Winston has always been a driven person with a keen sense for business and ‘what can be’ in life. His CRCR experience led to opportunities in International markets with railcar service and metal commodities. His integrity and hard work allowed his strong reputation to grow, thus increasing opportunities in different channels Winston’s way of seeing things through his unique lens made him realize that somewhere there was a path forward for an even successful business that could help the world in measurable ways. When he re-connected with Dennis Pitselis, the vision for that path forward began to crystalize and the partnership that is now Mac W Inc. was formed.​ With a proven track record of international business success, his entrepreneurial spirit and the competitive drive of a former elite athlete, Winston intends to work with his partner Dennis to drive MAC W to places that they believe no others have ventured before.

In 2009, Winston founded Canadian Rail Collision & Refurbish (CRCR), when he saw a market opportunity to create the first-ever facility dedicated to railcar repairs. Less than three years later, the Toronto-headquartered CRCR had grown rapidly, with two U.S.-based railcar repair facilities (based in Chicago and San Diego), in addition to its Canadian presence.