A summary of early and growth years of Uber and Airbnb. Felt quite one-sided though—most attempts at addressing the criticisms felt muted. Wasn’t as in-depth as ‘The everything store’ either.

Then the whole tangled story of the last year came tumbling out, from the inspiration at the design conference to the disastrous South by Southwest to the nominating conventions and the unlikely cereal gambit. “Wow, you guys are like cockroaches,” Graham finally said. “You just won’t die.”

Cockroach was Graham’s word for an un-killable startup that could weather any challenge, and it was the highest possible compliment in his startup lexicon.


I’ve made peace with the fact that Silicon Valley is so random. You have to make peace with it or otherwise you’ll never get a good night’s sleep in this town.

—Naval Ravikant, on missing investing more in Uber’s first round


Gurley offered some free advice about focusing, suggesting launching first in specific neighbourhoods rather than an entire city, before hanging up.


Wolpert probably should have taken Gurley’s offer, he mused years later, but it would have required ditching the investors that had already committed. In other words, he would have had to ruthlessly prioritise the best possible outcome for his company, despite his prior personal commitments.

“I was a Boy Scout. I was going to go with the date the brought me.”

— John Wolpert, Cabulous


“It was like watching a shark devour a seal. We are living in an era of robber barons. If you have enough money and can make the right phone call, you can disregard whatever rules are in place and then use that as a way of getting PR. And you can win.”


An online home-sharing service called Couchsurfing won devotees and attention five years before the rise of Airbnb. It wasn’t bad timing, stubbornness, or chronic niceness that doomed it, but something just as deadly in the cutthroat world of business: idealism.


“You want to back entrepreneurs who, even when the chips are down and things aren’t working and everyone says this isn’t meant to be, have so much love for the idea and so much passion that they just persevere. Startups are very romanticised and most people are completely clueless about how you just have to will it into existence.”


All the lethal mistakes of the other nonstarters were wrapped up in Zimride. The founders were too nice. They were idealistic. Their idea was too early—the great wave of smartphone ubiquity and social networking was just gathering momentum. But they were also pragmatic, and they believed in that Silicon Valley notion referred to as “the pivot.” As long as there is money in the bank, it’s never too late to change business models and seek more profitable pastures.


McAdoo introduced himself to Brian Chesky, Joe Gebbia, and Nathan Blecharczyk that day and was struck by their approach.
The vacation-rental startup founders he had talked to were trying to make the experience better for travelers; the Airbnb guys wanted to make it better for hosts.


Chesky was moving slowly, but at the same time, he was frustrated that his imagined success wasn’t arriving quickly enough. “Every day I was working on it and thinking, Why isn’t it happening faster?” he told me. “When you’re starting a company it never goes at the pace you want or the pace you expect. You imagine everything to be linear, ‘I’m going to do this, then this is going to happen and this is going to happen.’ You’re imagining steps and they’re progressive. You start, you build it, and you think everyone’s going to care. But no one cares, not even your friends.”


There was another unintended consequence of Christiane Hayashi’s fight with Uber. The young startup received a torrent of publicity from Silicon Valley’s technology blogs. Between that and the already strong word of mouth, the number of Uber rides started bounding upward by 30 percent each month.

Note2self: 30%/month—the target growth rate at early stages of a startup


“Nothing we do is riskless. That’s why it’s called risk capital. This thing obviously had a really interesting upside but it also had some hair on it. Brian knew what the hair was.”

On risk investing, and the right executive.


On Uber’s city executive teams…

… based the Seattle operation on the three-person structure in New York. The general manager supervised the overall business in the city and was accountable for its growth. He or she needed to be entrepreneurial, scrappy, and aggressive in talks with regulators. An operations manager, usually an analytical type like a management consultant or investment banker, was in charge of signing up drivers and making sure there were cars for every passenger who opened the app. Finally, a community manager, a creative type with marketing chops, worked to stimulate demand among riders.

This became the early template for local offices, Uber’s equivalent of a SWAT team, able to drop into cities and rapidly spin up a new business.


