Joe Wilkinson from Artisan Strategies on Free vs Paid, AI Pricing and User Acquisition Strategy [#29]

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Joe Wilkinson is an AI product growth strategist who scaled SaaS businesses from $3M to over $100M ARR – including as Director of Growth at Lucid where he ran thousands of monetisation and experimentation tests.

He now runs Artisan Growth Strategies, working directly with founders to fix and maximise revenue from existing users. In this episode we get into when free actually makes sense, how to find paying users inside a free base, and what’s changing with AI pricing in 2026.


Timestamps:

  • 00:01:00 – The commitment problem with free vs paid
  • 00:02:30 – When free makes strategic sense
  • 00:06:00 – Using free users for product data – good signal vs bad signal
  • 00:09:00 – How to identify and qualify the 20% who will pay
  • 00:19:00 – Getting real willingness-to-pay signal in conversations
  • 00:22:30 – Freemium vs fully paid – how to decide
  • 00:37:00 – AI pricing trends and what’s coming in 2026

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