In the debut episode of our PhilanthroThink Podcast series, hosts Megan Skyvington and Daniel H. Lanteigne sit with Linsey Sherman-Zekulin, a dynamic nonprofit leader, philanthropist and co-founder of Happy Roots Foundation, a private charitable foundation in Ottawa, and Sororal, a femme-focused travel and advocacy brand. At Happy Roots, Linsey is championing a trust-based approach to philanthropy and grant-making, something she discusses in Episode 1. You can find it below or on YouTube, Apple Podcasts or Spotify.
Rethinking Trust-Based Philanthropy: A Conversation with Linsey Sherman-Zekulin
At the start of the interview, the hosts ask Linsey to share her journey into philanthropy and the key experiences that shaped her approach. She explains that the transition into philanthropy became more personal in 2019, when a shift in her family’s circumstances—and an entrepreneurial spark from her husband—paved the way for founding Happy Roots Foundation. This private charitable foundation is dedicated to a trust-based approach to grant-making, especially in the realm of infant and early childhood mental health. Linsey explains that by choosing this focus, she was able to connect her professional passions with her desire to make a tangible difference in the community.
She also highlights the importance of being flexible in her approach. Rather than relying on lengthy reports, Linsey says she prefers regular, informal conversations with her partners, which allows them to adjust their strategies in real-time. This approach not only builds stronger relationships but also ensures that the funding makes an impact.
At the end of the discussion, we understand that trust is at the centre of the foundation’s work, as it gives grantees the room to do what they do best—help others.
“We have really embraced the idea of trust-based philanthropy being underpinned by collaboration and relationship building… It’s about getting to know each other from the very beginning,” Linsey said. “And I think this is one of the pieces of a trust-based philanthropic approach where we are respectful of the work and the expertise and the role that the leaders in the organization have…”
Linsey also discusses navigating respectively and thoughtfully the philanthropic landscape, knowing that there has been a longstanding power dynamic between funders and recipients.
“I feel strongly that our traditional models of philanthropy and funder — and grantmaker and grantee — are rooted in a lot of institutional power imbalances,” Lindsey explains. “And I think a lot about whether I’m contributing to it, and how can I not contribute to it. Even when I think I’m not contributing to it, am I contributing to it?”
The conversation later touches on the entrepreneurial elements of her Foundation’s work: “I do think there is something entrepreneurial about it. And I never considered myself particularly entrepreneurial, although, in the last couple of years, I’ve sort of dipped my toe into entrepreneurial life and learned a lot about it. And there are some really exciting things that come about when you kind of embrace that mindset.”
Lindsey also says that she hopes more people embrace the entrepreneurial spirit, particularly when considering higher-risk projects to support. With that mindset, there’s an opportunity to take risks in solving complex problems that might otherwise not be solved.
Thank you to IG Private Wealth Management for a grant to make the PhilanthroThink Podcast series possible.
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Monday, March 24, 2025 in News, PhilanthroTHINK, Podcast
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