Thoughts about Startup Weekend

It’s taken me a few days to gather my thoughts about Startup Weekend (and ok, I was slightly distracted by the snowpocalypse this week).

I’m not going to give you a play-by-play because I’m not sure I could improve upon Dwight’s perfect summation (part 1, part 2, part 3) – he really captures what it was like to be there and be involved.

I had said before in my previous Startup Weekend post, I was a little nervous because I didn’t know what to expect. Some of my fears were confirmed, but I was pleasantly surprised in many other areas.

First, my overall experience was incredible. Everyone (literally everyone!) there was super nice, really excited to be there, eager to meet you, find out about you, etc. It didn’t matter who you are or what you do – people were enthusiastic talking with you. Definitely a very friendly, gregarious crowd.

Based on the raise-your-hand survey at the begining, it appeared that most of the room were first-timers which was surprising. For some reason, I expected more grizzled veterns.

One of the other things I was surprised about was the amount of abandonment by team members throughout the weekend. I heard that other teams had people leaving because they couldn’t get along or didn’t want to take part any more. Even on our own team, we lost one person the first night, and one person the second night. So strange!

As for my team, there were some really talented people on it. Our team leader and pitch’er (Eric Butler) turned out to be the guy who wrote FireSheep (Firefox extension that demonstrates HTTP session hijacking attacks) which made a big splash when he released it, so he’s famous! (well, internet famous – at least to technical people). I didn’t know this when I first talked to him about joining his team, but I was certainly impressed when I learned this.

But that basically confirmed my worst fear – being on a team with tons of über-level talent. What exactly could I contribute? Even worse, the code was being done in Ruby on Rails, something I have ZERO experience with. I spent quite a bit of time getting my own RoR setup configured and running our source code which is another post in-and-of itself. Ugh!

I contributed what I could in various other aspects, but I did feel a little marginalized. It’s clear Eric had thought about this idea quite a bit, including researching competition, sketching wireframes, mocking up icons, and figuring out how to monetize it. This being my first time, I surely didn’t want to overstep my bounds or step on any toes by trying to take on too much oversight.

Here’s a guy who has a lot invested in his project, and extremely busy writing the backend code, and seemingly did not want (or is not able time-wise) to be the project manager, but also did not want to relinquish control of the project – it was definitely an awkward situation.

I was ok being a cog-in-the-wheel the first time around though. In retrospect, it was probably a good thing that I didn’t get thrown into the deep end and being primarily responsible for the technical aspects of a project. I got a chance to see how the process worked (and how I might handle or manage the process differently) and it was a very valuable experience.  I did find out at the end that there was at least one team that didn’t have a developer though. I wonder how it might have worked out if I’d have found that out and migrated to that team? I’m sure it would have been a completely different experience!

There were some incredible teams coming out of the event – some teams I thought were well on their way to forming an actual company and making a go of it.

In the end, I really had a great time – met a lot of great people, got some extremely valuable experience that I will be applying to my next Startup Weekend:

  • I will definitely blog/photograph/tweet more. Documentation!
  • I will definitely take notes (and possibly even photos) during the pitches. I had a hard time remembering all the pitches, what they were about, who pitched, etc. 54+ pitches in an hour or so – very hard to keep track of!
  • I am definitely going to pitch next time! I don’t feel bad that I didn’t the first time around, but now that I have a better idea of what pitching is all about, it’s something I really want to do.
  • Picking the right team – pick a team that you can contribute to, and something that you feel strongly about.
  • Confirming that I really need to tighten up my technical chops in some areas that I’m lacking (especially front-end work)

My last thought: this SW was held at in Pioneer Square so I was wandering around the streets morning, noon and night. I can’t believe how far the area has fallen with regard to hustle and bustle. Granted, it was the weekend so maybe the foot traffic was less than it might be during a normal 9-to-5 weekday but Friday and Saturday night were D-E-A-DEAD! I remember back in the 90’s when it was THE place to be, and now, nothing. No one in the bars, no one walking around on the street. Nothing. How sad.