Isaac is an award-winning real estate entrepreneur, angel investor and philanthropist. His corporation, Dream Maker Inc., successfully operates multiple divisions including a real estate development, wealth management, private equity and insurance. The Development division celebrated the completion of the first major mixed-use development (condos, town homes, retail) called Dream Residences at Yorkdale, located directly across from Yorkdale Mall, and has more developments underway across the Greater Toronto Area, Canada. Through his love of sports, Dream Maker Developments became the jersey sponsor of Canada’s Men and Women Senior National Basketball Team (2018-2020).
Mr. Olowolafe is the recipient of the Arbor Award from the University of Toronto, Toronto Board of Trade Award for Business, Harry Jerome Business Award, Enterprise Business Award by Planet Africa, Business Leadership Award by Leadership and Governance Canada Inc. and featured in City Mogul 2019 list.
In addition to his membership in the Ryerson Innovation Circle, Mr. Olowolafe made a generous donation which named the Isaac Olowolafe Jr. Digital Media Experience Lab in Ryerson’s iconic Sheldon & Tracy Levy Student Learning Centre (SLC). Mr. Olowolafe also funded the launch of the 1st Black Tech Incubator (BIF 1.0) out of Ryerson DMZ and is on the board of DMZ. In 2019, Mr. Olowolafe launched Dream Maker Inc. Fellowship in Sickle Cell Disease at SickKids in partnership with Dream Legacy Foundation and joined the Board of Directors of SickKids Foundation in June 2020. In 2020, Mr. Olowolafe also launched Black Innovation Fund (BIF 2.0), focused on funding Black Entrepreneurs in Technology.
Mr. Olowolafe received a Bachelor in Economics from the University of Toronto, is married with 3 daughters.