Automate Without Losing Critical Thinking (My AI Philosophy)
Lately, I've been hearing horror stories about how people use AI. Not "AI wrote me a program" stories — I mean people who can't decide what...
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How I Built It
A podcast about building things on the web
How I Built It Podcast Guide
Listen to How I Built It, a Technology podcast by Joe Casabona. Stream 572 episodes in English, follow new audio stories, and play episodes online on Radio and Podcast.
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Is speaking worth my time, Zuck doesn't get people, HotD [Friday Wrap-Up]
This week I talk about why this is my heaviest speaking year since before the pandemic — and how I'm deciding whether all that travel and pr...
You Can't Automate What You Can't Explain
Register for my free workshop with Ecamm: https://ecamm.com/joe Here's the problem: most solopreneurs don't know exactly what they do. They...
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 rig...
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...
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 ab...
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....
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 int...
"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...
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...
Inbox Zero for Solopreneurs: The Exact System I've Used for 8 Years
Have you ever seen a 5-digit notification badge? It’s most stressful things I see on someone's phone. And I get it — as a solopreneur, email...
Do LLMs employ variable rewards, Spike Lee's hat, and a chilling video [Friday Wrap-Up]
Welcome to the Friday Wrap-Up for May 15, 2026. This is a short newsletter where I talk about 3 things: What’s on my mind this week, Recomme...
The Right Newsletter Tool Makes All the Difference: Why Solopreneurs Should Use Kit
Does having a mailing list feel like too much for you? Like it’s adding “one more thing” to your list as a one-person business? That's what...
Don't Miss Out on What You're Doing, Deleting Second Brains, drop dead [Friday Wrap-Up]
Are you so concerned with FOMO that you're Missing Out On What's There, rendering your real life MOOWT? That's what's on my mind today. Plus...
Why Your Solopreneur Business Feels Overwhelming (Fix This First)
The most overwhelming room in my house is the sunroom. Three small kids, all their toys, total chaos. One day, I was sitting in there feelin...
What Solopreneurs Can Learn From Star Wars
I have a confession to make: The first Star Wars movie I ever saw was Episode 1: The Phantom Menace . I was 13, and it just hit the dollar t...
Single-Purpose Apps, AI Won't Take Your Job, Ted Lasso is Back [Friday Wrap-Up]
Are single-purpose apps going to replace SaaS? I've been building small, focused tools with AI to replace subscriptions that solve my proble...
The One Thing Solopreneurs Shouldn't Automate (And What to Automate Instead)
Using AI to write your book is like using a car to run your marathon. Sure, you covered the distance — but nobody's impressed. Here's what I...
Trading Algorithms + Claude MYTHos [Friday Wrap-Up]
This week I've been deep in my SEO and content strategy, and it got me thinking: am I just trading one algorithm for another? I left social...
The Solopreneur's Guide to Discipline: Systems, Time, and Delegation
What if the best business advice you ever got came from a book about ancient philosophy? I've been on a bit of a reading bender this year —...