Serial Entrepreneurs Share Secrets of Successful Startups

While the media often glamorizes entrepreneurship, starting—and growing—a business is hard work. Doing it three, four or five times? That’s an uncommon and in some ways even astonishing achievement. We checked in with several of Canada’s serial entrepreneurs to uncover a few secrets of their range of successes.

Winnipeg’s Kris Thorkelson says serial entrepreneurs are always trying something new and they aren’t afraid to fail: “You have to be bolder and braver and stop worrying about rejection or making mistakes, because both can be instructional over time.”

Thorkelson began his career in the pharmaceutical industry, opening a chain of four pharmacies in his native Winnipeg, Manitoba, as well as two medical clinics. In 2001, he founded Canada Drugs, an online pharmacy company. Most recently, Thorkelson has made the transition into real estate.

According to Kris Thorkelson, “It’s the drive to create something out of nothing and watch it grow that motivates a person to shake off failure in order to achieve a degree of success in life – whether you’re a writer with a rejected manuscript, or like me, you have experienced some failures in business. It’s the motivation to create something new that helps you get past it.”

Peter Thomas, who recently turned 80, is the chairman emeritus of Entrepreneurs’ Organization and the past chairman and founder of Century 21 Real Estate Canada Ltd.

“I’m happy to report that life as an entrepreneur has kept me young,” says Thomas. Thanks to a portfolio of investments and ventures such as Dogtopia, Thomas is just as busy today as when he started down the entrepreneurial path in his early twenties.

“If you’re an aspiring entrepreneur who’s looking to change the world,” Thomas says, “I want to encourage you, because this life isn’t always easy. It’s difficult and often exasperating, with no guarantee of fame or fortune. But the rewards outweigh the risk if you position yourself for success.”

Rivers Corbett, another serial entrepreneur, is a TedX speaker, host of the Startup Canada Podcast, and founder of GoForth Garage for entrepreneurs. His passion is to use the experience and knowledge he has accumulated to be a mentor to those just starting out.

“These days,” says Corbett, “I am proudly fulfilling the role as Entrepreneur-in-Residence with Opportunities New Brunswick, where my focus is to significantly move the needle on the spirit and actions of entrepreneurship throughout the province. In 2018, I founded HeadSpaceFE, a strong community of Global Entrepreneurs, all sharing lessons from their journey and helping each other succeed.”

Joanna Track, the co-founder of Good Eggs & Co., also launched Sweetspot.ca and eLUXE, two of Canada’s top online destinations for women. She’s the force behind The Bullet, a Canadian destination for national and international news

“With all of my businesses,” says Track, “each one has had a distinct offering, yet they have all met a similar consumer need, which is making people’s lives easier. A basic principle of economics says that the end consumer’s desire and willingness to pay for a specific good or service depends on its ability to fulfill one of their needs.”

Track advises aspiring entrepreneurs to do research and identify a gap in the market that you can fill—“and then make sure you do it better than anyone else.”