Pod Insights Habits and Hustle Episode 500: From Broke to Billionaire: Stephen Cloobeck's $3.3B Mindset About this episode Stephen Cloobeck didn't climb the ladder. He built his own. In this episode, we talk about what it really takes to grow a billion-dollar company without a business degree: and why integrity, discipline, and grit beat credentials every time.
We get into his biggest pivots, how mentorship shaped his success, and why EQ always outperforms IQ in business and life. Stephen also opens up about giving away over $63 million, calling out "wokeness as weakness," and what real leadership looks like when you're under pressure.
Stephen Cloobeck is the founder and former CEO of Diamond Resorts, which sold for $3.3 billion enterprise value. He's been on Undercover Boss more than anyone, donated millions, and still believes character is the ultimate ROI.
What We Discuss:
02:03 - Stephen's $63 million in philanthropic giving
04:02 - Undercover Boss episodes and giving away the most money
09:30 - Learning business from Mike Milken instead of business school
12:45 - Harvard Business School case study on his industry disruption
15:20 - Treating employees like family as competitive advantage
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Find more from Jen:
Website: https://www.jennifercohen.com/
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Books: https://www.jennifercohen.com/books
Speaking: https://www.jennifercohen.com/speaking-engagement
Find more from Stephen Cloobeck:
Instagram: @stephenjcloobeck https://www.instagram.com/stephenjcloobeck/
Website: https://stephenjcloobeck.com/
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:01 Speaker 00 Hi guys, this is Tony Robbins. You're listening to Habits and Hustle. Crush it.
0:08 Jen Cohen? Before we dive into today's episode, I first want to thank our sponsor Therasage. Their Trillight panel has become my favorite biohacking thing for healing my body. It's a portable red light panel that I simply cannot live without. I literally bring it with me everywhere I go. And I personally use their red light therapy to help reduce inflammations in places in my body where honestly I have pain. You can use it on a sore back, stomach cramps, shoulder, ankle. Red light therapy is my go-to. Plus, it also has amazing anti-aging benefits, including reducing signs of fine lines and wrinkles on your face, which I also use it for.
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1:31 Jen Cohen? Okay, you guys, we have a very special guest here today. We have Steven Klubek. That's how you pronounce your last name.
1:37 Speaker 02 Yes.
1:37 Jen Cohen? If you guys are somebody who is interested in a business, scaling a business, starting a business...
1:42 Speaker 02 Disrupting a business.
1:43 Jen Cohen? Disrupting a business. There's probably, you know, not many people better at it than Steven. He sold his business for $3.3 billion.
1:56 Speaker 02 Enterprise value.
1:57 Jen Cohen? Enterprise value, thank you.
1:58 Speaker 02 Net 2.2 billion.
2:00 Jen Cohen? Net 2.2 billion, that's true. He is exceptionally philanthropic, which is what I like about you.
2:07 Speaker 02 Given away close to sixty three million dollars.
2:09 Jen Cohen? You what?
2:10 Speaker 02 Given away close to sixty three million.
2:12 Jen Cohen? Sixty three? Okay, are you want to, do you have a particular amount that you're trying to get to?
2:16 Speaker 02 No, just very philanthropic.
2:18 Jen Cohen? 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.
2:32 Speaker 02 Tell me.
2:32 Jen Cohen? Okay, so she tells me about Steven and then I'm like doom scrolling on Instagram.
2:38 Speaker 02 How many mutual friends?
2:39 Jen Cohen? And a lot of mutual friends. But you know what came up? Your little clip from the School of Hard Knocks.
2:46 Speaker 02 That was in the street. That was just happened.
2:50 Jen Cohen? That, when did that happen?
2:53 Speaker 02 About nine months ago.
2:54 Jen Cohen? Okay.
2:54 Speaker 02 This young man, 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.
3:01 Jen Cohen? Well, he's been pretty good, too.
3:02 Speaker 02 He's, because he's got a little, nice little platform.
3:04 Jen Cohen? Yeah, he does.
