Starting a StartupWeekend in 9 Days of Chaos

For the past 7 days I’ve been working round the clock to organize and promote a StartupWeekend in San Jose. It start in two days. A ridiculous and ill advised timeline.

To be honest, I didn’t think we were going to do it. I started getting in touch with the good folks at StartupWeekend late in the game with only a month and change to go and only managed to get someone on the phone with two weeks to go.

The suggested timeline for organizing a StartupWeekend is 3 months…but like they say…

If You’re Going to Do Something, Go All the Way…

Jorge Zavala from TechBA wanted to do this weekend in order to offer a bit of cultural indoctrination for the 40 something Mexican entrepreneurs coming in for a month long lean startup and customer development bootcamp that Jorge asked me to design. The idea was to offer a palette cleanser for the brain, a trick I picked up from Jonathan Spottiswoode in my days as a musician.

The basic theory is that when you’re playing NY clubs, the band before you probably sucked. In order to capture the audience’s attention and reset their expectations, you needed to do something in your face and chaotic to shock people into not expecting anything. The ideal is to return the audience to tabula rasa.

After Joey and Shane agreed to let us put one on (after we found a venue) we had nine days left to organize and promote it.

We’re only ten tickets away from selling out.

Marketing in a Hurry

I don’t have a hell of a lot of time free to write this, so let’s just say that things are hectic and fairly disorganized. I’ve been doing everything I can think of in whatever order I thought of it. So it will come as no surprise to those that know me that I only thought about promoting the weekend on my own blog with two days to go. But here are some other things I did which I recommend if you’re in a similar position:

  • Send an email to everyone you know, everywhere

I sent out an initial blast of 1700 emails to a large chunk of my address book including all of my LinkedIn contacts. I used MS Entourage for the mail merge which was bloody awful. Don’t use it. Unfortunately I had few options. The email broke the easily tweetable link and the fonts were screwy, but it got out and people responded.

They perhaps responded even better given the poor state of the email which clearly said, “I have no idea what I’m doing, please help.”

This was the most important thing I did. Tap my personal network. After the initial blast, I’ve exchanged another ~500 emails with people who suggested avenues of promotion, retweeted things, bought tickets, and otherwise acted as cheerleaders.

One guy called me an idiot. Oh well. All in all a fair tradeoff.

  • Tweet like crazy

The general idea is simple so I won’t go into it. I used hootsuite and to set up a steady stream of tweets related to the event. I also made specific tweets mentioning the speakers, mentors, judges, and sponsors. There is no better way to get a RT than by publicly saying “Thank you” to someone and @mentioning them.

I also had a friend build a quick app that @spammed people in the San Jose area with a personal appeal to help spread the word. It also DMed my followers in order of most influential. Importantly, the tweet contained their first name to personalize it. Both of these things were moderately successful and totally worth doing. In the future I would only lower the per day count so it’s not too spammy.

  • Post on every and LinkedIn group you can think of

’nuff said

  • Reach out to other event promoters

Other event promoters were key. People like Cass Philips and Edith Yeung were very helpful in terms of making a quick promotion deal and learning about possible venues.

  • Put it on plancast

This was suggested to me by the Plancast crew when I emailed them in my initial foray. Which is again why you should reach out to your network. They’re probably smarter than you.

  • Beg

As in, “don’t be afraid to.”

That’s it for now. If you haven’t heard the word yet, you have now! Go buy a ticket! We’re almost sold out!

[Update: We sold out.]

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