Q&A: Shark Tank’s Kevin O’Leary

Kevin O’Leary photo provided by ABC

Kevin O’Leary sits in the center chair with his hands in a V, fingertips touching, gently tapping together while he listens to a business pitch. The venture capitalist and star of ABC’s Shark Tank has in recent years become a bit of a moderator for the group; the king of all sharks. The other sharks treat him like a bully, and make fun at his expense, but their yapping rolls off his back like the sweat of one of the entrepreneurs trying to make a deal.

The opening segment of Shark Tank says that O’Leary turned a $10,000 loan into a software business worth billions. But what most people don’t know is that many of those deals took place in Back Bay. And all of them at the same table.

The brownstone-loving, Marlborough Street-living shark’s new book, The Cold Hard Truth on Men, Women, and Money: 50 Common Money Mistakes and How to Fix Them, was released this month and offers an inside look at O’Leary’s financial wins and losses, as well as the lessons he’s learned along the way. We talked to O’Leary about venture investing, his love of the Patriots, and how to make it out of the Shark Tank with a deal.

You’re from Canada, but you moved to the Boston area in the mid-’90s. What was it about Boston that drew you in?

We lived in Chestnut Hill and my kids went to school there when we were building The Learning Company. And then we moved to the Back Bay after we sold the company to Mattel in 1999. I wanted to live on Marlborough Street.

Who doesn’t?

Exactly. I like to walk everywhere. From Marlborough Street, or anywhere in the Back Bay, your life is on foot, which I think is the most beautiful thing about this city. My dentist, doctor, everything is right there. Shopping, wine, food is all within a couple of minutes’ walk. I barely use a car in Boston. I have homes in Toronto, Geneva, and other places, but Boston is home. In fact, my favorite home of them all is on Marlborough Street because I love living in a brownstone.

Was the Mattel deal the first big deal that put you on this path?

It got me going as an investor and entrepreneur. In Boston, we have great technology, but we also have biotech, medical devices, and more. There’s a trillion dollars in investments in one square mile. It’s a fantastic city for financial services.

Where did the nickname “Mr. Wonderful” come from?

We are all trying to figure that out. This is what seems to be consensus now: In season one, someone was trying to sell a publishing deal to us for music and I proposed an aggressive 51 percent equity position because I wanted control of the business. And Barbara [Corcoran] said, “Well aren’t you Mr. Wonderful?” and I said, “You know what Barbara, I am!” Now it’s at a whole new level. I show up at hotels and my reservation is under the name Mr. Wonderful. They don’t even know my real name. That’s just nuts.

Where do you make deals in Boston?

My number one spot for getting deals done has always been the Ritz, which is now the Taj. There’s a table in the back corner where every deal that’s been important to me has been done. So when I’m closing a deal or meeting somebody for business, we go there. It’s a special table, and the reason I like it is because I can watch the front door. This way, when my guest arrives, I can wave them over. I don’t want to move away from that table because it’s got the right karma. I’ve brought the same pen with me since 1995.

So you’re superstitious like a true New Englander?

It’s a routine, and I don’t want to ever jinx it. It’s a very important spot.

Any favorite restaurants in Boston?

For anybody that’s coming in from out of town, it’s always Grill 23. I always sit upstairs across from the bar so I can watch the game while I’m eating. I’ve tried every restaurant in town, but [Grill 23 and the Taj] are ones I keep going back to over and over again. I’ve known the doorman at the Ritz [now the Taj] for 20 years.

What game? The Red Sox?

I like the Sox, but I’m a huge Pats fan. I never miss a game. Wherever I am in the world, I figure out how to watch the Patriots, and believe me, it’s been complicated. I’ve had to use Slingbox and all different kinds of technology. Whether I’m in Europe, Asia, or Cambodia, it doesn’t matter, I watch the game. I don’t care if it’s 2 a.m. or 4 a.m., I never miss the Pats game.

Hardcore. Just like your personality on the show. 

Here’s what I am: I tell the truth about money all the time. I don’t believe there is a gray area when it comes to money. It’s black or white, and money is binary. You either make it or you lose it. People say I’m heartless, but I’m not, I’m the only one up there telling you exactly what’s going to happen to you, and if you don’t want to hear that, I couldn’t care less. I’m not trying to make friends. If you want friends, buy a dog. I’m trying to make money.

Some of the other sharks seem to gang up on you. Is that for show?

I enjoy the whole engagement. I’m having more fun on Shark Tank than I’ve ever had in my life. It’s what I love to do.

How much have you invested on Shark Tank?

We don’t disclose how much we’ve invested, but it’s a lot. I think this year is almost double in terms of dollars invested compared to last year due to the size of the deals. I think America figured out that Shark Tank is the American Idol of venture capital. If you can get on the show, even if you don’t do a deal, your product will still go through the roof.

The women behind Wicked Good Cupcakes recently said, “When we first made the deal with Kevin, it felt like we were making a deal with the devil, but he’s like an angel in disguise.” They’ve already paid you back your full investment in less than a year. Are you still a part of the company?

Absolutely. The great thing about Shark Tank is that it changes lives. When you back a successful entrepreneur and create 40 jobs, you are creating the new America, and the country is learning with us as we go through it. Because venture investing in itself is inherently risky and Wicked Good Cupcakes is a family business, I didn’t want any equity in their business. That’s because I don’t want to get involved in the discussions they have as family. Business has skyrocketed, and I trust those women to run the business how they want to 100 percent. They’ve paid back my investment, but I still get 45 cents a cupcake.

O’Leary on set last season with Wicked Good Cupcakes. Photo provided by ABC.

How much do you know about a business before they pitch you?

Nothing. We don’t even see the displays. They hide that from us until the second they walk in. I think why the show works is that we are watching the deal just like you are at home. The only difference is that the pitch may go on for an hour or longer, and the editors masterfully create that whole deal in six minutes.

Are there any tricks to leaving the tank with a deal?

If you look at what gets funded, there are three attributes that are always present, it’s sort of like a little study I’m doing. In every case, the entrepreneur was able to articulate the opportunity in 90 seconds or less. Secondly, they were able to convince the sharks that they can execute. And third, they knew their numbers.

What’s your favorite investment of all time? 

Next weekend is the Berklee gala. I’m a big supporter of that school. They have a gala every year that is the coolest event of the year. It’s a traditional dinner at tables, but after that, all of the students get their instruments and play right in the hotel. It’s the most incredible event of all the galas I go to all around the world. It’s the one I look forward to most because you are going to hear the best musicians in the world there. The music is incredible. It’s a true jewel of Boston. It’s one of the best investments I make every year.

Shark Tank airs Fridays at 9 p.m. on ABC. You can find Kevin O’Leary’s new book, The Cold Hard Truth on Men, Women, and Money: 50 Common Money Mistakes and How to Fix Them, in stores and online.