10 Lessons Learned from My Adventure at Startup Weekend

2013 has begun on a great note for Calgary with 80 participants collaborating to create 11 new startups at the just concluded Startup Weekend.

What an incredible event. With so many new startups being built on the fly, including an idea of my own (Outrank, a ranking system that separates the doers from the talkers), all the participants embraced the “No Talk, All Action” slogan over the 54-hour period.

The concept seemed simple: you get together on a Friday evening and pitch startup ideas, the community votes for the ideas they’d like to see developed, teams are formed, and the next two days are spent trying to validate the market, refine the business model and build a minimum viable product. The teams pitch their startup and demonstrate their product to a panel of judges on Sunday night.

I currently work with Startup Calgary and registered for Startup Weekend after hearing amazing things from those involved last year. Spoiler alert – it was a very exciting, difficult, enduring, and insightful weekend that I won’t soon forget. I wanted write an article for those who has never attended one of these events in order to inspire you to attend the next Startup Weekend or similar event in your community.

Here is a collection of my experiences and lessons learned at the event:

1. Meet as many people as possible.

The calibre of people at the event was incredible! By this, I don’t mean 80 Fortune 500 company CEO’s attended. My definition of high calibre for this event was people excited to get their hands dirty, work with those they didn’t know and help build something that wasn’t their own idea. From the people I had the pleasure to meet, I quickly learned that this type of event was not a rarity for them, and that they were comfortable working under extreme uncertainty. To me, those are the qualities of the most valuable co-worker, employee or friend one could have.

2. Include as many people as possible when brainstorming.

When we started the idea, we were practically strangers. It was important to throw as many ideas as possible onto the white board to collect everyone’s thoughts and discover the hidden gems we would not have discovered in isolation. Once people start talking, they spark each other to add more interesting ideas.

3. Include as few people as possible (include only key people) when making big decisions.

Discussions that involve the entire team, should not actually include EVERYONE on the team. There were 80 people at our Startup Weekend working on 11 ideas with team sizes between 5 and 10 people. Although people agreed on ideas, their own interpretations seemed different solely based on their choice of language. In other words, we were saying the same things but argued about language, which was irrelevant in our situation and prevented work from actually proceeding at points.

4. Connections matter.

With only 54 hours to create a startup, explain the offering, build a prototype and validate the target market, we had to utilize every connection available to us. With only two hours available (self imposed), we blitzed our social media and personal networks to get as much feedback as possible. We collected 100 responses in that short amount of time and realized what we were doing was valuable, and how we had to tweak some details.

5. Choose a Project Manager from the get go

Project Management is more important than natural leadership. If someone is not tasked with managing the entire timeline of the project, things could get seriously out of control. (We almost collapsed without a set plan in the final hours before the final pitch).

6. Prepare to physically and mentally endure.

To be clear, we did not work for 54 hours straight. Our team went home each night around 11pm to sleep in our own beds, and returned the next day at 9am. Despite this, it truly felt like we worked for 54 hours straight. When I got home each night, I would excitedly share everything about the event with my girlfriend, and then lie awake for 2 more hours before my body would calm down from the excitement. The next morning, I would rush out of the house with a strong cup of coffee in hand and immediately pick up from where we left the night before.

7. Don’t stop, no matter what.

“Darkest before the Dawn” is an understatement. Just before our biggest breakthrough in creating our best features and an understandable value proposition, we were all depressed and (in our heads) contemplated disbanding the team. We were going in circles and had lost all understanding of what we were actually creating. We took a break, went off in different directions to put our thoughts down on paper.

When we came back, we tasked one member of the team (purposely not me as I proposed the idea) to go off for 5 minutes and complete our entire value proposition. The reason for this is because we felt every team member should have the same message in order to succeed. When she came back, her messaging was crystal clear and the team instantly agreed upon and rallied around the specific descriptions of how, what and why we were building the startup. After that, we were at our strongest point as a team.

8. Break when things “heat up.”

When an agreement cannot be made on a specific feature or idea and things start to heat up, take a break. This five-minute break allowed us to clear our heads and calm down. When we came back together, solutions seemed to come more easily and we moved past the conflict (some people just need a cigarette or relieve their bladder before they become less hostile about an idea).

9. Don’t waste time arguing about features.

Features are irrelevant in the grand scheme of the idea. Choosing the most effective distribution channels, industry partners and customer segments is much more important than “which stats we should include in the ranking list?”

The reason? It takes two seconds to include different stats or change the colors in your product if they are wrong. Choosing the wrong distribution channel might mean you don’t understand the key players in your industry and therefore, will end up with an ineffective strategy. Bad distribution strategy equals no customers. Why am I emphasizing this? We (mostly me) wasted a large amount of time arguing with our designer about what “widgets” customers would like, instead of working on how we actually get our product to the customer (dark flashbacks of our time wasting arguments are now in my head).

10. Never raise critical questions later than 8pm.

Once 8pm had arrived, we had been working for 11 hours straight and for us that meant we were exhausted and slightly irritated with each other. Exhaustion mixed with irritability combined with a strong dose of “who really is our customer?” type group questions equaled irrational-crazy-people. The only similar situation I can relate this to is when you ask a heavily intoxicated friend about their thoughts on current public events. If your friends are like mine, it quickly escalates into an argument about philosophy, ethics and religion. You can only imagine the “exciting” arguments that follow.

In summary, this was an amazing experience for me, and one that forced me to quickly learn some hard lessons. Despite the seemingly difficult time we had, it was the best time. If I were to create a list of all the things I enjoyed about the event, it would be 50 items long.

Big congratulations to the top three teams: Parley (performance management made simple), Mood2Food (connecting people with food allergies to restaurants, resources and each other), and Give A Mile (crowdsourcing airmile donations for those who can’t afford to visit their loved ones who are terminally ill). There was also an award for the Most Exciting Pitch, which was won by WeScored App (when your team scores, your phone roars).