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.

Jeff Perera credits his upbringing — and the negative male role models in it — for leading him towards his current career: as a speaker, writer, and facilitator focused on a modern view of manhood. His approach avoids shaming men for their learned biases, and instead encourages them to support each other as they build their ‘empathy muscles’, celebrate their differences, and set themselves free from the stereotypes they grew up with.

by Hailey Eisen

Jeff Perera has spent more than a decade working to inspire a shift in what it means to be a man in today’s society. “Quite simply, our ideas of manhood are outdated and are no longer serving us,” explains the 44-year-old speaker, writer, and facilitator who has delivered keynotes, talks, and workshops to tens of thousands of people across North America.

“I aspire to breach conversations in a brave way,” Jeff says, “to build a bridge between the genders and provide opportunities to support one another as we move toward the awakening of modern men.”

He traces the roots of his passion back to his childhood. Raised in Canada by Sri Lankan parents who emigrated via the UK, Jeff recalls having a staunchly ‘Canadian’ upbringing. “I grew up speaking English, eating mac and cheese, and watching hockey,” he says. “My parents experienced a great deal of racism in England and wanted a different experience for me here in Canada.”

Part of his understanding, and critique, of manhood came from his own father’s abusive behaviour toward his mother. “My mother was an extreme example of what women and girls endure, but I learned early on that my father was broken,” he says. “And I was seeing similar behaviours in the socially and emotionally challenged community I grew up in.”

As a man of colour, Jeff says, there were additional stereotypes he had to navigate. “Whether it’s the negative ones, the narrative that group X is lazy and group Y is smarter, or other stereotypes that feel complimentary, like this group is more athletically inclined or this group is more hard working — they’re still treating you as ‘other than’,” he says. 

As a teenager, Jeff rejected a lot of the traditional stereotypes that were pushed on him. But it wasn’t until he was in his thirties and went back to school to study social work at Ryerson, that he realized how he could take his beliefs and put them into action. 

As a mature student, Jeff got involved in human rights work on campus and joined White Ribbon, the world’s largest movement of men and boys working to end violence against women and girls. For years he co-chaired the White Ribbon Campaign on campus and organized events and facilitated workshops. This led into a full-time role with White Ribbon, followed by a position with Next Gen Men, a non-profit organization that promotes positive masculinities, healthy relationships, and gender equity. He eventually started his own freelance business — spreading a message of healthy versus harmful ideas of manhood — which he’s been running successfully for four years.

“For most boys, there’s a moment of trauma where childhood ends and they’re encouraged to ‘man up’, but when they enter their first romantic relationship, suddenly they’re expected to contribute emotionally and don’t have the tools to do so.”

Today, he’s speaking and facilitating workshops to help create a map of modern manhood that’s more inclusive, accessible, and puts equity first and foremost. “As a collective society, we’ve instilled traditions and ideas of masculinity that don’t serve us in a lot of ways. There’s the hunter-gatherer narrative, there’s manhood measured by dominance, what we own, what we demonstrate or produce, and our access to power,” he says. “But what I always say is the measure for manhood should be how we give and how we live.”

Through his work, Jeff is tackling the stereotypes that he grew up with — and more. Be it gender, ethnic or cultural background, or disability, “what we really want to do is to recognize those differences and celebrate them,” Jeff says. “We want to be able to say, ‘like you, I am different.’”

But what about those men who aren’t ready for that message? We may find ourselves feeling defensive or reactionary if our differences are challenged rather than celebrated — but shaming others for their learned biases isn’t going to change them. Real change begins, Jeff says, when we have more living examples of what manhood should look like, and role models leading the way. This is what he’s set out to do, and he’s encouraging other men to join the conversation via his website, Higher Unlearning.  

From a corporate perspective, Jeff urges companies to think about more inclusive hiring and to “dip your toe into the pool and try to see what it will feel like for a woman, or a gay man, or a person of colour.” It’s about becoming aware of your blind spots and doing what you can to change those. This includes stepping up as a champion and contributing to a culture of caring. 

“We have to ask ourselves, what can we do to ensure our work environments are more inclusive?” This can be impacted by simple things such as the language that’s being used, the activities chosen for team building, the culture of respect being garnered, and the focus on listening to what women, and others, have to say.

Jeff believes that most men need to work on building their “empathy muscles,” which tend to get stunted in childhood. “For most boys, there’s a moment of trauma where childhood ends and they’re encouraged to ‘man up’,” he says. “But when they enter their first romantic relationship, suddenly they’re expected to contribute emotionally and don’t have the tools to do so.” 

