Rolling With the Punches

Michele Romanow freely admits she’s been beaten up a bit in her business career. Not literally, of course. But when you’re one of the country’s most successful (and most visible) serial entrepreneurs, putting up with a bit of pain is part of the job description.

“There is a level of masochism and just plain pain tolerance—like chewing glass—that is involved in building a company,” Romanow declares. As she explains, when it comes to founding a successful business, the winners are not necessarily the ones with the most innovative idea, the best pitch, or even the biggest bank account. Rather, they’re the ones who can roll with the punches. “Are you going to be the one that gets punched in the face every single day trying to build this business? And are you going to keep going? That’s what this feels like.”

It’s an observation she comes by honestly. By her own count, Romanow has been a founding partner in a dozen of her own businesses over the past 20 years (fully half of those by the age of 35) and an investor in perhaps 50 more in her 11 years as a panel member on Dragons’ Den, CBC’s highly successful entrepreneur reality show. These experiences have taught her that if you want to win at the startup game, you need to embrace the experience of taking a few body blows along the way.

“Businesses are complete chaos and almost fail a hundred times before they’re successful,” Romanow says. “You just talk about your greatest hits. You don’t talk about all the little companies and all the little pilots of everything that didn’t work out. This is one of the most important lessons for entrepreneurs: innovation comes from iteration. It comes from trying a lot of things.”

Over the past 20 years or so, Romanow has had plenty in both categories. She started her first venture while completing her undergraduate degree at Queen’s University in Kingston: The Tea Room, a zero-waste café, is still serving coffee and tea (32 different kinds, in fact) to thirsty students today. Her second, Evandale Caviar, started off equally strong, winning $100,000 in an international business plan competition before the business even got off the ground.

“It was never on my bingo card,” Romanow recalls with a smile. “I had never eaten caviar. In fact, I had never gone fishing. But you figure it [out on] a bunch of graphs and you [say], ‘Oh, this is real opportunity.’” Seed capital in hand, Romanow and her partners set up a commercial fishery and processing operation in New Brunswick from scratch, quickly racking up orders from chefs across the country—until the 2008 financial crisis put a wrench into those best-laid plans. Orders dropped off a cliff, and Romanow and her partners were forced to shutter the business within a few short months.

By the numbers, Evandale might be considered a failure. But in other ways, it was a smashing success, teaching Romanow critical lessons about the entrepreneurial mindset, particularly when it comes to picking yourself up off the mat when business (or life) knocks you down. “The learning curve was astronomical. Like, 10 per cent of the stuff that I wrote in the business plan actually happened in real life,” Romanow says. “But you will only figure out how to do business by actually starting to build it yourself. Moving from planning into execution is so important—it is something I still have to force myself to do today.”

After her (mis)adventure in caviar, Romanow shifted her focus to a number of online and digital businesses. In 2015, she co-founded Clearbanc (now Clearco), a fintech startup that provides capital to other founders based on revenue sharing rather than dilutive equity stakes. Recently, the billion-dollar business has expanded its offering to include advisory and strategic services—an example of Romanow’s desire to become a champion not only for her own businesses but also for all Canadian startups, and to encourage a new generation of entrepreneurs to put their minds to solving our nation’s problems.

“That’s just so rewarding for me, because you get to talk to people that are realistic optimists. They’re like, ‘I can see a better future. I can build a better future,’” she says. “When you actually care about something you see in this world, your ability to solve that and to change the course is really extraordinary.”

Even if it beats you up along the way? Romanow pauses for just a moment before she explains: “There is nothing that beats the exhilaration of building something from nothing.” One look at her smile—one that’s somehow completely relaxed yet full of energy at the same time—tells you that she means it. Literally.

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