Let me begin this post by expressing my gratitude to the Startup Weekend Boston crowd that came out over the weekend. I was impressed by the level of integrity, hard work and dedication of many of the people that turned out to the weekend. What follows is a critique and evaluation of Startup Weekend overall, but I will make reference to the SW Boston because I think it highlighted some of the questions that I believe really do need to be answered.

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I want to first admit that I played a major part in what I think went wrong this weekend. It will become more apparent as you read where I think I failed, but as a leader, I have a lot to learn. I’m constantly working on speaking up about my concerns more quickly, and in a more effective manner. I slept on the floor this weekend, ate poorly and didn’t take care of myself the way I usually do. My fatigue and scattershot approach to leading is nobody’s fault but my own.

Rather than say what Startup Weekend lacks (TechCrunch UK has offered a thorough review of Startup Weekend, to which I responded at length) I’d like to show what I think it needs.

This is a response, in large part, to the article at TC, where they threw down the gauntlet:

“What are we to make of all this? Perhaps I have gone over the top in detailing the Startup Weekend’s activities to date. But with startup events proliferating like wild-fire across the UK, Ireland and Europe, it’s important to keep one’s feet on the ground. Any event needs to be clear about what the participants are getting into before they get into it - especially where equity, shares, intellectual property and new companies are involved. If Startup Weekend can address those, all well and good. But if it can’t, then alarm bells should be ringing.”

Before anyone sounds the alarm, let’s get some things out there.

Locals Must Outnumber Out-of-Towners

When I heard that a lot of kids from Boulder were flying in to Boston to participate in the event, I was thrilled. I hadn’t seen them in several months and I know that they’re a talented, capable group of people. A few people also came in from out of state besides the Boulder crew (some people have posited it was Startup Weekend Boston-Boulder). While I’m happy they came (some of them were positively an integral part of the weekend), I think the fact that some saw the weekend more as a vacation was detrimental to the group. I don’t mind that some saw it as a vacation; I do mind that they appeared to commit and then disappeared less than halfway through the weekend.

I think that a new rule needs to be instated for Startup Weekend. We should cap the number of people coming in from beyond a 100-mile radius at, say, twelve. Beyond that, I think that it gets away from the original concept, as outlined on the SW site: “StartupWeekend is the new way to allow your local entrepreneurial community to come together.” The key word here is local.

In addition to that rule, I don’t think you should be permitted to pitch your idea if you’re an out-of-towner. I pitched this weekend and my idea was chosen. Now, if I want to stay involved with the project, how would I best do that? I tried to listen in at the first SW Houston meeting (a few days after the weekend was over). We used TalkShoe and it sounded like “crrrrrrrrr” on their end of the line. We are not yet technologically advanced enough (although tele-porting would be nice) to get me to Boston for future meetings once a week. Although that sounds pretty wicked…

Create Success Metrics & Refer to Them Often

What makes Startup Weekend (the entity itself) or a weekend successful? Is the fact that we got to launch this weekend enough for people? We can now accept signups but have nothing to follow up with. To me, this is the tech equivalent of a cocktease. I would almost prefer to go back to a splash page and email catch to this.

I don’t think the weekend had a lot of success metrics. We need a Milestone Board that goes up Friday night and people contribute to whenever they want. When a milestone is reached, it should be checked off. That way, even if we don’t make it to launch, we know that we’ve gotten a lot done and it’s not simply an ethereal, wishy-washy, “wow, we did a lot of stuff in 52 hours!”

We never talked about what a successful weekend would look like. If creating community and making new friends is the measuring stick, I think we definitely did that!

Is Startup Weekend (as a business) already successful? And if so, what’s the best way to keep it the way it is now? If it grows, how will we be able to stick to the original founding principles? Especially if it’s being taken by other communities and happening without Andrew being there to help guide them?

Why not kill the company?

At the end of VoSnap I asked several participants what would be wrong with killing the company. Most of us had day jobs or families to get back to. Very few of the participants have continued to meet up with consistency after the weekend ends. What’s the solution? How will we know when we’ve “succeeded” during and/or after the weekend? Let’s include a page in the PB Wikis that are set up for each weekend to keep running tabs on milestones and celebrate each one, however seemingly trivial.

