“Stephen Cloobeck’s book covers the life of a modern day business genius."

- Former US Senator Harry Reid

Stephen J. Cloobeck

A self-made business leader with over 30 years of experience across every aspect of hospitality design, development, and deployment. 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—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.

Photo of the book Checking In by Stephen J. Cloobeck
  • Photo of sticky note, written 'Dad, I love you so much. You taught me everything. Hugs. Kisses. Forever Your son.

    To my father, my best friend and hero. RIP.

    Contents


    Foreword
    ix
    Introduction
    1
    How This Book Is Structured
    15

    Part One

    1 Beginnings
    21
    2 Striking Out on My Own
    31
    3 The Sunterra Saga
    43
    4 Toward a Turnaround
    55

    Part Two

    The First Principle of Hospitality:Focus Unrelentingly on the Guest

    5 The Meaning of Yes
    67
    6 Be My Guest
    77

    Part Two (cont.)

    The Second Principle of Hospitality:Commit to Continuous Improvement

    7 From a Culture of No to the Meaning of Yes
    89

    The Third Principle of Hospitality:Prioritize Reputation over Brand

    8 Empower the Periphery
    97

    The Fourth Principle of Hospitality:Ensure Total Alignment

    9 Embracing a Collaborative Meritocracy
    111
    10 My Business Card on Every Front Desk
    123

    The Fifth Principle of Hospitality:Do Well by Doing Good

    11 Taking the Long View
    129

    Part Three

    12 Once an Entrepreneur, Always an Intrapreneur
    147
    13 Remaking Timeshare in Our Own Image
    155
    14 Seeking Inspiration from All Places
    165
    15 Going Undercover
    179
    16 Underneath the Tip of the Iceberg
    189
    17 Growing the Pie
    195
    18 Brand USA
    201

    Part Four

    19 We’re All in Hospitality Now
    221

    Acknowledgments
    235
    Notes
    237
    Index
    247
    About the Author
    257

    Introduction

    When I set out into this uncharted territory of writing a book, I asked an acquaintance of mine, who happens to be a three-time published author, for much-needed help.

    “I’m trying to write a book about the one piece of advice successful busi- ness leaders of tomorrow need to know. As a successful author, what’s the one tip you would give me about writing a book?”

    He didn’t hesitate. He didn’t waver.

    “You’ll never go wrong treating the reader as you, yourself, would like to be treated.”

    Well, future reader, if you’re anything like me, patience has never been a virtue.

    So let’s skip the pleasantries.

    Let’s skip the prologue.

    Let’s get right to brass tacks.

    I’ve spent my entire career, my entire life, in hospitality. You name it, I’ve done it. Back of house, front of house, running the whole house. At the risk of getting ahead of myself, the company I would ultimately found—Diamond Resorts International—today has a network of hundreds of vacation destina- tions on six continents: that’s covering the United States, Canada, Mexico, the Caribbean, South America, Central America, Europe, Asia, Australia, and Africa. In 2015, Diamond Resorts, which rose from the ashes of a pre- decessor nearly twice bankrupt, reported a healthy $954 million in revenue with a profit of, give or take, $150 million.1 As we go to print, Diamond Resorts International is among the largest timeshare resort companies in the world—competing with the likes of Marriott, RCI, and Hilton—and is poised to grow.

    Mine isn’t a rags-to-riches drama, but it is a true, practical, and instruc- tive story about what it takes to find business success on your terms—nobody else’s. My story is about what it takes to get ahead when everyone else is try- ing just to keep up, what it’s like to see your business and career dreams go from tangled confusion to clear vision to reality.

    True leadership is about taking a stand for the people, principles, and products you believe in. Leadership is hollow without ownership.

    It’s only right that I warn you now: I built my business by breaking all the traditional rules, and I plan to write my book the very same way. You’ll never hear me apologize for my successes or, for that matter, my failures, of which there are plenty. That’s because true leadership is about taking a stand for the people, principles, and, yes, products you believe in—not shirking from them. I’ve learned that leadership is hollow without ownership.

