Checking In: Hospitality-Driven Thinking, Business, and You

Checking In: Hospitality-Driven Thinking, Business, and You

by Stephen J. Cloobeck


Members save with free shipping everyday! 
See details


It’s time to check in.
When’s the last time you checked in? No, not at a hotel. When’s the last time you checked in with your own goals, plans, and aspirations for the future?

In Checking In, Stephen J. Cloobeck—entrepreneur, investor, philanthropist, and the founder and former CEO and chairman of Diamond Resorts International—invites you to check in with yourself to take stock of where you are, where you want to go, and, most importantly, how to actually get there. 

Drawing from the hotel, accommodation, and travel worlds in which he built his success, Cloobeck shares one-of-a-kind business experiences and life lessons, demonstrating how a radical customer service mindset—what he calls the Meaning of Yes—can substantively change both personal and professional outcomes.

Make no mistake—this is straight-talk from one of the best. Cloobeck may be known for being tough, opinionated, and unabashedly competitive, but he’s also developed a philosophy of hospitality-driven thinking relevant to anyone looking to find success on their terms. Part strategy directive, part leadership coaching, part memoir, Checking In will change how you approach people, problems, and possibilities.

​Written for everyone who wants more out of life, Checking In calls you to view the world through the lens of hospitality-driven thinking, to make the most out of opportunities others miss, to take well-placed bets on yourself, and to say “yes” to the right risks at the right time. These are the practical business insights and all-too-real anecdotes you didn’t know you needed from a source you’d never expect.

Product Details

ISBN-13: 9781626345522
Publisher: Greenleaf Book Group Press
Publication date: 10/16/2018
Sales rank: 502,685
Product dimensions: 6.30(w) x 9.10(h) x 1.10(d)

About the Author

Stephen J. Cloobeck is a self-made entrepreneur 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.

Read an Excerpt



Like many American families, mine came from humble roots. My grandfather, Jacob "Itchkie" Cloobeck, came from Belarus to settle in Chicago in the early 1900s with nothing in his pockets, no money to his name, no acquaintances or relatives to call on. He did carry with him the American dream: an aspiration to fashion a better life for himself, his family, and his posterity by going as far as his talents would take him.

It's a common story, but I wonder today if it's one we still believe as a country. We should. Our shared faith in the idea of the American dream is what makes it possible in the first place.

Itchkie's Chicago was the stuff of legend: Factories mixed with crowded tenant housing, squalor alongside resplendent wealth, seas of people from every corner of the world going in every direction. He made ends meet by selling vegetables and fruit from a cart to local households and workers. Personable, persevering, and known for his sonorant voice that called housewives from their kitchens, the neighborhood dubbed him "the watermelon king of Chicago." Soon his hand-pushed cart flourished into a full-fledged produce business.

I start my story with Itchkie's because hearing his was my first exposure to the idea that life is what you make it. He came with nothing, and against the backdrop of 1920s Chicago — which itself was rapidly transforming from a regional trading outpost in the heartland of the United States into one of the country's largest cities1 — built a business his family would be proud of. I know I certainly am.

When I was six, my father clipped our family from its Chicago beginnings and moved us to a neighborhood located in the San Fernando Valley's outer suburbs of Los Angeles, California. (I blame the move for my everlasting aversion to temperatures that dip below fifty degrees.) My father had made a career for himself in real estate with a company by the name of World Leisure Time. He may have been in a different industry, but he still carried Itchkie's entrepreneurial streak. As a partner with the firm, he helped the company develop a revolutionary product for the time: land lots for sale.

In our family, listening to the ads that blasted the radio and television airwaves about these dream lots was a daily ritual at the time. This was always accompanied by a smile of pride from my father, no matter how hard he tried to keep a straight face. From hearing about Itchkie to watching my father, I came to equate work with pride, and pride with work. Yes, it was clearly a means of providing, but it was also a source of internal dignity and happiness for them both.

