Canadian startup founders share what will keep them up at night in 2015

Can't sleep

It’s New Year’s Eve. Everyone else is watching the ball drop and counting down. But something about your business is stuck in your mind – the thing that will keep you up at night in 2015. What is it?
That’s the question we posed to twenty-five startup founders, CEOs, investors, and mentors. The answers were surprising, not only in their diversity, but in their honesty. Take a look at the statements below, and don’t forget to post your own thoughts in the comments section.

A lot of things – but what I really want to focus on in 2015 is uncovering the next breakthrough to keep Vancouver’s tech community thriving. The goal here is to get tomorrow’s young entrepreneurs from the classroom out into the business world, removed of blockers like grades and degrees. Youth around us have great ideas and potential for creating the next big thing – we should reward that ingenuity and help accelerate these ideas into business realities.

– Ryan Holmes, Hootsuite (Founder / CEO)


“I really want people to ask themselves as honestly as possible if they actually made progress in 2014.”

I stay awake worrying that entrepreneurs are spending time working on their venture because they are either too scared to fail or don’t know what they would do otherwise. I really want people to ask themselves as honestly as possible if they actually made progress in 2014, if they are really enjoying what they are doing and what they need to see in 2015 to continue.

– Johnathan Bixby, Koho (co-Founder)

What will keep me up at night? Women’s energies continuing to be diverted into constantly having to prove that they belong and thrive in tech rather than doing the work and building what they are passionate about in technology. This is a huge productivity drain on even top tier talent and we have to turn the corner on this in 2015.

– Saadia Muzaffar, TechGirls Canada (Founder)

I always think about what’s next. What the next technology that will transform the tech industry as we know it, what’s the next platform that will emerge and dominate for the decade to come. There are many candidates, bitcoin / the blockchain, virtual reality, artificial intelligence and machine learning, and few others – a great investor sees the opportunities early (but hopefully not too early)!

– Boris Wertz, Andreessen Horowitz (Board Partner)

It would probably be something like “2014 was crazy, and 2015 will be even more crazy because we have to 3-5x our business again … I think we can do it. Here we go.”

Made me think of something I wrote a while back: “What kept me going was the vested interest that others placed in our success. Friends and advisors had given us their time and lent us their reputation to help us along. Of course, I wanted MappedIn to succeed, but if it didn’t, I didn’t want it to be because I slacked off.”

– Hongwei Liu, MappedIn (co-Founder / CEO)

Marcus Daniels, HIGHLINE
What keeps me up at night is finding the right balance between aggressively going after global growth opportunities and remaining focused on executing well our core business in multiple offices. There’s both a deep ambition to be #1 in certain categories and a real sense of urgency to move faster to win against our well established US competitors in the accelerator landscape. Most players are doing the same thing with very little innovation in the model. That’s simply not good enough for both us and the founders we work with.

– Marcus Daniels, HIGHLINE (co-Founder / CEO)

Revenues, growth and sustainability. These three items are always on my mind and will be my primary focus in 2015 for Launch Academy.

– Ray Walia, Launch Academy (Executive Director)


“This past year, Gamergate misogyny, depressing diversity stats, and female co-founders being erased from startups all kept me up at night.”

This past year, Gamergate misogyny, depressing diversity stats, and female co-founders being erased from startups all kept me up at night. It’s easy to pretend that these things are unique to the US or to the Valley or that they don’t apply to those of us working in tech in Canada. The problem is not that the Valley sucks at diversity; the problem is that the tech industry as a whole sucks at diversity. What keeps me up at night is how much still needs to change in 2015.

– Melissa Shapiro, Wattpad (Head of Global Marketing)

One thing that will keep me up at night in 2015 is how to simplify user experience to make it super easy and delightful for the next wave of our users. Talking to dozens of photographers every week I see important improvements that are key to 500px’s continued success in 2015.

– Evgeny Tchebotarev, 500px (co-Founder)

As a cloud service, we help smaller law firms obtain security services beyond what they can afford on their own. But the weak link in the security chain is users. What can online services do to better help our customers secure themselves and their data? The best encryption and data centers in the world mean nothing when a legal secretary stores their password on a post-it note on their desk.

– Joshua Lenon, Clio (Lawyer in Residence)


“A company at our stage has to grow quickly, and a rate that seemingly overshoots the means we have available.”

People may expect company’s like DreamQii to be worried about the regulatory requirements being defined on the fly by the FAA, Transport Canada, EASA, etc., but for us that is not the main concern. We can roll with those punches.

A company at our stage has to grow quickly, and a rate that seemingly overshoots the means we have available. Growing our team and accelerating our growth is what keeps me awake, in addition to delivering a great product to our first customers. Creating a strong relationship with our early supporters and leveraging that relationship will be key to our growth.

