#38 | I Know, Right!?! [blogcast]

#45 | The Plus: Part 4, The Handoff [blogcast]

Your job is to keep diverging. The robots' job is to converge. The handoff between those two—the place where divergent input meets convergent execution—that's the prompt. This is Part 4 of The Plus, and it's the practical one. I'll walk you through how I actually build prompts—not the color-coded template you've seen circulating, but a method that gets reverse-engineered from real conversations. I'll show you the fitness prompt that runs my weekly training, the stocks prompt that grades every company in my portfolio, and we'll talk about the cover-art prompt that fails me every week. Plus a few rules that have held up across a dozen prompts: light beats heavy. Interview first. Constrain the output. Forbid the BS. And how a non-technical guy ended up shipping web apps overnight. Blog Post: The Plus: Part 4, The Handoff [https://winwithflynn.com/2026/07/13/the-handoff/] Sponsors: TempRx.App [https://temprx.app/] CanIRetire.App [https://caniretire.app/] FlowFinder [https://winwithflynn.com/flow-finder/] HelloRatio [www.helloratio.org] Chapters: 00:00 - Part 4: Speaking with Robots and Prompting 02:43 - The Handoff: Beyond Template-Based Prompting 04:26 - Crafting Your Personalized AI Fitness Consultant 06:17 - AI for Finance: Scoring Stocks and Valuations 09:19 - Mastering Prompts: Light, Interview, Constrain, Forbid 12:44 - The Human Element: Where AI Prompts Fail 15:04 - Building Apps with AI: The Handoff of Meaning 19:42 - Thank You for Listening: Share the Show

#44 | The Plus: Part 3, Keep Diverging [blogcast]

The nine-dot puzzle has been around for decades. Connect all nine with four straight lines…without lifting your pen. In the control group, nobody solves it. Then researchers temporarily suppress the rule-following part of the brain with electrical stimulation. Forty percent crack it. The puzzle didn't change. The rules didn't change. The frame did. This is Part 3 of The Plus. We get into convergent vs. divergent thinking, why LLMs can only do one of them, and what your kids can tell you about which one you're built for. Then we meet the train kid—the viral clip that explains how it feels to work with the robots. And last, three questions you can ask yourself to know if you're at risk of losing the "+." Blog Post: The Plus: Part 3, Keep Diverging [https://winwithflynn.com/2026/07/06/keep-diverging/] Sponsors: ⁠⁠Passing Notes to Strangers ⁠⁠ [https://winwithflynn.com/books/passing-notes-to-strangers-book/] ⁠⁠31 Easy™⁠⁠ [https://winwithflynn.com/31easy/] ⁠⁠TempRx [https://temprx.app/] Chapters: 00:00 - Unpacking "The Plus": A Roadmap for Part 3 02:06 - Beyond the Box: Humans, LLMs, and the 9-Dot Puzzle 07:10 - Are You Just Pushing the Train? AI's Hidden Impact 10:40 - Three Critical Questions to Keep Your "Plus" Alive 12:11 - Thank You for Listening: Stay Divergent, Stay Original

#43 | The Plus: Part 2, The Atrophy Problem [blogcast]

In April, the Artemis II splashed down after a ten day trip around the moon. Three of the four astronauts couldn't walk off the deck. Ten days. From able-bodied to not. Your brain works the same way. This is Part 2 of The Plus. We look at the atrophy problem—what happens when you let AI do the cognitive lift, and what an MIT study found when they wired up 54 essay writers with EEG headsets. We also cover the lost sense of direction, the muscle you actually need to train, and the single discipline that holds the rest together. The "+" weakens when humans stop carrying cognitive load. And there's a specific kind of load only humans can carry. Blog Post: The Plus: Part 2, The Atrophy Problem [https://winwithflynn.com/2026/06/29/the-atrophy-problem/] Sponsors: ⁠Passing Notes to Strangers ⁠ [https://winwithflynn.com/books/passing-notes-to-strangers-book/] ⁠31 Easy™⁠ [https://winwithflynn.com/31easy/] ⁠TempRx [https://temprx.app/] Chapters: 00:00 - How Convenience Leads to Physical and Cognitive Atrophy 05:29 - Reclaiming Skills: The Cost of Convenience and Practice 08:58 - The First Swipe Rule: Maintain Your Edge with AI

#42 | The Plus: Part 1, Working With the Robots [blogcast]

In late 2024, AI-generated articles passed human-written ones. Twelve months later, AI took the lead online. Then the volume plateaued. Not because the robots stopped writing. Because nobody was reading. This is Part 1 of The Plus, a five-part series on working with the robots. We start with the Super Mid Plateau—the strange ceiling AI content has hit and why writing is the medium where humans still matter most. The robots can copy a YouTube prank in their sleep. They can't copy a paragraph that took forty drafts. That asymmetry isn't shrinking. It's the whole game. Nicky Case said it best: the hard part isn't the AI, it isn't even the human, it's the "+". Welcome to the series. Blog Post: The Plus: Part 1, Working With the Robots [https://winwithflynn.com/2026/06/22/the-robots-are-here/] Sponsors: Passing Notes to Strangers [https://winwithflynn.com/books/passing-notes-to-strangers-book/] 31 Easy™ [https://winwithflynn.com/31easy/] TempRx [https://temprx.app/] Chapters: 00:00 - Dave Flynn on the Radio: Introducing the AI Series 02:04 - Human Plus AI: The Hard Part Isn't the AI 03:14 - Why AI-Generated Articles Hit a Strange Ceiling 04:30 - AI Training on Itself: The Habsburg Bloodline of Content 07:29 - The Asymmetry: Why Human Writing Still Matters 08:54 - The Robots Are Here: It's About Collaboration 09:39 - Thank You for Listening: Share and Review the Show

#41 | Is This Thing On? [blogcast]

In 1951, a comedian named Jack Roy walked away from the stage. Twelve years later he came back as someone else. And I think about Jack a lot lately A piece about writing into the void, what the kids are watching, and finding the difference between asking the room if it's working and telling them what's really going on. Blog Post: ⁠ [https://winwithflynn.com/2026/06/08/winning-the-wave/]Is This Thing On? [https://winwithflynn.com/2026/06/15/is-this-thing-on/] Sponsors: Passing Notes to Strangers [https://winwithflynn.com/books/passing-notes-to-strangers-book/] Chapters: 00:00 - Embracing The Belly of the Whale and Jack Roy's Early Struggles 02:32 - Comparing Success, Low Views, and Kids' Viral Expectations 06:38 - The Rodney Dangerfield Lesson and Podcast Wrap-Up