Stephen Cloobeck's Intro

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Today on the servant leadership podcast, we're joined by Steven Klubck, a dynamic entrepreneur, investor, and leader best

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known for founding Diamond Resorts and appearing on Undercover Boss. From studying neuroscience and psychology to

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building one of the largest hospitality brands in the world, Steven has always looked for ways to solve problems, build

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strong teams, and lead with both compassion and conviction. Now, he's bringing that same mindset to his run

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for governor of California. In this episode, you'll hear stories about leadership, risk, public service, and

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what it looks like to create real value in every room you walk into.

Welcome Stephen Cloobeck

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Stephen, thank you for being on the Servant Leadership Podcast. Thank you for having me. I am so excited because

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with your background, you have proven out to be an amazing servant leader. Talk about Diamond Resorts and what the

Diamond Resorts Background/Journey

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journey was like to start that. Wow. Uh I was tasked to build my first

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hotel at 29. I was in the shopping center business prior to that. But prior to that, I was going to school to be a

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heart surgeon. So I have a degree in neurobio psychology. And I thought I dreamed of being a heart surgeon. And I

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I didn't I got tired of going to school. I worked at Cedar Sign Medical Center, did heart research, and I loved that.

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It's a passion, but I just could not weather another 16 years of school. So, I came back home to Southern California

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where I grew up. And I went to Cal State Northridge to learn accounting 101 and 102 cuz I did not learn

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that. And then took business law, UCLA, honored it, and went into the shopping

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center business to learn. and started my own company at 24. Built centers from Burbank, Bakersfield throughout Southern

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California. I was tasked to build this first hotel for my father for the time share business at

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29. He was not a builder. He was sales and marketing. He was Gleng Gary Glenn Ross. Great sales and marketing man. And

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uh he gave me a budget and I designed it. I built it on time on budget at 29.

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And then got into the hotel business full circle. My life is full of full circles. I did speech and debate when I

A Life Of "Full Circles"

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was a young man. Won 13 gavvels at student congress and now I'm in politics and policy too. I became a builder

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because I learned critical thinking how to solve problems and that's so integral

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in life solutions. I learned from some of the greatest mentors. Michael Milin in finance. He

Importance Of Mentors and Serving

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gave me my business degree. M Harry Reid, the great leader of the US Senate,

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gave me my political science degree and became my adopted father. And I met these men when I was actually young, 13,

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15 years old. Never knew that again full circle that be so prominent in my

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life. And I learned most importantly to listen to others, learn, have mentors

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because I'm a product of these great mentors. So

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today I'm giving back. I'm paying it forward. Actually paying it live by

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having a lot of mentees and service has been a big part of my life. Actually I

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was a bus boy at 8, a dishwasher nine, waiter again. Full circle. I'm serving

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again. And I love serving. People should serve because it makes you feel good. I

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do it both philanthropically, but I also roll up my sleeves and deliver results

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and just helping those that need. Um, but I've learned to be

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uh always authentic, directive, and

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authoritative, but with compassion and warmth because we're missing that compassionate warmth. We need to create

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value for everybody. And as I've been so privileged to uh create value for many

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many others, I've created value for myself and I lean into it. I'm proud of what I've done and I want to share it

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with others. It's amazing just your journey and how you really have created so many good leaders on under you. Uh

Instilling A Service Mentality

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they talk about great leaders just leaving a wake of amazing great leaders behind them. How did you instill a

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service mentality? Obviously, you're in the hospitality industry, but how did you instill that in the leaders around

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you? By walking the talk, not being afraid to pick up the broom and sweep. I

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can do and have done every task within my business, soup to nuts. When it comes

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to making a bed, I can make a bed. I taught my team how to I wanted our towels folded. I did a video and sent it

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out with technology today to everyone. And I would walk around and visit with

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my team and talk to them and listen to them. Doing undercover boss was a great learning experience because I never

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really understood, you know, my team wouldn't tell me everything. But now, now I could figure out how to actually ask the right

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questions. How's your day? How's your family? How are the kids doing? If I

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thought about how many kids I put through school, not just my own family, which is

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I think I put 10 kids through school, my immediate family and relatives, but all

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the others that I put through school by providing just a great workplace, a

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team, a culture where I would take a bullet for any of them and they would for me. I had to

