For Moez Kassam, who co-founded the Moez and Marissa Kassam Equity Fund, which to date has donated $1 million CAD to Michael Garron Hospital and $5 million CAD to the School of Medicine at Toronto Metropolitan University, the purpose of philanthropy is simple: it’s about making cities and communities more equitable.

“I’ve always found it interesting that a lot of people look at their own business from an investment model, but they move over to philanthropy [and] look at it as charity [or] just sort of ‘giving it away,’” says Kassam, a Toronto-based hedge fund manager. “They are not looking at it through the same lens where you’re looking at deliverables and a return on investment.” 

The Kassams’ approach to philanthropy encompasses sustained investments in community fridges, food banks, and shelters supporting women recovering from trauma, alongside significant one-time contributions to institutions such as universities and hospitals. In 2024, the couple made a “landmark” $5 million CAD investment in the Toronto Metropolitan University School of Medicine specifically to fund scholarships for students from underrepresented communities, and earlier this year gave a transformative $15 million CAD gift to SickKids hospital.

For the Kassams, that means approaching philanthropy from a different, more collaborative, civic-minded model. “I’m on the board of the Toronto Foundation for Student Success, the charitable arm of the TDSB, and they do after-school programs and the Inner City Student Nutrition Program.” These initiatives aren’t scattershot acts of giving, they’re targeted, data-driven responses based on indicators like the Learning Opportunities Index, which identifies schools in the lowest income brackets. “We’ve been focused on making sure that every child isn’t hungry, because if you’re hungry, you’re not learning. And if you’re hungry, you’re more likely to get sick. The trickle effect that has on our society is massive,” he says. What makes this approach different is that it sees philanthropy as a complement to public infrastructure, rather than a replacement. 

“I think we’re looking at alleviating the poverty line,” Marissa says. “It’s not up to the government. They don’t have the capacity to do everything. As the gap between the rich and the poor becomes larger, it’s the upper echelon of affluence that should join the government on such initiatives to make our city more equitable.” 

Philanthropists like the Kassams represent a significant shift in the world of charitable giving over the past decade, with more high-net-worth individuals from diverse communities designing new private foundations for community upliftment based on their own unique lived experiences. A 2022 report from the Dorothy A. Johnson Center for Philanthropy found an increase in community-centered philanthropic models from donors of colour, which included incorporating cultural practices like giving circles and household giving to foster change at a grassroots level. 

A few factors differentiate this new approach to funding and charities from the traditional philanthropic sector. Rather than a charity attempting to solve a problem with a blank cheque, the focus lies in philanthropists honing in on a direct connection they have to a particular cause, and then allocating funding as a form of investing back into the larger community. The approach highlights the core principles of trust-based philanthropy, an approach pioneered by the now-defunct Whitman Institute, which shifts power dynamics in giving by prioritizing deep relationships, active listening and long-term, unrestricted support. 

These investments take the form of direct grants to nonprofits prioritizing what a community has shared publicly or shown that they need. ThriveFunds, an American organization founded by Gisele Garraway, uses community-driven resource delivery to alleviate the gaps in low-income households. A graduate of Harvard Business School who has held strategic executive leadership positions at Sephora and Staples, Garraway has structured Thrive to operate akin to mutual aid, enabling donors to directly support working parents with pressing needs or young adults navigating transitional periods, which may include everything from funding a year of childcare or providing an Uber voucher to cover transportation to urgent medical appointments.

“The more that we can educate folks who are fortunate about the real struggles that low-income workers are experiencing, the more that people [can] understand that it’s not that folks who are living paycheck to paycheck are being frivolous,” says Garraway. “Instead, there’s an understanding that if I’m spending 60 per cent of my income on housing and then another 25 to 30 per cent on food, that doesn’t leave much for transportation, technology, childcare and these things that are basic requirements to participate in our economy.”

Philanthropic models that prioritize resource sharing and economic mobility are defining points for philanthropists of colour. As outlined in the Pepperdine University dissertation by Janae Asali Oliver “Racialized Lived Experience and Equitable Decision-Making Among Philanthropic Leaders,” this group of funders are more likely to shift power “by transferring wealth and resources and dismantling the gatekeeping of foundations.” 

A 2017 report by the Donors of Color Network cited 1.3 million Americans of colour–including  African-American, Asian and Hispanic individuals–with a net worth of over $1 million CAD. Meanwhile, the Dorothy A. Johnson Center for Philanthropy predicts in a 2025 report that collective giving is expected to double in the next five years. The surge of philanthropic giving in communities of colour is speeding up, not slowing down. 

“I think that starting from that place of generosity and humility—as a heritage and cultural lineage—is one of the key differences between how the philanthropy sector talks about giving and how a lot of donors of colour think about their own personal giving,” says Isabelle Leighton, executive director of the Donors of Color Network, self-described as a cross-racial network of high net wealth donors who are using their power to advance racial justice.

Leighton says that philanthropy can play a role in upholding political and civil freedoms if donors keep their ear to the ground for success stories and strategically invest in the impactful work happening on the ground. “We can’t choose between democracy or racial justice,” says Leighton.

This means going beyond large, tentpole charities and identifying those who need material support at the foundational level of political organizing. “Instead of thinking about long-term, sustainable investment, the philanthropy sector has this way of picking and choosing who are the ‘so-called winners’ during an election cycle,” says Leighton.“These individuals and leaders of colour are already here doing great work. All we need to do is fund them.”

It’s why the network is devoted to projects that deliver grants to grassroots networks and work on a wide range of initiatives, ranging from knocking on doors to get the vote, to supporting disaster management efforts and engaging in political advocacy. This mode of collective giving not only dismantles the gatekeeping that occurs in the traditional philanthropic sector, by looking beyond intermediary institutions, but also interrogates the idea of who gets to be titled as a philanthropist. 

That is something Isaac Olowolafe Jr. has seen in his own philanthropic work. An award-winning real estate broker, entrepreneur and angel investor who moved to Canada from Nigeria as a child, he remembers seeing “how certain communities thrive or don’t thrive in Canada” as a child. So, when he got his real estate license at 21, he quickly made a commitment to level the playing field for his community.

In 2010, he established the largest fund for an African studies scholarship at the University of Toronto. Six years later, he started the Dream Legacy Foundation with a $2 million CAD endowment, which supports the Dream Maker Realty Digital Media Experience Lab, a critical access point for student entrepreneurs to access the digital library at Toronto Metropolitan University. 

But his goal is not only to help his community.

“Our goal is to change the narrative of philanthropy,” he says. “Not only from how to do it, but how to start and how to be more strategic about it and more hands-on as well.”