Shark Tank Secrets, Smart Money Moves, and My Real Relationship with Mark Cuban l Full Send Podcast

[Music] All right, we got another great episode. We got, uh, Kevin O'Leary in the house. Shows up in style, what an hour and a half early, and crushes three Happy Dads right upon entrance. Two watches, too. Two watches! You got to have two watches; otherwise, you don't know what time it is in New York. You got East Coast and West Coast—LA time, New York time on each wrist, that's how you do it. Plus, you want to show your pieces, right?

How many watches do you have? I got a lot of watches. I got a lot of watches. And so, because I've been ripped off twice—two different heists—I don't talk about how many I have or where they are. But I did get me to start a watch insurance company; that motivated me to do that. I'm a big watch collector. I believe in horology; I think it's an art—no different than modern art. It's very collectible, and it's been a great appreciating asset.

What's your favorite piece that you have? You know, that's a big debate. Everybody around in LA loves AP, a lot of Rolex bling here, and Patek, of course. But right now, the number one brand on Earth—the most collected watch, the most coveted piece, because he's still alive—is FP Journe. Yes, he is the Picasso of watchmaking. So, if you could have bought a Picasso in the early '50s from Picasso and just held on to it—think about that investment. So, that's how watchmakers think about Jan. Getting a piece from him, he's a very eclectic guy. Every piece he makes, he wants to know who's getting it, why they should get it, why they deserve it. It's a very interesting community, and people from around the world.

You know, in a way, it's a curse for me because I get calls from all around the world, and people just grind on me. "I need a Journe! You got to talk to FP." It doesn't work that way; it just doesn't work that way. You have to earn your status as a collector, 'cause the last thing he wants is to sell you a piece for $18,000, which is his entry level, and then you flip it for $420,000 the next day. That really pisses him off.

Yeah, I've seen they’re reselling like crazy right now; they're hard to get. Yeah, but that's one of the only brands that's holding its value—watches are down about 28% worldwide, except Journe. Jan only goes one way—up. How do you get on the list? You got to interview; you got to go meet them and tell them why you deserve it. If you're not willing to spend three interviews, don't bother.

What's the care? Who you are, how much money you have, or your royalty—whatever it is, doesn't matter. Why do you deserve the next Jan that's being made by one guy in Switzerland right now? Why you? You should go interview for that.

Yeah, that's good. Can you give me an interview? Get him in the door where you can sell himself. But are you a collector? Yeah? Okay, I can get you the interview, and you have to explain to them why you deserve one and why you'd be a great ambassador for like—that's the whole idea. And of course, what are you wearing there?

Rolex? Yeah, yeah, these very nice pieces. I noticed a bunch of good watches around here—Daytona over there.

Thank you. Whoop? Now, whoop sucks.

Whoop's dope! What do you mean? Listen, how does whoop suck? Not only is it ugly; it's an Aura—that does a much better job.

No, it blows. That doesn't show you workouts, though.

Are you kidding? Look, first of all, you're wasting space; you could have a real piece there. Instead, you have a whoop. I don't think Aura rings are sauce.

What? What? The guy walks in the room, and he's 20% off retail right away; he's got a whoop on. Who reps an Aura ring, though? Come on, an AA ring? Everyone reps whoop—like athletes. Ronaldo? No one's rocking an AA ring. I bet you they're paying him to wear that because Ronaldo would rather wear a whoop.

Yeah, that's a listen. I know the whoop guy; he plays squash in Boston. Great guy. But when you're giving up wrist space where you could put a piece—where you could really put a piece of art, like a watch—and you put a whoop there, I mean, I think you walk in the room, and people are just doing this—like they can't believe it.

I love whoop—two wrists, two watches. While we're talking about watches, William Woods—you've never heard of this guy. He's a watchmaker that wants to honor first responders from all around the world that risk their lives—firefighters buy these watches everywhere.

This is actually a fire hose; it smells of smoke.

Can I see it?

Yeah, absolutely. Read the back; you'll get a kick out of this. It's a beautiful piece, very rare.

What did that run you?

That watch is probably available right now for about 6K. It's not that it's not crazy expensive, but if you talk to a firefighter in England or in Ireland or 911 responders, these guys wear this watch. I thought 9/11 today we'd honor them; that's why I wore the piece.

And I just want to shout him out—William Woods, incredible watchmaker. Really motivated around supporting first responders. Met him this year at Watches and Wonders in Geneva. Check the back; it's kind of a…

So what makes watches so special is just the fact that like there's only so many. I love dials, though—I mean, I'm a dial guy.

You know, the dial? Yeah. Or just is it the fact that there are so few of certain ones?

Yeah, yeah. I have a lot of Peace uniques, you know. Real watch collecting is when you can convince the maker or the brand to make you a one-of-a-kind watch because they respect you as a collector.

I'll give you an example on the other wrist, and I don't think I've talked about this to anybody, but this is a watch made by Rolex, actually their division Tudor, in silver, for the first 23 people that worked on the pilot here in LA 16 years ago in this studio that day on Shark Tank. If you were in the studio and you were a tech, or you're on the—in front of the camera, behind the camera, or a lawyer, or whatever, a hair and makeup artist, and you were there that day and you're still working on the show, Rolex made this piece for you. Tudor made this in silver for you with your name on the back, unique serial number and the Shark Tank logo on it, and they did that for you.

Well, they made it for 23 people, including me. I sponsored this project, okay? So getting the logo out of Sony took two years. Now, when I said to them, "Listen, I'd like you to make a couple of extras," they said, "No, we need to know every single name of every single person and we need proof that they were there." It's a Founder Series; this watch is priceless. You'll never get another one with your name on it. So we're having a special ceremony this year, awarding them on the 16th here in LA to every individual. I'm going to fly in; the guy from Rolex is coming in to present each one at a time.

Can you imagine getting your own piece with your own name on it? Sauce! Silver changes its patina over time on your body chemistry, so everyone will look different a decade from now.

This is hot! My friends, I mean, you come in here trying to flex—oh, heavy flex, two watches. Look, I love... didn't know we were going to start out that hot, but I love this kind of crap.

I really do. Do you collect—do you collect anything else?

