Streamlined Solopreneur: Helping Solopreneurs Automate to Take Time Off Worry-Free
Joe Casabona, Solopreneur Systems Coach
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19 recent episodes with transcripts
569 episodes for longitudinal research
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Recent Episodes
S2 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…
S2E533 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…
S2 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…
S2E532 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.…
S2 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…
S2E531 "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…
S2 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…
S2E530 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 feels urgent. What if a client needs something? What if…
S2 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, Recommended Reading, and Recommended Media. Here's what's on my…
S2E529 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 I hear constantly when I coach solopreneurs. Either they…
S2 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, a great article about why it might actually be bad that…
S2E528 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 feeling overstimulated and realized it would take about five…
S2 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 theater when my friend invited me to see it with him. He…
S2 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 problem, just not quite my way, and I'm not the only one. Also: a…
S2E527 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'm seeing with solopreneur automation right now: people are…
S2 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 media to stop chasing feeds, but now I'm optimizing for…
S2E526 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 — physical books, old ideas, things written long before the…
S2 What is AI Brain + Recommendations [Friday Wrap-Up]
AI brain is when you've come to rely on AI for even the most basic things -- and after a week deep in Claude Max, I felt it creep back in. I'm sharing the three warning signs I've identified so you…
S2E525 Vibe Coding for Solopreneurs: When It's Worth It and When It's Not
I understand the temptation of using AI to write your own apps. I’m sick of the endless subscriptions, feature bloat, and raising the subscription price to accommodate the feature bloat. But it may…
S2 Thoughts and Recommendations for April 10, 2026 [Friday Wrap-Up]
I'm trying a new format this week called the Friday Wrap-up, where I tell you what's on my mind, and recommend some articles and videos. The hope here is to curate some more timely resources to help…
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