I Spent 1 Week with Billionaires - Robert Herjavec, Mark Cuban and Jay Leno

In this video, we'll explore what really happens behind the scenes of US Shark Tank, from the pictures to the off-camera moments. I'll do that deal. Then we'll dive into Jay Leno's legendary garage. I rest my case. And finally, we're off to explore Robert's insane house. Wow. So we're in sunny LA today and we're heading to the US Shark Tank. Lucky I've got a good lift and a very nice car to head there in style. Let's do it. So what's on the plans today? Filming. How long do you film for? We'll be here till 8. Yeah. Well, 12 hours. How many pictures do you get through? We'll do at least 10. Yeah. Very different to the Australian one. I'm so curious to see how you guys find it. What's your main tip for someone that's going to start a new cyber security startup? I met a guy the other day who's integrating AI and he's onboarded a fair few clients. But is there still room in the space, considering it's such a boring industry? The great thing about cyber is that it goes in cycles of about three years. And every three years, it eats its own young. And so there's constant room and improvement. And what's hot today will change in three years. You know why? Because hackers are moving at a pace faster than the industry. And being big means nothing in cyber. One of the most interesting things about the US Shark Tank is just the quality of entrepreneurs and businesses that come through. And they can get like a million dollars bump in sales just from going on the show. So it makes sense. But from like an ad perspective, a 30 second slot is like $300,000 or something like that on Shark Tank. So if you extrapolate that out for actually pitching, it's crazy. Crazy value. Honestly, that just there would be Shark Tank Australia. It's about 10 times bigger. It's huge. What do you think about AI and marketing technology? Do you think like the generative AI is going to be heaps revolutionary to a lot of your e-commerce businesses? Yeah. Do you think it's going to be separate winners or like specialized use cases? There's going to be two types of companies. Those who are great at AI and everybody else. Yeah. Even a small company. Now, I mean, kids are using chat GPT, Gemini, etc. to figure out whatever they want to figure out. So, you know, it's going to be natural. There was a day when computers were new, the internet was new, and then AI was new. But then everybody just got used to it. Yeah. Just another thing. And that's where AI is going. It'll be integrated into Shark Tank. And so you got to learn it. You got to use it. Do you think it'll be a bubble? No, no, no. In terms of investments, like what's happening is just like the early days of the internet, everybody's raising money to be able to buy as many chips as they possibly can to design the bigger and bigger and more complete bottlings. But the models are becoming more efficient. You won't need as many chips, hopefully, or as much power. And I think that will influence things so that smaller companies can do things. Yeah. So do you think it's going to be smaller companies that specialise, let's say copy, copywriting for e-commerce will be like one LLM that you use? Or do you reckon chat GPT will just own it all or Apple? I think there'll be some baseline models. Yeah. And then people will build on those. And we'll all have our own models. Yeah, that's fascinating. How old are you? 29. Okay. So you have a kid today, right? Do you have any kids? No, not yet. Okay. So if you had a kid next year, your kid, by the time your kid would turn six years old. Yeah. He'd have his own model that he can talk to and talks back to him. Yeah. And it would learn and then you'd be able to replay all the conversations with that with the model. Yeah. To see what your kid's up to. And then you can say, well, I want my kid to learn more about this, this, this, this. And it'll introduce that. So not only will every business have its own model, but every person will have their own. Yeah. Exciting space. I'll leave you to it. Love it. Were you always this happy? Yeah. You just seem like that first time I met you, or one of the first time you had us over at your house and we're like, where's Robert? I know the guests were sitting around and you were launching a toy rocket that you bought for one of your son on the beach. And I just see you like running fast. Did I buy it for my son? And if you've just been like this, even when you're a teenager or Yeah. Grind it, grinding it out in 12 hour days in the office, no money. I'm a pretty happy guy. 98% of the time. What, what makes you most unhappy? Like what