After several years working as a bodyguard for Danzig, Slayer, and occasionally for other bands such as Soundgarden, James opened West Coast Choppers in his mother's garage in 1992. The company grew quickly and soon moved to a larger facility for select customers and companies. About 200 bikes have been built at West Coast Choppers. West Coast Choppers is also sponsoring race teams in Top Fuel Drags and Super Late Model NASCAR. James recently bought custom car business Austin Speed Shop and has expanded into the custom car business. Jesse James has also built and is racing an off-road Trophy Truck and a Figure-8 race car.
He was the owner of the Cisco Burger restaurant, which opened on April 28, 2006, just down the street from West Coast Choppers. The 1950s style hamburger stand—named after his beloved pit bull who is now deceased—featured Angus beef burgers, low-fat burritos, organic vegetables, and biodegradable wrappings. It has officially closed. James also has partial ownership in the South Austin Speed Shop in Austin, Texas.
Other business ventures include the Chopperdogs fan club and the Jesse's Girl clothing line. Since 2006, James has nationally published Garage magazine.
In 2000, the Discovery Channel made the documentary Motorcycle Mania, which chronicled James' everyday life. Following the success of the documentary, the Discovery Channel approached James with an offer to host a new show called Monster Garage where James and a crew of mechanics modified vehicles under a short deadline.
James later established Payupsucker Productions, under which he produced shows like History of the Chopper, Iraq Confidential with Jesse James and Green Scream, in which James plans to break the land speed record with an eco-friendly hydrogen car.
He also had an appearance on Discovery Channel's Sons of Guns.
He appeared on the second season of Celebrity Apprentice. Each celebrity played to raise money for a favorite charity; James selected to play for the Long Beach Education Foundation. Due to his poor performance in raising funds, James was eliminated by Donald Trump on the second-to-last show (ultimately placing 3rd) which aired May 3, 2009. Trump repeatedly cited James' stoic refusal to contact then-wife Bullock to raise funds for the show's challenges, though other celebrities had no problem tapping high-rolling contacts for cash.
His show Jesse James is a Dead Man premiered on Spike TV on May 31, 2009. The show features James doing death defying stunts. The first episode set a ratings record for Spike, drawing the largest audience ever for an unscripted series on the network, with 2 million viewers. The show is produced by Spike TV, BASE Productions and James' company, PayupSucker Productions.
James' Discovery Channel website states that his great-great-grandfather was the notorious outlaw's cousin.
However, Eric James, president of the James Preservation Trust, which tracks claims of being a relative of the outlaw, says it cannot find a record of him in the family tree, and has asked him to provide a family genealogy and DNA sample for the Trust to review; he has not provided the requested information.
James has three children—a daughter and a son with his first wife, Karla, and a daughter with his second wife, stripper/porn star/producer Janine Lindemulder.
In October 2009, James' ex-wife Lindemulder, who had been in federal prison for six months for tax evasion, sought to regain custody of her then five-year-old daughter with James, Sunny, after James had been granted sole guardianship of her. James sought to retain full guardianship, citing fear of the environment in which his daughter would be placed if returned to Lindemulder. In December, James won custody, and Lindemulder was given weekly visitation rights during the daytime.
In March 2010, a media scandal arose when several women claimed to have had affairs with James during his marriage to Bullock. Bullock cancelled European promotional appearances for The Blind Side citing "unforeseen personal reasons". On March 18, 2010, James responded to the rumors of infidelity by issuing a public apology to Bullock. James declared that "There is only one person to blame for this whole situation, and that is me", and asked that his wife and children one day "find it in their hearts to forgive me" for their current "pain and embarrassment". James’ publicist subsequently announced on March 30, 2010 that James had checked into a rehab facility "to deal with personal issues" and "save his marriage" to Bullock. However, on April 28, 2010, it was reported that Bullock had filed for divorce on April 23 in Austin. Bullock also stated that she had proceeded with plans to adopt a baby boy born in New Orleans. Bullock and James had begun an initial adoption process four years earlier. The child began living with them in January 2010, but they chose to keep the news private until after the Oscars in March 2010. However, given the couple's separation and then divorce, Bullock continued the adoption of the baby as a single parent. The divorce was finalized on June 28, 2010, with "conflict of personalities" cited as the reason.
On August 19, 2010, Kat Von D confirmed media reports that she and James were dating, tweeting "I think it's pretty obvious that we're dating. " Von D and James announced their engagement on January 20, 2011. Von D announced their split via Twitter on July 26, 2011. On August 18, 2011, the two announced their engagement was back on. On September 24, 2011, Von D announced that she and James had split again.
In 2007, James was fined $271,250 by the California Air Resources Board (CARB) after state officials determined that he had sold motorcycles in violation of California's clean-air laws. According to police, James' customized bikes were emitting 10 times the legal limits of hydrocarbons. Investigators also found that the motorcycles did not have state-certified emissions equipment on their fuel systems. The bikes were sold between 1998 and 2005. James explained that he was unaware of rule changes that required small-volume manufacturers to comply with regulations. James said the CARB refused his offer to recall and modify the uncompliant choppers. Since 2005 West Coast Choppers has built emissions-compliant choppers. James said the fines were excessive and intended to make an example of him due to his company's fame and his celebrity marriage to actress Sandra Bullock, but CARB spokesmen stated their enforcement efforts were aimed at the entire custom industry, and further that they were aware of no offer by West Coast Choppers to recall the motorcycles in question.
In July 2008, James faced a $422,680 breach of contract lawsuit from Michael Jones, a customer who hired James to build him a custom car, who contended that after paying $270,000 over two years, the car was not completed, and that James informed him that it would cost between $600,000 and $700,000. That September, James faced another lawsuit from his former lawyer for $327,533 in unpaid fees.