How I Choose Opportunities That Align With My Brand | Behind The Velvet Rope PT 2

The social media following and the celebrity makes my deal making better because I could deliver the company's extraordinary reductions in customer acquisition costs. You can't run around all day long worrying what people think about you. I don't. You should not spend your day trying to make people like you; that is a waste of time.

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Who do you, I mean, I know the statistics and everything, but who do you feel like when you're sitting there? You come up against the most, like just in your mind, who are you always? It's down to like you and someone else. Like who do you lose deals? Do you feel the most out of your fellow sharks?

Well, I think that the most difficult shark to circumvent is Mr. Wonderful. He’s the guy I look out for, and I always want to do deals with him. He's my favorite shark; listen, he's a great shark.

What is the first... tell us one word that comes to mind when you think of like Robert, Damon, Lori, Mark, like each of them? When you work with somebody for this long, 13 years, that’s more than most people work with anybody. I mean, this is like, um, most people move jobs after three or four or five years, but we've been doing this together for a very long time. So, and we've built this incredible following and we know each other's banter.

But what makes it so interesting is each year it's never predictable. I mean, just something happens, something changes, something occurs. I don't, it just, you know. And we stay in touch during the year, but I will say this: everybody's lives are so busy because of Shark Tank that we've never been able to get them back in a room during the off-season, not even once. Never! You can't get them all together because we're just buried in stuff we're doing and we just can't get to the same city at the same time.

So, that moment when we all arrive, um, this year it'll be in July in Los Angeles, it's pretty... it's like you're... it's like a, uh, you know, summer camp reunion. And, you know, the thing is we work really hard; we get up at five in the morning and we don't get home till ten at night.

Um, and we just... the rest we... we shoot three days in a row and it's pretty tiring, and then we take a day off and we do shoot another three days in a row, and it's very intense and you need to stay sharp.

I remember in the early years, um, you know, the second season maybe we didn't really know each other, so we used to go out to dinner every night together. And one night, uh, Damon and I and Mark and Robert, I looked at my watch and it was 5:30 in the morning. We were in a club and I went, “Guys, are we shooting today?” And they looked at me and said, “Yeah!” We had stayed up all night.

And when I got to... so we realized we got to get to the set in 45 minutes; we had no sleep. And when I sat in the makeup chair, Darcy said to me, “You smell like a drunk,” and that day of Shark Tank was one of the best we ever taped. Everybody was so hungover that we just went at each other's throats for blood, and it was fantastic television.

You know, I'm not endorsing going out and drinking all night; I couldn't even do that today, but it was one of those moments that goes down in Shark Tank history. We'll never do that again.

I love it! What about the guest judges? Alex Rodriguez, have you ever met Jennifer Lopez?

Kevin: Yeah, yeah! She comes to the set. He's probably been on two or three times. She's there; I actually did a couple of awards shows with her. She's a very nice woman, there's no question about it. But, you know, the thing... everybody wants to come to the Shark Tank set; all the Hollywood stars either see themselves as a shark or, you know, they want to pitch an idea when we're taping.

Because of COVID, it's not the same today, but in the old days, every star in Hollywood was at the Shark Tank set. You know, John Mayer would come, and we had everybody. Everybody's... everybody wants to sit in the chairs and take that picture like this, you know? And it was just a rotating, you know, carousel of different artists, and we really enjoyed it because we'd have lunch with remarkable people.

Nothing breeds success like success. Well, maybe because she's already been to the set, Miss Jennifer Lopez could be a guest shark. I would think she'd be a terrific shark, you know? It's sort of... um, and the thing you have to know about the actual production process is there are laws that stop the producers from telling us anything about what's going to happen.

We don't know the deals; we don't know the guests. They are announced to us, you know, in a certain... with a certain protocol. And that's actually important for the show because the discovery of that deal, we do that with you. We're discovering at the same time you are when you're watching the show; we've never seen it before, and that's very, very important.

In fact, you're asked to disclose, have you ever talked to this to any of the sharks about this before? And if you have, you can't come on the show.