event in what situations are you stuck talking to boring people or? I start to lose my shit when things aren't organized. I'm very detailed that way. When they're not organized? Yeah. You know, like when somebody messes up my reservation, you know, or we could have done something faster. Wasting time drives me absolutely batty. So that's the biggest thing about retiring is like, Kimmy will be like, Hey, let's go both pick up the kids. And I'd be like, well, sure. When we split this while I'm picking up the kids, you can be doing this. Yeah. And she's like, she looks at me. Don't we want to spend time together? And I'm like, oh yeah, yeah, yeah. That's right. But do you practice? Because I value time so precious. I have this overarching fear of running out of time and I want to squeeze every second out of life. Like everything. Why does Jay Leno hate Ferraris? When he was a struggling comedian was a maintenance guy. He's a mechanic. And I forget whether it was an Audi dealer or a Volkswagen dealer. He was actually, he worked there as a mechanic. And one day after work, when he was making a little bit of money, he's a very conservative guy. He still worked and was becoming a comedian. He went to a Ferrari dealership and they treated him like crap. They were like, oh, if you want that, you have to buy one of these. And he just thought they were so pretentious. And he never, never got into that. Never allowed them to rebuild the kind of situation. Ferrari doesn't need anything. Really? Yeah. There's an echelon in the pecking order. And I was at the very top. Like I was one of the top clients in the world. For Ferrari? For Ferrari. How many do you have? Oh, I had a lot at one point, but I had the rarest ones. Yeah. And then when I went through some difficulties, I had to sell one of my cars. That was like in the ethos of Ferrari. There's not a bigger no. No matter what situation? No. And so they kicked me out of the club. Wow. Hey man, how you doing? Long time no see. Welcome. This is my friend Davey from Australia. Davey, nice to meet you. Welcome. Everything here is part of the collection. Yeah, it's ready to go. This is awesome. Yeah. I think maybe you should roll around Beverly Hills in the electric Jolly, huh? What do you think? Is it starting most expensive down that end? Yeah. It goes from millions down to like 50 grand. Yeah. Oh, my knees don't fit in. This is not a kit car. This is an actual car. It's a, what was the original? Fiat Cinquecento? Yeah. Whatever they called it. They would stick them on the yachts and this was their kind of like island car. I love this car. What's this? So I've never seen this car. This is stunningly beautiful. Four year restoration, 1966 Jag XKE. Enzo Ferrari said it's the most beautiful car ever made and it's not even a Ferrari. I mean, it is just so beautiful. I feel like this is your favorite. I've never seen it. I think I'm just... You're just excited. Oh, my God. That is so sexy. I got to show you something on this car. It's incredible. So this is the Cullinan. It's enormous. It's so big. So nice to drive. I'm getting one. You are? You're going to get one? You should get one. I'm getting one of these. I love these. It's even bigger than the Spectre I'm sold. Uh, yeah. You know what? It's actually a great car to drive. It's like Jay said. What I love about these cars is they're unabashedly Rolls Royce. It makes no excuses for what it is. It's luxury. It's beauty. It's solid. It's not that loud, is it? No. Well, it's a luxury. It's luxury. Oh, okay. Okay. Well, yeah. Speaking of loud. Oh, wait till you hear this. So you won't know what this is because... Not your average SUV. In America, we have real cars, not like in Australia. So this is a Cadillac baby Escalade. Look how big this is. No, this is the boat. This is the boat. But it's not just a Cadillac Escalade. They made a special edition, the V version with a Corvette engine in it. In America, there's no such thing as too much power. So picking up the kids, you're running late, they're going to charge you extra for, you know, daycare. You got to go. You need to go fast. Jesus Christ. Isn't that sick? I did not expect that. And then, boom. This is what we've been waiting for. I bought this car a few years ago. I actually had to meet with Lamborghini to talk about the car and sign up for it. It's the 50th anniversary Lamborghini Countach. They only made 50 of them. It was 2.8, 2.9? I think it went right around there. How many other cars do you have that aren't just here? A few. This is so nice. I've never seen this. It's so beautiful. Start it up, Davey. Oh, it is quite deep, isn't it? Yeah, I