The Upstarts By Brad Stone: Compelling. HIGHLY RECOMMEND


Brad Stone is a brilliant business writer. His newest book, The Upstarts, takes us behind the scenes of Silicon Valley businesses like Uber and Airbnb – how they came to be, the founders’ stories, who else is involved, what it took to get them off the ground, missteps, regulatory problems, what it means to disrupt the world as we know it (with an app).

  • It’s an absolute must-read – but feels like two distinctly different books (which may be a shortcoming)
  • The first half is about the founders and how they landed on these ideas.
  • The backstory of how these young startups are interconnected is fascinating
  • Great insights also on how a decade ago, wealthy VCs in their late 30 or 40’s, were unable to see the appeal or potential of the “sharing economy” and missed out on the first rounds of funding.
  • This first section of the book is incredibly inspiring and a fast read. In flipping through to check my notes, I was struck again by how powerful and riveting and entertaining this story is!
  • The second half is a bit more of a slog.
  • It covers the companies’ massive growth (doubling their users every few months) and drills down on the turmoil of dealing with regulators and competitors.
  • Plus the many self-inflicted legal/safety issues that for airbnb, in the particular, resulted from their Pollyannaish outlook. Reading how unprepared they were in anticipating all the many things that could go wrong when you let strangers into your home is mind-boggling.
  • The book, completed at the end of 2016, barely touches on all the issues that are currently challenging Uber and putting Kalanick ‘s leadership in question (company culture, sexual harassment lawsuits, lack of diversity, Trump meetings).


Key takeaways:

  • Travis Kalanick – For many, he has become persona non grata. Not for me. I think he’s a genius and one of my business idols. In 8 short years, he fundamentally changed how we approach transportation.
  • He’s a force of nature. Exactly the kind of scrappy, entrepreneurial, hardnosed leader every startup needs if it intends to succeed. Cut from the same cloth as many of the other founders I admire including Steven Jobs and Jeff Bezos.
  • Not that I am in his league, but having started several businesses myself I know what it takes to make it. It’s not about work-life balance, it’s about how driven you are – and how aggressively and single-mindedly you pursue your vision.
  • This is probably oversharing but I found him so relatable that I had to google his birthday: LEO!!

Read on below for 5 more takeaways on what it takes to create a successful start up:

Restless, inventive minds

  • Uber’s founders, Garrett Camp, and Travis Kalanick are both described  as being “Habitually restless, frustrated by inefficiencies and armed with a willingness to challenge authority.”
  • Camp and Kalanick also share an enthusiasm for coining new phrases and mining the potential for words:
    • Instead of mobile hitchhiking: ridesharing
    • Uber is no longer the anti-taxi, it’s now: transportation as reliable as running water, everywhere and for everyone
  • Paul Clanon, Executive Director of Calif Public Utilities Commission, on Travis: “The guy’s a jerk but I have to say I kind of have a soft spot for him. Maybe the way you build organizations as successful as Uber is by not giving a fuck what regulators think of you.”


Well-connected – so many of the tech people I follow on twitter, blogs, snapchat and medium, play a role in this book either as advisors, colleagues or VCs, including:

  • Tim Ferris (top business podcast, 4 Hour Work Week)
  • Justin Kan
  • Bill Gurley (VC)
  • Chris Sacca
  • Alfred Lin (ex-COO Zappos)
  • Michael Seibel (Y Combinator)
  • Paul Graham (VC/ Y Combinator)
  • Fred Wilson (VC)
  • The Jam Pad – Kalanick’s SF apt where entrepreneurs would gather to jam on new startup ideas. It was an entrepreneurial safe house, where like-minded obsessives could gather in front of a whiteboard and debate the intricacies of building internet companies.


Surfing Analogy for Start-Ups

  • The first time I heard this analogy was in The Third Wave by Steven Case (Case is from Hawaii so it made sense).
  • In The Upstarts, Greg McAdoo, VC at Sequoia Capital, is quoted as saying: “Being a great entrepreneur requires the precision of a great surfer. If you want to build a truly great company you have got to ride a really big wave.”


The Trough of Sorrow

  • This is the name Silicon Valley’s startup scientists have given to that phase of a company’s gestation when the novelty of a new business idea wears off and the founders are left trying to jump start an actual business.
  • Currently being used to describe what is happening at Snapchat.



  • Highest compliment to receive from a VC.
  • Means you are an unkillable startup e.g. “Wow you guys are like cockroaches, you just won’t die,” Paul Graham describing airbnb’s two founders
  • Closely associated with True Grit, another important attribute in the founders of the most successful startups including Google, Paypal and airbn.

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