And so, ignoring child labor laws, I started my first job at the age of eight. I became a busboy at Brooktrails Lodge, one of my father's properties.

My First Job

These summers were some of the fondest of my childhood. I always went to the kitchen early to hear the older waiters and cooks talk among themselves — about yesterday's work, about their personal lives, about anything at all. Maybe it was because I was the boss's son, but they never chided me. Instead, they included me. In listening to their chatter, I felt part of a team, part of a purpose, and part of something bigger than myself.

Anyone who's ever worked in a kitchen knows just how chaotic back-of-the-house operations can be: the roaring stovetops, the billowing smoke, the rapid chopping of knives, the swarming of impatient staff trying to satiate the even more impatient customers. That I was not only holding my own but also contributing to this nonstop operation made me feel like I had figured out the world of adults. When I was clearing plates and washing dishes, I wasn't a kid; I was an important part of the crew.

Maybe it was the sense of involvement, maybe it was the treats the cooks would sneak me every so often, or maybe it was the paycheck that made me swell with self-esteem every two weeks. Regardless, I realized I loved working and earning my own way.

I can't reminisce over Brooktrails and not mention Lucille. Lucille was a powerhouse of a woman who commanded the restaurant's kitchen with unquestionable authority and unmatched know-how. Somehow, even as she was already overworked, dishing out instructions to her staff, supervising the quality of the cooking, and managing inventory, she found time to take me under her wing. With her diligent, patient help, I mastered the art — and it truly is an art — of perfectly fried bacon and lighter-than-air pancakes.

But Lucille taught me more than cooking. Through her example, she taught me that a true leader makes others feel welcome, not wary. She built people up and in so doing made her team better than just the sum of its parts. It's a lesson that has stuck with me for decades and has become a central component of the Meaning of Yes.

Summer after summer, through middle school and high school, I returned to Brooktrails Lodge — as a dishwasher, as an assistant cook, as a maintenance worker, as housekeeping staff. There was nothing I wouldn't do. And this, in retrospect, was the most valuable education I ever received.

What School Taught Me

By the fall of 1979, I was off to college. After a year at USC, I transferred to Brandeis University in Boston, which only confirmed my suspicions that I have no appreciation for the cold. A good Jewish boy from a good Jewish middle-class family, I knew that now it was time to choose a life for myself. I had all of three options: (1) become a rabbi, (2) become a lawyer, or (3) become a doctor.

I declared premed.

Brandeis was, and continues to be, a fine liberal arts institution with a theological bent. Approximately 80 percent of my peers were Jewish social science majors: history, the humanities, literature, language, political science. As I recall, there were little to no business offerings, but its budding science program held promise. At the time, Brandeis boasted an 83 percent admittance rate to medical schools — not a detail to be overlooked.

My head was down and my nose buried deep in biology and chemistry textbooks. But no matter how hard I studied or how much I read, my grades hit a hard ceiling I could not break through: At my very best, my academic performance was mediocre.

Here's my senior year transcript to prove it.

In fact, the marks shown here are admittedly inflated. I remember honing my negotiation skills by visiting professors after hours, persuading them to alter my Ds to C minuses, my C minuses to Cs, and so on. This is not a system I would recommend to any students perusing these pages today; but for me, it was enough to scrape by.

I graduated in 1983, never truly content with the idea that my potential was captured by my academic performance. Years later, I would receive a clarifying diagnosis. Despite completing a full K–12 education and four years of college training, it turns out I had been dyslexic the entire time.

I never once suspected.


I had one professor in college who did me a great favor: She never mistook test scores for capability. She was none other than Margret Rey, coauthor of the Curious George children's books. True to her main character's moniker, Professor Rey applauded curiosity, not rote learning; problem solving, not prerequisites. She had a supremely uncanny knack for fascinating students with her lectures, which always felt more like stories you wanted to listen to and be enraptured by than lesson periods you had to attend. She was an author, after all, and made her points by illustration, not declaration.

