Why I quit on my team during Startup Weekend

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.

Pitch time

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.

The Voting

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.


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13 Responses to Why I quit on my team during Startup Weekend

  1. (Disclaimer – I scanned the post.)

    So, are you going to continue to work on your idea?

    Also, really hope you participate the next Startup Weekend.

    • Derek Homann says:

      @Danny- Yeah, I think my idea has legs so I am going to continue to explore some options I have there. As far as attending the next Startup Weekend, I most likely will. I think my experience isn’t common although I am sure it does happen to some people. Just because it happened once doesn’t mean it will happen again. I am kind of thinking of it as a failed entrepreneurial venture. The good news is that it was just a Startup Weekend project and failing here is better than feeling in a real world venture. So I take it as a learning experience and I know what I need to do better next time.

  2. Wow. First of all, excellent post and thanks for writing it.

    I really, really wish I had found out about the troubles the team had before you left (I think I heard about it on Sunday morning) because I would’ve immediately told you to SWITCH TEAMS instead of going home. It wasn’t too late to do so.

    I’m sorry your idea wasn’t chosen and I can’t say for sure if trying to recruit people to work on it anyway would’ve been good for your idea in particular or not, but four teams were composed of ideas that weren’t in the top 14.

    If it makes you feel any better, when I participated in Startup Weekend Kansas City a couple years ago, I wasn’t excited about any of the chosen ideas (except one, but I didn’t want to be the 15th member of the team) so I was the very last person to pick my team. I was going around teams for at least two hours, trying to decide. My team was made up of rock stars (one of them is now a well-funded founder who has been published in TechCrunch and accepted to Y Combinator), but I felt bad and insecure because I was definitely the worst player in the band, mostly because I was surrounded by confident, decisive Rails developers with dominant personalities and my Rails skills were rusty and out of date. Having said that, I did learn a lot, I got a lot of encouragement from my team members, and had a good experience.

    You are absolutely 100% correct that the most important thing about a startup is the team; far more important than the idea, execution, technology, viability, etc. because with the right team, the right kind of passion can be evoked, the right kind of feedback can be acquired, and the right kind of pivots can be made.

  3. Scott Blaine says:

    Great post. I hope you give Startup Weekend another go. If you can find the right team it can be a lot of fun, you’ll learn a bunch, and possibly end up with a viable startup at the end. Well worth a weekend of time.

  4. Thanks for sharing!
    Did you like any other teams after hearing their final pitches?
    If you’re one of the judges, who would you pick as the winner based on idea + execution?

    Glad to hear that you’ll give it another try 🙂
    I think Startup Weekend Kansas City is coming up and hopefully Des Moines next?

  5. Derek Homann says:

    @Corey- Thanks for the follow up. Not sure if I would have joined another team mid-weekend anyway. I may have just run into similar problems where I didn’t particularly care about the project. With that said, you guys did a great job putting on the event. The blame for this specific situation is 100% mine. Good news is, it was a great learning experience.

    @Scott- Thanks for the comment. Like I said in the post. I am still a big believer in Startup Weekend even though this last weekend didn’t work out quite how I would have hoped.

    @Robert-I did think some of the teams did a good job during their final pitches and actually showed good execution. The winning team, My Happy Plate, would have been my winner as well. It was a concept that addressed the problem and they actually executed. It’s not a problem that I particularly care about or I think can make much money as a business, but the idea was solid and they executed well. As far as the others go, it was kind of a toss up. The judges didn’t ask many questions so it was hard to get into the nitty gritty details of each company which is what I think separates good from mediocre. With that said, I liked the little bit I saw of Craniak (interactive education courses that uses game mechanics). It was a good idea, but again, it was hard to tell how well they executed because the judges didn’t dig very deep.

    Also, SWKC and DSM are possibilities, but I’m not sure yet. SWOmaha in 2012 is almost definitely a go for me though.

  6. Nice post Derek. Your post will help people understand Startup Weekend more and what they should expect. I’m sure your experience isn’t unique, and I feel that having experiences like that is just a consequence of the format of SW, even though I do believe it brings more positivity than negativity.

    A few points from me though:

    – Don’t feel bad AT ALL about your idea not getting picked. The main reason I say that is because each time I’ve gone to SW, I’ve noticed that with so many people pitching in a row, it never fails that several pitches don’t really get heard. It’s easy to think that each pitch gets the same amount of attention from the audience, but with *so many* pitches in a row, the audience’s attention inevitably lulls. In fact, I honestly didn’t hear the majority of the pitches from this past weekend, which is why I didn’t vote for any – I didn’t feel like I could give an honest vote. Pitching is also really hard when you only have an idea and the majority of the people in the room are buzzing with their own ideas.

    – I definitely think you should do a startup weekend again, and maybe next time if you know you want to do your idea, then do it no matter what. Even if you don’t convince anyone to work with you on your idea, I think being around that energy and talking with people is motivating to work on anything.

    – It’s awesome to see you reflect on your experience so you can learn. Everyone fails, everyone sucks, but the successful ones learn from it, move on, and grow to success. Your blog reminds everyone of that (I know I am reminded of it), so it’s great for you to post this.

    Awesome post! Keep it up!

