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What It's Really Like to Launch a Successful Tech Start-Up

In our 9–5 series, we ask our favourite boss babes what a day in the office entails. This week, the Calgary-born Dragon's Den judge and serial entrepreneur Michele Romanow gives us a glimpse into her grind

Michele Romanow co-founder of SnapSaves, head of marketing for Groupon in Chicago and Dragon's Den judge

Michele Romanow, co-founder of SnapSaves, head of marketing for Groupon in Chicago and Dragon’s Den judge (Image courtesy of CBC)

Age: 30

Education: Bachelor of Science in civil engineering and an MBA from Queen’s University

Length of time in current gig: I’ve been an entrepreneur for 10 years, and head of marketing at Groupon since June 2014 when it acquired SnapSaves, the online company I co-founded that gives users cash back on everyday purchases.

Typical hours: All hours.

When do you wake up? I get up at 7 a.m., go for a run and then it probably takes me about half an hour to get ready, get out of the house, and eat an apple on the way to Groupon’s headquarters in Chicago. Even if I’m travelling, my routine stays pretty similar.

What do you usually wear to work? I’m in tech and we always joke that the richest guy is wearing the cheapest T-shirt, so it’s pretty casual. I like to wear a great pair of fitted jeans with a button-down or a T-shirt. I keep a blazer around just in case we have to go to a meeting.

What is the vibe like at your work? It all depends. Sometimes when you have a huge client going live, there’s a lot of rushing around to make sure everything is done but other days everyone’s just working away. Groupon has a super-urban office. Everyone’s on open desks with meeting rooms on the side if you need them. But there are also swings, an enchanted forest, a giant candy pit and, when you walk in, there’s a giant sculpture of a cat in a 9-foot-long spaceship [Groupon’s mascot is Mister Groupon the Cat]. There’s even a place to play ping-pong, if you want to take a break for a second. It’s your fun, open-environment type of tech office combined with people working hard to get things done.

To be an entrepreneur you have to take a lot of risks. What motivates you to take the plunge and pursue new ideas? If you were to ask a skydiver if she’s afraid to jump out of a plane on her 1000th jump, she’d probably say no. Getting comfortable with risk feels a bit like that, you have to take that leap over and over again until it feels like a new normal. A partner also helps. If I hadn’t had Anatoliy Melnichuk [SnapSaves co-founder] believing in everything we were doing, it would have been almost impossible for me to get this far. There were two of us who were crazy and we just kept encouraging each other to keep going.

What’s the best part of your day? I like the part of the day where it’s a bit later, sometimes that’s like 8 p.m., where the distractions and email volume have calmed down and I can just get through the work I’ve been meaning to do.

What’s the worst part of your day? When you have all these unexpected things that break, like sending an email out to millions of users with a link that doesn’t work or if a team member decides to leave. It’s part of the process of being an entrepreneur; you never quite know what’s going to go wrong.

On Dragon’s Den, you get to help finance and support other entrepreneurs. What do you like about that role? Every time I see a pitcher, I see a lot of myself in them. I was on that other side of the table really recently and still am building businesses so I have a lot of empathy for people coming in. A lot of the other Dragons are about the economics, but I think, “How is this person like me and how can I help them?”

When you’re judging, what grabs you about a pitch? To me, it’s always the personality—someone who is passionate and has gone through some level of adversity and figured out how to build something from scratch.

Who is an entrepreneur you admire? Guy Laliberté, the founder of Cirque du Soleil. He was a fire-breather that figured out that if he got a troupe of people together and made a more artistic circus, he could create something amazing. He did not come out of business school he came out of a school of getting things done, and I think it’s just an incredible Canadian success story.

What’s the best career advice you’ve ever received? “If you want to be an entrepreneur, you have to start now.” I got that advice during my undergrad and ended up starting my first business [a zero-consumer-waste coffee shop called The Tea Room] in my second year.

If someone wanted to become an entrepreneur, what qualities do they need? You have to be willing to get up when you’re knocked down 100 times over, and you need to build a team around you that is just as committed as you are.

How do you unwind after work? I have a great group of friends that I talk to and two sisters that I am best friends with—plus I have a wonderful bathtub.

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