Vote Now for Startup of the Year in the Canadian Startup Awards

A mobile workspace company, a teaching app, and a recently acquired food delivery service are among the three finalists in the Startup of the Year category for the Canadian Startup Awards, which recognizes the year’s “most exceptional startup.”

Below (in alphabetical order) is a look at how each company beat the extreme odds of becoming a successful startup:


Montreal-based Breather was founded in 2012 by Julien Smith and Caterina Rizzi as a way to connect people to workspaces through a mobile app. Breather launched in New York in 2014, and opened its first locations in San Francisco and Boston soon after. It currently has more than 350 locations in 10 cities around the world including, Toronto, Los Angeles, Chicago, and London, UK. Some of its customers include Google, Apple, Facebook, BuzzFeed, and Uber among others.

Here, Smith talks about the company’s beginnings and its growth to date.

TV: Every good startup has a story about how it came together. What’s yours?

JS: Breather was born after countless business trips where early checkouts, distracting coworkers and noisy coffee shops were putting a dent in my productivity. I felt there was a need in the marketplace for workers like me to have a quiet place to focus and get work done.

I enlisted my friend Caterina Rizzi, who has a background in fashion and retail, to design each space, giving it a unique look and feel that would set it apart from the competition. Over time, we realized there was a massive need and interest from larger groups. We’ve since focused on adding larger spaces fit for entire teams to our network.

What problem are you trying to solve?

We offer well-designed workspaces in a variety of sizes, for individual work or for large teams. Breather users are a highly diverse and range from individuals who book our locations for meetings and client presentations to organizations such as Apple and Levi’s, who reserve Breather spaces for offsites or team workshops.

Startups often use us as a space solution, teaching companies host classes and workshops in our spaces and production companies reserve Breather locations for a photo or video shoot.

Who was your first investor?

Real Ventures, for our seed round.

What money have you raised since then?

We announced our latest round of funding in early December, when we closed $40 million in funding, bringing our total funding to $73 million to date. This Series C round was led by Menlo Ventures, the venture capital firm behind Uber, Tumblr, Warby Parker and Siri.

The financing included follow-on investments from Valar Ventures, RRE Ventures, Slow Ventures, and Real Ventures, and follows a Series B in 2015 and a Series A round in 2014. The investment positions Breather as the most well-funded startup in the growing on-demand workspace sector.

What’s your biggest success to date?

There are a few milestones we’re proud of, but our recent Series C raise is the one that stands out. Raising $40 million allows us to continue to build on our existing success while allowing us to grow into ways we hadn’t previously thought possible.

In addition, the support and mentorship from our investors at Menlo Ventures, and specifically Venky Ganesan, who joined our board, has been an incredible valuable.

What’s next for your company?

We focus on customer experience, which defines the pace we grow at. Ultimately, we seek to have a Breather space in all major cities across the world, provided we can deliver on our promise of providing a consistent and seamless experience.

Our business will grow wherever people make a living doing what they love, whether that’s in a high-density city like Tokyo or in smaller, dynamic cities where they can build something great. Our dependable experience is something we want users to be able to rely on no matter where work and life takes them.


SkipTheDishes was founded by brothers Josh and Chris Simair in 2013 after they saw the success of Just Eat. Three years later, the company was bought by Just Eat and dubbed one of the biggest exits of a Canadian startup in 2016. SkipTheDishes describes itself as a North American tech company that connects people to local restaurants and food couriers.

Here, cofounder and CEO Josh Simair talks about the brand’s beginnings and what’s next, post exit:

TV: Every good startup has a story about how it came together. What’s yours?

JS: We grew up in the Prairies. Like many people from our region, we moved away to big cities to pursue exciting careers. We observed how people in London and New York used food delivery as a means to gain more time in their day to focus on what’s important to them. In lower density areas it was usually only pizza and Chinese food that offered delivery.

We thought that all of our cities deserved delivery. We soon found out we had to take a completely different approach to make food delivery work in our cities.

What problem are you trying to solve?

Food delivery seems straightforward, but doing it at scale with sustainable margins has proven elusive to many companies around the world. We’ve built dozens of back-end tech systems to enable delivery in both high and low-density regions around the world.

How is that going?

It’s going well. Of course, with all the complexities of working with restaurants and driving around cities, there is never going to be perfection. Our tech, systems, and team work with our network to prevent errors before they happen. Today Skip is available in 25 cities in Canada and the U.S. Midwest. We’re growing quickly.

Who was your first investor? 

We bootstrapped, so technically the founders funded Skip with our savings and with debt.

What money have you raised since then?

Golden Venture Partners led our first round about three years after we were founded.

A few other great VCs joined in: Founder Collective, Felicis, and FJ Labs.

