After graduating from college, Kaplan worked for Condé Nast.[4] He was later the vice president and general manager of Geoworks. He was also the founder and CEO of MovieStreet. Kaplan was the president and CEO of Sega.com and was the chairperson and CEO of Pure Digital Technologies. In his role, Kaplan invented and marketed the Flip Video before the company was acquired and shuttered by Cisco Systems.[5][6][7] Most recently, Kaplan was the chairperson and CEO of the FishSix Restaurant Corporation, a holding company that owns several grilled cheese sandwich restaurants in California, Texas, and Colorado.[8][9]
United States ambassador to Singapore
On July 29, 2021, President Joe Biden nominated Kaplan to be the next United States ambassador to Singapore.[10][11] The Senate Foreign Relations Committee held hearings on his nomination on October 20, 2021. The committee favorably reported Kaplan's nomination to the Senate floor on November 3, 2021. The entire Senate confirmed his nomination on November 19, 2021.[12][13] On December 6, 2021, he presented his credentials to President Halimah Yacob.[14][15] In February 2024, the Department of State released a watchdog report suggesting Kaplan mistreated staff and wasted money.[16][17][18]