Always interested in the stock market, Englander began trading stocks while in high school. During college, he interned at Oppenheimer & Co. (where his Future brother-in-law, Jack Nash, would eventually become President and chairman) and at the New York Stock Exchange. In 1970, he graduated from New York University with a B.S. in Finance. His first full-time job was with the Wall Street firm Kaufmann, Alsberg & Co. He later enrolled in New York University's MBA program in the evenings but never completed the degree.