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 paid
02:40 When free makes sense
05:00 Why “broad free” often produces no monetization
06:00 Using free users for QA vs getting misleading feedback
07:00 The “freeness” problem
08:00 The third path
09:05 How to find the paying segment
12:00 How many responses you need
14:00 Example teardown
18:00 Customer research
19:05 Pricing signals
20:35 Why raising prices is easier than going from free to paid
21:45 Should you start at $1/month?
22:45 Freemium vs fully paid
26:55 Rolling out paid upgrades
29:00 Avoiding product drift
32:00 B2B/enterprise differences
37:15 AI pricing in 2026
40:40 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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