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A
Hi, guys, it's Tony Robbins.
B
You're listening to Habits and Hustle Crush.
A
Sam.
B
Okay, you guys, we have a very special guest here today. We have Stephen Klubeck. That's how you pronounce your last name?
A
Yes.
B
If you guys are somebody who is interested in a business, scaling a business, starting a business, disrupting a business. Disrupting a business. There's probably, you know, not many people better at it than Steven. He sold his business for $3.3 billion.
A
Enterprise value.
B
Enterprise value. Thank you.
A
Net 2.2 billion.
B
Net 2.2 billion. That's true. He is exceptionally philanthropic, which is what I like about you.
A
Given away close to $63 million. You are giving away close to 63 million.
B
63. Okay. Are you. Are you on a. Do you have a particular amount that you're trying to get to?
A
No, just very philanthropic.
B
Very philanthropic. That's basically why he's even on the show, because a friend of mine, Shawnee, asked me to meet with you because you're so philanthropic. You're so great. You're so wonderful. And then I looked into you, and then guess what happened. This is how the world works.
A
Tell me.
B
Okay, so she tells me about Stephen, and then I'm like, doom scrolling on Instagram.
A
How many mutual friends.
B
And a lot of mutual friends. But you know what came up? Your little clip from the school of hard knocks.
A
That was. That in the street. That was. Just happened.
B
When did that happen?
A
About nine months ago.
B
Okay.
A
Well, this young man came up to me. Well, then he came back and wanted to meet with me, and I wanted to help him grow his business.
B
Well, he's doing pretty good, too.
A
He's. Because he's got a little. Nice little platform.
B
Yeah, he does.
A
For young entrepreneurs. And I love young entrepreneurs. Doing well.
B
Yeah.
A
And that's how I learned. I learned from great mentors. I never went to business school, I heard, but I actually got a degree signed by Mike Milken because he taught me. I was fortunate enough to meet him when I was 13.
B
Was this was before junk bonds or after junk bonds?
A
It was during that time. I didn't know I was studying to be a doctor. I was going to be a surgeon.
B
Really?
A
I worked at Cedars Sinai four years.
B
Like a nice Jewish boy.
A
I was going to be the doctor. My brother was going to be the lawyer.
B
Really? I'm sure my mother was thrilled.
A
They were thrilled. But I didn't become the doctor.
B
Well, I think you did okay for yourself.
A
But I'm still involved in medical technology and research, and I still Involved.
B
Okay, wait. Let's start from the beginning because people are probably very confused. Okay, so you extremely. You're. Because first of all, I'm just going to give a couple more facts about you. So you were on Undercover Boss for many episodes, which no one's ever done.
A
Yeah.
B
And yet. And you gave the most money away even on that show.
A
True.
B
Right. Okay.
A
Totally unscripted.
B
Completely unscripted.
A
Unscripted.
B
Okay, so there's that. You're also running for governor of California.
A
Unintended.
B
Unintended. Which.
A
Because I interviewed every candidate, not one I would trust with my family's life. Safety.
B
Okay, tell me about this.
A
I. I interviewed every single candidate. I mean, I ran tourism in the United States. I don't know if you know that.
B
No, I don't.
A
I worked for President Barack Obama. I created Brand USA in 2009. 10. And it's still around today with the same standard operating procedures and its returns are outsized for the United States. I ran the state of Nevada. I passed laws in many states, changed a law in Delaware, business law, which is almost impossible on derivatives operated in 35 countries. So I've had a vast wealth of experience. And when I came back to California, because I grew up in the Valley.
B
That's so funny you did that. Did you grow up wealthy or. Not really, No.
A
I went to Harvard School for Boys, now Harvard Westlake.
B
That's. Well, that's a private school that.
A
But I went to public. I went to public schools, too. Lanai wrote.
B
Okay.
