Swipe Files - 📂 How NOT to raise prices

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Nobody likes a price hike, but not every company can survive without one — unless you’re Costco and have a $1.50 hot dog deal written in stone.

For the rest of us, raising prices is a delicate balancing act.

Get it right, and customers stick around. Get it wrong, and, well… just ask YNAB or Drip.

YNAB’s $10 Misstep

YNAB announced a $10/year price increase, bringing their annual plan to $109. While some users shrugged it off as pocket change, others were furious. Why?

It wasn’t about the $0.84/month — it was about perceived value.

The increase felt disconnected from tangible improvements, leaving some customers questioning whether the software was still worth it.

This wasn’t YNAB’s first pricing controversy either. Back in 2021, they faced similar backlash after a sudden price hike.

The CEO even hosted an AMA on Reddit to do damage control, but the move didn’t land well.

Many users felt the announcement could’ve been handled better, and longtime customers started exploring cheaper alternatives.

When customers feel blindsided or undervalued, even the smallest increase can erode trust.

It’s a valuable lesson in how not to raise prices.

Drip’s Disaster

Drip took things to a whole new level.

They doubled their prices, giving customers just 12 days’ notice. To make matters worse, their announcement email didn’t even include the new pricing — customers had to email support to find out.

For loyal users, this wasn’t just frustrating — it felt disrespectful. The backlash was swift, with longtime customers abandoning the platform in droves.

Brennan Dunn @brennandunn 1) Drip really, really screwed up with this one 2) Today I signed up for @ConvertKit - which is something I've been wanting an excuse to do for a *very* long time 3) Keep an eye on http://learnconvertkit.com - going to be porting my advanced automation course over ASAP https://twitter.com/nathanbarry/status/1080853348012572673 Nathan Barry @nathanbarry For everyone considering the move away from Drip after the deliverability issues and price increase, my team is here to help! Just reply here or email me (nathan@convertkit.com) and we'll get you setup with a concierge migration to @ConvertKit. 2:9 PM • Jan 3, 2019 13 Retweets 122 Likes Read 21 replies

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Raising prices without backlash isn’t just about numbers — it’s about communication, timing, and respect.

So, how do you get it right?

Communicate early. Give your customers plenty of notice about the change, so they don’t feel startled and tempted to leave immediately.

Highlight the value. Show what customers are getting for the increase. New features? Better support? Make it clear why the product is worth it — the more context, the better.

Show empathy. Give loyal customers a chance to lock in their current pricing for an extra year or offer transition periods to ease the adjustment. Gratitude goes a long way.

YNAB could’ve framed their increase as part of ongoing improvements or future upgrades, so customers felt the value.

Drip, on the other hand, needed to slow down — offer a clear timeline, explain the change, and maybe even thank customers with a grandfathered rate. Instead of frustration, they could’ve built goodwill.

At the end of the day, raising prices is about more than revenue — it’s about trust. When customers feel valued and respected, they’re more likely to stick around, even when they’re paying a little more.

Have you ever raised prices for your product? What worked — or didn’t? Hit reply — I’d love to hear your thoughts.

Talk soon,
—Corey