At Business of Software, we often hear from founders:
“We’ve built something that people genuinely use and value. But we have no idea how to price it.”
It’s a common and challenging problem. Pricing decisions are rarely straightforward; they come loaded with uncertainty, emotion, and long-term consequences.
This is the part no one really prepares you for.
The Emotional Weight of Pricing
You might assume pricing is a matter of strategy and spreadsheets. But talk to any founder, and they’ll tell you it’s more personal than that.
Pricing touches everything: your product’s perceived value, your brand, your customer base, and your business model. Too high, and you may scare off the right users. Too low, and you risk undervaluing the very thing you’ve worked hard to build.
It’s not just about getting the number “right.” It’s about understanding what your product truly means to your customers, and how to reflect that in the way you charge.
A Trusted Resource from the BoS Community
Years ago, Neil Davidson (co-founder of Redgate Software and founder of Business of Software Conference) faced the same pricing challenges. When he couldn’t find a clear guide to pricing for software companies, he wrote one.
The guide, Don’t Just Roll the Dice, has since become one of the most downloaded and shared resources in the Business of Software (BoS) community. At just 60 pages, it’s clear, practical, and written by someone who gets what you’re going through.
Even if it has been written years ago, Don’t Just Roll the Dice is still relevant and useful not because it gives one magic answer, but because it speaks to founders in a way that makes sense.
A Few Takeaways from the Guide
1. Value > Cost
Your pricing should reflect the value your customers receive, not your internal costs. “Cost-plus” pricing often misses the mark.
2. Segment Your Customers
Not everyone has the same needs or willingness to pay. Thoughtful segmentation opens the door to more sustainable pricing models.
3. Pricing is Perception
Cognitive biases (like anchoring and price-quality assumptions) play a major role in how prices are perceived. Pricing is as much psychology as it is math.
4. It’s Never Final
Pricing isn’t something you set once and forget. The most successful companies treat it as a process: testing, adjusting, and learning over time.
5. Getting it Wrong Has Consequences
Pricing errors compound. The wrong decision early on can shape customer expectations and limit future flexibility.
Get Your Free Copy
60 pages. 1 hour read. Years of pricing confidence.
If you’re figuring out your pricing right now (or helping someone who is), this is worth your time. And if you find the guide valuable, share it with your team.
And if you’ve already read it, we’d love to hear: What was the biggest mindset shift it gave you? Let’s keep the conversation going.
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