A
And I grew up in Encino, Woodland Hills, kindergarten. But we moved from Chicago when I was very little and I. California boy through and through. And I left California. It's a storied career where I was going to be studying to be a surgeon, a doctor, worked at Cedars, have a degree in hard science and decided not to go to the school anymore. I went to Brandeis University, have a degree in neurobiopsychology.
B
Yeah. By the way, these are not like, these are great schools. These are like Ivy League schools.
A
And I barely got through. I didn't know I was dyslexic.
B
Well, yeah, I saw.
A
I negotiated my grades.
B
How did you negotiate your grades? Sounds familiar.
A
Yeah. So I should have realized. I should have gone into business.
B
Well, how did you negotiate, like, how did you get in in the first place?
A
Relationship with the professors.
B
How did you meet the professor?
A
Because at Brandeis, we were very small classes. So of course you knew all your professors.
B
But how did you get into Brandeis? Because you have to have good minds.
A
I transferred from usc. I was there one year.
B
Okay.
A
And I did well enough to get in. And a relationship helped me. A relationship helped me. And I managed to get through Brandeis. If you look at my transcript today, it's published my first book, Checking in on Hospitality. It's a common group of Cs, maybe a couple of Bs. One A in human memory. I remember that.
B
Wow. Yeah.
A
No pun intended. But I have no idea how I got through school other than memorizing. Seriously, Memorizing everything. And I found out only I was dyslexic when my adult son was diagnosed. Because nobody understood that when we were going to school.
B
Right. It was a different time.
A
So it just powered through everything. Powered through everything. But it was able to. Being dyslexic, you're able to think out of the box because you don't think A, B, C, D, E, F, G, linear linearly. You just can handle multi dimensional chess. 10 games of chess, 7 levels out all the time. And that's how I think.
B
So did you. Okay, so did you just, like, read backwards at the time?
A
It's not reading backwards. It's just not reading, not comprehending.
B
So it's not retaining the information.
A
No, but if I. But I could memorize pages.
B
Yeah, me too. That was how I got through school too. Memorizing.
A
You're probably dyslexic. You don't even know it.
B
I just think I'm bad adhd. Like I can't concentrate.
A
So what is it? It's a combination of. But this makes you unique and it gives you a gift.
B
Yeah.
A
And everyone needs to embrace these gifts that they have.
B
I don't use it as a crutch. I think it's silly.
A
No one has a crutch. There's no crutches.
B
There are. Because we're living in a time when.
A
That's because we helicopter our kids.
B
We helicopter our kids. We coddle our kids. We're not able to let them just be bored. We're not allowed. We're not. We basically do too much for them and they're growing up to be less resilient and have zero coping mechanisms.
A
Where'd you grow up?
B
Canada.
A
Okay.
B
Yeah.
A
So Toronto.
B
Yeah. Well, Winnipeg first and then Toronto. But I hated school. But I. I like.
A
How'd you end up in California?
B
Job opportunity.
A
That's great.
B
Record label. Just. My whole situation's a whole other, you know, how I ended up here is completely insane. But I pivoted and my whole. That's the power of the Pivot. I just pivot. Pivot, pivot.
A
So do I. Yeah.
B
Oh, I know. That's why, listen, when I was like doing some research on you, because I knew you were coming on, I was like, wow, this guy. And I sound so like you. Like so many things about you remind me of me. But you're just have way more bees in front of your money than I do. You have way more money than I do.
A
But besides that, I just happen to take a lot of risk.
B
Listen, risk doesn't always work out, right?
A
No, it doesn't. Because I've been beaten up so many times in my career and when the chips were down, I just kept fighting, fighting, fighting.
B
Well, I want to hear about it. So, like, I want some tactical, actionable things that the listeners can, can glean from this podcast. Right. So let's start from the beginning of your career. How did you. You were in the hospitality world, right?
A
I started in the shopping center business out of college. So I went, came back to Southern California. I went to Cal State Northridge to learn accounting 101 and 102.
B
Okay.
