The Upstarts by Brad Stone

Kit Teguh
4 min readJul 10, 2021

By this time, Uber and Airbnb (as well as Facebook, Amazon, Google, etc) have become staples of the Silicon Valley lore. This is probably the tale that business leaders from one generation will hand down to the next generation — how young, idealistic entrepreneurs carved their way into the accommodation and transportation market that has long since stagnated. Disruption is a cliché in the startup terminology, but it is for the pursuit of disruption that startups exist.

There are a multitude of books which rehashes the tales of these startups written from different angles. Airbnb and Uber rose like twin peaks at about the same time, their paths intermingling with each other. There are many parallels in terms of their beginnings, rise and controversies, all which Stone summarised more than adequately in the book. Stone had access to the teams and wrote with a largely unbiased account of the two companies, even getting through to controversial subjects.

There is no need to describe how Airbnb and Uber started — in many ways a lot of startups started as a side project of their owners. Airbnb and Uber were beneficiaries of the popularity of smartphones and apps, as well as GPS tech which can be integrated into these apps. They were at the right place and time to enjoy the wave. The meteoric rise of Airbnb and Uber are inevitable.

Others are not so lucky. I am reminded of reading the Innovators by Isaacson when innovation is inevitable because the time is truly ripe for it. Semiconductors are invented in two separate labs via two separate methods. At around about the same time Uber was finding its foothold, there were other companies such as Hailo, Taxi Magic, Cabulous, etc. which were doomed to failure.

Out of the list of failed companies, Couchsurfing hit home for me, as they were superseded by Airbnb pretty early on in Airbnb’s rise. Airbnb was all about its community of hosts and establishing real life connection between guests and hosts. Its motto “Belong anywhere” is a strong sell for its global brand. Couchsurfing has been around much longer but its owners have never really pushed to monetise the platform. This works really well, but it may not have been the most sustainable move, as Couchsurfing is pushed to the backwaters of failed startups even though I never saw it as one. Airbnb was able to provide a better looking, easier to use and logical platform for travelers who want a cheaper alternative to hotels. Having said that, Couchsurfing is still around and it still has a special place for travelers despite its lack of success and its 180 turn around from a non-profit to a for-profit company.

Uber managed to navigate through the complexity of the ridesharing industry as they were best to take advantage of the inefficient taxi market and turn its on its head by providing an alternative black car service. In the beginning Uber was a premium brand and offer services beyond the market price of taxis, but at least the riders know what they’re getting. Eventually they brought about taxi companies and anybody who wanted to be an Uber driver into the market as they faced more pressure from the competition, Lyft. Their rise is not without battle scars and pissing people off, headed by its controversial (then) CEO Travis Kalanick who was combative to anybody who’d come on his way.

Airbnb’s competitive landscape is more varied, with the competition coming from hotel and hostel websites, aggregators and even Craigslist, which they used to leverage their own platform. They were able to leverage the tech, with the brains of their first engineer Nathan Blecharczyk who were one of the first pioneers of automated email marketing, as well as ballsy operational moves which put the hosts at risk as they fall into legal squabbles, especially in New York. Like Uber, Airbnb rode through their early pains not without battle scars and a host of unhappy city councils who struggled to regulate them.

Disruption then. The first third of the book accounts for these growing pains, chronicling its early beginnings to the point of their ascent. The latter part of the book is also a chronicle of the two companies’ battles with their customers, regulators and even themselves. Although some of it is fascinating reading, eventually it became a list of legal battles which dragged the book down a little.

These stories are still stories worth retelling, though unicorn companies only come rarely as unicorns in Narnia themselves because there are parts of the book which are instructive. For example, when Garrett Camp listed down questions to familiarise himself with the transportation market he sought for the competitive profiles of other on-demand car services, the average pickup time (in minutes) for someone to call a taxi, and also questions the technical requirements for a dispatch software. For each of these tasks he assigned a number of hours of research.

If you are already working in startups you may have already known the history of these companies to a tee. It is useful to read book about the success of other startups even though there are many variables to any business. Stone managed to show us that conflict was an essential part to the success of Airbnb and Uber. Other companies who stifled suffered from excess civility. Businesses are run with heart, but balls take them to the next level.

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Kit Teguh

A full time project manager who loves to read on the side. Connect with me to chat anything tech and lit.