Jenna Hutchinson had been a goaltender for the U of M Bisons women’s hockey team and was planning to apply to dental school when a chance viewing of the television show Cake Boss changed her life.

“[I] thought that it looked like a lot of fun, and I wanted to try making a cake, so I went out to buy everything I needed to make a fondant cake, and just instantly got hooked and fell in love with it,” she recalled.

Hutchinson began to hone her craft, making cakes to order through Facebook. She started by selling her cakes to friends, but as word spread, she realized she could turn this hobby into something much bigger.

“And Jenna Rae Cakes was born!” she exclaimed.

Hutchinson opened Jenna Rae Cakes in March of 2014. Word spread quickly, and a few weeks in, she found she could not manage the business alone. Her twin sister, Ashley Kosowan, then a freelance graphic designer, was already helping with tasks such as the logo, website and interior design.

“I had helped out on the weekends,” said Kosowan. “And then [Hutchinson] was like, ‘Why don’t you just come work here? […] You can work on your freelance in between customers.’ And then I just never got to […] because there were too many customers.”

It wasn’t long before Kosowan joined Jenna Rae Cakes full-time as co-owner alongside Hutchinson, and since then the sisters have tasted sweet success.

The year 2024 marked a decade in business for Jenna Rae Cakes. Since its opening, the business has expanded from one location to four, with their newest bakery opening this past summer at YWG Airport. They have now employed about 40 people, some of whom have been part of the team for seven or more years.

Reflecting on their 10th anniversary, Kosowan and Hutchinson described the feeling as “surreal.”

“Normally when you hit a milestone like five years, six years, seven years […] you still feel like you’re still building, you’re still growing which we still are, but when you hit 10 years […] you just feel more established and like you’re becoming a real part of the community, you have staying power,” Kosowan said.

As a female-owned business, Kosowan and Hutchinson have been underestimated.

Hutchinson recalled when the bakery first opened and people would shake her father’s hand assuming that he was the owner.

Even today, some people assume there is a man or wealthy financial backer behind Jenna Rae Cakes.

“No, this is just us […] building it from the ground up,” Kosowan said.

The sisters have learned many lessons during the bakery’s first decade, highlighting the importance of having a clear vision of what they wanted for their company and sticking to it, while remaining open to feedback and change. They expressed pride in their positive company culture, crediting their managerial staff with establishing and maintaining it.

In 2020, Hutchinson and Kosowan released their first cookbook, Jenna Rae Cakes and Sweet Treats, which became a national bestseller and received praise from outlets such as Travel Manitoba and the Globe and Mail. Their second cookbook later garnered praise from Canadian baker Anna Olson.

This October, Kosowan and Hutchinson’s second cookbook, Jenna Rae Cakes at Home, was released, with book signings in both Toronto and Winnipeg. The cookbook puts a signature “Jenna Rae Cakes” spin on classic home recipes, such as waffles, French toast, pies and more.

“Instead of just a normal loaf of bread, it’s a Cotton candy twist loaf,” said Hutchinson, citing it as a favourite recipe in the book. “It just brings that magic of [Jenna Rae Cakes] home.”

The recipes are intended to be approachable and easy-to-follow for home bakers, with a range of difficulty from simple to more complex.

Something that shines through in Jenna Rae Cakes at Home is the authors’ love for family. Many of the recipes in the book are based on family favourites, including their granny’s walnut buns and their dad’s pavlova.

As the eldest of four children, the authors see family as “everything.” Two of their family members work alongside them at Jenna Rae Cakes. Kosowan’s husband, Trevor, runs the business with them, while their father manages their office and warehouse, and occasionally does deliveries.

“We’re really close with our parents, and we grew up watching them work really hard, they have great work ethic, and that was instilled in all of us kids,” said Kosowan.

So, after such a successful first decade, what plans do they have for the next one?

“We always kind of talk about this, and we always don’t fully know,” said Hutchinson. “I always would love to expand across Canada, but I know that entails a lot of logistical things […] It would be so cool to see Jenna Rae Cakes across Canada. I would love to see that one day.”

For now, they are focusing on their four Winnipeg locations, planning to review and refine their current processes to best prepare for the future of their business. They already have another cookbook in the works and hope to continue writing cookbooks as long as they can.

Hutchinson and Kosowan finished by expressing their gratitude to Winnipeggers for their endless support over the last 10 years.

“It’s been such a supportive community and the reason we’re able to be here for so long is because of Winnipeggers and Manitobans […] it’s really a huge part of our success,” said Hutchinson.

“We owe it all to the community that we’re in,” Kosowan said.

Jenna Rae Cakes at Home is now available through Penguin Random House Canada.