The Startup Weekend Experience

I attended Startup Weekend Boston this past weekend, had enormous fun and helped launch a new business.

If you’re not familiar with Startup Weekend, it’s a weekend-long event where teams compete to bring businesses from concept to launch in 54 hours. Today’s post provides a play-by-play of what one of these weekends looks like–or at least my experience of the weekend.

[Disclaimer: I wrote this over the past three days and my memory has failed me on many of the details. If anyone who attended sees anything I missed or that I got wrong, please let me know and I'll update this post. I'd also love to know who won each category at the end and who the judges were. I remembered a few, but forgot to write the rest down.]


We gathered Friday at 5pm in the teacher’s cafeteria at Boston University (BU). Tables and chairs were set up around the room. I sat at a table filled with people talking about their startup experiences, participation in previous Startup Weekends and, of course, the latest iPhone. I listened as ideas for pitches were tossed around.

I immediately met David, a .Net developer at a local consulting company. After a couple minutes of talking, it was clear he had experience. I was looking forward to being on his team, but we gravitated toward different projects.

The Talks

Shortly after 7pm the talks began.

Rob Spectre from Twilio started off with How To Come In 2nd Place at a Hackathon. An entertaining talk filled with crazy slides, Rob set the tone for the weekend. The goal was not winning, but the experience. If you wanted to win, you could easily cheat. But those who went through the process earnestly might just come out with a real business.

Jennifer Freemont-Smith from Smarterer followed talking about building a company focused on experimentation and exploration. Find the rivers that might flow to an ocean of revenue and think in terms of experiments. It was a great introduction of lean startup concepts to the crowd.

Peter Shankman closed out the introductory talks with a hilarious presentation filled with bits of wisdom. Some of it was a repeat of the talk I heard him give at Carolina Connect this year, but it was entertaining nonetheless. My favorite nugget: focus on the concept, not the brand. When he asked what medium had 140 characters, several people mentioned Twitter. The real answer: text messages. 96% of people use text messages, only 4% use Twitter.

The Pitches

At eight o’clock the facilitator asked who wanted to pitch. Everyone who raised their hand was assigned a number. Each pitch was timed to be only a minute long. As people pitched, I and others took notes on interesting projects.

After all the pitches were done, the facilitator gave everyone who hadn’t pitched an opportunity to pitch, in case any of the previous pitches inspired ideas. Six of us decided to pitch in this round. I pitched a mobile app to track food allergies using multi-variate analysis that I’ve had tossing around in my head for a while.

Voting for Ideas

To vote, everyone was handed three one-dollar bills. Forty-two envelopes were laid out on the table and everyone was given 10 minutes to vote for the ideas they liked by placing dollar bills in each envelope. The rules allowed you to put all three in one envelope or spread them across envelopes. I chose to place mine in three separate envelopes, voting once for my own idea.

The money was counted, the envelopes were sorted and the top 15 ideas were announced. Then the chaos began.

Building a Team

The presenters of each of the top 15 ideas spread around the room and began the process of recruiting a team. Some teams sent out scouts to recruit programmers, while others waited for people to come to them.

I had two ideas I was interested in participating with, but a couple others I was rooting for. After not finding the presenter of, I settled on Sponsor Bar, a variation of Hello Bar aimed at event promoters and non-profits. One fellow with an idea for car expense tracking I wanted to succeed, so I spent a bunch of time trying to help recruit people for his team. Ultimately, I and he were unsuccessful and he wound up joining another team.

After an hour or so, the teams congealed. Gerard, the originator of Sponsor Bar, had assembled a team of 8 people–Gerard, Ray, Paul, Ben and Brian were on the business side, while myself, Amit and Ziad were the developers. As Amit and Ziad had not done web programming before, but did know C, we settled on PHP as our development language, with myself as lead programmer. Brian recommended we use the Yii framework, which provided some user management, so we did.

The First Night

Planning began. We broke tasks out into development, marketing, customer validation and business model development. Tasks were assigned to individuals and deadlines set for what needed to be done by 8am and Noon the next day.

By that point, it was almost midnight. We were being kicked out at 1:30am due to BU policy and I had to catch the subway back to my room before services stopped for the night, so I left. We agreed to meet back there at 8am.

On the T ride home, I wrote down some ideas and began to sketch out a design.

Once home, I set up my laptop and started setting up the Yii framework. I had never used Yii before, so went through several tutorials (which were excellent). I drew wireframes of the interface on paper, then wrote out the database structure. Finally, I coded a quick prototype of how the bar would work on the customer’s web site, proving to myself that the technical issues were solved.

That night I went to bed at 3am.

Saturday: The Sprint

Morning arrived too soon. Three hours after sliding into bed my alarm blared.

I downloaded a tutorial for the Yii framework onto my iPad and read it on the subway ride to Boston University. Our team gathered, ate bagels for breakfast and dived straight into work.

Saturday was a whirlwind. I focused on development, joining the business discussions to give my input from time to time. The business team explored business models and target customers while building a landing page, gathering Twitter followers and interviewing potential customers. Throughout it all, Ben cracked jokes to keep the mood lighthearted.

By Saturday night we had a basic prototype working. Gaps in functionality still existed, but the core was there. That night I had intended to stay up to finish the prototype, but by the time I reached home I was so tired I crashed immediately.

Sunday: The Home Stretch

I intended to get up at 5am and start coding. Instead, I hit snooze until 6am. A little light early morning reading on WordPress plugins and user management on the Yii framework and I was off back to Boston University.