A
That summer of 83, and then took business law at night at UCLA and just listened. And then worked for a shopping center developer for a few years. And they promised me a bonus, which they didn't pay me. So I started my own company at 24 and I just.
B
What was it? What does it begin as?
A
I built shopping centers, small little shopping centers. Like, for example, my first shopping center was not example, it was at Victory and Magnolia in Burbank, the northeast corner. I bought a Chevron station.
B
Okay.
A
Down and built a chief auto parts and four stores.
B
So wait, so you started off in like real estate development, basically?
A
Shopping center development, yeah. Leasing, managing, building operating. And then from that point built shopping centers throughout Southern California, Hanford down to Temecula. And I had one really bad shopping center during the late 80s where my subcontractors went broke, my general contractor went broke, all my tenants went broke as I was building it, and I almost went broke. And I ended up having to build that myself and weather the storm of getting through that project, which then allowed me to build my first hotel at 29.
B
So that's how it. So then you ricocheted into that from like the shopping malls to the one hotel.
A
Right. I built a large shopping plaza in Las Vegas called Polo Plaza. And behind that, Polo Towers. And it was a 60,000 square foot shopping center. And it was very successful at the time.
B
Who lent you money at the beginning?
A
We had credit companies.
B
So you did all the.
A
You did like, but before that was savings and loans. And at that time there was so much money available. They were.
B
It was a different time.
A
But you had to sign personally. So I had the risk of going bankrupt on every project.
B
Wow.
A
And I almost did on one. That one in Lake Forest, California. But I had very successful project in Mission Viejo, just down the street. But in Lake Forest, I almost went broke. But it taught me how to build because I had to actually build it myself because all my subcontractors went broke.
B
Well, how. Okay, so the. I guess my first question is how does I think a big thing is? People don't know like they think because they don't have the. The. The means, the connections, all the things like that. How does. What is the first step to starting that?
A
What's the name of your show?
B
Habits and Hustle.
A
Hustle.
B
You're preaching to the choir. But I still have to ask the question because I've never had you on the show. What would be the number one hustle? What do you think the number one skill?
A
Get up early, stay late, go to work with a runny nose. And when they tell you can't do it, believe in yourself that you can.
B
What is the one skill or the one quality that is essential for an entrepreneur to be successful?
A
Integrity.
B
Integrity. Okay.
A
Integrity is. Don't bust the trust with yourself or with others. Don't be around those that don't tell you the truth and just smoke out the bad people around you. Those that somebody who doesn't tell you the truth, you don't want to be around. But you have to also be truthful with yourself during good or bad times. And don't read your press clippings. Just keep your head down.
B
So you had this. So you went from that one hotel to how many did you end up having?
A
Ended up having 432 in 35 countries.
B
They're called Diamond.
A
They were called Diamond Resorts. Originally the company was called Sentara. It was a failed company. And I bought this failed company. It was a public company, and I took it private. So I had to hold a vote. I had to hold an election.
B
Wow.
A
And I just didn't need to get 50% of the stockholders to agree. I had to get over 90% because they had a poison pill in the documents. Now, mind you, when I was doing this, I didn't know anything about public companies. I was a private entrepreneur, Right. And I was now delving into the world of public company sec. Wall street business. And I didn't go to school for any of this. But I had good friends like Mike Milken and my friends who ran other large public companies. And I just listened and they were there to mentor. Mentors are very important.
B
You think so?
A
Huge. You cannot succeed without mentors. And that's why I pay it forward now.
B
How many people do you mentor right now?
A
Oh, dozens of young adults.
B
Really? What kind of mentor? How involved are you as a mentor?
A
They call me when they have issues, problems. I teach them cash flows. Always know your numbers. Always know your numbers. Always know your deal. You have to know your deal backwards and forwards better than any of your lenders or your partners. And one of my greatest successes, every single bank's always been paid back. I never negotiated with the bank, really never. They were always paid back because even during difficult times, I'd have to borrow more money from them to get through a difficult time. Because I always told the truth immediately. To the point where they said, stop calling.
