The Upstarts
The Upstarts

The Upstarts

Like Uber, cash is deleted from the equation; Airbnb collects the transaction fee from the guest when the lodging is booked and remits it to the host, minus its cut, after the stay is complete. (Location 137)

Tags: airbnb, remove friction, cash, uber

Airbnb and Uber didn’t spawn “the sharing economy,” “the on-demand economy,” or “the one-tap economy” (those labels never quite seemed to fit) so much as usher in a new trust economy, helping regular folks to negotiate transportation and accommodations in the age of ubiquitous internet access. (Location 152)

Tags: airbnb, uber, trust

At the center of this maelstrom are the young, wealthy, charismatic chief executives: Travis Kalanick and Brian Chesky. They represent a new kind of technology CEO, nothing at all like Bill Gates, Larry Page, and Mark Zuckerberg, the awkward, introverted innovators who typified the previous generation of tech leaders. Instead, they are extroverted storytellers, capable of positioning their companies in the context of dramatic progress for humanity and recruiting not only armies of engineers but drivers, hosts, lobbyists, and lawmakers to their cause. (Location 186)

Tags: stories, ceo

Every company creates its own origin myth. It’s a useful tool for expressing the company’s values to employees and the world and for simplifying and massaging history to give due credit to the people who made the most important contributions back when it all started. (Location 742)

Tags: stories

Note: Companies often make up their origin stories!

He had dubbed his San Francisco apartment, where entrepreneurs would gather to jam on new startup ideas, the Jam Pad. It was a kind of entrepreneurial safe house, a place where like-minded obsessives could gather in front of a whiteboard and debate the intricacies of building internet companies. (Location 754)

Tags: innovation space

(when passengers are standing on the side of the road hailing a cab, all taxi companies are equal). (Location 1078)

Tags: uber

“Life is short,” Fenton said in an interview at the time, explaining his thinking. “I want to do meaningful things. Money seems like it can come easily. If you just want to focus on money that’s fine. I want to do some things that I find more interesting.” (Location 1243)

Tags: seek a calling, life principles, money

A student at Cornell University’s school of hotel administration, John Zimmer had learned that the key to running a profitable hotel business was high occupancy and great hospitality. The transportation status quo offered neither. (Location 1309)

Tags: business mechanics

“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,” says her partner Mike Maples Jr. “Startups are very romanticized and most people are completely clueless about how you just have to will it into existence.” (Location 1336)

Tags: entrepreneurial, startups

Internet marketplaces thrive when buyers and sellers are matched in ways that wouldn’t otherwise be possible, saving everyone time and money. (Location 1345)

Tags: remove friction

“It’s better to have a hundred people that love you than a million people that sort of like you,” (Location 1383)

Tags: community, quotes

“Don’t worry about competitors; startups usually die of suicide, not homicide. (Location 1384)

Tags: quotes, competition

He was in his early forties and typically wore the I-don’t-care-about-your-social-customs sartorial combination of cargo shorts, a polo shirt, and sandals. (Location 1384)

Tags: societal norms

In late 2009, a few months after it had graduated from YC, Airbnb appeared to create a mechanism that automatically sent an e-mail to anyone who posted a property for rent on Craigslist, even if that person had specified that he did not want to receive unsolicited messages. (Location 1531)

Tags: marketing hack, airbnb

All these e-mails were identical except for the city, and they typically emanated from a Gmail account bearing a female name. (Location 1535)

Tags: email

“Reposting your listing from Airbnb to Craigslist increases your earnings by $500 a month on average,” the site informed prospective hosts. “By reposting your listing to Craigslist, you’ll get the benefit of more demand, while still being able to use Airbnb to manage and moderate your inquiries.” (Location 1552)

Tags: growth hacking, airbnb

always joked my job was safe because no one else wanted it,” she says. “The drivers hate you because their wife doesn’t love them and their children are ugly and it’s all your fault. The taxi-fleet managers don’t like you because they aren’t making any money. And any regulation is too much regulation.” (Location 1677)

Tags: funny

Uber was turning out to be a company rooted in complex math. Its biggest challenge, and where he found himself already frustrated with the performance of the startup, was finding ways to attract more drivers during peak times and to route cars into the areas of highest demand. (Location 1866)

