Yoshihara always loved drifting but saw no real economic opportunity in the sport. Yoshihara instead worked in more stable, long term jobs, taking on jobs at various companies including a car dealership, a telephone company, and a trucking service. However, in 2003, Yoshihara was offered a chance to compete in the 2003 D1 Grand Prix in its inaugural season in the United States, and accepted the offer, although he had never been prior or even competed in a drift competition. Yoshihara entered the D1 driving for Pacific Rim Motorsport in a Nissan Silvia (S13). Having never competed, Yoshihara was a rookie with no competition experience but qualified and finished in the top half out of 32 competitors. Yoshihara then competed in the Drift Showoff in Irwindale, California and took a podium spot to finish 2nd overall.
Yoshihara ended his maiden season of 2003 with multiple wins. As a result, he was entered into the 2004 Formula Drift Championship Series the following season. Yoshihara finished in the top 8 at two rounds and placed 2nd at two of the rounds placing him 2nd overall in the championship run. Yoshihara earned the accolade of being the driver with the fastest entry speed every time he raced in the 2004 Formula Drift season. In 2005 and 2006 Yoshihara earned even more success in the Formula Drift series with multiple podium finishes, and in 2007 finished 3rd overall. In 2008, Yoshihara entered with a factory-backed Pontiac GTO for RMR Racing, along with teammate Rhys Millen. Yoshihara ended the 2008 season with a podium finish and placed 2nd overall during the Red Bull Drifting World Championship. Throughout the 2008 season, Yoshihara took podium twice and eventually finished 4th overall in the Formula D series.
The 2009 season saw Yoshihara signed to Falken Tire, driving a V8 powered Lexus IS350. Throughout the 2009 season, Yoshihara and his new team experienced developmental problems with the Lexus, eventually crashing and retiring it. Yoshihara finished off the season driving a team built Nissan 240SX. Yoshihara finished in 11th place for overall championship points.
In 2010, Yoshihara signed on for another season with Falken, continuing with the 2009 season’s Nissan 240SX, which was now further modified, receiving a motor transplant and major suspension tuning. Yoshiharaended the 2010 drift season in 4th place in overall championship points.
Yoshihara continued to drive for Falken for 2011, with the same Nissan 240SX as he did in the 2009 and 2010 seasons; however, with more changes to the car, Yoshihara finished the 2011 season as Formula DRIFT champion and also won the Triple Crown award.
Yoshihara drove the Nissan 240SX through 2012 and 2013 where he finished 7th and 11th respectively. For the 2014 Formula Drift season, he switched to a 2014 Subaru BRZ.