Gary was born in Queens, New York. His family moved from Far Rockaway to Hewlett Long Island. They weren’t poor, but his father always lived his life as though they were still in the Great Depression. His mother was a housewife, and his father was a businessman in garment district in New York City.
Gary owes his writing career to his reading teacher Mrs. Klein. She taught Gary there was more to reading than just American Indians and baseball books, which were all Gary liked to read in high school.
Gary became an avid reader and took to writing poetry. He wanted to be a novelist, which he pursued first at Lafayette and then at New York University. As a young man he decided he wanted to become the opposite of his father. A poet sounded like a good option for him. Contrary to most writers, Gary was also very athletic and started his Lafayette College years on the freshman basketball team. At NYU Gary was runner-up for a Rhodes Scholarship in literature and turned down a Wilson Scholarship in literature.
Gary’s dreams of a professional baseball career were dashed after a rotator cuff injury. He attended the NYU Law School for a year and then decided to try his hand at teaching literature. But quickly, Gary realized that teaching seventh and eighth grade in New York City was not going to be very rewarding emotionally or financially. He was seriously disillusioned how the young students were taught literature — and how the system and tenure was so entrenched.
The following year Gary entered the MBA program at Columbia University. He liked this curriculum much better.
Gary remained at Lazard Frere for a year until he learned how to evaluate the real estate deals and find them. Then he partnered with one group in his first year to find and syndicate real estate. That partnership left Gary without the $1 million he had earned as his share. The second partnership was a repeat of not getting the money he had earned.
Gary swore off partnerships and struck out on his own with a loan of $15,000. He decided to pursue investment banking and raising money for startups, early stage businesses, and real estate.
By age 31, Gary retired to Boca Raton to write and raise his two children. After his ownership in coal mines and entertainment businesses soured, he returned to his investment banking and real estate businesses.
Gary became fascinated with the idea of universal principles and repeating patterns of success. He began to study from pre-biblical times to the present what made some people successful and others not. Gary began to develop models that incorporated these universal principles and patterns. He’d study up to 12 hours a day.