3:05 Speaker 02 For young entrepreneurs and I love young entrepreneurs doing well.
3:08 Jen Cohen? Yeah.
3:08 Speaker 02 And that's how I learned. I learned from great mentors. I never went to business school.
3:13 Jen Cohen? I heard.
3:14 Speaker 02 But I actually got a degree signed by Mike Milken because he taught me. I was fortunate enough to meet him when I was thirteen.
3:20 Jen Cohen? Was this is before junk bonds or after junk bonds?
3:23 Speaker 02 It was during that time. I didn't know. I was studying to be a doctor. I was going to be a surgeon.
3:26 Jen Cohen? Really?
3:27 Speaker 02 I worked at Cedar Sinai for years.
3:28 Jen Cohen? Like a nice Jewish boy.
3:30 Speaker 02 I was going to be the doctor. My brother was going to be the lawyer.
3:33 Jen Cohen? Really? I'm sure your mother was thrilled.
3:36 Speaker 02 They were thrilled, but I didn't become the doctor.
3:38 Jen Cohen? Well, I think you did okay for yourself.
3:40 Speaker 02 But I'm still involved in medical technology and, and research and I still involved.
3:45 Jen Cohen? Okay, wait, let's start from the beginning because people are probably very confused. Okay, so you.
3:48 Speaker 02 Extremely.
3:49 Jen Cohen? You're okay, 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.
3:56 Speaker 02 Which no one's ever done, yeah.
3:58 Jen Cohen? And yet, and you gave the most money away, even on that show.
4:01 Speaker 02 True.
4:02 Jen Cohen? Right?
4:02 Speaker 02 Totally unscripted.
4:04 Jen Cohen? Completely unscripted?
4:05 Speaker 02 Unscripted.
4:05 Jen Cohen? Okay, so there's that. You're also running for governor of California.
4:10 Speaker 02 Unintended.
4:11 Jen Cohen? Unintended, which.
4:12 Speaker 02 Because I interviewed every candidate, not one I would trust with my family's life safety.
4:17 Jen Cohen? Okay, tell me about this.
4:18 Speaker 02 I, I interviewed every single candidate. I mean, I ran tourism in the United States. I don't know if you know that.
4:23 Jen Cohen? No, I don't.
4:24 Speaker 02 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.
4:52 Jen Cohen? It's so funny you did that. Did you grow up wealthy or not really?
4:57 Speaker 02 No, I went to Harvard School for Boys, now Harvard Westlake.
5:00 Jen Cohen? That's well, that's a private school that very fancy.
5:02 Speaker 02 I went to public schools too, when I wrote.
5:05 Jen Cohen? Okay.
5:05 Speaker 02 And I grew up in Encino, Willen 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.
5:28 Jen Cohen? Yeah. By the way, those are, these are not like, these are great schools. These are like Ivy League.
5:34 Speaker 02 I barely got through. I didn't know I was dyslexic.
5:37 Jen Cohen? Well, yeah, I saw that.
5:38 Speaker 02 I negotiated my grades.
5:39 Jen Cohen? How did you negotiate your grades? Sounds familiar.
5:42 Speaker 02 But yeah, so I should have realized I should have gone into business.
5:45 Jen Cohen? Well, how did you negotiate? Like, how did you get in in the first place?
5:48 Speaker 02 Relationship with the, with the professors.
5:50 Jen Cohen? How did you meet the professor?
5:52 Speaker 02 Because at Brandeis, we were very small classes. So of course you knew all your professors.
5:56 Jen Cohen? But how did you get into Brandeis? Because you have to have good marks.
5:58 Speaker 02 I transferred from USC. I was there one year.
6:00 Jen Cohen? Okay.
6:01 Speaker 02 And I did well enough to get in and a relationship helped me. A relationship helped me. And I managed to get through Brandeis. So if you look at my transcript today, it's published my first book, Checking In on Hospitality. It's a concomitant group of Cs, maybe a couple of Bs, one A in human memory. I remember that.