I do, actually. I got to hear it off—you got some crazy baseball card or something?

For sure. Baseball's interesting these days—collectibles, right?

Yeah. Did you get into that?

Yeah, no, I've done some stuff in that space. You know the show that happened in Cleveland a few weeks ago? You know what I think about that space right now? It's early times because you've got pricing on Jordans past 3 million, but you got a lot of fraud. You know, a lot of wax you open up is... [ __ ] it's fake. Guys put these things together and there are [ __ ] cards in there.

What I don't like about that is you've got fathers and sons all around America buying these things and getting ripped off, and that pisses me off. So authentication is going to matter. Vaulting is going to matter. It's a space I'm looking at; but hate it when there's [ __ ] artists ripping people off, and that's kind of what's going on in that space right now, and I think it happened a couple of times in Cleveland last week, two weeks ago.

So there's a big collector in there named Shine; he's pretty famous. He's been ripped off himself a few times, and he's sort of an advocate for cleaning it all up. But I mean, it's a very interesting space 'cause it transcends, you know, obviously what's going on with Fanatics, bringing together celebrity, sports, collectibility, investing—very interesting. And Michael Rubin's kind of the guy right now.

He is the guy, he is the guy. He was a guest shark, by the way. I met him.

Oh yeah? I saw that! How was that?

I loved him. No [ __ ] guy, I mean, you get the feeling he'd rip your heart out if you lied to him—like, I just loved him. He was just great. He was great on Shark Tank; he should come back.

He invited me to his white party, and that was a watch event like I'd never seen.

Did you go?

Oh yeah! How was it?

I wanted to bring my... you know, this was a watch contest every—like, you know, Jay-Z, Brady, and I thought, "What could I wear that could totally kick ass at that party?" Because that's really what that thing was about—you walk in with your watch. I brought the Cier Crash. Nobody had one, and so when I saw Brady, because I know him, and I said, "You know Brady, I think I kicked your ass today," he said, "No, no, no, no. I have a one-of-a-kind AP with the Super Bowl wins at the 11:00 mark," and I went, "Oh, that's when I lost!"

That game—that's, I came in number two. So Brady screwed me—that was it! But up till then, I was winning. But that's the kind of stuff I love.

Do you judge people off what they're wearing?

I don't. I judge them on whether they're collectors or not. You know, if you're just wearing a watch 'cause you want bling, you're not a collector. But if you really appreciate the art, and you're buying to collect, I appreciate you. You're an art collector.

What's the difference? Modern art watches—same thing.

So I don't judge them on what they're wearing.

Who's the biggest watch collector you know?

Royal family, United Arab Emirates.

Oh [ __ ] yeah. I thought I was the biggest watch collector in the world; I'm dog [ __ ] compared to those guys. They have pieces—they have a room this size with drawers in it. It's just one room. They have watches from, you know, vintage, etc. I have a lot of respect for them because they collect it for art, and they don't boast about it.

I wouldn't know that unless one of them just contacted me, said, "Come over here, we'll show you some watches." We respect as a collector. I couldn't believe what I saw, and I really realized where I am in the pecking order.

You're always serving somebody else. No matter how you think you are, there's somebody else richer—there's somebody else bigger. And that's really something I've learned—you got to be humble because no matter how good you think you are, there's somebody better. And it lets you think about getting better yourself. You're never the king, never.

Well, it's hard to compete with those guys. I mean, they own like the whole oil of a country, right?

They don't think that way anymore, I have a lot of respect for them. They've diversified their economy so much. They have really done something that—that's a 52-year-old country, 52 years old.

Well, they're doing it right over there. Yeah, they basically have taken the best of every country in the world and put it in one place. There's no place like Abu Dhabi. There's no place like Dubai, no place.

I mean, when I first went there, I couldn't believe it; I just thought, "How can they have done this in 52 years?" We go every year for the UFC fights there, so we've been two or three times too.

It's incredible. Pepsi Center, right?

Um, or the Coke Center.

It's in Abu Dhabi—it's in Abū Dhabi.

Yeah, it's amazing; I mean, it's amazing. I love that place and I go there quite a bit. I'm doing business with those guys; I love them. And, um, I just have a lot of respect for what they've done.

You think the Middle East is like those kinds?

Same thing. Guar. Obviously, it's a sad thing that it's in such chaos right now, in Gaza and Israel— that's really sad. But the potential of that region is, uh, is very good.

So when you say that— that couldn't have been your first humbling moment though, seeing their watch collection, right?

I got a phone call from one of the collectors, um, five or six years ago, who I didn't know, and he texted me and said, "I hear you're in New York," and I said, "Yeah." He said, "Look, um, I—I didn't know who FP Journe was." He said, "I'm a—you know, he was one of the royal family members of the UAE, and he said, 'Why don't you mos over to their boutique?'"

I said, "I don't even know who Journe is." And he said, "I'll get you an introduction. They have their big global dinner tonight; I'm going to get you an invite to dinner." So I went there, and I met him through this connection, and that's the beginning of our friendship. And then I went over to see him in Abu Dhabi, and we became close friends, but he's also a minister in the government, and that's how we kind of... he— you know, we started our relationship through watches.

Watches are a way to build your community around the world 'cause other collectors respect you. He saw some Instagram video I did or something, and we've been close ever since, and that drew me into business there. That's what happened.

It's crazy to talk to about the gym. What, just a good place to... yeah, network?

No, it's networking. You know what? One of the things I've learned, we should let's parlay this conversation into something. I'd like to tell people because I teach a lot now, um, young entrepreneurs. And I'm beginning to realize that a lot of people are confused about what it takes to be successful. And I don't mean just money.

You know, it's not—I don't get up in the morning and say I want to be richer. I don't give a [ __ ]! I don't need any more money. But you don't get rich pursuing the greed of money; you get rich because you're passionate about something. It's a business you start; you're willing to work 25 hours a day, eight days a week. And then one day, we wake up, and you're filthy rich.

And the benefit of that is freedom to do whatever you want. You want to buy a watch, you can do it. You want to buy a car, you can do it. You want to take your family somewhere, you can do it. But mostly, what happens—and this is kind of interesting—I don't care who you talk to; you just work harder.

