Startup Weekend: What Went Wrong
by Alex Teich
I began Startup Weekend with the predictable belief that I would help a team launch a
startup. Yet of the twelve teams that formed on Friday night, ours was the only one that
didn’t make it to any credible stage. At about 9:30 PM Saturday, our team officially
folded. Some went home and returned later to see the pitches. I was able to find another
team that needed a designer and finish out the weekend with an occupation.
Other teams who’d been in our proximity came by to pay their respects to the deceased
startup, and some people seemed to really feel bad for us. I felt a little bad too, at first,
thinking that it reflected somewhat poorly on me, but one of the event volunteers assured
me that it was not so unusual for a team to never get off the ground in the 54 hours. The
important thing, of course, was the experience, and what we could all learn from it.
I felt that it was therefore essential to type out just what that was- to draft a post-mortem
while the trail of events that led to defeat was still fresh. If failure is not so uncommon,
then perhaps neither are the circumstances and choices that, in our case, didn’t make a
seemingly great idea work.
As I thought back over the weekend, my foremost realization was that the “No Talk, All
Action” slogan hadn’t applied to our team at all. We had talked ourselves to the moon
and back, and had failed, in so many ways, to simply act. What had we talked about? In
the thick of it, none of it had seemed like a waste of time, yet we had nothing to show for
it in the end.
On Sunday, I talked with some of my former team members, and all of them agreed
wholesale with at least two things:
1. We agreed that no one person in the group was culpable for any misstep- we all
contributed to the same group behavior and failed at this equally.
2. We each experienced a kind of shock when considering our failure in retrospect. We
were all intelligent and creative people, so it was difficult to understand why we hadn’t
simply done what we’d needed to do.
Here, now, are the five biggest pieces of advice that I’ll be sure to send through a
wormhole to myself back on Friday evening, or maybe just remember for the next Startup
Write it down (Analog is actually better!)
Of course, we realized that writing things down (to-do lists, features of the website,
navigation trees, pieces of the business model, etc.) would be an important practice. We
figured we could use Google docs for this, so that we could simultaneously view and
edit everything right from our seats. I realize now that something that goes on a wall-
a whiteboard, chart paper, sticky notes- is a far better idea. The Google docs actually
discouraged us from writing anything down, because once an idea had been spoken, no
one had time to open the correct document and place it there before it was gone with the
wind- and even though we all had access to them, we weren’t necessarily all viewing any
particular document at the same time. We never planned effectively, and this was a major
Pivot points are everywhere
As soon as the team sat down for the first time, we started running with our concept in a
freewheeling plenary conversation. The possibilities of what the product could be took
us in several directions. What if we tried it this way, that way? (No one wrote down the
ideas.) We didn’t keep this up for long, though- it was decided that we didn’t want to
stray from our original track right out of the gate. That was a sensible enough decision.
What wasn’t sensible was that after spinning out all those alternate realities, we didn’t
hang on to any of them as possible future pivots. It could happen at any moment in the
process- someone on your team might think of a different version of your product. Even
if you’re not thinking of pivoting and you don’t have time for those tangents, you may
very well need them later.
Tackle the assumptions
As I’ve said, we spent a great deal of time fleshing out our idea with a lot of talk. It
seemed to us that we were getting somewhere, because everything we were talking about-
profit margins, design, etc.- was perfectly relevant.
What we didn’t realize- in spite of several mentors who made admirable attempts to
explain it to us- was that none of our conversation was in fact relevant, because it relied
on assumptions that we hadn’t yet investigated.
The main assumption we failed to address, the one perhaps most axiomatic to the
existence of our product, is whether demand even exists in the first place. This, of
course, is what the first round of surveys is aimed at- asking potential customers if they
experience the problems that the product is intended to solve. Our product was a platform
for educational games, and we decided that our customers were clearly the parents- they
were the ones who would be paying. We surveyed parents, but incredibly, we didn’t
survey young people to see if they would actually want to play educational games. We
just assumed that they would.
Our assumptions might have been our biggest problem. By getting out and talking to
more people, we might have learned things that would have guided our process. Instead,
we spent our time guessing. We didn’t think we were guessing. We thought we’d talked
to plenty of people. We just didn’t recognize our assumptions for what they were.
A good exercise on Friday would have been to brainstorm the essential questions about
our product- the ones that investors would eventually ask- and from there, play devil’s
advocate to draw out the assumptions. Just what were we taking for granted? (A mentor
could help with that.) The goal would be to start the surveys as early as possible, and to
make sure that the surveys cut directly to the most fundamental assumptions about the
viability of the product.
Everyone’s a leader
At many points, one of us would sense time slipping away and would say something
like, “Okay guys, it’s time to really decide on ______,” or “We need to plan out
________,” or other words along those lines, in an attempt to step into the role of leader.
What then followed was typically a circular conversation that decided nothing.
What I see now is that no one in the group truly had the kind of authority that a leader
has; whereas a CEO or a boss hands down directives to employees, all of us on the
team were co-founders, and therefore equally responsible to act as leaders. Thus, while
coordination within the team is necessary, the individual members need to simply take
initiative. That doesn’t mean remind the group that it’s time to act. It means act. If no
one is helping you plan out the day, plan it out yourself, and show people your plan. If no
one is keeping track of the time, or writing a survey, or going to Discovery Green to ask
people questions, just do it yourself. Don’t put it to the group to make decisions together
if the group is having trouble doing that.
Don’t stop believing
On Saturday night, we decided that we were exactly one day behind. That wasn’t
necessarily the case, but the thought took the wind out of our sails. We’d considered
many different angles on what our service could do, and for whom, and had decided
(through assumptions, perhaps) that there was no way to make a profit. We lost faith
that the point we’d started at could lead anywhere. We kept working, but without the
enthusiasm and anticipation. We just weren’t working seriously anymore. Once we
admitted to that, resignation soon followed.
Yet there was actually no good reason to quit- not even the looming deadline or the
seeming intractability of our problem. Another group- the one I joined next, in fact- was
also still struggling with its concept on Saturday night, and actually made a major pivot
as late as lunchtime on Sunday. They went on to present, and even though their model
was incomplete, we could all see the potential of their idea and the momentum they still
So our team never really came together, but never mind- I can easily say that last
weekend was one of the most challenging and fun educational experiences I’ve had in
years. Next time, I’m crushing it.