Singh's first job in the restaurant business outside the family business was as a waitress at Bakers Square. After an aborted attempt to join the US Air Force (due to a failed medical exam), she applied for a job at a fine dining restaurant but needed better background on wines. She self-educated and re-applied for the job, impressing the interviewer, who hired her and encouraged her to continue her studies. She became a sales clerk at Nielsen Bros. Market in Carmel, California which further exposed her to the wine business.