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This article is written by Startup Weekend Education attendee, Chloe Wood. 

When I signed up for Startup Weekend Education Oakland, I expected a scene like a hackathon – a rush for designers and developers during team formation and a few days frantically validating with customers and building a prototype. What I got was so much more.

I hadn’t planned to pitch. I was sitting comfortably near the back row, watching the first ten people go up to pitch, when one of the organizers screamed, “If you have ANY idea you’re considering, pitch! Sometimes last minute pitches become the best startups!”

My mind snapped to a business opportunity the d.school’s K-12 lab director had just mentioned to me offhand.

Heart pounding, I scribbled an outline and started practicing under my breath. “Imagine a classroom where every student is engaged…”


The idea: design thinking workshops for teachers and administrators to close the gap between the overwhelming demand and limited supply for design thinking training.

An hour later, I was in disbelief. I had moved on to the top 10 ideas and gotten an amazing team. Li and Jeremy immediately convinced me to pursue my project rather than follow a momentary impulse to join another team, where I wanted to learn from an IDEO designer.

My team, and Startup Weekend, jump-started my life and helped me believe in myself. Before, I had been struggling. My goal was to master design thinking, but I found it difficult to practice alone.

I was too scared to even interview folks at the grocery store. I desperately wanted to work with a team. Thanks to the fantastic group of people who found me at Startup Weekend, I experienced real teamwork for the first time.


Here’s what it looks like: you have everyone else’s back, and everyone else has your back. You’re all working towards the same goal, and you can lean on your team because everyone can complement your weakness with their own strengths or expertise. Everyone’s voice is prized.

Part of what made the team even stronger was conquering challenges together. Our lowest point was at 4pm on Saturday, when other teams were busy working on their prototypes. Having just finished defining our problem, we felt horribly behind. We were early in the process since my primary goal was to give everyone a guaranteed learning experience, rather than only try for an uncertain win. I had been encouraging teammates new to design, to become comfortable with the process by figuring it out themselves and moving forward with group discussion and consensus, rather than have me say what we should do next. At 4pm, our team decided that it was time to start getting things done, so I started directing more than guiding.

Our biggest success: We placed third, which is a wonderful achievement. Equally or more important, my teammates and I accomplished things we weren’t sure we could do. Victoria and Michelle did the full design process after first hearing of design thinking Friday night; Jeremy built a clickable website for the first time; I guided a team that worked as a unit. Perhaps my biggest personal success was learning I could take small steps right now towards my career goal of bringing design thinking to education.

The amazing thing about Startup Weekend is that it forces you to go from someone who is all talk, little action (has a vague desire to make the world a better place) to someone who is all action, little talk (is implementing and testing a specific solution to a problem). Your biggest constraint – time – forces deliberate action. Are we working on the right thing? Are we answering the right question? Even if it’s not perfect, is it good enough to move on?

The list of things to do seems ludicrous– forming and bonding a team, defining your problem, interviewing multiple customers, brainstorming solutions, consulting experts, building and testing possible solutions, doing competitive analysis, creating a reasonable business model, and making and practicing a compelling pitch. By Sunday night, anything seems possible. You’ve gotten a startup from idea to launch in about 20 hours of hands-on time. What can’t you do?

This suspension of disbelief is, I think, characteristic of Startup Weekends – the conviction that the company you are working on is real, or could be. The belief that you can achieve what you set out to do.

David and Tom Kelley call it creative confidence. At Startup Weekend Oakland, I found mine. Nothing will ever be the same.

Three important lessons I learned from my mistakes:

The team is everything. Find ways to support the goals of everyone on your team. Lean on them, make sure everyone is doing what they’re best at. Now I know to try agreeing on explicit roles to recognize people’s existing strengths, instead of having an unspoken, unintentional expectation for everyone to be comfortable doing everything.

Customer interviews are amazing. Their passions and frustrations will be obvious, and they will open up whole new avenues for you to explore. Now I know to start interviews earlier so we can adapt the solution earlier.

You will have to make decisions based on incomplete information. There is not enough time to do “enough research.” That’s OK because you can always adjust later. If it’s the right decision you’ll prove your gut right, if not you’ll learn something. Now I know to jump into brainstorming and prototyping earlier.

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