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How To Make A Living With NO "Job" | The Morning Toast Podcast


30m read
·Nov 7, 2024

[Music] Can you tell us you brought us a gift. You set up this entire little moment. What is going on here?

Well, today is a very special day in New York and I haven't been to New York for over a year because of the whole COVID thing. But today my wine company is going public on NASDAQ through a SPAC. In other words, it got acquired into a public company. Oh, and that's a very big day for us. We have been growing and growing and growing for seven years. We're now one of the largest wine companies in North America, and this is a, you know, big moment because we'll be making lots of announcements at 4 o'clock when I ring the closing bell.

Wow! Any sneak peeks for us?

Yeah, I'll tell you what, but let me just put on my very important elements when you're in the wine business.

Explain what this is.

This is when I'm in the cellar because I blend all the wines, or at least the O'Leary ones you're seeing. We go into the oak caskets and we take a little siphon called the thief and put a little bit into here, let it mix with the air, taste it, and then spit it out because if you do that for every bottle you're gonna get really wasted.

Yeah, so that's the whole idea. So the test of ambi has become the symbol of winemaking all around the world, and there are very famous organizations like the Chevalier de Tastevin I love when you say that on church I'm a member of. And those of us who blend wines now, these two wines I brought to celebrate with are my, these are my most award-winning wines and my biggest sellers: my Chardonnay. It's more of the Montreshe style, which is the French style of making Chardonnay, very crisp, very light, less oak. And then my incredible Cabernet Sauvignon, which has won award after award after award.

Wow, even Andy, our cameraman, when he got proposed to his fiancée, he took all the insurance necessary, which was two glasses of this.

Oh my gosh, and she immediately said yes, I'll marry you.

That's right, that's so, oh wow! And you know what? Like I feel like you've kind of made a mark for yourself in Shark Tank as the wine guy and when I met you, I feel like a lot of people don't know this but it's pretty common. You and your wife taught me that you can tell what kind of wine is in the bottle based on the shape of the bottle. Is that correct?

You can! You can! This is the classic French Cabernet and that's the classic Chardonnay. Now what's happened in America, you know, the most popular wines today are the Cabernet Sauvignon red and the Chardonnay. Chardonnay exploded when they started growing the grapes in California decades ago, and they started competing globally, and California Shards started kicking French Shards' butts a lot in international contests where it's blind taste testing. So the wine industry, the American wine industry, particularly in Washington State, Sonoma Valley, Napa Valley, it's really a big business now.

But there's an old joke about the wine business: if you want to become a millionaire in the wine business, start as a billionaire because everybody blows their brains out. They make it a labor of love. I'm in it to make money.

Yeah, and the only way you can make money in the wine business is have huge scale, be able to ship millions of cases, be able to fulfill Costco and Target my own wines. And the new trend, which we've really blown up big, is 46 states allow you to ship directly to your customer. Remember, a case of wine weighs 39 pounds.

Yeah, so if you get it direct, it's coming right to your door. And I have built that business up to being the largest direct consumer in the world, at least in North America. I can't say the globe yet because I don't know what they're doing in China, right? But I'll kick the Chinese butts too!

Yeah, in COVID, I mean direct to your home wine is every answer. Yeah, and what happened was people didn't stop drinking wine during COVID, but what really got crushed was our business to restaurants.

Yeah, that's when we replaced it with the direct consumer and blew that business up even bigger.

Yeah, and now people are saying I don't want to, you know, carry 12 bottles back from the store, just ship me another case, Mr. Wonderful.

Yeah, and I obliged!

So, I think one of my favorite interesting facts about you is now you're conquering wine. You've very much made yourself the wine connoisseur, but what you don't get enough credit for is you were also the original inventor of a childhood staple of ours: the Oregon Trail.

Yes, the Oregon Trail, Reader Rabbit, Where in the World's Carmen Sandiego, all those titles. Yes, and that's how I came up. That was my first business—was educational software.

Oh my gosh, I didn't know that!

Yeah, that was it! And we used to develop all kinds of titles. You know, Oregon Trail was an incredible product because it started in Minneapolis, I think Minnesota. I may have forgotten exactly which city, but I remember when we bought the title, we required it. I was blown away by how rich the storytelling was.

Yes, your ox died of sedentary! Like it was crazy!

Yeah, you know, people would try and get through the brutal lifestyle of moving west in, you know, in that time. But we invested a lot of money into it and made it one of the standards of 110,000 school buildings in America.

Yes, and I were among those schools, right? It's literally a cornerstone, like a staple of millennial early education. I have very fond memories of it.