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say as the founding chairman CEO when somebody called because I put

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my business card at every front desk with my live cell and live email. My people thought I was out of my mind. But

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I would respond to each and every guest and if we did have a complaint because

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we're not perfect. I'm not a perfect man. None of us are perfect and acknowledged that's okay. But how do you

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make it better? I was in the business of creating memories for my guests, but my team was equally as important. But if we

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did fail, I would talk to a guest and I would

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say, "Wow, tell me about what happened." And I'd listen and I said, "You know

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what? I apologize." And they go, "Whoa, whoa, it was a housekeeper at X resort or a

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server at another resort." I said, "No, I apologize because I am that housekeeper.

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M I am that server. I'm everyone. I take the incoming shots and

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I clap for my team in the back of the theater. Great. When I let them all get trophies, I have no pride of authorship

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because if we deliver results and make people's lives better, we create memories for people and create a great

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working environment. That's what true leadership is. A papa bear with a big heart. M and

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we have to have rules but we need simplified rules so everyone prospers

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and does well. We have regulations so we keep bad actors away. Mhm. But not too

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many regulations where good business can't do good business. People say common sense but common sense is

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uncommon sense. So these are principles that I believe in and a really true great

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leader creates rock stars. M cuz as I was created by other mentors, I hope I

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create many, many, many rock stars for the future of our country, our planet,

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and I wish more people would just kind of embrace that. Yeah. Well, and you've taken this path of inspiring people all

Undercover Boss Experience

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around the world, even outside of your companies. Uh you talk about Undercover Boss and being on that. How did that

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even come about and and what was that experience like? Wow. Uh it's it it we actually created

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the best shows but it happened in a very unconventional way where they asked me

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to consider it. I said okay and the first day on the set I was very uncomfortable cuz I was

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exposed and I had no editorial approval and I said they're going to kill my

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brand. they're going to kill the company. And I quit. The first day I quit and then they fired me and they

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said, "Do it on camera." And I said, "No, I'm out of here." And the producers flew in to meet with me that night and

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walked me off the ledge and said that they could not do this show unless it was aspirational and inspirational and

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real and unscripted and raw. Play with it, Stephen. it's going to be fine

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because we wouldn't be able to attract these other great companies to come on.

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And I said, "Okay." And then we created great content because I leaned in. I was

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very uncomfortable because it's my baby and I would didn't want to expose my baby to things that I couldn't control.

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But I let loose and we created the best shows they ever created. And it was

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totally unscripted. The most generous undercover boss ever in the history of the show. Great ratings, but I learned

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so much. It made me a better leader. Yeah. I mean, it was for sure the most

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memorable episode. Uh it thinking about your path through Diamond Resorts, most

Approach After Diamond Resorts

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people when they sell a business would just be living off on the beach and not do anything after. Uh you've taken a

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totally different approach. you you've leaned in to some really hard stuff since uh since selling. Why why did that

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happen? Well, it's interesting. Somebody asked me a similar question and they

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said, "Stephen, you must like that red cape in a bull ring because you seem to

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charge after it." If somebody tells me you can't do it or it can't be done, I kind of lean into it. I like Legos, as

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you have seen. I like building things. I like creating value. Um, I like doing the most complicated,

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the most impossible. When I bought Subtra, it was a 20-year-old troubled company. Nobody could fix it. I don't

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rep and warrant the financials of the company I bought. That's a little crazy. I do not suggest that for others. But I

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did it and we succeeded. We bought 10 more companies and fixed them. We solved the sins of the father. Many problems that others

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couldn't fix, but we made it right by the customer all the time. I didn't garner any profit, but

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yet we made everyone happy. And it wasn't for everybody. Maybe it was not right for them. And we said, "Maybe this

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is not right for you." But if we or others in the past made a mistake, I solved it. And along the way, people

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have tried to extort me. Oh, no one extorts me. I fight extortion. And with

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me in charge, you'll be protected from extortion because I live by laws. I

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don't like when others get taken advantage of and I protect them. And I live on principle. I live up integrity.

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We don't lie. We tell the hard truths. Matter of fact, I have a book. Yeah. That's called Facing Hard Truths Out.

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And I wrote a previous book called Checking In. It's on hospitality because everyone's in hospitality.

