I think the more interesting story isn't how Uber won but how Lyft lost. Sidecar was actually first out of the gate with a ridesharing product but Lyft wasn't

I think the more interesting story isn't how Uber won but how Lyft lost. Sidecar was actually first out of the gate with a ridesharing product but Lyft wasn't far behind and soon clearly dominated the space with their ingenious pink mustaches. Sidecar suffered from a classic first mover's disadvantage in that they were overly concerned with regulatory risk which made them too timid. Sidecar's opinion was that the mustache overstepped the bounds between employer/independant contractor and that the CPUC would slap down Lyft and put them out of business (similarly, the bid model that Sidecar used was driven by similar concerns despite the noticeably poorer user experience). I've never seen a product achieve such ferocious product/market fit as Lyft did. During its first year, it was extremely common for there to be hours at a time when drivers were immediately snatched up as soon as they ended their last ride and passengers would wait for half an hour at a time, eagle eyed staring at the screen to snatch up a car. The level of inconvenience that people were prepared to put up with just to use Lyft's product spoke to just how much of a radical upgrade in user experience ridesharing provided and a hint as to the explosive growth that was to come. Lyft was in the enviable position that they held a near monopoly in this space for almost 18 months as Uber tried to reconfigure itself and I remember hearing Travis speak about how the cheaper Uber would be Uber and being skeptical that he could ever overcome such a huge first mover advantage. In the face of all of this, Lyft could have made the "standard" startup decision of prioritizing growth above all else and taking whatever compromises were necessary to service that growth. Instead, Lyft took an alternate path in which they placed driver quality as a longer term priority. I remember during even the most insane supply/demand mismatches, Lyft was still rejecting some 50%+ of driver applicants for not being "Lyft material". I think against almost any other competitor, Lyft could have made the same choices that it made and come out ahead but Uber's raw ability to execute is something that, regardless of what you think of their ethics or culture, has to be admired. Uber is one of those extraordinary companies that prizes execution ability culturally in the same way that Apple prizes design. Lyft should have rolled out into other cities faster, Lyft should have gone international, Lyft should have dropped its prices more aggressively and taken the hit on driver quality. All of those are recoverable errors unless you're facing up against someone like Uber who rolled out an aggressive expansion plan and then relentlessly executed against it with the wheels barely falling off. This is all easy to see with the benefit of hindsight but I remember living through that time, with friends at all 3 companies and watching them grope towards an uncertain future while doing the best they could.