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The Pivotal Leader

The Pivotal Leader podcast, hosted by Gina Trimarco, Chief Results Officer of Pivot10 Results, features 30-minute interviews with modern and pivotal business leaders who share their experiences and anecdotal success stories to inspire rising leaders to shift their own organizational cultures to higher success.
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Oct 21, 2018

"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 – 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.

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.

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

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