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So, I did not envision, you know, I' I've been appointed to political office. I created the tourism department of the

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United States, brand USA. It outsized its returns. It was supposed to be 5 to one. It's multiples of that.

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President Obama was like cheerful, but as I was creating it, they were nervous because I'm like a bullet in the china

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shop, but they weren't used to somebody signing the front of a check and just making decisions. I would make decisions and

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apologize later, right? That seems to be a mantra. But always lead with my heart.

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Always with integrity. Renamed an airport in Las Vegas. They tried seven years. had it

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done in three months in honor of my adopted father, Harry Reid. Very proud.

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So, I've done a lot of unthinkable things. And as I came to my home state,

Living My Dream In California

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my dream I dreamed of living in Beverly Hills. I lean into it. I'm not a I'm not ashamed. I'm proud of what I've done

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because I lived grew up in the San Frernando Valley over the hill of nice means. Went to good

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schools, public and private schools. And I wanted to live my dream. I always dreamed of living over the hill,

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designing a house in Beverly Hills. I could live anywhere in the world as I sold my company and I traveled the

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world. Operated 35 countries, 16 languages, six currencies,

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multiple legal frameworks. And I wasn't worried about the tax

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situation. I was worried about where is the best place to live. Well, the best

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state's California. It's the best state in the United States. It's not a state, it's a country. We're now the fourth

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largest GDP in the world. Yeah. And it's been on defense. I grew up when it was

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on offense. The bully pulpit of the United States, as California did, the rest of the nation

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led. And I interviewed because I've been involved in politics and policy for almost four decades. I interviewed every

Decision To Run For Governor

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single candidate that was running for governor. And I met 300 people throughout the state to get to understand where is the state of the

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state of the country and I looked at the gubanatorial candidates and I said is

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this the best we got? You're kidding me right? Not one person has

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solutions. Not one person has signed the front of a check. Not one person has fixed

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broken. They're just looking for a title and a paycheck. I don't need either.

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Mhm. I want everyone to do well. So, I'm coming at this very differently. And I said, well, to my friends, maybe I should

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think about getting involved and use the experience I have to fix what's

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broken. And they said, are you out of your mind? I said, well, you know, I'm a little bit out of my mind because

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everything I've done's been a good trouble or good crazy difficult. What do

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you need this for, Stephen? You've you've done all these great things. Well, I you know, I played enough golf.

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It's boring to all those golfers. Sorry. I love pickle ball. Um I've traveled the

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world. I love my state and I can actually add value. So I asked my

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children uniquely, should my daddy do this? And I got three different answers.

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All yes, but very different. One actually said, I have 13 questions. It's my lawyer to be. And I answered every

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question and he said, "What do you expect of me?" I said, "Show up when I announce." He said, "Well, can I help

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you with policy and help, right?" I go, "Yes, of course." So, I wanted to make sure I had

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good infrastructure and buy in. And what is my legacy going to

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be? Here to serve. I'm here to take care of all the customers of California. Not

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voters. They're all customers because they should receive equal or greater value. They deserve this. They need to

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hear this and deserve to hear the hard truths. And that's why I wrote the book too a year ago. It's now published. It's

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coming out for print. It comes out June 2025. Facing hard truths. Um, Amazon

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Barnes & Noble plug. And love it. I just love what I'm doing. I've never had a

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better time in my life. I love serving. It it's such a unique stance because you

Why Haven't Others Succeeded?

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hear all these people and I agree. Most people run because of power and position and title. Uh hearing what you're

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running for and hearing what you're trying to do in California. Why has it not been done before? Because these folks are

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careerists. They're they're looking for title jump, their hierarchy. They think they're they deserve it. They go to a

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buffet table and pick things. I didn't intend to do this. It's not on my bucket list.

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I'm here because we're all placed on this earth to add value and I'm here to serve. I'm enjoying what I'm doing. I've

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studied. I've done due diligence. I've done my homework. These folks have not done their due diligence. They just want

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the title. I don't want a title. I have no aspirations beyond this other than serving the people, the customers of

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California. And there's a there's a craving for this. I'm not

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embarrassed for what I've achieved. And I want to treat people with compassion

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and warmth. And the people deserve this. Actually, they've

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been abused to failed leaders. We just saw the California fires, Southern

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California, failed leadership. We saw two billion dollars of accounting fraud for the homelessness in

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Los Angeles. And at the state level, 20 billion. And then you go to workman's

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comp edd 30 billion. Where's the money?

