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How bucking the drop-out narrative was key to my becoming a successful entrepreneur

From Branson and Gates to Zuckerberg and Jobs, the image of the successful entrepreneur who dropped out of school and nonetheless went on to find great success is as glamorous as it is ubiquitous. These “rebel entrepreneurs” almost make dropping out seem like a requirement for true maverick business cred.
It was briefly my story, too … but three months after I quit school in Grade 12, I was back in the classroom. And I don’t think I would have become an entrepreneur had I not reversed course. Everyone’s got their own style of learning, of course. But for newly minted entrepreneurs, romanticizing the “drop-out” narrative is probably as unhelpful as romanticizing the “stay-in-school” narrative.
For me, dropping out of school seemed like a good idea. Like many aspiring entrepreneurs, I had a hard time dealing with the structure of the classroom. The bells, the schedule, the rigid rules: they just weren’t for me. So at age 17, I impulsively walked into the principal’s office and quit. For the next few months, while my classmates were cracking the books, I was hauling lumber on a construction site in the dead of an Ottawa winter. It wasn’t exactly the wild and free creative lifestyle I had imagined.
After just a few months, I returned to school with my tail between my legs.
But I don’t regret my experience at all. Dropping out gave me a chance to see both sides of the coin and actually appreciate the value of an academic environment for entrepreneurs. In fact, it was pivotal in influencing my decision to go to university, which turned out to be the ultimate testing ground for my entrepreneurial ambitions.
I discovered how to sell ideas
In university, I finally found my educational groove. With much less structure than high school, I was able to do things at my own pace. I loved my political science courses at Bishop’s — I was, and still am, fascinated by the sale of ideas — but I also wound up taking every 101 class under the sun. I got a chance to explore different ideas, meet new people and find inspiration from mentors. Maybe it’s strange for a former high-school dropout to say but, as it turned out, I really loved school.
These days, I know a lot of fellow entrepreneurs who lament that they never went to college: an opportunity to, in essence, learn about human nature and what makes people, organizations and countries tick. You even see this these days in the renewed emphasis on including Arts in STEM education (now known as STEAM) to give students a more well-rounded experience. For me, this breadth of understanding, if only skin deep, has proven exceptionally useful in everything I’ve done since — a perspective I’d never have had if I’d been laser-focused on running a business from the get-go.
School was a perfect ‘beta test’ for businessInterestingly, while college afforded me a great way to learn about the world, it was also an unexpected education in entrepreneurship — campus turned out to be an amazing place to beta test my business sense. Looking for a way to pay for school one semester, I printed a bunch of parody-slogan shirts inspired by my university’s name (like “Bo Knows Bishop’s,” for anyone who remembers the Bo Jackson mania of the late ’80s) and set out on the first day of class armed with 400 tees. It was a small, low-risk investment, and I walked into a captive market filled with eager customers; I sold out in three hours.
I kept this t-shirt business going for the rest of college, branching out into gear for the rugby team and special orders for clubs. I even wound up hiring my roommate to help me keep up with the demand. The money I earned removed the financial stress of school. More important, though, I was able to hone my entrepreneurial skills with each passing semester. I got real-life lessons in managing inventory, marketing, design and collaboration.
‘Safe’ experiments helped me become an entrepreneurIn the end, I got two educations — one in academics and another in entrepreneurship. And it was the freedom to experiment with business in a low-risk environment that helped me take bigger risks down the line. This all proved integral when I started my own business, Coastal Contacts (called Clearly Contacts in Canada), which became the leading online eyewear retailer and ultimately sold for $450 million.
In contrast to the many rebel entrepreneur stories out there, I guess mine is rather tame: I dropped out, and then dropped right back in again. In the end, there’s no right or wrong way to become an entrepreneur. But I’d like to put a vote in for gathering as many data points as possible before taking the plunge. For me, at least, I’m sure that success came down to the cumulative education I got in the classroom, and outside it.


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