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 prep time is actually worth it, given the real cost of crafting talks and getting clients from them. Then a story about Mark Zuckerberg telling Meta employees to "have fun again" after brutal layoffs, including the absurd perk of a permanent desk. And a recommendation for House of the Dragon Season 3, which drops June 21st. Links: My /now page Mark Zuckerberg ...
Jun 19, 2026•17 min
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 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. ...
Jun 16, 2026•25 min•Season 2Ep. 534
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 Intelligenc...
Jun 12, 2026•17 min
Register for my free workshop with Ecamm: https://ecamm.com/joe 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 ...
Jun 09, 2026•18 min•Season 2Ep. 533
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 Y...
Jun 05, 2026•16 min
Register for my free workshop with Ecamm: https://ecamm.com/joe 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 ...
Jun 02, 2026•19 min•Season 2Ep. 532
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 thi...
May 29, 2026•14 min
Register for my free workshop with Ecamm: https://ecamm.com/joe 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 th...
May 26, 2026•13 min•Season 2Ep. 531
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 ...
May 22, 2026•9 min
Register for my free workshop with Ecamm: https://ecamm.com/joe 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 you miss a deal? But after nearly a decade of refining my approach, I've built a technical system that keeps my inbox at (or close to) zero — without having to check it constantly. In this episode, I walk through the full setup: how SaneBo...
May 19, 2026•17 min•Season 2Ep. 530
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 mind... Earlier this week I found myself fighting Claude on something I felt was a pretty basic problem — one that I had used it to solve before. I kept going back and forth with Claude. I would ask it questions. It would then do things I didn't even remotely ask it to do. I started to form a weird the...
May 15, 2026•13 min
Register for my free workshop with Ecamm: https://ecamm.com/joe 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 don't have a newsletter because it feels like too much work, or they have one, but they're paying for a plan they don't actually need. And in almost every case, it's not a strategy problem. It's a tool problem. That's why I'm making the ca...
May 12, 2026•12 min•Season 2Ep. 529
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 you're storing every little thing in your second brain, and a fantastic performance from SNL. Finally, a pay small tribute Yankees legend, John Sterling, who passed away earlier this week. Get the newsletter version at https://streamlinedsolopreneur.com/wrap Show Notes I Deleted My Second Brain by Joa...
May 08, 2026•15 min
Register for my free workshop with Ecamm: https://ecamm.com/joe 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 minutes to clean it up. So we did — and suddenly it was a great place to hang out again. A lot of solopreneur businesses are like that sunroom. They're not broken. They don't need a massive overhaul. They need a quick sweep — a reset of your...
May 05, 2026•21 min•Season 2Ep. 528
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 realized I had never seen the Original Trilogy when I was surprised that Qui-Gon Jinn died (spoiler, I guess). We fixed that quickly, but this movie, despite being considered the worst Star Wars movie of all time (maybe bottom 2 now), started my love of the franchise. So I thought, in honor of May the F...
May 04, 2026•17 min
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 well-researched piece on why AI isn't actually coming for your job, and some very good news for Ted Lasso fans. On My Mind: Single purpose apps/the age of personalized software. Recommended Reading: The task is not the job Recommended Media : Ted Lasso Season 4 Trailer Want to get these wrap-ups del...
May 01, 2026•13 min
Register for my free workshop with Ecamm: https://ecamm.com/joe 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 handing off their most important work to AI without thinking about what that signals. When you let a language model write your first draft, come up with your ideas, or do your thinking for you, you're telling your audience that a lesser...
Apr 28, 2026•15 min•Season 2Ep. 527
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 Google, YouTube, and even AI search. Here's where I landed. Also: Cal Newport's take on Claude Mythos (spoiler: no, it's not terrifying), Ryan Holiday's Discipline is Destiny and what it has to say to solopreneurs, and a behind-the-scenes Architectural Digest video about the Scrubs revival that made me ...
Apr 24, 2026•17 min
Register for my free workshop with Ecamm: https://ecamm.com/joe 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 age of notifications and hustle culture. And when I picked up Ryan Holiday's Discipline Is Destiny , I wasn't expecting it to hit so close to home as a solopreneur. But it did. Here are 3 lessons I took away from the book — specifically t...
Apr 21, 2026•15 min•Season 2Ep. 526
Register for my free workshop with Ecamm: https://ecamm.com/joe 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 can catch it early, plus how bad sleep and brain fog made it worse. I've also got recommended reading from Mike Schmitz on using Claude to script YouTube videos (not my approach, but a thoughtful one), and a More Perfect Union video that ...
