Asymmetrical information is one reason why markets fail. It is when the seller knows more than the buyer. Geroge Akerlof won the Nobel prize in Economics in 2001 for writing "The Market for Lemons". He asks the question, if someone wants to sell me a second-hand car, do I really want to buy it.
The Undercover Economist explains it well:
Why you can never buy a decent used car. - By Tim Harford - Slate Magazine
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