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

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kevin o'leary boston interview

Photograph by Miller Mobley

Kevin O’Leary only wants the best. So when the waiter at Taj Boston arrives at our table, O’Leary doesn’t look at the wine list; he simply tells the young man that he wants the finest bottle of chardonnay in the house. It’s a Wednesday afternoon and O’Leary is decked out in his patented black suit and black tie. Earlier in the day, the investment mogul delivered a speech in the Financial District, and soon he’ll head to L.A. to start filming the eighth season of ABC’s Shark Tank, which premiered in September. When our waiter returns, he’s holding a 2015 bottle of Jordan. Almost on cue, Mr. Wonderful stares him down as if he’s a contestant on the show and turns on that signature charm: “That is your best chardonnay?”

Do you consider yourself a Bostonian?

Here are the facts: I’m an Irish citizen. I’m a Canadian citizen. I moved down here in ’92 and had my kids here. I spend 181 days of the year in the U.S., and when the weather gets good in Canada I go back there. But I also live in Geneva for a period of the year. I live in L.A. for three months. So I’m all over the place. But Boston is a really special place for me, particularly down here, because I like the Common. I can walk across that park and raise 100 million dollars. Think about it. There’s no town like Boston.

How often do people stop you on the street and pitch you ideas?

Every day, but I tell them right away, “Don’t pitch me.” The rules of Shark Tank are that we can’t see the deal before it airs and [contestants] have to sign a deal saying they didn’t ever pitch a shark. We’ve had situations where people have walked onto the set and some shark says, “You talked to me last week, you’re off.” There’s a big misconception that we know about these deals beforehand, but we don’t.

Is Shark Tank the ultimate racket, given that you’d be doing the same thing if the cameras weren’t around?

Yeah, it’s crazy. But here’s the difference: The real game of Shark Tank is zero customer acquisition costs, and the best model is [Hanover-based] Wicked Cupcakes. The company was not making any money and nobody had ever heard of it. The cost of them acquiring a customer online was higher than the value they got from selling cupcakes. But they got on Shark Tank, their customer acquisition costs went to zero, and their business increased tenfold.

Speaking of baked goods, in one recent episode you tore apart a gluten-free pancake mix. Is your beef with gluten-free foods or with the trend of gluten abstinence?

There’s a lot of bullshit in that market. A food product that tastes like shit is going to fail on the market. That pancake stuff was like eating sand, and it was absolute shit. We make gluten-free cupcakes at Wicked. We spent two years getting it right so it didn’t taste like shit. It was very expensive and we had to have a gluten-free kitchen to do it. But I think that market is overblown—it’s a bunch of people thinking they can lose weight by eating gluten-free. It’s not true.

If you were a fledgling entrepreneur, would you pick Boston again or head for the West Coast?

I’d put Boston up against Silicon Valley any day. There’s a trillion dollars in a square mile here. What always attracted me here is the talent pool. You’ve got MIT for engineers and Harvard for business leaders. I mean, it’s just jammed with talent.

Could there be too much talent, or perhaps too much young talent?

No. You want seasoned managers and you want really strong talent coming in. You want both, and you’ve got both here. The problem with Boston is the costs are insane. It is one of the most expensive cities to operate in in the world. So a lot of our families are out in Waltham or farther out—and then you’ve got to drive in this insane traffic every day and start shifting your hours just to accommodate the insane traffic.

Have you ever been tempted to buy an NBA team just to mess with fellow Shark Tank star Mark Cuban?

No, because in the NBA you don’t make money operating teams; you make money selling them. So you’ve got to sustain losses even when you’re winning, and I don’t like losing money. So the premise is you buy the team for, let’s say, $600 million, and a decade later it’s worth a billion. That’s the investment thesis. It’s been working so far, but I think at some point the law of large numbers is going to slow it down.

So what do you splurge on?

My guitar collection is pretty amazing. I mean, there’s a lot of stupid money in those things. I used to be a shareholder in Fender, so when I got on Shark Tank, I convinced Fender to build two Shark Tank guitars. There are two serial numbers, 001 and 002, and I own them both.

Do you cringe when you see someone playing a rare guitar?

No. You have to play them or they lose their soul. I have all my guitars hanging up in one of my offices—they’re all in tune and I just pull one down and I play it.

If you were an actual shark, which species would you be?

Great white, for sure. I don’t mind eating small stuff. I’m okay with that.

You’re a huge Patriots fan. How did you handle the news of Brady’s four-game suspension?

I was insanely pissed. And I wanted him to appeal it right to the Supreme Court. The whole thing is bullshit; everybody knows it.

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.

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