Last Friday night was the start of my first Startup Weekend, and I didn’t know quite what to expect. In fact, the logistics of getting me into the city from the suburbs for such long days had me thinking I should just give up my ticket. But I manged to wrangle accommodations down the street from the University of the Arts where the building was held, and arrived just in time to join those gathering for pre-event drinks and snacks.

I grabbed my badge from the table and started talking to people. If you know me at all, you’re already thinking I’m making stuff up – I am not usually so social. But Startup Weekend, unlike most other events, is not an event that you attend passively. You interact with other people or you don’t experience it. Within the first 20 minutes of the event, I met and had great conversations with two people who went on to form teams that won second and third place!

The weekend starts out with everyone in an auditorium to learn about the event. They talk about the prizes (of which there are basically none but accolades and a presentation slot at Switch Philly for the top team – haha, more work!) and the schedule and cover a few of the basic things that everyone new - like me - must be wondering. While waiting in the auditorium, I met a few new folks, specifically seeking out people with a “Designer” name badge.

When you register for the event, you can choose one of three identities: Developer, Designer, or Non-Technical. Having met some of the “non-technical” folks, I wouldn’t call them that. My impression was that although there was a fair percentage of non-technical attendees, developers were far and away the most abundant, with designers trailing a far distant last place. I don’t understand why this is. Maybe it’s the marketing and how it tends more toward developers and entrepreneur-types from local business schools, but the University of the Arts is right there… Am I to believe that user experience design is not as commonly taught a discipline? (Hey, artists! Wanna make money doing art?… Get into UX!)

After the introduction, we were ushered to the atrium, a larger room that would become our workplace for the next two days. In the atrium, we gathered at tables based on random numbers stuck to our name badges. We were given some direction about making pitches, which are an essential part of Startup Weekend. At the table, we found written two unrelated words, and as a group each table needed to come up with a product and a pitch for that product.

The words at my table were “Nickelback” and “Whistle”. Our pitch was for a product called “Whistleback” (obviously). The pitch went something like, “Hi, I’m Owen and I want to talk to you about Whistleback. People who really know their music are tired of unchallenging ‘Name-That-Tune’ games where the music is too easy to guess. That why we’ve built Whistleback. Whistleback picks a Nickleback song at random and whistles it to you, after which you must identify the song to earn points. The game is hard because all of Nickelback’s songs sound so similar! Try it out - Whistleback!”

Pitches have vital components. The name of the product, the problem it solves, and how it solves it are all vital. The presentation style is important, too, naming the product at the beginning and end so that it sticks in the head of the audience. Being charismatic helps a lot. I felt bad for many of the people pitching later on who seemed to have very interesting ideas, but had difficulty articulating them, whether due to not following the structure or problems speaking English well. But all of the tables did a pretty good job of pitching in this round.

Our table didn’t win this round of pitches as decided by the organizers. Another table, presenting “Guerilla Ice Cream”, a product for moms to disincentivize their kids to treats, won the honor of presenting their real pitches first.

And so the pitches began. 43 in all. There were some good ones, some not so good ones. Even I pitched a website that would mine your Facebook account for music preferences and then sell you tickets to bands you like so that you don’t ever miss a concert for your favorite bands. My pitch read like this: “My friend called me last night and said, ‘Hey Owen, where were you at the concert last night? It was awesome!’ Man, I am so tired of missing concerts of my favorite bands. That’s why I want to build StageDrive. StageDrive is a website that mines your Facebook profile for information about bands that you and your friends like, then tracks when tickets for those bands go on sale so that you don’t ever miss a concert. I’m looking for developers and designers to implement the site, and business-savvy people who can help turn my idea profitable. I’m Owen and my idea is StageDrive.”

Each pitch name was written in marker across the top of a giant 3M stickynote and placed on the wall. We wrote a summary of the idea underneath and some more information about what we would need for implementation. Then, we went around the room and interviewed people whose ideas we liked best to learn more about their needs and plans. If we ultimately liked their idea, we could apply one of our three stickers to their poster to vote for their project.

I looked for a few projects that I thought were worth considering. There was one, Family Time, that was a social network for families that feel they don’t spend enough time together. Another was a system for local bands to gain followings and exposure like for bigger bands. There were so many interesting projects. One was by a woman named Anittah who wanted to build a system to help educate teenage girls, who are one of the highet risk groups to get into trouble with it, about credit - Credit Cardio.

