Blake Perdue - Website & app reviews, and technology & startup commentary

Startup Weekend: Lessons Learned

November 10th, 2008 in Startups

Although I helped with logistics and setup, I was also involved in one of the two teams that imploded at Atlanta Startup Weekend 2: Seed Stage Records. We were all disappointed to see a Startup Weekend team fail, but there’s still value to be found in the rubble. As the Seed Stage Records team disbanded Sunday afternoon, each team member noted that the lessons they learned from this failure were well worth the price of admission and the time invested.

Team

Most people agree the most important ingredient in a startup is the team. I witnessed first-hand how important the team is. The Seed Stage Records (SSR) team was a diverse and talented group that generated a lot of great ideas for what SSR could become. But what ultimately killed SSR was the team’s lack of experience and leadership.

The founder, whom I really like and have a lot of respect for, didn’t have the leadership skills to step up and take control of the group, make tough strategic decisions, and drive the team to set and reach milestones. There were a few people with “strong personalities” that continually derailed the group and questioned its direction. The result was that the group spent most of the time endlessly debating features, pricing, and strategy.

While SSR was struggling to make decisions, I was checking in on other groups and lending my skills where needed. The groups that were making the most progress were composed of serial entrepreneurs, seasoned business execs, and developers that could deliver. The SSR team was talented but there was no one on the team that had experience building the platform and features SSR wanted to deliver. Instead of hustling to build an alpha version, the SSR team spent alot of time trying to figure if and how the product could be built.

Lessons Learned: Pick a startup based on the team not on the idea. Make sure the team has a good dynamic. Make sure the team is composed of people who can actually build the product.

Strategy

By late Saturday night it was apparent that SSR was struggling and desperately needed help. Lance Weatherby was nice enough to drop by shortly after midnight to hold an inspirational strategy session. After observing the group debate strategy, Lance stepped in and asked everyone to take out a sheet of paper and finish this sentence: “Seed Stage records is ____________.”

(Here’s a good template for doing this exercise.)

Lance then wrote down the answers on the whiteboard, which revealed that the team had very different ideas on what SSR should be. Lance led a few more exercises to help the team make a decision on what exactly SSR should do, what it would take to do it, and who would be responsible for the various parts.

Lance’s last minute intervention (thanks Lance!) made it apparent that the team had never agreed on strategy and value proposition. This caused much confusion and led to the stalemate debates that were preventing progress.

Lessons Learned: Decide on strategy and value proposition early on and make sure everyone is aware of and understands it.

Leadership

Lance’s intervention, which several SSR members noted was the highlight of their weekend, illustrated that SSR had a real lack of leadership. SSR needed someone to stand up, lead and make tough decisions that might upset some of the team.

As I tweeted Saturday afternoon, there’s a reason startups have CEOs: someone needs to have the authority to make difficult decisions. SSR was run more as a democracy where everyone had an equal voice. This is no way to run a startup and was the root of many problems.

In addition to needing a CEO who would make decisions, SSR needed other clearly defined roles. SSR needed a product manager, a project manager, a marketer, etc. Instead of assigning roles, team members jumped from task to taskĀ  which resulted in duplicate and unfinished work.

Lessons Learned: Leadership and roles are critical. Having a CEO who makes tough decisions and people with specific roles is a must.

Large crowd eagerly awaits the pitches at the end of the weekend.

While I am disappointed that SSR failed (some group members might move forward on the project), I am grateful for having had the opportunity to work with them, witness the problems and learn from the mistakes.

What are your thoughts about these lessons? What would you add?

Comments

Great lessons learned. Thanks for sharing!

Jennifer Bonnett on November 10th, 2008

Blake,

I totally agree with the assessment of the team as well as the takeaway from the weekend. The concept needed a strong leader to make the hard decisions. There was a lot of discussion about what SSR could be, but no one made the hard decisions. In retrospect, I would have probably chosen GivingTi.me or Jumbis as they seemed to have two of the best leaders of the group (especially Sanjay) and I could have utilized my development experience more and learned from his leadership.

