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Why we picked it This is the real founder story behind the meme: Chesky and his cofounder flew to New York and knocked on hosts' doors, then rented a camera and shot listing photos themselves because the photos were killing bookings. Crucially he names the exit line, do it by hand until it hurts, then hand it off, so you hear an actual founder deciding when manual work has run its course. That is the tension in the question, told as a story.
Airbnb's Brian Chesky in Handcrafted (Masters of Scale)
On Masters of Scale by Reid Hoffman (host), with Brian Chesky
- "Do things by hand until it is painful, then automate" is a usable rule for the exact line the question is asking about.
- The door to door photo work was not busywork, it taught Airbnb what hosts and guests actually valued, which is why they did it before automating.
- Manual effort earns its keep when it surfaces learning you could not get any other way, once it is just repetition, it is time to switch.