Yeah, yeah! We sold that company for 4.2 billion dollars.

Very nice! And I started with nothing in the basement, you know, sort of a garage thing, and the 10 of us that were founders, that was our big liquidity event.

Yeah, and since then I've made many mistakes but also made a couple of good investments too, so it was a really big, it was a big moment for us because we really had nothing, and then boom!

And I remember the day we went back to the office and I said, everybody going to do? We can all retire!

And everybody said, I don't want to retire, just keep going!

So you entered the wine business as a billionaire.

Well, yes, but I've really learned a lot from the wine business. Most of the companies that I've made money with have been run by women that I've invested in, and the wine business included.

I remember when it started, it was actually a Shark Tank deal years and years ago called Zip Swine, single serve wine.

Oh, I remember! Of course!

Yeah, you guys went back and forth...

Yes! And it was one of the famous first times a guy ever came back twice.

Yes, and but I'll tell you the story of that. The day after that aired, I won the deal. I thought the place to get this into would be Costco.

Yeah!

Yeah, and there's a very famous story about Costco. This woman, Nate, and a woman named Annette Alvarez, who started in Costco in Florida, in Miami, sweeping floors.

She had such an incredible palate to taste wine that she quickly moved up the ranks to the regional buyer, and then she became the national buyer and then the head buyer for the whole of Costco.

And what you have to know is Costco is the largest wine buyer in the world, period. Nobody's bigger anywhere on Earth. So they get everything. She had 12 buyers underneath her, and it was also known that nobody could ever get to her.

Every wine company in the world wanted to talk to her, but she just wouldn't take calls. So after Shark Tank, I thought, I wonder if she's a Shark Tank fan, and I've got a guy on my staff that goes into the dark net, knows how to get cell numbers.

And so he got her cell number for me, and I called it and I left her a message saying, hey, it's Kevin O'Leary from Shark Tank. I have no idea if you watch the show at all, but I have this product called Zips. I'd like to show it to you.

Twenty minutes later, the phone rings. It's Annette Alvarez, and she says, you were rude to Barbara last night.

What? What does that have to do with anything?

She said, no, we're not doing any business until you apologize to Barbara.

Wow!

I said, what did I do wrong? She said, you were rude to her. You cut her off. She was speaking. I said, that happens every day on Shark Tank!

Yeah!

Plus, you want to have less out of Barbara, not more!

Anyways, we made it work, and she said, look, I'll give you one hour, John Wayne Airport this Saturday, and I want to meet your wife.

Oh wow!

I want to know who would marry a guy like you! Right?

I said, okay. And I said, Linda, we're going to John Wayne Airport. We're going to meet Annette Alvarez.

And here's where it all starts. We meet her, we sit down with her, she says, Kevin, let me tell you about the wine business you don't know. If you want to make money in the wine business and not be one of those schmoes that just starts a little winery and says, oh look, I got a winery, you have to be able to ship me 150,000 cases in a day!

Wow!

I said, and that I can't do that. She said, you can if you partner with Vintage Wine Estates, a guy named Pat Roney. You go cut a deal with him, you come back to me and watch what happens.

And she was the woman who gave me the advice that turned this whole thing and blew it up and now we're going public today.

Wow! Well congrats!

Yes, but I'm just telling you, listen to women sometimes, all the time! I'm just so... I shut up and listen a lot because that was great, great information.

That's so interesting. And you know because it's very, you know, you see you on Shark Tank, it's such a big show and I think a lot of people are under the misconception that that's not all you do.

You know, like you're a famous person now who made, you know, his billions on your educational company and now you just are a famous person who does Shark Tank, but you're still very much active in a lot of companies, correct?

Yeah, I have 35-plus portfolio companies across a wide range of activities. Everything in commercial kitchens, we do insecticides, we've got wireless charging companies, we make very famous gym equipment for condominiums here in New York that business exploded during COVID.

We have the wine business, obviously, and many, many, many others. I will tell you something, each day there's a catastrophe in some part of my business, you know, portfolio.

Some, something horrible is happening at the same time the phone rings and has some euphoric outcome that somebody's buying another one of our businesses.

Right?

And it's just like a passion play every day. You know, on one end total, on the other side fantastic things.

Yeah!

I've kind of gotten into the groove now, and I say, well, okay, that's just the way it's going to be. Yeah, you can't make everything work. And then every once in a while, boom! It hits big.

So how many, an estimate, how many companies do you think you've invested in from Shark Tank?

Oh, it's got to be probably over 100 by now. I've been doing this for 13 years.