If I were to boil everything from this weekend down to a single idea, it would be, “Work with people who are smarter and more experienced than you.” We can all learn by failing, but you don’t have that luxury in Startup Weekend. Honestly, can anyone say they have the have the time in their everyday lives to do so?

I really enjoyed working with you and hearing your ideas for the project. I knew on Friday you were one of the more experienced because your push for a timeline and building a foundation we could all build on. Hopefully, our paths will cross again under more fruitful projects!

Randall Prince on November 10th, 2008

Great feedback. I’d add another point: the team members also seemed to have different expectations of the weekend, and if we had defined the roles, value proposition and expectations up front, as you pointed out, we would have made the decision to fish or cut bait Friday evening.

I really appreciated your insight this weekend, and your comments were right on target.

Jeremy on November 10th, 2008

I really think you did a great job capturing what happened to the SSR team this weekend. It definitely was a business failure but I think everyone involved learned a lot from the process. Im definitely ready for another shot at it next year (or maybe even sooner). Thanks for all of your discernment and help along the way.

Andy Macdonald on November 10th, 2008

I think you’re right about trying to run it as a democracy. Startups don’t work that way. I think we could have had someone in charge and it would have helped a lot.

Either way… it was a fun experience that I would do again. (Maybe with better results next time.)

Michael on November 10th, 2008

That logo is outstanding.

Adam on November 10th, 2008

Great feedback Blake. I hope our paths will cross again in the future. I have posted my thoughts at http://lin.cr/8hf

Shaun on November 10th, 2008

Interesting. Some of the challenges sound familiar, right?

Ben L on November 11th, 2008

Thanks for the great analysis Blake! I agree completely and I’ve learned even more from your post. Sorry I couldn’t help out that much. I just wish I had more experience on both the technical and business side.

Dan on November 11th, 2008

Excellent observations blake. Some of my own…

I agree with you that a business needs a leader, someone to make the tough calls, to do what’s best for the team regardless of any individual’s feelings. BUT, what do we do with people that have great ideas, yet don’t have the wisdom or experience to deal with personnel conflicts? Does everyone with a great idea have the traits of a great leader? Do great ideas only come from great leaders?

Perhaps the answer is that, at least in SW, the person who pitches and whose idea is accepted, abdicates the role of CEO to someone on the team who can carry out his vision. Of course, that’s always an option, but maybe doesn’t seem obvious to many people. That might have been a solution in SSR.

I think Lance did an excellent job of redirecting the team to find its purpose. I also thought that Saturday night they had all agreed on a direction that was to be carried out Sun morning. I don’t know exactly what happened Sun morning, but it was disappointing to see them agree on Sat nite to pursue a direction, to have it once again, cussed and discussed, and never move forward on Sun morning.

There were some very passionate, bright people on that team. I think they formed as a team in the beginning and could have delivered. But they may have failed to understand that when you are on a team, you do what is best for the team, regardless of what you personally want to do.

George on November 11th, 2008

Hi Blake,

Thanks for sharing your thoughts. Definitely a great postmortem on the entire project and weekend. Its always better to take away the positive aspects of something like this.

Eric on November 11th, 2008

Hi Blake,

You are helping others become successful by learning from what you went through. Thanks for sharing this experience with the rest of us.

Paul Tran
BrightIdea.com

Paul Tran on November 11th, 2008

@george I think you have a very good point. I think most of the groups expected the founder (person with the idea) to be the leaders. But, this shouldn’t always be the case. In SSR case, myself or Randall should have stepped up and taken on the role of CEO, or at least brought the matter to everyone’s attention. Lesson learned :-)

Blake Perdue on November 11th, 2008

Blake, you’ve succinctly described something I witnessed at Nashville Startup Weekend as well. It was interesting hearing a couple of teams say how great it was that they ran democratically, but I felt they would have accomplished more with someone specifically at the helm. Just because someone leads the team doesn’t make it that individual’s project, nor does it diminish the rest of the team members’ contributions.

Andrew Duthie on November 12th, 2008

Blake:

Great post. Often you learn a lot more by failing that you do by succeeding as you demonstrated your learnings here.

Wish I could have been there to share the learning. Next time…

-Mike

Mike Schinkel on November 12th, 2008

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