<prompt> Human: For example, if I want to sell 30,000 worth of stocks to my friend, then hell pay be 30,000. After tax thats going to be 20,000. What if I tell him he can buy me a car worth 27,000 for his stocks. Would this work out or are we both going to regret this.  <response>: Legally you have to report trading or bartering like this on your taxes. 