B
What, what is.
A
You said integrity is very, very important.
B
Keep on talking. I'm just going to open my questions for you. So go ahead.
A
Everything's. Integrity is just a key, key component, part of success. Because you are your brand, right? And it takes decades to build a brand. And people forget that they are a brand themselves. And you have to be true to your brand. You can't pander, you can't compromise, you can't just do things because everyone else says that's the way it was done, or this is the way you must do it. If you think differently, if you have a different opinion or objective. But you have to have non vitriolic language when you communicate with others and collaborate and explain your position, not, not demand your position, not in a dictatorial way. Explain it where people embrace you, gain their trust. You trust the people you're working with. That's integrity. Communication is important, collaboration is important. And by doing so, you create an unbreakable team. You know, they, they say one stick is breakable, two sticks somewhat, three sticks tied together, which is a team. Unbreakable. It's actually biblical.
B
Yeah.
A
Ecclesiastes 4:12.
B
I think I saw you.
A
Pretty good for a Jewish boy.
B
Yeah, so not bad at all. I'm all about finding sustainable ways to optimize performance. The kind of work that actually moves the needle and how you feel and function. And that's why I really need to tell you about Prolon's five day program. Most of us are chasing quick fixes that never get to the root of the problem and the result is sluggish. Energy, brain fog and bodies running below its full capacity. But Prolon changes that by triggering your body's natural repair and renewal process at the cellular level. It's not a cleanse or crash diet. Prolon is the only patented fasting mimicking diet developed at USC's Longevity Institute. It's a plant based program with soups and snacks and drinks that nourish your body while keeping you in a fasting state. The benefits are backed by science, deep cellular rejuvenation, fat focused weight loss, no injections and better metabolic health and energy. Plus improved skin and even reduced biological age. And here's my favorite part. It's a complete reset in just five days. No willpower battles, no extreme restrictions. Just a structured plan to let your body do what it's designed to do. Repair, renew and optimize. And right now, Prolon is offering 30% off site wide plus a $40 bonus gift when you subscribe to their five day program. Go to prolonlife.com Jennifer Cohen and use Jennifer Cohen to claim your discount and bonus. That's prolonlife.com/jennifer cohen and use code Jennifer Cohen. You are big on the meaning. Like the word yes. Like the meaning of yes.
A
That's what I found lacking in the hospitality space. And I was able to disrupt that.
B
Okay, like.
A
And I marked that meaning of yes because look, it's value for a product. I was taught young by my father who's in sales and marketing. Always deliver equal or greater value to your customer. We're all customers. We're all customers. Even in politics and policy. We're not voters, we're customers. We should get equal or greater value to our tax dollars. And if we're not, we're voting for the wrong people.
B
What does your dad do for a living?
A
He was Glenn Gary Gun Ross. You ever watched that movie?
B
Yeah, he did a salesman.
A
Is that the guy Baldwin? He was that guy. He was ABC Coffees for Closers. That's my father. Really dynamic, great sales guy. Allegedly went to. He did go to finance school at University of Illinois, but he did not understand a balance sheet or an income statement. We used to get in arguments all the time. I said, I thought you went to. To finance school. He was a cash guy.
B
Yeah.
A
He didn't understand generally accepted accounting principles and he just dealt in cash.
B
Did your mom work?
A
No. No.
B
Did your. How. How. Do you have any brothers or sisters?
A
I. I do, but we got into a. A massive argument years ago. They busted my trust, so I was over money.
B
Of course.
A
It's Always sure they didn't want to.
B
Work, you know, so waste.
A
They're doing silly things.
B
Wait, so you have a brother or a sister?
A
Both. Both.
B
Older? Younger.
A
What's that?
B
Older?
A
Younger. Both younger.
B
So you don't talk to them?
A
No. No. They decided to sue my wife and my. Myself and my children years and years, decades ago.
B
For money?
A
For money? It's ridiculous. So I wrote him a check and said goodbye.
