How to Do Everything Wrong & Win Startup Weekend

by Jennifer Thomas
November 26, 2012


One week ago I participated in the team that took First Place at Startup Weekend - Chicago edition. The idea: WhyDeliver - Get same day delivery from local merchants. From flowers, to shoes, to a case of 2 buck chuck - ordered by you, delivered by your neighbor. 

This idea, born just a few weeks earlier, was captained by Jimmy Odom and built out in 54 hours by a crew of 13 people. What we experienced was an intense 54 hour scene of cooperation & domination. 

We put together a team I'd consider the 'Dangerous (Baker's) Dozen'! The breakout: 10 of us were friends through a combination of 1871, StarterLeague & Mobile Makers and 3 others were passionate idea builders.

We must have done something right to win, but looking back, we pretty much did everything wrong. So I'll make the statement now, 'don't do what we did!'  And here's why: 

  Suggested Tactics:           Our Approach:

  Team of 3-5 people             We were crazy, but dedicated

  Focus on Mobile or Web      With 6 developers, why not do both

  Validate the idea                 Got this one right! 

  1 Presenter                        Jimmy knew the product, I had pitch vision so we tag-teamed

  Practice your pitch              Winged it. We were intimate w/ the idea & deck (& ran out of time!)

  Be passionate                    Wait, we did this one right, too!

  Sleep                                 8 slept over Saturday night & I beat all staying awake 41hrs

So, if we didn't listen to the tested tips, how in the heck did we win? We had a diverse team: dev (mobile & web), design, biz strategy, legal, content, social media & marketing. This is a rariety, but many of us planned to work together on an idea we all liked before we attended the SW Friday pitch night. We also focused on building only a feature of the overall vision that Jimmy has for WhyDeliver. Most importantly, we had fun! From the bottle of Jameson to watching sports & Game of Thrones on the big screen (we strategically commandeered a conference room).

Here's a little insight into our experience as told by our team through their favorite moments & advice:

Shaan - "It was impressive that 30 minutes before the presentation our team managed to make our website live, embed videos into our presentation, and prepare to present at crunch time."

Alex - "There were moments that I wanted to give up but seeing how hard my team worked kept me going! They were amazing and I didn't want to let them down."

Rebecca - "Be open minded. Don't micromanage your team. Have fun."

Jen - "The presentation highlights all the team's work and needs to be it's own stellar creation to give justice to everyone's contribution. Oh, and be mindful of copyright issues and just ask first!"

Jimmy - "Do yourself, your team, the developers, and designers a favor and communicate a clear vision of what you would like to accomplish and an initial roadmap for how you can get there!"

Daniela - "Trust your gut! Pick an idea that gets you excited and a team that is not only well-rounded in skill set but one that you feel you connect with and that YOU can truly add value to."

Greg - "We believed we would win from the first moment and never lost site of the target. Also, knowing our individual strengths created a Voltron Force to be reckoned with!"

Kevin - "It was great seeing all the mini teams of WhyDeliver operate as one large organization. We truly setup a headquarters."

Jordan - "Outwork everyone else, that's what it's always going to come down to. Which team goes the extra mile to vet their business plan, finish their website etc."

John - "Planning out our application flow, both functionally and technically, allowed us to create clear responsibilities, roles and integration points for the application. Having something to measure against during our checkpoints allowed us to recalibrate based on the remaining time."

Meg - "Listen to your gut when picking a team. Then, play up each member's unique strengths."

Jamie - "Great teams do great things. The fact that most of us knew and had worked with each other previously allowed us to focus, assured everyone would finish their tasks, as requested and the quality of their work would be awesome."

Shawna - "Being on the big screen like I was wizard of oz! I worked remotely but still had so much fun and interaction via web cam. It was fun to go nuts on all aspects of design."


(Quotes above in order of appearance in photo)

caption:  "I'm pretty sure we were the largest team over the weekend and quite possibly had the longest table in all of 1871. So when someone suggested that we create our own version of the Last Supper at that table none of us could resist." - Jimmy

This was not the first Startup Weekend or Hackathon event for several of us, so we knew how to make the most of our time and avoid some of the rookie pitfalls we've all made. 

As a startup founder, I was wholly impressed with how this team and idea came together over a few days. Wouldn't it be nice to lock your team in a room for a weekend for instant progress! 

Wait, I forgot to mention that WhyDeliver is representing Chicago in the Global Startup Battle where the 116 winners from each city are competing for bragging rights to the World Champion title!  Voting ends tomorrow and it's daily, so get your vote in now (and tomorrow too:)

A huge thank you to Cap'n Jimmy & our Dangerous Dozen for an unforgettable weekend! Also a shoutout to the mentors on site, including members of DesignCloud & Rania El-Sorrogy. And let's not forget about Adam Haun who made #SWChi possible!

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