Isaac Olowolafe Jr., President of Dream Maker Inc, a Toronto-based asset management firm, started his entrepreneurial journey at just 22 years old. Now at 36, he credits the support of his parents, wife and his community for his success — and he’s paying it forward, with venture capital investments and philanthropic support guided by a diversity and inclusion mandate.
by Hailey Eisen
At 36 years old, Isaac Olowolafe Jr. has experienced great success in business at the helm of Dream Maker Corp., a diversified asset management company with divisions in real estate, development, property management, and insurance. He’s also contributed greatly as a philanthropist and is an active champion of diversity and inclusion. Isaac, however, won’t take personal credit for any of it — attributing all of his success, instead, to his upbringing and the unwavering support of his family and community.
“My parents moved our family to Canada from Nigeria when I was 4,” he recalls, “and I grew up in a rough area of Toronto.” When Isaac was 15 his family moved again, this time to Woodbridge, a large suburban community north of the city.
“Being one of the only black students in a primarily Italian community was certainly a culture shock,” Isaac recalls. And, while he recognized that he was outside of his comfort zone, he realized he had a choice to make — focus on the negative and sulk in the corner for the rest of high school, or make the most of it.
Being optimistic by nature, Isaac chose the latter path and quickly found inclusion into his new community through sports. “There are certain things that make people colour blind and one of them is sports,” he says. “It’s a great equalizer.” So, Isaac joined the soccer team and learned to play Bocce Ball. He made friends and focused on all the positive things his new community had to offer — including a strong work ethic and business sense.
“I was exposed to a lot of the businesses built out of Woodbridge, such as real estate, development, and construction,” Isaac says. “And, my dad was also a real estate broker, so I was exposed to real estate not only from my environment, but also from watching my dad. I saw real estate as a tool to create generational wealth, not only to take care of your family but also to build up a community.”
At just 22 years old, and in his second year at the University of Toronto in Mississauga, he launched Dream Maker Corp. — then, just a real estate investment company. Eight years, and a lot of hard work later, he added real estate development to his growing company. His first project was a $40 million mixed-use condo development across from Yorkdale Mall. “I wasn’t a typical developer, and many lenders said ‘no’ right away,” he recalls. Throughout the project, he faced many roadblocks — but he also received much support. In the 16 years since he set out as an entrepreneur, Isaac’s business has grown substantially. He’s remained committed to his roots, however, crediting his connections and contacts with opening doors and helping him overcome roadblocks.
With a realization that the technology ecosystem is what continues to drive the real estate and development sectors, Isaac became interested in providing support and funding to tech entrepreneurs — especially those from diverse backgrounds. He launched Dream Maker Ventures Inc. (DMV), the investment arm of Dream Maker Corp., to fund early-stage startups in this space.
“Nothing good comes easy, regardless of you being a woman, or from the black community, or from any type of diverse group, with enough hard work, you can crack through and achieve your goals.
As a venture capitalist, he believes that those companies that work with Dream Maker Ventures are innately open to different viewpoints — and he brings that to the table, no matter who he’s working with. “We work with the companies we fund to bring a diverse perspective to hiring and product development, among other things,” he says.
Their latest initiative takes this a step further. Through the recently-launched “Diversity Fund,” Dream Maker Ventures will make early-stage, seed, and Series A investments in tech companies with founding teams inclusive of persons of colour, women, persons with disabilities, LGBTQ+, immigrant, refugee, and indigenous entrepreneurs.
Isaac’s goal through this fund is to help change the narrative around entrepreneurship. It also makes good business sense, he says. “Statistics show that diversity not only creates a more positive work environment, but can also help companies build better products overall.”
As a philanthropist, Isaac has, for the most part, focused his efforts on inclusion in the startup space also. Through the Dream Legacy Foundation, Isaac’s philanthropic arm, he gives back to the community by supporting programs and initiatives that help entrepreneurs from underrepresented communities, and provides access to key resources that are critical to long-term success. This essentially creates a pipeline of diverse entrepreneurs within the ecosystem that are suitable for future investment by Dream Maker Ventures and other venture capitalists. Such programs include the DMZ Black Innovation Fellowship, based out of Ryerson University; Fierce Founders, a bootcamp program for female entrepreneurs; and Access to Success, which supports future business leaders with disabilities, among others.
“The challenge most entrepreneurs of any diverse group face, is access,” Isaac says. “Access to mentorship, funding, and resources.” The access he was given when he was starting out is what he hopes to provide for others. The Black Innovation Fellowship, for example, is the first fellowship program in Canada to provide startups led by Black entrepreneurs with mentorship, events, industry connections, capital, and an alumni network to support growth.
“This is a five-year initiative, and I hope that in five years there’s no need for a program like this — that it will be normal to go into any incubator and see black-led, female-led, and other diverse population-led startups,” Isaac says.
In the future Isaac envisions, his daughters, now 4, 6, and 9, won’t face challenges specifically because of their gender or race. For now, however, he’s focused on teaching them about the value of hard work. “Nothing good comes easy,” he says. “Regardless of you being a woman, or from the black community, or from any type of diverse group, with enough hard work, you can crack through and achieve your goals.”
What is the role of men in gender equality? Over the next year, the 30% Club Canada and Women of Influence are partnering to explore this question. We’ll be sharing the stories of allies — men who are pushing for gender equality in the workplace, or making it happen in their own business. These Champions of Change can act as visible role models, inspiring and guiding other men to follow in their footsteps. If we’re going to level the playing field, we need men to be engaged.