Lessons Learned From My First Time at Startup Weekend

Portland Startup WeekendI’ve always been an admirer of the Startup Weekend events in my area, but have never attended. I would actively follow tweets during the events and read press coverage from the days following. As a fan of the Lean Startup principles, Startup Weekend was a great way to see theories go through the validation process and then get developed. I finally stopped being an onlooker and became a participant. The last weekend of April 2013, I participated in the Portland Startup Weekend.

Having limited knowledge of Startup Weekend,
I went in with an open mind and yet held strong to a couple of rules:

  1. I was going to sit back, observe and follow the directions of others. Unless a leader was truly needed, I didn’t understand the process and wanted to see how it all worked first.
  2. Not leading meant, I didn’t pitch an idea. If I pitched an idea, I would have wanted to lead it through completion.
  3. I wanted to only work on a project that hasn’t been developed yet.

Photo by Boone Bergsma of We Think It Matters

I was on the team that worked on DownTheLine.me, a web app that used suggestions crowd sourced from friends and experts to help achieve goals more quickly. I genuinely enjoyed my experience during the 54 hours and made some great connections that will carry on in the future.

It’s unrealistic to assume that a team of strangers formed in a matter of minutes would run like a well oiled machine. There were some hiccups, but not all of my lessons learned came from my team.

The following are the lessons at I learned from my experiences and observations at Portland Startup Weekend:

Prepare Yourself

If you’ve never been to a Startup Weekend before and you’re pitching an idea, go to the bootcamp offered the week before and fill out your business model canvas. Have a sign up sheet ready with a plan for skill sets needed from team members before you arrive to the main event.

Practice your pitch for 60 seconds and pitch even if you feel that your idea is mediocre at best. You’ll need to get over any fear of public speaking just in case you have to answer questions during final Q&A. Besides, the real winning over of people happens during the voting period. You might fumble through your pitch, but people may really like your idea.

Actively “Network” before the event begins, get to know people’s strengths and make note of at least one designer (known as a hipster).

Keep Calm

Make your plan of attack public and make sure everyone knows which roles they’ll play. Have them recite it back to you if you want to make sure they’re on the same page.

Administrative (project management) roles are important. Designate the team leader as a tie breaker in discussions. In the very least, someone needs to moderate all group discussions with a timer and come up with a conclusion when the buzzer sounds. You don’t have hours to waste on discussing the wrong details.

Make sure your hackers can develop in the same language or in the least, their skills are complementary.

Build an MVP (or mockups) Saturday morning based on your group hypothesis and the business model canvas from Friday night. Get out in the city and get in front of people Saturday and show them your raw MVP to gain validation and be ready to pivot if needed. Build scrappy, validate, make sure to tie it all into a revenue model.

Seek mentor input often. They’re around and available to offer insight and guidance. Make sure you follow the judging guidelines. Don’t get side tracked or be fancy trying to create more if you don’t have the basics drilled down.

In the end, don’t present first, but make sure you do your tech check first. This will give you a time cushion to work out your final kinks.

Most Importantly… Have Fun!

Enjoy the rare opportunity during the weekend to get to know your teammates through conversations during lunch and dinner. Give your brain a rest. Walk away from work and come back refreshed.

Don’t be afraid to share your views. Good ideas are built from a starter idea. Use the feedback you received as an opportunity to learn.

Whatever the reason is that you decide to attend Startup Weekend,
be to sure make friends and have fun.

Now some of these lessons seem obvious, but when you’re in the heat of the moment, conventional wisdom doesn’t happen as quickly. My name is Derek Wyatt and after my first taste of Startup Weekend, I’ve become an addict. I look forward to the next Startup Weekend and have already started to work attending future events into my budget.

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