After the great war, Shirley went back to song plugging, but says he got tired of it. He never got tired of New York City and the Broadway crowd however (athletes, journalists, theater, music people and the first nighters who followed them) He would spend his entire life living there and hanging out with them. They obviously served him well too as a great source of contacts that he would capitalize on in the years to come.
As a career change in the early 1920's, he first tried his hand at bond sales. This probably awakened him to just how much money is really out there in the world. It may of given him some good ideas on how he could acquire his fair share of it.
By 1926 he was selling real estate for others around Oceanside in western Nassau county. Then came the stock market crash and the depression. Not the greatest time to strike out on your own but again it was his time to make some major moves.......
In 1930 he married Rose who would be his lifelong companion and in 1932 Walter T. Junior came along.
The next big thing I can find that he tried was "Budd Lake Estates" near Lake Hopachton in New Jersey in 1934. Like the town that eventually would bear his name, Budd Lake was carved out of an estate....the A. H. Smith Estate! and originally marketed by someone else as Country Club Estates. And like that great sage of New Jersey, Lawrence Peter Berra might say: "It was Deja Vu all over again, except this was the first time"