B
You. Why? Why did you write them a check?
A
Because I would rather not have the conflict. Just make difficult situations go away.
B
Even though that's your money?
A
I took his interest in the company.
B
Oh, were you guys partners?
A
We were partners, so I took his interest, so I just bought him out. Oh.
B
Gotcha.
A
Bad mistake on his part.
B
Wow. And what year did he leave the company?
A
Oh, it was decades. Probably two decades ago. Five years ago. A long time ago.
B
Because when did you actually sell this company?
A
2016.
B
So September. So you went from like. So you obviously, like, what's the difference between being a millionaire than to being a billionaire?
A
You get to give more money away.
B
Besides giving more money away, how did your lifestyle change?
A
I. My lifestyle's never changed. I mean, I built my dream house. I mean, you can't live in a house that I designed and built unless you have the wherewithal.
B
Do it right.
A
It's like a mini hotel. But I built it for events and to do charities and politics and policy. And I did it for my dream.
B
Right.
A
I always wanted to live in Beverly Hills, so I wanted to live over the hill.
B
Where were you living before 2016?
A
Before 2016, I was living in Las Vegas and I had a home in Cabo, and I had a beach house in Laguna Beach.
B
Oh, okay.
A
I had many homes.
B
So then you built this house in Beverly Hills once you made the money. The real money. Yeah, yeah, the real money. Besides that, because I see you have a security guard. Did you get the security?
A
I've had security when I was running Diamond Resorts. I mean, when you run a multinational company and you're dealing with 5 million guests a year, you end up with security issues. And now running for governor. Being a Jewish man in today's environment, you can only imagine.
B
I wanted to ask you about that.
A
Oh, it's serious.
B
Tell me. Give me some information about.
A
That's three death threats already.
B
Really?
A
Yeah. Anti Semitic death threats.
B
I'm surprised.
A
And people in politics and policy, you know, I'm so in the middle. Heart center. I'm old, Ray. I'm a Reagan Democrat. Balance sheet, income statement. We don't Steal?
B
Yeah.
A
You know, I'm unapologetically authentic with warmth and compassion and I just live to my brand and I'm not going to pander or I'm not compromised. So I just have done a lot of due diligence and I tell the truth and. And some people don't want to hear the truth. And today with the vitriolic politics and policy we have today, you only hear from the hard right and the hard left. So they both want to demolish me.
B
Well, it's interesting because.
A
But 68% of us want the hard center. We just don't have voice.
B
Well, that. What I was going to say is that that's like. I kind of feel that what used to be considered like the Democrats is not the same thing anymore.
A
I'm still the same.
B
Right. But the people who were Democrat, the party has changed a lot over the last.
A
Yeah. The wokeness is weakness.
B
The wokeness is.
A
It's weakness. It's weak. They have no breast balls. They have no breast balls and they forgot about the customer.
B
Well, have you not know? I mean, listen. Have you not noticed what's happened in Los Angeles in the last five years? First of all, last person to leave should shut off the lights. Most of my friends have already left la.
A
As I was moving back home, all my friends were leaving or have left, left. And their children can't afford to live here.
B
There's a lot of.
A
Because it's not affordable, livable, workable. We're closed for business. These are facts we've elected, unfortunately, leaders that don't understand our life safety. We just saw that with the fires.
B
Yeah, the fact that she's still even.
A
A mayor, first of all, how about the accountability? How about the wildfire money? Governor and Mayor Best. Where's the money?
B
I'm at what?
A
You tell me, where's the money? Well, it's probably given to charities upon charities on charities and it's all filtered off through GNA with side deals which should be investigated. Okay.
B
I mean, this happened that you remember, like a few years ago. Sure you do. Gavin. Everyone hated Gavin Newsom back then. Everyone hated him. And then he got re elected. It was shocking to everybody else. Like, everybody was shocked when he got.
A
Because. Because look, you cannot blame anybody other than we, okay? We did it.
