AI In Marketing

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

By The Planning Perspectives Podcast | September 30, 2026

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: