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Two women connect at a How She Hustles in-person event.

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Emily Mills was in the final stages of organizing a pivotal event for her network of diverse women entrepreneurs and leaders, How She Hustles, when COVID-19 hit.

The 100-person family-style dinner was set for the end of May to celebrate the organization’s community’s 10th anniversary. But once large gatherings were banned, Mills realized it was time to get creative.

“At first, we thought ‘maybe we’ll just delay the celebration, we could push it back,’” she says. “Then once the reality set in, we realized we had to rethink this whole thing.”

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So, Mills and her team set off to reimagine how they could recreate the energy of a How She Hustles in-person event digitally. Prior to the pandemic, the network offered women who have historically faced barriers within business circles the chance to meet, learn, and celebrate their accomplishments. So like most small businesses across the country, when life went into lockdown, her network depended on her to find a way to carry on operations safely.

Emily Mills created How She Hustles in 2010 to bring together diverse women from Canada's business communities.

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“We know that people come to How She Hustles to learn and connect but also to have a fabulous time,” Mills says. “So, we worked with the team to build out a two-hour show that was meant to be a fun night in for my community.”

They had less than a month to put the event together, from learning to use new technology to organizing speakers, coordinating pre-recorded segments (including a video message from Prime Minister Justin Trudeau) and spreading the word about the celebration. “We were sweating buckets right up to the night before the event,” Mills admits.

“A lot of things could have gone wrong,” she adds, noting that technological errors were at the top of her list of concerns. “At a certain point, I remember just saying to my team, ‘We’ve done so much hard work. Now it just comes down to faith.”


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Thankfully, Mills says, the May 30 virtual celebration went off without a hitch. She and her “talented women-led team”expertly coordinated a dance demo to DJ sets, guest appearances and interviews. Over 700 people registered for the event, nearly double that of the most well-attended in-person event How She Hustles has ever hosted. Unlike most Toronto-based events, attendance at the virtual celebration was not limited by geography or cost – where most events are sponsored by brand partners and typically come with an entrance fee, the online anniversary was kept free to attend.

“We had people from around the world,” Mills says. “We were able to shout out people from Australia to Atlanta to Nunavut to Serbia to Ghana.”

The event’s success set the stage for what will likely be months of online events going forward. As in-person gatherings remain restricted, Mills is planning to move a number of her next to-do list items online – now, with the confidence of knowing that virtual events offer How She Hustles the opportunity to expand its reach across the globe. Mills plans to continue hosting events with a virtual element going forward, leveraging the wider net she’s cast to explore sponsorship opportunities in new parts of the world, grow existing brand partnerships, and sell tickets to new demographics of attendees outside of Toronto.

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“It was actually the perfect practice and a perfect opportunity to try out this platform and this way of connecting and building community online,” she says. “It was also a great reminder that we have the capacity to pivot and to adjust and innovate even under the most challenging times.”

Among her next newly-virtual tasks is production for this year’s edition of Startup and Slay, a digital series launched in 2019 to showcase Canada’s diverse women entrepreneurs for Small Business Week in October.

While Startup and Slay has previously sent filming teams out to business locations across Canada to capture stories in-person, Mills is recreating the magic online this year. That comes with its challenges, but it also allows How She Hustles to showcase a more geographically diverse range of business owners and reach a wider array of viewers than ever.


Mills says she's learned that moving events online can help grow her network's reach across the world. She plans to take the lessons from her latest event with her into the future.

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Any technological challenges that filming online may pose, Mills says she’s ready and eager to meet them. “It’s one thing to start something, but it’s another thing to keep it going,” she says.

Central to keeping her business going is financial support: through both corporate sponsorship and financial wellness expertise, Mills says her partnership with CIBC made the move to digital possible. “They have [been] an invaluable ally,” she says. “Even during this global pandemic, CIBC showed incredible commitment to How She Hustles and the diverse women-led businesses we support.”

Now, with a bit of hindsight and built-up momentum, Mills is approaching her next steps with a can-do attitude. Looking back, she credits the success of the How She Hustles 10th anniversary celebration to being honest, transparent and vulnerable. “Some of our great champions during this most challenging chapter of How She Hustles came forward because I wasn’t trying to pretend that everything was perfect.”



Advertising feature produced by Globe Content Studio. The Globe’s editorial department was not involved.

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