Right after Toronto, I had to leave for the US. My first destination was Detroit where I spent a night couchsurfing. The day after, I was on a bus to Chicago and its Startup Weekend. This is the story of this awesome weekend…

1.ID Card

• SW Chicago
• 75 attendees
• 70% male / 30% female
• 9 teams
• 4 main organizers
• 13 coaches

Organization: Startup Weekend Chicago is a rolling machine! Organizers were older than the ones I’ve seen in previous events. The event itself was planned down to the last detail and very well executed. The facilitator was great and put everyone in an awesome mood as it should be! In a word: a great team!

Venue: The Startup Weekend was held at TechNexus which is an incubator. Offices are located on the 12^th floor of the Civic Opera building in downtown Chicago! A beautiful venue in which you could feel the startup mood in nice co-working spaces or in the spacious cafeteria!

Chicago is such a huge and nice city which has remarquable architecture (surprisingly beautiful for such a big North American city)! Public transport is really okay in this flat city where you will find some of the best food in the USA. I enjoyed walking along the Lake Michigan struggling against the wind and spending good times in some bars located in nice districts of the Mid-West town!

2. Pitches and teams:
On Friday night, I counted 38 pitches! What a great number! Ideas were very diverse and creative and I had to say, Americans know how to pitch! That’s why I had so much trouble choosing a team to join! Do I want to work on an airport picking project, a HR reference system assisted by video, an educational idea mixed with virtual reality… It took me a while. 11 ideas were selected as the most popular ones and everyone started to form teams. On Sunday, 8 teams made it to the final presentation.

3. The team I joined: LegalBid
Rob pitched the problem about how the supply of lawyers in the US is way above demand and how some lawyers were looking for new cases all over the place. I liked the challenge of matching this Supply and Demand thing and joined the team. At the very beginning, we were 4 guys good to go but we quickly became 6 and on Saturday morning, we were 8 on board! And when it comes to big teams, managing and leading is always the most challenging task!

Our main advantages:

Large comes with diversified and we were indeed very diversified! Three of the main key skills for a Startup Weekend were represented in that team: Business, Design and Programming. We had people from consulting / lean startup / social media / UX experience / back-end and front-end development etc – the good recipe for a great pitch on Sunday. Aside from Startup Weekend Stockholm, this team was the most diverse and skilled one I ever worked with.

We built a 100% working and responsive MVP: our tech guys worked very hard along with our designer to build a nice website with all the basic key features integrated. It worked and it looked good! However, what I thought would be a great advantage turned out to be not that impressive because half of the teams had a similar MVP… As impressive as ours… This is just to tease you about the level on Sunday… So keep reading 😉

We quickly set up a good division of tasks which allowed us to reach objectives and get work done smoothly in this large team.

Our main disadvantages:

8 people is hard to manage or lead, especially when you have strong and skilled personalities on board! We didn’t listen to each other enough… Everyone would express their own ideas but we didn’t reach this common energy which naturally puts everyone on the same page in terms of objectives and building.

We didn’t spend any time getting to know each other. We started working right away without even being aware of who is good at what and, more importantly, who we are… Going to a Startup Weekend is about adopting an Effectual method: do what you can with what you have. In other words, look at your resources and build your product out of them. And, we didn’t spend time figuring out what kind of people we had in the team and what they could bring to reach the best result. We didn’t know our resources well enough!

We had neither a leader nor a manager. With a large team comes great
responsibilities and there is nothing harder than managing and leading a big team full of people you just met who are all super skilled in what they know and keen to share their point of view! We should have picked a project manager right away for better coordination. In small teams, it comes more naturally. I, for instance, sometimes take the responsibility of putting myself in the position of leader but this team impressed me too much to dare. But in the end, I learnt so much from it!

We went too fast and forgot to dig deeper on some key aspects of our building process. We did target a niche market but we didn’t show enough of its potential and our customer validation should have been stronger! Finally, we didn’t polish our idea enough and we ended up not showing a proper differentiation to make the judges click! So, time is money but money comes with the right time spent on the right things!

What we achieved:

LegalBid ended up being a platform on which people could put online their legal issues and wait for proposal from lawyers. They could then pick the best bid and get more information about the lawyer himself.

4. Final pitches:
I said in my previous article about Startup Weekend Peel that the general level was pretty high. Well, it didn’t take long to beat that! Out of 8 final teams, 5 had a kick-ass working MVP (basically, a prototype anything that would look like a final product). I was impressed!

We started working on the pitch on Saturday night… It was the first time that I would start working so early on it! Our presentation was very good and well designed and we spent the right amount of time on our demo but we didn’t put enough emphasis on the great potential of the market. In the end, even if Rob did a great pitch, judges seemed very skeptical about a real need and the differentiation aspect we were bringing into the game… We didn’t push the right buttons to get the right results.

The 3 first places were pretty understandable. Teams had great MVPs and ideas were more original and polished than ours:

• 1^st – Vreference for an easy way to get references through videos for job applications
• 2^nd – Rewind for its super good-looking collaborative platform to share kind of old-style personalized music playlists
• 3^rd – MathVR for a tutoring Mathematics tool with Virtual Reality

5. Conclusion:
To be honest, it is the first time during this trip that I was sad about not being rewarded… I always say: A Startup Weekend is not about winning, it is about learning, sharing and meeting people… But winning always feels good right! So the reason I felt sad is because we worked hard and we had such bright skills on-board that we could have shined! I felt angry with myself as well because I just let some big mistakes happen… it was a feeling of having wasted a great potential because of mistakes that could have been avoided by a Startup Weekend attendee as experienced as me. Anyways, this weekend proved me once again that there are no specific rules to win… Rocking a Startup Weekend is all about finding the right balance between an innovative idea and building the right relationships within your team! To sum up, once again I learnt so much from this experience and especially from working with this team!

This article is dedicated to Mars Noumena, Carlos Pena and Sam Wilcox for opening their home to a traveler just passing by!

Merci.