Collision Conference 2019: Five Insights for Founders, First Employees, and Freelancers

Collision Conference 2019, Canada’s biggest business and technology conference, made worlds collide as its 25,000 delegates took over Toronto last week. With the speaker lineup consisting of the Canadian Prime Minister, A-list actors like Seth Rogen and Joseph Gordon Levitt, music artists/professional athletes like Akon, Timbaland, and Terrell Owens, and finally, billionaire dollar company founders from Twitter/Medium, Mailchimp, Hootsuite, Oculus Rift, Shopify, and Houzz, it was apparent to many of the delegates that the networking and insights would be well worth the four-figure ticket cost.

I was lucky enough to be invited a few days before the conference started and had the fortune to immerse myself in it and document the biggest insights for founders, first employees, and freelancers - those who depend on hunting new business and mining the insights necessary to take their visions and people to the next level

1. Speed matters near the end, not the start

While most of us know by now that overnight successes are a myth, Collisions’ most profound speakers and rising companies drilled this point home with great data and stories. Local Toronto startup founder, Ray Reddy from Ritual, emphasized how “speed matters near the end, not the start.” His food pickup app took two years to open two cities before turning on the tap to open 10 cities in just about the same amount of time. They obsessed around getting the product and go-to-market plan right before duplicating it. One of the rare unicorns around today which hasn’t taken a penny of venture capital is Mailchimp, which has been an 18-year old success story. Their exuberant founder, Ben Chestnut, spoke to being very focused on owning email marketing for years before recently going into turbo mode and launching their all-in-one marketing platform.

2. Team productivity and wellness matter

As mental health and the need for greater productivity become bigger realities to today’s workforce, there were some great points around how to balance this out. Mathilde Collin, founder of Front (recently raised $66M last year), spoke to how in every employee onboarding she tells staff that at the end of the day, Front is just a job and it’s never worth sacrificing wellbeing for it. Getting personal at one on one staff check ins is also crucial and it’s a reason why even Google’s most important executives still kick off meetings with weekend and travel updates to build empathy and rapport in the room before heated debates ensue. For productivity, Mathilde spoke about deleting the Slack app on weekends and booking deep work time and meditation on certain mornings and weekends where the most important thinking time can be spent with limited stress. Most of the hacks and habits mentioned on all panels speaking to productivity and wellness are covered in ex-Google Ventures veteran, Jake Knapp in his latest book, Make Time.

3. Figure out your “why now”

Mike Maples, founder of Floodgate Capital was easily the most insightful investor of the conference as he unloaded wisdom that he has gleaned from his early investments in Twitter,, Weebly, and others. He emphasized that most global companies ride a wave rather than create one. They look at recent world forces that might act in their favour, such as technology leaps (think 5G, AR/VR), customer adoption (sharing economy, delivery), government policies (GDPR, immigration policies), and new industries/business models that have been validated. Boasting about the brilliance of an idea or capabilities of a founder is rarely enough to grow exponentially.

Traits of founders he did emphasize were crucial supplements to the “why now” question are having crazy passion in what you do. So much passion that when asked if you would still be running the startup you run now if it was the only one you were allowed to run, you would not blink to say yes.

4. Leverage but also be wary of Canada’s growing tech ecosystem

Justin Trudeau kicked off Collision conference with a fireside chat where he addressed why entrepreneurs should build their companies in Canada. “As we see anxieties and worries around the world, Canadians know that we get more resilient communities, we get better solutions, we get better innovations, when we bring in people from all around the world.”

He correctly attributed Canada’s advantages to open immigration policies and government grants and education. I have had firsthand experience with the latter and have created a Canadian Grant Guide.

Ironically, on the very last panel of the conference, Ryan Holmes from Hootsuite and Ba Blackstock from Bitmoji shed light on the shortcomings of Canada. While recently the Canadian doors are especially open for talent to relocate, it’s still very difficult to find them. A big reason is that Canadian companies simply don’t pay enough even though the quality of life is far greater than in most places. This reality has opened the door for companies like Vanhack to focus on international senior developer talent recruitment to Canada companies.

Another point to consider is that Canada’s conservative nature makes it hard for startups to find early adopter customers within close proximity compared to the advantage they would have building south of the border. Especially if you run a high-ticket item business where proximity to customers is especially appreciated by them, sales are much slower than they should be. Budgets are also much smaller and it takes far longer for decisions to be made. Customer proximity, fast decision making, and bigger budgets (not to mention the currency advantage) are reasons why most Canadian tech company success stories come from building for the U.S and a global audience rather than starting in their backyard.

5. Connect deeply and be a connector

I do a lot of networking. I have both created and been part of various events but this one made me feel like I was taking my first steps as an infant - it was next level. What I thought was decent preparation wasn’t even close and as the three and a half days of the conference evolved I started to pick up on things. Ultimately, I realized how important it is to speak to people as humans and not as transactions. Starting off conversations by asking what someone thought of the last speaker or what brought someone to the conference were crucial to start things off authentically.

Asking whom someone is looking to meet is a great way to add immediate value as you'll start to connect dots quickly and give more value to the conference as a whole. You must believe deeply in the long game with relationships and even if you want to do business with someone, always look to how you can connect them with someone else in your network who might be more relevant to find common ground with today.

MaRS Discovery District nicely covers the basics of how you should approach a conference of this caliber. It’s all about getting out of your comfort zone, knowing how to give your ask and elevator pitch at the right moment, going in with a plan, and making meaningful connections - go to all the night events even if you need to catch up on sleep all of next week.

I want to close out with what co-founder of Intercom, Des Traynor, emphasized. His whole presentation was about retaining relationships with customers or people you meet at conferences. He spoke to putting in the effort early to serve others before you serve your balance sheet.

Great things take time and effort. There are no shortcuts. This is why we need to be focusing on something we believe is a game-changer and ensure it’s around the right people whom we plan to collide with for decades to come.

Collision crystallized the importance of building the right things at the right time, slow and steady, and with the right healthy and productive people.

To get me for a one on one to dive deeper into how the above topics apply to your business endeavours, visit my website: