For two-time Canadian Olympian Jenny Casson, the drive to succeed and strive for better is her default. With two lightweight world records on the erg and appearances at consecutive Olympic Games, she has firmly established herself as one of Canada’s top rowers of the last decade. Now, she’s applying that same boundary-pushing mindset to solve a problem that has frustrated athletic women for decades.
Unexpected Beginnings
Jenny’s rowing career began almost accidentally after a growth spurt and subsequent stress fractures derailed her running career. A coach spotted her in the hallway at school and suggested rowing, a fortuitous encounter that eventually led her to the University of Tulsa on an NCAA scholarship.
But her journey wasn’t immediately focused. “I didn’t take rowing very seriously, and I definitely spent the first two years not focusing on rowing at all,” she admits with refreshing candour. The turning point came in her third year of university when she moved out on her own. “I started eating better and not partying, which changed my life,” she says. “I started getting faster, and I was like, ‘Oh, I like getting faster.’” That revelation set her on a path to the Canadian National Team and ultimately two Olympic Games appearances.
The Disruptive Mindset
What makes Jenny’s approach distinctive, both in sport and now in business, is her willingness to question established systems rather than simply work within them.
“I spent way too much of my career trying to get the answers instead of looking from within and realizing that the people who win have it inside them,” she reflects. This realization prompted her to take greater ownership of her training and performance.
Between her first and second Olympics, this independent streak evolved into a leadership style that embraced constructive criticism; both giving and receiving it. “We brought a growth mindset into the 2024 quad that allowed us to be very critical of each other in a helpful way,” she explains. “It was never out of spite. It was out of ‘You can live up to your expectations, and you can be better than this.’”
From Boat to Bra
“There’s this culture in rowing where you don’t wait for perfect conditions. You go when it’s rough, when you’re tired, when it hurts, and I wanted to bring that into my business too.”
This refusal to accept the status quo is now fueling Jenny’s transition to entrepreneurship with her athletic bra company, Daylillie. Rather than incrementally improving existing designs, Jenny and her business partner Manu are completely reimagining athletic support for women.
“What companies are doing because it’s cheaper and faster is instead of redesigning the entire bra from the ground up, it’s like they’re just repainting the house different colours,” Jenny explains. “We’re going to tear that house down and rebuild it.”
The problem, as Jenny sees it, is fundamental: “The sizing has not changed since the dawn of time. It was designed based on a corset and a T-shirt in the 1930s.” This outdated approach fails women with athletic builds particularly badly, creating universal pain points that emerged consistently in their market research.
“Women who are 13, women who are 35, women who are 65 all have the same pain points,” she notes. “My bra makes me feel fat no matter what weight I’m at because it squeezes me in all the wrong places,” or “I lift my arm and my entire bra comes with me.”
Bringing Athletic Values to Business
The skills that made Jenny successful as an elite athlete are proving invaluable in her entrepreneurial journey. “Not being right and getting other people to constructively criticize you in a way that doesn’t hurt your feelings, but is for the betterment of yourself, that has served me so well,” she says.
She sees clear parallels between building a boat’s speed and building a business: “In entrepreneurship, you cast your net and whatever you get, you have to accept for what it is. Sometimes you’re not going to like it. But you put yourself out there, and you have to make the best of that information, feedback, and results.”
A Different Kind of Team
Beyond the product itself, Jenny is passionate about building a company that embodies values often missing from her athletic experience. “Just being part of a company that’s by women, for women, with women really excites me,” she explains. “I would love to have had a female coach during my time rowing.”
This desire to create not just a product but a movement is evident in how she approaches growth. Rather than flashy marketing, she’s focused on authenticity and quality. “We’re not trying to create something fun and sexy… we’re trying to establish that this bra makes you confident and keeps you secure,” she says, acknowledging that this approach might not generate instant viral success in today’s social media landscape.
Instead, Daylillie is building in public, creating what Jenny calls “a sisterhood of the travelling pants vibe” where women try the prototype, share feedback, and pass it on. The approach emphasizes community and continuous improvement, values that Jenny honed through years of elite rowing.
Looking Forward
As lightweight rowing phases out of Olympic competition, Jenny has stepped away from competitive rowing, at least temporarily. But her competitive drive remains undiminished; it’s simply found a new outlet.
With patent filings underway and product launch targeted for Christmas next year, Jenny is applying the same determination that earned her world records to solving problems that have frustrated athletic women for generations.
In both rowing and business, Jenny’s philosophy remains consistent: don’t accept the limitations of existing systems, look within for answers, and never stop iterating toward excellence.
“When I get into something, it’s really hard for me to stop wanting to get better and better at it,” she says. That relentless pursuit of improvement, whether measured in ergometer watts or customer satisfaction, continues to define her journey as she breaks the mould once again.
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