know. It's got a good... I'm going to get out of the way in case he runs me over. So sexy. Wow. Very cool. Very happy with it. All right, well, I think this is the highest performance car here. Davey, let's take it for a spin. All right. Good to go. What do you think? It's nice. It's just jolting, isn't it? It's just... Well, because we're going too slow. Yeah. We're going 16 miles an hour. It doesn't know what gear to go in. Like his first gear will go like to probably 50 miles. Yeah. What was the first car you ever bought? Like your first ever good car? 1987 Mazda RX-7. In the ugliest gold color you can imagine. So nice. So Jay, I'm surrounded by so many beautiful cars. And I assume when you're a kid, correct me if I'm wrong, that this is your vision of success. Just being able to work on your cars every single day. Yeah, I think so. You know, I was always happy at whatever level I was in my life. So it wasn't like it was, oh, I have to have this. You know, I started doing comedy, just making enough money to eat and pay my rent. I was on top of the world. You know, I meet other people that get so obsessed. And I should be doing this. I should be the boss. And I should be the... No, I was just always happy at whatever level I was. And I think that's part of the key to success. Because people sense that when you're like, oh, this guy wants a little too much. You know what I mean? But if you're having fun and you enjoy yourself, then people want to help you do what, oh, I like this guy. I want to keep you happy. So you know what I mean? If that doesn't make any sense at all. Yeah, it does. Do you have advice for someone, like a young kid maybe, that's trying to find their polarity or their brand or their voice? You mean in show business? Yeah, just in show business. Well, what I would always tell people is, try and get up on stage. Don't try and be a comedian or whatever. Just like being MC in a talent show. Hey, my next guest is on. So if you say something funny, they get to laugh. Oh, okay, try another job. It doesn't go, okay. If you say you're a comedian, right away people are like, this. Make me laugh. Yeah, exactly. But if you present yourselves just a moment near the MC, then they're going, hey, that guy was as funny as the comics they had. He's not a comic. So I think to try to get as much stage time as you can. It's in church. It could be a synagogue. It could be a labor meeting. A friend of mine used to do a joke about it. He joined AA just to get the stage time. Hey, I've been an alcoholic. So it's, yeah. I'd love to learn a little bit more about the business of investing into cars. And I think you invest in watches as well, right? Yeah. How do you see investing in cars? Is it business? Is it passion? It costs just as much to restore a worthless car as it does a valuable car. So if you start with something valuable, it'll be worth more. You know, you get some worth because it's all labor. You know, most cars were built, especially older cars when technology was expensive and labor was cheap. Now it's the flip side. So you want to buy the best car you can. And then put whatever F you have to into it. What kind of, are you a Rolex guy? Like, rub it or? A Rolex is fine. I like some of the more obscure brands. You know, the one, there's some really good watches coming out of Germany. There's a little town called Glashütte in Germany where all watches are made. A Lange & Sohne are there. Glashütte Original are there. And these are brands that are challenging Patek Philippe and all the other big ones. So, and they've gone up in value. But here's the thing. If you're knowledgeable about your subject and you buy things about that subject, the fact that you like them means other knowledgeable people will like them too. So they'll probably go up in value. I mean, I always collect, like those Lamborghini Muros, I always thought they were great even when they were worthless because they were unique and they were, it was a new kind of design and, you know, would it catch on? We didn't really know, but I thought it would. And then of course I got the yellow ones for free and now it's worth two, $3 million. And I've heard you said that you're dyslexic. How does that disadvantage you? And what kind of advice would you have for entrepreneurs that are hanging on to those disadvantages and not letting them? Here was the cure for dyslexia when I was a kid. Smarten up, smarten up, smarten up. I'm smart, I'm smart. I got it now, I'm smart, I'm smart. So you're hard on yourself. Yeah, I think you have to be. Like I say, I'm always a believer, huge believer in low self-esteem. If you don't think you're