My Startup Weekend Experience

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The whole group of us @ Startup Weekend STL

When I first learned of Startup Weekend I had trouble finding info about what the actual experience would entail. So, I wanted to take a minute and share my personal experience from my first ever Startup Weekend and give you an inside look at the event from my perspective.


I’m a father to two very young boys. So, it is difficult for me to get out to the occasional networking event. But when I stumbled upon this thing called “Startup Weekend” and noticed that it was happening in just a few short days… I couldn’t help but be intrigued. I reached out to a couple friends I thought may have participated in past events. They urged me to “Do it!!!”. I nonchalantly mentioned it in passing to my wife, who saw right though me and could tell how excited I was by the whole idea. It was a big sacrifice on her part to take care of our boys on her own for the whole weekend (Little did we know that our youngest was about to give mommy a lot of trouble because of an ear infection!) I’m so lucky and grateful to have such an amazing partner and wouldn’t have been able have or share this experience if it wasn’t for her!

Day 1: Friday

Boy, this was exciting! I was anxious, curious, and ready to get to work. I stopped by FedEx on my way there after work to print off some business/invitation cards. I had just created a Slack group for the St. louis Startup scene and thought Startup Weekend would be a great group to share it with.

The event started with some free swag, mingling, and delicious Jets pizza (can’t go wrong there!) followed by a short introduction by our hosts Bill Kenney and Chris LeBeau. They explained the process:

  1. Everyone has 60 seconds to pitch their idea.
  2. Everyone will vote for their three favorite ideas.
  3. The top 10 (or so) ideas would move on and actually be worked on over the weekend.

Then we got right into the pitches. Bill urged everyone to get up and pitch an idea. I hadn’t really come to the event to pitch or work on any of my ideas, but figured it would be good practice to get up and give it a shot. I was the 2nd to pitch (about 40 of the 70 people there got up and pitched an idea). I just wanted to get it over with and not really think about it too much. I still have a lot to work on in the public speaking area, but a lot of personal growth comes from putting yourself in atypical, uncomfortable situations… right?

After my mediocre pitch on a decent idea, I sat down and took notes as I listened to the rest of the pitches. I took note of any pitch idea that piqued my interest, and gave it a score from 1–10. The idea here was to help me decide what teams to vote for, and which one to eventually join. Trying to remember my thoughts on the ideas after 50 pitches would have been difficult!

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A snapshot of everybody forming their teams for the weekend

Here are a few ideas I really liked:

I Was There — Online repository for sports fans to share their experiences from specific games
Hungry Trip — places to eat ideas for out-of-towners
Fan Loyalty — live rewards program for fans that are at the game

But there was one that captured my interest most:

Competer — Customize leaderboards with friends.

This was my favorite of the bunch and the team that I ended up joining. My initial reaction was “Wow, this would be a lot of fun for our office ping-pong bragging rights!”. I knew there was something there with this idea.

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Me, Ryan, and Joseph. Laura couldn’t make it to the final day :(

We ended up with 4 members on the Competer team. Joseph (the idea man) and Ryan (Joseph’s business partner and friend) were both entrepreneurs, and business owners. Along with Laura (a Leadership Consultant with a PHD in psychology) and myself (the Designer with UX focus) we had a fairly well-rounded team.

After some quick intros, we jumped right into the discussions and started devising a plan. Joseph elaborated a bit more on his idea and discussed how it came to life along with the progress that had been made so far. The idea was actually a good 10 years old and originated because he and his college friends actually used a giant, dry-erase wall full of leaderboards for random things like video games, athletic achievements, etc. It was a place for bragging rights. With a better understanding of the idea, we had a pretty clear picture of the direction we wanted to go in and began to nail down the specific tasks that needed to be accomplished over the weekend.

Eventually, a little after midnight, we called it a night. Earlier than most other teams, actually. Joseph had a decent head-start on the idea already, so we had a pretty clear plan for what we needed to crank out the next day. We were able to go home, get some rest, and have a focused mind in the morning.

Day 2: Saturday

Rise and shine and got right back to it. Over breakfast we began by sharing some thoughts we had during our nights alone.

Later today we would have numerous meetings with the event mentors, so we did some preparing. We did a little research on each of them and signed up for meetings with the ones that would provide the best insight for our particular needs.

We did some prepping and had problem spots that we were going to focus on with the coaches. For instance we asked each mentor what they believed our best value proposition and monetization strategy was in their mind.

The mentors were fucking amazing. We got a wide range of responses. Each one was incredibly helpful, but came from their own perspective on the product and how they would use it. This was actually really encouraging. It shows that not any one person has it all “figured out”. There is no template for success, especially when it comes to startups. We learned to be open to change, try new things, and adapt from what you learn.

We used their feedback and got to work nailing down our exact strategy. We created an online survey that asked questions about people’s competitiveness, what people like to compete in, and if they would find the sort of app we’re creating useful. We got over 250 responses in just a few hours and had a lot of valuable data to help us.

So, for the rest of the day we worked on updating the pitch deck and I also worked on UI / UX aspects and created a few mockups of the iOS app. We were in the zone and got a ton accomplished throughout the evening, which put us in a good spot to head home at a reasonable time.

The quick mock-ups that I designed for the Competer app

Day 3: Sunday

We spent the morning getting the pitch deck finalized and designed exactly how we wanted to present it. Then, all we had left was to prepare for was the presentation itself. Joseph rehearsed the presentation dozens of times, got feedback from us on how to improve it and eventually we were ready to go!

Pitch time! We would be going 4th, out of the 8 teams presenting. It made me feel pretty good about our presentation after we saw that others weren’t Steve Jobs-esque speakers and that we would definitely have one of the most well designed slide shows (designers were pretty scarce at this particular event).

Joseph nailed it. The presentation went great and the Q/A with the judges after went really well, too! I even got to chime in a few times myself about the usability, importance of simple UX, and target markets.

After the final team gave their pitch, the judges went in solitude (for what seemed like an eternity) to make their selections for the winners. The big reveal: 3rd place: Wanders. 2nd place: Competer (That’s us!!). And 1st place: Dinner Kits. The guys at Dinner kits really nailed the presentation (plates of actual food for the judges as an example of their product) and also had the most progress as far as generating real interest in the product (via grocery store managers). A well deserved outcome for them, no doubt!

Reflecting on the Experience

Man, I learned so much, and it was great to feel like I was an important part of bringing something to life. My job has turned into a place where I don’t feel ownership or importance in my role the way that I used to (but that’s another story). Joseph is in the process of taking the idea through the Square One program at CIC and hopefully we’ll reconnect to continue working on the project together as a group once that is completed.

To wrap things up I’d just like to say that overall it was a great learning experience and it is great to just get out of your comfort zone and do something completely new (especially when it involves what you’re passionate about). I would definitely recommend the event to anyone interested.

If you would like be a part of the Startup STL Slack community click here.

You can follow me on twitter @chrisd008
Or see my design work on dribbble

Written by

Designer with a passion for UX and solving problems. Husband, father, hockey lover, and rock & roller. Currently working on Design Systems @ Bayer

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