C-Suite Leadership Series: 20 Questions with Jason Flick

Nov 15, 2018
Jason Flick

Jason Flick, CEO, You.i TV

Quote from the CEO:

“It’s an incredible time to be in the TV industry, with changes happening every day. We’re building the future of TV, and we couldn’t have a better team on board to help us lead this exciting charge.”

–  Jason Flick, CEO, You.i TV


You.i TV builds products that help media and entertainment companies deliver the best experiences for their customers on every screen. The Ottawa-based venture launched their flagship product, You.i Engine, in 2008. As they worked with more and more brands, they realized there was a natural fit between their product and their media and entertainment customers. Why? Well, they’re in the same business: creating amazing experiences. Since then, the firm scaled to help the biggest companies and brands in the industry redefine what’s possible.

We asked CEO Jason Flick some questions to gain insight into the mind of an entrepreneur. Here’s what he had to say:

Top 20 Questions

  1. Your best/worst subject in school?
  • Best: Transport Canada, programming their operations software.
  • Worst: Priming Tobacco.
  1. What was your first job?

I worked through my university degree, so I would not graduate with debt, but my first post-school job was a software developer at Libraxus.

  1. Best advice you ever took?

Get the right people on the bus.

  1. Tip you would share with this years graduating class?

Perspective is everything. Regularly step back and make sure your look at things through the right lens.

  1. What book are you reading?

A Guide to the Good Life: The Ancient Art of Stoic Joy, and the 4% Universe.

  1. Favorite quote?

“What got you here, won’t get you there.”

  1. One thing that surprises you about business?

How much the “mojo” of a business really is what drives success.  We think about business as numbers, process and markets and products, but little of that matters if your people loose faith in what they are doing.

  1. What motivates you?

Doing what I have been told can’t be accomplished.

  1. When was the last time you worked a 40-hour work week?

The first day mobile devices came to market. Plus, I love to mix work, hobbies, and even home life around my “day job”.

  1. What is the best (most recent) feedback you received from one of your employees?

I just went on a listening tour as You.i TV is at a scale point (vs. a growth point) and I wanted to get a broad perspective. I think the most consistent one was the desire for them to have the freedom and time to invest/be proactive in improving what we do.

  1. When are you most productive?

When engaging with a diverse group of people around a complex problem.

  1. Best thing about being a CEO?

Variety and I get to play with all the latest toys from every part of the business.

  1. Most challenging thing about being a CEO?

Making sure everyone is on the same page or you could say has the right perspective.

  1. What is one word that describes your leadership style?


  1. You have ______ in your office?  

You have a MWE LAB Scorpion “chair”, the envy of any geek in your office.

  1. An experience that has influenced you the most as a leader?

Seeing the value of Art and Science (design and software most time for us) working in harmony from start to finish.

  1. A CEO that inspires you?

Richard Brandon

  1. If you weren’t a CEO you would be a ______.


  1. An organization that you always make time for?

Invest Ottawa

  1. Favorite app?


More questions for Jason

Q: The TV and Media industry has gone through many changes since you started You.i TV, what has surprised you the most?

A: How quickly the commoditization of amazing content has become.  We all saw a new business model was coming (DTC) and users wanted a change.  But few saw that Netflix, Amazon, etc could acquire and create world class content so easily.

Q: You have co-founded three companies in your career, what advice would you give new and future entrepreneurs about what it takes to succeed in the early days?

A: Make sure you all align on what success looks like. I see so many start-ups with such potential and they make is past the tough days from “0” to “10”, aka a real business, but then flame out because each founder wants something different.  Life style/hobby company, big exit, IPO, raise VC, go wide/go deep, etc.  Try and align as early as you can on the why and what succees looks like for each of you.

Q: How did you meet your current co-founder and what is unique about your relationship?

A: We met through Flick Software but agreed we were going to building something amazing together and not long after he joined Flick we spun up You.i.  We both connected at the very geeky level of Commodore c-64 emulators.  Stuart, wrote one that is/was amazing, instant respect.

Q: What is a culture defining moment at You.i TV that you are proud of?

A: We said no to a lot of business and stayed true to our focus on the biggest brands that aspired to build the best experiences. Not easy for a bootstrapped company, but we knew if we went down market we could never build the product we wanted to.

Q: What is the coolest thing that an employee has ever done for you? What’s the coolest thing you have every done for an employee?

A: The coolest thing an employee has done is to be brutally honest with me. I think the coolest thing I have done is help an employee get there dream job, even though that meant they would leave You.i TV.

Q: What is your favorite way to celebrate successes with your team?

A: We have our design team create an awesome t-shirt!  Wow do we have a lot of cool custom t-shirts.

Fun fact: Not only is Jason Flick the CEO of an epic Ottawa venture, that also happens to be a scale-up client of Invest Ottawa, he is a director of both the Invest Ottawa and Bayview Yards board!

You.i TV in the news: 

On November 13, 2018, You.I TV announced that the company had secured USD $23 million in growth capital led by Causeway Media Partners. This is the latest of their investment rounds which will fuel expansion of the ski-rocketing venture’s global footprint, developer community, and in re-imagining the ad experience.

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