What happens if this goes right?

I remember watching the clock as the deadline approached. Every minute that passed, my anxiety rose. And then the deadline came and went. No email. No reply.

My heart sank. Did the past two years of my life just get taken away? Was I going to have to reinvent myself again? Did I have it in me to start over?

Let’s back it up.

In my past life I was a professional cyclist and five-time member of the Canadian National Team. It was a childhood dream that somehow came true. I thought it would be my career until I couldn’t race anymore, and then I’d retire like the world’s best athletes with a mansion and sports cars.

But that didn’t happen. Not only did my sport not have a ton of money in it, I never reached the heights that would have awarded me that outcome. That was on me.

At 24 years old, I walked away. The year I left, I finished second in the entire country. I was still physically and mentally able to chase the dream, but it no longer made sense with the long term in mind.

I had to reinvent myself. My identity was wrapped up in being a cyclist. The day before, I would introduce myself as Rob, pro cyclist. The next day, just Rob. Who was that?

What followed was a dark two-year discovery period. I tried many things, but nothing stuck. Sport was what I knew, so I enrolled in a Sport Management degree and got a job in the industry. The safe path.

Then in 2016, at 26 years old, everything changed. I decided to start a business. It felt like a calling. Business would be my new sport, and I would build a brand in the athletic space to stay connected to what I loved.

But I didn’t expect it to work. It was a pipe dream. Who was I to think my business would become successful? I had belief, but I also knew how unlikely it was.

So I thought, If I’m going to do this, it will be more fun with a friend.

In hindsight, this is the world’s worst reason to pick a cofounder.

I chose a friend from college. We’d met the year prior and became fast friends. I got him a job working alongside me as a field marketing rep, and we did all our school projects together. We worked well together. We got along.

But starting a business together is a different animal. A cofounder relationship should be taken as seriously as a marriage, if not more. You need conversations upfront about values, end goals, what hard work and commitment actually mean to each of you.

We had none of these discussions.

We split the business 50/50. It seemed reasonable, and it was the easier path. We didn’t have to have an awkward conversation about who should have more.

A lot of business problems, in hindsight, are the result of avoiding awkward conversations.

We got to work. Built the brand, developed the product, started selling. We miraculously did over $300,000 in our first year. That blew my mind.

I remember seeing an accountant early on for tax advice. He said if we made over $30,000 in four consecutive quarters, we’d have to collect and remit GST. I laughed and said there was no way we’d make $30,000.

That was my first lesson in not thinking big enough.

Our success caught the attention of my cofounder’s uncle, described to me as a “prominent businessman” in town. He wanted to meet.

At dinner, he questioned us about the business, and at the end slid a cheque across the table. It wasn’t a lot of money, but it was more than I’d ever seen. It felt like we were on Shark Tank and just landed a deal. I called my parents after and told them exactly that.

He invested and got 25% of the company.

We weren’t incorporated yet, just a general partnership. He said his attorney could help with incorporation, and to save on fees, we should give the attorney 3% of the company. I had full trust in him. Surely this was standard practice.

So out the gate, in year one, I owned only 36% of a company that was an extension of me, of which I did the majority of the work. I told myself this was the cost of help and mentorship. Surely this prominent businessman would help us skip the line.

His one trick up the sleeve was having us fly to New York over the Christmas holidays to meet a friend in the apparel space. The idea was we’d partner with her and develop an athletic apparel line to complement our socks.

Year one of business, with these people in our corner. How could we fail?

A week later, the apparel deal fell through. We were back where we started, except we’d spent all the investment money on the trip and given up 28% of the company.

The next year was the toughest of my life. The business was working. We were on track to double sales. I was working twelve-hour days, seven days a week. But my cofounder didn’t share the same desire to put in the hours.

Honestly, I don’t fault him in hindsight. It wasn’t what he signed up for, at least not in his mind.

The problem with me is that when I see an opportunity, I chase it down and dedicate my entire self to it. I became obsessed with business. Reading every book, listening to every podcast, speed-running my education and experience as fast as humanly possible.

My cofounder didn’t. Over time, the gap in knowledge and effort became too large to bridge. We couldn’t have thoughtful conversations about the business anymore.

Another problem with me is that if you want to be equal partners, I’ll hold you to my standard. And I won’t accept anything less. He did not respond well to this.

I don’t think anyone would.

Two years in, he quit. He was done. He walked away.

