After the initial success of the website, they expanded into producing and filming pornographic DVDs starring other performers. Their company was called 413 Productions, after the street address of the warehouse they rented for filming. The PornFidelity web site and a matching DVD line grew out of some threesome scenes with the couple and women whom Madison brought home. The couple divided the business responsibilities: Ryan handled the production company; editing and photographing; web hosting; programming; advertising; and traffic generation. Kelly handled talent booking; arranging sets; company finances; and promotions.

Madison has also appeared in Score magazine, and she writes a column for Juggs magazine.

Madison has started a series of pornographic web sites. KellyMadison.com focuses on her public appearances. PornFidelity.com focuses on threesomes, swinging with her husband, and women that she brings home. KellyFind.com is a pornographic search engine, specializing in searches for specific types of performers (by ethnicity, hair color, bust size, age, sex acts-performed, etc.). KellyCash.com is an affiliate program for the first two sites, replacing 413dollars.com in mid-2006.

On July 25, 2007, Madison and her husband were interviewed on the E! channel Chelsea Lately television program. They discussed their marriage, their open relationship, and pornographic career. She was nominated for the AVN Awards for "Web Starlet of the Year" and "MILF/Cougar Performer of the Year" in 2009, and for "MILF/Cougar Performer of the Year" in 2010.

Kelly Madison's father was an actor and stunt man and her mother was an accountant; she has two older sisters.

Madison met her husband, Ryan, in 1999 at a computer graphics company. She was the 32-year-old vice president of sales; he was a 22-year-old graphic designer. Despite their age difference, and Kelly's engagement to another man, they fell in love, and eloped.