You've definitely had experiences, and it sounds like it can be personal. But when have you, like, been burned or overpaid, or when have you overpaid for something that's pissed you off?

I don't overpay for anything; that's never one time.

Yeah, no, no, no. I've been— listen, I've made mistakes. But let me tell you a lesson my mother taught me, and I saw it happen because she's passed away a long time ago. She—you know, we were not a wealthy family, but she loved Chanel. She was crazy about Chanel women's clothing—jackets and, you know, skirts—Chanel, Chanel, Chanel. That's really expensive.

But she, rather than buy five dresses a year, she bought two Chanel jackets a year—that's it. When she passed away, there was a cat fight in my family amongst the women for those vintage Chanel jackets, which had appreciated in value over decades. Classic vintage Chanel is a big deal for women because they still look spectacular; it's classic fashion. And that kind of taught me something: buy good [ __ ]—buy less good [ __ ]—and you know, instead of more crap.

So, buy a good pair of sneakers—buy the best, buy the best suit you can buy and keep it because it's, you know, rather than 40 pieces of [ __ ], buy two good things. Same philosophy with watches, same thing with cars, same thing with guitars. I like good [ __ ] and it goes up in value.

I have a question. You mention about saving money until then being a millionaire when you're 60. Most people probably want to be a millionaire when they're younger. For you specifically, at what point did you start to see real financial success, and what were you doing? Like, what was the first thing that really changed?

Yeah, that's a good question. I was never chasing money, but I became a millionaire when I was pretty young because I took my company public. Probably made my first million when I was 26.

Once you make your first million, the hardest thing to do in the world is make the first million. Then the hardest is to make the next four. So you have 5 million once you have 5 million liquid in the bank; you're set for life. You can survive anything at five. But once you get to five, it's really easy to get to 50—that's what happens.

I know it sounds TR, but it's true because you start investing, and you start multiplying that capital. Once you're at 50, there's no holding you back. And so, really what I'm saying is getting the first million is the key to success, and the way to get the first million is don't be stupid. Like, figure out, what is it? What do I got to do to get the first—

And I'm talking a million liquid dollars in the bank, not a million in AP watches or a million in a house. I'm talking about cash—a Reno in the bank. Liquid cash that if the [ __ ] hits the fan in your life, you have it there. That's not enough, but five is. No matter what happens in your family, and you've got 5 million liquid, making right now 5% in the bank, that's not bad.

Then you have all the rest of your stuff. You're taking risks, but I always have that cash, a Reno in there, and I never let that nest egg go anywhere. And I've met lots of people that feel the same way about it. But when you're young, if you can get the first million by the time you're 30, you're going to do okay.

Now, people say, "I'm going to get it when I'm 23." Not so easy! You're just getting out of college; you haven't really figured yourself out yet. You should be an apprentice somewhere. It feels really good to look at that account today; it's got all those zeros on it. Like, I remember looking at it, saying, "Wow! How do I do this?" And then after that, I never look back—I never looked back.

And, uh, now it's not—I don't know, it's just not that big a deal. I mean, it's just—that's not what I care about. I don't care about that. I mean, I don't want to waste money, but that's not what motivates me. I'm looking for interesting stuff to do, work with entrepreneurs, just do interesting stuff.

Yeah, you know, just find things that I'm— I find things that are not in my comfort zone that I've, you know, like, yeah, I know how to tape Shark Tank. I've been doing that for 16 years. I really enjoy it. I like investing in entrepreneurs, but I've never done a movie. I've never been a scripted character.

Well, that's about to change.

Change? Ooh, and I'm— I'm going to try that.

What is—what's your role?

I can't tell you; I'd have to kill you. But I'm—you’re going to see it soon, okay?

What would be your dream role?

My dream role is to be a billionaire in the '50s, in the emerging America at a time of extreme volatility, anxiety. The World War II was just over—U opportunity—no phones—all that. Imagine New York City, 1948; what that must have been like to be in that world when the world was your oyster and America was just gelling? I would like to go back in time.

I don't think that's that challenging of a role for you, though.

Well, we'll see. You know, I've never—I've never... Great Gatsby was 1920, yeah? When was Great Gatsby? What was that?

No, no, listen, listen! You—I’d love to tell you because I've been working on this project now for a few months. I was at Avra last night, reading my script—oh, I love Avra!

Yeah, I love it! I'm sitting at the bar, eating oysters, drinking Chablis, reading the script for the 50th time. So you got to know your lines! But we start shooting this thing at the end of this month in New York and in other cities. I'm very excited; I have never done this before, but I am motivated, and I'm just—I can't wait to do it.

That I can see! I'm really thrilled because it's just a—you know, that's what I mean. You want to find projects like that that are extremely different than what you do; you want to keep interested. You want to stay young; you want to stay motivated. You want to get up in the morning, find stuff that is not in your comfort zone that you've never done before. Otherwise, it's the same stuff you're always doing, and I think that that gets me very jazzed to go and, you know, work on it and spend the time on it. And, uh, I'm just thrilled to do it.

Did you feel this way about the first company that you took public? Did you feel that way then?

Mean that I'm talking about it?

No! The first company that you had major success with.

Oh, that was years ago. Did you—did you feel that way about that project?

Yeah, yeah. I mean, I— I remember, I mean, we—that thing was—that was in the '80s. I mean, it was a long time ago, but I've done so many—you know, you do transitions. You're an operator. Like when you found a company, you're an entrepreneur and you operate it, and you build it, and you hire people, and you go through all those trials and tribulations.

And then, once you sell, you become an investor. You're not the same; you're not running the business. You're finding people to do that with you and for you, and that's a different role.

Um, and you make a lot of mistakes. I mean, I've had some great investments, and I've made some really bad ones too. But, you know, that's V—you’re investing—you think it's going to be great. That's—you know, think about Shark Tank. I'll do 10, 12 deals this year—I'm shooting it right now.

We're all sitting in LA; I'm shooting it. You know, and the ones that I think are the very best turn out to be do [ __ ], and the ones that I think, "Ah, this is just a funny TV deal," I make millions off. You just don't know! It's so serendipitous, so unusual, so unique.

