How to Get Customers to Give You Extra Money

Every business eventually has to raise prices. It's not fun but in a world where inflation exists, it's necessary.

So how do you raise prices in a way that won't irritate your customers? Simple. You do it in a way that aligns with your values as a company, and rewards your loyal customers for supporting you.

When Dropout.tv decided to raise prices in 2025, they released a video that explained what what happening, and something incredibly strange happened. As a subscriber-based streaming company, you would expect to lose subscribers when you raise prices. For example, in 2022, Netflix lost around 200,000 subscribers when they increased their subscription price. However, when Dropout raised their prices they didn't see a significant drop in their subscriptions. In fact, customers filled comment sections across the internet to tell Dropout "Please let me pay you more!"

That's right, when they raised prices, they had thousands of people demanding to pay MORE money for their service. How did Dropout create a fan base that is so loyal they were practically throwing money at Dropout? It's simple. Ethics and Alignment.

If you aren't familiar with Dropout, it's a streaming service featuring improvisational comedy from a core troop of comedians. Shifting their offerings from ad-based, free-to-watch content on Youtube to a subscription-based streaming app showed that loyalty can be earned, and can even make a profit. But it requires your company to align to values, and that you must make decisions based on continuing to support those values even when it is less profitable.

Dropout has built a fiercely loyal following based not only on the quality of their content, which is hilarious, but also based on ethics and loyalty.

Ethical Alignment

If you want to create a brand that fosters this kind of loyalty, you have to do more than just create a great product. Our world offers so many choices that are all high-quality and convenient that those aren't differentiators anymore, those are expectations.

If you want to create a brand that people are willing to spend a premium price for, you need to look at the values you are embodying. People are more aware than ever of the power of their money and are choosing to support companies that use that power in a way that supports their world view and ethics.

Dropout not only provides a product that people like, with a cast of comedians that they love, but they do it in an ethically progressive way, and they are very upfront about it. Their CEO Sam Reich is the defacto spokesman for the brand, and is frequently talking about the ethics of the brand in interviews. Dropout makes it a point to pay their creators more than they have to. In the last couple of years, they also offered profit sharing for everyone they've hired. They also allow and encourage their on-air talent to support causes they believe in, letting them promote causes on-air, and even promoting them in social networks. Even with the price increase, they showed their ethics on their sleeve by raising prices for new and returning subscribers only, not the current subscribers.

The Risks of Alignment

These decisions could have been trouble for Dropout. Paying more than necessary, letting your talent and representatives promote their political or ideological beliefs, and leaving money on the table by not raising prices on your subscribers are all choices that could result in a drop in your profits and hurt your brand.

Instead, Dropout was forced to create a new revenue stream for people who wanted to pay them more money. They created a new subscription called the "Superfan" that offers subscribers an "optional ‘pay more if you feel like it’ tier." The benefits of this subscription are very modest. Discounts to merch, behind the scenes content, and early access for event tickets.

The real draw of this subscription is not any of those benefits. The draw (for many fans) is the chance to support a company that aligns with their personal values and ethics.

If you want to earn that kind of loyalty, it's not just about being a good company, it's about being a company that stands up for your values. Your customers are looking for ways to feel good about the companies they support. If your company drops the ball when a controversy happens, or when your values are tested, then your customers will drop you, just as fast.