According to Miles Smith's doctoral thesis, "Richard developed a cheery disposition and seems to have been a generally happy and content child". Richard lived on the family plantation until he was 16. In 1796, he was sent briefly to a local grammar school, and then attended Transylvania University, the first college west of the Appalachian Mountains. While at the Lexington college, where his father was a trustee, he read law as a legal apprentice with George Nicholas and James Brown, later a US Senator.