Airbnb
Paul Graham’s essay Airbnb documents a remarkable email exchange from early 2009 showing how Graham convinced Fred Wilson to consider investing.
Graham’s Core Position
Airbnb had massive potential despite skepticism. The marketplace model could eventually rival eBay, comparing it to “practically every really big startup” that transforms its original concept.
Main Selling Points
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Team Quality: The founders’ exceptional execution—they were actively “on the ground in NYC hunting down…their users”
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Counter-Cyclical Appeal: During recession, users needed rental income “to pay their rents”
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Market Expansion Potential: The platform would expand from sofas to professional operators
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Efficiency: “Very capital efficient,” allowing investor money to stretch further
Wilson’s Skepticism
Wilson remained cautious, doubting whether Airbnb could penetrate the hotel market, though acknowledging “a pretty big opportunity.”
My Takeaway
This exchange illustrates how founder advocacy sometimes matters more than initial market viability metrics.
How do you evaluate early-stage startups? I’d love to hear at persdre@gmail.com.