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Building Futures Beyond Sports: A Conversation with Kenny Holdsman (Ep. 25)

Jamie Hopkins, Esq., LLM, CFP®, ChFC®, CLU®, RICP®

Bryn Mawr Trust
Bryn Mawr Trust Advisors

Kate Duffy, FBS^®, MFP

Bryn Mawr Trust Advisors

September 2, 2026

2 min read

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On this week’s episode of the Planning Perspectives Podcast, Jamie Hopkins and Kate Duffy welcome Kenny Holdsman, co-founder, president, and CEO of Philadelphia Youth Basketball, for a conversation about purpose-driven leadership, career transitions, and creating opportunities for the next generation.

After a successful legal career, Kenny followed a new path centered on youth development, education, and community impact. He shares how Philadelphia Youth Basketball has evolved into an organization that supports young people both on and off the court through mentorship, wellness initiatives, financial literacy, academic support, and career development.

In this episode, you’ll learn:

How aligning your skills and values can lead to more meaningful work
Why investing in the whole person is key to long-term success
How community partnerships can create lasting opportunities for young people
Leadership lessons on building trust, purpose, and impact-driven organizations

Jamie Hopkins, Esq., LLM, CFP®, ChFC®, CLU®, RICP®

Bryn Mawr Trust
Bryn Mawr Trust Advisors

Jamie Hopkins oversees the private wealth management group’s financial advice strategies and growth initiatives, along with leading the institutional and personal trust businesses. He joined the company in 2023.

Kate Duffy, FBS^®, MFP

Bryn Mawr Trust Advisors

Kate Duffy collaborates with clients to provide wealth management strategies, financial planning, and investment advice. She joined the company in 2024.

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