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I listened to the people of California. From the head of the farm workers to the

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CEO of Chevron, the same thing. Leadership did not talk to its best customers. Why do you think so many

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people have left? Government has failed its

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customer. Now's the time for us to change. we've had enough with so many

Talk versus Action - Hope Feels Real

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people uh they talk a good talk and you've been a person of significant

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action throughout your career uh and when you talk the hope feels real like it actually feels hopeful. I live in

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integrity. I will never promise something I can't deliver equal or better. I'm in the customer business.

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We're all in the customer business, but it's forgotten. And these leaders

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proven have failed us. They've failed us. We wouldn't be in this position if

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they did a good job. Yeah. Okay. We wouldn't be having this discussion. I wouldn't even consider this if they gave

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us a successful result. They haven't. So simple

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solutions for a better life and it's going to be done a different way because

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those that have caused this are not going to be those that fix it. They're incapable otherwise they would have done

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it. Mhm. Correct. For sure. So here we are today. I'm having

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fun shaking hands, listening.

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And there are problems that are solvable. I was taught this by my

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mentors. You can always solve a problem, but you got to figure out what it is first. Acknowledge

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it. Come up with simple solutions and execute and show

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results. And if you do that, what a beautiful world it would be.

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So most people in my seat don't want to

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do this because they're afraid of the media and the incoming missiles. I'm like, "Bring it on. Everything about me

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is all over the place. I'm an open book. I'm not scripted. I don't need to

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be because I am Stephen J. Kubc. I am who I am and I'm still learning. I'm on

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a journey. a lot more to learn but a lot to give. Okay.

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When I think through what you've done with building great teams and building just amazing hospitality environments,

What Is Exciting About Government?

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what do you get excited about moving into government where that just hasn't potentially been the case? Uh I I it

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hasn't been the case because I haven't touched it yet. But I did it at Brand USA at the federal level. I worked with

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Homeland Security, Customs and Borders, Senate, the House, Treasury Department, State Department, Interior Department,

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Commerce Department, and reported to the Oval Office. And I sat down with Customs and Borders. And I

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said to the head officers, "Can you do me a favor? We're

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going to spend a lot of money promoting the United States. Can we be a little Disneylandesque and

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say, "Welcome to the United States with a smile, cuz you already know who the bad boys and girls

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are." And we're going to ship them back on the airplane they came in on because the airlines got to pay for it. Little

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known fact. And when people leave and they leave the great United

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States, can we say, "Thank you for coming. Come back soon." With a smile.

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Pretty simple. And you know what? They agreed. And we changed the way we

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greeted people and people left the United States. They're spending money here. It didn't cost us

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anything. Tourism and travels and export. Okay, it's counterintuitive. Is

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23% of our GDP, our revenue stream of the United States.

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And people from Europe spent so much money. People from China spent four times as much and other Asian countries.

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Come on, welcome them with a smile. Show them our great land and our great

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hospitality. It's so interesting. Just I love your perspective. When people look

Facing Challenges

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at you from the outside though, uh, a lot of people think, boy, everything he touches turns to gold and it's just been

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an easy ride. and and behind the scenes, we know it hasn't been an easy ride. There's been some really tough

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challenges you've been through. Talk about some of the challenges and how you've overcome them. Well, look, when

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you eat sausage, it tastes great, but if you watch it being made, you'll never eat

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sausage. Of course, there's challenges, but I learned to lean into getting smacked in the face, cuz that's a

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learning experience. You just make sure you don't you're driving down the freeway and you may hit the guardrail a

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little bit. Just don't go over the guardrail because you may end up not making it back. So, look, I've had so

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many experiences in my life that were unintended consequences which people don't talk about or think about because

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they haven't had experience. And that's what I bring to the table and the other candidates

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don't. They don't think of unintended consequences. the 20 spinning plates and making sure they're all spinning at the

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same time. But each time I've had an unintended consequence, I've weathered the storm.