What about how was Bethenny Frankel as a guest judge?

Well, I know Bethenny quite well; actually, I've done deals with Bethenny. We have a deal called Snarky Tees together, which has done quite well. So, but, you know, everybody's their own crazy chicken, and she is definitely on the scale of crazy chicken. That doesn't shock me.

What about the fact, you know, she has this reputation of being like very difficult, like difficult to like work with? Like, is that true?

Nobody's difficult to work with; they're all competitors. Nobody's the same, and that's, I think, it's the unpredictability of what's going to happen that makes the show so interesting to watch. You have no idea what she's going to do. We've had plenty of guests that just are stunned by... you know, they think they're ready for it, and then they just get ripped to shreds.

And so, and it's really... I'm happy to do... I'm happy to deliver that news to them, no problem.

What about, you know, while we have David Spade now, who just replaced Chris Harrison, would you ever host a show like The Bachelorette or Bachelor?

I'm just, uh, I just wrapped a pilot for CNBC called Money Court here in Miami at the Telemundo Studios, NBC Universal. Uh, think of Judge Judy on steroids; it's real business cases. And so, in this case, I'm a judge, um, a real judge, a mediator.

Um, these are contracts signed with these disputes; these are litigants that come to the court. I have Katie Fang, a legendary, you know, reporter/ slash lawyer, a trial attorney, and Adam Pozzo, who's the Fed... was a federal judge. So, I've got real legal talent beside me.

We just finished taping it, which is why I'm in Miami. I'm doing some follow-up work for it; it'll air August 11th on CNBC. I think people are going to be stunned by what they see.

I mean, I was not prepared for what hit there, and then I got in the groove. It was really incredible. When people sue each other, um, real litigation within families, sometimes between landlords and tenants, business partners, it's really nasty.

I mean, there's the festering wounds within family members can be brutal. A mother suing her daughter, can you imagine that? It's all captured there on Money Court, and I think it's going to be very, very engaging. It's sad to watch it happen, but, um, but I think I did good work in helping these people find a resolution. Not everybody agreed with the outcomes, but it’s quite a show.

I get offered a lot of properties, a lot of shows. It has to be on brand for me; it has to kind of be... it has to feel natural. Like, being a judge and mediating business disputes is what I do every day in the real world anyway, so Money Court was a natural fit.

You know, I want to pick projects that I can grow; I want ownership in them, I want to invest in them. It's sort of the role of producer and talent at the same time at the end of the day. I'm an investor; I build businesses, I build companies, and it has to kind of fit into that.

And what we learned about Shark Tank is there's a tremendous interest in entrepreneurship. There's a lot of people that want to pursue that path, and so shows around that brand are interesting. But the granddaddy of all this is Shark Tank.

Uh, you know, that platform is... I'm not going to do something that competes with that. I mean, it's just too big a platform. One day I was thinking of, you know, um, [Music] branching out into something else, and I called up Lauren Michaels, who I— I don't know, I knew who he was, but the great thing about being a shark is everybody returns your calls; it's incredible.

And I asked him some advice about branding for television. He said, “You know you're the on Shark Tank, never ever give up.” I said, “That's very kind of you, thank you.”

Are there any guest judges? Like we mentioned Jennifer Lopez, like do you have like an ideal like, “Hey, I’d love to get this person on Shark Tank?” Or do a lot of people like a Jennifer Lopez type or whoever, like pitch you, like if you're out? You know, like you said, everyone wants to come on Shark Tank.

Oh yeah! I mean, Shark Tank is not having a hard time getting, uh, you know, products; they're just inundated with requests. I mean, when you get to that iconic level, you get thousands of... of... there’s a woman named Mindy casting who has cast every single deal since the very first one.

She has a whole team of people; it's like American Idol. I go to a city; they've got a thousand people lined up, and she sees every single pitch— can you imagine that? So she then recommends them to the producers. It's about 100 producers that actually develop these things and get to meet the entrepreneurs and do some background checking and all the rest of that.

