Lessons Learned from Startup Weekend

A year ago this month I attended startup weekend in Boston. The company that I helped to launch there, http://sellercrowd.com, is now a successful ongoing concern, with funding and a handful of employees. So I think that counts as a success story for startup weekend, and my conclusion is that it’s a great program and can work well if you make the right choices going into it. To that end, I’d like to share some of my lessons learned from my first startup weekend, and solicit anyone else to add them in the comments.

First, always come with an idea. Create a good pitch. This is the way the other participants will know you, and it’s worth giving them a chance to get a sense of you in this context. You don’t have to bring your best idea to startup weekend, but it helps if you can bring your best startup weekend idea.

Second, don’t be too attached to your own idea. In fact, you might get more out of this if you can join another team that has an idea that is even better suited to startup weekend than your own. Very few good ideas can be implemented and validated in 48 hours. Plan to pick the best one, and don’t worry if it isn’t your own. You can always take what you learn and apply it to your own idea on a more practical timetable.

The best ideas have a few unique characteristics that make them fit into the timeline, audience, and competitive aspect of Startup Weekend. A few principles of idea selection:

  • Select an idea that fits into a weekend. Ideally you will want to validate your idea with customers, build a prototype, validate more, prepare a demo, and make a presentation. That means you can’t invent any substantial new technology, you are looking for something that is class-project sized, not 20 engineer months. If you have a big idea, cut it down until it feels like it might fit, then cut it down by another two-thirds.
  • Appeal to the audience. Present an idea that people in the room will want to use. That makes it easy for them to understand and get excited about, and will give you your first customer validation. The people in the room will nearly all be younger professionals in the tech sector. Ideas related to socialization, recruiting, and personal services are easy to get excited about. Ideas related to financial risk management or construction not so much. Surprisingly, medically oriented ideas got people pretty excited, I think because “doing well by doing good” is hot. Feel free to trend-follow here.
  • Appeal to the judges. It’s a competition and people like to win. Choose an idea that can be validated in a weekend. You probably won’t get any CFOs on the phone on a Saturday, but you can go outside and find consumers. Don’t choose an idea with huge market risk, or where your team will be clearly unqualified. Choose an idea that resonates with current investing trends, with an additional hook.
  • Explain why you are the leader. Ideally come with some kind of pre-validation, and include that in your pitch. “I already have a list of 20 prospective customers who are willing to do interviews this weekend, and I need people to do the interviewing and build a prototype based on my vision and feedback” makes your idea feel much more achievable and worth joining.

When you are selecting an idea (including if you select your own), you are actually selecting a team. So if you can find someone with an appropriate idea, a great idea, who also has the personality or presence to pull together a team of people in the chaos that is startup weekend, all the better. The number one thing you are looking for in a team is a good breadth of skills and a good number of people, enough people and skills to get something real done and have someone paying attention to all the parts.

Beware of teams with only 1-2 engineers unless the idea is super simple, and avoid teams with more than 3-4 business people. If your idea needs a designer, your team needs a designer. In my experience, the designer was the most valuable member of the team (even though he hadn’t ever done startup web design before) and the rarest find. The Startup Weekend organizers try to keep the skills balanced, but it’s never perfect. Too few engineers and your engineers (maybe you) will be death-marching for the weekend. Too many business people and they will be off on distracting tangents.

Usually you are going to be implementing some kind of application, web or mobile, whether it is a prototype or not. Choose a team where the engineers have good skills overlap and can quickly converge on a technology (e.g. Ruby on Rails, Python Django, node.js and seven other libraries). Avoid science projects. Avoid any devops, host on Heroku or someone’s personal machine or whatever someone already knows. We lost 3 engineer hours to fighting with Amazon hosting, which was completely uncessary. Choose technologies you know and that you know to work, and focus the risk on the application you are building and the ridiculous timeline.

Speaking of building things on a ridiculous timeline, the best advice is to begin with the end in mind. Know what you are going to be doing at the end, which is presenting for 5 minutes to a group of VC/Angel/Entrepreneur judges who will want to see that (a) you build something impressive, (b) your idea is coherent, (c) there could be a business here, and (d) that business would actually do something important. To that end, start building a demo script and a PowerPoint as soon as you have converged on what your idea is. Make sure that whatever you build as a product supports a well-scripted demo, and that whatever work you do around customer validation fits into the pitch.

Finally, don’t sweat the ownership until you have something real. This is the trickiest aspect of startup weekend. Failure is an orphan but success has many fathers, as they say. In our experience, having created something successful that was on track to get funded, we were able to more than satisfy those people who helped at startup weekend with a token amount of stock (a few hundred shares) once we made clear the additional work that was going to be required. Of course, it is always possible for someone to make a stink, and this is why you should be careful about what ideas you choose for startup weekend.

I hope these tips are helpful to anyone doing SW, and if you have more please add them in the comments. I encourage everyone with an interest in startups to try out Startup Weekend. The environment is very high energy, and you get nearly immediate feedback on what you are doing. Concentrated learning and coworking in such a short period of time is great fun. And if you are lucky, you may come away with a startup you are really excited about.

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