An economics graduate of the University of Toronto, Temitope Isaac Olowolafe established Dream Maker Realty Inc, his first business venture, in 2003. He continues to drive operations at the brokerage firm, which manages $200 million in real estate, as a general partner. In the following years, Temitope Isaac Olowolafe expanded operations at Dream Maker, initially launching the boutique real estate development firm Dream Maker Developments in 2008 before adding Dream Fund Holdings, Dream Maker Ventures, and Dream Insurance to his umbrella of businesses. Most recently, he established Dream Performance, a financial literacy curriculum for athletes, and the Dream Legacy Foundation, which aims to bring financial literacy and technology to in-need communities.

As an alum of the University of Toronto, Mr. Olowolafe enjoys giving back to the community. He established the Dream Maker Realty/Olowolafe Family Scholarship Award in 2010, which was recognized as the largest endowment for African studies at a Canadian university. His professional honors, meanwhile, range from the Harry Jerome Business Award to the Enterprise Business Award by Planet Africa. Business award for Toronto Board of Trade