From a $500 Ford Ranger to Vanlife and $28,000,000 in Revenue

In high school, I volunteered at my family dentist's office one or two days a week. At that point, I had never even heard the word "entrepreneur." And when I finally learned what it meant, I didn't love using it.

It felt like a title reserved for people doing much bigger things than I was.

I felt like a phony. A fake. Like I didn't belong in that category.

But over time, I started to understand something.

Entrepreneurship isn't about a title. It's a mindset.

It's the willingness to keep hitting your head against the wall until something finally clicks.

It's solving problems when others would walk away.

That part I understood.

I've never been afraid of hard work, long hours, or taking risks. And that mindset pushed me to start building.

The Roofing Days

My first real business was a residential roofing company.

I started it with borrowed tools, a 1996 Ford Ranger, and my dad's old snowmobile trailer. At the time, I was working for another roofing company, and I used every dollar I earned to slowly buy the tools I needed to go out on my own.

I worked evenings and weekends on small jobs until I had enough work to make the leap. That first summer, I made more money than I'd ever seen before. I was hooked.

Not just on the income, but on the freedom.

Not the kind of freedom that lets you work less, but the kind that lets you work harder and be rewarded for it.

The more efficient I got, the more I made. I became obsessed.

That business gave me confidence. It taught me how to work hard, how to sell, how to lead a team, how to solve real problems, and deal with customers. It laid the foundation to think bigger.

The Accidental Software Journey

During those construction years, I became interested in software.

I was constantly building tools to streamline my workflow: Excel calculators for estimating, Access databases for CRM. I didn't realize it at the time, but I was slowly dipping my toe into the world of software.

Eventually, that curiosity led me to build my first software product.

It started as a scrappy referral tool I built for internal use. But when other creators and founders started asking for access, I partnered with a larger development company to turn it into a real business.

We ran that company for years. It grew steadily.

But over time, I burned out.

The problems became repetitive. The motivation dropped. Growth slowed. And the partnership began to feel one-sided. (It wasn't. I was just tired. They did what they promised.)

When the opportunity to exit came up, I took it.

It was the right decision at the time. It gave me a chance to reset, step back, and figure out what I wanted to do next.

Life on the Road

That next chapter didn't look like a new business. It looked like a van.

I built out a Sprinter van and hit the road with my dog, Ellie, and for four years, I travelled all over North America, living life on the move and documenting the journey.

That time gave me space to breathe. It gave me perspective.

And eventually, it reminded me of something: I didn't want to stop building. I just needed a new challenge.

Building The Wanderful

That's when I launched The Wanderful, an e-commerce brand focused on van life gear.

I'd always been fascinated by e-commerce. The idea of turning something intangible into a real, physical product, something you could touch and ship and see in the wild, was exciting to me.

But it also came with a whole new set of challenges:

• •Supply chain headaches
• •Overseas manufacturing
• •Inventory management
• •B2C marketing
• •Shipping logistics

It was hard. But it was fun again. And it worked.

The Growth

I started with a $5,000 investment.

• •Year 1: $20,000
• •Year 2: $171,000
• •Year 3: $878,000
• •Year 4: $1.8 million
• •Year 5: $2.4 million
• •Year 6: On track for $5 million

There were plenty of moments when things felt like they might fall apart. Delayed shipments, COVID, and tariffs. But with every challenge came a lesson. I continued to learn, build, and the business kept moving forward.

Buying It Back

Then in late 2022, I heard a rumour. The company that had bought my SaaS business was looking to sell it again.

A cold email and six months of negotiations later, I bought it back.

It's funny how something I once wanted to walk away from came back into my life at just the right time.

At first, I'll admit, it was ego.

I liked the story: "I bought back my business."

But as the deal got closer, I had real doubts.

• •Do I really want this again?
• •Do I have the time?
• •Will all the things that burned me out still be there?

Looking back now, buying it back was the right call.

The business is healthier than it's ever been. The ROI has been unmatched. And more importantly, it's fun again.

I'm working with great people, and for the first time in a long time it feels easy.

The SaaS Numbers

When I sat down to write this I pulled up the early revenue numbers:

• •Year 1: $5,600
• •Year 2: $99,000
• •Year 3: $197,000
• •Today: $1.8 million/year

It's hard to believe that the same product is now generating over $1.8 million per year.

It's lean, profitable, and continues to grow.

What I've Learned

What I've realized is this: the part I love most is the learning. Having an idea and making it real.

Every skill I pick up feels like a superpower I can apply to the next chapter.

And that's what keeps me in it.

I didn't follow a playbook. I didn't raise money. I just stayed in the game long enough to figure it out.

What's Next

The goal now is simple. I want to build a $10 million a year holding company, made up of bootstrapped, profitable businesses that let me live life on my terms.

Businesses that give me the freedom to travel, to train, and to unplug when I need to.

I'm not building for volume. I'm building for a life I actually want to live.

And my goal is to share the journey as I go.

So let's see where this goes.