3 Things I’ve Learned From 3 Startup Weekends


Guest Post by Chris Schuermyer, Portland Startup Weekend Organizer for November 2013:

1) Do the Bootcamp

Bootcamp is basically a mini Startup Weekend, with some of the same great food, and some of the same great people. It’s good practice for introverts (like me) to see what’s going to happen during the big show. It’s also great practice for the strategists to network, pitch, and refine their idea prior to the weekend. In my first startup weekend, the idea that I joined in the bootcamp went on almost unchanged to winning the whole Spring 2012 weekend (thanks to Vanessa for the awesome ride). The best part is that you’ll meet a handful of awesome people at bootcamp that you’ll then recognize during the weekend. Since I didn’t know a single person at my first SW, it was really helpful to have already met some great people at bootcamp.

Introvert Pro-Tip:
When you introduce someone, even someone you just met 2 minutes ago, don’t just say their name, say one thing you know about them (that you learned in the last 2 minutes if need be). For example: Let’s say I just met a girl that makes hats for a living. I want to invite somebody else into the conversation because he’s just standing by the pizza looking lonely.

(Me to 3rd person with eye contact): “Hey, how’s it going? I’m Chris!”
(3rd person): “Good, my name is Bob, spelled with one ‘O’.”
(Me, having already forgotten name): “Hey Bob, have you met . . .”
(2nd person): “Candice”.
(Me in an obvious fabrication): “Candice is named after Candice Cameron from Full House.”.
(Candice): “Actually I was named after my Grandma, not DJ Tanner”.
(Bob): “That’s really cool. However it would be almost just as cool if you were actually named after DJ. So, do you guys know what Bob Saget has been up to since AFV replaced him with Tom Bergeron?”

… BAM!!! Conversation started!

2) Do the Pitch

It doesn’t matter what you pitch, just pitch. Pitching on Friday night is the perfect moment for you to get way out of your comfort zone, stand in front of a bunch of strangers, and talk about a problem/idea that has only ever existed inside your head. In life, no matter what the context, getting out of your comfort zone is the first step toward feeling alive. The kicker is that every last person in the room is pulling for every single one of the 40-70 people pitching, because everybody realizes that it takes a lotta balls to suck it up and get in front of an audience. Counting every one of my 3 tours of PDXSW, Friday night has always been in the 99th percentile of enthusiastic optimism that I’ve ever seen in my life (note that I’m an electrical engineer, so your mileage may vary). Why? Because everybody there has correctly assessed that this is a group of amazing individuals that decided to put there man-pants on and show up that day.

OK, for the engineers/hackers (like me) here is the brass tax on why pitching matters:

  • First off, it sets a precedent for how you conduct yourself for the weekend. You want to be meeting awesome people, so you might as well to start with everybody at once. When I pitched the first time, I was visibly shaking in front of the crowd. Yet, by the end of the weekend I had probably met 40 people that either inspired me or taught me something.
  • Second, it’s good to own your idea and see what the response is. I pitched an idea about using applied natural language processing that I’d previously only ever mentioned to a handful of friends. I wanted to spend the next 1-2 years building it in isolation. It only got 3 votes, which means it’s a really good thing I didn’t sink anymore time into the idea without doing a lot more customer validation.
  • Lastly, if you pitch, you already have a conversation topic regardless of whether your idea gets picked or not. My second round I pitched something about helping octogenarians, and some people thought that was awesome/bizarre enough to ask me about it throughout the weekend.

Life begins at the edge of your comfort zone. Pitching is just a really obvious place to start.

3) Meet and Help as Many People As Possible

One of the most important things I’ve learned in my adult life is that everybody knows something I don’t (hat tip Shashi). Whether it be what a doula is and why they are important, or how to setup mobile app analytics, everybody knows something you don’t. Startup Weekend is one of the best events for gathering these kinds of nuggets because 1) the background is so diverse, and 2) it’s actually crap you care about learning. With a pool of awesome hackers, hipsters, and hustlers, there is so much to learn that I end up just writing a list of topics that I have to Google after the weekend when I have more time. For example, I learned about Prezi in my second SW, and took that technology to my corporate job and baffled/impress(.js)ed a whole audience of engineers that had never seen anything outside of PowerPoint. I also met a guy in the ShopMyPins group, Christopher, who told me about Portland Creative Mornings, so we went and saw a speaker that would change my life in an even more dramatic way. The reason that everybody who shows up to SW is awesome is that they, unlike your friends who talk about entrepreneurship but never do anything, actually took some sort of action and showed up that weekend. There is an infinite difference between those that talk and those that act, especially when the action will yield unknown results.

The flip side of meeting people is helping people. Just like everybody has something for you to learn, you have something you can teach. Whenever I have downtime at SW, I generally try and see if there is something I can do to help the other teams along. There are several announcements throughout the weekend for what the teams need help with. A lot of times it’s just being a customer in an interview. I’ve also helped other teams with videos, webpages, presentations, and final pitch strategies. The point is that by helping people, you can meet new people and everybody is the better for it. By asking for help, you can meet new people and everybody is the better for it.

You are the average of the 5 people you hang out with most. If you want to “BE AMAZING” (inside joke for the MySelfTrainer team Fall 2012, and all the confused people in the audience), go to places where amazing people hang out. Bonus points if you ask amazing people where they think the amazing places are and who the amazing people are.