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The Upstarts by Brad Stone.
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1-Page Summary 1-Page Book Summary of The Upstarts

Read the full summary for the full timelines of each company. Here we’ll discuss the high-level commonalities between both companies.

Both started as side projects, looking for the next big idea.

At Uber, Camp and Kalanick had both recently had their companies acquired. Camp was still busy at StumbleUpon, while Kalanick was enjoying his time away. From incorporation, over a year passed before they hired a CEO and invested real time.

At Airbnb, Chesky and Gebbia started it as a way to pay rent. It’s months before they really pick it as their main idea.

Both were rejected early on with a failure of imagination.

Uber’s potential investors often questioned the size of the black car market, not predicting how it could actually grow to the taxi market and even bigger. Others knew Uber was going to run into hostile local transportation laws. Others were worried about how uninvolved the founders were.

Airbnb investors were concerned about the size of the market, designer founders who didn’t fit the Silicon Valley engineer-founder mold, the legal liability of injured guests or destroyed homes, and concerns about whether anyone really wanted to sleep in strangers’ homes.

  • Instead, with a more ambitious imagination, Airbnb can be defined as the larger “eBay, but for spaces,” or “the largest hotel chain in the world, without actually owning inventory” or “transforming a massive illiquid asset - space - into a peer-to-peer marketplace.”

Both grew virally, exhibited network effects, and kicked off powerful flywheels.

Uber had natural local virality - back then if you stepped out of a black car in front...

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The Upstarts Summary Shortform Introduction

The Upstarts alternates chapters between Uber and Airbnb and moves chronologically through time. To simplify the story, we created separate timelines for each company. We then created an exclusive chapter, discussing commonalities between both companies.

While the many timeline entries can seem a bit tedious, the fun way to read...

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The Upstarts Summary Uber History

2007-2009: Uber Begins

May 2007: eBay acquires Garrett Camp’s StumbleUpon. He starts living large and running into frictions with taxis in SF. He tries workarounds like calling multiple dispatchers at once, keeping a rolodex of gypsy cabs, and renting town cars for the entire night. He becomes enamored with a scene from a Bond film where Bond tracks a car coming to him on a phone.

Summer 2008: Apple announces the iPhone and the app store.

August 2008: Camp registers ubercab.com

November 17, 2008: Camp registers UberCab as an LLC in California. He starts doing market research on cabs and chauffeured transportation. His original plan is to buy five Mercedes and share the cost with friends.

December 2008: Camp meets with engineer Oscar Salazar, friend from grad school, who signs as first engineer. Soon after, Camp meets with Travis Kalanick at LeWeb in Paris.

  • This is where Kalanick’s version of the origin story begins. In reality, Kalanick is only mildly interested at this time, having just sold his company Red Swoosh to Akamai and was drifting.
  • Kalanick argues that instead of centrally owning cars, UberCab should distribute the app to drivers who own their own...

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The Upstarts Summary Airbnb History

2007-2009: Airbnb Begins

Sept 2007: Brian Chesky is in Los Angeles, working at a design firm and making furniture on the side. Joe Gebbia is currently working at a book publisher and making CritBuns cushions on the side. Gebbia sends Chesky a cushion, and Chesky makes up his mind to live in SF. Strapped for cash, Chesky asks if he can rent the couch for $500/mo instead of paying for a bedroom. Gebbia declines, saying Chesky needs to pay for a full bedroom to make bills work.

Sept 22 2007: A design conference in SF is coming up. Gebbia sends Chesky an email proposing a “way to make a few bucks - turning our place into a designer’s bed and breakfast.”

Sept 25 2007: They launch airbedandbreakfast.com with wordpress, and circulate the site to city design blogs.

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Oct 2007: Amol Surve, is their first guest. The idea doesn’t immediately strike them as THE idea - they continue brainstorming ideas for new companies over the next three months.

March 2008: For South by Southwest, they launch a new version of the website, with Nathan Blecharczyk as engineer. They email anyone in Austin who...

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The Upstarts Summary Commonalities Between Uber & Airbnb

In this Shortform exclusive section, we discuss commonalities between Uber and Airbnb. Beyond their similarities in business model as two-sided marketplaces, they also faced similar pressures in early investor skepticism, government regulation, and frictions with drivers (suppliers and hosts).

Both started as side projects, looking for the next big idea.

At Uber, Camp and Kalanick had both recently had their companies acquired. Camp was still busy at StumbleUpon, while Kalanick was enjoying his time away. From incorporation, over a year passed before they hired a CEO and invested real time.

At Airbnb, Chesky and Gebbia started it as a way to pay rent. It’s months before they really pick it as their main idea.

Both were rejected early on with a failure of imagination.

Uber’s potential investors often questioned the size of the black car market, not predicting how it could actually grow to the taxi market and even bigger. Others knew Uber was going to run into hostile local transportation laws. Others were worried about how uninvolved the founders were.

Airbnb investors were concerned about the size of the market, designer founders who didn’t fit the Silicon...

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The Upstarts Summary Miscellaneous Notes

Travis Kalanick’s History

  • In high school, Kalanick sold Cutco knives and started an SAT training company after graduation.
  • In 1998 he dropped out of UCLA senior year to join classmates building Scour.net, a search engine for media files on local networks.
    • In 1999 Scour was getting 1.5 million views a day and 900k visitors in two months.
    • A few “nonlucky” events happened: Michael Ovitz dragged out an investment offer, sued them, and acquired 51% of the company; in 2000, Scour was sued for $250 billion and declared bankruptcy fall of 2000.
  • In 2001, Kalanick started Red Swoosh, a company offering to save bandwidth costs for media companies by P2P distribution.
    • Within a year his co-founder left, poached the engineers, and Travis was alone watching deals fall through.
    • In 2005, Mark Cuban invested $1MM, and Travis moved to the Valley.
    • In 2007, he sold the company to Akamai for $18.7MM, netting him several million after years of labor.
  • Kalanick wasn’t sure about joining Uber for over a year. He was...

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The Upstarts Summary Notable Quotes

“If you want to build a truly great company you have to ride a really big wave. And you’ve got to be able to look at market waves and technology waves in a different way than other folks and see it happening sooner.” - Greg McAdoo, Sequoia

“Everyone is going to give you advice. Ask for the story behind the advice. The story is always more interesting.” - Travis Kalanick

“Don’t worry about competitors; startups usually die of suicide, not homicide.” - Paul Graham.

Kalanick, after Scour went bankrupt: “I was playing the game I call ‘fake it till you make it.’ Basically fighting reality. When you do that too long, when you are in failure state, it will eventually crush you.”

“Bleeding Uber Blood” - Travis Kalanick, in company emails.

“This is what we do. You Americans innovate. Me and my army of ants, we go fast and build great operations.” - Oliver Samwer, head of Rocket Internet, in threat to AirBNB

“They just want to see you suffer. They want an ounce of blood. Just fall on the sword, accept responsibility, and everyone will move on.” - Paul Graham to Chesky, during EJ’s house ransacking ordeal.

“This is going to be the best deal of your life.” - Chesky to...

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Table of Contents

  • 1-Page Summary
  • Shortform Introduction
  • Uber History
  • Airbnb History
  • Commonalities Between Uber & Airbnb
  • Miscellaneous Notes
  • Notable Quotes