Confession of a Serial Entrepreneur – In the Beginning – Don’t Let Your Kids Read This!

I look back at my life, and I wonder sometimes where did this entrepreneurial drive come from. My first job was delivering catalogues and flyers. At the age of 11/12 I filled up my wagon with those thick Eaton and Sears Catalogues and delivered them door to door. The spring/summer and the fall/winter were always the thickest and I would have to return home to restock as my wagon could only hold so many. I was paid something like $0.02 to $0.25 per item depending on the size of the item, those thick catalogues were at the top end. I probably delivered to about 200 homes. There were many times I came home frost bitten because I had to finish my route. After my first year I spent most of my savings on a digital alarm clock as a Christmas gift for my parents ($50). I also remembered thinking I was doing the same job as a postman (sorry there were no postwomen back then) but getting paid a lot less. In fact, my job was more difficult as I was delivering catalogues. As I write this, I think there are three hints in this paragraph as to why I turned out the way I did- the need to finish the route, the need to please people and figuring out that life was not fair.

Now Eaton stopped printing catalogues in 1976, but Sears persisted until 1993 (in the US) just two years before Amazon launched. In Canada they stopped producing a catalogue in 2016. If there ever was a company that should have been Amazon (that was not Amazon) it should have been Sears. They had the infrastructure to make catalogues, they had pickup and return depots, distribution networks, warehousing expertise, stores, suppliers, etc. They even understood that consumers would buy clothing based on a picture and that they did not need to try it on in the store before they purchased it. They were perfectly poised to lead in this new online space. They had it all except they bet on the mall and not online and the rest is history. Strategy matters. Sometimes as entrepreneurs we are worried about large corporate players stealing our ideas. In most cases an idea is irrelevant, it is the execution of that idea that is the key to success. No one is likely to steal your idea because with it comes a lot of work.

I started working early, maybe I was bored and my parents needed to occupy my time. I had “ants in my pants” as they used to say. When I was 13, I went to work with my father at Sherry’s Autobody garage for the summer (or parts of it). I worked 40 hours per week for $1 per hour which was below the minimum wages of $2.15 per hour. Now I know people reading this will say that’s child labour – but I liked it. I got to work with my dad, I learned useful skills, and I was taught the lesson of hard work. It was better than sitting home all-day playing video games (there actually were no video games at this time). I worked 7 summers with my dad and in the end, I was pretty good at autobody and was thinking about getting my mechanic B license as a backup plan. A couple of summers I worked full time with my dad and part time at A&A record and tapes. I loved that job as I love music. Once while working with Adam, a friend that got me the job we played the Flashdance soundtrack the entire day to see how many copies we could sell – can’t remember the number but we sold a lot. It was somewhat torture for both of us but looking back it makes me smile.

Now I was a reasonably smart kid but not a good student.  I did not like school and I spent a good portion of it in the cloakroom (that was where I was sent when the teacher had enough of me).  I was this way all the way through school just doing whatever I needed to do to get by and driving my teachers crazy, even made a few cry. I did assignments the morning they were due, studied sometimes and sometimes I didn’t. In high school I even wrote a book report on a book that did not exist, I just made up the book report on an imaginary book the morning it was due (got a B on it).  I never threw myself at school the way I did work. This even continued into university where I made up a whole research study for a social psychology class assignment – I got the top mark in the class 😊. I pulled all-nighters, learning an entire course in a night because I did not go to class.  I pulled this off except in one course called Operations Management which I failed. I never went to class, and I spent all night putting together my cheat sheet (it was allowed) but when it came time to use the formulas, I had no idea what they were for. Not proud of my education career to this point but that was the way I was.  Put me in a work environment and I excelled because I cared about the outcome.  I would not suggest this path for anyone going to school because when you graduate you have this feeling like you have some periphery knowledge, but it does not go deep enough and this has an effect on your confidence.  The one good thing about this type of behavior (besides the tremendous amount of fun I had) was the ability to focus in stressful situations – like learning an entire course in a night. This would prove to be a useful skill as an entrepreneur. Just an aside -I think education needs to be better aligned with the real world and when a teacher did that they caught my attention

Later on, I took two Master’s Degrees, a Master in Education and a Master in Business Administration.  I found school was a lot easier if you read the prescribed reading, did your assignments and studied for exams – imagine that. It was only after completing the MBA that I felt I had the tools to do something different.

Somewhere in the middle between working at the autobody shop and going to university I worked at McDonald’s Restaurant. I started working part time at McDonald’s when I was 15 and earned $2.15 per hour. It was fun working there.  We were the only fast-food burger franchise in town, and it was a hopping place.  Reminded me of Arnold’s Restaurant from Happy Days where all the kids hung out.  Everyone went to McDonald’s after a high school dance; it was the place to go. On a busy Friday night, we would do $1,500 in sales per hour (this is late 70’s).  This is where I learned the expressions “time to lean, time to clean”, and in order for the store to hum we had to practice the “three C’s Communication, Coordination and Cooperation”. Now on weeknights and weekends it was just kids working who were all around the same age and when the placed hummed it was fun to be a part of it. This is also where I meet my lovely wife dressed in her sexy lime green indestructible polyester uniform. This is also where I told the manager to “f… off”, something that I regret to this day – maybe a foreshadowing of my need to “work for myself”.

I graduated with a Bachelor of Commerce from McMaster University and got a job at Canadore College working as a liaison officer (salesperson for the college). This was a fun job that entailed me driving across the province attending College Information Sessions. I got a number of speeding tickets and once had to go for the “interview”.  It was more like group therapy for speeders.  This is where I honed my “spidey sense”.  I’ve got a pretty good sense of direction as this was the pre GPS/navigation system timeframe.  In smaller towns I would just drive to the town and guess where I would put a high school and head in that direction and most times I was right. (This skill actually came in very handy later in life when we had to get to Venice from Rome without a map or GPS in the rental car.  But I digress)

This chapter has been a bit of back story.  While at Canadore, I started my first business on the side called Baby Boom Maternity – read that again my first business at the age of 23 was a maternity clothing business.  I will talk next time about that venture and some of the entrepreneurial things I did while working at Canadore.