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American Focus > Blog > Economy > Is customer loyalty dead or are you just a bad negotiator? How Kevin O’Leary gets a better deal when his bills creep up
Economy

Is customer loyalty dead or are you just a bad negotiator? How Kevin O’Leary gets a better deal when his bills creep up

Last updated: November 15, 2025 4:40 am
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Is customer loyalty dead or are you just a bad negotiator? How Kevin O’Leary gets a better deal when his bills creep up
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If you’ve noticed your internet bill suddenly increasing by $12, your airline miles not stretching as far, or extra fees being added to your streaming subscription, you’re not alone. This phenomenon is known as the “loyalty penalty,” where companies gradually raise prices for loyal customers, costing them more in the long run.

However, there is good news – these price hikes are often negotiable if you speak to the right person. Investor and “Shark Tank” star Kevin O’Leary advises calling and asking to speak directly with a retention officer when faced with a price increase. These specialists are trained to prevent customers from canceling their services and are usually the only ones authorized to offer deals and incentives to retain your business.

Research has shown that retention teams can successfully keep between 67% to 84% of accounts by providing targeted incentives to customers. Companies invest in keeping existing customers because acquiring new ones can be up to five times more expensive. Loyalty programs and long-term relationships with customers generate significant revenue for businesses, with 65% of company income often coming from loyal customers.

The pricing creep is prevalent across various services, with streaming services, internet and cable plans, car insurance, and airline loyalty programs all seeing increases. Major streaming platforms raised prices by around 20% in 2024, while U.S. households now spend an average of $1,063 a year on internet and cable services. Car insurance rates have also increased due to higher repair costs and rising expenses.

Points and rewards programs, along with auto-renewals, can create the illusion of savings while costs gradually rise. Tier systems in airlines and hotels encourage overspending, auto-renew pricing hides increases, and points and perks are quietly devalued over time. Competitors often offer better prices to new customers, leaving loyal customers paying more without realizing it.

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When negotiating with your provider, research current promotions available to new customers, request your previous promotional price, and ask for perks like free months of service or waived fees. Remember that you have options and are not stuck with one provider. Comparing rates at other companies or switching to new-customer promotions can often save you more than a single discount ever would.

In conclusion, don’t be afraid to push back against creeping costs and explore alternative options to bring your bills back down. Loyalty should not come at a high price, and with a little effort, you can ensure you’re getting the best deal possible.

TAGGED:BadBillscreepcustomerdeaddealKevinLoyaltynegotiatorOLeary
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