And I use—I have a great example of one. A few years ago, this woman comes on the set of Shark Tank—Ana Skaya, Ana Skaya was her name—um, entrepreneur. And she comes out with a cat and a Q-tip, and she says, "Listen, I have made a cat DNA testing kit for cats that can extend their lives for $29.95." And everybody looked at her, and I said to her, "Why would I ever buy that when I got buy a new cat for five bucks? Why would I?"

I've seen that episode!

Yeah, yeah, yeah! She said, "You don't get it! This is data; this is a data company. You swab the cat, you send in the swab, we gather the data; there’s 110 million cats in America, and we start to learn what diseases they're suffering from, around what cluster of DNA." And I thought the whole thing was total [ __ ]! But she was so compelling.

Oh, she was a beast! She wouldn't leave there without the 200—200—without the 250 grand. So I finally said, "I can't take it anymore! I'll give you the 250 just to get you out of here."

That was my best investment ever! The thing sold for a fortune for the data because I didn't see it at the time, but she saw it.

So now these pet companies, big pharma, wants to help you extend your cat's life to the 30th year. You can do that with a cat if you give them the right food because they die of abscessed teeth and brain hemorrhaging—all this crap from feeding them shitty food based on their DNA.

There's only three big pools of DNA—like Siamese cat is a big, big DNA pool around the world, for example. But anyways, it was so interesting for me to realize you don't know everything—shut up and listen and take a few flyers, 'cause you don't know, and you're going to be richly rewarded for it.

How do those terms work on the show, like in terms of like the fine print of the deals? Like besides just the investment, you know what I mean?

Well, we got the guy right here—Matt, some of my analysts is here.

So does it go into like a long-form negotiation after the...?

Yeah, yeah, yeah, you get to do due diligence. People say things in front of the cameras and the lights in the moment. I don't blame them for trying to pitch themselves in the best light they can; they've been practicing for months in front of a mirror.

But nothing is the same as when you walk out there, and the 26 cameras are rolling, and the sharks are up there, and there's a billion dollars in front of you, and this is your moment—this is it!

I've seen crazy [ __ ] happen, like people pass out—they go nuts when they don't get a deal—all kinds of stuff! But it's very unusual; I've seen it all. I mean, I've seen thousands of pitches over 16 years.

But I will tell you, the three M— I should disclose this to you; there are three things present in every successful pitch. Doesn’t M—they don’t know each other! It's different deals; they've never met each other, they don't know this. But if you look at 16 years of pitches on the ones that actually got funded, they all have three attributes: the same three attributes.

Number one: they were able to articulate the opportunity in 90 seconds or less. They were able to explain the idea in sometimes 20 seconds. They understood that it was important to just light the room up with an idea. And if you can't explain it in 90 seconds or less, you're lost—you're lost! But most of them did it in 30 seconds; that's number one! Everybody wakes up and says, "Ooh, interesting idea! Interesting idea! I've never heard of that before."

But that's not enough! The next piece, which takes longer, is you have to explain why—why you can execute on this idea. What is it about you that knows how to take this and turn it into a business? Did you work for a competitor? Did you work to try it before and failed before?

I'd rather invest in an entrepreneur that failed than one that's just made it—you know, thinks they can get it right the first time! But something about you that ties you to the idea because, after all, great ideas are a dime a dozen; executional skills are really rare.

But there's the one third one, and this one is tough, because imagine you get the first two right. Everybody wants to invest in you; they're all pitching—they all want to be part of the deal. They love it! You got to know your numbers—how big is the market? How fast is it growing? What's the break-even analysis? What is it about this, you know, market that you understand right down to every cent?

You know the business model? How many competitors are there? How fast is it growing? If you get those three right, you'll find that three attributes in every successful pitch, and it goes beyond Shark Tank. That's the essence of leadership right there! Right there! Those three things are present. Whether you're a general, a parent, a preacher, an entrepreneur, a manager in some business— that's leadership right there!

That's it! And I teach that now because I've seen it so many times; that's it! That's the essence of success distilled into three things that you should never forget.

It seems like, too, you're pretty needed on the show 'cause you're the only, like, savage person who will hit them straight with it.

Yeah. And do you ever feel like that's a problem for the other host, like Robert, who's maybe softer on the people?

You know, you've brought up a good point here—um, it's a delicate one, because, you know, I just—I was living this 12 hours ago, right, on the Shark Tank. Literally, we’re shooting late, so think about—ask yourself this: Is it better to tell them the truth, or is it better to take care of their feelings when you know with certainty their idea is complete dog [ __ ]? It's going to zero!

Imagine they're mortgaging their home; they're borrowing money from friends and family. It's a complete turd; it's going to zero! Now, Lori's on my left, Barbara's on my right, and they're so "Kumbaya," and they say, "Well, you know, I just think you're wonderful, and I admire you coming here and, you know, pitching this idea. I can't invest because it's just not for me."

When I know with certainty they wouldn't touch this radioactive turd at any price; it's just a dog! And I listen to all this, and I just finally say to them, "Listen, your idea is a piece of [ __ ]. It's going to zero! You're wasting your time. The only person up here telling you the truth is me. They're sucking you because they don't want to hurt your feelings. I don't give a [ __ ] about your feelings; I care about your money! And I think you're wasting your parents' money, your money, and you're wasting the most precious assets you have in your life: time. Take this idea behind the barn and shoot it and come back with something better."

And then they start crying, and then everybody's saying what a mean guy I am. [ __ ]! I'm the only guy that's kind to them. That's my answer to that question.

And by the way, the only reason Barbara gets here every year on time is I buy her a new broom.

A new what?

Broom!

Broom?

Yeah, she flies here!

Oh my god, dude!

Yeah, listen, I'm a nice guy! I bought—I bought her the new—this 3000! But except for the cat lady who proved you wrong, right?

She got you!

Hey, I invested in her!

Yeah, 'cause you want to get her the out of there, 'cause the idea was so bad, right?

Till it made you the most money!

You know, I began to realize anyone with that much tenacity, anybody with that much—she—she was—she had balls! She just wouldn't stop, and I thought if she’s doing this to me, what is she going to do when she gets out there in the real world? She's a killer!

Yeah, she was a beast. You're betting on the horse there and the jockey in a deal like that.

