Law & Order: Startup Weekend

In the world of startups, the teams are represented by three separate yet equally important groups: the developer, who get a tan from the glow of their laptop screens; the businessperson, who talk about random concepts of revenue streams and profit margins, and the designer, who’s probably on Twitter right now. This is one of their stories.

7:15 OR SO

In the few minutes since I’d been convinced to pitch my idea at Startup Weekend, I’d mentally written down a couple of bullet points-reverse Foursquare, let me know when a place I want to visit is in an area where I’m usually not-and I thought I’d have no problem winging it for 60 seconds. Plus, I’d talked to a few people about the idea, and people seemed generally into the idea, so I figured I’d feed off the energy and have at it. So they called my name, I walked to the front of the room…and my brain went completely blank. So I started with a joke. 

“Hi, my name is Dwight. You can find me online at Why Because there are literally no black art directors in this fucking town.

Big laugh. In fact, people kept coming up to me all weekend, and told me that they couldn’t remember my name, but they either remembered my website, or wanted to tell me about the one black art director they did know. I think I might schedule a Meetup for the six of us. I was kicking myself for not having those new cards printed up all weekend. 

The pitch went terribly. I stammered out the idea, I think I said “reverse Facebook” instead of “reverse Foursquare” at least twice, and I ran out of time. Sixty seconds goes really damn fast, especially when you’re not prepared. 

There were some really fascinating pitches-a Deviant Art-type site for writers, I Bet You A Million Dollars-an app that keeps track of silly arguments between you and your friends, so you have a quantifiable number of who’s right on said silly topic, Seat With A View-a service that helps you find the best seat on a plane, or train, and Startup Superheroes-an online RPG-type social game where you create a superhero or villian, then battle your friends to take over the city. But there was one that I was drawn to even more than the others. 

The idea was beautifully simple-you’re out somewhere, and you think of a friend or loved one, and want to surprise them with a gift. It was called Surprise. 

Phillip, the guy making the pitch, made my pitch seem like a Steve Jobs keynote by comparison. He stammered, talked all over the place, and didn’t really have a handle on what he wanted to say. But you could tell he was passionate about his idea. I wrote it down in my sketchbook. 

After the pitches were finished, we voted on the pitches we’d like to work with. I didn’t even look to see how I did, but a number of people came up to me and told me they liked the idea, liked my energy, voted for it, and told me I should pursue it regardless. Which, by the way, I’m definitely going to do. 

They called us back to announce the winning pitches. My pitch didn’t win. Surprise, however, did. Phillip was clearly shocked. When we were finally allowed to go pick who we worked with, I briefly considered joining the Superheroes team. A few groups actually tried to recruit me to be in their teams, which was really cool. But I kept gravitating back to Phillip. Plus, I didn’t want to be just a cog on the wheel-the Superheroes guys snapped up three creatives-I wanted to jump in and really tackle the concept creatively, and considering Phillip was surrounded by three developers, I thought I’d have the opportunity to do that. We had creatives, and developers. What we were lacking in, were business people. Hakon Verespej, one of our developers, and actually the first person I’d met this evening, ran off to recruit some business folks. Our group grew. And kept growing. And growing. 

10 ISH

Before I knew it, there were thirteen or so of us crammed into a stairwell, shouting over another, trying to brainstorm and figure out what Surprise would become. 

As a creative, I’m used to brainstorming in groups. The one rule in brainstorming is, you’re not allowed to say “no.” Always “yes, and”.  The worst thing you can hear when you’re brainstorming is, “Here’s the problem with that”. That does nothing to further the discussion, only serves to frustrate the person offering the idea, and derails the brainstorming. We were hearing that a lot. I had a problem with that. 

We ended the evening not very far from where we started. We’d lost three valuable hours bickering, and I didn’t see much of a future with this group. We were way too big, and there were too many Type A types, and Type A wannabe types that were causing friction. I think there were a couple of people who felt the same way, we lost a couple of people that first night, but still had a large group. I considered leaving the group myself-this wasn’t going to be fun if the whole weekend went like this. I thought, maybe I could come back and just kinda offer my services as a floating designer, helping out where I could. At least I’d get something out of this mess. 

I left Friday night feeling very down on the prospects of this project, and this group. 

9:00 AM

I’d decided that I’d go back into this with an open mind. This is a learning experience, after all, and I can’t run away from situations like this. I’m always going to have to work with people I’m not compatible with, and I’ve dealt with clients worse than this. (To any of my clients reading this, I’m not talking about you.) But I thought I’d break the ice with gifts, so I brought in about four pounds of candy for my team and all of the groups and dumped it on the table at the front of the room. I kept the Peanut M&Ms for myself. Those are my creative fuel. Can’t design without my Peanut M&Ms. Plus, the protein in the peanuts cancel out the sugar in the chocolate, so it’s almost diabetic-friendly. (This is probably not true.)

9:30 AM

The group had arrived, and we had already picked up where we left off last night. One of the developers asked me, “can’t you start designing something?” I replied with, “what the hell am I designing?!” We had no focus, we were talking about everything from who we were trying to reach, to business plans, to revenue models. Everyone was overwhelmed, nobody had a task, and again, we were talking over each other. Attempts to reign in chaos were futile. At one point, our project manager, Dani Harder, held up an orange and said, “whoever holds the orange gets to talk. No interruptions.” Which worked fine, until one of our business guys, Ken Decanio, talked so long, that he started eating the orange while he was talking. I’d had enough. 

“Okay, listen. I need to go do something. Someone give me the name of the business, and our fifteen second elevator pitch, and I can go work with that.” 

Phillip spoke up. “The name is Surprise. The pitch is, it’s a fun way to give gifts to your friends or anybody.” 

“Fine. I’ll go start working on a logo or something.”

Hakon stepped up, and took charge of the developers (himself, Michael Brooks, and Dwayne Mercredi), and they started tapping away at their laptops. Gerry Chu, a great UX designer, and Phillip huddled in a corner and started talking about how the app would function. The business team (Dani, Ken, Rob Gropper) went to another corner and started immediately bickering about business models. I found a corner of a table and started sketching. Finally, we were moving in some kind of direction. 

I came to a realization at this point. While Phillip was a creative (and a great one, having worked for Amazon in their early days), he was also the leader of the group. He had to manage everything. Which left one guy to design the logo, come up with the brand, design the UI for the app, and pull it altogether. On a Startup Weekend devoted to designers. Where  Jenny Lam, the person who inspired me to not bail on this at the last minute, would be sitting in about 35 hours, judging the design. One guy to handle all of that. 


Oh shit. 

Coming Tomorrow: We continue to surge ahead, while the threat of looming snow threatens to take half of our development team. The app begins to take shape, and we figure out a revenue model when we start charging people money to look out the window to see the snow.