Confessions of a Serial Entrepreneur – Mark Sherry
Confessions of a Serial Entrepreneur – Introduction
Hi, I am Mark Sherry a serial entrepreneur from North Bay, Ontario Canada. I have founded nine companies in the last twenty-five years in a whole bunch of widely different industries, including restaurants, explosives, mining software, board games, software sales, consulting and most recently a grocery shopping app called gofer.run.
Confessions of a Serial Entrepreneur – What the Pandemic Made Me Do
During the pandemic I was watching as governments collectively lost their minds. And one of the things that really set me off was the fact that Walmart stores and Amazon warehouses could stay open and sell shoes while the local shoe stores had to close. At the time one of the shoe stores in North Bay was the oldest independent shoe store in Canada.
Confessions of a Serial Entrepreneur – Start in a Small Place and Grow
Today’s article is called “Start in a Small Place and Grow”. I am sort of picking it up where we left off on my last post. Now everything you read about a start up says start small, make mistakes, fail quickly, make changes and learn how to get the flywheel going. So, we picked where we were living North Bay as the place to start small.
Confessions of a Serial Entrepreneur – Trying to Find the Aha Moment
When you start a new business there is a moment when you go Aha, I get it and you can see a clear path to success. You never know if it will arrive or if it will come. Until that moment arrives you are scrambling to get there, and the moment only comes if you are successful, otherwise there are a lot of Ahh moments.
Confession of a Serial Entrepreneur – Sh!t Happens
Bit of a recap – I am a founder of One Red Maple which created an app that redirected sales out of large corporately owned online stores to locally owned businesses. Think of the modern-day equivalent of Robinhood. It’s still a great idea, but maybe we were ahead of our time given the current focus on supporting Canadian owned businesses.
Confession of a Serial Entrepreneur – What Now?
It is early February 2024 and after we reduced our numbers to the core at One Red Maple, we met to decide what the pivot will be. We gathered the remaining team to look at ideas. Everyone remaining was required to come up with their best ideas. The idea was to take the technology or skills we had as a team into the new venture.
Confession of a Serial Entrepreneur – The Grind
After we decided on groceries and the name gofer.run, we needed to figure out if we could do this technically. This is where the development team comes into play. Now before we build anything we need to make sure we can do the things we need to do technically, or all is for naught. So, we needed to find out if we could search the stores in real time, process the data through AI and then use an algorithm to find the lowest cost options based on how many stores the users are willing to go to.
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.
Confession of a Serial Entrepreneur – Small Changes Big Ripples
At the end of the last post I said I was 23 and started a maternity store, I think I was actually 24 when it opened. At the time I was on a contract with Canadore College doing liaison officer activities. One day I bumped into a friend downtown who said he was going to Europe for six weeks.
Confessions of a Serial Entrepreneur – Pivot and Scramble
If you recall from the last post my maternity store is struggling along and I need to make some tough decisions. There are only two decisions I can make, shut it down and take the losses or try to grow the top line (revenue) with the same level of expenses. I chose the later – sometimes when you are digging a hole it is hard to stop.
Confessions of a Serial Entrepreneur – The Launch
There is nothing that creates more excitement and anxiety than the launch of a new product. And as I sit here six days away from our launch (Jan 12) of gofer.run it is all starting to hit me again. We are madly working on all aspects of the launch from final upgrades of the app to finalizing the marketing plan.
Confessions of a Serial Entrepreneur – Stress & Ukuleles
Well launch date for gofer.run has come and gone, and we did not make the date. We got sidetracked and went down a rabbit hole, but we are back on track and moving forward. It is very easy to get sidetracked as everything is possible when you are building an app.
Confessions of a Serial Entrepreneur – The Sherry’s Trip to the Olympic Games – 2006
I know I said I would do a post about my time at Canadore College but since the Olympics start tomorrow, I thought I would have a little fun this week and post our short story of our family trip to the Olympics in 2006 in Turino, Italy with our wonderful friends the MacEachern’s. Like my business ventures my vacations are always a bit crazy.

