This past weekend was the first Startup Weekend that I ever attended and I was extremely excited about it. Unfortunately, it didn’t end up as magical as I thought. But in a weird way, it ended up being an extremely good learning experience.
So here is how everything went down. I apologize in advance for the length of this post. Feel free to turn back now.
Pre event preparation
Prior to coming to Startup Weekend Omaha, I had an idea I had been tossing around for quite awhile. It was a mobile couponing app that I thought was a great idea (I actually still think it’s a great idea). It was an idea that I was passionate about partially because of my personal love for personal finance. But ideas don’t mean shit unless you execute on it and I realize that. I was bringing this idea to Startup Weekend because I was hoping that I would pitch the idea and would get a team to work on it with me and help bring this thing to life. I had actually done a pretty decent amount of prep work in regards to idea so I knew most of the areas we needed to work on during the weekend from both a tech and non-tech side of things. I also watched a lot of pitches from other Startup Weekends and practiced my one minute pitch quite a bit in the week leading up to the weekend, so I was feeling pretty good about my idea and pitch by the time the event started.
The Omaha Startup Weekend had just under 110 attendees. Just before the pitches started, the organizers told us that 12-15 (I don’t remember the exact number they told us) of the top ideas would be picked to work on based on votes from the attendees. Of the ~110 attendees, roughly 50 people pitched an idea.
Since there were so many people pitching, I came up with a small plan to try to give my idea the best shot of being chosen. I waited until the majority of people pitched and then I jumped up to do my pitch near the very end. My thought was that this would mean my idea would be fresher in the minds of people by the time it got to voting time. Also, as I was sitting in my chair, I didn’t personally hear many ideas that I thought were very good. Some of them were definitely interesting, but were definitely not viable businesses. A bigger percentage of them were neither interesting nor viable businesses, so I figured it would be really easy to beat those guys.
When it got time for me to pitch, I went up there and tried to show some enthusiasm, explain how my idea solves a problem that a huge number of people have, and what kind of team I needed to help solve this problem. I think my pitch ended up going pretty well although I would have to see a video of my pitch to actually know for sure. That one minute goes by really freakin quick.
Needless to say, after the pitches were done, I was feeling pretty good about my chances.
So the pitches were done and everyone was supposed to vote on the ideas they liked the best. We were all given three votes and could put them on any of the ~50 pitches that we wanted. You could put them all on one idea, or you could split them up between multiple ideas if you wanted. We were sitting in the auditorium at UNO and were dismissed by row in order to go cast our vote. When it was time for my row to go vote, I went up to the idea list to see how my idea was doing. I couldn’t tell exactly how many votes I had, but it looked like I was doing pretty well. So I went ahead and voted for 3 different ideas that I thought were kind of interesting instead of voting for my own. I didn’t want to be the douche that voted for his own idea. I would rather have my idea win on it’s own than need my votes to win. So after that, we went out to the hall to mingle with other Startup Weekend participants while the organizers counted the votes.
While we were in the hall, I had a couple of people seek me out to say they liked my idea. I chatted with them about some ideas I had for making it an actual business rather than just a cool app. I also chatted about some of the other ideas I thought were interesting as well. Needless to say, I was still feeling pretty confident that my idea would be chosen at this point.
Ideas are chosen
After the judges counted up all the votes, we were shuffled back into the auditorium. The organizers were putting the names of the top vote getters up on the projector as we all sat there. I saw the first couple names go up and my idea wasn’t on there. I wasn’t super worried because so many ideas were going to get chosen. After a couple of minutes, all of the pitch winners were on the projector. Unfortunately, my pitch wasn’t on there (for the record, I missed by 2 votes). My heart literally sank. I tried to pretend it didn’t bother me very much when I was talking to the two guys on either side of me, but the truth is, I was super bummed. I had been thinking through my idea for so long before the weekend even started and had put in a decent amount of pre-work on it as well, so I couldn’t help but be bummed. I also truly believe that my idea, if executed properly, could help people. At the same time, I thought it could actually be a viable business which I was fairly certain that many of the other ideas could not.
