Is Claude Winning? [Friday Wrap-Up]
This week I talk about whether Claude is quietly winning the AI war — at least among business owners and tech nerds — after every speaker at Ecamm Creator Camp reached for Claude and nobody mentioned ChatGPT or Gemini, and why its "constitutional" rule-following makes me more comfortable using it. Then my take on finishing The Odyssey (the Emily Wilson translation) on a plane into Chicago, and a look at my Five-CD Changer Playlist — the five-albums-only, no-shuffle rules that make it fun. Links: …
Getting Distracted, Disney, and LEGO [Friday Wrap-Up]
This week I talk about almost re-joining a platform I know I'd hate. Then a look at Disney's next-gen audio-animatronic transforming from a pirate to a skeleton, and why it's a reminder that technology can still serve great storytelling. And a recommendation for the LEGO Game Boy set for a low-key long-weekend build. Plus, the Automation of the Week. Links: 2026 Summer and Fall Speaking Events I watched Disney's next-gen audio-animatronic transform from a pirate to a skeleton (TechRadar) LEGO Game…
I bought a tiny game controller for automation [Friday Wrap-Up]
This week I talk about my latest Mac automation tool: the 8BitDo Micro, a $15 tiny game controller I picked up during Prime Week and mapped to complex key combos and Raycast actions — and why these little tactile hardware automations are easier on your brain than memorizing keyboard shortcuts. Then a MacStories write-up that inspired the whole experiment, walking through real use cases for turning a game controller into a Mac input device. And a recommendation for New Rockstars' House of the Dragon…
You Can't Automate What You Can't Explain
Here's the problem: most solopreneurs don't know exactly what they do. They can't explain it, so they can't build systems around it. And when we try to build systems without explaining them, they end up with bad, ineffective systems. Because when we explain, we scrutinize. How do you fix it? Pick one task you do often, fire up a screen recorder, and narrate how you do it and why. Recording yourself doing your task is the blueprint. It is the plan. That's the first step to understanding the systems you…
Siri's big update, and a CRAZY LEGO scandal [Friday Wrap-Up]
This week I talk about WWDC and the big Siri update Apple just announced and why Apple's measured, context-aware approach feels like the right application of AI. Then the wild, still-unfolding Reckless Ben vs. Bricks and Minifigs saga, where a consigned Star Wars LEGO collection turned into a legal nightmare, and a recommendation for my own Alphabet Playlist: one album from one band for every letter of the alphabet, on Apple Music and Spotify. Links: Siri, AI, and the Latest in Apple Intelligence:…
AI for Solopreneur Systems: Two Projects That Actually Worked
I talk a lot about the wrong ways to use AI. But a rainy weekend gave me a few free hours and two pet projects that I used Claude Cowork for— and the results actually impressed me. The first: I used Claude to vibe-code a custom Obsidian theme from scratch. No CSS, no digging through the inspector — just a few prompts and some back-and-forth until it looked exactly the way I wanted. The second: a Claude skill that plans trips for me end-to-end — packing list, budget, Todoist project, calendar…
Why Summarize Everything, Ben Sasse, and Lou Gehrig [Friday Wrap-Up]
This week I talk about why summarizing everything isn't actually reading more — summaries rob you of the experience, the context, and the ability to form your own opinion, and I'd rather read one primary source than 14 summaries I'll forget. Then a heavy but admirable piece from The Dispatch on Ben Sasse facing terminal cancer with poise, and what it teaches us about being present with our families, and a recommendation for Lou Gehrig's Luckiest Man speech on YouTube. Links: Don't Let AI Steal Your…
The Automated Routine That Lets Me Leave Work at Work
I left work early recently to volunteer at my daughter's ice cream social and sit through her spring concert without checking my phone once. And if you’re a solopreneur, you know that’s a big deal. It’s all thanks to my startup and shutdown routines. And I know I’ve talked about them on the show before, but something interesting has happened over the last year. As LLMs and AI tools have been able to connect to more services through MCP, I’ve been doing my shutdown routine differently. It’s…
Saturday Mornings, The Creative Act, and Pop Punk [Friday Wrap-Up]
This week I talk about my surprisingly productive Saturday mornings — and why I'm hoping that same quiet, distraction-free focus carries into summer with all three kids out of school. Then The Creative Act by Rick Rubin, which pulled me out of a months-long reading slump in just a few days, and a recommendation for my early-to-mid 2000s pop punk discography playlists on Apple Music. Links: We're trying to summer camp again (Ep. 479) The Creative Act Joe Casabona on Apple Music If you enjoyed this,…
"I'll Remember It" Is a Lie: 3 Ways Solopreneurs Can Capture Tasks Faster
Have you ever gone to the grocery store without a list? You walk down every aisle, grab whatever looks good, spend way more than you planned — and somehow still get home without the one thing you actually needed. Running a one-person business without a real task capture system feels exactly the same. When everything falls on you, important work slips through the cracks. And without a plan, it's easy to spend your day on something that feels productive instead of something that actually moves the…
Do you work while driving? [Friday Wrap-Up]
This week I talk about how I used 4 hours of solo driving to and from a mastermind retreat in Baltimore — and why I chose to turn everything off instead of grinding through business prep. Then a wholesome story about a teen umpire who handled a coach's meltdown with poise, and a recommendation for SNL's The Rundown series on YouTube. Links: Solopreneurs and forced downtime A teen umpire tossed a baseball coach in a now-viral video. Here's his side of the story (The Athletic) SNL: The Rundown If…