And how many, an estimate, do you think you've made a pretty good return on?

Well, what happens is, let me give you the ratio because we've got all this data. In normal venture capital, when you go to Boston and talk to Silicon Valley to a venture capital firm, they do 10 deals and you look over eight years.

What happens? Two of them are absolutely wild successes. They make 40-50 times on their money.

And then about four of them are living dead. They're still in business, but they're just barely getting by, barely getting by, and unfortunately waste a lot of your time.

And the rest go to zero. And so it's sort of, you know, 20% work in the real world. In Shark Tank, 50% work, and here's why—here's the secret sauce.

So 50% of our deals make money because, see, how we're sitting here doing social media and you reach out and you've got millions of people listening to you, your customer acquisition costs are very low.

Yes, right! We get 100 million eyeballs a year on Shark Tank through syndication in 23 countries. So when we put a product on Shark Tank, it's not uncommon to get all your money back in 24 hours.

Yeah!

Oh wow!

Yeah, exactly! What happens! And so our customer acquisition costs are either zero or very low. So even a marginal company, a shitty company that can't acquire customers gets this jolt of, you know, free advertising for decades!

Yeah, yeah!

And boom, they just keep selling stuff, and we have all this stuff documented, the rise. So the whole thing about Shark Tank is getting on Shark Tank, and if you can get a deal, then you get the updates which are really powerful.

Some companies, I love the updates beyond the table, beyond the tank—we love.

But you know you get more sales on updates sometimes you get on the main show, huh? So you want to get a deal, that's the secret sauce to Shark Tank.

That's so interesting! What's your favorite category or type of product that comes into the tank when you're like, oh, I'm listening to this one?

I love companies, you know, right across the board, every category included that has already figured out social media and direct-to-consumer sales, and they know their customer acquisition cost when they walk on that set and say, look, we don't sell retail, we sell direct to consumer, and here's our customer acquisition jobs.

Here's the margins we make. All I'm doing then is pouring gasoline on the fire if they're asking for a million bucks. I'm happy to give it to them!

Yeah, because what's going to happen is we're going to just blow that business up because they've solved all the problems already.

Like the infrastructure's already there.

Exactly! And the ones that I... Those are the deals I tend to do. Anything run by a woman gets priority for me because I've made so much money with women.

I'm just, you know, I'm biased in some ways I shouldn't be, but it's fair. Women tend to mitigate risk. You know that old expression, you want something done, give it to a busy mother.

Yeah!

Like they can keep a lot of stuff in the air once and that's what you need in a small business. And also they're much more savvy on social media.

Yes!

And women are more likely to engage and share on social, so you want a woman speaking to them!

And well, the same way you do it, you know, you connect with these, you know, other people and they just want to hear what's next from you.

Right?

Well, companies that have figured that out have very, very powerful business models.

Yeah, and so what would you say is your most successful business investment from Shark Tank? Is it Plated even though that was... it's a New York City deal in some sense, right?

It was started here by a couple of entrepreneurs. They came on the show, they had a ridiculous valuation, they didn't get a deal.

A year later they run into me in the street and say, hey listen, we've been tenderized by the real world. We're willing to cut a deal!

And so we do it, we do a deal and then they get back into the tank in a follow-up and then one day we get a call from Albertsons right after Amazon bought Whole Foods and said we need to buy a digital platform for $340 million smackaroos.

Wow!

The business was like 36 months old!

So those dudes rode into the sunset!

That's amazing! We love so many of the episodes where you have guest sharks. We learned so much from them. Who was your dream guest shark for the tank? Have they already been on?

Well, no, no! My dream guest shark is Mr. Wonderful!

I love you!

I love that! I love that guy!

Yeah, we've had a lot of guest sharks. We've had all kinds of guest sharks. Some are better than others.

Some, you know, what happens with Shark Tank, and this includes all the people that come and pitch. They, you know, a hundred thousand people apply, 340 get picked, 220 get taped, maybe 180 air!

Wow!

Okay, so here's what happens. You've been practicing for months. You know you're going to get on that carpet.

Yeah!

And then you walk out the door, the museum practiced. Now it's real!

Yeah!

26 cameras rolling, jibs moving down, you know, steadicam all around you, and you freeze!

Yeah!

Yeah, sometimes it's painful.

I have to say, like at least for me, I can think of one episode in particular that will for me ever go down as the worst pitch ever.

Um, and he actually went to your college.

Yeah!

I think that's why I remember him. He had that app that was like basically a map of the airport, and it would help you like find restaurants.

