How to Win at Any Startup Weekend

Winning at Startup Weekend

Startup Weekend Evansville is part of a global network of events where people come and pitch a business idea on Friday night, work and sweat and learn all weekend, and Sunday night pitch the business plan. There is a panel of judges made up of local business and community leaders that pick the top three pitches. The winners get a variety of things donated, such as legal services, office space, business services (like web hosting from Lieberman Technologies!) or other things that would help them launch their 3-day old startup.

This year was the first time I went, and I brought a whole team. Both of my two teammates were a little nervous. Other than some cat-sitting for a neighbor and mowing a few lawns, their experience in business was minimal.

My teammates were my 13- and 15-year-old sons.

The way a startup weekend works is that anyone can give a 60 second pitch on Friday night. After the pitches, there is a voting session and everyone has 3 votes to give. The 10 pitches with the most votes become teams and everyone joins one of those 10 teams. At the advice of Startup Weekend facilitator Dana Nelson, we divided and conquered.

I told my boys to do what has always been a good practice for me: get into the middle of the action and just listen. They did a great job. Even though there were 99 attendees and only 5 of them were under 18, they dove into the thick of the crowd and listened to conversations. The people that were open and interesting to 13- and 15-year-olds were a natural match, of course. Still, at the end of the Friday pitches, they were unsure which team to join — but by the end of the night they both had a team and introductions, and they made clear to their teammates what they could contribute and what they were looking to gain from the weekend.

Since I was there as a coach, I circulated from team to team, moving all of them along toward their final presentation on Sunday night. There were three things that I observed in the successful teams.

Three Things that Winning Startup Teams Have in Common

1. They spent their time working towards a target instead of deciding on their target.

On Friday night there were 29 pitches. The teams that did the best grabbed that Friday night pitch and focused it, refined it, and then stuck to it. While some teams were still trying to identify their product or the problem they were solving or who the customers were (which they would then allow to change the problem and the product) there were other teams coming up with more answers than questions because they kept their focus. Startup Weekend is full of milestones and deadlines, and if you make the decision to cross them on time and not go back, you’ll meet the next deadline much easier.

2. They used every member of their team.

Startup Weekend is definitely a melting pot of smart people, but when they are NOT at Startup Weekend, smart people sometimes fall into isolation. The teams that thrived had everyone involved. Every person on the team could explain the goal, the purpose, the methods, and the outcome of their business. Even if it was rough and they didn’t have content or research to back it, they understood where they were on the team.

3. They only tried to create the MVP (Minimum Viable Product) over the weekend.

While there were teams making complete WordPress sites and prototypes, there were other teams that understood the “startup” side of Startup Weekend. If you can pitch the company and start the business strong, you’ll have the longevity to do the R&D that is needed to get the product to market. Identifying what the deliverable was early and working towards that and only that all weekend turned out to really help the teams that won.

Winning isn’t Everything

How did they do? Since I wasn’t a judge I couldn’t show my boys’ teams any favoritism. I had the joy of treating every team like they were my own and cheered each of them on during the final presentations.

Over dinner, while the judges deliberated, the boys and I talked it over and I was glad to learn that each of them was confident about his own team winning. (I was considering how to walk them through losing as they were prematurely but conservatively celebrating!) As it turns out, both of my sons won — my oldest son on team #1 with a drone thing and my second son on team #2 with a night vision thing! Our whole house was pretty excited when we got home. I’m not sure how much involvement they are going to have in the future with the teams they were on, just because of the nature of startups and school, but both of them spent the next 3 days talking about what startups they are going to launch next year at Startup Weekend Evansville 6.0.

Which brings us to the TL;DR of how to win at Startup Weekend. Go, follow the three tips I listed above, and take your kids and your friends. You might not win the award, you might not create the next big thing, but you’ll win a great experience and a lot of knowledge, and that is always a win in my book.