Five entrepreneurial lessons in 54 hours: Startup Weekend DC 2010

Last weekend, I participated in Startup Weekend DC 2010. It was a great experience that I recommend to any entrepreneur. It compresses the startup cycle by having people pitch, develop, and present a business opportunity to a panel of judges in one weekend.

I'm excited to say that our team, iSpeedShop, won the competition for our mobile shopping app! It was an unexpected honor given the high quality of the other prototypes and presentations.

Here are five lessons I learned at the Startup Weekend:

1) You can get an amazing amount done in an uninterrupted spurt

Participants blocked off their whole weekends, so we could work without outside interruptions. We found that we could get a lot done because we were insulated from exterior obligations and could work as late as we wanted.

2) Entrepreneurs are willing to contribute any way they can

We needed a front-end iPhone developer; we didn't really have one. But we did have someone who had coded several years ago, though he came to SWDC10 planning on taking a business role. We asked him to take on the coding with Titanium Appcelerator and he jumped in. Working with the other developer, he was able to code up a working prototype, complete with accessing the backend database.

Saturday afternoon, I became the data-entry guy. It became a joke – "Is there anything more demeaning we can make Jeremy do?" – but I was happy to do whatever I could to meet our Sunday deadline.

3) Entrepreneurs help each other

Despite being so pressed for time, and nominally competing against each other, teams were very generous in helping each other. For example, we needed an iPhone-to-Mac cable, and other teams let us borrow one each day. Our team helped another by answering market-research questions. A friend in another group helped tweak graphics for our icons on Sunday, during crunch time.

4) "Leggo that ego"

When it came time to decide who would give our presentation for Sunday night, a developer on our team suggested he'd give it. I had thought, because I pitched the idea Friday night, that I'd give the presentation and the developers would do the demo. I thought about the advice the organizers gave us Friday night, "leggo that ego," and decided that I didn't need to give the presentation as long as the people who did were enthusiastic and the slides were in good shape. The developers did a great job presenting, and we won the contest!

5) Shut up and listen

Saturday morning, there was doubt amongst some team members whether we could make our idea work without external cooperation. I tried to convince them, without much success, that we could still create a useful app. Then the organizer, Stephen, came in and gave us a pep talk about what a good idea it was and how we could make a useful app regardless of external cooperation. He was more convincing than me!

Later in the day, another person stopped by and asked the external-cooperation question. Instead of responding defensively, I kept my mouth shut and let other team members answer. I was happy to hear them give the same kinds of answers that Stephen and I had given earlier. By letting them talk, I got to see that they were convinced. Further, those team members were probably more effective in convincing that person because they'd had those same doubts earlier and overcome them.

Thanks to Stephen Douglass (quite a gymnast!), Nick Seguin, and Nicole Provansal for organizing SWDC10! And to Touchstone, Noiz Ivy, Affinity Lab, SproutBox, and Intridea, YoungImpact, Luna Grill & Diner, and Chipotle for sponsoring it!