Overdraft: When One Half of Two Wheel Gear’s Founding Team Wanted Out

Illustration of Reid Hemsing
In this series, I speak with people who know what desperate feels like. While now blooming into success, these founders share with me their deeply personal financial struggles and lessons learned on their way back to black.

Reid Hemsing was only 26 when he was raking in an enviable salary in Alberta’s lucrative oil and gas industry. Every morning, he’d pack his work clothes in a bike bag designed to transport suits and every evening, he’d return home from work (by bike) to sew those very bags in his basement. Two Wheel Gear was very much a side-hustle, and for three years, Reid invested money—and his evenings and weekend—in the brand without turning a profit.

But in 2014, in a grocery store parking lot, Reid had an epiphany. “I had a moment where I was just like, ‘If I stay on the same course, I know I’ll be very financially successful, but I’m not really building the legacy that I want.’” He quit his oil and gas gig, left family and friends, and moved to Vancouver to dedicate himself full-time to Two Wheel Gear with his new business partner.

But in his first year, after the high of scoring a purchase order with national retailer Mountain Equipment Co-op (MEC), he was delivered a blow: his business partner wanted out. On the hook for loans, with all of his money invested in the business, Reid was stranded. How would he pay out his partner and stay afloat?

In Reid’s own words:

“I had saved, like, $33,000 in my corporate career. I had put that money into getting the company started, securing an office space and buying a bunch of used desks and chairs. Then, we took out two loans totalling $85,000 to get our manufacturing rolling. We didn’t really have much money to pay anybody in those early stages. After you’ve been in a corporate environment for a while, with a good paycheck, you kind of lose that sense of where money comes from.

In December 2014, my partner came in one morning and said he wanted out of the company. And he wanted $40,000. He had only put in $4,000 about eight months earlier. We didn’t even know if the bag would sell. We were kind of pre-revenue with a few online sales. All of our money was debt, and it was all going to manufacturing, and I just didn’t have any money to pay him. A year before, I was thinking it was gonna be this amazing rockstar ride, and now my partner, who had become like my best and, dare I say, only friend in Vancouver at that time, wanted out.

I try and do everything on my own, but I realize that you need to ask for help sometimes.

I didn’t know what I was gonna do. I kind of felt like everything had imploded and that maybe I should just give up. I drove 12 hours back to visit my parents. We didn’t really talk about it for three days. My dad’s a pretty old-school, quiet, hardworking dude. He doesn’t like to talk about money. But on the last night, me and my dad started sitting and drinking some scotch, and he basically asked, ‘How much do you need?’ I’ll remember that always.

It was hard—getting broken down and hitting rock bottom—but I feel like that brought me closer to my parents. That was the first point, I think, where they actually started to get what I was doing and why it meant so much to me. I try and do everything on my own, but I realize that you need to ask for help sometimes.

It felt like it was just a lot of pressure and stress on my shoulders, and I had left a good gig and lots of friends.

Going back to Vancouver dragged me down on my knees a little bit. It was super lonely for a little while. I’d just barely make it by every month with just taking enough money out to pay off whatever I had put on my credit card, and then just try and get through the next month doing that too. It felt like it was a lot of pressure and stress on my shoulders, and I had left a good gig and lots of friends. I didn’t want to be that person that goes off and is just this huge dreamer, and then just, like, fails right away.”


Reid would go on to win a regional trade award as “best marketer” for his work on Two Wheel Gear and be selected as a G20 Youth Entrepreneurship Delegate, a global network of founders. Since his first purchase order from MEC, Reid has seen Two Wheel Gear’s sales double through the national retailer each year. He also now has his bike garment bags shipping directly to customers around the world.

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Illustration by Germán González

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