Tags: uber

On a tech podcast, he added that the fight with the MTA recalled all the litigation and conflict of his decade in the world of peer-to-peer technology. “The great thing is I’ve seen this before,” he said. “I thought, Oh, man, I have a playbook for this. Let’s do this thing. When that happened, it felt like a homecoming.” (Location 1894)

Tags: playbook

Despite this optimism, Jordan and his partners identified four risks to their investment: Safety: What would happen if a guest trashed a home or apartment? International competition: Would overseas entrepreneurs clone the site? Regulation: Would cities allow hosts to continue to rent their homes without restrictions? Executive recruitment: Chesky, Gebbia, and Blecharczyk were running the company as a triumvirate — a council of equals. It was an arrangement that couldn’t last. Could they find new executives they trusted? (Location 2030)

Samwer gave the founders a tour. On many PCs they saw both the Wimdu and Airbnb websites in adjacent web browsers. “This is what we do,” he told them unapologetically. “You Americans innovate. Me and my army of ants, we go fast and build great operations.” He also told them that Wimdu had raised $90 million from Rocket Internet and other European venture capital firms and was already nine times larger than Airbnb in Germany. (Location 2104)

Tags: copycats

“They just want to see you suffer,” Graham told them in his kitchen. “They want an ounce of blood. Just fall on the sword, accept responsibility, and everyone will move on.” (Location 2185)

Tags: responsibility

Airbnb furnished each new manager with a set of online tools to monitor the health of the business and with something Chesky called an “office in a box.” It contained a guidebook to setting up an Airbnb-like working environment and included various props, like a portable Ping-Pong table and the books Delivering Happiness by Zappos founder Tony Hsieh and Oh, the Places You’ll Go by Dr. Seuss. (Location 2261)

Tags: playbook

“The worst thing you can do to a cloner is to let him keep his baby,” Chesky joked to Oliver Jung. “The cloner doesn’t want his baby. They build the baby to get rid of it.” (Location 2282)

Tags: copycats

“This is when I became CEO in a meaningful way,” he told me years later. “I changed my style. I hope jerk isn’t the first word they use. But 2011 was the year I really had to become a CEO, to become a champion of Airbnb, to get people to want to believe in it, to raise money, and to get us out of a true crisis. We came out of EJ and the Samwers stronger than when we came into it.” (Location 2296)

Tags: ceo

Kochman remembers something else his boss said on the ride back from the ETG meeting. Kalanick was talking with awe and envy about Jack Dorsey, who was fired from Twitter in 2008 but had recently reemerged with a more refined image at the payments firm Square. Success on the internet, it seemed, could be a platform for personal reinvention — a way to rid oneself of all the baggage of the past. “I remember on that car ride, Travis was explaining to me that Jack was a very different person early on in his career,” Kochman says. “After Twitter, he went away, he disappeared off the map and self-reflected. And then he came back as a completely different person. (Location 2382)

Geidt and Graves 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. (Location 2434)

Tags: growth hacking, playbook

Along with Kalanick and Graves, Geidt pioneered other aspects of the model and recorded it all in an online Google document to serve as a manual for Uber’s entrance into new cities. Drivers should be solicited by combing through limo-fleet listings in Yelp, the online directory, or by visiting airport-limo waiting lots. A launch party should bring together local media and tech luminaries, while a local celebrity should be selected as the first rider in the city and promoted in a blog post. (Location 2442)

Tags: growth hacking

They also used strategies to attract both drivers and riders, like offering subsidies and credits, and took some basic but important steps, like opening an Uber Twitter account in each city. The Google doc would become a company bible; employees took to calling it “the playbook.” Seattle, says Geidt, “became the first iteration of our playbook.” (Location 2446)

Tags: playbook

“Nobody loves a regulator. We got rules, we got regulations, we got laws.” (Location 2756)

“The luxury of Uber is about time and convenience. It’s not about the car.” (Location 2797)

Tags: remove friction, favorite

reception, he framed Uber Taxi as coming from a wing of the still-tiny startup, an entirely fictitious department that he dubbed Uber Garage.9 “Google has Google X, and we have the Uber Garage,” Kalanick told me that year. “If we have an idea we don’t like, we put it in the parking lot.” (Location 2805)

