Inspired by Canadian Business’s fall 2022 issue, the first annual How I Made It talk series was held on October 12 at Microsoft Canada’s downtown Toronto office. 

Bringing together the city’s most exciting entrepreneurs, the all-day summit included live Q&As, breakout discussions and networking opportunities, and was sponsored by Signature Partner Amazon Canada, as well as Microsoft Canada and the Business Development Bank of Canada. The event was themed around the future of entrepreneurship and addressed timely topics like the future of work, e-commerce, brand development, product innovation and sustainability.

The day before the summit, Karen Danudjaja, the co-founder and CEO of superfood-latte brand Blume, joined Jason Maghanoy, associate publisher of Canadian Business and vice president of digital solutions and business development at SJC media, for a Zoom discussion about the difficult task of creating longevity for a start-up. “Resilience is not about what is happening today,” said Danudjaja. “It’s the idea of what your business will look like in 10 years that keeps you going.” 

The next day, the summit kicked off with a keynote fireside chat with Sinead Bovell, a futurist, AI expert and founder of Waye, an organization that helps youth learn about AI. The talk covered what the future of work might look like when AI technology is implemented more widely. “There are things we can’t even imagine,” Bovell said. “The jobs of the future haven’t even been invented yet.” 

After a brief audience Q&A, guests and speakers mingled while enjoying lunch by Elle Cuisine and soon, everyone was invited back for the How I Made It talk series.

The panel consisted of mini-talks about the future of entrepreneurship from six inspiring entrepreneurs. First up with Derrick Fung, founder and CEO of Drop, who gave a talk on the three things you need to get started as an entrepreneur. 

Elke Rubach, the founder of financial-planning company Rubach Wealth, then explained the importance of surrounding yourself with people you trust. “Build your village,” she said. “Because if you do it alone, you’ll fail. It’s okay to ask for help.”

Next, founder and CEO of e-commerce platform Bonsai, Saad Siddiqui, gave a candid talk about how to run a company during a challenging time, discussing what he and his employees learned about keeping afloat during a crisis period in the business. 

Jenn Harper, founder and CEO of cosmetic brand Cheekbone Beauty, then took the stage to talk about how your beliefs can drive innovation. “Making an impact on people with minimal impact on the planet” is key, she said. “When we built this business, we followed our values.” 

Managing director and head of global expansion for Amazon Ads, Tamir Bar-Haim, continued the talks with a conversation about intrapreneurship, or building a business within a business. He explained how the giant corporation’s “day one mentality”—acting like it’s the first day of a start-up despite Amazon’s over 20 years in business—drives innovation. 

The talk series ended with Robin Goodfellow, the owner of restaurant Vela and founder of Little Bones Beverage, who shared with the audience how he supported his employees as his restaurants shut down during the pandemic and how he’s rebuilding after a series of professional setbacks.  

Guests then broke out into smaller discussions to connect more intimately with leaders. One breakout session was led by Fung who chatted about the basics of entrepreneurship, another was led by Siddiqui about e-commerce best practices, and the third was led by Maghanoy who discussed how to manage people in a hybrid work environment.

The day came to a close with a fireside chat with Microsoft Canada’s president, Chris Barry. The discussion covered trends within Canada’s tech sector, such as the persistence of hybrid-work structures, the growing desire of entrepreneurs to do good and the importance of investing in cyber security. Barry also shared the sectors that he believes made strides to digitize during the pandemic, such as financial services, and those that are lagging behind, like travel, which was shut down for most of the pandemic and is now failing to keep up with post-lockdown demand.  

As the last stop for the day-long event, guests were invited to Oliver & Bonacini’s Sap for a closing-night dinner and fireside chat with Michael Katchen, the founder and CEO of Wealthsimple. While guests enjoyed Sheringham Distillery Gin cocktails with their meals, Katchen and Maghanoy sat down to discuss scaling your business. Katchen even shared that Sap was actually the site of Wealthsimple’s first-ever fundraising win.

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