Heald was born in Red Bank, New Jersey. He was raised in Middletown Township, New Jersey and attended Middletown High School South, where he played the trombone and was a drum major in the school's marching band.
Heald was studying finance at the University of Pennsylvania's Wharton School, with Jon Hurwitz who lived in the same dorm with him during freshman year. As Hurwitz's high school friend Hayden Schlossberg (who was in college at The University of Chicago) frequently came to visit, Heald also got to know him as well.
During his time at Wharton, Heald was the editor-in-chief of 34th Street magazine, and he briefly considered a career in journalism. Ultimately, he accepted a position in finance, but was laid off during the Dot-com bust in 2001. He then joined Hurwitz and Schlossberg in Los Angeles, where he worked as a screenwriter.

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