Events Elaborated – Startup Weekend Chicago

The Startup Weekend at Chicago starts with a 100+ attendees in the Excelerate Labs working space.

The energy in the room is bustling as developers, marketers, product managers and startup enthusiasts start trickling in. In a few minutes, the room is abuzz and everyone waits for the weekend to begin.
Opening the floor for Chicago’s Startup weekend, Adam Haun introduces Troy Henikoff. Troy inspires the buddy entrepreneurs and talks about the space at 1871 and Excelerate and gives an overview on its significance and that of Chicago.

I’m sitting in the audience listening to this awesome leader addressing the crowd and wondering how the weekend is going to unfold. Most of the coaches aren’t here and as a technical coach, it’s the most exciting feeling to be sitting amidst 50+ developers in a room of 100. The talent in the city is a great blend of designers, business development minds and engineers alike. As I check of another thing that I love about this beautiful city of Chicago, Mike McGee takes the stage.

The crowd is listening intently and as Mike shares his experiences about his first Startup weekend ever, he shares how he ended up rewriting his code and staying up all night on Saturday night to give a rock star presentation on Sunday! There are bursts of laughter as Mike walks everyone through the roller-coaster ride that Startup Weekend is going to be.
Sitting on the edge of my seat, I’m already imagining what the pitches on Sunday look like, the chaos that goes on through the weekend and am floating along as Mike paints a picture to help us all get prepared.
As the last few minutes of the weekend are laid out in mind map, Shane Reiser walks in to talk about what it is that we’re going to do! This means, it’s time to get started.

Shane gets everyone in the room to play ‘Rock, Paper, Scissors’ and within minutes the uproar sounds like that of an army going to war. The winner opened up the pitches for that night.

In true Startup Weekend style, 60 pitches are then being delivered in exactly 60 seconds each.

We vote and the top 17 teams get selected.
What follows is 52 hours of non-stop conversations and coding.
As a coach at the event, I spend Friday night brainstorming with the leader of team and helping her refine the value prop behind her project. Saturday is largely spent connecting with individual teams and covering all kinds of topics.
The Human Stock Price team seems a little lost and I walk them through a crash-course on the Lean Launchpad Business Canvas, then I engage with the development efforts at Fill in The Closet and while the rest of the Microsoft team participates on the She-spn, Patient Tracker and teams.

In a matter of hours, most of us have gone from strangers to buddies and 1871 is our new temporary abode. On Saturday after noon, as some teams struggle to pivot ideas and come up with viable business models, others sail seamlessly and look for designers to start prototyping. Amidst the Startup Weekend chaos, everyone has one goal for the remaining 20+ hours and each individual makes their best effort to swim across to that Sunday pitch. Some succeed, some walk home early and some decide to start off on their own teams to pursue their dream idea.
Persuasion, leadership, personal accountability, goal orientation and teamwork – every skill that makes an entrepreneur is now on display in various capacities.

Mentors are now walking around on Saturday afternoon meeting the teams. As I connect non-stop with the attendees from the Microsoft desk, I feel the trends of similarities between these budding entrepreneurs and the strong personalities that set themselves apart from the crowd. In every conversation, there is something new to learn and something to share.

A few hours into Saturday morning and someone asks “Will you walk to our table and help with our website?”… And so, I start walking around helping with a snippet of code here and a snippet of code there. Building websites, creating data storage, helping with app development and doing my ‘technical’ mentor thing. As evening floats in, some team-mates are bidding goodbye to their team to go out into the big, real world and get some customer validation done! More MVP development and research follows into the wee hours of Saturday night.

Sunday shows up unexpectedly and no one is ready enough to brace themselves. The hackers speed up and the adrenaline in the air is now sky high. Those that have had a few hours of sleep show no sign of fatigue in their work, you can see it in their eyes as they feverishly put together their pitch decks and start practicing their pitches.

Jeff shows me his She-spn Windows8 app and I’m blown away with the coolness of the user experience. Marion’s team is now tracking steadily with a strong strategy of diving the tasks and conquering the final pitch. John is now brain-storming with the Vintage team while he also participates with his Patient Tracker team.
The Microsoft team is not only a sponsoring spectator at the event but, we’re incredibly immersed and feel ourselves through this roller-coaster reaching new highs as we connect with a talented pool of attendees from Chicago and also from Pittsburgh, DC, Cleveland, Indianapolis, Champaign, Milwaukee, Iowa City, Omaha, Jacksonville, San Francisco, and Seattle.
As the pitches kick-off, everyone waits patiently to see the creations from the exhilarating weekend that has just gone by.

WhyDeliver showcases a true winning pitch and wins the competition to move onto the Global Startup Battle.

The top six teams include, Pix2gether – an iOS app on Azure, WhereFi, Patient Tracker, Givee – a website storing data on Azure, and SHESPN – a Windows8 app.
It’s time to go home but, we’re not done yet. John helps me setup a few interviews with the participants. As they share their stories and experiences, I can’t help but imagine their journey through the weekend.
Some that I met on Friday night and created an instant bond and others that came together over the course of the weekend.

It’s amazing how much one can learn and create in one weekend. Build a foundation that will now help them pivot some more, develop some more and eventually launch into their startups.

Exhausted and yet, energized, they’re all going home winners!


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