Roy Masters was born Reuben Obermeister in London in 1928 to a Jewish family of diamond cutters.

[citation needed] His family could only afford to pay for higher education for his older brother, so Masters did not attend college.

[2] He was sent to Brighton, England to apprentice in diamond cutting at his uncle's company, Monnickendam Ltd.[3] Masters was said in a newspaper article to have served in the Royal Sussex Regiment of the British Army during World War II; however, Masters himself never made this claim in any of his books or on any of his radio broadcasts.

He pursued his trade of diamond cutting in many places, including Amsterdam; Brussels; Belgium; and Johannesburg in 1947, where he spent two years.

In his early twenties, he traveled across America, giving lectures about the topic of diamond cutting in 40 different states.

[4][2] Masters met and married his wife Ann in Birmingham, Alabama, and they eventually moved to Houston, Texas.

During his early years in Brighton, Masters saw a stage hypnosis presentation in which the hypnotist easily induced volunteer subjects to do strange and outlandish things.

Masters remembered pondering the question: "Why can't hypnotism be used to make people act sensibly, rather than foolishly?

In 1961, Masters started a talk radio counseling show, which is currently broadcast with the title Advice Line, as a syndicated program.