Whilst working for the family's business, Calvin joined online content network firm, CBS Interactive, for a short stint as an Account Servicing Executive in hope to gain more working experience from another different industry. As an Account Servicing Executive, his duties were to revive 'dead' sales accounts that have ceased their advertising partnerships with CBS Interactive. To note, Apple Singapore was one of the few accounts that Calvin managed to revive.
Following the stint at CBS Interactive, Calvin joined HSR as a Property Consultant in 2010. Within the first month, Calvin clocked in a five-figure sales commission making him one of the few promising newcomers of his division. Moving forward, Calvin set a new high record of a six-figure sales commission for his division within a year. This accomplishment promoted him to an Associate Director.