People don't understand the amount of work that goes into making a show like Shark Tank. I mean, you got to hand it to those producers; that's why they won for... you know, what about like, does anything shock you in TV? Like, you know, like bringing up Bethany again, like she just had this huge, you know, seven-figure rumor deal with Mark Burnett, Big Shot.

She had, like, this MGM development deal, and now Big Shot, I don't think it went so well. No shade, you know? And now she's stepping away from it; the deal is over, whatever the reasons for that are. Who knows? Like, are you shocked when something is like so announced and it's going to be huge, like Bethenny and Mark Burnett? How could that fail?

I have been dealing with, uh, Hollywood for 15 years. Nothing shocks me, nothing! Nothing! I've seen everything. Um, it is a very flaky place. I remember once in season four, I won't mention his name, but anyways, there was a CEO of ABC, and I didn't want to have an agent because I’m perfectly capable of negotiating all my own deals.

I don't need help; I don't need lawyers. I don't need... I'll get them to pay for the deal after I’m finished, but I'll negotiate it myself. And so it was a... you know when it was a contract renewal for Shark Tank and what... and why would I want to pay somebody to do that for me?

So I went to tell them that at Sony and ABC and at Disney, and I said, “I don't need an agent.” They said, “Yeah, you do.” I said, “Why do I need an agent?” They said, “Because we do not want to deal directly with you; you're talent. You're nothing more than a piece of meat. And the sooner you realize that, the better. We'll trade you like a steak from one shop, one butcher to another. We don't care.”

Um, what's important is you have an agent that has something to barter on your behalf, and you don't have anything to barter except your piece of meat; you're the only steak in your house. We want a butcher with many steaks so that we can trade steaks. That's how brutal and blunt they were, and they were, of course, correct.

Because I wanted certain things they didn't want to give them to me, it would have been a really bloody blowout, you know, discussion. I would have maybe had hard feelings for those people that I need to have good relationships for. Instead, my agent – a good one that I basically met that, and decided to form a relationship with – did all that bloodshed for me and ended up with a much better deal that I could have never got.

I remember seeing that executive the next year, and I said... and he said to me, “Now what do you think?” He visited the set; we had a little conversation that line. She said, “Now what do you think? Was I right?” I said, “You were right.”

The town doesn't change; there's... it doesn't change at all. Nothing changes. The way it's working now is the same way it worked in the 40s and the 30s and the 20s before there was sound. It's a very closed, secret, strange club, and it ain't changing ever.

I'm always interested in meeting people that have a skill that, you know, I don't have or that they do something that really interests me. You know, that I share like watch collecting; I have a massive watch collection now. And so it... and I think of it as an asset, and there's a lot of people in Hollywood that pursue some of these eclectic things like guitars and all the rest of that.

But, but mostly, there's a downside to celebrity, and there's a positive side to it. The positive side is it opens a lot of doors. Uh, the downside is most people think they know you very well, and of course they don't. And that leads to uncomfortable moments sometimes.

But, you know, all in all, I'm very proud of what I've achieved in terms of television, how I've been able to combine... you know, for me, what this has done because I'm primarily an investor. The social media following and the celebrity makes my deal making better because I could deliver the company's extraordinary reductions in customer acquisition costs.

And that's how I've married the two. And so when people ask me about the downside of, you know, of celebrity, I tell them if the offset is this combination of investing with social media that's been incredibly successful for me. And, and I'm just, you know, I would have never guessed it; I didn't anticipate it. I wasn't planning for it, but I have a whole team of people that just do social now; we generate a ton of content.

You know, we're like a network; we have so many different channels and followings and strategies and social media and podcasts and YouTube and LinkedIn influencing all this stuff. It takes many people to do that work every day.

You once said, and like I said, when I had a company, I worked 24 hours a day, seven days a week, 365 days, and I'm pretty much there right now. I mean, you've made statements like this before. Is that the way of the entrepreneur or is there any other way? Like, you basically have seen... you say things like you just... that's what it takes; you have to sacrifice everything. Is that true?

