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.

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, signed a lease, and opened the doors with a plan that looked smart on paper.

I remember the first morning. I sat down and said to myself, okay, let the phones ring.

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.

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, and it was usually a wrong number.

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, and I lay awake asking whether I had made a serious mistake. Hence the MBA applications, my hedge, my parachute, my proof to myself that there was a respectable way out.

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 itself simply didn't work well enough yet, and the honest thing was to take it out. There is a particular flavour of failure in un-installing your own dream from a customer's wall, piece by piece, and carrying it back to the car.

My girlfriend came with me that day. She is my wife now, we married in 1995, but in 1992 she was a young woman standing in a parking lot outside a manufacturing plant, waiting while I dismantled the thing I had bet everything on, and telling me on the drive home that I shouldn't give up. She had a phrase she used in those years, three words, and she has kept using it for thirty more: you got this. She was there before the press, before the first big deal, before there was any evidence at all. Everyone else needed the phones to ring first.

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, which is a sentence I could not have imagined writing a month earlier.

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, the doors stayed open, and I quietly stopped working on the MBA applications.

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.