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David Richard Windeyer graduated from Ryerson with a diploma in Business Administration in 1965. After graduation, Windeyer began a career in the administration and management of estates, trusts, agencies, and charitable foundations. He has held senior positions with the Trust Departments for National Trust, the Victoria and Grey Trust and The Bank of Nova Scotia Trust Company. He was a principal at Sweatman Windeyer Consultants, Chair of the Board and Director at the John Bright Foundation, and Secretary of the J.P. Bickell Foundation, among other positions. In 2009, Windeyer was certified by the Society of Trust and Estate Practitioners of Canada in Administration of Estates and Trusts, earning a similar accreditation from the Trust Companies Institute in 2012. He is a member of the Canadian Centre for Philanthropy and the Canadian Association of Gift Planners. He was the founding Treasurer and Board Member of Philanthropic Foundations of Canada.