You think there is no other way? Um, it's a global competition; your competitor is going to work 25 hours a day, eight days a week, and if you don't, they'll just kick your butt. Uh, it is a total commitment; it is so hard to do.

Uh, and the only way to know it is to do it, and it's... it's not instant riches; that's for sure. It's really... it's... most entrepreneurs work for years before they achieve success. It's tough, but if it's in your blood, then you pursue it, and the outcomes can be really good, and it lets you work harder at other stuff.

I mean, I just... I go back to what I said, you know, at the beginning of this conversation. It's... it's a lifestyle. It's... it's not a destination; it's a journey. And you have to be ready to... to go on that rocky road and all the good and bad and ugly that comes with it.

Um, add celebrity to it and it's even crazier, and so it's just... it is what it is and I live it every day, and I suck it up and I enjoy it. Not every day is a great day, but, you know, again, I control my destiny, and I want that.

I, you know, that's... that's what matters to me. These things matter to me, and it lets me, you know, get every drop out of life I can the way I want to.

You can't run around all day long worrying what people think about you. I don't. And so I learned that a long, long time ago. I think it's important to have, you know, an arm's length and understand that you should not spend your day trying to make people like you; that is a waste of time.

What do you think is like the biggest mistake that entrepreneurs made? Like, is there one thing you see that people just go wrong as an entrepreneur? They believe their own hype because they're out there spending a story about how great their business is going to be when everybody knows you have to pivot. Whatever you thought was going to happen never happens, so you have to be very flexible and try and figure out what you have to do to make it work. It's not easy.

What else does Mr. Wonderful do for fun? I know, you know, when you're building the business, you work 24/7, but you know, you're in a different situation now, even though time is still a problem. But I imagine you have some more time on your hands than in the beginning. Like, what do you do on your time off besides drink wine and travel?

Yeah, I mean, you know, I'm mostly starting new businesses these days. Recently I've become really interested in crypto, and I've started, um, decentralized finance business. I’m Buyer. I didn’t start it, but I renamed it Wonderfy; it was originally called DeFi Ventures. Now it's called Wonderfy. And somebody said to me, “What are you trying to copy Branson?” and I said, “Yeah, I am! I like his model and I like Wonderful, and I think it can help brand a lot of different things.”

And now it's Wonderful. So, you know, I think we'll be able to acquire a lot of customers that way and we'll see. You never know; it's got risk to it, but, um, I know Richard and I think what he did is brilliant, and I'm happy to copy something that works.

Why is it such a dirty thing for people to say, “I love money; I want to be filthy rich?” People don't want to just come out and say that. You have no problem saying that; why do you think people just can't say that?

Well, I say it in the context of freedom. You need money to be free, and so I don't say I love money; I love freedom. And along the way, you have to love money because that's how you get free. But you shouldn't pursue entrepreneurship for the greed of money; you should be pursuing it for the passion of freedom and to do the things that matter to you, you know?

And then at some point, support the charities you care about, support the educational initiatives you like, support the arts you like, become a collector of watches, whatever it is. But none of that happens without, you know, being in pursuit of money. Uh, in a business context, you have to make money; you have to be profitable. So it's not a dirty word to me, but the real outcome of money is freedom, and I equate the two together.

And I... being free is the essence of the American dream. Talk to us about shopmrwonderful.com. I know you mentioned that was coming. Is that just for wines or is there more that's going to be?

No, it's everything! I, you know, I tell people go visit my Instagram, Kevin O'Leary TV, on my Twitter, any of that stuff, you know, sign up for YouTube. Relationship, I'm... I'm... I'm always... I'm constantly putting out content about stuff I see every day, and I think some people enjoy it.

It's... it's an interesting way of communicating with millions of people; I couldn't put millions of people in a room, but somehow they are in a room on my social media platforms. It's really remarkable what's happened here.

So, you know, look me up on any platform and let's engage, and I invite everybody to do that. And if you like wine, uh, go to qbc.com and order a case; we'll ship it to you for free, and you will be just blown away by the quality of that wine. If you like that video, where do you see my next one? Don't forget to click right over here and subscribe.