How I got here
Why I left my $100K job at 27 and what happened since
Today I take sales calls from wherever I want to be: an RV in the mountains, a beach town in Brazil, a desk in Vietnam. A few years ago I was on a car lot in Hamilton, making six figures and wondering if this was all there was. Here's what happened in between.
The good money
I started selling at 17. My first real commission-only job was selling furniture, and I was good at it. For a kid who never cared about school, the money felt like freedom. I partied hard. It felt like living. Looking back, it was escaping.
The prettier cage
From there I moved into car sales and hit six figures by 25. On paper, I'd made it. But I looked at the older guys on the floor, the ones with the cars, the boats and the houses, and none of them looked free. It was a prettier cage, and I was walking right into it.
Around then I found a whole world of people on YouTube backpacking through Southeast Asia. They'd left their jobs for months, sometimes years, and they were living. For the first time in a long time, I felt inspired. I saved up, bought the camera gear and the backpack, and planned the trip for a year. I never went. I was too scared to blow up a six-figure life.
The year it all broke
Then COVID hit, and Asia shut down. Car sales went online, and since the older reps couldn't work the internet, every lead came to me. I worked harder than I ever had, for months. Then the rules changed, and the people who'd stayed home got paid almost the same as I did. New management cut my pay by $30,000. Right after that, my dad died.
I stayed home about nine months to help my mom and my family. And I kept coming back to the question I'd had since high school: is this all there is?
The leap
Asia was still closed, so I went to British Columbia to see a childhood friend I hadn't seen in over ten years. For the first time in years, I felt like a kid again. He talked me into a drive to Whistler, and I found a world I didn't know existed: people living in the mountains, snowboarding and mountain biking every day. It felt like stepping into a video game. I sat on a bench, looked around, and decided I was moving there.
I applied for a working holiday, got in, and gave my notice. Both my managers thought I was crazy and asked if I was okay. They were worried I'd go out there and get lost.
I learned to snowboard at 27. I made new friends and let go of parts of myself I didn't know were dragging me down.
When the season ended, I flew to Guatemala on a moment's notice with a guy I met at a bus stop, which kicked off the most insane, unhinged backpacking journey of my life.
When Asia reopened, I did it all again. I left everything, flew across the world and landed completely alone. I didn't speak the language, didn't know a soul, and I broke down. What have I done? But I'd committed to four months, and friends from home were meeting me in Bali, so I had to figure it out.
I learned how to make friends from scratch in a place where I knew no one.
I travelled all over Thailand, met up with my friends in Bali, and learned to surf, another one off the bucket list.
A year and a half of that. It was the best decision I've ever made, and by the end of Bali I had no money and a lot of debt.
The ticket
My options were minimum-wage coffee in Whistler or going back to car sales in Hamilton. Neither was happening. Then a friend told me about remote high-ticket sales and introduced me to a first-year closer who'd just earned $39,000 in commissions in two months. For the first time, I saw a way to pay for the life instead of burning everything down to chase it.
I went back to Whistler, took a job for housing and tried to learn closing on the side. I failed at both. So I quit with zero notice and went all in.
I lived in my RV that winter and took calls from it, parked by the slopes, running on a camp battery and a generator.
Once I got the hang of it, I was snowboarding every morning and closing deals all afternoon.
I paid off that debt within three months. Month one: $2,500. Month two: $4,300. Month three: $13,200 in commissions.
The ride
On a visit home to Hamilton, I met another closer who became one of my best friends. After a group dinner, he took me out for wine and hit me right between the eyes: "Let's move to Colombia." I thought he meant a group trip. "No, bro. You and me. Medellín. Let's run it."
I bought my plane ticket before we finished the wine. Medellín, then Machu Picchu in Peru, then Brazil, which came up along the way.
Three months of another unhinged journey, except this time I wasn't a backpacker burning through savings. I was a closer, taking calls from wherever we landed.
I even closed three deals from a laundry room in Peru, because he called dibs on the kitchen.
Since then I've closed deals from Canada, Mexico, Chile, Colombia, Peru, Brazil, Vietnam, Cambodia and Italy.
Nine months later, the same buddy talked me into a trip to Mexico, and I ended up in Tulum, closing deals between beach days.
One afternoon I was in a coffee shop up the street when a woman walked in and sat down in the chair next to me. I went home and told my buddy, "That's my wife." A few months later we moved in together, and we've been travelling the world ever since.
I never would have been in that coffee shop if I hadn't bought the ticket.
Why I teach it
The first person I taught was Charles, the same guy who hired me into that furniture job all those years ago. He was working long hours at a job that was going nowhere. He learned to close and blew his income up to $20K months in his first 90 days. Now every time I'm at his place, there's another renovation.
That's when I knew. I built the Closer Mentorship for people who feel the way I felt on that car lot: good at what they do, working hard, and wondering if this is all there is.
It isn't. The life you actually want is available to you. See it clearly, pay the toll, and walk the path.
Buy the ticket, take the ride.