Perhaps my favourite section in the Uber story…

If they couldn’t add drivers faster, perhaps they could redirect the ones they had to the busiest neighbourhoods. So Geidt and the ad hoc New York team began directing drivers to spots where people were most likely to embrace an upscale thirty-five-dollar car ride, places like Wall Street, the Upper East Side, and SoHo.

Uber basically broke New York City into a series of targeted micro-cities. … Sending drivers to the places they were needed most would ensure a good experience among the social groups most likely to use Uber; they would then tell their friends, generating demand that would in turn make the service more lucrative to drivers.
“We learned that you can’t bring a San Francisco solution to New York and expect it to work.”


On communicating dynamic (surge) pricing

“Our messaging was not that great. We didn’t do a good job of communicating to people what it would cost.” Even Kalanick, somewhat contrite after the media maelstrom, told me a few months later that the details of communicating price increases, even font sizes and wording, mattered a lot. “We tried to unwind decades of fixed pricing in personal transportation in one night,” he said.


Cheh later compared Uber’s reaction to the stubbornness of the gun lobby, with its unwillingness to yield even an inch.


Travis’s Law

Our product is so superior to the status quo that if we give people the opportunity to see it or try it, in any place in the world where government has to be at least somewhat responsive to the people, they will demand it and defend its right to exist.


“I was personally always of the philosophy that the great companies, the PayPals of the world, don’t get scared by regulation. I never wanted to be the kind of lawyer that just said no.


On using culture as the USP.

Lyft could have easily been dismissed as an uninspired follower but instead was greeted bas a novelty, primarily because Zimmer and Green had thought carefully about a new set of rituals needed to turn a ride with a stranger into a comfortable and safe experience.

The Lyft founders devised a sort of mating dance for strangers sharing a car. Riders were told to climb into the front-seat, not the back. They were instructed to exchange a fist-bump with the driver. Conversation was encouraged—everyone here was a fellow passenger on a new internet wave that was connecting people and communities through supposedly superior transportation alternatives.


In a grand flourish, Zimmer decided that every driver using Lyft should affix a pink carstache to his or her vehicle’s front grille. … To live in San Francisco in the year 2012 was to wonder, with mounting curiosity, why those weird pink carstaches were suddenly everywhere.


Marzia Zafar, the director of policy of California public utilities commission, who ran the subsequent rule-making process and would write the eventual regulations, cut an unusual figure for a regulator. She was an Afghani immigrant with a Mohawk who had moved to the United States as a child and had once driven a cab herself for her uncle’s taxi company in San Bernardino County.


“Uber execs were extremely hungry and immature and caught up in a whirlwind of money and growth. They got seduced by the possibility rather than stopping to think about their responsibility.”


Brian Chesky, on startup size, growth, and resistance.

“When there’s a cool new business on the internet, that;s great. But when the internet moves into your neighbourhood, into your apartment building, and you don’t know anything about it, suddenly people assume the worst and they have a lot of fears.”

“So there’s a couple of things you need to do. The first thing you need to do is grow really, really fast. You either want to be below the radar or big enough that you are an institution. The worst is being somewhere in between. All your opposition knows about you but you are not a big enough community that people will listen to you yet.”

“You have to get to what I guess I’d call escape velocity. If a rocket takes off, there’s a bumpy ride before you get to orbit, and then there’s a little bit more stillness.


Brian Chesky on engaging ‘haters’

“If people dislike you or if people hate you, it’s often normal to ignore them, to avoid them or to hate them back. The only real solution is to meet the people that hate you. There’s an old saying that it’s hard to hate up close. I have found that. It’s really hard to hate somebody when they are standing right in front of you.”


Travis Kalanick, on value of competition (after China battle with Didi Chuxing)

“… there’s also an economic and business case for it too. Competing makes you strong because it means you’re serving riders and drivers better. As an entrepreneur, you want to see if the way you’ve created is a way that can work.

Sometimes it’s really easy to go and acquire a competitor, but we resisted that.”