If there was one moral to Margret Rey's work, it was this: When you encounter a problem, which we all do from time to time, you address it, you assess it, and then you act on it.

To this day, I credit Professor Rey for teaching me how to think about problems, choices, and life. She impacted the way I would later go on to approach situations and engage with others. I wonder how differently my career would have gone had I not learned this lesson early on. And so I pass this on to you.


My premed direction meant finding appropriate apprenticeships to complement my coursework. To be close to family, I spent summers in California, interning at a Cedars-Sinai research facility, assisting with endocrinological programs and tests. Again, I was part of a team, doing significant work that held the promise of real-world importance and impact. The equipment may have been a bit pricier and the food hall less appetizing, but, in a way, I felt like I was back in the kitchen.

Like any good doctor-in-training, I spent time in one research lab, practiced in a new clinical environment, and then moved on to the next. I remember being ecstatic to begin an internship at Cedars-Sinai Medical Center in Los Angeles. In my mind, I was well on the road to becoming a world-class surgeon, and that's when I recalled what I had learned at Brooktrails Lodge: Good things come to those willing to work longer and harder than anyone else at the jobs no one wants to take. I resolved to say yes to any assignment.

Frankly, I never once imagined that they'd stick me in a hospital autopsy room, though. Those nights I spent in the mortuary played no small role in the premature end of my medical career. Suffice it to say, I discovered I was more of a people person — an alive-people person. But the lesson remains the same:

Good things come to those willing to work longer and harder than anyone else at the jobs no one wants to take.

I knew I had a good work ethic. And I knew I would go on to do something more.


My time in the autopsy room aside, I could see at some point that there were some emerging signs that a fissure was growing between what I thought I should do and what I wanted to do. I was no longer sure I wanted to pursue my original career path. If not medicine, then naturally, I thought my calling should be law. (Let's just say that even then, I knew I didn't have the disposition to be a rabbi.) So, my senior year at Brandeis, I made a 180-degree turn, registered for the LSAT, and applied to law school.

But when acceptance letters arrived, I felt none of the excitement, none of the purpose that I remembered so fondly from my early days at Brooktrails Lodge. How could it be that this wasn't right, either?

I didn't know what I wanted to do; I just knew I didn't want to spend my days in an office, kept company by briefs, legal texts, and impenetrable judicial decisions and corporate contracts. It all just seemed so ... regimented. I envisioned where I'd be in three years after taking the bar: in a clerkship at a firm whose letterhead was the compiled list of founding partners' surnames.

But where was the adventure?

Where was the excitement?

Where was the opportunity to do something no one had ever accomplished before?

Like many young graduates I talk to today, I had a diploma but not a clue. I didn't know what I wanted to do with my life.

And having just finished financing four years of my college tuition at the time, my dad was none too pleased about this. Since I didn't have a sense of direction, he made sure to provide one for me. He called me home, to Las Vegas in those days, to learn his newest revolutionary innovation in real estate: timeshare.


Striking Out on My Own

I built my success on the timeshare industry. It wasn't easy, it involved great personal risk and sacrifice, and I stumbled plenty along the way. Still, core lessons I'd learned from my family, my early jobs, and my academic career stayed with me, and I often counted on that early wisdom to keep me grounded. Today, I'm probably most known in the business world for the way I helped reinvent and redefine the timeshare industry, but I hope, however, that you'll see me as someone who's worked hard to make something bigger than that, as someone who advocates for authentic hospitality in every sphere of influence. This is the story of my journey, as it begins in real estate.

A Truncated History of Timeshare

Timeshare may be a taken-for-granted part of vacationers' lexicon today, like it's always been an option, but it certainly wasn't awhile ago. So that you understand how I got to where I am in business today, let me offer you a short history of the concept before I get into the nitty-gritty of my career path. As I share the details — both good and bad — I hope you'll see just how far timeshare has come and how this set the scene for the Meaning of Yes.


Depending on who you believe, the timeshare first got its start in Switzerland or France sometime in the late 1950s or early 1960s. But everyone agrees that the invention was designed by families, for families who wanted a better way to get away.

