Calvin started his career in 1997 as a Dairy Queen franchisee and self-serve car wash operator (The Wave Car Wash). After selling the DQ and returning to graduate school, he co-founded Neptune Properties Inc., a Winnipeg-based family office whose initial focus was commercial real estate in Winnipeg. 

The real estate portfolio today consists of over one million square feet of industrial and retail assets in Western Canada and industrial assets in Minnesota. In 2005 Neptune expanded its investment strategy to include direct investment in operating companies, participating in the start-up of Prairie West Ice Cream, a private-label ice cream manufacturer in Winnipeg. In 2012 Neptune partnered in the formation of True North Foods, a federally-certified beef-processing facility based in Carman, Manitoba. Both food production companies serve clients coast-to-coast and are in the midst of expansions, with True North Foods having the goal of becoming the fifth-largest beef-processing plant in Canada by 2025. 

As President of Neptune, Calvin, has responsibility for oversight and strategy and leads the files for acquisition and disposition of assets, in addition to providing governance oversight in the operating companies.  He also provides oversight and guidance for the family ownership component of Neptune.  He holds a BA in Economics and an MBA from the University of Manitoba and an ICD.D designation from the Rotman School of Management at the University of Toronto.