You got a great idea, it turns out. But she was just unbelievable—Ana Skaya. And by the way, over 16 years, 70% of my returns have come from companies run by women in the venture space.

I a lot about...

Yeah, yeah, yeah! The Shark Tank deals—70% women—that's where I made my money. Now look, I invest in real estate and a lot of other stuff, but in venture investing, women are killers because they really understand risk mitigation.

You know this idea: if you want something done, give it to a busy mother? That's true! They balance a lot of stuff in their lives, so if they say, "I got three kids," I don't care! I know that they can be really good entrepreneurs and they can run a business because I've seen it happen multiple times for me—multiple times, multiple times.

What about on the flip side, where you were super confident in a business that you invested in and it completely flopped?

Yeah, that happens. You know, is there any particular that really bothered you or you were surprised?

Well, let me tell you this story; I think I find it interesting. When I was, um, you know, my dad died when he was very young, and my stepfather really encouraged me. He said, "Listen, you're listless; you want to be a guitarist, and then you want to be a photographer, and you're going to starve to death—like, you just don't know what you want to do! Why don't you go to school and take some business degrees?"

And I ended up doing an MBA. I didn't know what I wanted to do, and in the last week of the—you know, they bring in these guest lecturer guys into the class, and this particular guy came in. You know, in the classic, you got 160 guys in this amphitheater deal, and the professor is down at the bottom—you got your nameplate there, and you've been with these people two years going through your masters of business, and this guy comes in a week before we're graduating.

He doesn't say anything; he walks in, he's just walking up and down the aisles and looking up at everybody for like—it felt like forever. It was probably only 90 seconds. And then he said, "You guys think you're such hot [ __ ]? You have your MBA; you're about to graduate. You're just going to tear the world apart, you're so full of [ __ ]. A third of you are going to fail within two years. Another third are going to become consultants, and the rest of you are going to work like hell to try and get a business off the ground. And half of you will fail! You don't know anything! You have no experience!"

And I—Barry Nicole is a guy beside me; he's dead now—a great classmate, but God rest his soul. But I leaned over to Barry and said, "This guy is such an [ __ ]!"

You know who that guy is today? Me! That's how I feel 'cause I teach now in those classes; they say the same thing.

So my point about this is, as you age and you experience stuff, that you can never do—there's no way to get experience free; you can't do it. You have to go experience it—lose money, invest in bad stuff, learn what works—learn about people. A lot of people are bullshitters, by the way—particularly in this town. This is the king of [ __ ] Los Angeles, just so you guys know, in case you didn't know that!

There's nothing more bullshitty than the media industry and the movie industry. I've never seen such [ __ ] in my life. But I love it, just to let you know!

But you have to understand who you're dealing with, and you only get that through experience. You start to get that in your DNA. And so the mistake I've made in investments—I don't do this anymore, but long answer to that question is I don't listen to my gut.

I'm writing a check to a guy for half a million bucks, and my gut is saying, "Don't do this! This is a loser!" And I've done it a few times, and I've ignored my inner instinct, which is actually another word for experience.

So you should, you've got to respect that in you over time. And the older you get, the better you're getting at this. But if you don't listen to your experience, you're going to lose a lot of money and a lot of time, and now I don't do that.

I don't give a [ __ ] if my gut says no; I don't do it. I don't care what the [ __ ]—you know what anybody tells me or what they say, or I just say, "You know what? I'm not doing it," 'cause it just doesn't feel right!

I don't give a [ __ ] what you say! And I get—you know, I look at deals every day; I see deals every single day, and I just—I wait for the feeling to hit me, and it's not right some of the time; it's right 100% of the time because I go back two years later and say, "What happened to that deal?"

It's a zero, but my instinct told me, "Don't do it."

What's been the most emotional someone's got when you've said something like savage to them on the show?

It's been pretty bad; it's been pretty bad.

You've been attacked before or charged; they've charged your chair?

We have a psychiatrist there, really!

Y?

We need one! We need one! We've had some very, very difficult moments, and I think that's what makes the show work—it's real; it's brutal; it's hard; it's tough. Most people don't get deals; they don't like that answer, but they get that.

And you know, it's a very, very hard moment, and I've got to respect, got to give them a moment, got to give them time. But I must say, when it comes to business, crying does not help. It just doesn't work!

I feel bad for you; I feel sorry!

On the show a few times, though, I mean let me—let's just stay on the topic for a second! You think you can cry your way into an investment? You think you can sit there weeping, saying, "Please give me money"? You think that works?

I've seen some stuff like that on the show, though, where it seems like maybe they chop it up that way, but it has worked.

Not with you!

Look, there are emotional moments, but if it's not a good business, it doesn't matter how much you cry! There are emotional moments, particularly when people have lost parents, and there— you know, [ __ ] happens.

You know, when you're in that moment, and you get in the zone, and you're pitching, and you're just there, you can—nobody sees the cameras anymore. It's just what it is. And [ __ ] happens; it just happens, and I—I appreciate the human experience.

But if everybody said no to you and you start crying, I hate to tell you this: I don't give a [ __ ]. I just don't care because you have to be able to suck it up, pick yourself up, and go do something else better; then I'll respect you for it. But don't sit there crying!

I mean, I don't care, and believe me, I'm going to sleep at night, no problem!

I've seen it all.

You said Barbara was a witch; who do you think is most impressive out of your other hosts?

You know, I—I—there's the thing—it's very difficult because everybody there is self-made. They're not posers; they made their own money, and so they've done it themselves, and so you've got to respect that.

You may not agree with them on one particular deal or another. I have a lot of respect for Barbara, actually. She's a great chef, and so am I! And we cook for each other in New York when I'm there!

And I've known her forever. Cuban—an incredible guy—we don't agree on anything, but I mean, I've known the guy forever, and we do a lot of stuff—we do deals together, and he's helped me in a lot of other stuff.

And Dame is like a brother in Miami. We hang out, you know, it's— it's a family, but it's not just them. Think about the 15 people that work on that show that have been around that thing for 16 years; it's a family.

And then we just won the Emmy last night or two nights ago—that was cool! You know, you're sitting in the audience—I—you know, I've always thought, "What's it like when they call your name?" That's pretty damn cool!

