YOU’D better WORK

BY HER 33RD BIRTHDAY LAST YEAR, MICHELE ROMANOW HAD LAUNCHED FIVE COMPANIES. NOW THE CALGARY NATIVE IS THE PRESIDENT OF A POWERFUL VENTURECAPITAL FIRM AND THE YOUNGEST-EVER INVESTOR ON DRAGONS’DEN. HERE’S HOW SHE DID IT.

MY CAREER HAS been a series of very unglamorous moments punctuated by a few very good Instagram pictures. I studied engineering in school and then did an MBA. After that, instead of getting jobs, two buddies and I moved to the East Coast because we had been looking for a business idea and learned that the worldwide supply of caviar was down by 95 percent because people had overfished the Caspian Sea. So we built a fishery from scratch, which is everything it sounds like: fishermen and mud. It was the most glamorous product, but I literally carried fish around. We lived in a motel room for months, smelling like fish. It was not what your standard MBA grad was doing, but I wouldn’t be who I am without that experience because I learned that you can figure out how to do anything from the ground up.

Then we went into a giant recession in 2008. There was no way a 22-year-old was going to make it through the worst recession in 70 years by selling the most superfluous luxury product, so I took a real job: I spent a few years as the director of strategy for Sears. But I wanted to go back to being an entrepreneur, so I started a daily-deal site called Buytopia with my partners. We couldn’t raise any money, so we were self-funded for five years while all our competitors raised between $10 million and $30 million and had these incredible ad budgets. Our advertising budget was a bucket of sidewalk chalk that I’d bought. Every night, we’d go to big office buildings in downtown Toronto and write our deal of the day in chalk on the sidewalk outside so people had to step over it in the morning. I kept that bucket in the back of my car for seven years afterwards to remind myself that every time I got to buy an ad, it was a luxury.

I spent a lot of time questioning whether I was cut out to be an entrepreneur. For most of my career, it felt like I was going down, not up. We sold our company to Groupon, and in 2015 I moved to San Francisco with my partner, Andrew. We rented a big apartment to start our company Clearbanc, which funds online businesses, and we had six employees living with us. We stayed in that apartment for two years, and it’s a great success story now, but at the time it was pretty annoying: There’s very little privacy to be had when there is a whiteboard brainstorm meeting going on in your kitchen at night. People underestimate how many moments there are in which it feels like you’re not getting ahead. Fundamentally, though, successful people do what unsuccessful people aren’t willing to do.

My career doesn’t make sense from an industry perspective: I started a coffee shop while I was an undergrad, then I went into fish farming, then daily deals, then e-commerce, then media, then I started a financial-tech company. But all those industries were experiencing a massive amount of growth, so I looked for opportunities. People are often told that they need a certain amount of experience to do something, but you have to reject that notion. You have to trust in your own ability to learn. Spending time trying to eliminate your weaknesses is just not as valuable as trying to sharpen your strengths.

I SPENT A LOT OF TIME QUESTIONING WHETHER I WAS CUT OUT TO BE AN ENTREPRENEUR. FOR MOST OF MY CAREER, IT FELT LIKE I WAS GOING DOWN, NOT UP.

I was a kid in the ’90s, and at that time, the prevailing idea was that to teach kids to be confident, you had to tell them they were great. But that doesn’t build confidence—it builds cockiness. Confidence can only come from doing hard things, having most of them not work out and then eventually having a few wins that are genuine. That gives you assurance that you can show up, fix a deal, fire someone if you need to, hire the right person—all the terrifying things that are essential to your career.

After I lived through my first disaster deal, which was so bad it almost bankrupted the company, I felt nearly invincible. When a key employee quit or there was a terrible shift in the market, I was very calm because I had lived through something much worse.

Honestly, it’s made me a way cooler person because I’ve found a whole other level of resistance and persistence. I’ve seen many different iterations of disaster, and I know there is no substitute for hard work—that’s table stakes. There is no escalator—we all have to take the stairs—and doing whatever it takes to build something isn’t always glamorous, but you’ve got to bet on yourself if you want to sit at the top.