6:23 Jen Cohen? Wow, yeah.
6:24 Speaker 02 No pun intended.
6:25 Jen Cohen? Yeah.
6:27 Speaker 02 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.
6:38 Jen Cohen? Right. It was a different time back then.
6:40 Speaker 02 Different time. So it just powered through everything. Powered through everything, but 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 linearly. You just can handle multi-dimensional chess. 10 games of chess, seven levels out all the time. And that's how I think.
6:59 Jen Cohen? So did you, okay, so did you just like read backwards at the time?
7:03 Speaker 02 It's not reading backwards, it's just not reading, not comprehending.
7:06 Jen Cohen? So it's not retaining the information?
7:08 Speaker 02 No, but I could memorize pages.
7:10 Jen Cohen? Yeah, me too. That was how I got through school too, is memorizing.
7:13 Speaker 02 You're probably dyslexic. You don't even know it.
7:15 Jen Cohen? I just think I'm bad ADHD, like I can't concentrate.
7:18 Speaker 02 So what is it? It's a combination of, but this makes you unique and it gives you a gift.
7:24 Jen Cohen? Yeah.
7:24 Speaker 02 And everyone needs to embrace these gifts that they have.
7:26 Jen Cohen? Yeah, I don't use it as a crutch. I think it's silly.
7:28 Speaker 02 No one has a crutch. There's no crutches.
7:30 Jen Cohen? There are, because we're living in a time when that's-
7:32 Speaker 02 That's because we helicopter our kids.
7:34 Jen Cohen? We helicopter our kids, we coddle our kids. We're not able to let them just be bored. We're not a lot, we're not, we basically do too much for them and they're growing up to be less resilient and have zero coping mechanisms.
7:46 Speaker 02 Where'd you grow up?
7:47 Jen Cohen? Canada.
7:48 Speaker 02 Okay.
7:48 Jen Cohen? Yeah.
7:49 Speaker 02 So Toronto?
7:51 Jen Cohen? Yeah, well Winnipeg first and then Toronto, but I hated school, but I like-
7:56 Speaker 02 How'd you end up in California?
7:57 Jen Cohen? Job opportunity.
7:59 Speaker 02 That's great.
7:59 Jen Cohen? Record label. My whole situation is 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.
8:11 Speaker 02 So do I.
8:11 Jen Cohen? Yeah. 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 Bs in front of your money than I do. You have way more money than I do, but besides that-
8:27 Speaker 02 I just, I just happen to take a lot of risk.
8:30 Jen Cohen? Listen, risk doesn't always work out, right?
8:33 Speaker 02 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.
8:41 Jen Cohen? 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?
8:53 Speaker 02 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.
9:01 Jen Cohen? Okay.
9:01 Speaker 02 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.
9:10 Jen Cohen? Okay.
9:10 Speaker 02 And they promised me a bonus, which they didn't pay me. So I started my own company at 24.
9:16 Jen Cohen? And what was it? Where does it begin at?
9:17 Speaker 02 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, not the down, and built a Chief Auto Parts and four stores.
9:33 Jen Cohen? So wait, so you started off in like real estate development, basically?
9:36 Speaker 02 Shopping center development, leasing, managing, building, operating. And then from that point, built shopping centers throughout Southern California, hand for 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.
10:05 Jen Cohen? So that's how, so then you ricocheted into that from like the shopping malls to the one hotel?
10:12 Speaker 02 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.
10:23 Jen Cohen? Who lent you money at the beginning?
10:25 Speaker 02 Oh, we had credit, credit companies.
10:26 Jen Cohen? So you did all the, you did like?
10:28 Speaker 02 But before that was savings and loans. And at that time, there was so much money available, they would.
10:33 Jen Cohen? It was a different time.
10:34 Speaker 02 But you had to sign personally. So I had the risk of going bankrupt on every project.
10:38 Jen Cohen? Wow.
10:38 Speaker 02 And I almost did on one, that one in Lee. Forest, California, but I had a very successful project in Mission V A O 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.
