#37 | Let's Be Honest [blogcast]

#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

#40 | Winning and The Wave [blogcast]

At the 2003 U.S. Open, on center court, Pete Sampras emerged wearing a dark suit, open collar, surrounded by legends. He is retiring, and before he says a word, he’s overcome. He can’t get through it. Then Agassi appears on the screen—prerecorded, because he's still playing. "If I'd beaten Pete more often, or if he'd come along in a different generation, I'd have a better record. But I'd be less." Less. Most people confuse winning and competition. Grandpa cheats at Scrabble and calls himself competitive. He's not. He just likes to win. There's a difference, and it matters more than you think. This week's piece is about waves, rivals, and why the thing across the net might be making you who you are. Blog Post: Winning and The Wave [https://winwithflynn.com/2026/06/08/winning-the-wave/] Sponsors: TempRx⁠⁠⁠ [https://temprx.app/], ⁠⁠⁠31 Easy™ [https://winwithflynn.com/31easy/] Chapters: 00:00 - Redefining Winning: Beyond the Scoreboard 03:59 - Rivals as Waves: Pushing Your Limits 09:11 - Agassi's Realization: Why He Needed Pete 12:33 - Why We Often Cut Kedge Anchors Instead of Addressing the Real Issues

#39 | Anchors Aweigh! [blogcast]

You've heard a guy at a barbecue call his wife "the old ball and chain." It's a joke. It's also a lie. The real ball and chain travels with you everywhere you go. And most people spend their whole lives hacking at the wrong ones. This week's post is about two kinds of anchors — the ones that hold you in place, and the ones that pull you forward. The trick is telling them apart before you cut the wrong one loose. Blog Post: ⁠ [https://winwithflynn.com/2026/05/25/i-know/]Anchors Aweigh! [https://winwithflynn.com/2026/06/01/anchors-aweigh/] Sponsors: ⁠⁠TempRx⁠⁠ [https://temprx.app/], ⁠⁠31 Easy™ [https://winwithflynn.com/31easy/] Chapters: 00:00 - Unpacking the 'Ball and Chain' and Real Anchors in Life 03:54 - Understanding Anchors: Holding You Back or Pulling You Forward? 05:49 - Recognizing and Releasing the Deep-Rooted Anchors That Hold You Back 8:50 - Why We Often Cut Kedge Anchors Instead of Addressing the Real Issues 11:54 - How Perceived Burdens Can Actually Be the Anchors That Pull You Forward 15:42 - Embracing the Anchors That Propel You and the Power of Self-Doubt