By the time I reached junior high, my family had moved from Wisconsin back to Halifax, Nova Scotia. It was there, in ninth grade, that I learned one of the most useful lessons of my early life: when everyone around you is doing something the hard way, that is usually your opening.
The fundraiser everyone dreaded
Our entire ninth grade class was set to take a five-day trip through the Northeast, with stops in Washington, D.C., New York City, and a few other places along the way. It was the kind of trip you remember for the rest of your life, but it came with a catch. Each student had to raise a meaningful amount of money to pay for it.
The school's plan was the same one schools have used for decades. A third-party company supplied us with boxes of chocolate bars, and we were expected to go door to door selling them one bar at a time. I looked at that and felt no enthusiasm whatsoever. Knocking on doors to sell candy for a few cents of margin each was a great deal of effort for very little money. So I asked myself the question that has shaped my entire career: how can I hit this number in a smarter way, with less effort?
The pizza idea
The answer turned out to be lunch. I called the local Pizza Hut and arranged to buy their personal size pan pizzas, the small four or five inch ones, in volume. Then I turned my attention to the real asset I had access to: a school full of hungry students who would much rather buy a hot personal pizza than a chocolate bar.
I took preorders across the whole school, collected the cash up front, placed one large order, and delivered the pizzas at lunch two days a week. With the orders and the money handled in advance, there was no waste and no guesswork. I knew exactly how many to buy and exactly what I would make.
Scaling it up
It worked better than I expected. For about a month and a half I was bringing in four to five hundred pizzas twice a week at lunchtime. I paid Pizza Hut, kept a healthy margin, and blew past the fundraising target while many of my classmates were still working through their first box of chocolate bars.
The operation got noticed. The principal saw what I was doing and, to his credit, thought highly of it. But he also saw that other students were growing jealous of how well it was going, and eventually he shut it down. My guidance counselor, on the other hand, pulled me aside and told me I was the most likely person she had ever met to become a millionaire. I have never forgotten that.
The lesson
The pizza business taught me about leverage and systems. By collecting orders and cash in advance, I removed almost all of the risk and most of the effort. By choosing a product people actually wanted, I did not have to convince anyone of anything. And by questioning the default, I turned a chore into a real little enterprise.
It also taught me something quieter: when you succeed visibly, you attract attention, and not all of it is friendly. Goodwill matters, and it is worth tending to. That is a valuable thing to understand at fourteen.
Everyone was selling chocolate bars one door at a time. I sold lunch to the whole school at once.