Weiss was born and raised in Chicago, Illinois. His family is Jewish. He is a graduate of Wesleyan University. He earned a Master of Philosophy in Irish literature from Trinity College, Dublin with a thesis on James Joyce\'s Finnegans Wake, and a Master of Fine Arts in creative writing from the Iowa Writers\' Workshop.\n', '

Weiss worked as personal assistant on films such as The Viking Sagas for New Line Cinema. For a brief period, Weiss also worked as a personal assistant for musician Glenn Frey. Weiss went to Dublin in 1995 to study Anglo-Irish literature and met David Benioff, the screenwriter of Troy. Three years later they met again in Santa Monica, California around 1998.\n', '

Weiss and Benioff wrote a screenplay for a film titled The Headmaster together, but it was never made. In 2003, Weiss and Benioff were hired to collaborate on a new script of Orson Scott Card\'s book Ender\'s Game in consultation with the then-designated director Wolfgang Petersen. It was not used.\n', '

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