My Best Mistake: I Could Have Started An Uber-like Service in 2008

This great post by Justin Rosenstein of Asana reminded me of a similar story of my own. Thanks for the inspiration, Justin.

In early 2008, I was looking to start my second business. The App Store had just been announced and would launch that summer, which got me thinking about ideas for apps. Transportation efficiency is a subject I’m passionate about, so I came up with a concept for using iPhones for on-demand transportation within cities utilizing the excess capacity in black-car fleets. I talked to some SF limo companies to vet the idea, built a financial model, mocked up the product and even registered the domain name teleportr.com (as the service would be so magical it would be like teleportation – get it?).

There was only one problem. It was illegal. I called the SF taxi regulators and described the business. They said I could certainly go ahead, as long as I wanted to go to jail.

So I shelved the idea. I also shelved 3 other equally ambitious, but challenging-to-execute ideas (that I won’t be disclosing right now – maybe I’ll start them some day in the future…). And instead, I went a “safer” route, launching DealBase.com. The goal wasn’t to change the world, but to create modest cash flow by capturing SEO traffic in the travel deals category. To this day, DealBase continues to be very profitable and the talented team there executes well against new initiatives in the coupons category, where they have a lot of innovation planned for the year.

We hit our goals, but didn’t change the world, and I watched as the vision for Teleportr was implemented by a company named Uber, which has gone on to reinvent the way we move around cities. I’m thrilled at the success of Uber, both because it validates the vision I had and because it’s a service I use religiously. And while part of me still regrets not pursuing Teleportr, I’m not at all convinced I could have executed as well as my friend Ryan and the other Uber founders, who have managed to change the taxi regulations to support changing technology.

Not moving forward with Teleporter taught me that launching a business with modest goals is just as hard as launching one with great ambitions, and that I do my best when building big, world-changing products and ideas. Had it not been for this mistake, I wouldn’t have had the ambition to launch HotelTonight, and the confidence and bravery to compete head-on against $100 billion worth of legacy travel companies.

Lesson: If you have a big idea, pursue it. I wouldn’t be here if it weren’t for learning that first-hand.

Image from senhormario