Reynolds read comics from an early age, and remembers being fascinated by a stack of Superman comics he saw when he was young.
Reynolds was moving towards a career in journalism when he was in university in California and was managing editor and cartoonist for his university newspaper. In the spring of 1993, he came to the realization that Fantagraphics published almost all of his favorite comics. He decided to contact them looking for a job. He got a job a month later, and stayed in Seattle for three months before returning to university. After finishing his degree a semester later, he returned to Fantagraphics and has remained there ever since.
Reynolds worked as news editor for The Comics Journal from 1993, covering such events as the rise of Image Comics, the Mike Diana controversies and the general downturn in the comic book industry, before moving to marketing and promotion in 1996.