The Pepperoni MBA: From selling pizza to running a billion-dollar company

I was three years into a four-year undergrad business degree. And I was impatient.
I had always known I wanted to be an entrepreneur. It started with washing windows for extra pocket money when I was a kid. By the time I was in high school, I had turned one of my hobbies – paintball – into a viable business. I opened a paintball field, using the profits to branch out into selling equipment.

But college was calling. I wasn’t sure it was for me, but I gave into convention and enrolled in a business program. From the beginning, it felt like I was moving in slow motion. Our first-year economics textbook introduced topics – supply and demand, marketing, diversification – I had already had to wrestle with in real life.

But I stuck with it, semester after semester. The prospect of being a “college dropout” was scary. The summer before my final year, however, I made a decision: I wasn’t going back. I quickly got used to hearing “You’re making a mistake,” from my friends and counsellors. It felt like I was burning a bridge.

Getting an alternative education

But it was the best mistake I ever made. Back home, I dove back into my first passion – running a business. This time it was a pizza joint. (Why? The margins are great … plus I loved pizza.) I leased a space and bought equipment using a credit card with a $20,000 limit. I was a one-man show, responsible for ordering supplies, making the pizzas, manning the cash register, mopping the floors, marketing, you name it. It wasn’t glamorous work – days were always long – but I was happy.

And, even though I didn’t know it, I was getting a crash course on startups. I got used to being strapped for cash and getting more out of less. I learned how to wear different hats – to be good at lots of things even if I wasn’t an expert at any. I had to think on my feet, juggle a dozen pressing problems and do so without losing my head. I learned the supreme importance of good customer service. I also discovered that Hawaiian slices easily outsell any other variety – It’s not even close.

Eventually, I realized I was meant for more than just pizza. By now, the ‘90s tech boom was in full swing. Computers had always been an interest of mine, ever since I won an Apple IIc in a programming contest in Grade 5. I wanted in on the action. So after a year or so of selling slices, I unloaded my restaurant and used the profits to move from my little hometown in rural Canada to the big city, Vancouver. I taught myself some coding and, with the money I had saved, opened an agency that designed web pages and web tools.

Persistence, ramen and a little luck  

My timing was terrible. The tech bubble burst right around the time I set up shop. Overnight, dot-com became a dirty word and investors began avoiding startups like the plague. Fortunately, all those nights pounding dough and chopping pepperoni imparted another lesson: persistence. I pieced together enough work (and ate enough ramen) to survive the lean times. Eventually, the business began to grow: first to two employees, then ten, then – after a few years – twenty.

Then, fate intervened. Around that time, social media was just starting to change everything. Facebook and Twitter had made the jump from the dorm room to the mainstream. Companies were trying to figure it all out. At my agency, we hacked together a tool to manage multiple networks from one page and called it Hootsuite. It was a simple idea, but it caught on, fast.

Today, Hootsuite has 15 million users, including employees at more than 800 of the Fortune 1000 companies. We count nearly 1,000 employees in offices around the world. And each day I get to work with some of the most talented engineers, designers and marketing minds in the tech world. Would I be here if I had stuck it out and got my business degree? I doubt it. I followed my gut and dropped out to sell pizzas. That – and a little luck and a lot of work – made all the difference.

To be clear, everyone is different and some people thrive in a traditional classroom setting. And formal education is obviously critical for certain callings. Dropping out and going it on your own definitely entails risk. But for me, getting out there and getting my hands dirty was essential to launching myself as an entrepreneur. That’s a big part of the reason why I started a charitable organization called The Next Big Thing where young entrepreneurs with great ideas – regardless of educational background – can get fellowships, mentoring and support.