His first professional efforts centered on the packaging, promotion and supply of sports and industrial films. Working jointly along with his wife in their Cleveland house, Dolan edited and created short film reels of sports events for syndication to television stations. Selling the company, Dolan joined the acquiring company and went east to The Big Apple. In the early 1960s, Dolan created Teleguide Inc., which supplied advice services via cable to New York City resorts. The exact same decade, he founded Sterling Manhattan Cable, the very first urban cable television business in the state. In its early years, Sterling invented first-of-its-type arrangements to bring New York professional sports teams, cultural programming and films to the houses of Nyc cable audience. In the early 1970s, Dolan founded Home Box Office Inc., the first premium scheduling service in the cable television business. He coordinated Cablevision Systems Corporation on Long Island subsequent to the sale of Home Box Office to Time-Life, Inc. and has spearheaded many of the firm’s progress. Most recently, he was the vision behind VOOM, Cablevision’s attempt to enlarge content delivery and satisfy the demands of the bursting HDTV marketplace, that was anticipated to contain 6 million homes by the end of 2003 — and 12 million by year end 2005. Dolan is a trustee of Fairfield University as well as an associate of the board of governors of St. Francis Hospital in Port Washington, New York.