– Klever Freire, DreamQii (Founder / CEO)

What will keep me up at night in 2015? Building the right culture at CareGuide as we double the headcount again.

– John Philip Green, CareGuide (Founder / CEO)

We have unearthed a massive, untapped market at Hubba. There is a much larger opportunity here than we had initially planned. My biggest concern is missing out on the opportunity. We face the same conundrum that all tech founders face: How can we properly balance high growth on one side of the equation while still building a healthy company on the other side of the equation. You need to find the right warp speed where you push the spaceship to its limits without pushing it too hard that it breaks apart.

– Ben Zifkin, Hubba (CEO)

Anisa Mirza
New Year’s Eve is the beginning of a new phase in Giveffect’s expansion, as much of 2015 will be spent adjusting to life in Silicon Valley. From the beginning, we have always been ambitious and reached for the stars when it came to Giveffect. So naturally, we have set some ambitious milestones for 2015. I will be kept up at night just managing this new expansion and hoping we keep on track for this aggressive MRR milestone. Let’s see what happens!

– Anisa Mirza, Giveffect (co-Founder / CEO)


“The part that worries me is that there are so few good advisors (and people that know how to take advice).”

I am excited about the increasing number of good companies that are being founded in Canada. The part that worries me is that there are so few good advisors (and people that know how to take advice) that I think founders are making business decisions that will hurt their trajectory and future success.

What gives me hope is the increasing number of 2nd and 3rd time founders going back at it with a little success under their belt and taking the time to help others.

– Jesse Rodgers, Creative Destruction Lab (Director)

Startups live and die on focus. We’re a company with a big vision — bringing a new identity platform to the world — which makes it all the more important to ensure that our strategy and execution remains focused. I’ll be spending a lot of my time assessing whether we’re focused enough.

– Karl Martin, Nymi (CEO)

We’re anticipating major growth as we usher our new platform to market in 2015. What keeps us up at night is our ability to provide the highest level of support to our growing customer base, to stay up-to-date on the ever-changing big data technology landscape and to ensure we continue to deliver 10x better performance than our competitors.

– Alkarim Nasser, Gallop Labs (co-Founder)

Execution – Over our first year and a half, we attracted an amazingly talented team and funding (time) to build a platform to help smaller retailers, the ones using commerce platforms like Magento, Bigcommerce, and Shopify, with the powerful data driven marketing capabilities traditionally available only to the largest and most sophisticated merchants. But now, as we launch those features, we need to actually get out there and show people what predictive analytics, machine learning and marketing automation can do for them!

– Aran Hamilton, Vantage Analytics (co-Founder / President)

2015 will be a year of optimism for technology and startups. In Canada, what I’m worried about is if we don’t take enough risk, and if we don’t take it quickly enough.

– William Mougayar, Startup Management (Investor)

Great question… simple answer, hiring best of breed to keep up with unbelievable growth opportunities for Horizn in 2015.

– Janice Diner, Horizn (CEO)


“This is a crucial stage for any startup, where you reach escape velocity or you don’t.”

2015 is about acceleration for LEAGUE – building momentum with each and every foundational week. This is a crucial stage for any startup, where you reach escape velocity or you don’t. All this in a very turbulent global market and political environment, oil plummeting and talks of tech bubbles. 2015 won’t be a year for sleep.

– Mike Serbinis, LEAGUE (Founder / CEO)

Mike McDerment FreshBooks-ceo
Technology stocks have led a great run in the capital markets. Things are poised for that to continue headed into 2015, but the only thing we can count on in life is change. So… I’ll be watching the capital markets closely because they are relevant as we build FreshBooks into global technology leader headquartered in Toronto, and because the Toronto startup ecosystem is doing so well, and strong capital markets will make maintaining that momentum much easier.

– Mike McDerment, FreshBooks (co-Founder / CEO)

  1. Sales/Traction. The constant worry of any startup.
  2. Funding – with talk of a funding bubble and some of the highest levels of VC funding in years, will 2015 show a return to tougher times in finding great funding partners for startups? Will U.S. investors retrench back into their home markets if credit starts to tighten causing further trouble for Canadian startups?

– Mike Kirkup, Velocity (Director)

What keeps me up at night? Finding the best talent. We’re hiring!

– Malgosia Green, CPO, Top Hat

I will be thinking a lot about the implications of mobility in 2015. The rabid advance of mobile technologies will have a significant impact on many businesses, but the implications are less apparent in crowdsourced advisory services like ours. I suspect the most likely entry point will be on the supply side: enabling more efficient expert connections, and making the expert experience more enjoyable. This is certainly part of where we’ll focus our efforts in the New Year.

– Douglas Cole, 10EQS (Managing Director)



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