Jillian Harris puts on her teacher’s hat in this course for entrepreneurs and marketing mavens

Jillian Harris doesn’t like to sit still.

“If my team would let me, I would have 10 business plans on the table for you right now,” she tells BCBusiness. And her titles speak for themselves. She is the CEO of Jillian Harris Design Inc., co-founder of the Jilly Box and, most recently, the course instructor for her latest venture, Jilly Academy.   

But before she became a Kelowna-based celebrity, designer, entrepreneur and mother, Harris was just a kid in Peace River, Alberta, dreaming of all the things she could do with her life. “I always loved working. I actually have a picture of me from when I was four years old, cleaning tires at my dad’s [auto body] shop for money,” she says with a laugh. “I like creating my own systems and ideas. And I always wanted to be in a leadership position.” 

Harris had a lot of seemingly unrelated passions (like cleaning, decorating and wanting to be a flight attendant for WestJet), but she got her foot through the door at 19 years old when she started a company called Spick and Span. “I frickin’ love cleaning houses,” she says. “I was 19 and I had three employees. [When] I would go to school, I had people cleaning houses for me.” 

Jilly Academy

Finding her footing

At the time, Harris was studying at Calgary’s Mount Royal University. She wasn’t afraid to pivot—she switched majors from business to child psychology to travel and tourism, and then she started waitressing at the Cactus Club.

“I would fantasize about being an interior designer but I didn’t want to go back to school,” she recalls. “So I made my own business cards on my computer with perforated paper, back in the day, and I started staging and consulting for interior design. The owner of Cactus Club was looking for an executive assistant who could help with the interior of their restaurants and I told them I was an interior designer—which I was not—but I was kind of like, Fake it ‘til you make it.” 

And make it she did.  

Although Harris was managing projects and designing restaurants (including the launch of Browns) in her corporate role at Cactus, she eventually got fired for not fitting the “corporate mold.” She wasn’t mad about it, though, because soon enough she stepped into stardom on the Canadian versions of The Bachelor and The Bachelorette, followed by seven years of hosting Love It or List It Vancouver.  

But fame was never the goal for the entrepreneur—she saw it as a platform to build on her passions. “I like being a leader and a businesswoman because I love problem solving. That’s why just being a TV star was not enough for me. I needed to use my brain and my creativity in that capacity.” 

In 2019, she started her curated lifestyle box business, the Jilly Box, with just two people on board. And the same day that that project launched, busy bee Harris started working on the Jilly Academy. 

Courses in the Academy

Jilly Academy is a three-part online program for creators, entrepreneurs, marketers, small business owners and influencers. With courses on brand strategy, content creation and growth acceleration, Harris is looking to help people create a roadmap of their legacy through video lessons.

“It really explains how your personal values should be aligned with your business values,” she maintains. And those who aren’t visual learners have the option to purchase a workbook to use alongside the classes.  

Harris admits that the program might have a feminine flair (the branding is pink, the instructor undergoes many outfit changes and there are blooper reels at the end of each course), but it’s not just for women. One of Jilly Academy’s favourite customers is actually a plumber.

Since its launch in 2021, some 2,500 students are either currently enrolled in or have graduated from the Academy and another 250 have taken the course through its scholarship program for people who are financially strained or interested in starting nonprofits. 

Jilly Academy

One of Harris’s own favourite classes in the program is time-blocking from course two, The Content Creator. She says it helps her manage anxiety: “I’m not your typical creative, I like things in order. We can write down lists of things to do till the cows come home, but you can’t even start to create content until you have time-blocked it.” 

Growing the house of brands

Harris’s house of brands (which includes three seven-figure businesses) has seen revenues rise by 800 percent since 2017. She’s expanded Team Jilly from three employees to 22 and is a proud living-wage employer herself. 

If she had taken the courses when she was starting out in business, Harris claims that she could’ve avoided a lot of risks: “I had a company go bankrupt, I just about lost my husband, I had many nervous breakdowns. There’s a lot of things that happened that I don’t want to happen to my community.”  

So, in the Academy, she encourages people to follow their gut and pivot if they have to. “Your business success will come along with that,” she says. “And it may fail. Then you start a new business. When you’re confident in that legacy and you wake up with that as your purpose, the failing and opening of businesses becomes a secondary goal. It’s not as scary.  

“It’s never fun to win alone. It’s more fun if you have a community of people winning along with you.”