My Personal Startup Weekend

There’s really no such thing as a ‘holiday break’ for a startup founder — we’re “always on”.  But this Holiday Season I found myself clawing at the walls waiting for December to pass so that I could resume fund raising activities for MoonTango.  In case you’ve never tried to raise capital from mid-November through December, sufficed to say you’re odds of success are very low and odds of frustration are very high.  You’re better off trying to grow a giant bean stalk from magic beans and seeking to fund your company through the sale of golden eggs.

Feeling very unproductive, I decided to build something.  And as is my wont, I decided to build a company.  But there were conditions.  It had to be something that:

1) was relatively small in scope, so I could finish it before the holidays were over.

2) my team (i.e., me for now) could execute on, including tech and design.

3) was a real solution that could (even if it didn’t actually) get real customers by the time it was launched.

It dawned on me… if you substitute “weekend” for “holidays”, these are all criteria that you’d want to strive for if you were doing a Startup Weekend event.  I was doing my own personal Startup Weekend!  But rather than compressing the time to a weekend I was compressing the time to about 3 1/2 weeks… a few hours here… a few hours there.  I didn’t keep track of the total hours I spent, but wish I would have.  After the fact, I tried to estimate how much time I’d spent and I really don’t think it was much more than the 54 hours that make up a Startup Weekend.

What I built and launched was Xaffle, a virtual raffle system that allows you to launch, manage and enter a raffle/drawing/contest using only SMS text messages.  The inspiration came from a problem I’d experienced at the November Poker 2.0 event.  GeekWire was sponsoring and they wanted to give away a ticket to the GeekWire Gala.  We knew we couldn’t just give the ticket to whoever won the poker tournament because they might not be able to make it that night.

When the time came to pick a winner we decided just to have everyone who wanted the ticket come up and cut cards to see who won.  It was an apropos method to determine a winner, given that we were at a poker event.  But we had to delay the tournament in order have everyone come up… negotiate how to handle the case of a tie, where two people cut the exact same card, or at least the same denomination — “what’s higher… a heart or a spade… anyone remember?”

At that moment, I wished there was a way I could just have everybody send a text message and then pick a random winner.  I had built a little Twilio app for Dealometry a few months prior that just allowed guys to text their email address to subscribe for deal alerts… and several SMS-based reporting tools for MoonTango.  Twilio is so easy to use that it took about 30 minutes to get a functioning app up and running and another hour or two of tweaking and it was done.  Someone, I thought, should build a simple raffle app using the Twilio platform.  Turns out that ‘someone’ was me.

Here’s the kicker.   Xaffle is going to debut at Startup Weekend this very weekend!  We’re doing three Xaffle drawings, each demonstrating a different capability of Xaffle.

The first is a trivia question where people text their answer in and the first three correct entries win an autographed copy of Lean Startup by Eric Ries.  Xaffle automatically checks their answer against the “right answer” and picks the winners based on the time that the answer was received.

The second is a voting contest where the entrants all submit their votes and Xaffle automatically tallies the submissions to see which was entered most often.  The question: What is the best drink to celebrate the launch of a startup?

The third is a simple prize drawing.  Participants can enter up to three times and the winners are randomly and automatically picked by Xaffle.  Entrants submit their email addresses and winners will receive a text notification that they’ve won.  By submitting their email address, each entrant is also subscribing to Dealometry.  This is the ‘lead gen’ aspect of Xaffle and in part what makes Xaffle’s business model potentially viable.  Dealometry is donating a pair of cool video camera eyeglasses as the first-place prize and Madrona Capital is donating a couple of nice tote bags for 2^nd and 3^rd.  Thanks Madrona!

I am a raging fan of Startup Weekend and it’s a delight to launch a product that was inspired by the Startup Weekend process at a Startup Weekend event.

Lucky me.