I was 34 years old when I started a side gig that turned into $10m. My goal was pretty simple- I was looking for ways to make more money. 

At the time I had a somewhat steady paycheque, but it was barely enough to cover our basic living expenses. Anyone that knows what it’s like living paycheque to paycheque will tell you that it’s not a lot of fun. Especially when my paycheque was based on my ability to sell. The pressure to perform was starting to wear me down. Truth is I was beginning to wonder if I’d walked away from one rat race only to join another.

I Quit A 6-Figure Job For This? 

Three years earlier I’d walked away from a 6-figure job and moved my family to a tiny fishing village in Nova Scotia, Canada. People said I was crazy. That I’d never be able to make as much money there. Some even suggested that I was an unfit parent. Their logic being that I had put my family’s financial security at risk.

I didn’t care. Moving to Nova Scotia was all about living where we wanted to live and having more time to spend with my family. And for the first year or two, just knowing that I’d escaped a corporate job that had made me so unhappy was all the motivation I needed. But then the grind settled in. I told people I was a small business owner, but in truth I was just an independent sales rep who sold B2B training solutions(mostly software based). I’d gotten off to a promising start but as time passed sales became harder to get. In simple terms, I’d grabbed all the low hanging fruit. Sales plateaued, business and living expenses increased, and the pressure was building. I didn’t seriously question my decision to quit that 6-figure job, but I was starting to wonder if we were going to be able to make a go of it in this little fishing village.

Opportunity Comes Knocking

A friend of a friend put me on to an opportunity to sell a new adult literacy/numeracy software solution. This was a real stretch for me. For my entire career I’d been working in B2B sales. This product would be sold to Community Colleges, School Boards, and Non-Profit organizations. And it was expensive! Literally 20 times more expensive than any of my current products. To make matters worse, the program had been developed in the United States and as a result all the math lessons featured imperial measures (a problem for a country that adopted the metric system in the 1970’s). On the positive side I did know a lot about educational software. And from a design standpoint, I knew that I was looking world class technology. The question was, would anyone buy it from me?

Test Before You Invest

At this very moment, all around the globe, budding entrepreneurs are hard at work building product solutions that have not been tested in the market. Almost all of these product solutions will fail. The reason is simple. People fall in love with their own ideas and assume the market will buy. 

Instead of arranging sales calls, I reached out to educators in my home province and asked for their help. There is a big difference between asking for help and making a sales pitch. I explained that I was thinking of taking this product on, but that I needed their help in making my decision. Using this approach I was able to get 30 adult/literacy experts in one room. They viewed a demo and asked questions of the developer. I didn’t make any effort to sell that day. I just listened, and I could sense that there was substantial interest. 

Listen To The Market

Encouraged by the initial response to the product, I started making sales calls to community colleges. A few were close to home, but most required a long drive and an overnight stay. The presentations went well, but it soon became clear to me that I was facing long and uncertain sales cycles. I was also up against a competitor with much larger marketing budgets and resources. And to make matters even more complicated, most potential customers did not have the money to purchase my product. They needed to apply for grants (a time consuming and uncertain activity).

Without realizing it, I began to spend more and more of my time on this new product. Six months in I’d reached the point where I was spending 80% of my time on a product that was providing 0% of my income. Something had to give.

So I Went All In

This one decision changed my life. I often hear the “experts” saying “never quit your job for your side gig until you have serious revenues”. The assumption the experts are making is that the only way to validate the potential for your side gig is by making sales. Don’t get me wrong. Sales are always a great sign. But that’s not the same as listening to the market. I was making sales with my existing B2B products. The problem was sales were flat and on the verge of declining. Selling to low hanging fruit is no assurance of a sustainable/scalable business. In my case I chose to listen to the market. My sales pipeline for the educational software solution was growing. I felt confident that some of those opportunities would begin to convert. So I made a big decision. I stopped all my B2B sales activities and focused solely on the new product. 

I Invested

A couple of months after I made that decision, I got my first customer. As the money started to come in I reinvested in my business. This included adding staff, traveling across Canada to set up a dealer network, and eventually hiring Canadian teachers to create metric math and Canadian Social Studies lessons. Two years in we moved out of my basement into a new purpose built facility. From that point on it was largely about execution.

The Results

In financial terms sales of this product exceeded $10 million. In personal terms, this side-gig turned full time business is the primary reason we were able to stay in this little fishing village. Thirty years later we’re still here. None of it would have been possible had I not found the courage to defy conventional wisdom, not once, but twice. Screw the Naysayers. Live the Life You Want. 

Tim Alison is the Host of the Screw The Naysayers Podcast. He also advices and mentors experienced leaders on how to start and scale a business around an idea or skill. Reach out at Tim@screwthenaysayers.com or www.screwthenaysayers.com

Tim Alison

Tim Alison

Business Mentor, Harvard Speaker, Magnify You Facilitator, Author x 3, Podcast Host at Screw the Naysayers

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