To build empathy, Jeff says, men need to go back to the metaphorical gym and work on the muscles they want to grow. “Men also need to step up and spot one another in this process,” he says. “As I always say, compassion without action is just observation. If you want change, you need action.”

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.

Coined by Anjuan Simmons, the term ‘lending privilege’ describes using your own position or power to help underrepresented or disadvantaged groups. What does it look like in action? We spoke to Matthew Jefferson, who walked from BC to Newfoundland to raise awareness on the issue of missing and murdered indigenous women, and Jordan Hart, who completed 100 days of busking to raise money and awareness for people with intellectual disabilities. Here’s how they are using their own privilege to help others.

By Hailey Eisen

Anjuan Simmons has travelled the globe speaking about diversity and inclusion, but his focus remains on ‘lending privilege’ — a phrase he coined with the intention of galvanizing action. The Texas-based technologist, speaker, and author believes that every single person has the ability to use their own position or power — no matter how great or small that may be — to help others. 

“The term ‘lending privilege’ means the willingness to take two actions,” he explains. “First, you have to be willing to recognize your own privilege, that is to understand how your gender, race, level of physical ability, and other factors provide access to resources. Second, you have to be willing to share your privilege with others.” 

While lending privilege isn’t exclusively done by men — there are many examples of women lending privilege in extraordinary ways every day — Anjuan says men, given their traditionally inherent power, have a vital role to play. 

“I always encourage men to recognize the power they have by changing how they think about justice,” he says, and that includes recognizing the systemic bias and barriers women face. “These experiences limit the job opportunities women can pursue, the promotions they receive, the salaries they are paid, and even how safe they feel walking down the street. If men can see that unfair system and care enough to create a better experience, then they can do their part in changing the system.”  The result actually makes the workplace — and home life — better for all genders.

To make real change, there are a number of simple actions individuals can take. Lending privilege can be as easy as nominating someone for recognition or a particular assignment, inviting junior colleagues to meetings with leaders, sharing information with individuals who don’t have the same access you do, standing up for the equal pay or rights of a colleague, joining a campaign like 30% Club Canada with a focus on gender-balanced leadership, or stepping into the role of mentor or champion.

Matthew Jefferson is a man who has taken the concept of lending privilege one step further. Or, more like a million steps further. On June 25th of this year, Matthew completed a year-long, 8,275-kilometer walk — from Victoria, BC to Cape Spear, Newfoundland — with the intention of bringing awareness to the issue of missing and murdered indigenous women across Canada. 

As a man who ‘presents white’ (on account of his New Zealand-born father) but is also full status indigenous, Matthew is committed to lending privilege to bridge indigenous and non-indigenous communities, open the channels of communication, and raise this often ignored issue to the broader public agenda. 

“You never really know what you’re capable of until you apply yourself, I second-guessed myself every single day and even when I reached my final destination, I didn’t feel elated or done — this is just the beginning of my work and my journey.”

On October 14, 2017, Matthew’s aunt, Frances Brown, disappeared while mushroom picking in a forested area north of Smithers, BC. Local search and rescue crews from around the province were called in, alongside RCMP and volunteers — but the official search was called off eight days after it began. 

“If I were an indigenous woman, or even looked more like an indigenous man, then you probably wouldn’t be having this conversation with me,” Matthew said from North Sydney, Nova Scotia. “As you can imagine, it’s a privilege to be who I am, and I am using that as a tool to deliver our message.” 

Speaking in front of community groups, to the media, and most importantly, he says, to school-aged children, Matthew has been educating Canadians about residential schools, day schools, ‘the sixties scoop,’ and aboriginal child welfare — aspects of Canadian history that until recently had been brushed over in school curriculum. “Young people are this country’s future elders,” says Matthew. By educating them, he hopes they, in turn, can educate others. 

Matthew is a staunch advocate for women’s rights — both indigenous and non-indigenous women — and while he says his talks across the country were mostly attended by women, his goal is to have more men engaged in these conversations. “Women are sacred, they are life bringers, water carriers, and an integral part of our societies,” Matthew says. “I want to see more non-indigenous women stand up for indigenous women, and more men stand up for all women.” Matthew is also a supporter of the Moose Hide campaign, a grassroots movement of Indigenous and non-Indigenous men and boys who are standing up against violence towards women. 

