In 1995, she was invited to become a "front-line investor" for Borders Group, the American book retailer, which was planning to enter the Canadian market. When Borders was unable to obtain the necessary federal regulatory approval in Canada, Reisman entered big box book retailing on her own, founding a company called Indigo Books and Music. She raised $25m from a group of investors based on the original concept document for Indigo. In 2001, Indigo Books and Music acquired its main rival, Chapters, to form the largest book retailer in Canada, obtaining a clear leadership position in the book retailing industry. Reisman co-founded Kobo Inc. in 2009 and two years later, sold Indigo’s majority stake in Kobo to the Japanese company Rakuten for $315 million.