Within a few days of starting law school it became apparent to me that my original business (a promotional apparel company) was going to have to drastically change. At the time, a significant part of my sales strategy was predicated on building incredibly strong and long-lasting relationships with customers through constant in-person engagement. That meant considerable travel. When I started the business four years earlier, as an undergraduate student at McGill University, my schedule was extremely flexible and class attendance seemed almost optional. But law school was different, and it required my physical attendance every single day.

I needed to create a business that did not require my physical presence, but that would still allow me to leverage my experience in the apparel industry. I decided to launch on online shop selling licensed T-shirts.

One of my first tasks was to figure...