My Best Friend’s Wedding: The Startup

Update: No, it isn’t TweetToCall – although I love that project (yes, it still works and has a few thousand users now) and do think Twitter is going to become the new phone book.  TweetToCall should be a feature of Twitter, and if anyone wants the code etc. I should just open source it.

You know that Julia Roberts movie where she doesn’t realize how much she’s in love with her best friend until he calls to say he’s getting married to someone else, and then falls off that bed?  That’s how I feel about my startup idea getting founded and funded by someone else.

To be clear, I’ve probably had thousands of ideas for startups – but I’m a fan of failing fast and most of them have been crappy, or usually technically “cool” but not monetizable.  That’s okay.  But this idea was actually something I pitched in the few moments I had between leaving Whrrl and joining Twilio.  It was something that nabbed me an offer to be an EIR with a reputable VC, which I was honored to receive but ultimately turned down.  Most importantly, it was an idea that I am still obsessed with.

Today, I read that someone I know of and respect a great deal received some funding for this business, and is forming a company to execute on it.  It haunts me.  I know I’ll get over it, and I’ll be watching closely in the next year to observe how it goes as I consider whether or not it is the startup I’ll found someday.  I can’t deny part of the pain is over not being first, but that is mainly pride.  The rational part of me (or mercifully rationalistic) reminds myself that it may benefit me in the long run not to build a product in a consumer market that will require so much education.  Time will tell.

Bottom line: the timing is wrong for me.  I love my current company so much, and it is exciting, challenging, fun, growing, amazing — all the things we dream of when we talk about starting companies.

Ideas are a easy to come by, but ideas that you can imagine executing on for YEARS of your life are not.  When I learned of Twilio I was immediately intrigued, and when Jeff approached me about joining the company I couldn’t say no.  The alignment of market, team, and timing is undeniably awesome.  Twilio is an idea I enjoy walking around inside of, thinking about constantly, living and breathing the brand.  If I ever found a company as incredible, cohesive, and useful as Twilio I will have succeeded — so for now I’ll have to swallow this momentary pain, and look forward to the exciting future.