Month: September 2026
Building an Enduring Business: Trust, Relationships, Financial Psychology & Long-Term Growth with Chris Bailey (Ep. 27)

Building an Enduring Business: Trust, Relationships, Financial Psychology & Long-Term Growth with Chris Bailey (Ep. 27)

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Building a successful business is one thing. Building one that endures for decades is another. In this episode of the Planning Perspectives Podcast, Jamie Hopkins and Kate Duffy sit down with Chris Bailey, Founder and CEO of Bailey Brand Consulting, to discuss the principles that have helped his firm thrive since 1985. From leadership and mentorship to brand strategy, client trust, and navigating technological change, Chris shares lessons learned from nearly four decades of helping organizations create lasting value.

Key Takeaways:

  • Why successful leaders balance short-term results with a long-term vision
  • How mentorship, trusted advisors, and strong relationships can guide critical business decisions
  • Why understanding your organization’s “why” is essential for sustained growth and culture
  • How trust, authenticity, and customer experience contribute to brand value and loyalty
  • What business leaders should consider as AI and technology reshape marketing and consumer expectations
  • Why bigger isn’t always better—and how deep client relationships can create a competitive advantage
  • How convenience and experience are influencing consumer behavior and business strategy today
  • And more.

Whether you’re a business owner, investor, or leader looking to build something that lasts, this conversation offers practical insights on growth, brand value, and creating an organization that stands the test of time.

Connect with Bryn Mawr Trust: 

Connect with Kate Duffy: 

Connect with Jamie Hopkins: 

Connect with Chris Bailey:

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How Psychology Influences Financial Decisions: Understanding the Emotional Side of Money (Ep. 26)

How Psychology Influences Financial Decisions: Understanding the Emotional Side of Money (Ep. 26)

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Your past experiences, emotions, beliefs, and mindset can have a powerful influence on how you spend, save, invest, and make financial decisions, even when the numbers seem straightforward.

In this episode, Jamie Hopkins and Kate Duffy explore the growing field of financial psychology, examining how emotions, behavioral patterns, and money beliefs shape financial decision-making. They discuss the lasting impact of childhood experiences, scarcity mindset, spending habits, and unconscious money scripts on financial behavior. The conversation also explores why financial education alone often isn’t enough to change behavior, how intentional spending can align money with personal values and goals, and why self-awareness is critical for making better financial choices before emotions take over.

Key points:

  • How financial psychology connects thoughts, emotions, beliefs, and past experiences with everyday money decisions
  • Why knowing the financially appropriate choice doesn’t necessarily mean you’ll feel ready to follow through with it
  • How childhood money experiences can continue shaping spending, saving, debt, and feelings of scarcity later in life

Resources:

Connect with Bryn Mawr Trust: 

Connect with Kate Duffy: 

Connect with Jamie Hopkins: 

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

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

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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.

Kenny discusses:

  • 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: 

Connect with Kate Duffy: 

Connect with Jamie Hopkins: 

Connect with Kenny Holdsman: 

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.

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