Ascension

 - Born

 - Life with Mama begins

 - Moved in with biological mother

 - Kicked out of home and lived on his own

 - Immigrated to Canada

 - Received Canadian Citizenship

 - Met Christine

 - Married Christine

 - Darian born

 - Brentyn born

 - Keana born

 - Founded Kingsdale Advisors

 - Skyla born

 - Received Ernst and Young’s Entrepreneur of the Year Award

 - Broghan born

 - Established KSS HoldCo (rebranded to WeShall Investments)

 - Received Vice Chancellor’s Award from the University of West Indies

 - Received Honorary Doctorate from the University of West Indies

 - Received AfroGlobal Television Excellence Award

 - Received Communicator of the Year from the International Association of Business Communicators, Toronto

 - Listed as 50 most influential Torontonians by Toronto Life

 - Founder & Chairman, The BlackNorth Initiative

 - First Black Dragon to appear on CBC’s Dragons’ Den

 - Received Honorary Doctorate from the University of Ottawa

 - Received Global Citizens Award from the United Nations Association Canada

 - Received Social Impact Award from the Toronto Black Film Festival

 - Received Lifetime Achievement Award from the Ontario Chamber of Commerce Business Achievement Awards

 - Received Honorary Doctorate from Toronto Metropolitan University

 - Listed as Canada’s 50 most powerful people by Maclean’s The Power List

 - Listed as Canada’s 50 most powerful people by Maclean’s The Power List

 - Received Canadian Business Leader of the Year from the Canadian Chamber of Commerce

 - Received Honorary Doctorate from Queen’s University

 - Received Medal of Distinction from Huron University

 - Wrote a best-selling memoir ‘No Bootstraps When You’re Barefoot’

 - Rebranded KSS HoldCo to WeShall Investments

 - Received Global Black Coalition, Success, Legacy, and Empowerment Award

 - Received Honorary Doctorate from the University of Toronto

 - Received Volunteer Award from Toronto Metropolitan University

 - Received Honorary Doctorate from York University

 - Received Peace Patron Award from the Mosaic Institute

 - Listed among the top 3 finalists for the National Business Book Award

 - Top 40ish larger than life personalities who shaped Bay Street over four decades

 - Nation Builder of the Year award by Empire Club of Canada

 - Knighthood of The Royal Order of Constantine the Great and Saint Helen