While his walk proved excruciating at times, leading to physical injury, illness, and emotional trauma, Matthew says he realized a great deal about himself over the course of the year. “You never really know what you’re capable of until you apply yourself,” he says. “I second-guessed myself every single day and even when I reached my final destination, I didn’t feel elated or done — this is just the beginning of my work and my journey.”

A welder and carpenter by trade, Matthew continues to commit his time and energy to championing this cause. “While I was walking I was able to meet with tens of thousands of people across our nation, laying the groundwork for what I’m about to do next.” On June 1st, 2020, Matthew will be leading a sponsored bike ride from B.C. to Newfoundland, raising funds for all indigenous communities in Canada that have missing family members. “I’ve connected with many people over the past year and through this bike ride I get to test their commitment to really wanting change.” 

While Matthew was nearing the final leg of his journey, another Canadian man was just setting out on his own personal mission to lend a voice to those whose voices have traditionally been silenced.  

This past spring, multi-instrumentalist, singer-songwriter Jordan Hart completed a 100-day busking challenge — serenading strangers on the streets across Toronto to raise money and awareness for L’Arche Canada, an organization that creates communities for people with intellectual disabilities.

Jordan was born into a musical family and says that he spoke music before he could speak words. Graduating from an arts high school in Edmonton and having completed a summer program at the Berklee College of Music in Boston, Jordan chose busking as the route to musical fulfillment. In 2013, he set out to travel across North America as a busker, beginning in Vancouver. “Almost immediately I was connected with influential people in the industry, including producers, and I decided to stay and see where those connections would take me.” 

“You know, as humans, we have this preconceived notion about someone’s value based on their capabilities, which tend to revolve around money or talent.”

A few years later he followed his music and connections to Toronto, where he spent time in the studio with producer Michael Sonier (who has worked with Alessia Cara, Mary J Blige, and more) and the multi-platform, Grammy-nominated production/songwriting group Kuya Productions (their credits include Alessia Cara, Drake, and others), creating a five-song EP that blends acoustic, roots soul with alternative R&B. 

“I spent a lot of time in the studio and was ready to get back to the streets,” Jordan says. But rather than focusing on self-promotion, he took the opportunity to lend privilege to an organization and cause that was extremely close to his heart.  

“My dad was the executive director of L’Arche in Edmonton and has been on the board of L’Arche Canada for some time, and from a young age I was in touch with the community, spent time visiting houses, and had relationships with residents and assistants,” Jordan says. “What I experienced in those communities was inspiring and unique. I had never seen such unconditional love and acceptance in my life.”  

Jordan dedicated every Sunday of his 100-day challenge to L’Arche, raising funds, and more importantly, awareness. “What I felt I could really offer was exposure of L’Arche to a younger generation,” he says.  Jordan brought core members from L’Arche communities out with him to speak, dedicated his social media posts to the cause, spoke to the media, handed out information, and had one-on-one conversations with people who came to watch him perform.

The results were more than he could have ever imagined. “You know, as humans, we have this preconceived notion about someone’s value based on their capabilities, which tend to revolve around money or talent,” Jordan says. “And you look at someone with intellectual disabilities and they don’t possess these things and so they’re often overlooked. But when you sit down with them, you realize that value is not attached to that at all — what matters most is being in the moment and being human together. And, you realize that your worth actually never had anything to do with what you’re capable of. That understanding left a huge space in my heart to love myself for who I am — and a desire to share this realization with others.” 

What surprised and delighted Jordan most was how many young people he met while busking who wanted to learn more and get involved. “I’ll never forget the moment a young man came up to me, saying he’d moved to Toronto to pursue a job, and while he was doing well financially, and all his goals had been met, he was feeling unsatisfied. He needed to reconnect to community and he was drawn to what I was saying about L’Arche and wanted to know what he could do to help.” 

As Jordan continues his musical journey, he plans to continue to involve L’Arche directly. Next up is a showcase that will include music as well as other art forms. “I would like to have artists of all backgrounds collaborating to create a multi-sensory experience where you can feel the openness and inspiration to become who you are and celebrate that,” he says. The project is in the works now, with the aim to have it ready by late summer or early fall. 

While lending privilege certainly doesn’t have to be the grand gestures made by Jordan and Matthew, which are two completely different examples, it does require the realization that our privilege gives us benefits that others can’t easily access. It’s what you do with that realization — how you step into your power and use it to advance the voice, or the career, or the well-being of another person or group of people — that really matters. Whether that means making an introduction to someone in your network, bringing a junior employee into a meeting, or choosing to be a mentor or sponsor, there is likely a small action you can make immediately that will have a long-term impact on someone else’s life or career.