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Chronicles

The story behind the story

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As the coronavirus pandemic threatens to unravel Airbnb's business, some question whether CEO Brian Chesky can shift focus from new pursuits to preserving cash

The founder of the travel rental site has spent more than a decade building the company into one of the world's most influential startups. Tweets: @mdudas , @amir , @davidsacks , @coryweinberg , @alexeheath , @coryweinberg , @eliotwb , @suhail , @amir , @coryweinberg , @coryweinberg , @coryweinberg , @coryweinberg , @coryweinberg , @coryweinberg , @coryweinberg , and @coryweinberg Tweets: @mdudas : Not every person is cut out to be a “wartime CEO” - not a comment on Chesky specifically, but it's a big shift in mental model. Lots of VC advice to founders that it's time to go “wartime,” less discussion of whether they're specifically cut out for it. https://www.theinformation.com/ ... Amir Efrati / @amir : Last last year [Airbnb's] board of directors told CEO @bchesky to be more disciplined on cutting certain costs. Now pressure mounting internally (for employee stock liquidity & better managers) and externally (cratered sales). https://www.theinformation.com/ ... by @coryweinberg David Sacks / @davidsacks : 5/ Yes, Brian can save Airbnb and you can save your startup. You were a seed or series A-C company at one point; you can go back to an earlier stage and operate that way again. The rebuild will be painful but you can survive. https://www.theinformation.com/ ... Cory Weinberg / @coryweinberg : Brian Chesky regularly talks to Barack Obama, thinks travel can snap back quickly & gets help from an ex Steve Jobs' right hand. But some question whether the designer CEO can shift focus from new pursuits to preserving cash. Latest on the Airbnb saga: http://thein.fo/... Alex Heath / @alexeheath : “Airbnb is in discussions with investors to borrow an additional $750 million to $1 billion at an effective interest rate of about 10%” https://twitter.com/... Cory Weinberg / @coryweinberg : Some measure of the damage: # of Airbnb reservations down 85% in the first week of April compared with the same period last year, according to a sample of half a million properties analyzed by Transparent (FWIW company is seeing a boost in 28-days-or-longer rentals) Eliot Brown / @eliotwb : Hope springs eternal: “Some inside the company, as well as investors, still believe Experiences eventually could live up to Chesky's expectations.” https://www.theinformation.com/ ... @suhail : If the new narrative is to takedown Airbnb while it's in a tough spot, this is a losing narrative. @bchesky is a wartime, peacetime, and now *pandemic-time* CEO. Born in the 2008 crisis, it'll overcome this. https://twitter.com/... Amir Efrati / @amir : “Chesky has already become rich from Airbnb. Each of the co-founders cashed out about $75M in the co.'s early days.... [E]mployees say they are conscious of the wealth gap between them and the founders.” https://twitter.com/... Cory Weinberg / @coryweinberg : Chesky also relies on a stream of outside advisers who become very influential inside Airbnb. The latest was Hiroki Asai, the former creative director of Apple, who worked closely with the late Steve Jobs. Asai advised Chesky on Airbnb's marketing and design strategy. Cory Weinberg / @coryweinberg : Obviously every travel company is struggling from the pandemic. But this is coming after years the company struggling to meet insanely high expectations. ABB told investors and bankers that it could go public in 2019 at a $46B valuation, with $6B in annual revenue. Cory Weinberg / @coryweinberg : Board members are sticking with Chesky. The story features on-the-record quotes from a16z's Jeff Jordan calling Chesky a “wartime CEO.” And then there's this: https://twitter.com/... Cory Weinberg / @coryweinberg : New details on Experiences: - less than $35 million in revenue in 2019, short of an early-year goal to hit upward of $40 million. A few years ago, execs believed it could be bringing in hundreds of millions of dollars in revenue by 2019 Cory Weinberg / @coryweinberg : After raising $1bn in debt w/ warrants from PE investors, Airbnb is trying to raise at least $750-1Bn more. This first lien debt with would have an effective interest rate of about 10%. Cory Weinberg / @coryweinberg : What does it do about expiring RSUs? And when's the IPO? Would create lots of turmoil if Airbnb doesn't solve this issue. https://twitter.com/... Cory Weinberg / @coryweinberg : Some have questioned whether Chesky relied too heavily on loyal insiders when making appointments to top posts. Employees complained about ex-Experiences VP Joe Zadeh, an early Airbnb employee close to Chesky. He often talked down to employees and yelled in meetings Cory Weinberg / @coryweinberg : I talked to more than 20 people close to the company for this piece. Some questions whether Chesky's leadership include past reluctance to walk away from struggling money-losing initiatives, and an unwillingness to remove ineffective or problematic executives.

