As a kid Wolff had a local paper route and was a Boy Scout. After attending Concrete High School in Concrete, also in the North Cascades, Wolff applied to and was accepted by The Hill School, located 35 miles from Philadelphia, Pennsylvania. He had applied under the self-embellished name "Tobias Jonathan von Ansell-Wolff III", adopting part of one of his father's personas, Saunders Ansell-Wolff 3d. When Wolff was found to have had forged his transcripts and recommendation letters, he was later expelled.