© Illustration by Aurélie Garnier
Jonathan Gupta-Buckley is founder of The Twenty One and Kaai, previously leading audience and subscription growth inside News Corp.
Key takeaways to copy & share
> "Subscription fatigue" is the easy explanation when a paid product struggles. The more useful question is whether there was enough recurring value to begin with, rather than benefits assembled to justify a monthly charge > Start with frequency: what do people already come back for. Then use registration as the halfway test, because if your most engaged readers won't create an account, a payment step will not fare better > Build the paid tier around a behavior that already exists, giving people materially more of it. If the pricing page needs six unrelated benefits to feel substantial, no single benefit is strong enough > Be deliberate about what stays free. A story that brings in thousands of first-time visitors has a different job from a specialist product consumed repeatedly by known users, and should be treated differently > Forecast before you keep building. Apply realistic registration, free-to-paid and retention rates to your own segments, and if the range falls short of what the business needs, stop before the pricing conversation starts
