The Chapters/Indigo CEO Entrepreneur's Quiz: What to Ask Yourself Before You Start

So back in November, we wanted to have Heather ReismanCEO & founder of Chapters-Indigo books and Music, speak at the Legacy Conference (**hint hint, nudge nudge, early bird ticket price ends in February**). So we cold-emailed her, crossed our fingers and hoped for the best, since after all, Heather is......

One of Canada's most recognized businesswomen (Women of Influence)

Heather Reisman.jpg

Annnnd we got this back in our inbox;

*sad face*

*sad face*


So then, we replied to Heather similar to the following:

'Heather, it's unfortunate you can't make it to Ottawa, for Canada's largest student led entrepreneurship conference on April 1st-2nd...

We still have so many questions to ask, like what's the future of Chapters and Indigo with e-readers? What advice would you give a student entrepreneur if she walked into your office? What are you most proud of?

For example, what are your favorite books for entrepreneurs?'

Heather is, in fact, everything we thought she was and more. Even with her wildly busy schedule, she got back to us and had quite a lot to say:

  • What it takes to be an entrepreneur
  • Where her business (the biggest bookstores) will be in 5 years, &
  • What she holds dearest to her heart.

Heather's thoughts:

If you've been following along so far, you know we wouldn't have dared not asked for Heather's thoughts about...


... is process of being in school permanently, in the end it’s about figuring out how to inspire others toward some shared vision. While at the same time, inspiring others to achieve their own dreams. It’s that balance, trying to move together towards something. BUT you can only do that if individually, people feel like they’re doing what they want to do."



... is like breathing, it’s everywhere and therefore as a CEO the responsibility to understand it, engage with it, know how to resource it, both from a people point of view and from a financial point of view, it’s our job. It’s the other side of people management. "

*whoa, whoa*

"Entrepreneurship... the most joyful, exciting, empowering, and creative way to work.

And before you judge us.... yes, we did ask the typical:

Where do you see yourself
in 5 years?

Why? Because we're curious (and we know you are too) about the future of a bookstore in a world of ebooks.

Heather's answer:

"I fully expect, if I am fortunate with my health, I will still be CEO of Indigo 5 years from now.  We have big ambitions for this brand – taking it beyond Canada's borders - always remaining true to our Canadian roots and to writers, books, culture makers.  Our mission is to enrich the lives of our customers – what could be more energizing than that."

Here's an ARTICLE that covers more about the future of books. Featuring, of course, Heather.

You now get an idea of Heather's achievements, 
*time to get personal*

What does one of Canada's
"100 most powerful women" value the most?

"The warmth and closeness of my family.  Family has always been the central most value in my life and one which I intuitively knew would be my true anchor.  

This is not to say that there were not times when I felt stretched, or even torn, between family and work.

 Fortunately for me – being an entrepreneur meant I could for the most part manage my schedule to achieve a level of balance that worked for me.  

And... perhaps I took longer to achieve some things than others might have but for me the trade offs in favour of family were absolutely the right ones."

"I am a huge believer that woman who choose to have exciting careers and rich family life can do so – but only if we see life over a long arc and we make some short term trade offs to ensure the family life we want. "

A message to all you entrepreneurs:

"I want to convince you that these kinds of personal explanations of success don't work. People don't rise from nothing... It is only by asking where they are from that we can unravel the logic behind who succeeds and who doesn't"
― Malcolm GladwellOutliers: The Story of Success

Heather's soft spot for family is definitely a boost.


It's demanding, entrepreneurship is demanding...the good kind of demanding. Think you have what it takes? Heather thinks you should be able to confidently answer the following questions in the affirmative:

*It's time for a little self interrogation*

- DO YOU have an idea you feel so passionate about you simply have to do it?

- DO YOU have at least one person in your corner - family, friend, partner, who fully believes in you and will always "be there", as a sounding board and support person? Someone who will be effectively challenging you when necessary? Mostly, someone who will happily listen to you talk about your ideas a lot?

- DO YOU see yourself as being resilient - able to withstand some moments of rejecting, some failure, and some disappointment? It is inevitable on the way to entrepreneurial success (see the movie JOY ft Jennifer Laurence  to fully understand this). 

- DO YOU have at least enough financial resources to see yourself through the cost of a start up - both to support yourself and to fund what is essential in the business?

- DO YOU fully understand that people become entrepreneurs not because they want to make a lot of money but rather because they are driven to create something? That is key. Really key

So, do you?

(Have what it takes)



(How we feel about this...)

Keep those questions in mind! 

They're your keys to success - no one makes it on their own. 

Lastly, we'd be absolutely nuts if we didn't ask...


heather's picks for entrepreneurs

Steve Jobs Walter Isaacson

Pour Your Heart Into It - Howard Schultz

Creativity Ed Catmult



** Heather can't make it to the Legacy Conference on April 1st-2nd, but hey - we know you probably can. So with that in mind, we'll just leave this right here for you: