Startup Weekend Uncensored

If you don’t know what Startup Weekend is, please crawl out from under your rock and head over to the Startup Weekend website.

Going in I had grand goals of this being the first really cohesive, successful, ahead-of-schedule, profitable-out-the-door Startup Weekend. This bubble burst when I remembered that I hate working with large groups of people. This isn’t to say I dislike a single person within a large group, just that my entire personal and professional philosophy revolves around executing plans with the smallest number of people necessary, and expanding only when necessary. Starting off with 120 people was … new to me.

I was reminded once again that leaders are not self-selected and instead rise naturally within their environment. The first night there was a separate project manager group (of over 20 people), which I volunteered to be project manager of. (Talk about unnecessary hierarchy!) As the “managers” independently thought up task assignments and milestones, leaders within each of the other groups rose and did the same thing, and by the end of Friday night each group was literally hours ahead of the arbitrary milestones the project management group had set for them.

If we didn’t have a 54-hour time limit, of course a core team should define the problem, specify roles, set milestones, and designate team members to take on various tasks. But we did have a 54-hour time limit, and the entire team was not going to spend all of Friday night (the equivalent of three months’ time!) waiting for direction. Instead, they leaped into action, which is exactly what they should have done. In my eyes, this made the existing project manager team unnecessary. The fact that most of the project managers from Friday didn’t even return for the rest of the weekend, or arrived late/inconsistently, made it even clearer to me that assigning outside managers who were not deeply ingrained in a specific group was not the way to go.

When I got home late on Friday night, I shared my frustration with alums from other Startup Weekends, who shared that no separate project manager team had even existed at their events. I ultimately decided that first-thing Saturday morning I would suggest to the project manager group that we disband and be absorbed into teams of interest because every team already had leadership. No one disagreed with me, and that was that.

To the person or people who decided to bitch to the rest of the group that I had “fired” the project managers: speak up or shut up. I’m not a dictator. You were free to disagree, and you didn’t, which made it a team decision. You irk me, and your infantile behavior will be remembered should our paths ever cross again.

What I think would have worked best, and what I would like to suggest a future Weekend consider, is to divide into skill teams (design, UI, development, legal, biz dev, and marketing) and have each team decide on one representative within the first hour. Those representatives would then make sure their groups had something initial to do (like choose a programming language, for the dev team) while the reps quickly defined their respective areas and checked for overlap.

The other main divide I noticed was because of people’s differing goals for the weekend. Some people just wanted to schmooze, others wanted to treat this as a practice exercise, and others wanted to be serious about the idea’s potential. It would be an interesting experiment to divide people by their goals, too. Ultimately I decided that since most people who were sharing strong opinions one way or another weren’t going to be involved past Sunday, most real decisions would be made by the remaining core team, and I’d look at it as more of an exercise to find out who I worked best with.

From this new perspective, Startup Weekend blew my mind with wonderfulness. I have coffees and dinners scheduled out for weeks with interesting, hard-working people. The *worst* case scenario is I’ve made some new drinking buddies to bounce ideas off of. I can live with that worst-case. I got to know my existing Twitter friends Deepak, Lindsay, and Matt even better and converted Andy, Matt, Nathan, Bruce, and Aviel to the Twitter cult (or at least bumped up their Kool-Aid consumption).

I also got to learn a lot. It’s not everyday I get to sit next to a Wharton MBA and build financial models. My time on the finance team was hugely rewarding and gave me new ideas and perspectives on a lot of the existing models I have for businesses in my Idea Box. I’m SO glad I chose a group I was not all that familiar with, as opposed to an area I had a lot of experience with.

Would I do it again? Yes, in a heartbeat. But what I’m most looking forward to are the relationships that are going to stem from this initial weekend.

A million thanks to Andrew Hyde who is all-around awesome, intelligent, and talented and without whom Startup Weekend would never have existed.