Leading with Vulnerability: Sobriety, Strength, and Service with Jeff Boland

In this episode of Hospitality Bites, host Colleen Silk sits down with Jeff Boland, a hospitality leader whose story of addiction, recovery, and reinvention is both powerful and deeply human. Jeff shares how his journey through sobriety has shaped his leadership style, inspired his writing, and strengthened his advocacy within and beyond the industry.

From managing multi-unit operations to authoring a book rooted in personal and professional lessons, Jeff emphasizes the importance of vulnerability, communication, and empathy in creating workplaces where people truly feel seen. He also opens up about his involvement with the Isabella Santos Foundation, where his mission to serve others continues in new and meaningful ways.

This episode is a candid look at what it means to lead with heart in hospitality — meeting people where they are, and using our stories to build stronger, more supportive communities.

Takeaways

• Addiction is a mental health challenge similar to anxiety or depression.
• Sobriety thrives with ongoing support, honesty, and community.
• True leadership means meeting people where they are and seeing their potential.
• Vulnerability and openness can inspire others and build trust in the workplace.
• Effective communication is the foundation of successful management.
• Creating a supportive environment enhances employee well-being and retention.
• Jeff’s upcoming book blends lived experiences with actionable leadership lessons.
• The Isabella Santos Foundation fuels hope for families through pediatric cancer research and community events.
• Jeff’s management philosophy includes a three-part audit system centered on accountability, empathy, and growth.
• Vulnerability in leadership builds meaningful, lasting connections.

Chapters

00:00 — Introduction

03:15 — From Addiction to Advocacy

10:42 — The Power of Sobriety and Support

18:50 — Leadership Through Vulnerability

27:20 — The Writing Process and Lessons from the Field

34:05 — Giving Back: The Isabella Santos Foundation

41:00 — Building Supportive Environments in Hospitality

47:30 — Final Thoughts and Words of Encouragement

Listen + Connect

Hosted by Colleen Silk, Hospitality Bites is an honest and restorative space for voices within the hospitality industry. More than just a podcast, it’s a storytelling platform for changemakers, risk-takers, and hospitality professionals redefining what it means to serve.

New episodes drop every Monday, proudly under the Walk-In Talk Media umbrella.

Watch the full episode on YouTube the following week.

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