Angels include David Segal (David’s Tea), Harley Finkelstein and Tobi Lutke (Shopify), Dan Debow (Rypple /, Allen and Eva Lau (Wattpad / Two Small Fish Ventures), Scott Belsky (Behance), and Fabrice Grinda.

What’s your biggest success to date?

From day one, we knew we’d need a team of honest, dedicated, and high-performance people. They have helped build our network sustainably, and remotely onboard and integrate our systems with tens of thousands of restaurants and couriers. Therefore, building Skip in Winnipeg and Saskatoon made perfect sense to us. Our friends in Toronto and Vancouver are often confused by this. “I didn’t know you had engineering schools out there” is a typical statement made by our close friends in Toronto.

What a lot of the world didn’t realize is that we have amazing people who want to live in the prairies. By embracing our region’s strengths (dedication, talent, low costs) and being mindful of our weaknesses (low-hype, less aggressiveness, not promotional), we’ve exploited many unfair advantages we have over startups based in the Bay Area or New York.  We believe that Canadians have great strengths all across our country and we’re working tirelessly to keep putting the Prairies on the tech map.

What’s next for your company?

While it’s business as usual for Skip, we have an opportunity to continue building the future of food delivery with Just-Eat, the world’s leading food delivery marketplace. It’s tremendously exciting.

These days we’re spending nearly all of our time interviewing and selecting top talent to join our Winnipeg and Saskatoon management teams. We’re currently bringing in people from all provinces and many countries to join us in Winnipeg and Saskatoon.

Top Hat

Toronto-based Top Hat is a teaching platform that helps professors keep their students awake and engaged during class. It includes games, quizzes, polls and interactive demonstrations that teachers can use in their lectures, as well as a platform where profs can collaborate on course material.

Here, cofounder and CEO Mike Silagadze about how the technology enables teachers to inspire students—and each other:

TV: Every good startup has a story about how it came together. What’s yours?

MS: Top Hat was born out of my experience studying engineering at the University of Waterloo. The traditional lecture model, and course delivery in general, felt totally out of touch with the rest of the world. Outside the classroom, learning was interactive and engaging—there were myriad resources and tools available. But when you showed up to the classroom, it felt like going back in time. The rest of the world had drastically changed with technology, but the university experience felt like an anachronism.

Of course, I wasn’t the only one to make this observation. Arguably most students have felt that way for the last 20 years. But there wasn’t much that could be done about it until smartphones came on the scene. In 2010, barely 10 per cent of students owned smartphones, but it was clear to me that they would soon become ubiquitous.

I believed that this presented a remarkable opportunity: to transform the passive, didactic lecture experience into something active and engaging by incorporating the very technology students were already bringing into the classroom. And as smartphone use grew exponentially, word spread about Top Hat, and our customers multiplied like crazy.

What problem are you trying to solve?

Ultimately the goal is to help make education better. The current educational experience in universities is out of touch with today’s students, and as a result they’re disengaged and they’re not succeeding. The graduation rate among university students is less than 50 per cent across North America—that’s staggering!

Most students are going to university and ending up with nothing but a pile of debt to show for it. In addition to that, students are paying between $200 and $300 per textbook—the price has risen over 1,000 per cent over the last 30 years. Top Hat helps students save money on their textbooks and helps them learn more effectively, increasing graduation rates.

How is that going?

Extraordinarily well. Top Hat is now at 75 per cent of the top 1,000 leading colleges and universities in North America with millions of students using our teaching platform, and the company is doubling in size every year.

Who was your first investor?

We secured $200,000 from two angel investors in mid 2010. We followed that will a series A funding worth $6 million in 2012 with investors like Emergence Capital, iNovia Capital, Golden Venture Partners, Version One Ventures and SoftTech VC.

What money have you raised since then?

We’ve raised $17 million between VC rounds and angel funding. (Update to Top Hat’s funding here.

What is your biggest success to date?

I’m really proud of the awesome team and the dynamic culture that we’ve built. Recruiting for tech companies in Canada is incredibly competitive and we’ve attracted top talent—an innovative, creative and hardworking group. I believe it’s because people buy into the Top Hat vision of improving education and helping students and teachers be more successful.

What’s next for your company?

We’re aggressively expanding into academic content, creating and distributing interactive materials that will finally provide a viable alternative to overpriced textbooks. And we’re growing like crazy. In 2016 alone the company expanded from 90 to more than 200 employees across offices in Toronto and Denver. This year we’re moving into a bigger head office in downtown Toronto, and we’re still hiring!

Choose Your Favourite

Which of these deserving young companies deserve to win in the Enterprise Transformation category? Make sure you vote for your favourites before Feb. 19 at midnight to have your say in which startups should win in their respective categories.

The winners will be announced at a live gala on March 2nd at Steam Whistle Brewery in Toronto.

As Software Eats World, Three Startups Show Hardware Still Haute