# Jonathan Courtney

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I CRIED on Camera Reviewing 2025's BIGGEST Wins!

Hey everyone! This week is a little different. I actually made a video post. Watch my raw, on-camera Lightning Research Review of 2025’s top Substack insights—it’s a fun, visual recap using a Miro board you can explore yourself. I time-boxed it to highlight eight game-changing artifacts with quick …

How I use AI Marketing and Claude Code to make $$

I sit down with Jonathan Courtney, host of Unscheduled CEO Podcast, to talk about the gap between building AI-powered products and actually making money from them. Jonathan walks through his four-step "Promoter Blueprint" — traffic, holding pattern, selling event, and conversion — and shows exactly…

How to organize a graduate conference | Jonathan Courtney

Jonathan explores his experience organizing the graduate conference for his department (Ethics and Public Affairs, Carleton University). He outlines how he attempted to set a theme that would allow for effective altruism research topics, and what he would plan to do differently next time. Jon forme…

9 Huge Startup Opportunities in the AI Boom

I sit down with my friend Jonathan Courtney, a.k.a. Jicecream, to dig into the 9 biggest startup opportunities I see right now across B2C, AI, mobile, and IRL. We each pick ideas, trade reactions, and pressure-test them live. The conversation ranges from agent-first "action apps" to elder tech, thi…

Episode 59 - Fix Your Meetings with Lightning Decision Jams

In The Workshopper Playbook, author Jonathan Courtney presents a structured system designed to replace inefficient meetings with productive, high-impact collaboration. The core of his methodology is the 4C’s Framework, which guides teams through a four-stage process of Collecting data, Choosing pri…

My personal coaching session with Jonathan Courtney of AJ&Smart

This episode is a bit different. A little over a year ago, I listened to a podcast between Jonathan and Jason Fried, the co-founder of Basecamp/37signals. I had known Jonathan for a while, and I’m a big fan of Jason Fried, but the episode was very different — it was almost like a therapy session. J…

Life at the Speed of Play - Conclusion

We finished the book club today, y’all. After almost two months in Life at the Speed of Play by Mark Pincus, we landed on the conclusion — “How Ambitious Are You?” — and it’s a short chapter, but it hit different than the rest of the book. It’s more direct, less framework, more gut-check. So this o…

"I Spent 16 Years Building a Business That Isn't Right For Me." - Jonathan Courtney

Jonathan Courtney is the co-founder of AJ&Smart, the Berlin agency that helped make the Design Sprint famous and trained thousands of facilitators through Workshopper and facilitator.com.  In September 2026, after 16 years, he handed the company to his team and announced he was leaving to become a …

#116 - How to switch from consuming to creating

A companion piece to this week’s episode. The podcast is the full, unedited, and raw version; this is the organised part, edited and cleaned up with AI. You can listen to this episode on Spotify, and Apple Podcasts for audio only. Hey you. Finnally I get to talk about Big Magic! That, plus a YouTu…