Episode 79: Every Industry Is In Hospitality with Stephen J. Cloobeck, Diamond Resorts International Founder

the pivotal leader gina trimarco pivot10 results

“Get up early. Stay late. Do what your passion is. And don’t be afraid of taking risks.

Stephen J. Cloobeck

On this episode of The Pivotal Leader, Gina Trimarco interviewed Stephen J. Cloobeck, a self-made entrepreneur with more than thirty years’ experience across every aspect of hospitality design, development, and deployment … AND author of the new book CHECKING IN:  Hospitality-Driven Thinking, Business, And You.

As the original founder and former CEO and chairman of Diamond Resorts International (NYSE:DRII) – a business that grew to become the second-largest vacation-ownership company worldwide with more than four hundred properties across thirty-three countries in its portfolio – Cloobeck made a name for himself as the industry’s most adamant advocate for radical customer service, what he calls embracing the Meaning of Yes.

But to Cloobeck’s own amusement, he is perhaps most frequently recognized for his appearances on CBS’s hit TV show Undercover Boss. Featured on multiple episodes across multiple seasons, Cloobeck to this day ranks as the “most generous boss” who has ever participated in the unscripted program.

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Podcast Topics Include:

  • How the five biggest companies are hospitality companies
  • The meaning of “A culture of no is a culture of losing” and “Leadership is hollow without ownership”
  • Delivering “the meaning of yes”
  • Be an accessible and approachable leader to customers and employees by making your personal contact info available
  • Passion as the root of success
  • Complacency emanates from the top
  • Communication, Collaboration and no Stagnation
  • Stephen’s experience partnering with Bill Marriott
  • Overcoming dyslexia
  • Advice for how best to connect with others
  • Work ethic: the old-fashioned way of working hard and “no free lunch”
  • Advice for scaling a business

More About Gina Trimarco

More About Pivot10 Results

More About Stephen J. Cloobeck

For his commitment to serving the hospitality industry and amplifying its economic impact nationwide, Cloobeck was appointed by Commerce Secretary Gary Locke to serve as the inaugural chairman of the board in Brand USA Inc., a US government-formed nonprofit corporation with the sole mission of promoting travel to the United States. As Brand USA’s leading voice, Cloobeck coordinated with the Department of Homeland Security, the Department of State, the Department of Commerce, Congress, the White House, and leading American business in a first-ever effort to efficiently, effectively, and economically make the United States a more welcoming and accessible international travel destination for millions of would-be visitors around the globe.


The Pivotal Leader is a production of Pivot10 Results, a strategy and training company that helps businesses shift from people problems to performance results.

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About the author

Gina Trimarco is a native of Chicago and CEO/Founder of Pivot10 Results and Carolina Improv Company. She has 25+ years of experience in marketing, sales, operations and people training. Gina combines street smarts and improv comedy skills with her experience in the corporate and entrepreneurial worlds, which sets her apart from her competition.

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