Apr 17, 2026•17 min
Register for my free workshop with Ecamm: https://ecamm.com/joe 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 not be all it’s cracked up to be. It can definitely be a huge timesaver (I've used it to build WordPress plugins and write Obsidian Dataview code), but it can also be a huge time suck. It can be hard to know if it’s worth trying. That’s w...
Apr 13, 2026•21 min•Season 2Ep. 525
Register for my free workshop with Ecamm: https://ecamm.com/joe 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 you think about your solopreneur systems, and how to work better so you can take more time off! Here's the Wrap-Up for April 10, 2026. On my mind Using AI to do all of the writing for you. Using Claude MAX Recommended Reading Rethinking ...
Apr 10, 2026•13 min
Register for my free workshop with Ecamm: https://ecamm.com/joe I can’t imagine something more overwhelming than sitting down on Monday and having no idea what to work on, despite knowing you have a bunch of work to do. But that’s how many solopreneurs start their week. Even worse, when you don’t know what to do, it’s easier for other people to hijack your time, you waste time by deciding in the moment, and it’s hard to measure success. I’ve spent years refining a system that takes just 20 to 25...
Apr 06, 2026•14 min•Season 2Ep. 524
Register for my free workshop with Ecamm: https://ecamm.com/joe Most task managers only tell you half the story. They show you what you checked off, but they have no idea that you moved that one task four days in a row, or that you cleared three things on Tuesday because you felt guilty, not because they were actually done. I've used pretty much every task manager out there; Todoist is my favorite and I still use it every day. But a while back I realized it couldn't tell me how I was actually wo...
Mar 30, 2026•13 min•Season 2Ep. 523
Register for my free workshop with Ecamm: https://ecamm.com/joe I loved watching the Olympics this year — more than usual. Part of it was the great stories and incredible performances. But a big part of it was that it was a celebration of human accomplishment. I believe firmly that AI can’t replace the actual good, worthwhile work we do…and the Olympics is a shining example of that. So for this episode, I wanted to share 3 lessons I think every solopreneur should learn from the Olympics. You nee...
Mar 23, 2026•17 min•Season 2Ep. 522
Register for my free workshop with Ecamm: https://ecamm.com/joe In 1998, I got genuinely frustrated with my mom for not knowing how to right-click. I thought technology was just… obvious. It took me an embarrassingly long time to realize it was only obvious to me because I'd grown up with it. Not everyone has that background — and assuming they should is how a lot of solopreneurs end up feeling like their tools are working against them. That's exactly what tech confidence coach Avital Spivak and...
Mar 16, 2026•34 min•Season 2Ep. 521
Register for my free workshop with Ecamm: https://ecamm.com/joe What will really happen if you don't respond to that email right away? I used to think "dedication" meant being reachable around the clock — skipping concerts, missing date nights, even taking a work call on Christmas Day. Then a pair of Hamilton tickets on my anniversary changed everything. My project manager told me I had to work through the weekend just to get paid on time. I said no, logged off, and came back Monday. Nothing fel...
Mar 09, 2026•14 min•Season 2Ep. 520
Register for my free workshop with Ecamm: https://ecamm.com/joe I had Strep Throat this week, and when I got sick of being cooped up in bed, I decided to do something interesting: use AI to code an iOS app. I have a lot of thoughts that probably require a part two to this note, but for now, I walk through the requirements, how the process was, and why this could be worth my time. Screenshots from the app Send feedback to https://streamlinedfeedback.com . Join my mailing list to get first dibs on...
Mar 06, 2026•14 min
Register for my free workshop with Ecamm: https://ecamm.com/joe Not all repetition is bad. Practicing a speech, drilling a recipe, building a training habit — that kind of repetition compounds over time. But there's another kind of repetition that doesn't build anything. It just eats your day, week after week, while your most important work sits untouched. I recently caught myself stuck in exactly that cycle. The kind where you're busy, you feel productive, but nothing is actually moving forward...
Mar 02, 2026•16 min•Season 2Ep. 519
Register for my free workshop with Ecamm: https://ecamm.com/joe I bought a modern iPod — not because I needed one, but because I realized I didn’t actually own most of the music I thought I did. It began with my daughter’s intense love of music. I’m committed to keeping smartphones out of my kids’ lives until they’re teens, and that meant finding a way for her to enjoy music without an internet-connected device Read more over at https://paperandsmoke.com ———— Streamlined Solopreneur is the podca...
Feb 25, 2026•12 min