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And boy, it's tough. Boy, it's tough. You You get banged up, beaten up,

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smacked around. I just like it. Told you I'm a little cuckoo. Good cuckoo. But I

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lean into it because I know it's going to be a growth experience. I'm going to learn something new. We're going to

23:04
figure it out. It's a puzzle. But if you lead with compassion and warmth and you always have integrity,

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you're going to do the right thing. And it's okay to ask for help because you can't do it alone. We need to do it

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together. It's not I I, me, me. I'm the opposite. It's we. We need to do this

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together. We cause these problems. Don't point fingers. Don't point fingers. Don't yell at me.

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Don't point fingers. If you yell at me, I'm just going to say I can't hear you. How can we do it together for a better

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life? We got to figure it out, right? We have to respect each other. We need to

Some Simple Truths

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be responsible to one another. We need to show

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results. We need to execute. We need to have accountability. And we need to enforce laws, simple laws. We need to

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agree. We don't steal eighth commandments. simple truths we need to hear and we all

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deserve to hear. Does that make sense? Yeah. So, if anyone thinks it's just I touch things, it turns to gold that day

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is not true. I make mistakes. I pivot, but I pivot. I raise my hand if I make a

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mistake. Cuz nobody is perfect. One of the things I've learned from following you over the

New Book: Facing Hard Truths

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years in not in these exact words, but but these three steps of no excuses,

24:26
take personal responsibility, and then lean in and fix it yourself. Uh you've demonstrated that over and over with

24:32
your book. Uh talk about the book. I know you mentioned it briefly, but talk about the book and what it was like

24:38
going through that writing process and and what you hope people get from it. First of all, I dictated it because I

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cannot write. A little known fact, I'm very dyslexic. I have things read to me.

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I actually listened to the audio of it and took notes. My scribble is like a doctor's chicken scratch. But these are

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lessons learned, best practices, and we grow on the shoulders of others. So, I've learned all these

25:04
beautiful things from I don't play identity politics. I'm a Democrat because I'm

25:09
loyal, but I'm a conservative Democrat. When I say conservative, I'm a

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populist. I'm for the people, but I'm balance sheet income statement. I'm law

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and order, but I'm compassionate with a warm heart. I don't know what you call it. I call it being a good human. Mhm.

25:28
Forget about this D and R crap. But you got to do it. Mhm. I speak to an

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audience, they don't know what I am. Some people think I'm a Republican.

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Some people think I'm a Democrat. Some people think I'm a Democrat. to people who become a Republican. Does it really

25:45
matter as long as you have respect, responsibility to deliver

25:50
results? So, as I wrote this book, this is just a compilation of all these great leaders that I've learned from in this

25:57
unique period of time where we got this patrolic language, hard right, hard left, and I'm trying to run through the

26:03
hard center because there's no language. And I'm not apologetic for it. There's no bravado

26:10
for it. I'm that bravado. I'm out of the wilderness and I'm here to lead and

26:15
serve because now's the time to shine. Ah, sure. I can

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go do whatever I want, but then what am I leaving behind? Why would I waste this

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experience and talent and I'm unemployable? I need a job.

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So I say this kind of truthful, but why not create more rock stars, create these

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great leaders, educate, collaborate, teach, coach, counsel, collaborate, and teach the unintended

26:49
consequences. Make people think in a very thoughtful way, you can have all the credit. I want

26:55
no pride of authorship. I just want to sit in the back of the theater and clap for the team getting trophies, whether

27:01
it be financial if that's what they desire. Leadership, education, science,

27:07
medicine, whatever it may be. Make the world a better place. Okay? Walk

27:14
together. We hear often this concept on our podcast of people thinking they're

Helping Others To Feel Leadership Confidence

27:19
not leaders. And o over time uh we're trying to show people that no matter

27:25
where you are, you have influence and and you have great leadership capabilities. When you go and work with

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people, and I know you're working with people at the seauite level, but you also are working with some of the the poorest of the poor in some of the

27:38
community work you do, uh what do you tell people in terms of helping them feel the confidence to be great servant

27:44
leaders? Good question. I don't I don't just work with people at the seauite

27:50
level. Yeah. I I I'm I'm in the weeds. Y No, I'm I'm washing the floor and

27:57
sweeping the floor. I have taken care of 42 homeless families in Los Angeles for the last 5 years. And I go visit with

