Approximately 18 months ago, Warren Buffett was kind enough to sit down with an interview with me. It did not end well. Undaunted, I decided to re-open this series. Today’s guest is Kevin O’Leary.¬†


Nelson: Today’s guest is Kevin O’Leary, former software mogul, current BNN commentator and one of the sharks on the hit ABC series Shark Tank. Kevin is also a regular guest on CNBC, and loves wine so much that he’s recently started his own wine label. He’s also kind enough to include a stock pick for each Sunday Morning Dump. Kevin, thanks for joining us today.

Kevin: You forgot to mention how handsome I am. Both Barbara Corcoran and Lori Greiner can’t resist me. Did you see them throw themselves at me that time you visited us on the Shark Tank set?

N: Umm… I’m not exactly sure that’s how it happened.

K: Are you questioning the story of The Merchant of Truth?

N: Hey, let’s talk about that for a minute. Why do you have so many cutesy names for yourself, Mr. Wonderful?

K: Nelson, here’s the deal. I might seem like an asshole who legitimately wants to murder your puppy, but in reality, I’m the nicest guy you could ever meet. It takes a special kind of niceness to be able to not only tell the truth, but to make people feel really crummy about it in the process. And I have that gift.

N: I see. Okay Kevin, can you talk a little about the differences between Dragons’ Den and Shark Tank

K: Well, they’re the same in a lot of ways, just with subtle differences. On Dragons’ Den the producers would let a few more joke entries in, which was fun for me. You should see how many people I made cry. It got to the point where the¬†producers of the show would have pools to see how long until I made someone cry. Unfortunately I don’t get many chances to make people cry on Shark Tank.

N: Do you like making people cry?

K: LOVE IT. It is my Kryptonite.

N: Okay then. Can you talk a little about why you decided to become an entrepreneur at such a young age?

K: Well, it all started when I got fired from my job at McGoo’s ice cream parlor. I never wanted to give anyone that kind of power over me again, so from that point forward I… I never wanted to work for anyone… (sniffs) anyone else ever again.

Sorry, I get a little emotional when thinking back then.

N: Wait. You’re crying?

K: I’d appreciate it if you didn’t put this part in.

N: Do you not see the irony here?

K: No, but I can see your skull coming into contact with a bottle of O’Leary’s finest.

N: Uhhh…. moving on. Let’s talk a little about your love for wine. I have to admit I don’t care for it.

K: WHAT? THIS IS AN OUTRAGE! YOU ARE A NUTBAR FACTOR 6. HOW CAN SOMEBODY NOT LIKE WINE? It’s the nectar of the gods. I look like such a badass when I drink it, especially when I wear my sunglasses. It just makes all my rich guy problems melt away, y’know.

N: What’s an example of one of Kevin’s rich guy problems?

K: Steve Jobs yelled at me once.

N: Did you cry?

K: No. Only Brett Wilson cries when people yell at him. I made him cry 6 times during season 3 of Dragon’s Den.

N: What’s it like being the only value investor on both Dragons’ Den and Shark Tank, especially when your colleagues feel free to pay up for growth?

K: My fellow Sharks know nothing about value. Cuban wouldn’t know a value investment if it came and played center for his stupid basketball team. Herjavec spends half of every episode giggling like a dumbass, while spending the other half intently staring at you. It’s the creepiest thing ever. All Grenier cares about is whether she can put something on QVC and getting into my pants. I might not get all the deals, but at least I know the ones I get are good.

N: Your relationship on set with Arlene Dickenson can be described as love-hate, like I saw when I visited the Dragons’ Den set. Do you and her stay in contact?

K: Oh, yes. She wants my bald head, if you know what I’m saying.

N: Is that… is that a double entendre?

K: (winks)

N: But she seems like she wants to murder you in your sleep.

K: Hate sex is a powerful thing, Nelson. You ought to try it, I hear you’ve made some enemies in the personal finance space over the years.

N: Wait, what? How did you hear that?

K: Oh, you don’t like it when the HEAT GETS TURNED ONTO YOU, DO YA?

N: This interview is over.


Tell everyone, yo!