The 5/45/50 Split Question

The company we create during the weekend is split up thusly: 5% goes to Startup Weekend off the top. 50% goes to the people that participate in the weekend. 45% goes to those that continue to grow the project past the weekend. Is 45% enough of an incentive for those left to do the rest of the work (hundreds or thousands more hours of work, even), enough?

We have a Founder’s Bill of Rights, but what if we created a Founder’s Bill of Expectations. That would outline what happened if you only show up to half a day or watch the baseball game. You should be forced to give up your shares if you’re not going to be a team player. It’s a group game, Startup Weekend. If you play the game as a group participant, you should be rewarded.

Designated Roles Kill Creativity

I laughed when I saw video from Startup Weekend Toronto (it’s no longer available because they’ve taken down the site). Participants had either given themselves titles or been given them. We had a spot of that at Boston, too. If you want a title, go work for a corporation. If you’re unwilling to wear multiple hats during the weekend, think twice before signing up.

This brings up another important point. Should you do what you’re talented at or do want you want to do at Startup Weekend? Let’s say your day job is a PR person. You get paid to do it, you love it, but you’re burnt out from doing it all week. So you sign on to be a designer even though you don’t even have Photoshop installed on your computer. What gives? I don’t see Startup Weekend as a time to learn an entirely new role, although learning is a huge part of the weekend. I see it as a chance for you to shine at what you do best.

Paul Salamone, the Lead Designer at Startup Weekend Boulder (and he joined the Houston & Boston SW’s via vid chat from Berlin) has this to say, “it’s not even that people should be doing what they do best, but what they are NEEDED to do. I was needed as a designer at Vosnap because there were none, but it could have been the case (strange as it sounds) that my best use was as garbage boy or something. People should come in hoping to do what they enjoy, expecting to do what they do best, but be satisfied if they are needed for something they don’t want to do at all.”

Titles and designated roles are dangerous and can lead to frustration, especially if your role has you doing something that you enjoy, rather than what you excel at. Working on Biz Dev even though you’re a designer by trade is cool, but don’t expect people to be totally happy with it. Step up to the plate when you can help in a role you’re talented at, even if it’s just in a brainstorming capacity. Your peers (and potential future bosses that may be watching from a distance) will appreciate it.

Cubicle Life Kills Creativity

Before I say too much about the location, I’m really thankful we had a host for the weekend that allowed us to work in their space. Unfortunately, the set-up may not have been entirely conducive to getting a group project done, because there were cubicles and one- to two-person sized offices all over the place. This created problems such as:

1) Miscommunication and lack of communication between groups
2) Shit talking
3) Mini-coups

On that note, a lot of shit-talking has been eliminated in past weekends because we were UStreaming the event. A live feed keeps you honest, however Big Brother it is. If you know what you’re about to say may be on the record for eternity, you might think twice before making a disparaging remark. You learn to keep things positive.

Communication is the most important element to building community during the weekend. I think it’s absolutely vital that future Startup Weekends be held in open spaces that facilitate group discussion throughout the weekend. It’s much easier to take the “pulse” of the group when we’re all present and available. At SW Boston we spent a large part of the weekend running around looking for vital pieces of information and people, rounding up people for meetings and walking in on “private” conversations. Amazing how an open space, even if it’s louder at times, eliminates much of this.

A final note, the location of the event seems to me crucial to its success. This weekend’s location was almost an hour from central Boston (we walked, took the train and then switched to commuter rail or cab to get there). And there weren’t any little cafes or delis nearby for people to get out and get some fresh air. These elements need to be present to keep tempers even and bodies happy.

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Hopefully, this piece can help legitimize and help provide a container for what I believe is an amazing, life-changing and potentially wide-reaching event/movement/lifestyle.

I want to reiterate that I made some long-lasting and important friendships this weekend. I loved being in Boston and I’m thankful we had a group of dedicated entrepreneurs working on a project that can go on to be something bigger than any of us can predict, if we decide to take it that direction. In the meantime, let’s keep working on making Startup Weekend even better from weekend to weekend. Each of our voices count, your feedback is crucial to the success of future weekends, and I sincerely hope this phenomenon continues to grow and exceed the expectations of everyone involved. See you in DC or Chapel Hill or…