After serving for greater than a decade as Editor-and-Chief of THE BRAND NEW York Observer, he held an executive position within the style magazine division of Fairchild Magazines. He is probably best appreciated for his crucial role in getting journalism in to the digital period. While their studies at Harvard College or university, he roomed with among the sons of Robert F. Kennedy. After graduating from university, Kaplan proved helpful for Esquire, Manhattan, Inc., and THE BRAND NEW York Moments. He edited a fresh York Observer anthology entitled The Kingdom of NY. With his initial wife, Audrey Walker, he previously children called Peter, Caroline, and Charlie. His second relationship, to Lisa Run after, produced a boy named Davey. Within a 2009 bout of The Charlie Rose Present, he discussed the consequences of the web and cellular devices upon journalism.