Both entrepreneurs politely defined their differences. Hailo was linking the existing supply of licensed taxis, trying to make cabbies more productive by filling in the margins of their day. Uber (aside from the Uber Taxi experiment) was trying to build an entirely new network of professional drivers with luxury vehicles. Hailo drivers could swerve to the side of the road to pick up passengers hailing them from the street; Uber drivers, legally, couldn’t. (Location 2814)

A new tactic was then added to the playbook: when traditional advocacy failed, Uber could mobilize its user base and direct their passion toward elected officials. (Location 2950)

Tags: playbook

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. (Location 2956)

Kennedy plopped into a chair and listened. After Hallisey left, she started talking into Peevey’s ear and didn’t stop for weeks. “This is a monumental shift and a brand-new industry,” she told him. “This is the cradle and you will either be the guy who was standing in its way and crushed an industry or the guy who facilitated a whole new world.” (Location 3061)

Tags: favorite

she suggested there was an aura of inevitability around the ridesharing services, linking them to organized carpooling across the Bay Bridge and arguing that “you can’t put the genie back in the bottle.” (Location 3074)

Tags: quotes

“I look at entrepreneurism as risk arbitrage. You are basically looking at risk and saying, ‘I think people are misunderstanding it and I’m going to go after it.’ (Location 3170)

Tags: entrepreneurial

Reflecting on the years 2011 through 2013, a person might find it difficult to conclude that one company was the more ethical operator. Uber started rampaging over local transportation laws when it appeared competitors might capture strategic ground. Chesky knew that Airbnb violated the strict housing regulations of New York City and elsewhere but pushed ahead anyway, and the site neglected to stop its own users from breaking the law. Both CEOs seized the tremendous opportunities before them with steely determination, pausing just long enough to turn around and repair some of the carnage they left in their wake. (Location 3588)

Uber had discovered what startup gurus like to call the virtuous circle, the links between various parts of its business. Lower prices led to more customers and more frequent usage, which led to a larger supply of cars and busier drivers, which enabled Uber to further cut prices and put more pressure on competitors. Even (Location 3766)

Tags: virtuous circle

“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. “The second thing is you need to be willing to partner with cities and tell your story. We found the most important thing to do is to go and meet city officials. 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.” (Location 4230)

Back in the spring of 2012, news of the funding and imminent expansion of the British taxi-hailing service Hailo flooded the tech blogs. As we have seen, Hailo’s premature announcement pushed Kalanick to quickly add vehicle choices to the Uber luxury-car app. Hailo was forced to retreat from the United States and return to its niche facilitating taxi rides in England and Ireland. In 2016, it was acquired by Daimler. (Location 4547)

Customer obsession (Start with what is best for the customer.) Make magic (Seek breakthroughs that will stand the test of time.) Big bold bets (Take risks and plant seeds that are five to ten years out.) Inside out (Find the gap between popular perception and reality.) Champion’s mind-set (Put everything you have on the field to overcome adversity and get Uber over the finish line.) Optimistic leadership (Be inspiring.) Superpumped (Ryan Graves’s original Twitter proclamation after Kalanick replaced him as CEO; the world is a puzzle to be solved with enthusiasm.) Be an owner, not a renter (Revolutions are won by true believers.) Meritocracy and toe-stepping (The best idea always wins. Don’t sacrifice truth for social cohesion and don’t hesitate to challenge the boss.) Let builders build (People must be empowered to build things.) Always be hustlin’ (Get more done with less, working longer, harder, and smarter, not just two out of three.) Celebrate cities (Everything we do is to make cities better.) Be yourself (Each of us should be authentic.) Principled confrontation (Sometimes the world and its institutions need to change in order for the future to be ushered in.) Kalanick showed (Location 4802)

Gang says Didi contemplated expanding into the States. Instead, in September 2015, it invested $100 million in Lyft. Then it established an anti-Uber ridesharing confederacy with Lyft and the regional ridesharing startups Ola, in India, and Grab Taxi, in Southeast Asia, all of them agreeing to share technology and integrate with one another’s apps. According to Gang, it was less about undermining Uber than about gaining negotiating leverage. “The purpose of them grabbing a lock of our hair and us grabbing their beard isn’t really to kill the other person,” he says. “Everyone is just trying to win a right to negotiate in the future.” (Location 4897)

Both Travis Kalanick and Brian Chesky had made big promises: to eliminate traffic, improve the livability of our cities, and give people more time and more authentic experiences. (Location 5039)