Price Raises and Loyalty

July 6, 2026

Why not raising prices on existing customers can be good for business.

The other day I was on X and I came across this post from my friend, Matt:

I think we can all relate on some level. Price increases have become an expected part of life. Matt mentioned how he raised prices at The Events Calendar during his time there, and it made me think about what I would do today if I were running a software company and wanted to raise pricing. Honestly, I'm on the fence.

On one hand, I get the reason for raising prices on legacy customers. Costs go up over time, especially if new functionality is implemented into the plans that are resource intensive. It only makes sense to cover those costs and there's nothing inherently wrong with creating more profit. The backlash on doing so today would be significantly less than in 2016. For better or worse, people are used to prices going up.

But that's precisely one reason why I would consider not doing it.

Standing By Your Customers

As consumers we are getting absolutely beaten down by the subscription economy. Every little thing is being used as justification to raise prices. Heck, sometimes there are no justifications given at all, just a higher price issued by the higher-ups because the boardroom wants to see bigger margins (I'm looking at you YouTube TV).

I'm a believer in doing well by doing good. If it's feasible, I think locking people into the rate that they buy in at (as long as they maintain an active account) falls into that category. Even more so now than 10 years ago. Brand loyalty is difficult to buy, but one way you can do it is by honoring the contracts you make.

If you do decide to raise prices, give people a long enough runway to prepare mentally for the shift – don't just throw it at them. For example, this could mean letting their current contract period end (one year from initial sign-up) before new pricing goes into effect. Also, give them an offramp should they decide they need to move on. If a few folks write into support saying they cannot afford it going forward, give them an extra year at legacy pricing.

In other words, just be human about it all. Nothing is worse than the heartless corporate decision-making that we have become accustomed to today.

#entrepreneurship