Bobby Mason grew up in South Central Los Angeles, where he lost three friends over the years to gunshot wounds.
When Mason reached high school, his parents facilitated his admittance to one of the top college prep schools in the country, The Harvard School (now known as Harvard-Westlake) in North Hollywood, California. While at the Harvard School, Mason was exposed to a diverse community of children from varying cultural and economic backgrounds and varying degrees of privilege. Mason declares he had experiences and made lifelong friendships with people that he otherwise would probably never have encountered or been exposed to. He honed his dream of being a scholar/athlete at the highest levels and was able to realize this when he was admitted to Amherst College in Massachusetts.
In 1996, Mason received his Bachelor of Arts degree cum laude in political science from Amherst, where he had also played baseball. He went on to attend Stanford Law School, graduated in 2000 and is currently an attorney in Los Angeles. He previously worked as an assistant to a sports agent and a consultant at a consulting firm.