In fact, I was pretty set on joining with Anittah by the end of this round of the weekend, so much so that I stood nearby waiting while she explained some of her thoughts to an older guy who had asked some simple question. What happened next happened so quickly, I’m not sure how it did. When the old guy moved on, this pair of developers showed up suddenly, shoving their cards into Anittah’s hand. Apparently, they had some platform they work on and wanted to apply it to her project. They assured her they could build it with very minimal effort. A deal was struck, and after they left, I was dumbfounded. Had I simply moved too slow? Surely I could get in on this project, still. I talked with Anittah, who seemed optimistic, but not technically savvy enough to know that a custom platform would only be useful to the people who were familiar with it – she would basically be reliant on these two guys for the whole thing unless their platform was simple or widely-used enough to be adopted by other people that would join her team. Sadly, not only did she not understand this, but the two developer guys seemed completely unwilling to work with another developer, or at least, I didn’t have the inclination to convince them otherwise.

I suppose the lesson here isn’t just for me (“Move faster!”), but also for entrepreneurs without technical knowledge. You really have to watch your team and hear what they tell you, because this one detail excluded others from participating. I think that some other developer might have joined her team in the end, but still… Anyway, I was bitter.

So I went off in search of another team. I returned to Adelaide, who was someone that I met while waiting in the auditorium, to see how she was doing. Her pitch was for a travel site that helped timid travelers commit to all of those fun off-beat adventures you’re always seeing on the travel channel. People like the idea of travel, but have certain fears that make traveling nerve-wracking, and her idea was to produce a site that would mitigate that fear.

Well, I like travel, for sure. And Adi and her husband, James, were very easy to get along with, as were the others who had joined her team. Kim, the only other developer to sign up with our team, was a great fit for me, being very competent at the front-end work, while I could concentrate on the back. Kim’s boyfriend, Jeff, was well-traveled and charismatic. And Luke rounded out the team with his Wharton credentials and travel experience. Altogether, the makings of a good work unit.

We chatted a little about the project, then retired to a gastropub to discuss beer, our travel experience, and what we were going to eat for dinner. By the time 12:30 rolled around, we had a pretty cohesive unit.

Saturday, we spent putting the project together. It’s kind of a blur, even as it happened only a few days ago, just because we did so much. We acquired hosting. We chose version control, platform. We all decided what the site was going to offer and started to assemble content. It actually started to come together.

One weird thing was that we kind of seemed to be expected to just go. The organizers suggested that we appoint roles, and that was about it. There were coaches roaming the floor, available to help, but more often I found their intrusion annoying. Rather than asking helpful, directed questions based on what we were doing, or offering suggestions about how to go about any of the phases of building a successful presentation, they always seemed to drop in in the middle of an important team discussion with some random useless question. I think we really could have made better use of the coaches, making sure they were helping with the things we were actually doing and pointing us in the right direction for the next action. And yet, it’s surprising to me with what little help we got or asked for that we made anything viable for the end presentations.

By the time the organizers rolled around at 10pm Saturday night to tell us the open bar was open, I was pretty deep into coding my part of the project. For the first time in a long time, I’d been given something to start from scratch that was interesting and actually starting to get somewhere, fueled by a small team of people who were also interested in getting something useful done. There’s really nothing quite like that experience. Something that would be very attractive to me now is continuing to work like that, in a small team, in person, with competent, intelligent people that I enjoy the company of, for as many consecutive 14-hour days as it takes to get it done or go insane trying. But we all took a trip over to the bar, just realizing that we needed a break.

The University of the Arts building that we used closed at 11:30pm, so we called it a night shortly after the one beer from the open bar. I opened my dev environment at the hotel and coded until 1:30 or so, but after the long day, it felt good to finally pass out.

Sunday morning, things really started to come together with what we were building. The database hooked up, the content from the team was going in, Facebook logins worked, the design Kim put together with virtually no resources was an amazing feat - one that I think most of the other teams didn’t come close to. Sure, there were glitches. Production deployment was a little sketchy. I made some mistakes. It happens, but in the time-limited environment it was frustrating. But in the end, we had our site, Off-Track Online.

Adi and Jeff were putting together a presentation for the culmination of our work. They used Prezi, which is a kind of Flash-based presentation system. In combination with the compass rose we used for the logo, it turned out pretty snazzy.

