Shawn Asselin may have had a thriving corporate career in fintech but he has always been an entrepreneur at heart, a sense that goes back into his childhood. That passion for entrepreneurship was reignited when he saw a gap in the market for jocks that would ‘fit his needs.’ The side-hustle that would become Willie Wagtail grew into a successful six-figure business that Shawn would devote himself to full-time. We talk to Shawn to learn more about his journey with Willie Wagtail.
ISB: How did your interest in entrepreneurship at an early age begin?
SA: From a young age, I really loved earning my own money and buying myself something like a new video game. I started delivering newspapers seven days a week when I was 12. Shortly after eBay launched in Canada, I started flipping things on eBay. I even started building custom PCs and selling them on eBay. My fascination with ecommerce led to dropshipping for a few years as well. Those experiences planted the seed that I could one day build my own brand and it just happened to coincide with needing new underwear.
ISB: What gave you the confidence to create something innovative with Willie Wagtail given the ‘jocks’ market at that time?
SA: Nothing on the market ticked all the boxes I was looking for, so I started designing something without knowing where it would lead. I spent over a year developing the Willies, refining several versions of the design until they delivered all-day comfort where I can put them on and forget about them, no adjustments needed. That’s when I knew I had something special. Beyond the product itself, I saw a big opportunity in branding. With a name like Willie Wagtail, the brand naturally leans to the cheeky side and is memorable. Customers have really embraced it have left some pretty epic reviews on our website.
ISB: Coming from a corporate career, what was the most difficult aspect of your transition to be a full-time entrepreneur and how did you overcome it?
SA: I ran Willie Wagtail for a full year alongside my corporate role, so when I finally left, it was a calculated move. The business was growing and my wife and I agreed it was the right time to go all in. What I wasn’t prepared for was the loneliness that came with working on my own while trying to scale the business. Moving from a big organisation to being a solo operator was a real shift. The best thing I did was join an online business community. Connecting weekly with other founders who are facing the same challenges has been incredibly helpful.
ISB: How do you balance your roles as an entrepreneur and a father?
SA: Since starting Willie Wagtail, I’ve become very disciplined with my time and where I focus my energy. Balancing both roles became much more manageable once I left my corporate job. Running a business doesn’t replace a nine-five as I probably work more hours now, but the rhythm of the day is different and far more aligned with family life. We’ve also incorporated the business into our family. When we used to pack orders from home, my daughter was the order packer. We listened to our Taylor Swift playlist and packed the orders from the weekend!
ISB: How were you able to achieve a six-figure revenue for your business within the first 10 months of the business?
SA: In the year leading up to launch in November 2023, I spent my free time learning about selling online and building a brand. On my commute to the office, I listened to countless business podcasts, read books and watched tutorials on how to set up Facebook ads. I was by no means an expert, but had enough knowledge and skill to get to that result. Another thing was learning from mistakes and failures and embracing that it is part of the process. Mentorship was also critical. Being part of a business community where I can leverage knowledge from founders that have done it is priceless.
ISB: What is your vision for Willie Wagtail in the next couple of years?
SA: Over the next few years, my vision is to keep building a community around Willie Wagtail, whether that is through partnerships with different organisations, like the one we have with 1% for the Planet and by building deeper connections with people that are aligned with our brand values. We’re focused on expanding globally, especially beyond Australia and New Zealand. Most importantly, I want the brand to continue to have a positive impact in people’s lives and the planet. As we grow, our product range will expand based on market demand and feedback from our loyal customers. I’m also looking forward to growing beyond a one-man team, which will start happening in 2026. Exciting time ahead!