That's dope! That was very cool! We walked out of there with those Emmys! I loved it! I loved it!

What's been the secret to like keeping all you guys together? CU you guys are all strong personalities and obviously financially successful.

What's been the secret for that long? There must have been some arguments and personality clashes.

Yeah, there have been! There have been! But we leave it in—leave it in the studio! When we break at night, we've had horrific arguments! I remember once when Robert walked off the set; he was so pissed, and he was pissed—pissed! Like real pissed!

And we didn't even stop tape; we just kept rolling! And when we broke that night, we all went for dinner! We didn't even talk about it; it just was the way it was.

And I think we were able to distance ourselves from the emotion of that.

Um, but you know, you think about the alchemy of putting those people together—the genius of that! How did that happen? How did they pick the right personalities back then, 16 years ago?

I remember meeting here at Shutters with Mark Burnett 16 years ago, and he said, "Look, I got this new show called Shark Tank, based off a Japanese format called Dragon's Den, and I want to bring it to America. I'm going to change the name; it's going to be called Shark Tank, and I'm looking for a real [ __ ], and you're it."

I said, "Wow, no kidding! That sounds good!"

And that was the beginning.

How do you think you had that sort of, uh, look for you? Like, how did he know you were an [ __ ]?

Prior I was working in London on a show called Project Earth Discovery Channel. I'd worked on the Dragon's Den format as well, which was the original format.

He saw those tapes, got it, and he said, "Don't go changing; just be who you are, and let's just see how that works."

And I said, "You got it! I can't wait to work with you!" But it was also Sony, ABC, MGM—all the work they did in finding these personalities and putting us together.

We didn't even know each other!

And that—that—that day that we taped the first day, you could feel the sparks! It was just—I mean, that's the genius of Mark Burnett and that whole crew! They just—that's what they do! That's the creation of reality TV!

And that's why we're celebrating; it goes right back to this watch we were talking about—this watch; there's 23 of them in the world, and that was for the magic of those 23 people that day—almost to the day today, 16 years ago.

And we had no idea what would happen. I mean, now Shark Tank—it's insane; it's like a passport! I can go to any country in the world; it's on in 54 countries!

I show up in Norway or Switzerland or Abu Dhabi or France—there's Shark Tank fanfare everywhere! France—the Olympic? It's crazy!

Like, just was on a train between Zurich and, uh, Geneva—this couple came up to me and said, "We take a picture with you; we're from Austria; we just got married! You're the most hated man in Austria!"

I said, "Wow! You got to be kidding!" He said, "Yeah! Everybody hates you; you're so mean!" I said, "What do you want your picture with me for?"

"Well, we love Shark Tank!"

I said, "Okay, let's take the shot!" It was amazing, and that—that's the initiation of that brand! It's just incredible!

You don't care about being the hated guy at all, huh?

That, that guy, when you were young, gave you the, "Okay, F you!"

You know, listen, that, that is the real me, and I can't change, and I—I can't fake it. And you know, I—you know, I don't—you know, I don't—I actually don't care!

Yeah, I don't care! I care what my family and friends think about me, but I don't—how can I take care of, you know, 100 million people? That's what 100 million people watch Shark Tank in syndication in America every year! A lot of them don't like me!

What am I supposed to do about that? I'm supposed to stay up at night worrying about it? I—I—I can't make everybody happy; I don't even try—it's pointless!

I like—I don't care if you like me; I just want you to respect me, and I don't lie to anybody! I—you know, I just tell the truth, and if you can't deal with it, I don't care!

You know, it's just—what am I—how can I possibly help you? I mean, you know, just if you don't listen to the truth, I can't help you!

I'm giving you good advice; you don't want it? Don't use it; I don't care!

What made you decide to run for Prime Minister?

I don't know what the [ __ ] I was thinking! You know, I—I just—that was an unbelievable experience! I just—I don't know what the hell I was thinking! I remember I went home and told my wife; she said, "What are you crazy? Are you out of your mind? Why would you want to do that to us?"

And I said, "I'm going to do it!"

And oh, wow—that was—that was so crazy; that was so crazy!

And I'll tell you what it distills down to: in celebrity, we're just talking about this. In celebrities, some people don't like you; I get it, they don't like you, they don't like you who you are, they don't like—they don't like you in politics!

50% of the population hate you, and some of them want to kill you. That's the difference! And you don't know it until you're in it.

And then you realize, "Whoa! Whoa! This is crazy! This is crazy, crazy, crazy stuff!" You got people that are threatening your life that are serious and might want to kill you. Like, that's nuts!

So when you know people talk to me about AOC or Elizabeth Warren or any politician or Trump or Harris, I have a lot of respect for them because I know what that's like—it's brutal! It's brutal; it's unbelievably brutal!

Brutal! I mean, somebody just took a pot shot at Trump; that was just weeks ago. Imagine how that sobers you up! Take a bullet in your head; like, that is just life-changing, for sure!

And I—I think anyways, I did it, and I experienced something I'd never done before; that was the comfort zone thing I was talking about—not doing that again. That was just unbelievable!

But it did open my eyes up to politics, and, um, anybody that's thinking about doing that should really do some soul searching about, "Is this what I want to do? Is this how I want to spend my hours of the day?"

'Cause 50% of the people, no matter who you are, hate you—they just hate you, and that's the nature of our democracy: good, bad, and ugly; that’s just the way it is.

You've never spoken to Trudeau, have you?

No, I don't like that guy! Not because he's a bad person; he's just a horrible manager! He's the worst Prime Minister the country's ever had!

And I spend a lot of my time explaining why he's so bad because there's an election coming up; it could happen any week, actually. He's down to almost a non—he's one non-confidence vote away!

Parliamentary system from Britain—you need to have a coalition that keeps you in power; your cabinet keeps you in power. When people start to lose confidence in you, you start making alliances with your competitors.

In his case, the NDP, which is a socialist party. But now they don't like him either, and so he's very, very in a very precarious position, but he's had a great run over nine years.

Brought the country to its knees—unbelievably bad management. The way you should do it as a— in the parliamentary system is you're the Prime Minister; you don't have to run anything.

