Startup Weekend: Day 1

“Okay, Dwight. You’re up. Sixty seconds. Go.”

Shit. I forgot how much I hate presenting.

I came into this Startup Weekend experience with no idea of what to expect, how I’d be received, or how many designers would be there. But like I said yesterday, I jumped in with both feet. The old Dwight the Mayor was back, and I was bouncing around the room, soaking up all of the energy. Most of the people I met were also first timers, so that made the experience a little easier to take. A lot of people were working on their pitches, and a lot asked me if I was planning to pitch. 

I had an idea that I have been kicking around for a while. Last year, I was reading Esquire’s Best Bars in America, and while there was one bar in Seattle, I would have loved to visit the other 49. But the reality of the situation is, I don’t know when I’m going to be in New York next, and when I do get there, I’m not going to have a copy of this magazine with me, and I’m probably not going to remember what the bar is. So my app would take that information, sit on it, then whenever I’m in New York, send me a notification that, “hey, remember that bar you wanted to check out last year? It’s here, go check it out.” It’s kinda like a reverse Foursquare. 

I told a couple of people about my idea, and there was some good feedback. A couple of people even offered ways to add on to it. This was great. This was the collaborative experience I wanted to get out of this. My first rule of brainstorming is, nobody is allowed to say “no”. You say, “yes, and”. Don’t shoot down and idea, see how you can build upon that idea. I had a couple of people who got this-mostly designers. I got a few people who didn’t-mostly developers. 

The time came for the pitches to start. I was sitting next to an illustrator named Ryan, who started out designing posters for his band, loved it so much, that he’s now trying to make it a career. I told him about how I lucked into this Startup Weekend opportunity, and how I was just spending this year trying as many new things as I can. He asked me if I was going to pitch. I said, probably not, but we’ll see how it goes. 

He says, “But didn’t you say to always say “yes” to things? Isn’t that why you’re here?”

Well, shit. 

So the pitches start, and there are some brilliant people in this room. Most of them are incredibly awkward in speaking to other people. You only get sixty seconds, so you have just enough time to say your name, your idea, and what personnel you need. Most of the people had prepared notes, practiced their rehearsal, timed themselves, and all that. I was going to go up there and wing it, basically. 

I saw my name creeping up the pitch list. My heart started beating out of my chest. I needed to channel that old Underdog Dwight, the guy that can work a crowd like nobody’s business, or this would be the longest minute of my life. 

My name came up. I stood up, took a deep breath, and walked to the front of the room…

Coming up next time: Did I control the room, or fall on my face? Did I get in enough plugs to this site over the course of the night? Only my Google Analytics knows for sure. Did my pitch get selected, and I begin the process to taking over the world? Stay tuned…