    • Derek Homann says:

      Thanks Miles. I definitely think we are on the same page. I especially agree about the lull during the pitches. It’s hard to pay attention when there are that many. I was taking notes during the whole thing and I even found my mind wondering. Thanks again for the comment. BTW, I meant to tell you that your final product was pretty cool. Even though it was a bit of a long shot to be a sustainable business, I realize that wasn’t what you guys were going for. From the outside, it sounds like you guys had a ton of fun working on it and while I complained a bit in the post about lack of business focus by a lot teams, I can’t knock anybody who spent the weekend advancing their technical skill set while having fun at the same time. Nice work.

  7. Dwayne Chun says:

    I will add one good reason to go to startup weekend (and maybe a pre-event or two) is to network and make friends with other people outside your skill set, who you can either work with this time (or next time). They’re more likely to remember your pitch, or give you a helping hand next time. It does seem like a lot of teams had two or three people who knew each other already on a team and had a good base to work on.

    As a techie, who knows almost nothing about business…. (I fully admit I just like to code and go to SW weekends for the technical challenges) I wish there was a judge that was just a little bit technically savvy as I thought a few ideas were going to be technically challenging to fully implement unless they somehow got a lot of seed money to help with up front costs. But yeah, we like to work on cool stuff. A product that just needs a website with mostly static content isn’t going to interest more experienced developers, unless it’s in an area they feel passionate about. We want to do something different from our day jobs…At least for me, none of the pitches that won really “spoke” to me either. (Ok, Craniak might have been fun, but it looked like they had a big team already and I thought they might have a PHP dominant tech stack) So in light of that, I chose the most fun project to work on. Video games! I never thought of how it might be if I were a business/enterpreneurial guy who wasn’t really interested in any of the pitches.

    Sorry your experience was bad. I wish we knew you quit. Clearly Slouch Couch could have used at least one business person to help us pretend we had a business strategy. 🙂

    Hopefully you keep working on your idea, what better way to prove everyone else wrong than to start your business, make money and then come back as a Startup Weekend Keynote Speaker/Judge?

  8. Great post, so honest. FWIW, I thought your pitched idea was a great one. However, I didn’t vote for it because I couldn’t fathom where you were going to source your data, something I felt you should have addressed in your pitch. Of course, I blindly joined team Happy Plate because I was excited about the idea from a data perspective and spent the weekend scraping data together from various resources we found in our research that weekend. I commend you for being so prepared for Startup Weekend, frankly, so many were just not, and it showed on Friday night. Of course that commitment to your own idea may have led to some of your eventual feelings of let down. /shrug. I had an idea to pitch myself, but because I hadn’t thought it through enough and had no clear path for what could be done in a weekend, I decided rather last minute not to get up and pitch it.

  9. Derek Homann says:

    @Dwayne- Thanks for the comments. It was good meeting you at the pre-event meetup and seeing you again at the weekend. I can’t argue with your reasoning for wanting to go for the technical challenges. There aren’t many other events that allow you to work on new/hard problems while learning from others at the same time. Also, thanks for the encouragement.

    @Spin Shady- I really appreciate the feedback on the pitch. Addressing how we would mine the data was probably something I should have figured out how to work into the 1 minute pitch. As a matter of fact, I am going to start looking into that right now (shhh, don’t tell my boss I am not working!). As I mentioned in my follow up comments to Robert earlier in this thread, your team did a great job of actually executing on the initial idea. Good work.

  10. I had an idea for an app that relates to non-profits and political campaigns. It’s simple and basically a GUI on top of the Twilio API. I’ve shared this with you, and I’ve talked to folks who are ready to pay for it right now. While at startup weekend, I also talked with someone who was ready to pay for some code I had laying around once I converted it from a simple script I use to a website they could use. The point is that there are a TON of non-sexy businesses out there that people at Startup Weekend don’t really want to get behind. What I took away from that is that you need to build your team before the weekend starts if you want to run with one of these ideas. I plan on building out both these ideas as side projects and see if I can grow it beyond the first few users.

    You shouldn’t of gone home though. I touched at least five of the groups and I’d say at least 3 in a meaningful way. Also, like you, I felt a loyalty to my group and didn’t want to switch groups, but I also felt I could have a bigger impact if I worked with more than one group.

    I think one thing that may have occurred is I went into it with the attitude that I’m going to make the best of it. You went there with the attitude that you were going to pitch and lead a group. It’s sort of like going to an event thinking you’re going to get front row seats and ending up 3 rows from the front. It sucks compared to what you thought you were going to get, but you’re still in a way better position than 90% of people there.

  11. Paul Solt says:

    I had a very similar Startup Weekend experience. In my first one, my team (my pitch) won 3rd place. In my second one, my idea wasn’t picked.

    For my 2nd weekend, I practiced my pitch and prepared beforehand. But it was such a disappointment when the idea wasn’t chosen. I decided to work on it by myself and push through the weekend.

    I don’t know if I’d go back for another weekend. It feels like more of a distraction from what I want to do and not worth the effort. I make iPhone/iPad/Mac apps that I’m passionate about. If I don’t have passion, it’s really hard to work on someone else’s idea.

    If I go back, I won’t pitch an idea I’m attached to. I’m glad my idea wasn’t chosen, because it simplified all worries with IP ownership.

    My other issue with Startup Weekend is that so many of the winning teams go nowhere afterwards. You don’t have to have a good business to win it. It just needs to sound good enough to the judges.

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