They're able to lose tens or even hundreds of millions of dollars a year providing completely unsustainable services, but they can't keep doing it forever. When they start monetizing, they have to use methods that are far more aggressive than would have been needed originally, because they're starting at the bottom of a giant hole they dug themselves into.
Yes, a store that sells dollar bills for 90 cents would be very popular. The tech industry needs to stop acting like there's anything impressive about that.