I realized a couple of things after that:
1. Either my idea was not as good as I thought OR my pitch was not as good as I thought…or both
2. Most of the audience were technical people (developers or designers). One thing I have learned from tech people, is that they like working on fun projects. I felt my idea was extremely practical, but it was by no means sexy and that didn’t cater to the audience I was pitching to.
3. I was disappointed by quite a few of the ideas that the audience chose. If you want to start a viable business, it needs to be able to make revenue and sustain that revenue. A lot of the ideas that were chosen, we definitely interesting, but from a business perspective, we extreme long shots to make any money. Now I realize that there is no problem with people just wanting to work on interesting projects, but if more people in Omaha don’t start realizing that you need to make a viable business out of stuff like this, it will not progress the entrepreneurial ecosystem in the area because no one will actually succeed in making these ventures a successful business.
Moving on and choosing a team
After the final ideas were chosen, I chose not to try to recruit a team to work on my app as I realized that would be an extremely uphill recruiting battle at that point. So instead, I decided to join another team that had be chosen from the pitches. I won’t mention what team I joined, but you can probably find out pretty easily with a little investigation.
Unfortunately, I wasn’t in love with any of the other ideas that were pitched. So I just tried to join one that I thought was interesting and see where it went. The team I ended up joining had two people when I stopped by. They both had a little bit of technical skills, but it seemed like it would be difficult to a working prototype with what the three of us could bring to the table. So we all realized we needed some more help. The two guys who were already on the team, went to see if they could recruit some technical talent and I hung out by our assigned work room to see if anyone else would show up. We ended up getting lucky that one technical resource did end up stopping by and joining our team (we had one other non tech guy join as well). So our team was set with 5 people. One developer, and 4 other guys with minimal tech skills who would try to put everything else together.
When the team was assembled, we went into our room and spent the next 60-90 minutes discussing how we thought this whole thing should work. We came up with a basic structure for the website and how we felt the business should work. A couple of us had some basic tasks we needed to complete before we were to meet again on Saturday morning at 7am.
Things start going downhill
Our team was supposed to meet at 7am on Saturday. only one of the 5 of us got there at 7 (our developer). Myself and one other guy got there at 7:15. Another showed up at 8:15 and we didn’t see the final member of our team until after the 9am presentation by Sen. Ben Nelson. We also briefly had another technical resource that I found via on Twitter from the night before. He showed up at 7am, but he left us soon after with the promise to come back but he never did. I have a feeling he didn’t like how disorganized we were and I don’t blame him.
After we reconvened following Senator Nelson’s presentation, we started working on some basic stuff like creating Twitter and Facebook accounts for our team, sending our some surveys to help us determine market fit, and getting a logo created for our company. We also decided that our company would best function as a 501c3 non profit as opposed to a normal “for profit” business. Unfortunately, after that, we were all kind of lost on what to do. This wasn’t a sector that any of us had any experience in so we really weren’t what direction to go. The person who pitched the idea (our “CEO”) hadn’t thought through the idea very much so he didn’t really have a vision for how this should work. It was also very apparent that the person who pitched the idea and who was supposed to be the CEO was not taking the leadership role. One of the people in our group was a rather strong personality who had strong opinions about certain things and often came off in a combative manner which I think also caused a bit of a problem when it came to our team dynamic.
So basically we had a couple of problems.
1. Only had one technical resource. God bless that guy. He never complained and was the main reason that anything was presentable at the end.
2. I can’t speak for anyone else, but I personally could have cared less about the type of company we were building. As one of the team members later said, it’s one of those ideas that you think should be built, you just think someone else should build it because you don’t care about it that much. Also, anyone who knows me, knows that money is a motivator for me. It’s definitely not my only motivator (or even biggest motivator), but the lack of financial upside with this company, killed my motivation.
