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Review: The Upstarts

The Upstarts: How Uber, Airbnb, and the Killer Companies of the New Silicon Valley are Changing the World is a journalist’s take on how Uber and Airbnb came to exist. These two startups are two of the biggest in history, and their stories are intertwined in how their business models1 are upending established industries. Both companies have spawned countless Uber/Airbnb for X startup ideas in their wake. And worse, their enormous success has provided a playbook for those who see regulations as businesses disincentives and are willing to aggressively disregard the rules to create and/or muscle their way into a market.

The stories that the book collects on the founding and growth of these two post-Facebook mega-startups isn’t all that exclusive. This is partially due to how recent the events are; they are two of the biggest startups in tech and are topics of Silicon Valley discussions on a daily basis. Moreover, they’re built on existing business models, competing against existing powerful incumbent industries, popularizing a class of on-demand worker that some fear is the next step in corporations trying to squeeze their labor costs. That is, AirBnb and Uber have both courted plenty of news-worthy controversy, and the book presents a chronology of their histories that mirror any tech news site.

That said, I do applaud the author for making the extra effort to dig into the founding stories and dispel the myths.

My personal reaction to reading The Upstarts is affected by my proximity to the principal characters of the stories told. I started working at Square in the summer of 2011: it was about this time that AirBnb, Uber and Square all began to take off in earnest. While Square proved to be not quite at the same level in terms of market cap—despite making it as a public company—we felt like we were in the same “class” of startup, with similar trajectories in business growth, headcount, cultural maturity, etc. Uber would eventually move to the same building, taking a few floors below Square’s leased floors2, while AirBnb had their new offices within a 10-minute walking distance.

I also happened to interview at both companies, and knew engineers who worked there as well. On the ground, the comings and goings of these companies are much less dramatic than portrayed in the book; the engineering teams I talked to seemed just like any other growing organization, with similar problems around management and scaling systems and maintaining legacy platforms. Granted, it may be a similar deal to Chaos Monkeys, where the low levels of the organization don’t engage in nearly as much politics and drama as that of high-level management. Then again, I had my suspicions about Hatching Twitter‘s liberal embellishment as well, and it probably just takes some amount of based-on-a-true-story tension to keep readers interested.

Here’s hoping someone is working on an article on the genesis of Square, just so I can make direct comparisons from experience to journalism.


  1. Bringing the so-called sharing economy to the forefront of discussion and technological trends.

  2. It was awkward, the few times we saw former colleagues that Uber poached from Square, step into the same elevator and get off on an earlier floor.

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