Sunday morning, after checking in with the team, I went off and found a secluded place to spend focused development time.

Two hours later, with membership finished I re-joined the team. Brian started working on improving the design of the application while helping out the business team who were furiously working on finishing up our slides for the presentation.

Gerard and I went off to make phone calls to people I knew who were involved with non-profits to get customer validation. Everyone we spoke to liked the idea and gave us valuable feedback on the value of the sponsor bar to non-profits. Critically, we found out how much some would be willing to pay for the service.

Then it was back to development. During lunch I coded a quick WordPress plugin based on a BuddyPress user import plugin I’ve been working on for one of my side projects.

The Dry Run

We were scheduled for a dry run of our demo a 3:40p with one of the “geniuses”, experienced mentors who were advising each team.

Amit worked on getting the Open Flash Chart library integrated for the analytics, so I worked on adding additonal customization options and pulling the data from the database to feed into the charts.

For the dry run, we met with Alexandra. Gerard presented his first two minutes, then Alexandra provided feedback. He needed to tap into his passion and tell a story. Why was he doing this project? What inspired him?

I took this time to finish up the customization code, a bit nervous about making code changes minutes before I was to demo. But it worked and I gave the demo.

The demo gave Alexandra a better idea of the value. As someone who worked with non-profits, she provided additional customer validation and told us to emphasize the management features of the product.

After the dry run, there wasn’t much left for me to do. The software was ready to launch as an alpha release and the demo was ready. I took the time to decompress and chat with people. At five o’clock the organizers began the process of kicking everyone off the tables so they could set up for the presentations.

People started to arrive and suddenly the room felt crowded.

The Presentations

Presentations started around six o’clock. Each team was given 5 minutes to present and 3 minutes to answer questions from a panel of three judges.

For each presentation, the team would congregate on stage. Slides had been uploaded to SlideShare and everything was being driven off the same laptop. Some teams used multiple presenters while others used a single presenter. Some acted out a brief skit and still others had recorded videos.

My favorite business ideas were:

  • Inspirater
    A clearinghouse for event speakers, both new and established. Conference attendees could rate and comment on speakers while event organizers could use these ratings to search for relevant, highly rated speakers for their events.
  • 8 Hour Intern
    Hiring people, not resumes. A new way to hire people by hosting them during one day internships.
  • Bite Rite
    Customized menus at restaurants usng mobile devices for food allergies and preferences.
  • Tabber
    A guitar whose frets light up to show you how to play chords and songs. Built into a custom neck that can be added to any guitar. For their demo they showed the guitar teaching Here Comes the Sun by The Beatles. Awesome project.

And, of course, there was our team:

  • Sponsor Bar
    A bar appearing at the top of web sites to showcase sponsors, providing non-profits an additional benefit to sponsors and analytics to help justify renewals. It also enables non-profits to manage sponsors listed on their web site without talking to their web site designer.

You can view the slides for all the presentations here.

Our presentation was second-to-last in the first group. Gerard did the main presentation, while I handled the demo. It didn’t go as planned. The presentation struggled between explaining the overarching vision of sponsor management software and the value of the first product, Sponsor Bar.

Meanwhile, I had forgotten I was auto-generating passwords and couldn’t log into the demo. It wasn’t until the question and answer sessions that I found the e-mail on my phone with the password and was able to log in and give a quick demo.

The Awards

After the presentation, everyone lined up at the dinner buffer and got a plateful of bread and pasta. Food was much appreciated by this point.

Around 8pm, the awards began. For the main competition, awards were given for first, second and third place. Art Cereal, a marketplace enabling student artists to sell their art cheaply, won first place. First and second place awards were also given for best design and biggest market potential. Tabber won one of these, while Sponsor Bar took second place in the design category.

After the awards, we took a team picture. Then Brian, Amit and I headed down to the Sunset Cantina where the stragglers were meeting for a post event drink. Everyone else headed home to do homework or sleep.

A New Business

After the weekend, what happened?

Gerard plans to move forward launching Sponsor Bar as a business. He has a great opportunity to build a niche business and learn in the process. I may help him as an adviser and others may be helping him on the implementation. I made it clear it was his business. I had fun coding over the weekend, but don’t have time to continue. The code is his to do what he pleases with.

So, if you are involved with a non-profit, or know someone who is, register at to be informed when the official application launches. Manage your sponsors, provide new sponsor benefits and justify renewals with Sponsor Bar.

A Few Insights

Being embedded in a team at Startup Weekend was an extremely rewarding experience. I’ve been running my current company for 8 years and this was an opportunity to step out for a bit and try something new.

I also got to see everyone’s working style to discover who I might want to hire or work with in the future. Even with the people not on my team, I built deeper relationships than I ever could at a typical networking event or conference. Winning didn’t matter–getting through it together as a shared experience did.

Next month is Startup Weekend Charlotte and I’m psyched to attend. I’ll be back from Boston by then and I plan on bringing a convoy from Asheville. If you live in Asheville and are interested in joining, let me know. If you live in Charlotte, register now. And if you live elsewhere, check the list of Startup Weekends that happen every weekend all around the globe and find one near you.

It’ll be an experience that changes your life.

Have you attended a Startup Weekend? What was your experience like?

1 comment

  1. Jim Van Fleet says:

    Can’t wait to meet you at CSW 3!

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