What I learned at Startup Weekend SF: Agility is the state of nature

What's a good mother/son spring break activity? Why, going to Startup Weekend and spending 50 hours building a company with ten total strangers. Perfect because my 17 year-old vastly prefers the company of adults to that of other teenagers, and because he's been on the high school treadmill for so long that I thought it would be nice for him to see what the light at the end of the tunnel might look like–that the world of work can be a rather thrilling place.

Several years ago, I visited the very first Y Combinator class of college-age founders when they were only six weeks into their startups and was astounded at the number of fully functioning products. Turns out six weeks is an eternity, way more time than you need to build and launch a startup!

This weekend, 150 of us crammed into a giant room in Microsoft's Market St. facilities. We were given lots of food (thanks to Sana of Women 2.0) and very little direction. After a free-form round of idea-pitching, with coaching from the lovably dyspeptic Dave McClure (our team-member Han Pham describes his style here), we were cut loose to self-organize into teams.

Tyrone and I were interested in Connor Lee's idea for a venue-rating site for event planners (easy to build in a weekend), and Julian Bryant’s pitch for a site that would allow people to interact around pending legislation. As it turned out, Connor, who had legislative experience Tyrone and I all joined Julian, along with developers Marcus Phillips and Philipp Pfeiffenberger, SEO/Social Media/Web Marketer Aris Vlasakakis, marketing gurus Sherbeam Wright and Mariam Ishpahani, journalist Han and a couple of others who came and went over the weekend. Julian emerged as the natural leader, as well he should being a former Senate intern and Georgetown Law grad with a startup around language learning.

I have worked as an employee or long term contractor on three tech startups, one VC funded, one angel funded, and one bootstrapped. This team outshone them all in terms of raw talent, intellectual horsepower, organization, distribution of skillsets, commitment and efficiency. And we were not alone. In all, 23 teams had working demos or prototypes to share on Sunday evening, and a couple had actually launched fully functioning products (I was using Snoozemail in my gmail inbox before the evening was out). There could be no better demonstration of the power of self-organizing teams than this display of exponential creativity and productivity.

Marcus and Philipp–both Y Combinator alumni if I'm not mistaken–were curious about Agile, and we talked about it a little bit, but there really wasn't time to talk about anything but pushing our product out the door. What I found enlightening was that their native values, instincts and practices were inherently Agile. Being Web 2.0 guys who work in Ruby and Python, they have never been exposed to Waterfall. (The only team that did anything resembling a Waterfall process was the one team that had absolutely nothing to show on Sunday, having spent all their time creating specs.)

This makes me think that perhaps the best way to promote Agile is to take a cue from crime prevention and literacy drives: don't focus on reforming those who have already been "lost" to Waterfall methods; focus instead on preventing the destruction of our talent pool in the first place!

Our team, christened "Democlarity," divided rather quickly into two right-sized sub-teams (also quite Agile). Tyrone went with the bus dev side, working on business planning, market research and content creation, while I went with the development side–the first time I've ever worked on a project and not been the writer/editor. I did some HTML wireframing, then turned my attention to CSS styling while the devs blasted in the functionality.

We had technical difficulties here and there–the wifi broke, version control broke, my host account where I was hosting images while designing went down at a critical point. Marcus and I paired on merging the disparate html files, then Philipp and I paired on some last minute CSS (he is 10x faster than I am, so my main contribution was saying things like, "Can you make that greener?").

Everything  got done, and Aris and Marcus had time to practice their demo pitch. We weren't live online, but we were certainly way too cool for powerpoint, and were able to show a site with functionality and an amazing amount of depth.

Aris and Marcus rocked the demo, with Phllip driving the mouse so they wouldn't have to break their patter, and we disbanded feeling like we'd accomplished something fairly spectacular and been a part of something pretty important. The Democlarity team is looking forward to a reunion in a month, and plan to continue developing what we started in an open source-ish sort of way. In the meantime, a demo of our site should be up on www.democlarity.com fairly soon.

Tyrone went back to swim team practice today, and I'm back at work too. But I learned more about teams and teamwork this weekend than I did in the previous year–and that's a year in which I wrote an Agile training manual and helped organize the Orlando Scrum Gathering's Open Space Conference. I'd highly recommend the startup weekend experience for anyone who is seriously committed to working on or with software teams–the pressure of an insane deadline like that compels you to strip everything down to the purest, simplest form: communication, decision making, work flow, product features, everything, and conversely, it also leads one to discover the enormity of one's own personal resources. We were like those people who, in a crisis, lift a car off of a person. Heady, empowering stuff.

This weekend was Startup Weekend World, with 50 cities participating. There will be another soon enough. Hope to see you there!

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