In 1999, Pinsky co-founded an Internet-based community and advice site for teenagers called DrDrew.com with Curtis Giesen. Among their early backers was Garage.com. DrDrew.com soon ran out of funding, and the company was sold to Sherwood Partners Inc., a corporate restructuring firm, which sold the remnants to DrKoop.com in November 2000. Pinsky re-acquired the site circa 2013 and began using for general information about his books, radio and TV shows, as well as hosting his independent podcast, The Dr. Drew Podcast. In September 2012, Pinsky announced on The Adam Carolla Show that he will be doing a podcast on the Carolla Digital network.