After scaling products from zero to millions of daily users, I've made every pricing mistake in the book.
Somehow we can build complex products but pricing them feels like dark magic.
Here's what I wish someone had told me earlier:
The 80/20 rule will destroy you. Most of what drives willingness to pay comes from your simplest features. The crazy part? That stuff is usually the easiest to build. I've watched founders give away their most valuable features for free, then spend years building garbage nobody wants to pay for.
Your pricing anxiety is killing your business. If you need a team meeting to raise prices by 10%, you don't have a real business. Your customers aren't nearly as price-sensitive as you assume they are.
Context changes everything. Netflix costs $17.99/month - sounds expensive until you realize that's 50ยข per day to replace cable. GitHub Copilot costs $10/month. Compare that to a junior dev at $60/hr and if it saves you 20 minutes daily, you're already ahead.
AI completely breaks the old playbook. The "seat-based pricing" model is dead. We've gone from paying for software access to paying for actual work getting done. If your AI eliminates 40 hours of manual work per week, don't price it like Slack. Companies spend way more on people than software - price accordingly.
Stop trying to save customers who are already gone. The best way to reduce churn? Don't acquire customers who will churn in the first place. I started analyzing our longest-tenured users and just focused acquisition on finding more people like them. Complete mindset shift.
Outcome-based pricing is where the money lives. The sweet spot: measurable impact + minimal human involvement = pricing power. Outcome-based pricing is rare today but becoming the standard fast.
The bottom line: You can't just build cool products anymore. You need to build businesses that capture fair value for the outcomes you create.
Growth AND monetization. Not growth now, money later.
What's the dumbest pricing mistake you've seen? I once watched a founder present their pricing page - it had 47 different variables and looked like filing taxes. Their potential customers literally needed a consultant just to figure out what they'd pay. Wild.