He graduated from Culver Military Academy in 1962 and received the institution's "Man of the Year" Award in 1998.
[2] While at Bear Stearns, Roberts, alongside Kohlberg and Kravis, began a series of what they described as "bootstrap" investments.
In the following years the three Bear Stearns bankers would complete a series of buyouts including Stern Metals (1965), Incom (a division of Rockwood International, 1971), Cobblers Industries (1971), and Boren Clay (1973) as well as Thompson Wire, Eagle Motors and Barrows through their investment in Stern Metals.
Most notably, Bear Stearns executive Cy Lewis had rejected repeated proposals to form a dedicated investment fund within Bear Stearns and Lewis took exception to the amount of time spent on outside activities.
[14] Roberts is the founder and chairman of the boards of directors of non-profit organizations such as the Roberts Enterprise Development Fund (REDF), which focuses on job creation for people facing significant barriers to work.