Kevin O’Leary Talks Boston, Shark Tank, Wine, and Deflategate

He’s cocky. He’s cutthroat. He lives in the Back Bay. Take a deep dive with Mr. Wonderful.

What’s your deepest fear?

I’d like to live a little longer. A lot of my friends are dropping dead. People I know—they’re just gone in their fifties. It’s scary. I would not like that to happen. [At age 62,] I’m just now starting to enjoy the fruits of my labor and I’d like to enjoy them a little longer.

Burgundy or Bordeaux?

I’m a Burgundy guy. I’m a member of a society called La Confrérie Chevaliers du Tastevin, which you’ve heard of probably through Shark Tank. So I buy Burgundies every year and they’re the most expensive wines in the world. I mean, a Richebourg or a La Tâche—they sell for $3,000 a bottle.

Is there a bucket-list bottle of wine you’re on the hunt for?

No. I’ve tried wines from the First World War. I’m very active. I’ve got a group of guys here in Boston and we have a cellar in Cambridge—you’ll never guess where it is. We built it in a building underground. Nobody could ever find it. It’s got millions of dollars’ worth of wine in it, and it’s probably one of the most interesting cellars in America. We buy futures in wine. If you’re getting divorced and have a massive cellar, we’ll buy the whole thing no matter what city you’re in.

So divorces are good for wine collectors?

They are a huge source of wine. A lot of celebrities buy a lot of wine and then they get divorced. They can’t agree who gets the wine, so they sell it and turn it into cash. I buy it. I love divorced sellers—fantastic, fantastic value. And we’re able to go and buy the whole thing and then we syndicate it. Sometimes we go and sell it to the Chinese. We’re very active in buying and selling, so we may take risks on the whole thing and then within a day, half of it is gone.

You sold a psychotic amount of Kevin O’Leary–brand wine on QVC in less than a day.

Broke all records. We grossed $2.97 million—that’s over 40,000 cases. It’s never been done before.

Did that surprise you?

Here’s the thing: For seven years now, everybody that watches Shark Tank knows I’m the wine guy. They know me as the financial guy and the wine guy. The rest of the sharks just swig beer—they’re ignoramuses, they don’t know anything about wine. So there’s that connection with the audience. There’s a lot of trust between the viewer and me. I’ve never let them down, and that’s the key to building a brand.

How hands-on are you with O’Leary wine?

I’m not letting some guy slap my name on a bottle of wine. That celebrity wine game is bullshit. Here’s what happens: Someone has leftover juice in California, they go to an agent and say, “Get me so and so,” and some rock star slams his name on it, and it is piss. That’s never gonna happen to me. I go out there, I blend the wine, and then I sample it. And then I wait until it’s in the bottle and I try it again. It never goes out without me trying it.

And you’ve actually rejected batches?

Are you kidding? If it’s shit, I don’t want to ship it. If I don’t drink it myself, there’s no fucking way I’m selling it to somebody.

Guilty pleasure other than wine?

I don’t smoke. I don’t do drugs. I don’t do any of that stuff. You can’t afford guilty pleasures anymore. I have friends that smoke, and I say to them, “Are you out of your fucking mind?” You’re tempting fate in such a brutal way.

What does the success of Shark Tank, a show that brings us into the early stages of a product’s life cycle, say about contemporary consumerism?

That’s a good question, and I tell you that every producer in a competing network is asking it. They’ve tried so many knockoffs. There are at least a dozen on the market on cable. Here’s my thesis. What are you really watching when you’re watching Shark Tank? You’re watching the pursuit of freedom. What does it mean to be wealthy? You’re free. Even a nine-year-old girl watching the show knows that.

I get vicariously embarrassed when a contestant shares a story of personal tragedy in hopes of gaining sympathy and closing the deal. Does that tactic ever work on you?

It’s all crap. Sometimes when I’m hard on somebody, they start to cry, and I say, “If you can’t take me, can you imagine what the real world is going to do to you? When you get out there you’re going to get ripped to pieces. You don’t have what it takes. I’m just boot camp for you. You’re lucky you met me. I’m your friend; I’m telling you the truth. The rest of these sharks are full of shit; they’re worried about your feelings. I don’t give a shit about your feelings. If you want a friend, buy a dog.” I don’t care if they cringe. What does it matter? It’s either a good business or it isn’t. They’re going to go bankrupt anyways—I’m just telling them way ahead of time. That’s it. It’s that simple.

What’s one thing every person should do before they die?

I think everybody should go to Beaune, France, and walk those streets, which are from medieval times, and drink some Burgundy wine. Because those guys don’t give a shit about anything. They don’t care if the economy is booming or if it’s failing—they just don’t give a shit. And when you get there, you realize there’s some merit to that way of thinking. You’ll find an 80-year-old couple sitting in a bar at 2 in the afternoon drinking a bottle of Burgundy, enjoying their lives.

Could the cold and cunning Mr. Wonderful really embrace such a lifestyle?

I did it this year. I went there for a week and I drank from noon till 2 in the morning every day. It’s just a wonderful release. The cell phone doesn’t work, there’s no cellular tower, there’s no Internet, and they don’t give a shit.

Biggest regret in life?

I don’t have any regrets. I really don’t. I’m the sum of all the parts. I wouldn’t change anything.