10:52 Jen Cohen? Well, how, okay, so the, I guess my first question is, how does, I think a big thing is people don't know, they, they think because they don't have the, the means, the connections, all the things like that. How does, what is the first step to starting that?
11:07 Speaker 02 What's the name of your show?
11:09 Jen Cohen? Habits and Hustle.
11:11 Speaker 02 Hustle.
11:12 Jen Cohen? 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?
11:19 Speaker 02 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.
11:26 Jen Cohen? What is the one skill or the one quality that is essential for an entrepreneur to be successful?
11:34 Speaker 02 Integrity.
11:36 Jen Cohen? Integrity, okay.
11:37 Speaker 02 Integrity is it, 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.
11:58 Jen Cohen? So you've had this, so you went from that one hotel to, how many did you end up?
12:03 Speaker 02 Ended up having 432 and 35 countries.
12:06 Jen Cohen? They're called Diamond, they were called?
12:07 Speaker 02 It was Diamond Resorts. Originally, the company was called Santara. 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.
12:17 Jen Cohen? Wow.
12:18 Speaker 02 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 on the documents. Now, mind you, when I was doing this, I didn't know anything about public companies. I was a private entrepreneur.
12:30 Jen Cohen? Right.
12:30 Speaker 02 And I was now delving into the world of public company, S E C, 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.
12:48 Jen Cohen? You think so?
12:48 Speaker 02 Huge. You cannot succeed without mentors. And that's why I pay it forward now.
12:52 Jen Cohen? How many people do you mentor right now?
12:54 Speaker 02 Oh, dozens of young adults.
12:56 Jen Cohen? Really? What kind of how, what kind of mentor are, how involved are you as a mentor?
13:00 Speaker 02 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.
13:19 Jen Cohen? Really?
13:19 Speaker 02 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.
13:32 Jen Cohen? What, what is, um?
13:33 Speaker 02 So integrity is very, very important.
13:36 Jen Cohen? Keep on talking. I'm just going to open my questions for you. So go ahead.
13:39 Speaker 02 Everything's integrity is just a key, key component part of success. Because you are your brand.
13:46 Jen Cohen? Right.
13:46 Speaker 02 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-veterolic 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.
14:27 Speaker 02 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.
14:36 Jen Cohen? Yeah.
14:36 Speaker 02 Ecclesiastes 412.
14:38 Jen Cohen? I think I saw you.
14:38 Speaker 02 Pretty good for a Jewish boy.
14:39 Jen Cohen? Yes, not bad at all.
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16:33 Jen Cohen? You're big on the meaning, like the word yes, like the meaning of yes.
16:37 Speaker 02 That's what I found lacking in the hospitality space, and I was able to disrupt that.
16:41 Jen Cohen? Okay.
16:42 Speaker 02 And I marked that.
16:43 Jen Cohen? Tell me.
16:43 Speaker 02 The 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.
17:05 Jen Cohen? What did your dad do for a living?
17:07 Speaker 02 He wasn't, he was Glenn Gary Gunn Ross. You ever watched that movie?
17:10 Jen Cohen? Yeah, she's a salesman. Is that the guy?
17:12 Speaker 02 Alec Baldwin, he was that guy. He was ABC Coffees for Closers. That's my father.
17:16 Jen Cohen? Really?
17:17 Speaker 02 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 finance school. He was a cash guy.
17:30 Jen Cohen? Yeah.
17:31 Speaker 02 He didn't understand the generally accepted accounting principles and he just dealt in cash.
17:36 Jen Cohen? Did your mom work?
17:37 Speaker 02 No, no.
17:38 Jen Cohen? Did your, how, do you have any brothers or sisters?
17:41 Speaker 02 I, I do, but we got into a massive argument years ago. They busted my trust. So it was over money.
17:48 Jen Cohen? Of course, it's always over.
17:48 Speaker 02 Sure, they didn't want to work, you know?
17:51 Jen Cohen? So wait, so.
17:51 Speaker 02 They're doing silly things.
