Portland Startup Weekend: Takeaways

How my team succeeded at Startup Weekend.

Quinn Rohlf · 28 Apr 2014

Portland Startup Weekend is an idea that sounds good at first, but when you really think about it is completely insane. Pitching, building, and presenting a business in 54 hours isn’t just challenging, it’s sheer lunacy. Fortunately, there seem to be quite a few talented entrepreneurs out there who are willing to sacrifice their weekend, their sleep, and their sanity to participate in the madhouse that is Startup Weekend.

This year marked my second time as a Startup Weekend participant. Last year I was a developer on the LivFly team, building a platform for people to find running partners online. I learned a ton from that experience, and this year I pitched Spoke.coffee, a service to deliver local and fresh coffee and other goods straight to customers via bicycle. LivFly received top honors last year as the overall PDXSW 2013 winner, and this year Spoke.coffee took home the award for best customer validation.

To me, Startup Weekend isn’t really about the business ideas or even the apps and websites that we build. It’s about the experience, and the huge learning opportunity that experience represents. Even if Spoke.coffee doesn’t continue past today, I’m 100% satisfied with what it accomplished. Our development team got to experience the process of building a web app from start to finish. Our analysis people cut through all the unknowns to figure out how to model our business and translate those models into strategy-changing insights. Our designers worked on challenging projects with absurdly short turnarounds. And as the team leader, I can unequivocally say that I learned more about how to organize and direct a group with diverse talents in a single weekend than I have learned in three years of traditional college education.

Startup Weekend is about making mistakes and learning from them.

Here are some of the lessons that I’ve learned after two years of participation.

1. Come prepared

Startup Weekend discourages projects that are already partially implemented, and for good reason - starting from scratch is the best way to learn as much as possible in a single weekend. However, that doesn’t mean you can’t prepare by planning out what tools your team is going to use to collaborate and build your business.

At LivFly in 2013, we spent the first day and a half trying to find the right tools to build and launch our idea, so this year I researched collaboration and development tools before giving my pitch. From day one, our team was able to build and collaborate smoothly with Google Drive and GroupMe, and start building and shipping our MVP immediately with Sinatra, ActiveRecord, Bootstrap, Stripe, and Heroku. Having that robust stack of tools and technologies pre-selected meant we were able to skip the boilerplate involved in getting a modern team up and running and jump straight to the startup-building action.

2. Front-load the work

Building a business is exhausting, and people do their best work when they’re fresh. Last year the whole team at LivFly was exhausted when it came time to hammer out a business model and perfect our presentation - We’d been working late on both Friday and Saturday night, and Sunday were all had short tempers and weren’t operating at 100%.

This year, I pushed myself and my team to do as much as possible on Friday night. We stayed up until 3am building our product, and managed to get it finished. Although we were pretty tired when Saturday morning rolled around, having everything built on day 1 meant that we could spend Saturday morning and afternoon doing customer validation, and then go home early and get a good night’s rest for Sunday - arguably the most important day of Startup Weekend since it’s when teams actually ship their products and present to the judging panel.

This is an extreme example - building a business in two and a half days is never going to happen in the real world. However, I think that the strategy of front-loading the work carries over into any kind of project - it’s far easier to finish something well if most of the hard work is finished early in a project’s lifetime.

3. Doing is better than talking

This is the mantra of Startup Weekend – so why am I repeating it here? The answer is that Startup Weekend doesn’t always follow its own advice, and it’s worth remembering that doing is more important than talking when the fifth volunteer mentor comes by to give your team advice and expects you to drop what you’re working on and listen. The Startup Weekend mentors are a great resource, but just like every other resource in a business there is a time and a place for listening to mentors. It’s important to remember that the best way to learn is to learn by doing, and the next time a mentor comes by your table wanting to give you more advice it’s okay to tell them that you’re busy.

We had a problem at LivFly where we listened to every mentor, volunteer, and random person that walked in the door. This had mixed, even contradictory results - even though we had a solid idea of our business model from the beginning, we ended it rewriting it two or three times after being prompted by mentors who often would contradict the previous advice we had just gotten.

The takeaway here is that it’s good to have a clear idea of what you’re trying to accomplish, and to put as much time and effort into doing that thing while minimizing distractions.

Startup Weekend is dumb - but go do it anyways!

Startup Weekend is a completely unrealistic scenario. 3 days is not enough time to build a sustainable product and business model. The judging pool is typically way skewed towards a certain type of business or enterprise, and the prize packages for the winners are a joke (at least at PDXSW they are).

So, would I recommend participating in Startup Weekend to a friend? Yes, absolutely! It’s a great way to learn by experience, and a very rewarding thing to do – long as you go into it with the goal of learning as opposed to winning or starting a real business.

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