someone she was certain would find a way. She had more confidence in me than I had in myself. She said what she would go on to say hundreds of times over the next three decades: you got this.

Looking back, I've realized something that never occurred to me that afternoon. Entrepreneurs spend a lot of time borrowing money. Sometimes, before there's any money to borrow, they borrow someone else's belief. For a long time, I built my confidence on hers.

I had spent thirty years remembering that day as proof of how close I came to failing. She had spent the same thirty years remembering it as proof of who I was.

By spring I had five hundred dollars left. Unless something changed within weeks, not months, I was done.

The Last Gasp

The idea that saved the company wasn't mine.

I was driving down the Don Valley Parkway, taking my girlfriend to the bus station for her trip to Ottawa. She worked in marketing. Somewhere on that drive, listening to me circle the same dead ends, she said: you know what you could try? Press.

My first reaction was, sell them what? But the more I turned it over, the more I saw what she saw. A young entrepreneur launching a business in the teeth of a recession. A brand-new technology that could save companies thousands. That's not an ad. That's a story, and stories are the one thing newspapers pay for with the only currency I could afford: nothing. I had nothing to lose, which is a strategy all by itself when it's true.

So I made the calls. Cold, one by one, a 23-year-old pitching himself to newsrooms from an office where the phone otherwise never rang. The Financial Post first. They passed the story to a writer named Sonita, and she liked it. Then the Globe and Mail. Then the Toronto Star. Then the radio stations, and the local magazines and papers behind them. Within a month I was in at least five national outlets.

All of it from one idea, offered for free, in a car on the way to a bus station. I think about that sometimes when people ask me about those MBA applications sitting open on my desk that spring. The degree would have taught me frameworks. The drive to the bus station taught me that the best idea in the room is frequently not yours, and the whole job is being broke enough, and humble enough, to take it.

And Then the Phones Rang

I remember the first day it happened, because I remember what one call a day sounds like, and this was not that. The call was for me, from a stranger, who wanted to pay for my services. Then another. Then another. Inside thirty days I went from a few calls a week to ten and fifteen qualified leads a day. There were so many calls I had to hire a part-time receptionist just to answer them. Six weeks earlier I had been hoping the phone would ring once. Now I was hiring someone because it wouldn't stop. Entrepreneurs complain about strange things.

I want to mark something about that first week of ringing phones, because it matters later. It remains, to this day, one of the purest feelings I have ever had. Relief, yes. But also something else, something electric, that I would spend the next thirty years trying to feel again. I didn't know that yet. I just knew the phones were ringing.

The sales followed. I still remember the first big one, a deal worth more than fifteen thousand dollars, enormous at the time, and crucial in the most literal sense: a few more days and I would have been completely out of cash. The deal cleared, and the doors stayed open. The MBA applications sat on my desk for a few more weeks. I never mailed them. Looking back, I think they weren't applications. They were emotional support paperwork.

I closed the books on my first year with $150,000 in revenue. One decision, an idea offered in a car when I had nothing left to spend, was the difference between a company and a story about a company that almost was.

There Was a Business Here

For the first time, I stopped wondering whether starting the company had been a mistake. The phones were ringing. Customers were paying. There was a business here.

For years afterward, I told this story the way I just told it to you: I was almost out of money, and then the press gambit saved me. But that's not quite right, and I've come to believe the correction matters. I wasn't almost out of money. I was almost out of courage. The money came later. The courage had to come first, and it was running lower than the bank account.

I'll tell you something else that took me thirty years to say honestly. Failure was the more likely outcome. Not a risk of failure, not a possibility: the probable result. I was just another young entrepreneur with a lease and an idea, and most of us don't make it, and there was nothing about me in 1992 that exempted me from that arithmetic. What success does, quietly, over the years, is erase all the fragile moments when the coin was still in the air. Looking back, success feels inevitable. Living it, failure felt closer. Every founder's origin story, including this one, is written by the version of them that survived, and you should read us all accordingly.