The Upstarts by Brad Stone, published in 2017, is a narrative history of the two startups that defined the sharing economy: Uber and Airbnb. Stone, a longtime Bloomberg technology journalist and author of a well-known book on Amazon, follows both companies from their first days around 2008 and 2009 to their rise as global giants. The book reads like a business thriller and gives founders a close view of how fast growth works on the ground.
What is The Upstarts about?
Stone tells the two stories side by side. Airbnb begins with Brian Chesky, Joe Gebbia and Nathan Blecharczyk renting air mattresses in their San Francisco flat, selling novelty cereal boxes to stay afloat and enduring a long stretch when almost nobody used their site. Uber begins with Travis Kalanick and Garrett Camp wanting a better way to hail a black car, and grows into an aggressive expansion machine under Kalanick’s leadership.
The middle of the book covers how each company scaled: the tactics for winning cities one at a time, the fights with taxi lobbies and hotel groups, and the battles with copycat rivals in China, Europe and elsewhere. Stone contrasts the two leaders. Chesky comes across as an idealist who wants Airbnb to stand for belonging, while Kalanick is portrayed as combative and willing to break rules if it helps Uber win.
The book also places both companies within a wider shift in Silicon Valley, when smartphones, cheap capital and new attitudes towards sharing made these businesses possible. It ends with the companies at the height of their power, just before Uber’s internal crisis in 2017.
What are the main lessons for founders?
- Survive the long flat stretch. Airbnb spent many months with almost no growth. Surviving until you find what works counts for a lot, so keep costs low and keep talking to users.
- Do things by hand. The Airbnb founders visited hosts and photographed their homes themselves, which lifted bookings. Manual work in the early days teaches you what to automate later.
- Win one market at a time. Uber launched city by city with local teams and local playbooks. A tight focus lets a small company dominate before expanding.
- Plan for regulation early. Both companies grew into conflict with laws written for taxis and hotels. If your model touches regulated sectors, build relationships and a legal strategy before the fight arrives.
- Culture travels with growth. The habits founders set early, good or bad, spread to thousands of employees. Decide on your values before you scale.
Who should read The Upstarts?
Founders building two-sided marketplaces, mobility or travel products, and anyone whose business model clashes with existing rules. It is a gripping read for founders at any stage who want to understand how venture-backed hypergrowth looks from the inside.
Readers who want a practical how-to can skip it. The book is journalism, so the lessons are drawn from stories and you must apply them yourself.
How do you put The Upstarts to work this week?
- List every law or local rule your business touches and name the person or group most likely to object to your model.
- Do one task by hand that you plan to automate later, such as setting up a new customer in person, and write down what you learn.
- Write 3 values you want your company to keep as it grows, and share them with your team.
For a structured look at how other founders started and grew their companies, take the free Startup Life module in the F/MS Startup School.
Where does The Upstarts fall short?
The book went to press just before Uber’s crisis in 2017, when reports about its workplace culture led to Kalanick’s resignation as CEO. Readers have to look elsewhere for that part of the story. Stone also focuses on founders and investors, so drivers, hosts and neighbours affected by these platforms get less attention. The admiration for speed can make rule-breaking look like a smart strategy. For the economics of platforms behind both companies, read Modern Monopolies.