B
Well, not we, but.
A
No, no, no, no we. Because we didn't fight hard enough on the other side. So don't. You cannot throw stones. You gotta fight harder. If you want serious change, you gotta show up. Okay, but with your voice in your.
B
Pocketbook, Let me ask you a question. Okay. Let's just start with California. I said I didn't really want to speak about politics, and now I'm going to go right into the politics because I'm. I am actually furious about what's happened, the demise of California that I've seen so far. Right. Like, I. I moved here when I was 24 years old. I have. Literally five years ago, exactly six, but.
A
Shh.
B
Very close. You're very charming. So I've seen the demise over the. Especially over the last seven, six. Seven years already. The fact that you're saying is absolutely correct. The. It's completely unaffordable. You cannot. Unless you have millions of dollars, you cannot live here. It is unbelievable.
A
True.
B
The homelessness is unbelievable. Like in beautiful areas. Like, I'm living in a nice area, and there's literally homeless people on my street. This is a big problem there. And they're. And they are building homeless shelters, like on very expensive streets. And it's dangerous if you have little kids. I've had my car broken into on my own driveway three times already. This is a problem.
A
Unacceptable.
B
It is unacceptable.
A
So what are you doing about it?
B
And also the business. I mean, like, and. And the taxes are like, through the. What are you.
A
What value are you getting? What value you getting? So it's.
B
It's no value. That's why Mo. Everyone I know has moved to Florida or they've moved Texas.
A
And by the way, those places are not great to live. I've been. I've operated all over the world.
B
My friends who lived, who live in Florida now are loving it.
A
Yeah, go. Go through a hot summer. It's not so.
B
I mean, building. I just got back from there. It's. It's unbearable.
A
It's unbearable.
B
Unbearable.
A
That's what they're paying a price.
B
So.
A
So in California, when I grew up here, yeah. In the. In the late 60s, 70s, 70s, 80s, 90s, there was the land of aspiration. I'm a product of that.
B
Totally.
A
I'm a product of California the way it was. That's why I'm still a conservative Democrat, because conservative Democrats actually ruled the state. Or even the Republicans that were around, they were conservative in the center. People were in the center and just understood this was California with California values, which we have. But we've elected leaders that cannot execute, proven, are not accountable, obviously. Where's the homeless money? Where's the wildfire?
B
Where is it? I'm asking you, where did it go?
A
In the city? In the state? Good. I'D like to, I'd like to propose, which I've done in the past, a bounty. Tell me where it is, I'll give 10% away. Wouldn't you give 10% away of our money to collect 90%? Go find our money. It's our money. It's our money. And these leaders, I can tell you this, they actually think of the reason that I even got involved in doing this, because I don't need to do this. This is just brain damaging. But it's for the good of the future of my children. Your children, our children. And somebody's got to call bullshit on this.
B
Okay, what can you, what, what can you do different? What would you do differently? Every politician or people say, oh, I'm going to do this, this and that.
A
How about this? Execute, be accountable, show results, enforce the law, have respect for.
B
How can you make it more affordable? How can you make it more affordable?
A
How can you get rid of a lot of these insane regulations with regard to human resource law, employment law that are just stifling people from doing business here? Getting rid of the.
B
No movies are even being made here anymore.
A
I've got a solution for that too. Affordability. I would relax or declare an emergency for what's called ceqa, Wildlife Species act and the Coastal Commission till there are better laws so we can survive and thrive. Okay, but we've got to get the individuals in Sacramento taught, coached, counseled with regard to these unintended consequences. They debate, actually, and this happened over the last few months. They were debating a shopping center bill, two and a half hours. And they debated energy policy. Ten minutes. Really?
B
So do you think. Well, number one, do you think, what about Caruso? People like him. Yeah, but you know, he's also a business guy.