    I never saw myself writing a book of any kind, let alone a business book— and most certainly not a memoir. But I believe that sometimes we need to check in with ourselves, to figure out again what we’re about, where we want to go, and how best to get there. I believe when we take a good, hard look at who we are as people and what we have to offer, we can do something powerful that changes our personal and professional outcomes. So what follows in the ensuing pages aren’t watered-down stories, PC commentary, or self-help incantations. You won’t get that from me. What follows are the once-in-a-lifetime experiences, career-defining moments, and hard-earned lessons you get only by rolling up your sleeves, diving in, and never looking back. What follows are strategies and stories that will make you think and definitively change how you approach people, problems, and possibilities.


    To continue reading, please purchase a book below:

    CHECKING IN Stephen J. Cloobeck

“Stephen Cloobeck’s book covers the life of a modern day business genius. I’ve known him for decades, and he has never changed. He is cocky, self-assured, aggressive, arrogant, self-confident, and always focused. He’s not afraid to confront anyone (including me) when he feels it’s appropriate. But when all the brashness passes, and it does quickly, one sees a person with a social conscience, a person who is known for his generosity. Stephen Cloobeck is a good person, a creator of thousands of jobs, an innovator, and to many, a friend.”

– Former US Senator Harry Reid

“Stephen J. Cloobeck is the best in the business. he told me so himself.”

– Dr. Frank Luntz, political consultant, pollster, and communications expert

Stephen Cloobeck’s story shows that anything is possible when good leaders don’t just fight but strategically collaborate for deserving causes. It merits being told, studied, and, hopefully, replicated.

– Roger Down, president and CEO of the U.S. Travel Association

“Stephen Cloobeck’s book covers the life of a modern day business genius. I’ve known him for decades, and he has never changed. He is cocky, self-assured, aggressive, arrogant, self-confident, and always focused. He’s not afraid to confront anyone (including me) when he feels it’s appropriate. But when all the brashness passes, and it does quickly, one sees a person with a social conscience, a person who is known for his generosity. Stephen Cloobeck is a good person, a creator of thousands of jobs, an innovator, and to many, a friend.”

– Former US Senator Harry Reid

“Stephen J. Cloobeck is the best in the business. he told me so himself.”

– Dr. Frank Luntz, political consultant, pollster, and communications expert

Stephen Cloobeck’s story shows that anything is possible when good leaders don’t just fight but strategically collaborate for deserving causes. It merits being told, studied, and, hopefully, replicated.

– Roger Down, president and CEO of the U.S. Travel Association

“Stephen is a master communicator with a rare knack for understanding and working with individuals across a wide range of functions . . . (To get a sense of this, go watch him on Undercover Boss.) This is the secret sauce of Stephen’s success — and thereby the source of Diamond Resorts’ success. Stephen cares about his workers and empowers them to take ownership and pride in their efforts. He makes sure they find meaning in their work.”

-Michael Milken

“Whether you’re a business leader or emerging entrepreneur, there’s a lot of wisdom from Stephen Cloobeck about how to be successful.”

– Robert Shapiro, internationally renowned litigator and serial business entrepreneur

“I’ve learned invaluable business lessons from Stephen — most importantly, this unwavering belief in the Meaning of Yes. He created a groundbreaking and innovative 24/7 service culture that always places guests first. People across the globe are changed by these core values every day.”

– Mike Flaskey, current CEO of Diamond Resorts International

“Stephen is a master communicator with a rare knack for understanding and working with individuals across a wide range of functions . . . (To get a sense of this, go watch him on Undercover Boss.) This is the secret sauce of Stephen’s success — and thereby the source of Diamond Resorts’ success. Stephen cares about his workers and empowers them to take ownership and pride in their efforts. He makes sure they find meaning in their work.”

-Michael Milken

“Whether you’re a business leader or emerging entrepreneur, there’s a lot of wisdom from Stephen Cloobeck about how to be successful.”

– Robert Shapiro, internationally renowned litigator and serial business entrepreneur

“I’ve learned invaluable business lessons from Stephen — most importantly, this unwavering belief in the Meaning of Yes. He created a groundbreaking and innovative 24/7 service culture that always places guests first. People across the globe are changed by these core values every day.”

– Mike Flaskey, current CEO of Diamond Resorts International

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People First, Systems Second, and Hospitality Above All

People First, Systems Second, and Hospitality Above All Stephen J. Cloobeck’s The Meaning Of Yes Philosophy Has the Power To Change Customer Experiences And Businesses’ Bottom Lines Across Industries In CHECKING IN:...

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