Book Summary | The Upstarts: Uber, Airbnb, and the Battle for the New Silicon Valley

In The Upstarts: Uber, Airbnb, and the Battle for the New Silicon Valley, Brad Stone chronicles the rise of the two new powerhouses of new Silicon Valley – Uber and Airbnb. The book is nicely organized into three sections:
1. Side Projects, on how they built the foundations
2. Empire Building, providing insights into the challenges they faced and incredible growth they’ve achieved
3. The Trial of the Upstarts,

Major Players (background of the founders) 
– in case you get to meet them one day

Brian Chesky:
Chesky is a natural leader, full of charisma and confidence. He was selected by his classmates to give the commencement address in 2004 at Rhode Island School Design. After graduation, he worked as an industrial designer for various industries and even created a design firm called Brian Cheksy Inc, but he found all of it “pointless and uninspired and that it wouldn’t lead to the promised life that he’d found so seductive at RISD, or in the movie Pirates of Silicon Valley” (24). Joe Gebbia recalled, “I saw this gift he has, to be able to get people excited. I would have felt incomplete if I didn’t express to him what I was feeling” (22). He stepped up as the CEO of Airbnb in 2011; before that, Airbnb had a less efficient triumvirate system that all decision needed to pursue unanimity among all founders.

Joe Gebbia:
Gebbia also graduated from RISD with a degree in Industrial Design. During his freshman year at college, he “designed a colorful foam cushion with a handle and the imprint of a rear end” (24) for students to sit comfortably during a marathon review. After graduation, he utilized proceeds from a RISD design award to manufacture eight hundred units of his cushions – CritBuns, but only “sold a few batches” (25). He ended up working for a publisher in San Francisco designing books and gift packaging. On September 22, 2007, with the World Design Congress coming to San Francisco and the city’s hotels either over booked or overpriced, Gebbia sent Chesky an email suggesting “a way to make a few bucks” by “turning our place into a designer’s bed and breakfast” (26). Airbnb is a shorthand for Air Bed and Breakfast website that they put together using the free tools on WordPress (!!).

Nathan Blecharczyk:
Throughout high school and into college, “Blecharczyk wrote customized tools for a nascent industry: e-mail marketing” (97) , also known as something else: spam. The spam operation earned Blecharczyk close to a million dollars, and paid his college tuition at Harvard University. He eventually shut his business down in 2002 before the Federal CAN-SPAM Act, that made sending spam a federal crime, were passed in 2003. ” ‘All this was new,’ Blecharczyk says. ‘There were frankly no rules around it. It’s not just exciting to build things but to explore new fields. (…) That’s very true today and it has been true of Airbnb. It’s whole new concept, around which there haven’t been many rules’ ” (99). As a skilled programer, he later helped Airbnb gain initial growth by “a mechanism that automatically sent an-emil to anyone who posted a property for rent on Craigslist” (100) and allowed users to post Airbnb listings “to Craigslist with a single click” (101).

Garrett Camp:
The founder and CEO of StumbleUpon (a site for users to share and find interesting things on the internet without having to search for them on Google), Garrett Camp sold the internet startup to eBay in 2007 for $75 million, “turning it into one of the early successes of what became known as Web 2.0” (41). Enjoyed San Francisco’s nightlife but frustrated by its taxi system, he brainstormed for a way to summon cabs and town cars using smartphones. He found some inspirations from the a scene in the movie Casino Royale: “the image of a graphical icon of Mondeo moving on a map toward his destination stuck in his head” (40), and that is the early form of Uber. “In the estimation of founder Garrett Camp, the name stood for something classy, upscale and pricey – stepping out of a black BMW to meet your friends outside a nightclub was so über” (185). Travis Kalanick thought otherwise and recalled, “Garrett brought the classy and I brought the efficiency” (52).

Travis Kalanick:
Kalanick just sold a previous startup, “the streaming-video company Red Swoosh for $15 million, to a much larger competitor, Akamai, and was in the middle of what he later called his ‘burnout phrase’ “(49) traveling around the world and angel investing. While Camp was talking endlessly about Uber, Kalanick had his own startup idea which “was ironic: he was envisioning a Airbnb-like system that would operate a global network of luxurious lodgings that could be leased via the internet” (50). Kalanick viewed himself as an investor and advisor to Uber until he succeeded Ryan Graves as CEO in 2010. He brought along connections and venture capitalists on board, as well as a “hustle-orientated” culture to Uber. Kalanich goes by the motto: “fear is the disease, hustle is the antidote” (130).

Travis Kalanick (left) and Brian Chesky (right) being interviewed at TechCrunch Disrupt

3 thoughts on “Book Summary | The Upstarts: Uber, Airbnb, and the Battle for the New Silicon Valley

  1. I found the different paths that the leaders took very interesting. In particular, I found it very interesting that Nathan Blecharczyk made so much money from spam and used it to pay his college tuition. That reminds me of a speaker that we had last year who said he won lots of money by playing online poker and then converted this energy into being a successful entrepreneur. I would like to hear more about the trial of the upstarts and how the process went. I’m assuming there were my difficulties, but I’m interested in hearing how they worked through those.


  2. I never got the chance to read this book last semester, so thank you for the great summary of the different people to know. We had discussed a few of them in class, but I agree with Maddie–the fact that Blecharcyzk was able to use spam profits to pay for college tuition is so fascinating. Thank you for educating me on these people–great job!


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