17:52 Jen Cohen? Wait, so you have a brother or a sister or both?
17:54 Speaker 02 Both, both.
17:55 Jen Cohen? Older, younger?
17:57 Speaker 02 What's that?
17:57 Jen Cohen? Older?
17:58 Speaker 02 Younger, both younger.
17:59 Jen Cohen? So you don't talk to them?
18:00 Speaker 02 No, no, they decided to sue my wife and my, myself and my children years and years, decades ago.
18:08 Jen Cohen? For money?
18:09 Speaker 02 For money. It's ridiculous. So I wrote him a check and said, goodbye.
18:12 Jen Cohen? You, why, why did you write them a check?
18:14 Speaker 02 Because I would rather not have the conflict. Just make difficult situations go away.
18:20 Jen Cohen? Even though that's your money?
18:21 Speaker 02 I took his interest in the company.
18:23 Jen Cohen? Oh, well, you guys are partners?
18:24 Speaker 02 Yeah, we're partners. So I took his interest. So I just bought him out.
18:27 Jen Cohen? Oh, gotcha. Okay.
18:28 Speaker 02 Bad mistake on his part.
18:30 Jen Cohen? Wow. And what year did he leave the company?
18:32 Speaker 02 Oh, it was decades, probably two decades ago.
18:34 Jen Cohen? Oh.
18:34 Speaker 02 Five years ago, a long time ago.
18:36 Jen Cohen? Cause when did you actually sell this company?
18:38 Speaker 02 Two thousand sixteen.
18:39 Jen Cohen? So.
18:39 Speaker 02 September.
18:40 Jen Cohen? So you went from like, so you were obviously like, what's the difference between being a millionaire than to being a billionaire?
18:47 Speaker 02 You get to give more money away?
18:49 Jen Cohen? Besides giving more money away? Well, how did your lifestyle change?
18:53 Speaker 02 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 to do it.
19:02 Jen Cohen? Right.
19:03 Speaker 02 It's like a mini hotel, but I built it for events and, and to do charities and politics and policy. And I did it for my dream.
19:13 Jen Cohen? Right.
19:13 Speaker 02 I always wanted to live in Beverly Hills, so I wanted to live over the hill.
19:16 Jen Cohen? Where were you living before two thousand sixteen?
19:19 Speaker 02 Uh, before, uh, before thousand, two thousand sixteen, I was living in Las Vegas and I had a home in Cabo. I had a beach house on Laguna Beach.
19:25 Jen Cohen? Oh, okay.
19:26 Speaker 02 I had many homes.
19:27 Jen Cohen? So then you, you built this house in Beverly Hills once you made the money? The real money.
19:32 Speaker 02 Yeah.
19:32 Jen Cohen? Yeah, the real money. Besides that, because I see you have a security guard. You did you did like, did you get the security?
19:38 Speaker 02 I have 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.
19:54 Jen Cohen? I wanted to ask you about that.
19:55 Speaker 02 Oh, it's serious.
19:56 Jen Cohen? Tell me, give me some information about that.
19:58 Speaker 02 Three death threats already.
19:59 Jen Cohen? Really?
20:00 Speaker 02 Yeah, anti Semitic death threats.
20:03 Jen Cohen? I'm surprised it's only three.
20:04 Speaker 02 People in politics and policy, you know, I'm so in the middle, hard center. I'm old Ray, I'm a Reagan Democrat, balance sheet, income statement, we don't steal.
20:12 Jen Cohen? Yeah.
20:13 Speaker 02 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 some people don't want to hear the truth. And today with the vitrolic politics and policy we have today, you only hear from the hard right and the hard left, so they both want to demolish me.
20:36 Jen Cohen? Well, it's interesting because.
20:38 Speaker 02 But 68% of us want the hard center. We just don't have a voice.
20:41 Jen Cohen? Well, that what I was going to say is that that's like, I kind of feel that what used to be considered debt, like the Democrats are is not the same thing anymore.
20:49 Speaker 02 I'm still the same.