And he remembered, and he was like such a classic millennial, like needing validation.

And then he went back and he was like crying in his mom's arms!

Like it was just all so like funny, but he sucked!

And when the app was like... he was going around to different airports and writing down like where there was no real like infrastructure.

Like do you have like memories or things that you like always will remember as being like funny or particularly like terrible?

You know, I get in a lot of trouble for being the mean shark. I'm not the mean shark. I just tell the truth!

Yeah!

When it sucks, it sucks!

Yeah!

Okay, and it's very important that they know it sucks so that they don't do it again!

Stop sucking!

Yeah!

Like try and come up with something better and then come back!

We've had people come back! But it's really a bad idea if it's going to go to zero and you take your family's mortgage down, you know?

Yeah!

It's just crazy!

Well, yeah, you seem like you're very much on like the tough love side of things.

Well, I'm just the truth and if you can't deal with me, imagine the real world. What's it going to do to you?

Yeah!

You're going to get fried! And so that's my attitude. But you know, I gotta listen to Barbara and I gotta listen to Lori.

Yeah!

You know you seem like you love it. Like it's a great part of your job.

Yeah!

But they, you know, what they do is they say, well look, I'm not going to invest in you. This is Barb all the time. I'm not going to invest in you, but you keep doing what you're doing!

And I look at her and say, what are you doing?

Like don't you have any morals?

You guys have such a great dynamic. I'm curious, is that first show and you guys act like that behind, like off the screen too?

You all have a crazy day!

We're like friends. We've been dealing with each other for over 10, 13 years, so we try and be cordial.

You know, but we're competitors!

Yeah!

We're competing for deals and we like each other and all that stuff.

Um, Barbara's a great cook. When I'm in New York, I'll often go and have dinner with her. She's great!

Uh, we're also incredibly busy.

Yeah!

I've never seen all the sharks get in a room during the off season, ever!

It's impossible to get them back together!

Yeah!

Nothing for a birthday party!

Well, we can't! But everybody's so everywhere, and so the only date we know we're going to see each other all together is the first shoot date of Shark Tank when we just clear our schedules and we go do it!

Right?

Yeah! It's such a great show. It's become such like a part of like American culture and like business and the business education I think that especially for us, that I think for so many people like everything we know about business like we know from Shark Tank.

So no one thought that would happen.

Um, certainly most people thought business would be boring.

Yeah!

That did not turn out to be the case!

I remember the moment that it all changed! I'll never forget it. I think it was Boston Logan Airport. I've been doing Shark Tank for three years, no one knew anything about it.

Nobody watched it!

It was just, you know, the only people watching were two dogs and a cat. That was about it, but all of a sudden in year four something happened.

You know, it was the, it was coming out of that really big financial crisis in 2008, and entrepreneurship started to be very hip.

And Shark Tank caught on!

And I was, I went to the, uh, I was with my wife and daughter at, um, at the airport, and I went into men's room, and I, you know, was at the urinal doing my business.

And there's a guy to my right, two over right, and he kept looking at me, and I've noticed he kept looking at me, and he said, are you that guy on Shark Tank?

I said, yeah!

That's the first time it ever happened. He said, you're an [expletive].

And I said, why would you say that?

I said, last night on Shark Tank you took 51% of a startup! That's outrageous business!

Business, I said, hey, it's my money, I'll cry if I want to! What are you talking about?

I said to him, listen, a lot of people make deals in bathrooms, but not here today, my friend!

Right?

I'm gonna run my business the way I see it!

100%!

And he couldn't have known that Lyndon Savannah are out there. He goes outside and I find out later that he said to Linda that Kevin O'Leary's in the men's room!

I didn't know it was your wife!

No, and she said, I know!

Oh my god! No, it's really an amazing show, and I feel like before Shark Tank, entrepreneur meant unemployed!

And now it really means like it's you've shaped a culture around the word, and it's something people want to aspire to be and start their own businesses, and I just love it!

We do! We love you talking about what you've done here because you're the girl that's basically telling everybody you're unemployed!

Yeah!

You're a comedian, which is erratic work to say the best, and then you come in here, you know, with your sister every day and you produce this, which is actually been very successful for you!

So yes, you're unemployed, but you're making money!

Right?

It's a beautiful poetic irony of it all!

It is! But I wonder how many millennials now, even Gen Zers, are going to look at your model, both of you, and say I need to do that because you have control over your own destiny!

Yes!

I think we're living in a world where kids today want to grow up to be influencers, podcasters, because part of the job is to make it look easy.

