What happens when a successful career no longer aligns with your values, strengths, and sense of purpose? Many professionals reach a point where they rethink how they want to make an impact and what meaningful work looks like.

In this episode, Jamie Hopkins and Kate Duffy sit down with Kenny Holdsman, co-founder, president, and CEO of Philadelphia Youth Basketball (PYB), to discuss career transitions, purpose-driven leadership, and youth development. Kenny shares his journey from practicing law to leading a community-focused organization, and how Philadelphia Youth Basketball uses sports as a gateway to mentorship, education, and opportunity.

• How a career transition helped align his skills, values, and purpose
• Why youth development requires mentorship, education, wellness, and career readiness
• How Philadelphia Youth Basketball built a community-centered model for impact
• The importance of trust and strong community partnerships
• How long-term planning can expand opportunities for future generations

Connect with Bryn Mawr Trust:

• 833-973-7633
• LinkedIn: Bryn Mawr Trust
• Website: Bryn Mawr Trust

Connect with Kate Duffy:

• LinkedIn: Kate Duffy

Connect with Jamie Hopkins:

• LinkedIn: Jamie Hopkins

Connect with Kenny Holdsman:

• LinkedIn: Kenny Holdsman
• Website: Philadelphia Youth Basketball

About our Guest:

Kenny Holdsman is the co-founder, president, and CEO of Philadelphia Youth Basketball, where he helps young people build brighter futures through mentorship, education, wellness, and career preparation. A former attorney at Ballard Spahr, Kenny shifted from law to youth development to pursue more purpose-driven work. His focus is on expanding opportunities for young people, strengthening community partnerships, and creating lasting impact across Philadelphia.