20 Questions

This Work-Life Balance Strategy Helped This Entrepreneur Create a Business That Reaches Millions of Business Owners Across the World

Freshbooks CEO and co-founder Michael McDerment reveals the approach that helps him grow as a leader.
This Work-Life Balance Strategy Helped This Entrepreneur Create a Business That Reaches Millions of Business Owners Across the World
Image credit: Freshbooks
Entrepreneur Staff
Staff Writer. Covers leadership, media, technology and culture.
9 min read

Editor's Note: Entrepreneur's "20 Questions" series features both established and up-and-coming entrepreneurs and asks them a number of questions about what makes them tick, their everyday success strategies and advice for aspiring founders.

Even if you have a strong sense for business in your industry, not everyone is a bookkeeping wizard, and that’s where Freshbooks CEO and co-founder Michael McDerment wants to help.

Fifteen years ago, McDerment was a small-business owner, running a design agency with three employees. His least favorite part was billing clients, because it meant hours on end in the weeds with Excel and Word documents that could easily be lost or deleted. Fed up with a system that was barely working, he decided to take matters into his own hands. He coded the software that would become Freshbooks.

With his co-founders, he pivoted away from design and client services to see what this new idea could be and began operating out of his Toronto basement.

Today, as CEO, McDerment oversees a company that employs more than 200 people and serves over 10 million people to date in more than 120 countries.

We caught up with McDerment to ask him 20 Questions and find out what makes him tick.

1. How do you start your day?
Every day I practice yoga, but sometimes I'm up because the kids woke me up versus me getting up before them. My best productive and effective days are when I have an hour of quiet before the world [wakes up]. It's basically about accessing a vaster mental landscape before the the busyness of the day starts to catch up with you. I started the yoga because I had some difficulties with my back, but now I just like it to make sure I get at least 25 minutes of quality exercise every day.

2. How do you end your day?
I read every night before I got sleep. I do it on paper. I find that staring at the screen does not help me sleep. I don't look at my phone generally after 9 p.m. I'll read from 10:30 p.m. to 11 p.m. That's my wind down routine at the end of the day and seeking reading books on paper.

3. What’s a book that changed your mind and why?
A book by Simon Sinek called Leaders Eat Last. What I like about it is he's done a nice job of [distilling] a very nebulous topic of what makes a great leader. I recommend it for anybody who cares about leadership or culture or frankly just being a better human being and understanding society and even stuff like why people hate people who are famous for being famous.

Related: The Young Founder of This Celebrity-Loved Activewear Company Shares Why You Should Always Trust Your Instincts

4. What’s a book that changed your mind and why?
For entrepreneurs [just getting started], I like E-Myth by Michael Gerber. It does a good job talking about the fundamental capabilities you need and the complementary skill sets and people types of the manager, the technician and the entrepreneur and how those can all live in one person.

5. What’s a strategy to keep focused?
My job these days is to largely attend a lot of meetings. I don't have a lot of time to myself. When I do I get interrupted every three minutes. So my strategy for maintaining energy and focus starts before I show up at the office. Those days when I get up before everybody else, get some exercise and practice yoga, helps me in meetings to stay dialed in and have a still mind. Those are the days when I'm at my best.

6. When you were a kid what did you want to be when you grew up?
I never [knew what I wanted to be when I grew up] and that made for a painful set of years in my 20s. But I always had energy in the direction [of entrepreneurship] and I wound up in a very good place for me.

7. What did you learn from the worst boss you ever had?
I never had one, but I've [realized as an entrepreneur] that you never stop learning how to be a good boss.

8. Who has influenced you most when it comes to how you approach your work?
[In terms of] dialing in on some really good values and customer focus, one of the founders of Rackspace, Pat Condon, is probably the biggest single influence on me as an entrepreneur.

Related: How the Entrepreneurs Behind Text-Based Wellness Brand Shine Find the Biggest Opportunity in Everything They Do

9. What’s a trip that changed you?
When I was 14 years old I did a 36-day canoe trip. When we do things like that, we start to learn [the feeling of "I can't"] is all in your head, and if you persevere and are surrounded with good people you can accomplish anything.

10. What inspires you?
You need to find different things at different times. Books, knowledge learning, all that is generally a source of inspiration and regeneration for me. Music and physical activity are also how I recharge and find inspiration.

11. What was your first business idea and what did you do with it?
In grade two I designed a video game for parent teacher night. I put it up on that chalkboard and asked the parents, who wanted to buy a copy? It was one of those early indications that I was on an entrepreneurial path.

12. What was an early job that taught you something important or useful?
My design agency where I was doing client service work. Today, I run a software business. It's invaluable to know that there's an individual on the other side of that software. I talk with customers all the time. I think that customer focus and frankly the infinite number of ways customers are just interesting in and of themselves as a source of inspiration. I love helping people solve their problems and I learned that with the client service business.

13. What’s the best advice you ever took?
To be successful on business -- and I would argue life -- you only need two things: shared values and alignment. If you have those two things you can go a long way.

14. What’s the worst advice you’ve ever been given?
Some of the worst advice I got was from people telling us how we had to build our business. One example was, I met a very senior businessperson who told us we would never succeed unless we did things a certain way. That individual was wrong. Some of the worst advice is when people are very prescriptive about how you should run your business.

15. What’s a productivity tip you swear by?
Yoga, every morning.

Related: Pinterest Co-Founder Shares the Simple Step He Took to Transform His Communication Style

16. Is there an app or tool you use in a surprising way to get things done or stay on track?
I carry a Moleskine notebook and a ballpoint pen with me everywhere. I've learned to write things down to get them out of my head, which frees up my head so I can be more effective.

17. What does work-life balance mean to you?
The goal is to never work a day in your life and if you want to feel that way, you've got to remember that it's a marathon, not a sprint. It's about managing your energy so that when you need to pour it on for a sustained period of time you've built up the reserves and then when you can let things up, you make time for yourself and your family. I don't think it's about consistency.

There's an element of discipline and consistency every day, but it's a more macro thing. Sometimes you're going to build up some credit. And sometimes you're going to go into debt. [You need] to accept that. Know that those periods where you go really deep into debt are actually often periods of great personal growth and challenge and learning about yourself and your ability to persist. But it's important to recognize that you can't do that all the time.

18. How do you prevent burnout?
I turn my phone off every Friday night at 7 p.m. and I turn it back on around 7 p.m. on Sunday. I get 48 hours to sort of recharge every week and that has been the key for me. Most days I try to have breakfast and dinner with my kids.

19. When you’re faced with a creativity block, what’s your strategy to get innovating?
Go for a long walk or run, some kind of physical exertion. And I will stop working. I will make sure that night, instead of not looking my phone at my phone from 9 p.m., I'll not look at it from 6 p.m. on. Just get space from my inbox and let my brain percolate and sift through things so you can get to a place where we can get inspired and creative again.

20. What are you learning now? Why is that important?
I'm learning about how to get to my next level of time management and trying to focus on having a 80 percent or more of my time focused on things that are only on things that are going to impact things 18 months and beyond from where I'm at today. I'm learning how to do that and sustain it versus getting dragged into the day to day.

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This Entrepreneur Shares The Focus Strategy That Helped Him Build an App Used by Millions