3. We weren’t a good team. The personalities in our group didn’t mesh well. We had a mix of people with extremely strong personalities and extremely passive, non-vocal personalities. Our team also did not have skill sets that complimented each other. One technical guy to four business/do everything else guys. You really don’t need that many “business guys” in a small startup.
I quit on our team
As the day wore on on Saturday, I became more and more disengaged with the project. This was primarily due to items 2 & 3 that I just listed. I simply couldn’t work on a project that I wasn’t passionate about with a team that didn’t work well together. Part way through the day, my friend from work who wasn’t able to make it to Startup Weekend, sent me text to see how it was going. He knew I was super psyched and he wanted to see what he was missing out on. I texted him back that our team didn’t work well together and that I could careless about the project. That’s when it really clicked to me that I wasn’t having fun, I wasn’t learning anything, and I needed to cut my losses.
It took me a couple of hours to actually work up the courage to say how I felt. I was fairly confident that the others on our team felt the same way about our team and it was just a big elephant in the middle of the room that no one was addressing. So around 7:45pm on Saturday, I addressed the team and let them know that I just wasn’t feeling it anymore. I let them know that I thought it was a decent enough idea, it just wasn’t one that I particular cared about. I also said that I felt our direction wasn’t very clear and that I wasn’t going to carry on with the team. I told them I would rather man up and tell them to their faces, rather than just not show up on Sunday morning. I let them all know, that I felt like a huge asshole for quitting, but I felt like it was for the best. Surprisingly, they were all very understanding. My guess is that they were all feeling the same way. Or I was just not very useful and they didn’t care if I stayed anyway. Needless to say, I appreciated them all letting me say my peace and them being very understanding of it. One of the other guys on our team aired some of his grievances as well but he stuck around for a bit, although I don’t believe he came back on Sunday.
As I got in my car and left Mammel Hall, I felt like absolute shit for a bunch of reasons. I didn’t get to work on the idea that I was obsessed with (and honestly thought would be a viable business), I quit on a team that I had committed to, and I didn’t get the overwhelmingly positive Startup Weekend experience that so many other people seemed to have gotten. Honestly, I just felt like curling up into the fetal position and just listening to “Everybody Hurts” by REM. I was that fucking bummed by how it went down. I went home and hung out with my wife and moped around the rest of the night and most of the next day. It sucked.
From what I hear, the team had more issues the next day as well and almost didn’t present at the final pitches, but they pulled stuff together and the 3 remaining members presented at the end of weekend. I watched the presentation live online and they didn’t do too badly. I think the execution of the company was pretty poor, but it worked out OK because the judges didn’t seem to dig in very much into any of the companies that were presented. On a side note, I was a bit disappointed in the judges. They didn’t seem to dig into the companies very much and they almost appeared to judge more on the actual idea that was presented and not the actual execution which is really the most important part.
Immediately after quitting, I felt like there was nothing positive that came out of this weekend. But as I reflected back on it, I think I actually learned a ton from Startup Weekend. I just learned it in an unconventional way. I found out that I need to be passionate about the project I am working on or I won’t give it my full effort. I found out that getting a team that cohesively works together is arguably the most important part of building a company.
Also, I have to say, that my experience with Startup Weekend was unique to me (although I am sure a small numbers of others have similar experiences). From what I can tell, the vast majority of people actually have a great time at the event. It wasn’t what I expected, but I did learn a lot about myself and that wouldn’t have happened without Startup Weekend.
I have to say, that the local team of organizers that put together the event did a fantastic job. The event wasn’t without it’s small hiccups, but overall it went very smoothly and that is because of the team that organized it. They did a great job and should be applauded for their hard work.
Lastly, I can say that I am still a strong believer in Startup Weekend. Even though my experience wasn’t the best, I still think this is a great concept and it is a great event for our community.