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ABC 20/20 says Kevin O'Leary is a Bosshole!


4m read
·Nov 7, 2024

Well, how's this for a greeting? Welcome to hell! You just met the devil, and that's the friendly version from Shark Tank's Kevin O'Leary. You know the one with a big mouth, big opinions, and very big success. So is the only way to get ahead by leaving a trail of blood in the water? I sat down with Mr. Wonderful to find out.

There's a reason people scream when they see a shark—it's the fear of the bite. "You're pigs; pigs get slaughtered. The next guy's going to walk in here and get my money, and he'll get rich, but not you. Take the money, you crazy chickens!" On Shark Tank, Kevin O'Leary is the bully in the proverbial black hat; it fits him to a tee, and he knows it. "What you see is what you get. I've forgotten about this guy already; bring on the next deal. I'm here to make money."

People say I'm mean, but I really believe this: "I tell the truth. I really tell the truth." "Yeah, you tell it, but you tell it brutally." "Well, what do you think happens in the real world? If you think I'm tough, I'm boot camp for the war they're going to go into when they try and run a business."

"But do you have to be so mean about it?" "I've got a bad rap for that; I couldn't care less." O'Leary has two things most people don't: a ton of money and a desire to bankroll the dreams of entrepreneurs. People like Jeff Cohen, who dove into the Shark Tank pedaling a guitar with a collapsible neck that folds in half. Kevin seems to be a guy that doesn’t like to lose. "Bring that over here." He wants it, but he didn't get it.

Cohen felt Kevin's proposal came with too many strings attached. "I don't accept the deal that's on the table; you're dead to me. When you say no to my deal, you're dead." In typical O'Leary fashion, there was no goodbye hug—"That is a human tragedy, and he's teaching his son that it's a crime; he should be arrested."

You can't help but watch Kevin O'Leary on Shark Tank and wonder, is this all an act? "This bullying, it's not an act, and I think of myself as the Merchant of Truth. I really do." Outside the tank, the 58-year-old is the man behind O'Funds, a billion-dollar mutual fund company. "Morning, guys! Do you treat your employees and speak to your employees the way you treat the contestants on Shark Tank?"

"Um, yes, sometimes." "Really?" "Yeah, for me, business is war. I want to take prisoners. I want to destroy my enemies. My competitors don’t ever walk in front of me unprepared. Don’t ever get in front of me without your numbers. Never bring a half-baked proposition and waste my time."

But that Caesarian leadership style rubs some people the wrong way. There's even a word for it. O'Leary says it's okay if you don't like a CEO or the decisions he or she makes because they are not here to please you. "Respect and trust are the backbone of a business, not likability."

Every bully has a bully, and O'Leary met his years ago. "I worked for Steve Jobs, and if you think I'm tough, you should have met him." "Really?" "Oh my goodness! He berated me in a boardroom once in front of my own employees. He was vicious—like worse than you on Shark Tank. I am a nothing burger compared to what he was."

But the roots of O'Leary's management style run deep, back to childhood memories of his father, a failed salesman. "He died when he was 37 years old—37—of what? A broke alcoholic, alone in an apartment; that's what happened to him." Before his father died, O'Leary says his parents were in a dysfunctional marriage, so much so that his mother took him and his brother and fled to Europe when he was only seven years old.

O'Leary remembers it like it was yesterday. "I remember being in Oslo one night, and she completely broke down. I mean, just 'cause she was running out of money. She was in total fear, and I could sense it. I said to myself, 'Wow, this is bad. I can’t let this happen to me.' I just intuitively—her DNA passed to me on that fear, and it’s changed me forever."

Years later, her fortunes would change, and she would loan her son $10,000 for the software business he would later sell for billions. "Many people have tried to figure out what I'm worth. I have enough to get by." O'Leary has all the toys that come with success—the cars, the private jets, even a secret location that stores a private wine collection as massive as his ego. "This is what a million dollars in wine looks like."

No surprise—it includes his very own label that is "nectar from the nipple of Aphrodite." Just another taste of the good life for the man they call Mr. Wonderful—a life that includes Linda, his wife of more than 20 years, and their two kids, both of whom will have to make it on their own because Dad isn't sharing the wealth. "Like nothing—nothing! I’ll pay their entire way right through the end of their education, as far as they want to take it. But when that's over, it's over; and good luck."

So if your daughter calls you up and says, "Daddy, you know I'm in terrible trouble? You know I desperately need some money," the answer is no. "Go fix it; go figure it out." Figuring it out is what O'Leary does best. Remember the collapsible guitar deal that collapsed? Well, negotiations continued behind the scenes, and the two sides are now in perfect harmony.

"I love guitars! I knew that was going to be a hit. I knew it! I knew it! I just had to get a piece of it. You know when you really want it, when you really feel it, and you know viscerally it connects? Listen to your gut—that's what I say."

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