Transcript for Do You Work for a 'Bosshole'?
How is this for a greeting. Welcome to hell, you just met the devil. And that's the friendly version from "shark tank's" keven o'leary, the one with the 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. Reporter: 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 is gonna walk in here and get my money and get rich, but not you! Take the money you crazy chickens! Reporter: On "shark tank," kevin o'leary is the bully in the proverbial black hat. It fits him to a "t." And he knows it. What you see is what you get. I forgot about this guy already. Bring on the next deal. I'm here to make money! People say I'm mean, but i, i really believe this. I tell the truth. I really tell the truth. Reporter: 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. Reporter: But do you have to be so mean about it? You know, I've got a bad rep for that, I couldn't care less. Reporter: 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," peddling a guitar with a collapsible neck. Kevin seems to be a guy who doesn't like to lose. If he decides he wants something -- bring that over here! -- He wants it. Reporter: But he didn't get it. Cohen felt kevin's proposal came with too many strings attached. I don't accept the deal. You're dead to me when you say no to my deal. You're dead. Reporter: Typical o'leary fashion, there was no good-bye hug. That's a human tragedy and he's teaching his son that. It's a crime he should be arrested. Reporter: You can't help as you 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. Reporter: Outside the tank, the 58-year-old is the man behind o'leary funds, a billion dollar mutual fund company. Good morning, guys. Reporter: Do you treat your employees, and speak to your employees, the way you treat the contestants on "shark tank"? Yes, sometimes. Reporter: 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. Reporter: But that caesarian leadership style rubs some people the wrong way. There's even a word for it. Stanford professor, bob sutton has spent years researching why bosses act the way they do. When I think of a bosshole, i think of somebody who has some power or authority over someone, and it's also someone who leaves that person feeling demeaned and de-energized. Reporter: They are a staple in television and film. Like those in "the devil wears prada." I feel-zblsh taelts of your incompetence don't interest me. Reporter: "Working girl" -- this girl is my secretary. Reporter: And "glengarry glen ross" -- you are , hit the bricks pal, because you're going out. Reporter: And sutton says life imitates art thanks to real life characters such as movie producer scott rudin -- once labeled thee most feared boss in hollywood for his firing of more than 110 personal assistants. Donald trump, who not only fires contestants on "the apprentice" but once allegedly fired his own co-star for excessive self-promotion. And the very judgmental simon cowell, who wiped out nearly all of the talent on the "x-factor" after just one season. If your boss possesses similar traits, sutton explains how to survive. If you're stuck with at bosshole, advise learning the fine art of emotional detachment. That ability to not only avoid contact, but develop the fine art of when they're acting like a jerk and treating you like dirt, acting like you're not there and pretending you're somewhere else. Reporter: O'leary says it's okay if you don't like a ceo or the decisions they make, because they're not here to please you. Respect and trust are the backne of a business. Not likability. Reporter: 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've met him. Reporter: Really? Oh, my goodness. He berated me in a boardroom once, in front of my own employees. He was vicious. Reporter: Like worse than you on "shark tank?" I am a nothing burger, compared to what he was. Reporter: But the roots of o'leary's management style run deeper -- back to childhood memories of his father, a failed salesman. He died when he was 37 years old. Reporter: Thirty-seven? Of what? A broke alcoholic. Alone in an apartment. That's what happened to him. Reporter: Before his father died, o'leary says his parents were in a dysfunctional marriage. His mother took him and his brother and fled to europe. Only seven at the time, he remembers it like it was yesterday. And, I remember being in oslo one night, and she completely broke down. I mean, just, because 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. Reporter: 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. I'm okay. Reporter: 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. Reporter: 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 will have to make it on their own, because dad is not sharing the wealth. Reporter: 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. Reporter: So if your daughter calls you up and says, "daddy, you know, I'm in terrible trouble, I really, you know, i desperately need some money." The answer is no. Go fix it. Go figure it out. Reporter: "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 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, buy. That's what I say.
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