In Switzerland, an ordinary man by the name of Alexander Nette decided there had to be a way to incorporate regular holidays on his annual calendar. The barriers? Rent. Upkeep. Time. Even in the midcentury boom, holidays were expensive, a luxury that many regular families couldn't afford on their own, at least not annually.

I like to believe that the mantra "Necessity is the mother of all invention" holds true in Nette's case. Determined to find a way to make regular vacations more accessible to everyone, he teamed up with a business partner by the name of Dr. Guido M. Renggli and together, in the fall of 1963, they founded a company by the name of Hotel- und Apartmenthaus Immobilien Anlage AG (Hapimag). Immediately, the duo began to acquire resort properties. But here's the kicker: As opposed to traditional deeded real estate, Nette and Renggli marketed Hapimag as a new "right to use" share program. Not only was Hapimag the first timeshare operation to use a points program and offer its members different timeshare destinations, it's still a successful company to this day.

Nearly simultaneously, a French company by the name of Le Societe des Grands Travaux de Marseille — quite a mouthful, even for the French — began selling at a ski resort in the French Alps. Their advertising mantra? "No need to rent the room; buy the hotel, it's cheaper!" Pretty catchy — it's no surprise it caught on.


Timeshare was a bit slower to take off stateside, but once it did, it spread like wildfire. First there was a hotel-condominium project on the island of Maui, which broke ground in October 1965. Hawaii proved a wellspring for the timeshare industry, and shortly thereafter, another project arrived on the scene, the first non-hotel condo timeshare sold in the United States, on the island of Kauai. Founded by Bob Burns and Bob Ringenburg (dubbed the "two Bobs"), this small operation selling leasehold condos in weekly intervals became timeshare giant Vacation Internationale.

And that brings us to another great name of this generation, Brockway Springs, the first deeded timeshare program in the United States. Originally a single property opened in 1973 in Lake Tahoe, California, developer Innisfree Corporations grew its business, joining forces with Hyatt Corporation in a fifty-fifty joint venture led by industry legends Carl Berry, Paul Gray, Greg Bright, Doug Murdock, and Dave Irmer.

This group of men made timeshare a household term. Interestingly enough, their choice in words wasn't a stroke of marketing genius or the product of incessant message testing but rather a plain and direct attempt to make the product intuitive and understandable. Bankers, a major target audience, were already familiar with the term in their own business, as time-share referred to the sharing of mainframe computers.


By the 1970s, timeshare familiarity, construction, and purchasing had skyrocketed. The phenomenon was a confluence of push-pull factors: real estate developers having difficulty selling full-ownership condominiums in a down economy and the booming consumer popularity of the interval model.

I can't underscore this point enough: The introduction of the "mainstream vacation" appealed to people everywhere, with every level of economic means. The promise of a timeshare became synonymous with the dream of luxury getaways, reasonable prices, and mobility for all Americans.

Most of my readers can probably intuit the rest. By the 1990s, major hotel companies (including Marriott, Sheraton, Hyatt, Hilton, and others) began offering vacation-ownership properties. Today, add Starwood, Disney, and scores more to that list.


Excerpted from "Checking In"
by .
Copyright © 2018 Stephen J. Cloobeck.
Excerpted by permission of Greenleaf Book Group Press.
All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.
Excerpts are provided by Dial-A-Book Inc. solely for the personal use of visitors to this web site.

Table of Contents

Foreword ix

Introduction 1

How This Book Is Structured 15

Part 1

1 Beginnings 21

2 Striking Out on My Own 31

3 The Sunterra Saga 43

4 Toward a Turnaround 55

Part 2

The First Principle of Hospitality: Focus Unrelentingly on the Guest

5 The Meaning of Yes 67

6 Be My Guest 77

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 a 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 3

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 4

19 We're All in Hospitality Now 221

Acknowledgments 235

Notes 237

Index 247

About the Author 257

Customer Reviews