Dream Makers

Mindset Reading Investment: 5 minutes


Olowolafe backs 17 startups so far with his investment funds. He just signed a Memorandum of Understanding with Ryerson’s DMZ to set up an Investment Fund to invest in startups around the world that marginalized people would have founded. He’s keen on helping Canadian marginalized startup founders, and wants to see more black people in the startup arena. “This is a major gift to the university, to help make new things happen at all innovation spaces globally, wherever Ryerson’s DMZ reaches

Dream big, live for that dream, and believe you will make it happen. That’s the mindset that pushes Isaac Olowolafe Junior, 35, to achieve astonishing feats, such as currently developing a 42-house glitzy community in Ajax, Ontario. Or giving a million dollars to Ryerson University’s innovation hub, DMZ, to fund marginalized people who are founders of startups around the world.

Born in Nigeria, Olowolafe moved to Canada with his parents at the age of four years. His family lived on the Jane-Finch corridor in North York, and his father felt the neighborhood did not offer the best social environment. So the family moved to Thornhill, Ontario.

Isaac Olowalafe Jnr
Isaac Olowalafe Jnr

At 15 years of age, Olowolafe found himself with new friends, of a different mindset than he had known at school at Jane and Finch. He started hanging out at the homes of these new friends, and got a new grasp of how the well-off approach life. He listened to the conversations, noting how parents and kids conversed, with a mindset to build generational wealth. “Wealth is a generational thing; it flows from one generation to another, and builds gradually over time,” he said.

The Millionaire Mindset magazine interviewed Olowolafe at his posh condo development adjacent to Yorkdale Mall in North York, a glitzy building that transforms the Dufferin-401 neighborhood. Quiet, humble, soft-spoken and neatly attired in a simple style, Olowolafe comes across as a dignified, intelligent, alert guy. He carries himself with a deep self-awareness, and listens intently, never seeming to retreat into his own self-talk. Calm, peaceful, relaxed and confident, he exudes a sense of contentment with life.

This is a man with a deep mission. His heart pulses with the desire to make a difference for marginalized peoples.

His father, Isaac Senior, became a Real Estate agent in Toronto, and for the past 20 years worked as one of the few Nigerian-born agents in Canada. And in Thornhill, Olowolafe made friends with kids whose parents ran construction companies. The two paradigms – Real Estate sales that his Dad did, and construction projects that he heard of constantly at the homes of his friends – started forming his builder’s mindset. He started dreaming of building communities.

He launched his venture, Dream Maker, 14 years ago, when he was just 21 years old. He bought his first property, a condo in Malvern, Toronto, when he was 21, and today has already paid off the mortgage, while earning income on it – a cool $1,500 a month.

Olowolafe attended the University of Toronto in the day studying Economics, and in the night he worked at a UPS store, going home at 4 a.m., grabbing a couple hours sleep, and heading out to school at 9 a.m. He worked, doing that for four years, and paid his mortgage and school tuition. Following his father’s footsteps, Olowolafe became a Real Estate Agent at 23 years old, and two years later opened up his own Real Estate Brokerage. His Dad now runs the Brokerage, with 27 Real Estate Agents on board.

Smart, suave and focused, Olowolafe started providing extra services for his Real Estate buyers and sellers, such as managing investment properties that people purchased through his Brokerage. Soon, he was managing 20, 30 properties for clients. He opened a new wing of Dream Maker, dedicated to property management.

Then, 11 years ago, he got an idea. He approached housing developers and proposed that his Brokerage be given exclusive listing rights for all the houses in the project. Within a short time, he proved that he was selling houses at a fast clip, and developers started handing him development projects before they started building. He would sell these out with ease.

Olowolafe had found the formula for building astonishing wealth, through the trending Real Estate boom that is sweeping Canada.

Five years ago, he launched his own property development initiative, Dream Maker Developments, and bought vacant land, built his own properties, and sold and managed them. He never looked back. His suite of firms now includes Dream Maker Holdings, Dream Maker Realty, Dream Maker Property Management, Dream Maker Developments, Dream Maker Insurance, and Dream Maker Ventures. His business includes Real Estate – from development to brokerage and investment management; insurance; philanthropy; and a Private Equity Fund.

He was 28 years old when he bought vacant land at 16 McAdam Avenue in Toronto, and built Dream residences at Yorkdale Condos, him and his Dad taking out a mortgage. That was his first development, consisting of 87 condo units, four townhouses, and commercial units on the ground floor.

But his biggest passion these days is Dream Maker Ventures, which invests in technology startups through Ryerson’s DMZ innovation hub. Olowolafe backs 17 startups so far with his investment funds.

He just signed a Memorandum of Understanding with Ryerson’s DMZ to set up an Investment Fund to invest in startups around the world that marginalized people would have founded. He’s keen on helping Canadian marginalized startup founders, and wants to see more black people in the startup arena. “This is a major gift to the university, to help make new things happen at all innovation spaces globally, wherever Ryerson’s DMZ reaches,” Olowolafe said.

Married with three young daughters, Olowolafe works closely with his wife, Monique, who has a Masters in Education, to manage his dreams and vision. He’s a man of deep faith, and attends church regularly. He said that the people around him make all the difference in living a life of making his dreams become reality. “My parents, my wife – who encourages me and has been my biggest cheerleader for 14 years now, and my team, they are my biggest ingredient for success. Relationships are important,” he said.

Olowolafe dreams now of creating a legacy teaching and equipping people on how to generate wealth over generational investments. His clients learn how to invest for their children and future generations. It’s a life lesson he wants to bring to Africa as well, although he visits there not so often, being committed to his Canadian projects. His parents, however, visit Nigeria often.

I want to build a legacy for transformation of the mindset of marginalized peoples, for them to use Real Estate and technology” to make their dreams real, he said.

Olowolafe is fast becoming a major asset management expert in Canada, and sees himself as building a portfolio of assets that his companies manage for clients. He’s evolved in his generation from his Dad’s Real Estate agent status and his Mom’s status as a veterinarian doctor at the Toronto General Hospital for 20 years, to become a high flyer in Ontario.

From his home in Woodbridge, he takes a keen interest in startups that operate out of Ryerson DMZ. However, he’s a lone investor, surprisingly not networked in any of the innovation hubs in Ontario. He sees that as unfortunate, as his character, skills and business acumen would do wonders for Canada were the Establishment to bring him in to the fold. However, his work at Ryerson’s DMZ is laudable and astonishing, as he is a single investor engine. Most Angel investors work with a team of other investors. Olowolafe goes in alone, and so far has invested in 17 startups out of DMZ, including being in a round of financing for a DMZ startup, partnering with a major global investment firm.

For me, nothing is impossible. I dream big,” Olowolafe said.

He plays chess, and sees the skills he learns at chess as crucial to how he lives his life. “Chess teaches me about life, how to make moves that are strategic and looks to the endgame of winning,” he said.

Olowolafe is now embarking on launching Dream Performance, an enterprise to provide financial literacy to sports stars, and to help the sports and entertainment industries develop sound financial foundations for talents.

His latest project is Dream Suites, a luxury hotel close to Pearson Airport.

Here’s a young African-born entrepreneur who’s making quiet waves in Canada. Humble, quiet, cool as ever, Olowolafe looks to the future grounded in his faith, that his life on earth is blessed with purpose, vision, and a mission to make dreams become reality. He’s a living testimony that Canada offers anybody the opportunity to live the dream life.


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