As told to

You’re currently following this author! Want to unfollow? Unsubscribe via the link in your email.

Shawn Asselin started his company when his son was an infant. Courtesy of Shawn Asselin

2026-02-03T15:07:01.227Z

• Shawn Asselin started a men’s underwear company just after his son was born.
• He was unhappy at his corporate job and quit about a year after launching.
• The experience has confirmed that he never wants to work a corporate job again.

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.


Shawn Asselin couldn’t find the underwear he liked, so he designed his own. Courtesy of Shawn Asselin

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.


Courtesy of Shawn Asselin

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.

• as told to
• Parenting

Read next