[3][4][5] He served in the United States Army Air Forces at the end of World War II[6] and studied at John Carroll University, before dropping out and entering the telecommunications field.

[4] Dolan's earliest professional endeavors focused on the packaging, marketing, and distribution of sports and industrial films, which he produced with his wife in their Cleveland home and then sold to televisions stations which syndicated the material.

[7] Dolan sold his interests to Telenews in exchange for a job,[6] and when he was 26 years old, he moved to New York City and founded Teleguide Inc, a service that provided information to hotels.

[8] In the early 1970s, Dolan founded Home Box Office, the first premium programming service in the cable television industry, which he sold to Time Life.

He submitted a maximum bid of $750 million,[13] but ultimately lost out to a group headed by John Henry, Tom Werner, and Larry Lucchino.