His grandfather, Saproon Singh Dhillon moved to Hong Kong from India to establish a shipping company and carry out trade with Japan.
While in school, Dhillon's family was living and conducting business in Liberia, however were forced to leave due to civil unrest.
[6] Dhillon founded Mainstreet Equity Corp in 1997, taking the company public and listing it on the Toronto Stock Exchange under (TSX: MEQ) in 2000.
[9] Dhillon is developing a high-end tourist resort in Belize,[5][10] a nation for which he is also the honorary consul general to Canada.
[14] On December 29, 2021, Her Excellency the Right Honorable Mary Simon, the Governor General appointed the Order of Canada to Dhillon.