Gary was accepted into both Stanford University and Harvard on the merit of his hard work, but ended up rejecting both schools. Gary graduated from Rice University with an AB in communications and later from Harvard Law School. 
Fresh out of Harvard, Hailey got a job as an attorney with the Federal Trade Commission, spending 13 years there. He then became a general counsel at National Media Corp/Quantum Television. Not long afterwards Hailey became partner at Venable LLP where he spent nearly 24 years honing his legal experience before retiring in 2017. Since then, Gary has acted as an advertising/marketing attorney at his own practice in Washington, D.C. 
Gary has a popular music blog called "2 or 3 Lines" which has received more than a million page views. He has written about over 1,500 songs for the blog and will soon be entering the podcast world alongside his TV-star son Peter's "Redskins Talk" podcast.