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Heisman graduated from Hatboro-Horsham High School in Pennsylvania as the co-valedictorian in 1968, and was elected to the school's Hall of Fame in 2007. He attended Caltech and transferred to Penn State in 1969. In 1971 Heisman graduated at the top of his class earning a B.S. in Mathematics, and in 1983, again at the top of his class with a 4.0 G.P.A., received his Masters Degree in Engineering, both from The Pennsylvania State University.
Heisman began his career as an engineer and worked in that capacity with several organizations, including the Naval Air Development Center and Intermetrics, Inc. Later, Heisman became a Registered Investment Adviser in Pennsylvania. He has been a full-time chess instructor and author since 1996.
Heisman is the two-time Open chess champion of Philadelphia (1973 and 1976), and the Philadelphia Invitational Chess Champion (1973). His Penn State team won the U.S. Amateur Team Championship in 1972. He is rated over 2200 by both the United States Chess Federation and FIDE, but is currently inactive as a tournament player. Heisman is a member of the International Computer Games Association and worked at both Deep Blue versus Garry Kasparov matches (1996 and 1997).
Heisman authors the award-winning Novice Nook column, aimed at improving adults, for the popular Chess Cafe Web site. He has also written eight books on chess, including Elements of Positional Chess Evaluation, Everyone's 2nd Chess Book, and Looking for Trouble.
Heisman is well known throughout the Philadelphia chess scene. His chess activities include promoting local chess, hosting a chess radio show "Ask the Renaissance Man" on ICC Webcast, and organizing events like the Philadelphia Championship and Philadelphia Junior Championship. He is currently a member of the Main Line Chess Club and the SE Scholastic Coordinator for the Pennsylvania State Chess Federation. He maintains an extensive web page which provides information on Philadelphia area chess and many articles on chess improvement. Heisman is a chess tutor and among his current students is radio DJ Howard Stern. He helped mentor the 2007-08 National High School champion Dan Yeager, who attended his old high school (Hatboro-Horsham High School).
Heisman is married to Shelly Hahn. His first wife, Susan "Holly" Hollis Bloom Heisman, died of breast cancer in 1994; they had one son, Delen, a graduate of Carnegie Mellon University. Heisman was born in Willow Grove, Pennsylvania in 1950 and currently lives in Wynnewood, Pennsylvania.
He is a member of the Society for American Baseball Research and had a baseball newsletter, "Baseball's Active Leaders". His hobbies include backgammon, science fiction, collecting comic books, and following the Philadelphia sports teams.
- Heisman, Dan; Knott, John (2010). Elements of Positional Evaluation. Russell Enterprises. ISBN 978-1-888690-58-3.
- Heisman, Dan (2010). A Guide To Chess Improvement. Everyman Chess. ISBN 978-1-85744-649-4.
- Heisman, Dan (2012). World's Most Instructive Amateur Game Book. Newton Highlands, MA: Mongoose Press. p. 328. ISBN 978-1936277438.
- Heisman, Dan (2009). The Improving Chess Thinker. Newton Highlands, MA: Mongoose Press. p. 224. ISBN 978-0979148248.
- "Nominations received for Chess Journalist of the Year (2007)". Chess Journalists of America. Retrieved 2008-02-01.
- McClain, Dylan Loeb (October 19, 2008). "Long a Player, Howard Stern Gets Serious About His Game". The New York Times. pp. A36.