Monetization Funnel: Paywall & Onboarding

Adapted from "The Ultimate Paywall & Onboarding Playbook" by Jake Castillo (Founder of Cal AI, July 2026). Cal AI ran 100+ paywall A/B tests and went from $0 to ~$30M ARR. This is the machine that collects the money once marketing brings traffic.

Core principle: the paywall and onboarding ARE the business. Marketing gets people to the door; this funnel converts them into revenue.

When to Use

• Evaluating an existing consumer app's monetization funnel (diagnosis mode)
• Designing the paywall + onboarding flow for a new product (design mode)
• Diagnosing a conversion leak: which part of the machine is broken
• Deciding trial policy, paywall placement, or onboarding length

1. Get the Order of Operations Right