Why does Uber Inc feel like a nark and Airbnb feel like a friend?

Uber was started by Garrett Camp and Travis Kalanick in 2007 because they wanted to get around town in style without having to pay steep costs todo so. Travis had just sold his company, Garrett too. They were two rich dudes looking for what’s next.

However, Airbnb was started by Nathan Blecharczyk, Joe Gebbia, and Brian Chesky. Two of which couldn’t afford to pay rent so they started renting out their apartment to travelers.

Almost a decade later, Uber is worth $66 billion and Airbnb is worth $30 billion — the leading valuations in the world of startups.

Despite the success of each, Uber feels like a cold corporate giant, while Airbnb feels like a travel companion. Uber tries to sell you on the idea of controlling your life, “a car, when you want it, anytime, anywhere.” That is, until you’re crammed up next to someone you’ve never met paying $2.50 because we’re both to lazy to walk to the bus.

Airbnb, however sells the idea that people are basically good, and that traveling across the world to stay in a stranger’s home isn’t at all awkward. Even still, Airbnb doesn’t feel like a shmuck is using you (amongst thousands of contractors) to get rich.

Don’t mind me, Kalanick is brilliant. He’s forceful, visionary, and makes it happen. He’s pushed through major losses ($3B and rising), out-date city restrictions, and tough competition both domestically and internationally.

The problem is, I don’t believe him. Travis claims he’s paving a better future, but is he? Does Uber as a company feel liberating?

When Brian Chesky dreams of making vacations magical for everyone. Do you believe him? Does it feel like he’s just disrupting for the fun of it, or that he actually cares about travel for everyone?

A company is only as great as its leader. With Travis, I see a capitalist. Someone who saw an opportunity and made it happen. Nothing more, nothing less. Driven by his ego to change the world for the sole reason to see if he could.

When I see Brian, I see someone who believes what he says. A Steve Jobs. Someone so relentlessly concerned with producing a quality experience that he doesn’t have time to count the cash.

Travis is always counting the cash, always seizing the opportunity. Isn’t this the hero we often see depicted by Marvel? Brash, brilliant, ruthlessly in control. Travis didn’t want Uber to become a value brand, but he had to.

Transportation isn’t a luxury, it’s a means to an end. Travis wanted luxury, but those outside the Silicon Valley bubble who haven’t just sold their startup can’t afford to pay $20 a ride.

What went wrong for Travis? Because Travis started Uber to get in on the next big thing, he never really cared about the people that made it possible: drivers. Drivers were always a means to an end. A way to grow, to scale!

Uber has always been a company for the people, the executives mostly. Have you ever met a happy Uber driver? It probably had nothing todo with Uber.

What went right for Brian? Because Airbnb was always about making travel magical, Brian always focussed on the people who made it possible: hosts. He took care of them, listened to them, and opened up even more revenue streams for them!

Airbnb has always been a company for the people, the hosts and travelers. Have you ever met a happy host?

The point is, Brian takes care of his people. Travis takes care of his company.

How does Airbnb make you feel? How does Uber make you feel? Do you ever feel bad for an Uber driver barely making it? Do you ever feel like a shmuck for paying $2.50 for a ride and not being able to tip?

Does Uber make your feel liberated, or Airbnb?