When Geary arrived in New York he had the chance to jump right in at the famous Sin-é bar. However, he felt a little intimidated at that early stage in his career. "It was a huge amount of pressure," said Geary. "I walked in and saw Jeff Buckley, Katell Keineg, Sinéad O'Connor." So Geary began to seek out gigs at less exalted local spots. He built a reputation playing at Sidewalk Café and won a regular slot at the Pink Pony. Eventually, working his way back to Sin-é, where he found himself on a regular bill sandwiched between Keineg and Buckley. Geary also worked and regularly performed in the popular New York bar "The Scratcher".