What you have to do is hire good managers for the seats of finance, military procurement, environment—these different cabinet positions. You hire them, and you put these people in place, and they work for you.

Now, if you don't have any skill at that, you're screwed. For example, he put a journalist in for finance minister with no skills whatsoever in finance—never ran a bank! I mean, why would you do that?

And of course, she's a total failure! It's unfair to put her in that position; she decimated the company! Capital's leaving Canada like crazy! When she started, it was coming into the country; now it's leaving! I mean, like, it's sad—it's just sad!

It's so unfair to her to do that to her, put her— I mean, imagine when she goes to a G7 meeting or G20 meeting; they must—I mean, everybody in there is from the banking sector—global banking—and she's a journalist!

I mean, they must look at her and say, "Why are you here? Do you want an interview with me?" I mean, I just can't imagine what that's like!

Anyways, we got to get rid of him; I want to—I can't say enough bad stuff. I spend a lot of time saying it; I go up there and I point it out to people.

Um, but remember, you got to respect the success he's had; he's one of the most successful Prime Ministers in history staying in power that long with absolutely no executional skills—is remarkable!

It's just remarkable!

What's he going to do afterwards?

Well, he won't be running any of my businesses, I'll tell you that! I mean, my goodness! You wouldn't put that guy in a candy store; it’d go bankrupt in the first 48 hours!

Yeah, he's the most hated Prime Minister; I'm from Mississauga, so yeah, few of us are Canadian. You know what I'm talking about!

You go to Alberta, and he's just like, "No!"

I do go to Alberta; I do go to Alberta!

It's crazy! Yeah, it's—they want to leave! Alberta wants to leave Canada; they can't take it anymore! They have all the wealth there, and they're paying for all of his mistakes.

I did—you know, I went to—I was going to go to a wedding in Egypt recently—very famous entrepreneur Anaran had a wedding. It's famous! Like this, he took over the Sphinx and the pyramids.

And I was getting—I was going to go fly there, and I showed my Canadian passport; they said, "Oh no, no, no, no Canadians, you need a visa!"

I said, "What? I'm a Canadian; everybody loves us!"

He said, "No, no, they don't! Um, we don't love you; your guy came down down here and pissed off every Egyptian!"

I didn't even know he did that!

What did he do?

I have no idea, but they wouldn't let me in the country! Same with—he pissed off the Indians!

This guy took a Golden Passport and turned it into [ __ ]. You possibly do that? He shouldn't ever go anywhere!

Don't say anything, don't go anywhere—stay in a closet and be quiet for now because you're killing the country!

I had no idea that had happened! I had to use my Irish passport to get into—I'm very fortunate; I have an Irish, I have a Canadian, and I have an Emirati residency card.

I want to become an Emirati citizen; I love that country, and I tell you that guy is bad news! And I'm just telling the truth here—it's very important that he move on. Very, very important!

Richest country on Earth per capita in terms of resources, run by idiots!

That's the sad—that’s what Canada is, and it's got to change.

What do you think about, uh, Cuban supporting Kala?

Let me talk about what's going on here that I've never seen before because I'm a policy junkie. I don't care who's in the White House; I care what the policy is.

I have never seen a race for the White House where a candidate has never talked to the press. That's unprecedented—she's actually doing this without giving any detail to her policy, and she has a 50/50 chance of winning with absolutely no one knowing what she's going to do!

I've never seen it! I've watched every presidential election in history! Because I have to know what the policy is as an investor; I don't know what if she's really going to do capital gains on, you know, tax on unrealized capital gains—that would decimate America.

That would be it! It would crush it! There'd be no capital formation here anymore! That can't be real! She could never do that, would she?

I mean, but nobody can ask her, 'cause she won't take an interview! I mean, her—what she did on the—in the debate was say, "Look, I'm not Trump; we should all hate Trump! Let's hate him and Kumbaya!" And that worked for her!

I think she did a pretty good job with the hate Trump thing last night or whatever the debate was!

Um, I don't know what's going to happen, but I also look at the polls, and this thing is a jump ball. This election will be decided by less than 200,000 votes, and I have no idea who's going to win.

But I really, really wish she would come out and talk to the press—pick any press, take an interview! But she doesn't!

What's your gut telling you?

My gut is telling me—'cause I actually, last night, um, watched the whole thing, and then, because we're out in LA, I was able to sit down and go through all the blog spheres, all the data being generated out of Europe—all of the snap polls. Some of it was done by CNN—nothing's changed!

It's in the seven states; you were not done yet! You got to move the needle! You got to move the needle on the seven states of those.

There's a very famous interview in Pennsylvania from last night that's all over the internet today of a woman just saying, "Look, I didn't get any information last night! I didn't get any from him; I didn't get any from her! I don't know what I'm doing yet!"

That's kind of where we're at! So we need another debate where the journalists are asking policy questions on important issues like border, like tax, like energy policy, like health care—specific answers so you can hear what their plans are and then make a decision based on policy!

'Cause that's actually how—what wins elections! Everybody thinks it's Kumbaya! It's not! If you're sitting there and you can't afford to feed your family, you're pretty pissed off with inflation! You want to hear some answers—what's going to change?

And price gouging policy doesn't work! They tried that in Venezuela; you can't do that! That—and I—I would want to ask her, "Is that the plan? Like are you going to do Venezuela-type price controls?"

That's not going to work in America!

What about this giving people $25,000 to buy a house? That's crazy! You'll just inflate the house by $25,000! It's hard to get a house now; it'll just be $225,000 more expensive! That's nuts!

So these are questions that I think we got to get answers to as opposed to just saying, "Yeah, don't worry about it. Be happy!" 'Cause that's kind of what it was like last night!

So I don't know—my gut doesn't—no, no!

Anybody says they know what's going to happen, this election is full of [ __ ]!

After watching last night, is there anything you would say Trump needs to do differently?

Yeah! He didn't attach her till the end! She owns the border; she owns inflation; she owns so many issues 'cause she's been the incumbent! And he didn't attach her to that!

That's his fault, and she stepped all over him by baiting him with the— you know, Trump goes nuts when you tell him his audience isn't big in a rally! I don't know why! He gives a [ __ ]!

