Category: pricing
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The free tier death cult
One user consumed tens of thousands in model usage on a $200 plan. That’s from Anthropic’s own admission when they killed Claude Code’s unlimited tier. Not $200 worth of usage. Tens of thousands of dollars on a $200/month plan. TechCrunch said Cursor hit $500 million ARR. Fastest growing application ever, but still losing money on…
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The SaaS pricing apocalypse
You know that feeling when you’re looking at your competitor’s pricing page and the math doesn’t add up? $9/month. Unlimited usage. Same features as your $900 enterprise plan. Your first thought: They’re burning VC money. Classic Silicon Valley playbook – grow at all costs, figure out margins later. You’ve seen this movie before. They’ll either…
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The 5 stages of SaaS death
Last week, I met a founder who’d just lost a pretty big $2M deal to a 3-person startup with a half-finished product (I call these “3 Stanford grads in a trenchcoat”). He was annoyed they didn’t even have a basic dashboard or settings page. I think he wasn’t angry about losing the deal, but mostly…
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Pricing AI Proofs-of-Concept: free pilots will kill you
You know that sinking feeling when a “promising” proof of concept drags on for months, burns through your engineering resources, and ends with “we need more time to evaluate”? Yeah. That’s the PoC death spiral. And I’m seeing so many agentic companies falling into this trap as we help them monetize their agents at Paid.…
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🐙 The 14 pains of billing for AI agents
(Basically, why the octopus grew new tentacles for agentic billing) A while ago, I wrote about the 14 pains of building your own billing system – that was back when billing was “just” complicated. It got mentioned quite a bit around the internet, and ended up #2 on the front page of Hacker News which…
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🦑 The 14 pains of building your own billing system
Trying to cobble together your own billing system is like wrestling an octopus that’s armed with tax codes and invoices instead of tentacles. It’s a beast of complexity that can tangle up everything from customer support to compliance. I have 14 points on why it’s hard.