Diary of a Startup Weekend- Part I

I remember telling my friend last Friday about how I was going to spend the coming weekend. After explaining what I imagined Startup Weekend to be all about, he said ‘It sounds like work!’

And in a sense, he was right. It was a lot of work. At the same time it was the most fun I have had in a long time. While in the thick of it all, there isn’t a whole lot of time to reflect on the experience. In fact, I didn’t even take any pictures. I know from a recent trip to the Caribbean that it is a matter of days before you lose the tan. So, I decided to do a blog post about the experience before the memories fade.

How I ended up at #startupweekend in the first place

Everyone has a different reason for arriving at Startup Weekend. I first heard about it about a year ago from my friend Skip, who participated in the two previous events and was spending this one, his third, as a mentor. One of the teams he was a part of previously went on to get some funding from Portland Seed Fund. He and I have spent a fair amount of time dreaming big over expensive cocktails (we both have day jobs), and he encouraged me – dared me! – to attend. When the latest event was announced I signed up before I could back out. Good thing too as it eventually sold out.

Friday Night – Pitching or Catching?

I arrived without any plans to ‘pitch,’ which entails getting up in front of the audience and selling your idea in 60 seconds or less. Once I got there and felt the electricity in the room, and came to the realization that about half the audience would be pitching, I decided to throw my hat in the ring. I’m not sure I recommend doing this unrehearsed! As a drummer, I’ve spent a good part of my life behind a drum kit focused on entertaining folks, and this context, I have no problem grabbing the mic and talking up the crowd, but this felt different. There were no props. No music. If I were about to sing the National Anthem , I’m certain I would have fucked up the lyrics. I did it anyway . Though the votes for my idea didn’t qualify me for the 17 team cut, (Note: it helps to have a catchy name thought up in advance), It was definitely the right thing to do as a way to introduce yourself.

Then the time came to partner up with one of the 17 finalists. This was a nerve racking process of chatting up prospective pitchmen (and pitchwomen) and deciding who you think you should spend the next 48 hours hanging out with. I ended up on a team called ‘Habit Coach’. I liked the leader, but when I ended up in a room with nine people (larger than average), at least three of whom had strong opinions about what the product should or shouldn’t be, I had my doubts. I got home the next morning at 1 am, and as I replayed the nights events, didn’t fall asleep til about 2.

Saturday Morning Free Agency

I have two small kids, and so I was up the next morning at about 6. I went on a run, and despite the lack of sleep felt great from the buzz of the event. Better than great. I was pumped. I got in at about 8:30 and asked one of the organizers if it was ‘cool to defect’. He said simply “that’s what this is all about.” And so it was I joined the 12 carrots team. I became their fourth member.

To be continued. . . .

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  • http://www.facebook.com/shashi.jain Shashi Jain

    “I got in at about 8:30 and asked one of the organizers if it was ‘cool to defect’. He said simply “that’s what this is all about.”

    Love it! Can’t wait for the second part!