This as-told-to essay is based on a conversation with Shawn Asselin, founder of Willie Wagtail. It has been edited for length and clarity.
Since I was quite young, I’ve always been interested in businesses and — to be blunt — making money. I had a paper route when I was 12, and later built and sold computers in the early days of eBay.
I was the youngest of three boys. Because my brothers went to college, that was the only path I ever really considered. If I were from a more entrepreneurial family, I might not have gone to university or joined the corporate world, but the way I was raised meant the more traditional path seemed my only option.
By 2019, I was working in a corporate role, surrounded by people who didn’t care about the work as much as I did.
I couldn’t find underwear I liked, so I decided to create my own
At the same time, I was dealing with a personal problem: I just couldn’t find a pair of underwear I liked.
Because of the pandemic, I was working from home. Although I had a newborn and a 4-year-old stepdaughter, I had more free time because I wasn’t commuting. It was the perfect time to rekindle my interest in entrepreneurship. I wanted to see if I could build a better underwear option.
I didn’t know anything about design, but I figured it was kind of like building a computer: you have to Frankenstein parts together, then test them out. That’s what I did, with a lot of trial and error.
In March 2023, I started speaking with manufacturers in China. They asked me for a tech pack, and I didn’t even know what that was. I Googled it and learned it includes the measurements and cuts for garments.
At first, it didn’t seem possible that this would become a viable business. It felt like a pastime, but I really enjoyed working on it. Then, I connected with a manufacturer who understood exactly what I wanted, including unique features like a horizontal opening. The underwear we created was far above the brands I had tried, so I started to get serious about this as a business.
I drew on my computer experience to help design samples
My son’s name is Will, and a Willie Wagtail is a bird in Australia, where we live. One day, while walking along the beaches in Sydney, I realized it was the perfect name for the brand. It’s cheeky, since “willie” can also be slang for… You know.
I continued working on the brand while raising a baby and preparing for a wedding (we got married on Will’s first birthday). It wasn’t the best time to start a business, but it didn’t matter: I loved doing the work. I never struggled with motivation — in fact, I had to force myself to stop working so I could sleep.
We formally launched the business in November 2023, about 8 months after I first started playing with the idea. Within the first 10 months, we did about $100,000 Australian (about $67,000 US dollars) in sales. That showed me we were onto something.
I quit my corporate job a year after launching
That year, I was still working in my corporate role. If I had to go into the office, I would take the bus and work on Willie Wagtail during my commute. My goal was to leave the corporate world, but I didn’t have a specific benchmark for when I would do that.
Then, in December 2024, my contract was set to expire. We were fresh from Black Friday sales and in the middle of a busy holiday season. The timing felt right. I had a short conversation with my wife, and we both agreed that the company was doing well and would benefit if I had more time to put into it.
Now, it’s been just over a year of working full-time on Willie Wagtail. It definitely hasn’t replaced my banking salary, since we reinvest most of the company’s earnings. To date, we’ve done about $500,000 in Australia (about $336,000 in US dollars in sales), and we’re continuing to grow quickly.
I want to show my kids that entrepreneurship is a viable option
I’m confident that Willie Wagtail can capture a larger share of the market in Australia and New Zealand and eventually expand beyond that. Yet, even if this company failed tomorrow, I would never go back to a corporate role.
I’ve rediscovered my love of entrepreneurship and learned so much in a short time. I don’t think this will be the last company I build. I want my children to know that they can build a career from something they’re passionate about—even underwear.
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