You know, take beautiful photos, filter everything.

What a lot of people don't see is a lot of the job is boring paperwork like you would do at any other 9-to-5 job.

But influencing is the one industry that's literal sole purpose is to make it look fabulous, make it look fun, make it look easy, make it look, you know, easy road to money and fame when in reality it's actually a lot of work!

And we do a daily podcast, which is crazy because most people do weekly podcasts.

And I can't count on my hand the number of podcasts that launch and never go past 10 episodes.

Even producing one episode a week is incredible hard work!

So it's just one of those things that looks super easy.

Um, and I think that's why a lot of people want to do it: it looks like it's the, you know, the fast track to money and fame when in reality it's like actually the opposite!

But it's more than that because, you know, if you ask millennials, eight out of ten will say I'm going to be an influencer.

You can't just become an influencer! The market is really cruel that way!

It, it, you have to have something about you, maybe you know your story, the fact that you're a comic—that gives the magnetism that creates an interest for other people.

Most people don't have that!

Yeah, well, it's so saturated right now, like it's not only saturated, breaking through even if you have it is next to impossible.

Yeah, getting your first million followers is really, really hard, let alone a hundred thousand!

And so you really can't get traction until you get scale!

Yes, yeah!

And what I've learned, you know, dealing with all the influencers that I deal with and the stuff we do is that, unfortunately for some people, they don't realize early enough that people smell a mile away!

Yes!

And when you get canceled, you're canceled!

Yeah!

You ain't coming back!

Well, we might be back! I actually, whack them all. We wrote the book on cancellation and cancel culture, literally!

And I actually disagree! I think we're living in a really interesting time right now where it's like a rubber band that's going to snap.

I think that for a while it was that case, like if you had even a sting of scandal or controversy, what about all these people that got Me Too'd?

Yes!

So we feel like cancel culture is this huge bubble where we're like always canceling people for saying bad things and doing bad things.

But actually the two of them are incredibly different.

If you were Me Too'd, you are a criminal! Like that is separate!

We're talking about cancel culture, you know, you have tweets resurfaced from when you're in high school, you make a joke that not everyone thinks is funny because, you know, we're living in overly sensitive times.

Like that type of cancel culture is so toxic because, first of all, it leaves no room for growth!

Okay, Roseanne Barr—oh!

Um, I'll tell you why I bring that one up, okay?

She changed forever the morality contracts in Hollywood that I was subject to in subsequent contracts.

You know the story? Just so we bring it to viewers to understand here, and I want to hear your response because, yeah, not necessarily right.

She did! She said something very off-color!

Yes!

Very! That was her comedy 10 years ago!

Yes!

Okay, um, the network that was sponsoring the number one show had 80 million, I think 68 million worth of advertising, the CEO canceled it an hour and a half later, gave all the money back to the advertisers!

Yeah!

Yeah, canceled the show!

That's extreme!

Yes!

Because I do think her tweet was incredibly wrong! Where does it fit in your continuum?

I'm trying to press the—

We like to say that every cancellation is not one size fits all.

I need to know all the details!

So, you know that for that Roseanne thing, like she was a—however old she is, like a 50-year-old woman—like saying something in present times that she really should not have said!

Like I don't, I actually think like her being removed from the show was the best thing for it!

I don't know if the show needed to be canceled in its entirety.

There were other people working on the show, 120 people!

Yeah!

120 people!

Yeah!

They brought it back in, in a different format and I think a lot of people got their jobs back!

But—and it's still on and it's successful!

Look, I'm not endorsing what she said, but I'm pointing out to you that these extremes on cancellation are really serious!

Yes!

And has materially affected her ability to get back into her business!

Yes!

And so it was horrible what she did!

Yes!

That was her comedy!

Yeah!

There has to be consequence!

Like we live in a time, and I think we've all kind of come to the realization we live in a time that's very different than the time that was 10 years ago and we all need to adjust.

And I think that if you're still saying certain things in this day and age, like there are consequences for what you say!

But I don't think that people should be held to the same standard.

You make a joke in 2010 and it resurfaces in 2021, that's not fair!

Well then you're right in that case because I don't think you can be sexist or racist, period!

Not now, not back then, not in the future!

I don't think that's a good thing for anybody!

And I think that's what got her in real trouble because she took something that maybe she thought could pass 10 years ago and tried it out today and then... yeah, done!

So you're the same!

I assume comedy is a really interesting space.

Well, that's what I wanted to probe into, right?

So comedy, like most comedians have podcasts and comedy and podcasting couldn't be more different.

