Freemium vs paid pricing is not a “which is better” debate - it’s a commitment question. Joe Wilkinson (AI product growth strategist; ex-Director of Growth at Lucid) breaks down when free works, when it backfires, and how to convert the right users without reducing trust.

In this episode

* How to decide free vs paid vs freemium vs trial based on your business

* Why free users can give bad product signal (and how to find the paying 20%)

* The $1 pricing move: why $1→$5 is easier than free→paid

* How PLG can “sell the service layer”

Chapters:01:00 Free vs paid02:40 When free makes sense05:00 Why “broad free” often produces no monetization06:00 Using free users for QA vs getting misleading feedback07:00 The “freeness” problem08:00 The third path09:05 How to find the paying segment 12:00 How many responses you need14:00 Example teardown18:00 Customer research19:05 Pricing signals20:35 Why raising prices is easier than going from free to paid21:45 Should you start at $1/month?22:45 Freemium vs fully paid26:55 Rolling out paid upgrades29:00 Avoiding product drift32:00 B2B/enterprise differences37:15 AI pricing in 202640:40 Where to find Joe

Resources & links

- Joe Wilkinson: Artisan Growth Strategies- Joe on X/Twitter: @artisangrowth

If you want to apply this

* Audit your current model: are you truly building the free engine or funding paid acquisition?

* Talk to 5 users: “What happened before/after using the product?”

* Add a net-new paid SKU and try to get a real pre-purchase.

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