But he is who he is; everybody knows who he is; they don't know who she is yet! They got a taste of it last night, whether they liked it or didn't, I don't know! But he's got to do a little more back saying, "Look, you are the reason we have inflation!"

He didn't do that, 'cause she signed that bill—the Inflation Reduction Act was very inflationary! I was thinking, "Why doesn't he just say, like, 'What's going on right now is you're in the—this is your administration?'"

Yeah.

Yeah, saying you're going to handle these problems, but we're living this issue with you in office.

He said that a few times, though! He said, "If you want to change something, why don't you just do it right now? Why don't you do it for years?"

Yeah, exactly.

But he really brought that out at the end! His last statement should have been a constant theme!

I mean, everybody's criticizing his debate, but they don't know the outcome of it yet! Everybody's giving him a hard time! I think he should do another one and be more disciplined!

I would like to see it, and I have to prepare myself for her candidacy and her eventual presidency if she becomes a president!

'Cause I still, on the 6th of November, I'm still going to have to invest! It's not going to make a difference to me if she's in the White House or not, you know! It's just I’d like to know the policy so I can prepare for what that's going to look like, I mean, if I really thought there was going to be a tax on capital gains, I would change my investment strategy, definitely!

But I don't know that yet, 'cause I don't have any answers from her! There's no way that that could be possible, right?

Well, that's what scares me! I mean, you know, did she actually say that?

She did!

She did say that! So she talked about a 28% tax rate; that would make us the most uncompetitive in the G7! That would just be crazy!

We'd be money leaving here like crazy because you add State on top of that, you're talking over 30% corporate tax; that's nuts!

Because that—you can set a corporation up in Ireland, which is what they did last time! The tax was that high!

So that's a bad idea! There's a lot of bad ideas there! That's why I'm hoping if she becomes president, she just is just fooling on all this stuff, and she gets some good advisors!

I mean, basically, she'll say they're both saying anything to get elected, and then they'll have to deal with policy later!

That's what it sounds like to me!

It seems like that she was so trained last night, right? And I feel like Trump—do you think he could use a little coaching? Like on— like, "Hey, you need to keep your cool," or "You can't personally attack her," or "You got to answer things a different way?"

No, the media—I don't think they can change him!

Do you think that's going to hurt his cause?

It's really now about policy—it’s if you could understand what the manual of policy is, which one would you vote for? 'Cause they're not going to change Trump in 58 days.

Um, I don't know anything about her, 'cause she won't talk to anybody! She may be a very nice person, I've never met her! I don't know—I know her ideas are not good for capitalism; I know that, and that's pretty scary!

'Cause this country is built on the backbone of capitalism! It's the number one economy in the world by miles! It's where 50% of all capital is invested from around the world! Every investor from everywhere wants to invest here!

And the number one export of America is not a product or service; the number one export is the American dream! And you never want to [ __ ] with that! Like, that would be—I don't care who you are as a politician! If you don't understand that, that is what this country exports!

There's a reason people try to cross barbed wire fences to get in here—it's the American dream! They're willing to risk their lives and drown in a river because it's the American dream!

It's not any one policy; it's the American dream!

And so that has to be the thing that everybody upholds and makes sure sustains itself as it has for over 200 years! So when I hear policies that are crazy, that in any way could affect the American dream, I think that that is the worst idea ever.

And so that's what's at risk with bad policy, and I think that's what every politician needs to think about in this election is who upholds the American dream because that's the thing that makes this country what it is—not one sector, not mining, not technology; that's all [ __ ]!

The American dream is the number one export, and it's the number one coveted thing that everybody on Earth wants!

I've never met anybody in my travels that said I don't want to go to America! I've never heard that! Ever!

Ever! Anywhere, ever! I've heard it from other—in other countries! I want to get out of this country and go to America!

And it's the American dream!

How important do you think the freedom of speech is to the American dream? Because you saw the bit where Cala was talking about, I guess, it sent to Elon Musk about the privilege of saying the things that he's able to say on such a big platform, and it should—sort of...

I know that narrative!

You know, here's a way to look at it from a pragmatic point of view. The cost of the American dream is freedom of speech—that's the price!

Which means there will always be the lunatic fringe, which is 2.5% of the population will say things you will find very distasteful! If the price is only 25% and the rest works, you pay that price every day!

You can't squash the 2.5% and give up freedom of speech because you give up the American dream! And so everything has a price, and that's what it is!

So if you're offended and, you know, everybody thinks, "Well, we've got to squash this voice, or that voice, or that voice," America has a way of fixing it all!

It just—it takes this rhetoric and this craziness and these nutbars and just somehow encapsulates them and passes them by! That's how it works! They don't last that long!

It's horrific while it's happening; it's horrible! I hate anything that has to do with, you know—I mean, the way I answer it is you just look at the organization—the people that work with me!

I don't care what gender you are, what sexual identity you have, what country you came from, who you worship—I couldn't care less as long as you can execute like you're working with me because you're a great leader, and you're a great entrepreneur, and you're a great person that's building a business!

So I don't need someone telling me I need diversification; I do it anyways because I hire great people, and I don't give a damn how you—what you are, who you are, how you dress—any of that stuff! I—I couldn't give a [ __ ]!

And that's actually what makes America work—more people like me acting that way, pursuing the American dream in the most efficient way we can and exporting that!

That's it! So, that's why it works! And so if that takes freedom of speech, fine!

Fine! I don't like hate speech; I think those people are [ __ ]! But it's the price of freedom—that's what it is!

Now that I hope people understand when I say that, 'cause that's what it is.

How the Happy Dads going down?

Good! Listen, I never had a happy dad, so hard tea! So, shameless promotion! I tell you why I like this—low sugar, but doesn’t taste like [ __ ]! It's got just enough to give you a good taste! I don't like carbonation; this doesn't have it!

SC tea is delicious; this is good [ __ ]! The Twisted Teas have like 26 grams of sugar a can, so those just have one! Le diabetes!

I’ve never tried one—it's my second!

Okay, this is good! This is good stuff! Appreciate it!

I mean, is this one of your sponsors?

No, we own it!

Okay, I want a royalty!

We'll talk!

All right! Kevin, thank you! Thank you, guys! Thank you!