The Information Cory Weinberg

Discussion

  • @mdudas @mdudas on x
    Not every person is cut out to be a “wartime CEO” - not a comment on Chesky specifically, but it's a big shift in mental model. Lots of VC advice to founders that it's time to go “wartime,” less discussion of whether they're specifically cut out for it. https://www.theinformation…
  • @amir Amir Efrati on x
    Last last year [Airbnb's] board of directors told CEO @bchesky to be more disciplined on cutting certain costs. Now pressure mounting internally (for employee stock liquidity & better managers) and externally (cratered sales). https://www.theinformation.com/ ... by @coryweinberg
  • @davidsacks David Sacks on x
    5/ Yes, Brian can save Airbnb and you can save your startup. You were a seed or series A-C company at one point; you can go back to an earlier stage and operate that way again. The rebuild will be painful but you can survive. https://www.theinformation.com/ ...
  • @coryweinberg Cory Weinberg on x
    Brian Chesky regularly talks to Barack Obama, thinks travel can snap back quickly & gets help from an ex Steve Jobs' right hand. But some question whether the designer CEO can shift focus from new pursuits to preserving cash. Latest on the Airbnb saga: http://thein.fo/...
  • @alexeheath Alex Heath on x
    “Airbnb is in discussions with investors to borrow an additional $750 million to $1 billion at an effective interest rate of about 10%” https://twitter.com/...
  • @coryweinberg Cory Weinberg on x
    Some measure of the damage: # of Airbnb reservations down 85% in the first week of April compared with the same period last year, according to a sample of half a million properties analyzed by Transparent (FWIW company is seeing a boost in 28-days-or-longer rentals)
  • @eliotwb Eliot Brown on x
    Hope springs eternal: “Some inside the company, as well as investors, still believe Experiences eventually could live up to Chesky's expectations.” https://www.theinformation.com/ ...
  • @suhail @suhail on x
    If the new narrative is to takedown Airbnb while it's in a tough spot, this is a losing narrative. @bchesky is a wartime, peacetime, and now *pandemic-time* CEO. Born in the 2008 crisis, it'll overcome this. https://twitter.com/...
  • @amir Amir Efrati on x
    “Chesky has already become rich from Airbnb. Each of the co-founders cashed out about $75M in the co.'s early days.... [E]mployees say they are conscious of the wealth gap between them and the founders.” https://twitter.com/...
  • @coryweinberg Cory Weinberg on x
    Chesky also relies on a stream of outside advisers who become very influential inside Airbnb. The latest was Hiroki Asai, the former creative director of Apple, who worked closely with the late Steve Jobs. Asai advised Chesky on Airbnb's marketing and design strategy.
  • @coryweinberg Cory Weinberg on x
    Obviously every travel company is struggling from the pandemic. But this is coming after years the company struggling to meet insanely high expectations. ABB told investors and bankers that it could go public in 2019 at a $46B valuation, with $6B in annual revenue.
  • @coryweinberg Cory Weinberg on x
    Board members are sticking with Chesky. The story features on-the-record quotes from a16z's Jeff Jordan calling Chesky a “wartime CEO.” And then there's this: https://twitter.com/...
  • @coryweinberg Cory Weinberg on x
    New details on Experiences: - less than $35 million in revenue in 2019, short of an early-year goal to hit upward of $40 million. A few years ago, execs believed it could be bringing in hundreds of millions of dollars in revenue by 2019
  • @coryweinberg Cory Weinberg on x
    After raising $1bn in debt w/ warrants from PE investors, Airbnb is trying to raise at least $750-1Bn more. This first lien debt with would have an effective interest rate of about 10%.
  • @coryweinberg Cory Weinberg on x
    What does it do about expiring RSUs? And when's the IPO? Would create lots of turmoil if Airbnb doesn't solve this issue. https://twitter.com/...
  • @coryweinberg Cory Weinberg on x
    Some have questioned whether Chesky relied too heavily on loyal insiders when making appointments to top posts. Employees complained about ex-Experiences VP Joe Zadeh, an early Airbnb employee close to Chesky. He often talked down to employees and yelled in meetings
  • @coryweinberg Cory Weinberg on x
    I talked to more than 20 people close to the company for this piece. Some questions whether Chesky's leadership include past reluctance to walk away from struggling money-losing initiatives, and an unwillingness to remove ineffective or problematic executives.