20:50 Jen Cohen? Right, but the people who were Democrat, it's the, the party has changed a lot over the last.
20:55 Speaker 02 Yeah, that wokeness is weakness. It's weakness, it's weakness. They have no breast balls, they have no breast balls and they forgot about the customer.
21:04 Jen Cohen? 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.
21:15 Speaker 02 As I was moving back home, all my friends were leaving or have left.
21:20 Jen Cohen? Left.
21:20 Speaker 02 And their children can't afford to live here.
21:22 Jen Cohen? There's a lot of problems.
21:23 Speaker 02 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.
21:33 Jen Cohen? Yep. The fact that she's still even a mayor, first of all.
21:36 Speaker 02 Well, how about the accountability? How about, how about, how about the wildfire money? Governor and Mayor Bass, where's the money?
21:43 Jen Cohen? I'm at what you tell me.
21:44 Speaker 02 Where's the money? Well, it's probably given to charities, on charities, on charities, and it's all. Filtered off through G and A with side deals, which should be investigated. Okay. I mean.
21:55 Jen Cohen? This happened, do you remember like a few years ago? Sure you do Gavin, everyone hated Gavin Newsom back then. Everyone hated him and then he got reelected. It was shocking to everybody else, like everybody was shocked when he got reelected again.
22:09 Speaker 02 Because, look, you cannot blame anybody other than we.
22:14 Jen Cohen? Okay.
22:14 Speaker 02 We did it.
22:15 Jen Cohen? Well, not we, but somebody did it.
22:18 Speaker 02 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.
22:27 Jen Cohen? Okay.
22:27 Speaker 02 With your voice in your pocketbook.
22:29 Jen Cohen? 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. Cause 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.
22:45 Speaker 02 Five years ago.
22:46 Jen Cohen? Exactly six, but 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.
23:09 Speaker 02 True.
23:09 Jen Cohen? 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.
23:33 Speaker 02 Unacceptable.
23:34 Jen Cohen? It is unacceptable.
23:35 Speaker 02 So what are you doing about it?
23:36 Jen Cohen? And also the business, I mean, like, and the taxes are like through the, what are you paying for?
23:42 Speaker 02 What value are you getting? So it's.
23:43 Jen Cohen? No value, that's why everyone I know has moved to Florida or they've moved to Texas.
23:48 Speaker 02 And by the way, those places are not great to live. I've been, I've operated all over the world.
23:53 Jen Cohen? My friends who lived, who live in Florida now are loving it.
23:57 Speaker 02 Yeah, go, go through it, a hot summer.
23:59 Jen Cohen? I mean, I just got back from there. It's unbearable.
24:02 Speaker 02 It's unbearable.
24:03 Jen Cohen? Unbearable.
24:04 Speaker 02 Well, so they're paying a price.
24:05 Jen Cohen? So.
24:05 Speaker 02 So in California, when I grew up here.
24:07 Jen Cohen? Yeah.
24:08 Speaker 02 In the, in the late sixties, seventies, seventies, eighties, nineties. It was the land of aspiration. I'm a product of that.
24:15 Jen Cohen? Totally.
24:15 Speaker 02 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 money?
24:41 Jen Cohen? Where is it? I'm asking you where to go.
24:42 Speaker 02 In the city, in the state? Good. Well, 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.
25:13 Jen Cohen? Okay, what can you, what, what can you do different? What would you do differently? Cause people, every, every politician or people say, oh, I'm going to do this, this and that.
25:20 Speaker 02 How about this? Execute, be accountable, show results, enforce the law, have respect for all the customers of California.
25:29 Jen Cohen? How can you make it more affordable?
25:30 Speaker 02 Get rid of, 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.
25:42 Jen Cohen? No movies are even being made here anymore.
25:44 Speaker 02 I've got a solution for that too. Affordability, I would relax or declare it an emergency for what's called SEQA, Wildlife Species Act, and the Coastal Commission until 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 10 minutes. Really?