Comedy is no holds barred! You people fight for the right to say whatever they want because it's a joke!

And you should be able to make a joke about anything whereas podcasting comes from the digital space, and the digital space is so sensitive.

There's many classic comics that are really, really on the edge: Dave Chappelle, on the edge on sexist, racist stuff!

Like can you do—you can't do that anymore!

No!

My talking about comedy in the comments, really laying it out there, my personal style of comedy is very specific and intentional.

Like, I do self-deprecating comedy!

I make fun of myself because no one can be mad at you if you're making fun of yourself!

You're not offending anyone!

I'm literally just defending myself!

Okay, so you think those comics have to change, they can't do their traditional routines anymore?

I think comedy is like the last remaining corner of the earth where you can say crazy things!

But I don't think it'll last long!

It's already very touchy!

You're saying it won't last long?

Yeah!

One won't!

No!

Still, I think a frontier that's in question.

I think people are sticking up for the right to joke about what you want to joke about!

And then there are people who are like, we—you can't make jokes about that!

And I think depending on the comedian or depending on the celebrity or influencer, when we say like you can be canceled and you can come back, you have to pull yourself up by the bootstraps.

No corporation's going to give you a job!

No!

What brand is going to endorse you?

Like you need to make your own best for yourself because the industry in the world that we live in is not going to give you canceled in a sense.

You can't go into mainstream, you have to do it yourself!

Yes!

And you need to find your audience and you, like, you have to start from scratch and then you build something that is impenetrable!

You are in charge of your own destiny!

No one can cancel you because you own your own show, you make all your own revenue, you make your own merch.

Like you don't rely on any other company, a larger company!

And we're, you know, in these extremely sensitive times like that's corporate culture!

Yeah!

I think this model you've developed for yourselves actually proven it out is very desirable for many people who want to control their own destiny!

Yeah, I think you work harder than you would in a corporate environment!

You have more risk in your life because you don't know what can happen!

You have to put up your own money when you start it and you also may make one mistake and get fried and have to start again!

Yeah!

But the beautiful thing about the internet is that like it's just the Wild West!

So you can do anything you want and there's so many people on it!

Like we've just kind of cycled through so many different stages of our business, we're entering a new one every week!

Like that's just, you have to keep up with it!

And like you have to shed your old skin and just keep moving forward if you want to stay in this industry for a long time!

I think you do, don't you?

Of course!

You've bypassed all the traditional media!

Like it used to be you'll never get on this network again, you'll never get this, you'll never get that!

And it was all controlled by Hollywood agents and all that stuff!

Into a certain extent, television still is that way, but you know I have more followers now than most of the networks I'm on!

Yeah!

Right?

And it's a strange phenomenon that, you know, I can reposition that content, modify it somewhat, and get to a brand new audience in a different way!

Yeah!

I'm not sure the model doesn't keep going in that direction and that, you know, linear television continues to decline as social...

You know, this is kind of like social network itself, you know, every influencer, podcaster, whatever becomes their own little media industry!

And the bigger you get, you do almost have more reach!

Think of like podcasting versus radio!

Radio is, you know, huge. A lot of podcasts reach more people than traditional radio shows do.

Podcasts used to be framed, you know what I like to—I get invited on a lot of podcasts including this one, and what I like to do is resist the temptation to go look at all the previous podcasts.

I don't want to know anything about you when I show up here!

I mean, I met you for a few hours, right, on an island. I thought I was thoroughly entertained!

But I want to go in fresh!

Yeah!

And then later, you know, if we start doing it over and over again, I kind of get the groove of where it is!

But I've been much more successful doing that in terms of engaging!

And podcasts aren't just audio anymore, they're video!

Yeah, that's what a podcast is, it's just another television show!

Yeah, literally!

And my attitude is, it's much fresher when you go in cold!

Yes!

I agree!

You know, I hate all the scripted stuff and everything else!

I just did the Pomp's podcast in Miami last week. We had a crazy amount of fun because we said no questions pre—you know, set!

Yeah!

Let's just see what happens!

Yeah, yeah, that was fun!

That's the way it should be! Definitely a refreshing format!

You're not bound by those restraints of even cursing, like something as simple as that!

Right?

Time constraints!

Like you can really go for topic matter! Who knows where you go, right?

Right, exactly!

From wine to Roseanne Barr!

Yeah, exactly!

But I think those are serious issues!

Let's go back to wine because I want to taste, I want to try, I want to give you...

We're going to start with the Chardonnay, even though it's not chilled, but this shard just won its fifth gold award!

