20 SEP 2026 · Barry Jacobson once ironed Bob Iger's shirt.
He also started out as a lifeguard, held nearly 30 different roles, and spent 37 years inside The Walt Disney Company. In this episode of Amplify Hope Today with Simon T. Bailey, Barry shares the behind-the-scenes leadership and customer service principles that created Disney magic — and how any leader, in any organization, can put them to work.
A paycheck is given to people who show up. Opportunities are given to individuals who think and work beyond what they're paid to do. — Simon T. BaileyBarry's most powerful lesson is also his strangest: be a schlepper.
For Barry, being a schlepper means being willing to help, serve, connect, and do the work others overlook. It meant volunteering in housekeeping as a young lifeguard. It meant getting coffee for an executive. It meant ironing Bob Iger's shirt and finding a way to fulfill an unexpected guest request. Over 37 years, Barry learned that service creates visibility — and visibility creates opportunity.
He also explains why great customer experience always starts with employee experience, why leaders should "solve for yes" instead of defaulting to no, and how Disney's philosophy of "plussing" turns an ordinary interaction into a moment a guest never forgets.
Along the way, you'll hear stories from working around Disney executives, launching experiences around the world, serving Disney's passionate D23 fan community, and leading experiences at Golden Oak. Barry shares lessons from his work beyond Disney as well, including the Dallas Cowboys and other major hospitality brands, and explains why clear standards, empowered employees, real training, and a shared sense of purpose are what make a brand experience consistent.
In this conversation, you'll learn:
- Disney leadership lessons drawn from a 37-year career
- How to create exceptional customer experiences
- Why employee experience drives customer loyalty
- How leaders build a culture of care
- Why listening is one of the most important leadership skills
- How "plussing" creates surprise-and-delight moments
- Why working beyond your job description accelerates career growth
- How to "solve for yes" instead of defaulting to no
- Why relationships remain at the heart of great organizations
- How small, personalized gestures create lifelong customers
If you're a leader, entrepreneur, hospitality professional, customer experience professional, or anyone who wants to stand out in your career, this conversation is packed with lessons you can put into action immediately.
Coming soon: Simon's new book, Amplify Hope: Lead From Where You Are Standing. Barry's story is a living example of its central idea — that leadership isn't a title you wait to receive. It's something you practice from wherever you're standing right now.
Subscribe to Amplify Hope Today with Simon T. Bailey for conversations about leadership, personal growth, purpose, service, and becoming an amplifier in the lives of others.
-----------------------------------------------------
Watch full episodes on YouTube:
http://www.youtube.com/@AmplifyHopeTodayShow
Listen on Apple Podcasts: https://podcasts.apple.com/us/podcast/amplify-hope-today/id1881115485?i=1000752112808
Listen on Spotify: https://open.spotify.com/show/1OJS29kGxgcYTJnzZCoehb?si=b36e8692245b4551
STAY CONNECTED
Follow Simon at:
Website: https://www.simontbailey.com/
Instagram: @SimonTBailey
LinkedIn: http://linkedin.com/in/simontbailey
Follow our podcast at:
Website: https://www.amplifyhopetoday.com/
Instagram: @AmplifyHopeToday
-----------------------------------------------------
Special thanks to our partners: Hi Hello Labs in Orlando, Florida, for powering and producing this show.
Sponsored by: Hi Hello Labs Produced at: Hi Hello Labs Learn More: https://www.amplifyhopetoday.com/