Then the uncle swooped in. The “partner” who had been nowhere to be found was suddenly here to save the day. He told me we should leave my cofounder with 15% to do nothing, and the majority of the clawed-back equity should go to him, because now he’d need to be more involved.

I knew this was wrong. But I was between a rock and a hard place. I had no money. Everything I had was going into the business. In fact, I was in debt. I had less than nothing.

I told myself the famous line: This time will be different.

I agreed. My cofounder kept 15% to contribute nothing. The uncle became near-equal partners with me. I was still responsible for all the work, plus figuring out how to cover my cofounder’s workload.

So I got back to work. Growing the business, hiring a team, on pace for our first seven-figure year. And the uncle who was going to be “more involved” was nowhere to be found. No help. Just pointed questions and criticism.

I was burning out. Working insane hours, every single day.

One night, at the absolute end of my rope, I wrote an email to my cofounder and his uncle. I laid out my view: the majority of equity in the company needed to be held by someone active in its growth. I had no ability to make decisions without their sign-off and no ability to properly incentivize a team to help.

How could they expect me to do everything while they sat back and contributed nothing?

I asked for a meeting to discuss.

What I received back was the final straw.

The uncle replied, removed my cofounder from the email, and tore me apart.

“If you think that only two years of hard work gives you the right or ability to think that you can change the partnership just because you don’t like how the partnership is at this stage you are gravely mistaken.”

“Your lack of understanding of having a partner and what it takes to build a business or how much effort it takes surprises me. If you feel this is too much for you then I will find somebody that can come in and run the company.”

This wasn’t the first time. I was always met with this belittling tone. It was toxic. It was traumatic.

That was the moment I decided to stop playing along. The pain of continuing had finally surpassed the fear of walking away. I hired my own attorney to explore my options.

We didn’t have a shareholder agreement. You think giving away 3% of the company for incorporation would include a SH agreement…

My options were limited. The only path forward was to threaten to walk away if they didn’t agree to a fair buyout.

I needed to regain control of the business without them, or move on and start over.

The idea of starting over was terrifying. The brand was me. It was my new identity. I had so much conviction in its success. But the pain of continuing in that structure was too much to bear.

I had a letter drafted. We sent it. In two weeks, I would walk away if they wouldn’t negotiate in good faith.

Two weeks went by. Nothing of substance. They froze the bank accounts and hamstrung my ability to run the business. It was not looking good.

After the deadline passed, I went home and broke down. Absolutely devastated. I couldn’t believe people could treat another person like this.

Was I perfect? No. Could I have been a better partner? Yes. But one thing was certain: this was my business, my idea, and my work that made it what it was. That wasn’t up for debate.

Then my phone rang.

There was an offer. There was hope.

$150,000 to get it done. Money I didn’t have.

I went to every bank in town, cobbling together every debt facility I could find. I scraped it together at what amounted to a 30% interest rate. A risk I was willing to take. I’d bet on myself any day of the week.

But then an angel appeared. My father-in-law, who had been a silent witness to everything I went through, offered to loan me the money at a reasonable rate and timeline.

The next day, we closed the deal.

It was March 2019, and the company was mine. I was the 100% owner. I had felt that way since the start, but now it was real.

My $150,000 MBA.

I think about that period constantly. Not because I’m bitter, but because I learned something that changed how I approach everything.

In business and life, we’re quick to protect our downside. We ask, What happens if this goes wrong? And we safeguard ourselves accordingly.

But the equally important question—maybe more important—is the opposite.

What happens if this goes right?

I never asked that question.

If I had asked, I would have thought harder about whether my cofounder was the right partner for the long haul, not just the early grind. I would have questioned whether this uncle was everything he claimed to be, or just someone who saw an opportunity to attach himself to momentum. I would have questioned whether giving up equity for basic incorporation was normal. Spoiler: it’s not.

These consequences don’t show up until it’s too late. They hide in the early days when you’re just trying to survive, and they reveal themselves only after the stakes have gotten real.

Failing because something didn’t work is one thing. But failing because something worked and you weren’t prepared to capture it? That’s a different kind of pain.

I know how unlikely it feels when you’re starting out. I know the voice that says Who am I to think this could actually become something? I had that voice too.

But if there’s even a sliver of belief that your dream might come true, you owe it to yourself to ask the question that protects your future, not just your present.

What happens if this goes right?

‍