A
Yeah, but a Democrat can. It's only going to get elected in the state right now, the way the map looks like the pathway to success. And you know, Rick is a very talented guy, but he's only built things. He's not fixed, broken. Okay? And Rick is not a Democrat. He changed to become a Democrat, but he gave so much money to pro life candidates. I mean, come on, who are you? All of a sudden you had an epiphany that you're. You now believe in abortion and he's Italian, Catholic. What do you talk to God? I mean, seriously. So you have to be authentic to who you are. And once you've given to pro life candidates in your career, you're. You, you believe in a woman's no longer right to choose all of a sudden you change your mind. What happened? Come on. That's not being true to oneself.
B
So you think he's become wishy washy to kind of get the vote?
A
I think he wants to win a beauty contest. Too prompt King.
B
Yeah.
A
It's not a prom king job. No, it's a serious job. We have to roll up your sleeves and serve. You know, Rick, you know, good guy, but he's a Palm beach guy. He's a Republican. All the folks around him are Republican. You are who you hang with. I just call it as I see it.
B
But if you're not looking, would the taxes be lower? Because the taxes here are insane.
A
Me, as a Democrat, can deliver not only a less restrictive environment, but deliver Performance and results. The California Department of Performance and Results. Cpr, which we need.
B
Well, because people here.
A
Cpr. You get it?
B
I know what CPR is, but I'm saying is.
A
Yeah, well, California Department of Performance and Results. Results. You can lower taxes. Over the last 10 years, we've increased the state budget for employees, 45,000 people, which is $6.3 billion.
B
What did you think of Kamala Harris and the whole presidential situation?
A
Oh, it's really simple. She had no iq, no eq, insular, echo chamber. Echo chamber did not understand eggs, bread, milk, cheese, gas, nor immigration policy, which I do. It was so obvious when I saw my young boys, they're in their 20s, and them and their friends going over to Trump. I said, I know this guy. I've sat across the table from this guy. This guy's got no integrity. He's got no values. He doesn't pay his contractors. He's a guy who only wants to be served. He does not serve. And this is who you think is better? Well, yeah, it's better than her because she's never shined the front of a check. Neither did Waltz.
B
Well, the problem.
A
I mean, they're both pathetic candidates. And by the way, on all sides, they're pathetic. They are pathetic. And this is what we've succumbed to. And in California, too, there is not one candidate. I'll go back to this. Why I'm doing this. I shouldn't be doing this.
B
What about. Did you give money to Joe Biden before he, you know.
A
No.
B
Left. No, I say left in a nice way. Before he stepped down, I should say.
A
You did not get money, figuratively or mentally. That was a joke.
B
Yeah.
A
I've known him for a long, long time. He is. And I wasn't the man. He should not have done it.
B
They should have been taken.
A
He should have been taken out and well, look, well, as I said, my adopted father was Harry Reid. I've been trained by Harry Reid and Bill Clinton, my other mentors. Bougie mentors.
B
Yeah, that's a bougie one. That's a nice name.
A
Well, I've got Steve and Elaine Wynn in hotels. I've got Mike Milken since I was 13 and Harry Reid since I was 15. And then Bill Clinton added on. So I come to this discussion with some experience.
B
Bill, think it was a good president? Absolutely.
A
He balanced the, you know, he balanced the budget and showed performance and results.
B
He did.
A
He had reinventing government. If you remember, 400,000 jobs were removed from the federal system and we operated in a budget that was balanced. It was the last time it was balanced. Okay. So I just call it as I see it because it's upsetting to me for my kids future and if I don't participate and call 911 right now for all of your listeners to pay attention to. Okay, you better wake up and you go look at every single candidate that's running for governor right now and say who would you trust with the life, safety of your kids and your family? Who would you trust with the checkbook, your tax dollars of the state?
B
But what about this whole WOKE business? I mean, California.
A
Enough. Enough. No. Enough. It's weak. No breast balls. WOKE doesn't pay the bills.
B
No. Well, I think that's been kind of the demise of what's happened in California.
A
And with all due respect, yeah, we want the climate better for our kids. We do. But at what price?
