Michele Romanow was a university student when she got her first smartphone, a BlackBerry. A little over a decade later, she’s the brains behind the $2 billion Canadian tech unicorn, Clearco (formerly Clearbanc). The five-year old fintech—which provides capital to e-commerce merchants often overlooked by venture capital—recently attracted $268 million in funding from Japanese tech-investment giant SoftBank. Now, Romanow and co-founder Andrew D’Souza have their sights set on an international expansion.

Romanow, 36, spoke to John Stackhouse and Naomi Powell about remote work, post-pandemic entrepreneurship and why “you never have a perfect idea.”


Michele, tell us what you’ve learned from the pandemic.

I’ve reconfirmed that I’m an extrovert. I never thought in a million years that Clearco would be a remote company. We had a rule that everyone was in the office, everyone had to move to Toronto. But I think this is going to be so liberating.

Beyond that shift to remote work, how else has COVID changed your industry?

We raised more than $300 million from a Zoom screen. And this was an industry where everyone said you had to meet in person. There was a contraction in deals in the very beginning. Then people just said, “Well, look, the world has to go on.” So we’ve found ourselves in a new paradigm.

Can we jump to the state of entrepreneurship? You’re a serial entrepreneur. How do you think the practice has changed?

Everyone now has to think digital first, and we probably would have had another 20, 25 years of in-person first. We were at the front of the airplane on this. We saw this incredible rise in e-commerce and digital commerce. We saw double the amount of new businesses created in the U.S. last year than any other year in the last 10 years.

What’s fueling that boom?

There were a lot of people that basically said, “Screw it, this is my life. If we live through the virus, I’m actually going to build my dreams.” And I think that’s going to be such a win.

Tell us about your own process. Do you wait for a great idea to strike or do you act on instinct about a space?

I go into every business with the view that it was largely created for historical reasons, not rational reasons. We don’t do things in society because someone sat down with all the information and said, “What would be the best option here?” And things continue to happen because no one challenges them. If you take that view, you can come up with so many ideas. The second part you mentioned is the difference between a good outcome and an extraordinary outcome: you have to choose spaces that are going through huge disruption. You never have a perfect idea.

You’ve also shown a knack for knowing when to exit a space. How do you know when to move on?

Telling a founder when to sell their business is kind of like telling a couple when to have a baby. It’s just so intensely personal. When we sold [Romanow’s previous venture, SnapSaves] to Groupon, I was so exhausted. Then I got a company like Clearco. And as much as this is exhausting in a different way, I could build this for the next 20 years.

You now have employees, I’m guessing, that you may never meet. How will you have to change as a leader?

The hardest part of being a founder is what gets you to stage one does not get you to stage two and stage three. My leadership style is to always get my hands dirty. There is no task to low or too high for me. That’s an important part of leadership. But that’s a completely un-scalable form of leadership when you are trying to enter 10 countries in a year. So I can’t have a one-on-one relationship with everyone anymore and in many ways, that completely breaks my heart. But I have to figure out now how to communicate on all hands.

You’ve mentioned Andrew, your business and life partner. As Clearco grows, you’ve had to hold each other to account. Is that easier as a couple or as individuals?

Andrew is an incredible product visionary. I am a much harder seasoned operator, and so we divide the company into what we call “horizon one” and “horizon two.” Horizon two is “How do we create long-term innovation?” What gives us the right to do that, is my part of the business, which is horizon one: making our numbers this year, making sure we’re operating and launching in these 10 countries.

How do you balance your personal lives amid that?

Most couples plan date night because they want to see each other. I see Andrew every single day. So we have to plan non-date nights.

We’re hearing about Canadian tech talent being poached by a wave of big U.S. companies. What are you seeing?

The market is wild out there. My favorite coffee table game is “what’s the craziest thing you seen inflation on?” People are talking about lumber and food and shipping containers from China. I’m like, “developer salaries are the craziest thing I’ve seen recently.”

What’s driving it?

The reality is we have great talent in Canada. And we’ve had many U.S. tech companies figure this out: people want to work in Canada, but now everyone is working remotely. So they went very aggressively into hiring our talent. But it’s a very competitive world and mission matters. At the end of the day, there is only so far that money pushes people. People have to do work that they care about and work that is technically interesting.

You put a lot of your personal life on social media. How should founders be thinking about those channels?

The first thing is if you’re going to choose to use social media as a tool, you have to protect yourself while doing it. I log off Instagram during the day for the most part because I just find it too distracting. The second thing is that people today are craving authentic. People want to hear from leaders, even if they’re wrong. I worry like everyone else about cancel culture but I think that pales in comparison to inauthentic culture.

This interview was edited and condensed for clarity.

For more thoughts from Michele Romanow on entrepreneurship and Canada’s booming tech sector, listen to our Disruptors podcast episode.

Listen on Apple Podcasts, Google Podcasts, Spotify or Simplecast


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