Oh wow!

Now let me tell you something about the wine business just before we pour this.

Um, 97% of wine in America is sold for under $14.99 a bottle!

Wow!

Nobody knows that!

That means 3%, which is virtually nothing, are those expensive wines.

The challenge becomes how do you make a wine that tastes like it's worth $60 that you can buy for $11?

And I spent a lot of time on this because I wanted my return rates, because I'm going direct to consumer, to be less than 2%, which was my goal.

They're significantly less than 1%!

Wow!

So that means I have to kind of adapt to the palette. Most women drink Pinot Grigio and Chardonnay. That's, you know, they drink whites.

Yeah!

So you need to work with a lot of women to stamp, like I'll blend it, I'll try it on my wife, try it on her friends, then do some serious taste testing sampling to get the vibe from what a Miami woman says versus a California woman versus somebody in Champaign Urbana to try and nail down do I have it?

Yeah!

Because I'm blending these wines, I'm adding little elements of other varietals to get that flavor.

About five years ago I hit it big when I started taking less, you know, when you put Chardonnay into an oak barrel, it gets buttery, oaky, and women were moving away from that.

They were saying give me something fresher, it's too heavy, you know?

And I went in that direction and then I started winning the awards.

Oh, I'm so excited to try this!

I'm usually not a huge Chardonnay fan, but I love Sauvignon Blanc, Pinot Grigio sounds sare, but if you're saying this isn't like a buttery heavy Chardonnay—

Way off in that direction, which is actually classic Montreshe style, which is what the French do in the DRC region of France.

So let's try this!

How much is that bottle?

This bottle, uh, tonight—The reason I'm talking about it, when we go public we're going to do a giant sale on QVC. Normally it would be $15.99, tonight it's gonna be $11.12.

$15.99 is still a great price!

It's, but that— we're going to sell. I did something remarkable a few weeks ago on QVC, in 20 hours we sold $5.2 million worth of it!

Wow!

Yeah!

Did you work with Lori?

No, I worked with Mr. Wonderful!

Yeah, no, listen, you know I'm the wine guy in QVC now because I think people trust me when I say I have your back.

I really know what I'm talking about!

I would trust you like to choose a wine for me!

Will you also show us the right way to taste wine without looking like a fool?

Absolutely! Great question!

We have these—we have these coveted glasses, which are fantastic!

Yes!

So normally you would never overfill a glass of wine. You have to leave enough space for the air to mix with the wine so you can swill it a little bit.

Good to know!

It smells delightful!

Yeah! Now let's do this because this should be chilled, but it's not because it came to the studio.

Um, now the nose you should be picking up some apricot and apple here.

Yeah, okay!

So now take a little bit and just let it roll back in the back of your tongue.

Stunning nectar from the nipple of Aphrodite!

No, it's really delicious!

So good!

It's fantastic! I actually don't drink wine, but crisp it is, it's not over sweet.

It's towards what you liked in the dryness!

Yes!

This is a monster for me—this wine is my number one seller in white!

Really?

It's delightful! It is delicious! Stunning color as well!

Yeah, it's beautiful!

And so you know this kind of wine would be fantastic with cheese. It would be great in the summertime, terrific with chicken. People like to drink it!

I always drink a glass of white at four o'clock when the market closes, and I have one, sometimes two, and then I go to my reds.

So we're going to go to red next!

Okay, well this was Chardonnay, it was good, stunning! And here sometimes you can be a realization, stick your pinky out like this when you're drinking.

See that?

Oh yeah!

Because we're fancy like that!

Exactly!

And you know you're drinking with a dork when you do that!

Yes! Someone uncultured!

Yeah! And now this is a Cabernet Sauvignon known for being the big spicy American red, you know, for with meat and just a big bold statement—

And what you're looking for here is, um, peppers and tannins and leather and just richness!

And get this by blending it!

Again, and so many people don't understand that to get the tail of the flavor, you have to, you know, maybe you sneak in two percent Pinot or maybe you put in a Syrah or something, you have to blend.

You have to sit in the cellar for days with your testimony and try different stuff while not getting inebriated because you start—you stop sensing the flavor.

So most of the time I'm tasting one and spitting it out, spittoon!

So here we go! Now this is going to have a huge nose, also five different awards on this one!

Oh wow!

The red wine with the white carpet is...

Yeah, when's the last time you did a wine tasting here?

Never!

Never! We've never done it on the show!

Okay, so here we go! It's good to start with the best! It can only go down from here!

Yeah!

All right, so again smells lovely!

We really want to, you know, definitely—

Yeah!

