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In His Shoes: Chris LaBossiere

7-minute read

Who’s walking around in Poppy Barley shoes? Here, we spend 5 minutes with our customers to find out who they are and what they do.


Chris LaBossiere




Co-founder of Yardstick


Edmonton Oxford in Tan

What is Yardstick?

Starting as an Internet application to deliver simple multiple-choice exams, Yardstick has become a global player in providing Professional Examination and eLearning software, psychometric consulting services and eLearning content creation.

Describe your typical day.

Dreaming up ways to grow Yardstick; so I can have the freedom in time and money to make my days not so typical.

What are you most proud of?

Being the “Co-Founder” and a partner in raising two amazing daughters. Even though they are both confident and independent, our daughters are still tolerant and compassionate; good citizens, good teammates, best of friends. Jill and I both can be damn proud of that.

How did you foster your relationships with your kids as you became busier in life - owning a company, investments, politics, etc.

What I gave up in quantity of time with my daughters, I tried to replace with adventure and big-experiences. Since they were 8-years old, I made it a point to have a “Daddy-Daughter” trip each year where we visited parts of the World that spoke to their personal interests and hopefully inspired some wanderlust in them. A 4-day trip to Oxford University and London for a Harry Potter movie premier; or weekend in LA to watch some UCLA college softball. Admittedly outrageous – but meant to inspire my daughters to think big and help in creating a deep connection between us. Also, even though I have been very busy in community work and politics, I hope it inspired them to see the value of service and for them to consider their own way to serve the causes they care about. That said; I am an imperfect father. Luckily for me, they have their mom’s thoughtfulness, steady presence and compassion. In His Shoes: Chris Labossiere wears Poppy Barley made-to-order oxford shoes

Why do you invest in startup companies and when you do, what is it that you're looking for?

Strangely I tend to be a somewhat risk averse when I decide to give my money to others. I am attracted to investments, and entrepreneurs, that are practical about their prospects. Yardstick is my moonshot, because I trust myself to manage the risk associated with it. In other investments, I look for great people, humble and honest about their idea, who hopefully can make some money for us both. That hasn’t always worked out.

You ran for office - how did you transition back to working at Yardstick?

That was really tough. First of all, I was so well supported by my business partners and co-workers; they were selfless in support of my vision of public service. That said, I haven’t worked harder since my return, feeling a bit like I owe it to my team to re-prove my commitment to the Yardstick vision. It helped that I was always very honest and authentic about my passion for good governance, and running for office was consistent with that. Getting our ass kicked in the election was also a perfect way to be reminded that none of us are bigger than an angry group who doesn’t trust its leadership. At Yardstick, as a servant leader, I think of our customers and employees as a group that can ask me to leave at any time if I lose their trust.

You're also a pilot. What's been the best flight of your life? What's the coolest place to fly to from a pilot's perspective?

My business partner Don and I flew our airplane back from the Bahamas. Flying over the Caribbean is absolutely stunning. The “pucker-factor” of commanding a single-engine airplane over the ocean, where landing is not an option, is thrilling. More locally, every flight we take through and over the mountains is a great reminder of why we fly for fun.

We've seen you speak at multiple events and you're very honest and transparent in what you share. What drives your decision to be so visible in the community?

To meet smart, interesting and inspiring people, you have to be willing to throw yourself out there. Being open with your ideas, feelings and experiences – if done authentically – can get you invited into some really amazing conversations, friendships and rooms. I have also always enjoyed the power of straight-talk. Someone giving up their time to listen to one of my ideas or experiences is scary and humbling. It would be a waste of that time to speak in mealy-mouthed bafflegab. In His Shoes: Chris Labossiere wears Poppy Barley made-to-order oxford shoes

What's something that no one knows about you?

I once “borrowed” my grandfather’s truck, drove it 300 km’s without a license, to do something reckless and meaningless. Bringing it back hours late, I made him cry from worry. A decorated war-veteran and my personal hero. It is a massive regret, that I would be so selfish, which still burdens me to this day.

What's the last thing you Googled?

Where to buy a home blood pressure monitor. Important, if not scintillating, for a guy my age.

If you could turn into any animal for a day, what would you pick? What would you do?

I’d like to say dog, but I don’t think any human could know how to love and serve so unconditionally as a dog.

If you could wake up tomorrow having gained any one quality or ability, what would it be? Why?

Some would argue I could learn how to relax, to stop and smell the roses. To not need a home blood-pressure monitor. That.

What's been your experience with Poppy Barley?

My shoes (Edmonton Oxfords) are quite literally the most comfortable I own. A fine shoe for a gentleman is always an investment, and these will provide a return for years to come.

If you could walk in anybody's shoes for a day, who would it be?

I’d give anything to be a foot soldier during WWII, who walked alongside my grandfather and his cohort, to see these 20 something’s save the world and then come back and never talk about it.

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