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.

Subscribe / follow!If you want more episodes on pricing, PLG, and growth strategy for founders, follow the show so new episodes land in your feed.

In this episode, I chat with Mony Chhim, a top LinkedIn Ads pro from France. We dive into the nitty-gritty of making LinkedIn Ads work, especially for B2B companies. Mony shares his journey from being an engineer to mastering LinkedIn Ads, and he’s got some awesome tips on targeting, creative content, and why video ads are a game-changer.

It's here! That's the end of season 4. Many thanks to the guests of this season. Each of them provided very actionable direction on how to apply strategic theories in practice. Based on this season, I need to narrow and define the vision for this podcast moving forward. I may restart the podcast sometime next year.