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I’m back from Startup Weekend


I usually write on Architect This City every day. But this past weekend I skipped both Saturday and Sunday, which is something I haven’t done in the 15 months that I’ve been writing this blog. I hate missing days. I really do. But I had no choice. I was at Startup Weekend here in Toronto.

For those of you unfamiliar with the global Startup Weekend initiative, let me tell you how it works.

Last Friday night, hundreds of people from Toronto’s startup community convened at the MakeWorks coworking space in Toronto’s west end to pitch and hear new business ideas. The floor is always open to anyone who would like to pitch, but you only have 60 seconds (hard stop) to convince the crowd that your idea is worth pursuing. This past weekend there were about 40 pitches.

Following the pitches, the crowd then gets to vote on their favorite ideas. The top pitches – there were 13 selected this past weekend – get to move on and the people who delivered those pitches become team leaders. They are then asked to get up one more time to tell the crowd who they need to develop their idea over the weekend. Once that happens, everyone starts scrambling around to try and put together a team. It’s all about hustle.

Immediately after the teams are formed, the work starts.

By Sunday at 5pm, you’re expected to have validated your idea and problem in front of real people, executed on some sort of minimum viable product (the solution), and ideally brought in some of your initial customers. Because at the end of the weekend, all the teams get up and deliver a 5 minute pitch in front of a panel of judges who assess you on how well you did against those 3 objectives.

It’s a weekend of raw adrenaline. I wouldn’t be surprised if I lost about 5-10 pounds as a result of how little food I ate and how much coffee I consumed.

I pitched a real estate related idea – just like I did 2 years ago at the last Startup Weekend I attended – and I was fortunate enough to win the top pitch on Friday night. I think it may have been because I said fuck in my pitch. Although, a lot of people also remembered me from the previous Startup Weekend and started calling me “Mr. Real Estate.”


Our team ultimately didn’t place – which may have been because it was an Internet of Things themed Startup Weekend and we weren’t that – but I think we developed a super solid business idea.

Either way, I had a blast. We knocked on people’s doors to validate our idea. We got a ton of positive feedback on what we were trying to do. And I was fortunate enough to meet a bunch of smart and ambitious people. I was so impressed by what our team accomplished.

But what I also love about events like Startup Weekend is that it shows you how vibrant the startup ecosystem really is in Toronto. There is no shortage of passionate entrepreneurs in this city fighting to change the world. And what’s great about this community is that they all know how hard it is to start something from nothing, and so they’re incredibly supportive. 

If you have any interest, I would encourage you to check out events like Startup Weekend. They’re a lot of fun and they all contribute to the greatness of this city.

Image: The Unlyst Team at Startup Weekend TO 2014 (Jerry, Louis, Landon, and me)

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