28:04
the men and women who are there that have graduated. They come from the street, drug, alcohol,

28:12
addictions, and we sit and talk. And I got a really interesting comment back

28:20
from one the second year I I was speaking. I speak a couple times a year to the to

28:27
the people. And he said, "Mr. Clebec," I said, "Stephen, Stephen, Mr. Clebec was my dad." He goes, "Stephen, you're not

28:34
going to believe it. I enrolled in hospitality school." I said, "Oh my god." Okay. He is one of many that I

28:42
have talked to that have listened to our

28:50
collaboration that pulled up his pants, put his shirt on, and got it

28:56
together. And that's success. It can be done.

29:01
So, I'm doing this each and every day. To me, running for governor of California is the greatest hospitality

29:09
job in the world. There's 39 million customers of

29:14
California. I get to shake hands and talk to everyone hopefully and listen

29:20
and create memories for them and a better life. It's just going to be done a different way. So, there is a pathway.

29:28
There's a desire. I'm motivated. I'm having more fun than I've ever had. And

29:35
it it it it wakes me up every morning. I could barely sleep because it's so much fun. It's so much fun. And I know what

29:42
to do. I don't need training wheels. I can drive the car day one. The other candidates can't. Yeah. They don't have

29:49
the experience because they haven't signed the front of the check. They just want the title and the paycheck. Yeah.

The Concept Of Listening

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Where do you think you learned this concept of listening? Because your listening is not just hearing. Your

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listening is listening for the sake of being able to do something about it. Where where did that come from? Good

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question. I learned the concept of staying present. Okay. I'm not listening past

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you. I'm listening to you. I'm absorbing your journey. I don't know

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what it's like to grow up the way you did unless I ask you and you tell me.

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You can't assume how I grew up unless I have a nice conversation with you. Got

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to get to know each other. How'd you grow up? You learn because what you did in your

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journey is different than my journey. And it's interesting to me. To me, that's just being in the hospitality

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business and kind of learning from one another and growing with each other for

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a better future, right? Mhm. I don't know. I like it. I think it's pretty good. We should all embrace it. All

Ten Rapid-Fire Questions

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right. I want to hit you with 10 rapid fire questions where you just say the first thing that comes to your mind. And

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there's no be careful. There is no right or wrong answer. That's good. There is no right or wrong answer in life. Who

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Who's the first person you think of when I say servant leadership?

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Uh my dear pastors or rabbis. Five words that most describe you. Respect.

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Responsibility results integrity, compassion, and warmth.

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Favorite author or book? I don't read. I mean, you want to ask like a TV

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show or something? All right. Favorite movie. Go. Favorite movie? The Godfather. Oh, that's a good one. All

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right. Favorite food. Steak. Love it. Favorite thing to do in your free time. Workout. All right. What's a surprising

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fact about you? That I understand 95% Spanish and I speak a little bit of

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Russian and can read it. Wow, that is surprising. That's all right. Favorite place you've been? I've traveled the

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world. Um, my favorite place is California. Love it. Where's somewhere

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you want to go that you haven't been? That's a tough question because I've been fortunate to travel the world and I

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can actually say I've I've been everywhere that I've wanted to go

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because I was in the hotel travel and tourism business. I've really ventured the world. Wow. All right. What's the

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best advice you've ever received? Staying present. Wow. Wh when you think through why a

Why Is Servant Leadership Important?

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podcast on servant leadership could be important, why do you think that could be important for people? Service is the

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most important quality one really needs to embrace. I think everyone should do

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service one time in their life or many times because number one it teaches you

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about people. It teaches you about sales, marketing,

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human nature. It it it brings the best out of you. And

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you know what? When you do serve, you feel good at the end of the day. How can

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you beat that? Yeah. Wow. Well, Stephen, I just want to

Closing

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say thank you for inviting us into your home and for sharing with our audience uh so much wisdom. I know they're going

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to be really blessed by hearing from you and your story. Everyone should have a blessed day. Yeah. Thank you for

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listening to this episode of the Servant Leadership Podcast. If you enjoyed what you heard, please give it a thumbs up

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and leave a comment below. Don't forget to subscribe and hit the notification

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bell to never miss an update. Be sure to check out the servantleershipodcast.org for more updates and additional bonus content.