In some ways it’s like The Breakfast Club. In more ways it’s completely different. Meet some new people with different backgrounds and throw them together for an extended period of time. And before it’s over do something you never dreamed possible.
OK perhaps I exaggerate a bit, but that’s probably the best way I could explain the events of a Startup Weekend to anyone who’s never experienced it first hand. Self touted as “a 54 hour event that brings together designers, developers, entrepreneurs, and experts from all domains to do amazing things,” I joined on a whim. Wanting nothing more than the experience of stirring things up and doing something I’ve never done before. Armed only with my wits, a CS degree from many many years ago, and a career as a corporate IT-ist, I soon realized that I was both not prepared for what I got myself into, and at the same time more ready than ever to push past my comfort zones.
For the uninitiated, all Startup Weekends follow the same basic layout. Show up on a Friday night, start networking among the crowd over dinner, hear some folks talk and get ready to go. You’ll either pitch your own idea or just listen to everyone else’s, pick teams and work your butt off until Sunday night when you present (and be judged).
Pitch. Or do not. There is no try.
Have an idea for the next big thing? You’ve got 60 seconds. Grab a mic and go for it. Many if not most of the people who pitched this night clearly had been preparing for this. I however had not, other than passively thinking about a couple, two, three things over drinks or randomly with people I knew. With nothing completely developed or practiced I threw myself in the first group of four to take my minute, and I bombed massively. How I even got the few votes that I did is beyond me (and I swear I didn’t vote for myself) but it was quickly clear that my weekend role would be as an enthusiastic but slightly-out-of-his-element team member.
On this night the top six ideas based on group voting bubbled to the top and the mad scramble to pick teams and recruit troops occurred. As for me there were really two that caught my ear - the first ultimately having a lot of interest with the participants, and the second with a small but excited group of folks jelling together. A little internal back and forth along with the night’s organizers announcing that we should have picked our teams already, and my decision was made. Not wanting to get lost in a big group, I chose the smaller team hoping to have a bit more impact.
Getting down to business.
Turns out our group of six ended up being pretty well balanced. The lead, a couple of devs, a couple of marketing folks, and….me. The…corporate…IT…guy? Holy crap what did I just get myself into. No turning back, the team got right to work brainstorming around the original concept and soon enough agreed on out initial plans, site layout, user flow and next steps. Wow, this is going surprisingly well. Venue closes at eleven we’re told, and shortly I’m on my way back to Union Station picking up a bag of fries along the way, waiting for the last train out which would end up being after midnight.
Finally getting home around 1:30 in the morning, I pet the dog and give my sleeping kids kisses on their foreheads. Whip out an email to the team right before finally taking a breath, and think about how these next few hours of sleep are going to have to hold me over because I need to get on that second train back into Chicago in the morning, and..what am I doing again?
The need for coffee will be high.
Second train into Union Station Saturday morning. Not too rested, but my mind is preparing for the long day ahead. Gonna put in some work, today. I think to myself. I’m pretty sure there’s gonna be coffee there, but I need to get my systems revved up now. By my informal count, I passed at least three Dunkin Donuts, three McDonald’s and four Starbucks on the way from Union to the event site. No excuses for not having coffee.
It’s a bumpy start to Day Two as our marketing folks get caught up and delayed on the way to the event, but the team quickly buckles down and starts divvying up assignments. The classroom turned war room is abuzz with keyboard typing, multiple conversations, and phone calls to peers and connections gracious enough to call us back on a Saturday morning to provide validation feedback. One thing that sticks in my mind as the team weaves its way back and forth, coming together for alignment with each other before splitting up again to tackle our respective tasks, is that for a group of Startup Weekend virgins, we’re surprisingly cohesive. While no one disagrees that it would be nice to win, we’re all really here to soak up the experience, looking more for personal growth within a team focused on a goal than wanting to check off a win column. (But, winning would still be nice, right?)
Quite honestly the rest of the day is a blur. Coaches of various backgrounds come in and out with (generally) constructive feedback and suggestions. Some hang out longer than others, and a couple were definitely worth their weight in gold. As the day trudges on, and with one eye focused on the final pitch criteria, the breaks are short and the work is hard, a flurry of conversations on demo functionality, customer acquisition, revenue models, a quick team name change, and ‘seriously does anyone need more coffee’ fly back and forth, the sounds of downtown filtering through the windows into the background of white noise as the clock continues ticking, final pitch time creeping closer. We have a plan, we’re sticking to it, and it’s all pretty much coming together. Sleep is for wimps, the MVP is done and we’re halfway home. Except that when the adrenaline fades and the high octane coffee loses it’s efficacy, the train ride home feels a little longer and all your thoughts start slamming together. I’m missing something. Do we have everything covered? My head hasn’t even been on the pillow long enough to warm it when I get back up and head back into town, but not until I stop somewhere to get some more coffee.
Sunday Sunday SUNDAY…
Even with the long hours and late nights, no go-live I’ve ever done in my day job came close to the frenzy that built up in those hours leading up to the final pitch. Basically everything we had done starting at six Friday evening came down to five minutes of presentation and demo. Practice pitches, last second slide and demo changes, and a tech check gone eerily bad wasn’t going to stop this train. The laptop that went to sleep five seconds into the final pitch? Keep your cool campers, it’s not over til it’s over. Five minutes means five minutes. Cranky because you’re tired and you haven’t had lunch yet? Suck it up, you’ve got four minutes of Q&A. Get past that and you can sit back with some cold pizza and let the chips fall where they may.
No prize for second place.
Except when there is. When all was said and done, the team did a solid job on the pitch. No hard hitting questions from the judges - mostly clarifying things we spoke of during the presentation - you could see the distinct change in posture in all the team members when we finally put it to bed and watched the other teams do their thing. All in all a respectable showing from all six teams that worked through the weekend.
My team placed second that evening for Pairs, which is a collaborative tool linking students together to work on assignments. Multiple student sessions based on assigned pairings can run simultaneously while a teacher can view and monitor all the running sessions on their own dashboard. A week later, we’re still fielding requests from folks asking for more info on the product, and the team is dedicated to seeing this through.
Afterthought
Personally Startup Weekend forced me to push my boundaries. To be thrown into a mix of folks who you just met and have to work through a whole business and product development cycle in a weekend? That’s like the team building exercise from hell, but I’m thankful that our troop of folks jelled together so fast. We may not have had a whole lot of people, but the team was pretty balanced and that was tremendous when splitting up tasks. The team is everything in this kind of event and if the team makeup was different who knows if we would have synced up the way we did.
Not to be anal, but…
As I said earlier, Startup Weekend touts itself as “a 54 hour event”. But for the teams, when we’re just starting to meet around 8P on a Friday, and final pitches start at 5P Sunday night, that leaves less than 48 hours to get your stuff sorted out. No pressure though.