By Chris Kay

I’ve attended several Startup Weekend events since the first Toronto session in 2010 (where Rajah and I first met), but my participation was always as an observer, lurking around, watching teams hustle. So I was excited by the thought of signing up for Lean Startup Machine this past weekend, joining a team, and getting my hands dirty. I’m not going to tell you what my team’s idea was, how we validated it, or if we won; that’s not what’s important. What’s important is what we learned.

Walking home last night in the darkness and the cold with about five hours of sleep for the weekend I reflected on the roller-coaster ride my team experienced over the weekend. It was an experience I wouldn’t trade for any funding round or valuation. Not only did it make us better entrepreneurs, it made us better people.

Customers Before Problems. Problems Before Solutions

Instinctively entrepreneurs often work backwards in this process. In fact, Startup Weekend and Lean Startup Machine are designed counter-intuitively from this hierarchy. Entrepreneurs have an idea that they pitch, and then test if it’s a problem for a target customer. If it’s not a problem for that customer they try to find another customer with the same problem who might want the solution. The problem we found in this process was we had a preconceived notion of what the solution should be and we wanted people to validate it, causing confirmation bias or frustration, neither is fun. We should have been focused on the customer by listening to their problems, then finding ways to solve them, not starting with the solution. We had a hammer and we were asking if anyone had a nail they needed hammered.

Don’t Just Ask Questions, Talk to People

We realized there’s a big difference in customer development between asking opened ended questions to your target customer, and sitting and having a conversation with someone. Once we tossed out the list of questions and the time limit per interview, and just talked, we learned so much more. Not only did we learn more about the customer, we learned about problems we didn’t know existed. Lastly, we met a ton of really cool people. Go have a coffee or beer with your potential customer and just sit and talk to them, you might be surprised in what you learn.

These two learnings taught my team to put people first, not the product. And we rearranged our thinking when doing ideation. But lastly we learned to fail, and most importantly, fail as a team.

Kill Your Darlings

Writers often say you have to kill your darlings, meaning you have to be willing to kill an idea no matter how emotionally invested you are. Late Saturday night we had to do just that. After spending hours on the street in the cold darkness we couldn’t get validation on our proposed problem. Tired, cold and with no viable alternatives, we had to vote to kill the idea and start again. This was not easy. We had to look our team-mate (the founder of the idea) in the eyes and tell him it wasn’t going to happen. We had spent 24 hours working on this idea and we only had another 24 to go before presentations. We were desperate, defeated, exhausted, and a little broken, with 24 hours left and no ideas. We questioned even if we came up with a new idea, could we work through the validation process in time for Sunday’s pitches? To our surprise, we did.

We found our second idea while drowning our sorrows in a nearby bar and talking to other patrons enjoying their Saturday night. The people we were talking to (customers) were telling us about a problem they had (problem). Now it was our job to find more validation to ensure this wasn’t just an one-off occurrence, and to find a way to actually solve the problem. We moved exponentially faster the second time around, completing validation and iteration cycles in an hour. We documented conversations with customers while on the TTC on our way to a Meetup group of new potential customers. Without that first failure we never would have improved our understanding or implementation of the framework. We followed the spirt of the Lean Startup Machine framework, opposed to the letter.

From that failure we grew as people, as entrepreneurs and as a team. Going through that defeating time brought our team closer together. We had seen each other at our best and at our worst. I’m unspeakably proud how well we handled it and that we didn’t want to kill each other by the end of the weekend. It sounds weird to say, but our team definitely got more value out of the weekend because of that failure.

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Chris Kay is a Financial Analyst, Co-founder of Multiplicity. Follow him on Twitter – @ChrisJKay
By day, Chris is a Financial Analyst working with entrepreneurs and angel investors on their personal financial affairs.

By night, Chris is an active member of the Toronto tech start-up community. Chris is a two-time mentor at Techstars Startup Next Pre-Accelerator program, the #1 startup pre-acceleration program in the world. Prior to co-founding Multiplicity, Chris acted as the Group Manager of the Ryerson Angel Network.

Chris studied Finance at Ryerson University, and has obtained his Canadian Investment Manager (CIM) and Chartered Alternative Investment Analyst (CAIA) designations, he is also a CAIA Canada Chapter Executive based in Toronto. Chris has completed the Level 1 of the Chartered Financial Analyst program.