Alex Weinstein
On Growth, Product, and Leadership
Hackathons at Startups: Creative ‘Fresh Air’

This article was originally published as a guest post on Geekwire; it is republished here for the readers of this blog.

Every now and again, we hear about hackathons: Startup Weekend, Facebook’s famed all-nighters, Hack Week at Dropbox.

However, in a startup, it’s so difficult to imagine how organizing a hackathon can be anything but harmful: “What do you mean, take a couple work days and drop what we’re doing? We’re in a race with competitors! There are holes in our product – and they’re blocking adoption! We can’t just waste a couple days!”

A scene from the recent Sports Hack Day

I know you’re under pressure. That’s the nature of startups.

And yet, allow me to ask you: how many times have you fought an issue for weeks, only to find an elegant solution that takes a day to implement? Have you ever built a feature that nobody ended up using? Have your employees begun talking about the “grind,” the soul-crushing 80-hour-week pace where bugs never end?

If so, hackathons can help with each of these. They let folks take a step back, concentrate on the big picture, and apply their passion – usually where it hurts the most.

Allow me to share a story from Wetpaint. In summer of 2011, we were struggling with our data warehouse system; we’ve had all the symptoms from the list above. This system was so unreliable that our internal customers didn’t trust the data. Engineers were burnt out from every-Saturday-is-a-workday routine. After a couple months of treading water, we realized that we needed to change something structural in our approach.

One key change we introduced was a framework for open-ended innovation. The intent was simple: all participants drop their day-to-day tasks for a couple days, and work on whatever is exciting for them, as long as it has something to do with our overall business. No top-down mandates. Work alone or with others. The only requirement is to show – demo, not PowerPoint! – your results to everyone else at the end.

We called this framework “hack days.”

I was amazed by the results. Initially planned as a morale-boosting exercise, there were _so_many great ideas that came out of it. One engineer’s 2-day project disposed of the majority of the issues we were having with the data warehouse. It took a completely different approach to the problem, challenging some of the foundational assumptions that no one ever doubted. Another engineer built a mind-blowing prototype of a tool that we ended up building over the next three months, and that tool had a significant impact on our bottom line.

Most importantly, this breath of creative, fresh air gave a sustained boost to everyone’s output, even as we re-entered regularly scheduled sprints. We made these hackathons a recurring activity – every quarter, coinciding with company-wide business reviews. Everyone in the company is invited to the debriefs now – and they walk out energized and motivated by the ingenuity of their peers.

Moreover, folks outside of engineering are adopting this framework, too. Our social marketing team, for example, drops their best-practices playbook for a couple days once a quarter, and encourages each team member to try their craziest, riskiest ideas. We’ve seen great results from it.

Give it a shot in your startup. Hackathons can become a “startup factory” in an established company, too. If you’d like help setting up a hackathon, send me a tweet, I’d be happy to help.