7 Questions with Jacquelyn Cyr

The serial entrepreneur on her new eco-first venture and the importance of happiness over profit

Written by As told to PROFIT Staff

What drives entrepreneurs? What caused them to start their first startup, and what pushes them to keep going? To find out, we ask some of Canada’s most successful serial entrepreneurs 7 Questions.


In this instalment, we talk to Jacquelyn Cyr. Cyr has founded and sold several ventures in the marketing and communications space, the first at 19. She was recognized on the PROFIT/Chatelaine W100 ranking of Canada’s Top Female Entrepreneurs in 2010 and 2011 as CEO of branding agency Espresso.

Last year, Cyr jumped into an entirely new market by co-founding R3VOLVED, a socially-focused enterprise that uses everyday paper and stationery products to educate consumers about the environmental impact of their choices.

As she prepares to debut R3VOLVED’s first collection at Walmart this year, we asked Cyr to explain what makes her entrepreneurial life so rewarding.

Question 1: When did you know you wanted to become an entrepreneur?

JC: I’m not sure if I ever decided it or it is just part of who I am. When I was a kid, my dad volunteered with Junior Achievement. I remember going with him at 11 or 12 to see the older kids starting their businesses, and I thought it seemed so cool. I was the kid starting clubs that raised money, making magazines to sell in the neighbourhood, creating a school fashion show to fundraise for a hospital.

Figuring out how to turn ideas into money has always been a part of me, and I don’t think an opportunity passes where someone shares an idea with me without me thinking, “How could she capitalize on that?”

Question 2: Who is your entrepreneurial role model, and why?

JC: Growing up, my aunt and uncle were always super entrepreneurial, and I found that very intriguing. I didn’t have much exposure to entrepreneurship as a kid in a small one-industry town, so it seemed to me they had turned their ideas into this whole interesting life.

As I came into my own, I had the opportunity to meet so many brilliant and fascinating entrepreneurs. I am most inspired by people who start a business because they love the core idea or product—it’s less about this idea that you are starting a business to make money, though that’s of course that’s core to what business is.

Question 3: What do you know now that you wish you’d known when you started your business?

JC: I started my first company when I was 19 and sold my second business when I was 20. There is a blissful benefit to knowing so little: you are innocent to the things that can go wrong, and naive about how you will be taken advantage of. It makes you more open in how you approach things, and more trusting.

As you develop experience, the painful parts of business make you more careful, which is a double-edged sword. Being an entrepreneur who is focused on new ideas requires that child-like wonder and openness—you have to be so careful not to let the things you learn change who you are.

Question 4: What is the hardest thing you’ve had to do as a business leader?

JC: Manage people, hands down. Every entrepreneur probably answers the question this way, unless they’re HR specialists. I want to be in business to solve a problem or approach a functional issue differently; I didn’t get into business to become a manager.

You have this idea that you can build your company and you’ll hire people and they’ll do the work well and all will sail along. But then you discover that 80% of your time is suddenly being spent in HR: day-to-day management, people conflicts, individual culture misalignments, etc.

It’s important that these issues be managed by someone, but I don’t want it to be me. When so much of my time moves towards internal issues, there is insufficient time being spent on external going-to-market and understanding potential gaps in our product or service offering. I have learned that allowing myself to become that person is a surefire path to frustration and unhappiness.

I think it’s important for an entrepreneur to have a strong, people-centric #2 on their team, who is able to oversee these operational factors so that the entrepreneur’s time can be focused on what they’re best at.

Question 5: How do you prioritize your time?

JC: In addition to my business, I teach and consult and have three young kids and a husband who also like to hang out with me! I have a pretty rigorous approach to what tasks are assigned to what days and time frames.

I split up my types of work and split up the task requirements across each type of work, and then I assign all of these things into time slots. I recently started using this app called Timely to schedule my week, and it is exactly right for how I approach things. Basically, I think of time management like eating well and going to the gym—you don’t always want to do these things, but consistency and discipline have their own rewards.

Question 6: How do you define success?

JC: Success for me is simple: am I happy? I have no interest in spending my days frustrated, resentful, and chasing a fatter bank statement. I want to come up with ideas to solve problems, to help other entrepreneurs who are trying to do the same, and to inspire the next generation to do the same one day. But I also want to be around to see my kids grow up, and to hang out with my extremely funny husband.

My most financially successful year in my last business was also without question the year I felt the least amount of personal success. I was exhausted, never home, and no longer doing the work that I got really charged up about.

Your happiness, ownership of your own day-to-day, and integrity in the choices you make—these are everything. If you’ve got that and you’re able to pay the bills, you are unbelievably fortunate, and should thank your lucky stars every single day that we live in a country where this is even a possibility.

Question 7: What excites you most about your company’s future?

JC: Launching our line this summer at Walmart. It is incredible to me that the biggest retailer in the world feels an alignment with what we’re trying to do. The idea of scaling “green” beyond the elite segment of the market who can afford to spend $10 on a pen is something they’re taking on throughout their business, and I think it’s what will make the idea of sustainability actually sustainable. Our back-to-school program alone is going to divert 300,000 plastic bottles from landfills.

The idea that change can and should be accessible to the average consumer is so powerful, and I am ecstatic to be a part of that shift in mindset.


Have you recently reached a big milestone in your entrepreneurial career? Would you like to answer our 7 Questions? Email us your pitch.

Originally appeared on PROFITguide.com