If you’ve noticed your internet bill creeping up, your airline miles shrinking in value or your streaming subscription suddenly costing $5 more, you’re not imagining things.
Across industries, companies are quietly squeezing more revenue from long-time customers while offering sweeter deals to new ones. Experts call it the “loyalty penalty” — and it could cost you hundreds or even thousands of dollars a year [1].
It may seem like there’s no way to prevent it, but there are strategies that work. Investor and Shark Tank star Kevin O’Leary says he relies on one simple call to stop his bills from climbing — and most consumers can use the same tactic.
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The loyalty penalty
From airline miles to home internet plans, companies have learned that keeping you hooked is cheaper than winning new customers. But instead of rewarding your loyalty, many quietly raise prices while banking on your inertia.
- Streaming services: Major players like Netflix, Disney+ and HBO Max raised prices by about 20% in 2024 [2].
- Internet and cable plans: U.S. households now spend an average of $1,063 a year on internet and cable [3]. These costs typically climb once promotional rates expire [4].
- Car insurance inflation: Car insurance rates peaked at 23% in 2024 [5], which was driven by higher repair costs, pricier replacement parts and rising litigation expenses.
- Airline loyalty programs: Points used in these programs for loyalty perks have been devalued by an average of 36% since 2019. Even long-time frequent flyers find it harder to redeem rewards without paying extra fees.
Why Kevin O’Leary says you should always ask for a retention officer
When bills rise, O’Leary says it matters who you speak to.
“I always call on a bill and say, ‘Let me speak to your retention officer.’ Avoid dealing with the sales rep, because only the retention officer can cut the deal,” he said.
O’Leary isn’t exaggerating. Retention officers, sometimes called customer retention specialists, exist for one reason: to prevent you from leaving. Unlike front-line reps, they often have the authority to extend promotional rates, waive fees, or throw in extra perks.
According to a report by Outbound Engine [6], customer acquisition can cost 5x more than retaining your current consumers. For example, it costs a company money to pay an employee to come to your home and install your Internet service, as well as paying for the equipment used to do so. An existing customer hands over money every month without costing the company anything extra that a new customer would.
ThinkImpact reports that 65% of company revenue often comes from loyal customers [7], so many businesses offer perks to retain their following.
Vena Solutions [8] reports that when customers do escalate calls, retention teams can successfully keep between 67% to 84% of accounts in various industries by offering targeted incentives.
Read more: Robert Kiyosaki warns of a ‘Greater Depression’ coming to the US — with millions of Americans going poor. But he says these 2 ‘easy-money’ assets will bring in ‘great wealth’. How to get in now
How to negotiate like Kevin O’Leary
You should come prepared when calling your provider. Here’s how to maximize your chances:
1. Do your homework
Start by researching current promotions available to new customers so you know what deals are on the table. You can also get quotes from competitors and reference them during negotiations.
2. Ask for your old rate
You can request your previous promotional price. Many companies would rather extend a discount than lose a customer.
3. Negotiate add-ons
If they won’t lower your bill, ask for perks like free months of service, waived upgrade fees, or bonus loyalty points to offset costs.
Other ways to save on your bill
Even when a company refuses to negotiate, you still have options. Consider switching providers altogether. Services like Rocket Money and Trim can automatically compare rates and even cancel overpriced subscriptions on your behalf.
By bundling services with a single provider (like having a mobile plan, TV plan, and internet plan all with one company), sometimes you can unlock discounts.
Companies are counting on you not to notice rising costs — or not to bother fighting back. But Kevin O’Leary’s advice is simple, and anyone can apply it: Call, ask for the retention officer, and negotiate like you’re ready to walk. With preparation and persistence, you can flip the loyalty penalty into real savings.
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Article sources
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[1]. Business Insider. "Customer loyalty is a sham"
[2]. MentalFloss. "Here’s How Much Netflix, Prime, and Other Streaming Services Have Increased in Price Since 2023"
[3]. Live Now Fox. "Americans spend $164 billion a year on cable, internet services, study finds"
[4]. CNET. "Don’t Fall for These Internet Pricing Traps From Your Provider"
[5]. Yahoo Finance. "Some good inflation news: Car insurance is falling back in line"
[6]. Outbound Engine. "Customer Retention Marketing vs. Customer Acquisition Marketing"
[7]. ThinkImpact. "Customer Retention Statistics"
[8]. Vena Solutions. "Average Customer Retention Rate by Industry (And Advice for Boosting Retention)"
This article provides information only and should not be construed as advice. It is provided without warranty of any kind.