Confession of a Serial Entrepreneur – Sh!t Happens

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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.

We trialed the product in North Bay, Sudbury and Kingston and decided to just accept the lower usage rate of the app and increase the size of our market, because even a small share of a large market can make any company successful. This is our last crack so go big or go home. After two years of developing One Red Maple, we were getting ready to launch it across Ontario in November of 2023.

In September of 2023 I had a heart attack. It didn’t really feel like a heart attack, but I found out that any blockage is considered a heart attack. Just for your information cardiac arrest is when your heart stops. This was the first occasion in my life where I stayed in a hospital overnight. My heart was luckily not damaged but in the next few days I failed the stress test. Five years earlier I passed that stress test with flying colours, jogging on the treadmill at 7 to 8 mph. After my stress test failure, I went in for an angiogram and found that I had three blockages, the two key arteries going into the heart were 80 and 99 percent blocked and because of the location of the blockages the doctors recommended open heart bypass surgery. Five days later I had the surgery. I have run, cycled, swam, played hockey/sports and worked out for most of my life – except for the past three years as I pushed everything aside to focus on mostly One Red Maple as well as my other companies. The one common thing I have had in the past 25 years is entrepreneurial stress and I think it caught up to me. I have started 9 companies in the past 25 years and except for three A&W franchises the other ones were built from scratch, albeit most with other partners. Even two of the A&W’s were new builds.

Going from the expectation that I may have a stent or two to full on surgery does focus the mind. Realizing this could be the end, the one thing I did before going into surgery is I wrote my children a “Dad’s Just in Case” letter. To be honest I was a bit of a mess writing it and editing it. But after I had completed it, I thought everyone should write a letter to their spouse or children and leave it with their will as we never know when our days will be up, and it is a nice way to bring closure. In this case my wife Gina was there, so we just talked, and she also read the letter.

Now waking up from open heart surgery is no picnic, in fact I woke up earlier than expected after surgery and started wrestling with the nurses and doctors and they had to pin me down and re-sedate me. I don’t remember any of that and felt bad about it. It is a very invasive surgery which involves cutting your sternum/rib cage in two and then wiring back together. I was only on pain killers for a couple of days and then regular strength Tylenol after that. All the literature the hospital gave me relating to bypass surgery states that I would be back to playing hockey in three months. It has been 25 months since the operation, and I just played my first game of hockey about a month ago. I missed the exercise but even more the comradery. I am still in pain (this apparently happens to a small subset of people). For the most part I can push the pain out of my mind for most of the day. At night I need a heating pad and rest in my Lazy Boy…or maybe I am just getting old.

So, after I get back home five days after surgery, there are three things that were very difficult; sleeping, there is no comfortable position, and I could only get a couple hours before changing positions/locations. I slept in a bed, Lazy Boy, and couch. Coughing is painful but sneezing makes your eyes well up. I walked every day once I got home albeit only past a few houses on the street at the beginning but progressed quickly. After two months I went back into the office part time, which quickly becomes full time when you are the founder. Now to make it through the day I constantly had this warming pad on to relieve the neck, shoulder and back pain. I took it off for Zoom meetings. My team looked after the launch of One Red Maple in November across Ontario and did an amazing job, but we still had the usage issue staring us in the face.

At the end of December early January, we started to review the social media campaigns that we ran and while we were getting a reasonable number of downloads, we were not seeing much usage. Amazon has 353 million products available on their site, while the products we gathered from all the independent stores in Ontario was 7 million so in most cases, we did not find a match as our pool of products was much smaller.

In October 2023, while I was recovering, Mike and Eric when to a SOCAP conference in San Francisco. This is a conference about impact investing – companies that are trying to change the world through entrepreneurship. Mike as usual networked and met some interesting people, one being an ex-Google employee that helped run their Google X factory. The Google X team would look for Moonshot projects and then with a small team see if they could get some traction – this is how Waymo was created. So, in December, Mike and I headed to San Francisco (not sure that was a good idea but went anyway) to meet with potential investors but most importantly members and ex-members of Google X. They spent a few hours with us and the message was clear – we have not solved “what is in it for the consumer”? Without the consumers we are just fancy tech. A hard message to hear but they were right, and I really appreciated the time they spent with us. I always worried about going to Silicon Valley too early as I thought we needed our ducks in order before we stepped up to the big leagues. In addition to being the most capital rich investment region in the world another key component to the area’s success is the willingness to connect and help others succeed – you cannot underestimate the impact of this.

So, in January 2024 it became apparent that we had to reduce overhead to extend our runway. Since most of our costs were people, we had to reduce staffing numbers. Now for those of you who have never owned a business and had people work for you this is the most painful thing you must do. I view my staff as family/friends, and it is my job to make sure they stay employed, and if I must lay them off it means I have failed as a leader. In a lot of ways, a business takes on the personification of a person (somewhat Machiavellian) and it too wants to survive, and that business will make you do things that you hate doing in order to survive. So, at the end of January, we shrunk down the business to the core. There were a lot of sad people that day including me. I have always said I would much rather fire someone than lay them off.

A somewhat funny note is when we met with some venture capitalists to talk about funding. Because we have a lot of investors (+65) and my ownership percentage was not as high as usual after the seed round, he indicated that he did not like it as he wants to make sure the founder is committed. I bit my tongue, but I wanted to say, my wife and I have worked for free for three years building this, I had a heart attack in the middle of it and still I persist – is that enough commitment for you?

In the next post I turn my attention to “what the hell do we pivot to” and how we chose groceries. When I am feeling down for whatever reason it is sad songs that get me through that whatever. So here are three songs I listened to a lot during this period – Coldplay Fix You, Talk Run Away to Mars, and Joy Oladokun & Noah Kahan We’re All Gonna Die. I know the song list is a little depressing, but it works (for me at least).

Note: People always ask me what were the signs that made me to go to the hospital. Four things:

headache
tightness/soreness across my upper back
a little vertigo (dizzy)
and most importantly in my case was being winded (out of air) from things that never used to get me winded, like walking up the stairs at the movie theatre, where I was when feeling all of this. Of course, in true male fashion I drove myself to the hospital after the movie was over.