With something more simple, like your cable bill, play hardball for a better package or fewer fees. For example, if you are paying for channels you don't watch, "call up your provider and say, 'Tell me about your other packages, because if you don't give me a better deal, I'm leaving,'" O'Leary says.
"I've done this my whole life," he says.
"Believe me, they will hop to. They want to know what it's going to take to keep you as a customer, and you want a reduction in fees. You're going to find a happy medium pretty quickly. You'd be surprised.
"Your job is to squeeze a cost cut and a savings out of them," says O'Leary. "You can do it. It works."
In terms of bigger loans — like a mortgage or business loan — O'Leary says you can try to negotiate your way out of lender's fees. Start by saying you simply don't want to pay the fee, O'Leary suggests, and if they don't budge, offer half of what they are asking for. You'd be amazed at what you can get simply if you just ask for it, he says.
"You can push back hard on that," O'Leary says. "They want to loan you the money because the core profit is the interest they charge you."
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