Finding success out of failure

I shouldn’t be the one writing this. 

I was going to build a unicorn. I was going to build a company that would transform an industry and make a dent in the universe. I was going to be approached by a buyer with deep pockets and receive an offer (in USD, of course) I couldn’t refuse. I was going to be heralded as one of Canada’s best entrepreneurs.

But life isn’t about what should or shouldn’t happen. It’s about what happens. 

What happened was I built a shitty startup.

It was a slow growth startup.
It was a fake-it-until-you-make-it startup.

It was an always-in-search-of-product-market-fit startup.

Upon reflection, I don’t know if it was always a shitty startup, or if it was a good startup that just turned shitty. But the truth is it doesn’t matter. What matters is it never became the company I had set out to build at the start. Even though my team and I had brought an idea to life, launched a product to the world and built a small breakeven company with loyal customers, it was never a success to me.

I had failed. I had failed my team. I had failed my family. I had failed my investors.

In fact, this feeling of failure quickly became my obsession. It took over my thoughts, my emotions and many of my waking hours. It caused panic attacks and health concerns. It nearly ruined me. 

But then it didn’t. 

In November 2020, I sold my shitty startup. 

Despite the business being nearly destroyed by the impacts of COVID-19 (we had built a corporate entertainment platform, and corporate entertainment does not boom in a pandemic), I dug in, did the work, ran a process and found a willing buyer to acquire the business.

You can call this type of sale a micro exit, an acquire-hire, a soft landing or whatever you’d like. Truth be told, I don’t care what you call it. Selling my startup was an incredible life-changing experience. It was also one of the hardest things I have ever had to do. Even though the journey was difficult and the company never achieved the heights I envisioned upon launch, selling the business was still a great outcome given where we were at our lowest point. 

And so, in failure I was able to find a path to success. I was able to find an outcome that I could be proud of. Not because one presented itself to me, but because I put in the work and had the determination to forge the path myself. 

I believe my journey of finding success out of failure and, more specifically, running a process to sell my startup is a story worth sharing. Not because it’s remarkable or spectacular. It’s worth sharing because it’s a very common journey that many founders go through—but don’t often talk about.

In fact, over the last two years, I’ve spoken to nearly a dozen founders who have had “micro-exits” and journeys similar to my own. They built businesses that never really took off, faced significant challenges, but still found a way to sell the business before it destroyed them. Even though statistically more founders end up with these types of businesses than unicorns, these founders haven’t shared the details with many people. Why? Because failing hurts. Because shame is powerful. Because posturing and hiding behind a “we’ve been acquired” headline is easier than telling the nuanced truth.

I think it’s important to share these stories. That’s why I created this content series. This content series is based on my experience and the experiences of other founders who found some light in the darkness. This content series is for founders who have built something, but know their business isn’t going to be great. It’s for the tired, the realists and the ones looking to get out of a less-than-ideal situation and find the best path forward. This content series isn’t for you if you’re still building a unicorn—I have nothing to offer you and wish you all the best with that. 🙂

My goal with this content series is to be as honest as possible about the challenges with our startup, and to share stories, tactics and tools that could help you find your path to success through failure. Like the scene with Andy Dufresne, played by Tim Robbins in The Shawshank Redemption, crawling through a sewer pipe to finally escape from prison, I had to go through failures to reach the successes I’ve had today. Hopefully my story can ease your journey so it can be slightly less, well, shitty. 

Other articles in this series: