One in five Canadian private sector businesses are led by women in 2026 and every single woman focused on growing their business or choosing entrepreneurship knows one of the keys to success is finding community.
A born and bred Winnipegger, Charmaine Jennings launched Strategic Charm, her digital marketing and content creation agency in 2016 while living in Alberta. When she returned to Winnipeg, Jennings saw minimal options for business networking that wasn’t stuffy or formal.
“I love blazers, but I didn’t want to be in a space that was automatically a place you needed a blazer,” explained Jennings. Wanting a laid-back environment that was more like herself, she created Hustle + Charm in 2017, a networking membership for Winnipeg women entrepreneurs who want to connect with fellow entrepreneurs, learn from each other and participate in professional development focused on the needs of small business owners.
Almost 10 years later, she has created a place for education, collaboration and friendship among Winnipeg’s women and non-binary entrepreneurs.
“Having a team of bad-ass / supportive / inspiring women in your corner can make all the difference to your success ”
“Hustle + Charm is a super fun, no bullshit, safe space for women to gather regularly and have honest conversations about the ups and downs of building a business.” - Charmaine Jennings
Q&A with Charmaine
Why did you want to launch Hustle + Charm?
Many networking possibilities were all about finding new clients, not sharing the realities of being a business owner. I wanted to foster a ‘come as you are’ environment to network with people, learn from each other and find common ground.
What happened during the first year?
The launch was exciting – 35 people were in attendance and we signed five members. I started with free, casual monthly meet-ups. But I soon realized people were confused – I used the social media marketing channels of Strategic Charm to promote Hustle + Charm and no one understood the difference. In 2018, I created separate social media channels for Hustle + Charm and saw the interest and membership steadily grow.
Our members are from a wide range of industries including real estate, marketing and cleaning services; they’re always interested in discussing and learning about taxes, personal finance, bookkeeping, software and investment.
How did Hustle + Charm grow?
At its peak, Hustle + Charm had 80 members. In 2019 I expanded the concept to three other cities. I drove to Calgary, Halifax and Montreal: I felt these cities would welcome a laid-back approach to networking, unlike the bigger cities of Vancouver and Toronto where I felt there were already existing associations and networks.
How did the pandemic affect Hustle + Charm?
Covid was a big disruptor. We had to shut down the Calgary, Halifax and Montreal groups in 2020. The way we connected, networked, and exchanged information dramatically changed. We're still feeling the effects of covid and we’re realizing the importance of community.
How are you fostering community in 2026 with members?
We previously launched a book club but it didn’t do well. Then a member, Siuleen Leibl who owns Milksmith, an ice cream store in Winnipeg, asked about launching a book club. The new iteration is a partnership with Leibl and we’ve named it Sweet Reads Book Club.
We alternate between personal development and business books. In the summer and in December we mix it up with a book that is lighter or more fun. At the book club meet-up, we always have an activity like making bookmarks or learning about the ice cream store, as book club meetings are hosted at Milksmith. It helps those members who may feel awkward meeting new people with a way to connect and relax. It’s open to the public and free for members.
What program has been the most popular with members?
Peer-to-peer mentorship has been one of our main successes – its also free for members. We ask those who want to participate if they prefer someone in their industry or someone from another industry. The duo meet biweekly to hold each other accountable with what they want to do with their businesses. It encourages everyone, whether they are newbies or 20 years in business, to share with each other.
Everyone knows something they can share about being a business owner; you can always learn. As well, the Hustle + Charm blog provides resources, tips and interviews to help and inspire our members.
What’s on your wish list for the future of Hustle + Charm?
My dream is to be able to offer a funding grant for small businesses. Many business owners believe money is the one thing they need for growth. Although it’s not always the only solution, it can certainly make a difference.
I would also like to expand again – I would launching Hustle + Charm in Calgary. I was recently there and met with the community to see what they would want to do. That city embraced the previous version of Hustle + Charm and had the most active community.
What’s next for Hustle + Charm?
In October 2026, we hosted our first weekend retreat in Gimli, Manitoba – The Expansion Retreat. A two-day all-inclusive retreat to help business owners plan for 2027. It included business and financial planning, strategy, marketing, branding and feedback sessions and photo/video workshops. There were also wellness activities and time to reflect and recharge. I hope to do more of these retreats!