I don't want to see that drop!

Yeah!

Okay, now this is going to have, um, a peppery kind of spice to it and the more if you waited 10 minutes it would even be more bold because it's just airing!

This is going to be really good, I can tell!

Okay, let's go!

Ready?

Oh wow!

That is fantastic!

It's very good!

It is! You know I never drink red wine but it's very good!

Isn't that delicious?

Yeah, people tell me all the time I really taste the pepper!

Yeah, you see it! It's there! That took a long, long—many years I've been doing this wine for seven different years of different varietals and started winning about four years ago when I started blending.

But you know you've got to try new things in wine and by the way, the health attributes of one glass of red a year, a day, forever, all year long works in longevity!

Yes!

It's good for your heart, everything!

And so you don't have to get drunk! You can just drink one glass of nine ounces of red wine a day and almost consider it medicine!

You also could get drunk if you want!

Well that happens to me quite often!

Oops!

All right, so where can everyone buy O'Leary wines? On QVC you're having a big sale!

Well, there's what I've learned is this is the business side again: wine is three tiers of distribution, so I used to give all my profits to distributors.

Then I learned how to sell direct when I got my social chops together.

And I started small but now I'm huge!

So you can buy O'Leary fine wines at shop Mr. Wonderful starting tonight at midnight!

Wow!

We do our big sale, and that site’s going to stay up forever!

We're announcing it at the NASDAQ at four. You're getting a sneak peek!

This won't be up until tomorrow!

Anytime on QVC.com!

Fabulous!

Largest purveyor of wine, and we ship it to you directly!

Wow!

That's pretty awesome!

It is great! A lot of people go on to the program where they get shipped a case every 60 days.

Excuse me!

They sit—they put it in a laid down kind of wine cellar box. You stick it in the back of your closet, boom!

You got wine all the time for forever!

Yeah!

[Music] Claudia and her sister were fantastic!

I mean it was quite impressive of what they built up there! They're basically their own network!

So she controls it, she publishes out the content, she makes money!

Um, it's really quite remarkable!

But what's relevant about her and her sister, they know what they're talking about!

So their content really means something because it's either heartfelt or it's factual!

And I think that's probably a pretty good rule to understand about if you're going to be putting something out every day, you've got to have a lot—a lot of topical matters!

You know something about her, do some research, but clearly they have!

Plus they're fun!

That was a gas! I really enjoyed it and got to promote my wine, which I thought was terrific, and talked about a lot of interesting things!

I'm glad I went there!

Where am I going dressed like this to close the bell at the NASDAQ?

Why? Because Vintage Wine Estates, the company that makes all of O'Leary Fine Wine, is going public today!

Fantastic!

Bringing the bell is an honor! Celebrates capitalism! Celebrates both business! Celebrates entrepreneurship, particularly at the NASDAQ!

What a wonderful thing to do!

And then what are we gonna do?

Oh yeah baby! We're gonna drink some very fine wine!

Patron, the CEO, is going to ring the bell!

It's a big deal! This is actually the first day of trading for Vintage United States!

Incredible!

Stocks up almost 20%—very good sign for the future!

Spectacular!

You know have been controversial but not this one!

This one has gained value since it got announced, which is absolutely great!

Glad to be a shareholder!

[Music] Here's the secret about the very fine wines: you can't do that without having a huge infrastructure behind you!

The ability to ship tens of thousands of cases on a wine sale that's really hard to do!

How does it happen?

This guy!

This is Pat Roney! I met him years and years, a year and years and years ago, introduced by Costco!

And we started a partnership!

And wow! Wow!

Where does it end up? Here we are ringing the bell at NASDAQ!

It's incredible!

It's a wonderful outcome!

I want to say thank you Pat!

I want to thank you!

Thank you Kevin! It's been great!

It's been so much fun working with you on all of your wine!

Well, the best is yet to come, right?

Yeah, exactly!

Yeah! More exciting!

We have really big plans because we're going to expand this direct to consumer!

I want to be a part of that!

That's the amazing thing about the new world! Selling direct to consumer cuts out all the middlemen!

The margins are much better, the business grows, and you have a relationship with your customer!

That's the plan!

That's the plan!

Absolutely the plan!

I'm looking forward to executing that plan!

It's a lot of exciting plans!

And hopefully, we'll get to and some of those very soon!

And it's all about the grapes!

Yeah, it's all about the grapes and wonderful wines!

That's Mr. Wonderful! If you like that video, wait—did you see my next one?

Don't forget to click right over here and subscribe!

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