a sisterhood of Winnipeg lady bosses who learn together, grow together, and kick ass in business.

Having a team of inspiring and supportive women in your corner can make all the difference with your success.

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"Already feel the love after my first event! The vibe = most comfortable I've ever felt around a group of strong women."

Karina Walker, Rising Strong



When I couldn’t find the right tribe of female entrepreneurs to join, I decided to boss up, take matters into my own hands, and create something I felt was missing in Winnipeg – a super fun, no bullshit, safe space for local lady bosses to gather regularly and have honest conversations about the ups and downs of building a business.

The ladies of Hustle + Charm come together to share ideas, collaborate on projects, gain and strengthen business skills, seek and offer support, push one another further in our entrepreneurial journeys, and have a ton of fun in the process.

You can be part of a community of women who are as passionate about the empires they’re building as they are one another. That's what will provide the motivation you need to keep pushing towards your goals.

We’re business owners. We’re learners. We’re friends.

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We don’t compete with one another; we celebrate each other’s successes.  

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Public events

The women of Hustle + Charm are doing amazing things, and we want you to be a part of the action! Whether or not you’ve registered as an official member, there are plenty of ways to have some face-to-face interaction with our current lady bosses through public networking events and workshops.  

Check out our calendar and signup for an upcoming event!



"Do you like parties? I do enjoy a good party.  And it seems like every time I’m with this girl? Party. I was introduced to Charmaine 1 year ago….and….my party level has increased royally. In Hustle + Charm, we actually like each other….like, we like to hang out together and it's not always about business connections and networking. We don’t keep attendance, and ask how many referrals one has made each month….phew! As a matter of fact….we hang out more than we network! Because of Hustle and Charm I am meeting my best/dream clients. The group has given me a boost and encouraged me to step out a little more in areas of strength."

Carly Koop, The Light Refinery

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We don’t shy away from real talk; we share our fears and our struggles.  

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We don’t keep each other small; we raise each other up as high as our dreams will take us. 

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This community was born from a hunger for connecting with other local female entrepreneurs on an authentic level. No judgment, no comparison, just support. If that's your jam, we'll tell you the whole story behind Hustle + Charm and it's founder, Charmaine Jennings.


"I won a three month membership to Hustle and Charm and renewed it with dolla bills when it came time because I can’t picture my growing business without this support group. Hustle and Charm is work therapy, encouraging, safe and helpful as I encounter challenges and successes. Knowing people in a myriad of industries keeps my curiosity piqued for the next cool idea!"

KATHERINE MAGNE, WInnipeg Sews/Franglaisewn

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