The Giving Games: A new chapter in thoughtful philanthropy
Canada Gives is about to welcome our Foundation families to an entirely new experience—one designed not around fundraising, but around learning, connection and the craft of giving well. With Prime Quadrant as our presenting sponsor, we’re proud to host the first annual Giving Games, an invitational gathering that brings together thoughtful donors, experienced philanthropists and transformative charities.
At its core, the Giving Games—to be held at the Art Gallery of Ontario on May 28th, 2026—reflects a simple but powerful idea: that philanthropy isn’t just about writing cheques, but rather about making informed and intentional decisions that create meaningful impact by aligning funding interests with measurable outcomes.
Why the Giving Games was established
Canada Gives was built on the belief that Donor Advised Fund (DAF) donors deserve the same level of philanthropic service, engagement and impact as philanthropists who maintain successful private foundations. For many families, that means striving to go beyond transactional giving and embracing a more strategic, informed approach.
As our Founder and CEO Denise Castonguay explains, “We’re committed to empowering our donor clients to make giving decisions that align with their core values and advance the aims of their preferred charities. That means equipping them with the knowledge, tools and perspective needed to achieve real impact.”
The Giving Games is a natural extension of that commitment. It’s designed to demystify how experienced philanthropic families operate, including the tactics they use to evaluate opportunities, build relationships with charities and ultimately decide where to allocate capital.
Many Canada Gives Foundation families have told us they want to learn from others: What questions should they be asking of prospective grant recipients? What does a strong charity partnership look like? How do multi-generational families sustain impact over time?
This event will provide those answers—and more.
Learning from those who’ve done philanthropy well
A defining feature of the Giving Games is the opportunity to hear directly from seasoned philanthropists—individuals and families who have spent years refining their approach to giving. Through candid panel discussions, attendees will gain insight into how these donors think, what they prioritize and how they assess impact before making funding decisions.
“This is really about education and sharing a wonderful evening of philanthropic insight at a premiere venue,” says Castonguay.
This level of access is rare. While it’s one thing to read about philanthropy, it’s another to sit at the table with those actively shaping it. Some of those seasoned philanthropists include business executive and philanthropist Christina Sorbara, Mattamy Asset Management board member Luke Gilgan, Gerson Lehrman Group co-founder Mark Gerson and Crysalia Inc. executive chair Patricia Saputo.
From observation to action
What sets the Giving Games apart is that it doesn’t stop at discussion. It brings philanthropy to life in real time.
Six carefully selected charities will each present innovative solutions to pressing challenges in a concise, “Dragon’s Den”-style format. Each will have just five minutes to make their case. From there, the room becomes part of the process.
Through guided, interactive dialogue at each table, participants will engage in the same kind of conversations that happen inside leading foundations: debating merit, assessing impact and weighing priorities. Together, the room will determine how funding is allocated.
The total contribution will be generated through event participation, reinforcing the idea that philanthropy can be both collaborative and immediate.
Building connection
Many philanthropic families operate in relative isolation, without ready access to peers who share similar goals or levels of commitment. The Giving Games is designed to change that by bringing together a community of like-minded funders in an environment that encourages conversation, curiosity and collaboration.
“Our Foundation families want to spend time with others who care deeply about giving,” Castonguay notes. “This is an opportunity to learn from each other, to exchange ideas and to build relationships that extend beyond a single evening.”
Prime Quadrant is an organization known for hosting exceptional gatherings for ultra-high-net-worth families, and with their support as presenting sponsor, we’re ensuring that the experience reflects the calibre and expectations of our community.
A philanthropic learning experience
It’s important to be clear about what the Giving Games is not. This is not a fundraising gala. There are no auctions, no appeals and no pressure to give beyond participation. Instead, the focus is on education, insight and shared experience. It’s about understanding how to give—not just how much to give.
For families who are beginning to think more intentionally about their philanthropy, or those looking to refine an already established approach, this distinction matters. It creates space to explore, to ask questions and to engage without expectation.
The beginning of an annual tradition
The May 28th event marks the first of what we intend to become a cornerstone of the Canada Gives calendar. Our vision is to build the Giving Games into an annual gathering—one that evolves each year while staying true to its purpose of advancing thoughtful philanthropy.
Ultimately, the Giving Games is about more than a single evening. It’s about shaping how our community approaches giving over the long term.
For those who attend, the benefit will be both immediate and lasting. Our Foundation families will leave with practical insights, new connections and a deeper understanding of what it means to be philanthropic with intention and sophistication. But perhaps more importantly, they’ll experience something that’s often missing in philanthropy: the opportunity to learn by doing, alongside others who share their commitment to making a difference.
We look forward to welcoming you to the first Giving Games—and to building this tradition together.
The Canada Gives Team
To explore how a DAF might help you build a legacy that reflects your charitable values, consider opening a Foundation account with Canada Gives. Our team is here to help guide your charitable giving with flexibility and foresight. To learn more, contact a member of our team.
