After graduating from Princeton, Rossi returned to Toronto to pursue a career in the private sector with roles at Advanced Material Resources (now NeoMaterials), the Boston Consulting Group, Torstar, Labatt/Interbrew and MGI Software.

[7] In 2011, he won the PC nomination for the riding of Eglinton—Lawrence and ran as a candidate for MPP in the 2011 Ontario general election.

[10] Rossi is an adventurer who has completed numerous endurance feats including walking the Camino de Santiago,[11] which is a major Christian pilgrimage route, cycling the 1,900 km length of Yonge Street for charity,[12] and kayaking over 500 km from Toronto to Ottawa.

Among other things, that legislation guaranteed workers paid sick days, equal pay for part-time work, and a C$1/hour raise to a minimum wage of C$15/hour, to begin on January 1, 2019.

[16] On December 31, 2018, the day before the cancelled minimum wage increase was to take place, Rossi tweeted photos of caviar, Veuve Clicquot champagne and pastries, with the statement "Celebrating New Year’s the 1-percenter way!