the smartest person in the room, you shut up and you listen to people. You know, if you have a product that you invented, that means you're an inventor. You're not an entrepreneur. An entrepreneur is someone who knows how to sell your product. So find someone who can do what you can't do and put them to work, you know? It just seems like common sense to me. Yeah, you seem very frugal with money. I'm a Scotland, my mother's from Scotland. Have you tried to address that or do you think it makes you happy being like that? Because I, you know, I'm probably on the opposite side spending a little bit more money than- I rest my case. If you live within your means, you'll always be happy. You'll always be fine. You know, I always meet people like, why did they buy that? I mean, it doesn't make any sense, you know? So yeah, it probably comes from having a Scottish mother. My mother is from Scotland. When I got to Tonight Show, it was the Tonight Show starring Jay Leno. And my mother, oh, star in Jay Leno, Mr. Big Shot, star. I go, ma, that's what they do. Well, yeah, but star in. You got your name all over the show already. You got to have star in Jay Leno. And, you know, this went on for weeks, you know? And finally I called the producer and said, look, take that off. Make it the Tonight Show with Jay Leno. Just take starring off. And they were like, why? My mother's driving me crazy. So it came to the Tonight Show with my mother. Oh, that's much better. Now people are not going to think you're Mr. Who's Who. But, you know, it really is true. When people would say, oh, I don't know why I like you, but I like you. There's a number of reasons why. Maybe you're not pushing yourself in front of them all the time. Maybe you're not selling a product you don't really believe in. Or maybe you're just saying with Jay Leno instead of starring. Because what do I do if it's a star? I don't sing. I don't dance. So just make it with Jay Leno. Well, you're incredibly modest. So appreciate it. Well, thank you, mate. Thanks for having me. We've got a little bit of a gift for Robert. We've got a gift for you. You do? Yeah. What do you got? Showing us such a good time. So a lot of people ask me what you're like off camera. And you're genuinely one of the nicest people. Charlie can attest to that as well. You've shown us around LA. You're so very generous with your time. So we wanted to get you a gift. Oh, it's a bag. An empty bag. How nice of you. Oh, thank you. Hope you like it. Should I open it? I know you're a Rolex man. Do you unwrap gifts violently? Yeah, violently. Oh, yeah. Yeah. We know you're a Rolex man. But we wanted to start your Patek collection. No, you didn't. Oh my. So for context, Robert has about 75 and no Pateks. So we wanted to start an entry level Calatrava. Wow, you got me a Patek. We appreciate it. Holy shit. We appreciate everything that you do for Shark Tank. Oh, I should have been nicer. Entrepreneur. No, you've been very nice. Very nice. Oh my god. I don't know what to say, man. Very nice of you. Thank you. Appreciate it. It's so beautiful. Oh my god, that's amazing. Oh my god. I'm still like. We got him spageless. That was so nice of you, man. Even the people that we met this trip was a once in a lifetime trip. So super appreciative of it. This is a beautiful boat. What's this? This is a wire. Yeah, W-A-J-A-R. Stunning. Don't step on this, Davey, because you can fall in. One question I had is after I made a couple of bad business moves, one thing that I found is I started to get paralysis around decisions. Now your business is obviously enormous. And we're in the roles the other day. And you were talking about how the reason why you've become so big is because you made so many big bets, so many big moves in the space to keep hitting those sales trajectories. What's your kind of mentality around big bets? And how do you make sure that you don't lose it all? People overthink it. A big bet is the culmination of little successes or the avoidance of little failures. That's what everybody who doesn't have a business thinks. They think you stand on the edge of a cliff. You look down and you just jump off, right? Make a big bet. I always say, why not walk down the water, see how deep it is? So I tend to move quickly, fail fast or succeed fast, and then double it down. Yeah. Right? So if I'm investing $10,000 and it works, $20,000, $100,000, $1,000,000. Yeah. How do you do it? I think, yeah, generally what I'm trying to do at the moment is fractually test the concept by myself with high involvement and then put someone really good in the position. But I think it's when you're quite young, you haven't