When Free Works (and When It Doesn’t): A Practical Decision Framework for SaaS Founders | Joe Wilkinson

Jesse Schoberg is co-founder of DropInBlog, the drop-in blog platform used by thousands of Shopify and BigCommerce brands. Jesse has been featured in Forbes, CNBC Make It, Niche Pursuits and Indie Hackers. We get into whether SEO is dead in 2026, what AI search has changed about business blogging, and where the arbitrage is right now for small brands.Read full show notes or discuss this episode⁠

Most freelancers and agency owners assume a revenue dip is a lead problem. Alan Thomas runs Revpact, where he helps agency founders fix their sales process instead, and after a decade selling at Twitter and Time Doctor he's seen the same misdiagnosis 9 times out of 10. In this episode we get into how to tell a conversion problem from a lead problem, the three-call process that stops freelance and agency proposals getting ghosted, and where AI SDRs actually earn their keep.Read full show notes or discuss this episode

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.Read full show notes or discuss this episode

Mony Chhim is a freelance LinkedIn ads manager and the go-to LinkedIn advertising expert in France, where he also hosts the B2B marketing podcast Marketing B2B (110+ episodes). In this episode we get into why LinkedIn ads require a completely different approach to Meta and Google, how to structure a funnel across cold and retargeting layers, and the specific bidding, targeting, and creative decisions that actually move the needle.⁠Read full show notes or discuss this episode

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.In the meantime, if you would like to support the show, please interact with the guests by leaving comments or likes on their episodes. This will help encourage the guests, and also give me some feedback on what people like to listen to.Thank you again for listening.

Kevon Cheung is the founder of Public Lab and creator of Build in Public Mastery. In this episode, we get into what building in public actually means beyond the surface-level "post your revenue milestones" approach — and how to use it as a real lead gen strategy even when you're starting from zero.⁠Read full show notes or discuss this episode

Paul Xue is a serial CTO and founder who built Space Station Labs into a $500k+ solo dev agency. In this episode, we get into how he structures project-based pricing to escape the hourly trap, how he handles negotiation and pushback, and why he targets venture-backed startups as his go-to client profile.⁠Read full show notes or discuss this episode

Chris McCarron is the founder of GoGoChimp, a CRO agency that's worked with marketing names like Neil Patel and Noah Kagan. In this episode we get into how to actually improve your conversion rates - from diagnosing where people are dropping off, to running tests with low traffic, to the trust signals that most indie products are getting wrong.⁠⁠Read full show notes or discuss this episode

Lana Rafaela is the founder of Cherry Red Content, specializing in post-AI written copy for SaaS and B2B. In this episode we dig into what actually makes a landing page convert - from nailing your UVP to structuring objections, social proof, and CTAs.⁠Read full show notes or discuss this episode

Justin Halsall is the founder of RecordOnce and a former developer advocate at IBM. In this episode we get into what makes a product explainer video actually convert - the structure, the common mistakes, and how to test before you go live.⁠⁠⁠Read full show notes or discuss this episode