$150M a year in losses. Sounds great! My parents generation, which maybe also has something to do with living in the midwest, has been using VRBO and it's affiliates longer than airbnb has existed outside of silicon valley, and are reluctant to change.
They're also the property owners right now, relative to the millennials.
$150M is a large number, but so is $1b. At that burn rate they have over six years of runway.
It may be that for every $100M they spend on acquisition, they make $200M over three years in sales, in which case it would make sense to burn cash now to capture the market. They could also be going all LivingSocial: setting money on fire with no path to unicorn profitability.
Anyway, no real way to know without the inside financials.
They're also the property owners right now, relative to the millennials.