seen enough of the world, right? You haven't made a lot of these failures yet. So that's something that I realized when I first started. You know, I was hit after hit after hit. And I just couldn't fail. I had the framework. And then I was like, loss after loss after loss. And it was kind of like, what am I now doing wrong? And I think it was because, one, I was going into new and unexplored territories where there was just no previous learnings. But two, I just didn't have the right people to support me. Right. After proving it. So I think it's a much of a people issue rather than a concept issue. Oh, but that's for the execution of it after you've made the bet. Yeah. Here's another thing I've learned along the way, which was a big shock for me. When I was trying to make a big bet, I would go into a room with my team and make sure I had complete consensus. Hey, guys, we're going into this field. What do you all think? What I learned, though, is if you walk into a room and everybody else knows the answer and it's self-evident, it's probably too late. Yeah. To make a big bet, to really change course, it's usually something people haven't realized. You're trying to find there's margin in the non-consensus, right? There's margin in mystery. Yeah, it's good. One interesting contrast that I've seen is how many emails you do. How many emails do you do a day? Do you even know what email is? No, I just use Instagram DM. Seriously? No. Uh, 200, 250. That's an absurd amount of management, I guess. Is that just industry-specific or is that just your level of intensity that you've always operated at in terms of micromanaging? Yeah, everybody's different. I tend to go to the source. When I don't understand something, I don't want you to tell me about it. I want the guy or the girl actually doing the job telling me about it. Yeah. So I've always been a complete open door, but I want to know. I got to know for myself. So I send a lot of emails about what's going on. If there's an issue with a customer, I want to know from the engineer at the customer site. I don't want filtered information. I want raw data so I can compile it and make a decision on it. Across all of the departments? All the departments. Yeah, that makes sense. And I find that you outsource the responsibility of the things that you're least proficient in. And that's probably the thing that you should be focused mainly on. You got to start. You got to get good at everything, great at your skill set. When you get to a little bit of scale, then you hire an outsource, a CFO, a CRO, a CMO, whatever. One other really frame-breaking thing was you're the happiest person that I think I've ever met, but you love materialistic possessions. I do. And a lot of people, they chase materialistic possessions and that drives them into unhappiness. But you seem to be extremely content in the chaos, in the 200 emails a day. How do you see happiness and the relation to materialistic products? These are great questions. Thank you. I've done a million interviews. No one's ever asked me that. You know, here's a funny thing. You know me pretty well now. People that know me really well know I'm not driven by money at all, like at all, in the least. I love to play. I love this boat. I love the fact this boat was a million and a half dollars. I love the fact I had it built for me. I love jets. I love cars. I love watches. I love the watch you got me. I love to play at life, but I don't wake up in the morning. Oh, I need another Rolex. I need another jet. I'm driven by success. Like I just want to be the best I can be. I want to squeeze every second out of every moment in life and I kind of feel like stuff will come out of it. I love that. Does raw achievement give you confidence? Just stacking up undeniable proof? Doing it over and over and failing. Constant failure with a consistent goal gives you confidence. So I couldn't speak to people. I did a speech. Completely messed it up. I did it again. I was a little worse. I was a little better. But I just got to a point in my life where the pain of how I was living was greater than my need for mediocrity and was greater than my fear. That's it. Like, you know, we say to people, you're either going to accept your situation in life and bitch and complain for the rest of your life or you're just going to get over it and you're going to go do it. Like David Goggins always said, you don't want to run today? Go out and run. You're afraid of public speaking? Go out and public speak. You don't want to do it? Just do it. Well, it's been a great trip. Appreciate it. It's been a great trip, man. Thanks man. See you next time.