Q&A series: Jeff Speak (Chairman at Cimpl, Dobson Cup judge)

Editor’s Note: Jeff Speak has been a judge during the McGill Dobson Cup and a supporter of the McGill Dobson Centre since the beginning. He’s a serial entrepreneur who has founded and built 4 successful technology businesses to date. Cimpl is his current focus which is Canada’s leader in telecom and IT expense management, and consistently recognized as a Canadian Top 50 Employer in Canada.

Jeff received his graduate training in accounting from McGill University and has further certifications from the London School of Business and Harvard University.

I didn’t understand the importance of a mentor in university but now, every idea I have I validate through these people.

Jeff Speak (bottom right) was a Dobson Cup judge during the Finals, alongside the likes of Rubin Gruber, Steven Kokinos, and Luce Veilleux.

Q: Who are the people that you hang out with most and what impact have they had on you?

A: I didn’t understand the importance of that or even know what a mentor was in university, but now I have them. Every idea I have I validate through these people.

1. I have a very close mentor who’s invested in every business I’ve ever been in – really, he’s invested in me. Everything I do, he has skin in the game. But more importantly, it’s a friendship, and it’s all about sharing knowledge. He’s a very successful person and he’s shared a lot of ideas with me and pushed me to further my education after university because learning constantly is crucial. 

2. I’m also a part of this global organization called YPO (Young Presidents Association), which is centered around creating better leaders through education and idea exchange. So we all get together once a month and talk. You can be completely honest: you can say you’re scared, that you don’t know what you’re doing, or ask for advice about your situation. There’s no pressure, there’s nothing to gain from presenting yourself as something you’re not – you just want the best for each other.

3. And of course, my wife. She’s my partner in life. She’s a surgeon, which has nothing to do with business, but we communicate: I know everything about her surgeries, and she knows everything about my businesses. She knows me because she’s been listening to me for 30 years, and so she knows how to steer me in the right direction and tell me what I need to hear.


Q: Do you remember a significant scene from your past that has impacted who you’ve become?

A: Along your life’s trajectory there are these little stars – people intervene. Someone takes you aside and tells you they see something in you. A few teachers from Loyola High School did that for me. One of them told me they saw an entrepreneur in me. I look at those kinds of moments, and I’m grateful they did that because without them telling me that I might never have known it myself. 

When I was younger, I had a bigger ego and didn’t think I had to listen to anyone. As I’ve gotten older, the definition of wisdom to me is the ability to listen.

The McGill Dobson Cup, powered by National Bank and hosted by the McGill Dobson Centre for Entrepreneurship, is McGill’s flagship annual startup competition.

Q: What would you like to see more of in the business world? This could be an approach, an industry, or anything else.

A: I’d like to see more women in leadership positions. We’re fighting that battle brick by brick now, and we’re definitely going to see a better world and better business outcomes if we can make it happen. If you look at the workforce it may seem 50/50, but if you look at upper management it’s not even close – that has to be rebalanced.


Q: What’s your go-to system for decision-making and execution?

A: Listening. When I was younger, I had a bigger ego and didn’t think I had to listen to anyone. As I’ve gotten older, the definition of wisdom to me is the ability to listen. You become wiser when you don’t talk. By listening, you can get more data points to help you make your decisions.


Q: How have you continued your learning after college?

A: Reading. I specifically like biographies about businesspeople, politicians, athletes, and leaders. I prefer real stories about the challenges people faced as opposed to business theory. 

Editor’s note: Here are some biographies you can get started on.

Mo Akif

Mo Akif

The Editor-in-Chief of the McGill Dobson Chronicles. Never having started a lemonade stand as a child and tired of reading blog posts about entrepreneurship without actually doing anything, he was on the verge of giving up and joining a pyramid scheme. Luckily the McGill Dobson Centre decided to adopt him, allowing him to get a closer look at what it takes to build something valuable.