I admit I was a bit worried about some things. Our team did tend to split a bit along technical/non-technical lines. I didn’t really have a good idea of what was going on with the presentation, and we didn’t show a lot of what we had going on with the site. As a result, I think we could have showcased our work a little more, because we had more actually done than a lot of the other teams. I never heard the presentation myself before it was presented, and I think we probably could have gone through a rehearsal to make sure everything was clean and on-point. In the end, all of the ideas were great, but I felt they could have been a bit more focused. Still, Jeff and Adi did a great job presenting the product to the crowd, and represented us well.

So around 5pm we all headed to the auditorium for the presentations by the 18 teams. Each team got 5 minutes to present, and 5 minutes for potential questions, and that was it. Then the judges would convene and render their decisions.

The teams did a really good job presenting what they spent the weekend building. My favorites included Truxi, which is a service that pairs people who are moving with people who own trucks so that they can rent the time. The presenter knew the idea very well, had shown that there was a market for the service, showed that there was money to be made doing it, showed projections of the money coming in that were realistic based on surveyed demand… I thought it was impressive.

Credit Cardio was also a pretty good presentation, and Anittah was very energetic. The presentation had a different focus from when she described it in the pitch, seeming to try to cover a broarder market. The site they constructed was clean, but a little sparse, and the functionality seems to be supplied from a bunch of odd sources, rather than being something that was built specific to purpose. In the end, I’m not sure what those original guys that “ran me off” contributed.

Seed Invest, whose initiator was one of the people I spoke to before the event even began, was also in the top three, offering Kickstarter-like services but for equity, based on the recent provisions allowing this in the jobs act. The site is pretty, but has very little active functionality.

One of the projects closest to our milieu was Itinerate, which is a site that helps you build detailed itineraries for your travels. It’s not the same as our idea, but meshes pretty well. Actually, combining both of these sites with something that lets you book trips, organize your plans ala TripIt, and then diary and publish your travels would be a fantastic, full-service application.

I don’t mean to say that any of the projects were sub-standard in development. Ours could even use some polish. I just feel like, in comparison to the other teams, we accomplished a lot more real, custom work that could be re-used if we continue to move the project forward. Most of what we saw from other teams in terms of what they had built seemed to be pretty mock-ups, whereas ours was actually at least “something”.

I thought that we probably could have done a better job with organizing our presentation at the end, and I think we only suffered because none of us knew as well what to expect or deliver. Now having seen several excellent Startup Weekend presentations, I can imagine how we could improve ours. It would once again include the elements of an essential pitch - problem and solution - but also focus specifically and clearly on things I know we had answers to:

• Demonstrating that the idea is one that people will pay for and that the market does exist.
• Clearly outline how the project would earn money.
• Show the level of completeness of the project in a true live demo.
• Explain how well-assembled the team is for the job, both in terms of expertise and ability to coordinate

Many of the teams did really well in one or two of these areas, but not in all of them. Perhaps that is why Yagglo won first place with the judges. Their site doesn’t show the thing they built, and neither does their slick YouTube video. Having seen the in-development app working first hand, I can tell you that while it does do some of the stuff in the video, it’s glitchy, and nowhere near as polished. The judges had to have been impressed with a very-well-crafted slideshow, along with a reasonable coverage of the criteria (above) required to have a winning presentation.

After the three days of the event, I wasn’t enthusiastic to go out to the open bar and DJ, but I was pretty hungry for some food other than what they’d been serving at the venue, so I went out with the Off-Track Online team to Fadó. We hung around with the other participants, chatting about our success and potential future plans before I took the long drive back home.

In all, the event was a success. For me personally, it was a great learning experience. I learned a lot about initiating startups and working with other people. I met a ton of cool folks, especially my team of “nomads”. There are other lessons that are personal and harder to articulate as well. But all good.

One thing to consider after one of these events is whether to continue the partnership that produced the results over the weekend. Truly, I was so focused on just getting through to the end of Sunday night, I wasn’t even considering what could happen afterwards. I think that if we can focus the project into something that makes money, it would certainly be worthwhile to continue development for it.

As far as future Startup Weekends go, I’d love to try again. I’d like to get a good idea of my own. I’d like to pitch it and hobnob with the other attendees and try to get a team on board. And while my skillset tends more obviously toward development, I think I’d like to get a bit more involved on the business and presentation side in the next round, just to see how far I can take it. After all, the reason I did this was to learn how to apply this breadth of knowledge to my own startup ideas.

But after all that, I want to thank my team once more, who were fantastic, accepting, talented, experienced, fun folks who I’d work with again anytime.