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Daily Eccentric Habits of Kevin O’Leary


7m read
·Nov 7, 2024

[Music] Everybody asking all the time, how do you keep everything moving forward when you're traveling all over the place? This is a good example. I'm out in California here at the Sony lot, shooting season 11 of Shark Tank.

Now, this is pretty industrious because you get up at 5:00 in the morning. If you want to get a workout, you got to get up at 4:45, 5 o'clock, get an hour in, maybe come up, get ready. You're picked up at 6:30, 7 o'clock, go to the studio. But really what happens is your hotel room becomes your sort of center of operations. In order to make that work, I do a bunch of things I've learned over the years that really make it easy.

So first of all, you got to set up sort of a command control center. I use three different screens. I know it sounds crazy, but if you think about it, if you're doing, you know, a voice call or a video call with somebody, that's on one screen. You're reading a document, you're working on a deal, maybe that's the second screen, and then you're actually typing back and forth on a third. You know, laptops have become so light and small now you can get away with this.

I carry three different devices: a Surface Pro 2 - Microsoft Surface, an Apple iPad, and then two phones. Let me show you some other tricks I do. You know, at the end of the day when you're on the road and you're kind of dressing for Shark Tank, the only difference in my wardrobe are basically watches, cufflinks, and ties. That's about it, and one other thing: pens.

So here's what I do. I actually travel with a whole bunch of these things and I match them together. Have a look at this. Okay, here's the command center, three screens, a whole bunch of stuff here. I'm going to walk you through now because I wear the same suit all the time: black suit, black tie, crisp white shirt. There's not a whole lot I can mess around with, so I love pens, I love watches, and I love cufflinks. That's kind of what I got for jewelry.

So here's what I try to do every morning: I brought six different watches from my collections. I love to call it that, and I'm going to be wearing a different one every shoot day. So, you know, if you watch Shark Tank, you'll notice I'm wearing a different watch every single day. But they all have one thing in common: they all have a red band.

Now this little puppy here is a very new and rather controversial watch. This is the new AP Code 11:59, this perpetual calendar. I have it on a winder because I don't want it to run out. You know, when you're going to count when a professional calendar runs out, it's a total pain in the ass. You don't want that to happen, so I put this on for an hour in the morning. I'm just showing you how it's working here.

I've also brought a whole bunch of other watches. I've got a Daytona Panda on this wrist, red band. Here's another Hulk; this is the Green Hulk. Here we have an AP. This is beautiful; the Royal Oak. This is known as the Jumbo. Here we have the Pepsi and also the new Batman. Some people call it the Batgirl. I love all these watches; they all have red bands on them, and there's a reason for that. I'm known for red bands.

I like to have red bands. This AP integration was really complicated. Getting this AP Jumbo to a red band took a tremendous amount of work in cooperation with MRP Gaya themselves. Give me the special clasps and everything else, and then Rubber B had to do the modification. I don't own any of Rubber B. People keep asking why I'm endorsed for a long time. Why? Because it's a fantastic band, and the integration with the clasp and with the actual elements of the watch is almost perfect. When you look at it, it looks like it belongs on the watch, which is absolutely tremendous.

Now, with these red bands, I want to get a little acquainted. I'm going on here, so I'm using each day also different pens. This is the new James Dean from Moulins. But it's not just a pen; you want to think about which inks you're going to be writing with. They get all those close shots on Shark Tank. So I spoke to Moulins. They've luckily provided me with some really interesting eclectic inks.

Here's—let me show you this—this is a royal purple that was issued for the Beatles issue, and it's just fantastic. Beatles made special pens; here's one of them. It's also a gorgeous nib on this. This is a writing instrument that's just fantastic. It actually looks like a microphone top and a control knob in a recording studio with all the imagery of the Beatles.

But if you think about the Beatles' Sgt. Pepper's album, which is sort of the theme for this, that was a royal blue, and this is just spectacular. This ink is just gorgeous; it's a really rich royal blue ink. So I've been using that when I've been writing on the set for the last three days in some very interesting pens.

Lastly, you know when you're matching up on the links for this AP, this is a rose gold, so these gold Tiffany cufflinks are perfect with it. And of course, you want to have, when you're doing that, a gold tie pin to match. Then I use my classic for all the rest of the steel watches, the Daytonas and the steel IP. I just love these; these are a really interesting story.

One of the things you probably don't know about when you're shooting is everything has to be cleared by compliance. You have to go back to the company that made these and get them to agree that they're going to appear on Shark Tank. This took months and months and months. Every single one of these pens, all of these tie pins, all of these watches had to go through compliance and the red bands and everything else. It's just a crazy process of how I have to make television.

Show you something else. This is my belt that I've worn from the very first episode of Shark Tank, and you can see here it's marred; it's full of scrapes. This is where the microphone is attached to my belt and has been for ten years. I'm kind of superstitious on this; I want the same belt every time I shoot. Helps me get better deals, but all the sound people know it has the belt because you can see how this thing has been worn out.

You know, and living in a hotel room like this, you want to kind of think about other things too. I tell the staff, "Look, can you have some fresh fruit for me?" Because I get up so early and I come back so late. I don't want to have a meal; it's better just to crunch out an apple or maybe an orange or a banana or something, because you're getting home sometimes at ten, eleven, and you got to get up at 4:45 in the morning. That's the nature of making television.

A lot of people don't realize it's that much work; it takes a long time. It takes about an hour sometimes, an hour, to shoot one deal; maybe that's only seven minutes of television or maybe never air. You never know; that's the whole point. So I keep a bunch of other stuff around the room. I'm going to show you over here; you know I always keep a little red wine around, but most importantly, you got to have that fresh fruit. You know, that's the stuff you live off.

Always keep yourself hydrated, no question about that. And you know, I have some other wardrobe here I thought I'd show you. I'm doing a shoot while I'm here in L.A. for my chef, wonderful Shutdown Breann. So, you know, I try and keep this available; that's sort of my chef outfit. There's the wonderful logo. I'm doing pretty well with that: meat, cakes, chocolates.

Now, I love it because I go around the world looking for all these delicacies. So, the great thing about having a guitar around is, you know, you get a day off like today, you want to play every day and want to keep your chops up, keep your calluses crispy and your fingers. Guitar, guitar, still know what I'm talking about? But the idea is that, you know, what I like to do is write what I call little stingers, my own music, so I can put it into my own social media and my own videos and everything else.

It's just not having to deal with all those crazy music rights. Such a hassle: sync rights, publishing rights, all that stuff—a real headache. But when you write your own, the idea is you sit around, mess, you know, get a few riffs going, record them in the hotel room so you just remember what you did, and then go into the studio, clean it up, and lay it down.

So you just kind of [Music] [Applause] [Music] that's the idea. You know, try and find something you like, clean it up in the studio, lay it down in your video, save a ton of time on my music rights. Plus, it's just fun to mess around in a hotel room with the guitar. You got to have something to do.

Everywhere I go, sometimes I leave guitars in hotel rooms all over New York; I've got guitars and amplifiers. Just, you know, when I get back from the studio to do something anyway, I have a little insight on how this all works. You want to kind of keep yourself busy here on the road; it can be very boring and you want to stay out of the bar.

You don't want to be drinking; that's a lot of calories, and you got to have stuff to do. So command center, wardrobe, bring your watches on the road, your writing instruments, some great ink, a few guitars. Keep yourself busy. [Music] [Applause]

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