One Man's Startup Weekend Experience

09/17/2014 | By Caitlin Thayer

This post originally appeared on

Thank you to Kevin Chick, a participant of Startup Weekend 2013, and a member of last year's winning team, for writing this blog post about his experience and about how Startup Weekend has changed his life since! Want to attend Startup Weekend 2014? Make sure to register, and we'll see you on September 26th. - Startup Weekend Hartford team

Almost a year ago, as I was finishing work up on Friday after a long week, I wondered if I really should attend Startup Weekend Hartford. I signed up for it after a friend told me how great it was, but I was really tired. Did I really want to stay up all night with people I didn’t even know? Could I really put a whole work week into the next two days? I eventually decided that I would give it a shot. Maybe this could be the thing that I was looking for.

Kevin Chick - HartfordSo, Friday night I went to the event, met some of the other participants, and we heard all of the pitches. We talked to the people who pitched their ideas, and teams were formed. I joined a group called Special Care and it was an idea of Barbara, a mom of a special needs child who needed a way to help organize all of the medical data she has, which is often on paper. A team of 7 people worked to flush out the idea, decide on the product, and develop the business model. Advisers came in and out of the room challenging our ideas and sometimes challenging the advice of others. It’s all part of the process!

We worked all Friday night, and all day on Saturday. And at some point on Saturday afternoon, it dawned on me that we might be able to win this. We honed our proposal, and Barbara and I were asked to make the final presentation. We would have 5 minutes (and not one second longer) to present our idea to a panel of impressive judges and a room full of people. We must have practiced at least 20 times. But all of our work paid off, and our team won first prize!

2013 Hartford Winners

For our first two or three meetings after Startup Weekend we were riding the high of winning and continued working, but then the reality set in of what it takes to establish a new business. The team changed a bit, and I decided to drop from the team to pursue working on a board that I had been asked to join. But the team is still working on establishing a new company (Quillible) and one of my team members (Nick Parian) is going to be a judge at this year’s Startup Weekend, which is Education themed!

Personally, Startup Weekend triggered something in me. After almost 20 years of working in Corporate America, it was time for a change. This experience helped me put some clarity on where I wanted to take my career. This past July, I left my job as an IT Project Manager and started as the Director of Operations for a small design firm in Hartford called CO:LAB. While we are not a startup, in that we have been business for the past 25 years, we are small and we want to grow.

A lot has changed since I finished up work that Friday afternoon a year ago, and I wonder what would have happened if I decided to sit it out. I’m glad I didn’t find out.