B
But it's not just about climate. It started maybe with climate. Climate is like a fraction of the pie of what WOKE is about now.
A
Well, that's my point. The whole conversation is not about what it should be. It should be about aspiration, security and safety. Aspiration, affordability, livability, workability.
B
Okay, I'm going to change. I'm going to change into business again because it's. I said I wasn't even going to talk.
A
It's all related.
B
I can go on and on about stuff.
Host: Jennifer Cohen
Guest: Stephen Cloobeck
Date: November 7, 2025
In this milestone 500th episode of Habits and Hustle, host Jennifer Cohen sits down with Stephen Cloobeck, a serial entrepreneur, philanthropist, and founder of Diamond Resorts, which he built into a $3.3B enterprise. The conversation dives into Cloobeck’s journey from nearly broke to billionaire, his core business philosophies, the role of mentorship, his experiences in real estate and hospitality, personal challenges, philanthropic work, and his views on current political and social issues—especially as he prepares to run for governor of California.
Entrepreneurial Roots & Education
“I have no idea how I got through school other than memorizing. Seriously, memorizing everything.” — Stephen ([05:45])
Early Career Moves
"You cannot succeed without mentors. And that's why I pay it forward now." — Stephen ([12:09])
Work Ethic:
Integrity and Brand:
Numbers and Cash Flow:
“The homelessness is unbelievable… Like I'm living in a nice area, and there's literally homeless people on my street.” — Jen ([22:30])
Identifies as a centrist “Reagan Democrat,” and calls out the extremes on both political sides ([19:34]), noting 68% want the “hard center” but lack a clear voice ([19:59]).
Critiques "wokeness" as weakness and a distraction from problems like affordability and safety:
“The wokeness is weakness… Woke doesn't pay the bills.” — Stephen ([20:16], [29:56])
On running for office: Being true, authentic, experienced, and results-driven distinguishes him from political opportunists ([26:36], [27:02]).
| Timestamp | Quote | Speaker | |-----------|-------|---------| | 05:45 | "I have no idea how I got through school other than memorizing. Seriously, memorizing everything." | Stephen Cloobeck | | 10:40 | "Get up early, stay late, go to work with a runny nose. And when they tell you can't do it, believe in yourself that you can." | Stephen Cloobeck | | 10:55 | "Integrity... Don't bust the trust with yourself or with others." | Stephen Cloobeck | | 12:09 | "You cannot succeed without mentors. And that's why I pay it forward now." | Stephen Cloobeck | | 13:00 | "Because you are your brand, right? And it takes decades to build a brand." | Stephen Cloobeck | | 18:08 | "You get to give more money away." (on the difference between millionaire and billionaire) | Stephen Cloobeck | | 19:57 | "68% of us want the hard center. We just don’t have voice." | Stephen Cloobeck | | 22:30 | "The homelessness is unbelievable… I’m living in a nice area, and there's literally homeless people on my street. This is a big problem." | Jen Cohen | | 24:04 | "Go find our money. It's our money." | Stephen Cloobeck | | 27:02 | "California Department of Performance and Results. CPR, which we need." | Stephen Cloobeck | | 29:56 | "Enough. Enough. No. Enough. It's weak. No breast balls. WOKE doesn't pay the bills." | Stephen Cloobeck |
Conversation is candid, direct, and at times irreverent, reflecting both Cloobeck's unapologetically authentic style and Cohen’s forthright curiosity. The dynamic is insightful, supportive, sometimes humorous, and always actionable—delivering both practical business lessons and a sharp critique of current affairs.
This episode offers a raw, practical, and deeply personal look at what it takes to build lasting success—from grit and integrity to lifelong learning and resilience—while also serving as a passionate call for authentic, accountable leadership in business and politics. Whether you’re a budding entrepreneur, an established professional, or simply seeking inspiration to level up, Cloobeck’s journey from broke to billionaire is packed with actionable advice and hard-earned wisdom.