The Upstarts by Brad Stone — review and summary

Brad Stone is a technology journalist best known for The Everything Store, his account of Amazon's rise. The Upstarts applies the same detailed narrative journalism to Uber and Airbnb — tracing both companies from founding through their first decade and the specific decisions and circumstances that shaped them.

The parallels and contrasts

Stone explicitly frames the book around the parallels between the two companies. Both were founded in the same period (2008-2009), both used the internet to connect providers and consumers in markets previously dominated by regulated incumbents (taxis, hotels), and both grew using tactics that occupied ambiguous legal territory.

The contrasts are as instructive as the parallels. Airbnb's culture was warmer and more publicly careful about legal compliance, while Uber's was more aggressive. Both were ultimately disruptive, but the specific style of disruption differed in ways that affected how regulatory fights played out and how each company was perceived.

The regulatory question

The most substantive section of the book for readers thinking about disruption and ethics covers the regulatory strategy of both companies. Both Uber and Airbnb faced incumbent industries that used regulatory frameworks to resist competition. Both chose, at various points, to operate in regulatory grey zones, accumulate users quickly, and use that user base as political leverage against regulatory opposition.

Stone presents this without hagiography. The tactics worked, in many cases. They also imposed real costs on specific people — cab drivers, hotel workers, residents of neighbourhoods overwhelmed by Airbnb inventory — who had reasonable claims on the regulatory protections being circumvented.

The founder accounts

Stone has good access to the founders of both companies. Travis Kalanick's portrait is unflattering in specific ways: technically capable, relentlessly aggressive, and not particularly interested in the people costs of his approach. Brian Chesky's portrait is more nuanced — someone who took longer to move fast but built something more durable in the process.

Who this book is for

The Upstarts is most useful for readers interested in the specific mechanics of how platform businesses were built in the 2010s, and in the regulatory and ethical questions that platform disruption raises.

Practical reflection prompts:

• What is the difference between disrupting a market and extracting from one? Where is that line in the companies you follow or work for?
• How do you think about the relationship between moving fast and the costs that speed imposes on others?

Bibliographic details

• Author: Brad Stone
• Published: 2017
• Publisher: Little, Brown and Company