Pentland was born in Newtownards, Northern Ireland, UK. He emigrated to Lower Sackville, Nova Scotia in 1975 with his father (Richard), mother (Patricia) and sister (Danielle). In 1977, Pentland's father's work saw them moving to Montego Bay, Jamaica, for eighteen months. Returning to Nova Scotia in 1979, they settled in Middle Sackville (outside Halifax), where Pentland remained until he moved out of the family home in 1991.
Pentland attended Sackville High and Millwood High. After graduating, he attended The University of King's College, entering the school's journalism program. Pentland left the program in his second year, and eventually graduated with a BA in history, of which he claims to have retained very little knowledge.
It was during high school that Pentland became serious about playing music, guitar in particular. His father had played in rock bands—or show bands, as they were known—in Northern Ireland throughout the 1960s and early 1970s. This influenced Pentland to follow in his father's footsteps. He had learned recorder in grade school, and played saxophone in his junior high school band, but he eventually settled on guitar as his main instrument.

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