26:17 Jen Cohen? So, do you think, well, number one, do you, what about Caruso? People like him.
26:22 Speaker 02 Yeah, but, you know, look-
26:23 Jen Cohen? He's also a business guy.
26:24 Speaker 02 Yeah, but a Democrat can, is 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 fix 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, you, you believe in a woman's no longer right to choose. All of
27:06 Speaker 02 a sudden, you change your mind? What, what happened? Come on. That's not being true to oneself. Okay?
27:12 Jen Cohen? So you think he's become wishy-washy to kind of get the vote?
27:15 Speaker 02 I think he wants to win a beauty contest, too. Prompt King.
27:18 Jen Cohen? Yeah.
27:19 Speaker 02 It's not a Prompt King job.
27:20 Jen Cohen? No.
27:21 Speaker 02 It's not a, 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.
27:35 Jen Cohen? But the fees are Republican. Would the taxes be lower? Because the taxes here are insane.
27:41 Speaker 02 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.
27:52 Jen Cohen? Well, because people here-
27:53 Speaker 02 CPR, you get it?
27:54 Jen Cohen? I know what CPR is, but I'm saying is-
27:56 Speaker 02 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.
28:10 Jen Cohen? What did you think of Kamala Harris? Are you, and the whole presidential situation?
28:14 Speaker 02 Oh, it's really simple. She had no IQ, no EQ. Insular. Echo chamber, echo chamber, didn't 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 twenties, 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. 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 shot in the front of a check. Neither did Walz.
28:52 Jen Cohen? Well, the problem is-
28:53 Speaker 02 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 succumb to. And in California, too. There is not one candidate. I go back to this. Why I'm doing this? I shouldn't be doing this.
29:05 Jen Cohen? What about, did you give money to Joe Biden before he, you know?
29:11 Speaker 02 No.
29:11 Jen Cohen? Left?
29:12 Speaker 02 No.
29:13 Jen Cohen? I say left in a nice way, even before he stepped down, I should say. You did not give money to him?
29:17 Speaker 02 Figuratively or mentally?
29:19 Jen Cohen? Mentally.
29:20 Speaker 02 That was a joke.
29:20 Jen Cohen? Yeah.
29:21 Speaker 02 No, I've known him for a long, long time. He is not, wasn't the man. He should not have done it.
29:25 Jen Cohen? They should have taken, they, what?
29:26 Speaker 02 He should have been taken, 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.
29:35 Jen Cohen? Oh.
29:35 Speaker 02 Bougie mentors. Yeah.
29:36 Jen Cohen? That's a bougie one. That's a nice name.
29:38 Speaker 02 Well, I've got Steve and Elaine Win 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.
29:49 Jen Cohen? Bill Clinton was a good president, actually.
29:51 Speaker 02 A plus. He balanced, you know, he balanced the budget and showed performance and results.
29:55 Jen Cohen? He did.
29:56 Speaker 02 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?
30:31 Jen Cohen? But what about this whole woke business? I mean, California-
30:34 Speaker 02 Enough, enough, no, enough. It's weak. No, brass balls. Woke doesn't pay the bills.
30:40 Jen Cohen? No, well, I think that's been kind of the demise of what's happened in California.
30:43 Speaker 02 And with all due respect, yeah, we want the climate better for our kids. We do. But at what price?
30:49 Jen Cohen? But it's not just about climate. It's started maybe with climate. Climate is like a fraction of the pie of what woke is about now.
30:58 Speaker 02 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.
31:10 Jen Cohen? Okay, I'm going to change, I'm going to change into business again because I said I wasn't even going to talk about politics.
31:15 Speaker 02 It's all related.
31:16 Jen Cohen? I can go on and on about this stuff.
Previous Episode 499: Kim Perell: Building a $235M Company from the Kitchen Table + Why Perfectionism Kills Success Next Episode 501: Alejandra Maria Gallo: Dating Strategy, Emotional Regulation, and Taking Your Power Back Page updated October 31, 2026 · transcript and summary are machine-generated
