baking beauties
Life is sweet for Jenna and Ashley, the sisters behind the stunning treats at Jenna Rae Cakes
By Laurie Hughes
When Jenna Hutchinson, a science student on the cusp of a dentistry degree, opened a chic bakery on Winnipeg’s most fashionable street in 2014, she didn’t expect her life to change overnight. Within hours of opening, her macarons, cupcakes, and mini cheesecakes were selling out faster than she could make them.
Behind the counter of Jenna Rae Cakes, famous for both its delicious treats and stunning design, stand twin sisters Jenna and Ashley. Their determination and hard work have built a thriving business but beneath the picture-perfect façade lies a story of creativity, perseverance and countless sleepless nights.
Jenna, a self-taught baker balanced university classes, a part-time restaurant job, and her passion for cake decorating long before the first lineup appeared. After watching an episode of Cake Boss on the Food Network, she started making cakes for friends and family, and eventually her hobby morphed into a small business. One day she received a call from the city informing her she needed to register her business and use a commercial kitchen. It was a wakeup call, marking the shift from a side gig to a legitimate venture.
Convinced cakes were her future, Jenna found a restaurant kitchen to work in at night and built a business plan. Three years later, Jenna Rae Cakes opened on Academy Road. The early days were exhausting, with Jenna baking up to 18-hour days to meet demand. After just six weeks, she enlisted her twin sister, Ashley, a graphic designer with a keen eye for aesthetics, to help with the growing business. Together they turned the bakery into a success.
Ashley’s organizational skills perfectly complemented Jenna’s creativity. As Jenna dreamed up new products and designs, Ashley helped create a modern beautiful aesthetic for the brand. From elegant display cases to signature pink packaging, every detail was carefully crafted to delight the senses.
While Jenna is the dreamer, Ashley’s marketing savvy is intuitive. In the early days, they both baked, but as the business grew, they built a team of professionally trained bakers who helped manage production. Now, with four retail locations across Winnipeg and forty employees, Jenna and Ashley rely on their team’s expertise, while continuing to nurture the creative side of their business.
The bakery’s most famous treat is the macaron. While they aren’t the traditional French variety, their Italian-style macarons with unconventional flavours like Lucky Charms, Cherry Bomb, and gravy have contributed to the bakery’s success. “We’ve done everything by now,” Jenna jokes, recalling the time they created a gravy-flavoured macaron for Thanksgiving. “We thought it would be funny, and it turned out to be good!”
The duo’s rise happened quickly, fueled by Instagram, where their visually stunning products gained a fast following. “We were lucky to launch during the golden age of Instagram,” says Jenna. Ashley’s design skills helped create beautiful images that were posted before the shop opened each day. Those photos got them noticed by Martha Stewart Living and included in a wedding cake feature. Over time, despite their introverted nature, they shared their behind-the-scenes process and personal anecdotes which helped build transparency and customer trust.
In 2016, another connection made via Instagram led to an unexpected opportunity: Penguin Books approached them about creating a cookbook. What started as a passion project became something much bigger. By 2023, their first book was a New York Times and Amazon bestseller, selling 30,000 copies globally. It secured them a two-book deal, with their second book launched in 2024 already a bestseller. A third book is in the works.
Ashley, whose background as a photographer and designer is key to their brand, says creating cookbooks and cake decorating novelties has been a dream come true. Nodding to their high standards and design excellence, the recipes and images featured on the accompanying pages and the cover are reprinted from Jenna Rae Cakes At Home, sold at bookstores everywhere.
Despite their polished public personas, Jenna and Ashley acknowledge the challenges of running a business are far from a cakewalk. Their experienced team and family, including Ashley’s husband Trevor, the COO, and their father, Doug, who came out of retirement as their chief shopper and delivery man, makes the business deeply gratifying. “We all had to learn how to do things we weren’t qualified for,” Trevor says, referencing the difficulties of managing food costs, staffing and navigating the economy”.
“Everything on Instagram is a highlight reel,” Jenna says, “but there’s a lot more that goes into running a business than what people see.” Their high profile has also attracted attention from industry leaders, resulting in travel and teaching opportunities. In 2024 the pair flew to Australia and the UK as guest experts at industry events.
Despite their celebrity, the twins remain grounded. They prioritize quality, creativity, and, most importantly, their customers. They’re passionate about giving back to the community through scratch-made initiatives like their Birthday Cake Club, which provides birthday cakes to children in care at the Children’s Hospital, Ronald McDonald House and Toba Centre. “It’s important to us to use our business to make a difference,” Jenna says.
Looking ahead, the sisters dream of expanding Jenna Rae Cakes stores across Canada. Though, for now, they’re focused on fine tuning what they have, collaborating with other brands to grow revenue streams and adding joy to their customers’ celebrations in every cake they create.
Behind sweet and marketable exteriors are intelligent, charming, business savvy women with grit and honed skills that exemplify entrepreneurial spirit. It seems that hard work and resourcefulness, with a sprinkle of JRC Dazzle Dust make a sweet life possible indeed.
