Episode 26 – The Power of Philanthropy: Asking Tough Questions and Inspiring Change
Host: May Harris, Esq.
Guest: Ryan Ponsford
“Do something kind; your feelings will follow, and I think the biggest encouragement is to start somewhere and do something nice. I just try to give, and if you give, if that's the action, I think care, love, and empathy will be the outcome. Probably my biggest encouragement for people is to find a way to get started.”
- Ryan Ponsford
In This Episode
How courage, generosity, and hard conversations can transform boards, families, and communities.
Philanthropy isn’t just about money—it’s about asking the hard questions and inspiring others to give with purpose. In this episode, May Harris talks with Ryan Ponsford, founder of Main Street Philanthropy and co-founder of Gateway for Good, about how teaching generosity can prevent family disputes over wealth, build trust, and connect people across divides. From working with competing gang members to advising wealthy families, Ryan shares powerful stories that show the ripple effect of kindness, vision, and intentional giving.
Key Takeaways
Insightful moments and lessons from the conversation.
Why board members must engage fully and ask the uncomfortable questions.
How Main Street Philanthropy teaches kids to value giving and avoid conflict over wealth.
The role of philanthropy in fostering vision, trust, and communication.
Lessons from guiding both wealthy families and underserved communities.
Why generosity and empathy can start with small, intentional acts.
Guest Bio: Ryan Ponsford
Ryan Ponsford is the founder of Main Street Philanthropy and co-founder of Gateway for Good. With over 20 years in wealth management, he helps families navigate the complexities of wealth transition, philanthropy, and building meaningful legacies. Ryan’s work bridges the worlds of financial strategy and human connection, empowering clients to embrace generosity as a tool for growth and harmony. He’s also a serial entrepreneur and advocate for giving programs that inspire businesses, families, and communities to act with purpose.
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