«

»

Nov 19

Twelve Lessons Learned from a Startup Weekend

2014-11-16 20.41.59

This past weekend I participated in my first Startup Weekend Columbus.
During the course of which we built Fairflo, a marketplace for fair-trade items. The front end can use some work, but at the end of the weekend we had a fully functioning e-commerce site. I’ll write about the infrastructure separately, but as an aside Saturday night an attack from China was detected and defeated.

In no particular order, here are some lessons learned.

Lesson 1: Remember to take care of one’s self

Startup weekend is incredibly intense. There were approximately one hundred
extremely creative people all in a relatively small space — enough space in which to work, but close enough that creative juices were flowing amongst the groups. It’s very easy to find oneself living off the energy and forgetting to eat or otherwise feed the body. I’ve seen it elsewhere at festivals and conventions. In some senses it was more intense this time — perhaps due, in part to the close proximity; at conventions there are usually panels or other events which help to disrupt at least some of the flow. The organizers were really good about making sure that there was food available; as the weekend progressed more and more energy bars were placed out for the participants.

Sleep and/or other forms of downtime are needed as well.

Lesson 2: Practice the Pitch. Practice, practice, practice!

Given the limited amount of time to present the pitch, timing is very important, particularly if more than one person is presenting. Setting aside a couple of hours to practice and refine the pitch is very useful, especially for polishing and showmanship. Getting up in front of a crowd and talking is far easier than having a concise and succinct message. Providing a block of time is essential for being able to revise, refine, and review. Additionally the pitch should be given, if possible, to someone not on your team — perhaps a “trade” where teams can practice in front of each other.

Lesson 3: Mental Stealth Checks

Given the timeframe and pressure, it’s important for groups to periodically touch base with each other. In some senses it’s like a standup for an Agile team, but given rather more frequently. In addition to what people are working on and blockers, checking the mental/emotional state is very important. I think that a 10-15 minute standup including touching base/emotional check-in of, say, four times a day is probably about right:

  1. First thing in the morning
  2. Lunch time
  3. Dinner
  4. End of the day

It might be helpful if people are getting frustrated/frazzled to have them more often — even just a quick stretch and “Do you need anything” every couple of hours. Any more than that and flow is likely to be disrupted.

The organizers had daily meetups for all of us to touch base and talk about progress and/or needs. I’ll admit I felt a touch of resentment toward the meetups of all the teams — it was eating up time which I felt could have been better used for working with my team. I understand why they had the meetings; it is far too easy to fall down the rabbit hole and sometimes a break and/or change of pace is needed. In the moment, I felt as though it was disruptive of the gestalt which we were building.

Another reason for having these team meetings is to help maintain focus and keep on task — it is far too easy for Creatives to suffer from “Oooh, shiny!” and get distracted or to zoom from one thing to another when under pressure.

Lesson 4: Do high level planning Friday night

A quick high-level plan and/or breakdown of tasks and/or priorities are very helpful. Some things, are needed no matter what the problem domain:

  1. Overview of the problem space
  2. Feasibility and/or Customer studies
  3. Basic IT considerations (domain, email, etc.)

As such the sooner they can be worked on — or have an idea who is working upon them the better. Process can be important — not to be burdened by process, but it can provide a framework or track so that everyone is headed in the right direction.

Lesson 5: Build out the infrastructure Friday night

Leave as much time as possible for front-end details. Given the short time to pitch, having a “wow” helps translate to a “win”.

Lesson 6: It can be helpful to have a place to work together offsite

Since the venue closes each night, it can be helpful, but also a potential snare, to have a place in which to continue working. The snare lies in staying up too late!

Lesson 7: Have an afterparty/post mortem/closure

Startup weekend is zoom-zoom-zoom high energy build gestalt then stop. The let-down afterward can be really hard. Having space and time afterward provides closure which is really, really important. It doesn’t mean that the project is over, but it’s a time to come together and release some of the energy which has been building all weekend long.

The release can be seen in a lot of rituals, whether a benediction or releasing the quarters. Congregants come together for a purpose, fulfill the purpose and then have a closure. It’s something I think is needed.

Lesson 8: Thank the Organizers, Mentors, and Judges

Important but easy to forget. They have put a tremendous amount of effort into creating a space in which creative magic can happen.

Lesson 9: Think like a Boy Scout

Be Prepared — Boy Scout Motto

At any conference or event such as Startup Weekend there will always be a need for extra outlets, connectors, etc. Simply having a small power strip is a great way to make friends and meet new people. Bring one; you’ll be glad you did.

On the more expensive end of things, a micro-projector or access to a large monitor is useful to have people looking at the same thing without needing to huddle around a laptop. Also, it’s good for practicing presentations.

Lesson 10: Be Excellent to Each Other

A lot of what I’ve learned this last weekend has to do with people and small group dynamics. I was fortunate to be a part of a great group of people.

I discovered, too, that over the years I’ve picked up a lot more than I realized about groups, process, and business. I don’t know much about marketing or making a business plan, but I realize that I have learned a lot about people and how they work. I find that I have a better handle on project management than I might have thought, too.

In the course of Startup Weekend, there will likely be some conflict. A certain level of conflict can be good — if nothing else a better product can emerge through synthesis and refinement. However, it’s still imperative to be committed to each other and to the team.

Many cultures have a version of “Do unto others as you would have them do unto you” — in some ways I think that one of the most profound ways of expressing it is espoused by the most excellent Bill & Ted. On the surface they might appear foolish, but:

The Fool is the spirit in search of experience. He represents the mystical cleverness bereft of reason within us, the childlike ability to tune into the inner workings of the world. The sun shining behind him represents the divine nature of the Fool’s wisdom and exuberance, holy madness or ‘crazy wisdom’. On his back are all the possessions he might need. In his hand there is a flower, showing his appreciation of beauty. He is frequently accompanied by a dog, sometimes seen as his animal desires, sometimes as the call of the “real world”, nipping at his heels and distracting him. He is seemingly oblivious that he is walking toward a precipice, apparently about to step off. — The Fool

Lesson 11: Be Pragmatic

The perfect is the enemy of the good. — Voltaire

It is important during Startup Weekend to dream high. However, there are only 54 hours. There is only so much that a group of humans can achieve in that time. So it’s important to both strive for the best yet accept limitations.

Lesson 12: Have fun

It’s a lot of work. A lot of stress. But in order to be successful, it needs also be a lot of fun. If it’s not fun, you’re doing it wrong.


Thank you to everyone who made Startup Weekend possible. I’d like to thank the sponsors, organizers, mentors, judges, and other teams. But most of all I’d like to thank my teammates. You are all excellent!

Leave a Reply

%d bloggers like this: