I picked up reMarkable 2 to see how I liked typing on an eInk device. I share some initial impressions, but am facing a bigger, more interesting problem: how to I make it play nicely within my current writing ecosystem? Get all of the episodes at https://streamlinedsolopreneur.com/ Send feedback to https://streamlinedfeedback.com Is your tech stack helping you or just adding to the noise? Take my free tech stack assessment to see if your tools are actually worth it at https://streamlined.fm/tool...
Feb 05, 2026•6 min
What do Michelangelo, Shakespeare, Marie Curie, Ben Franklin, and Virginia Woolf all have in common? They all created long-lasting, humanity-impacting work…without the use of AI. See, there are lots of people who will tell you that you need to use AI or get left behind. Those people are wrong. In fact, I think the way to stand out is to not use AI. At least, not in the way everyone else is using it. While most people are using it to create for them…trying to get ChatGPT to “sound just like” them...
Feb 02, 2026•17 min•Season 2Ep. 515
It's the end of January and my Year of Digital Detox is in full swing. Here's how I'm doing with it so far. Read about The Year of Digital Detox: https://casabona.org/2026/01/2026-yearly-theme-digital-detox/ Subscribe to Paper & Smoke: https://paperandsmoke.com Submit feedback: https://streamlinedfeedback.com...
Jan 30, 2026•7 min
I was recently trying to do something that should have been simple: sharing my work calendar with my wife so she knows when I'm actually free for family time. I found myself digging through "secret" settings pages, checking her phone, then mine, and getting increasingly frustrated. It made me realize how often we settle for "fighting" our tools instead of letting them support us. You’ve probably heard me say that gear doesn’t matter. If you’re a new podcaster trying to drop $2,000 before you’ve ...
Jan 26, 2026•21 min•Season 2Ep. 514
I’m deeply worried about humanity losing our critical thinking skills. We’ve seen it degrade in the social media era, and now we’re seeing people wholesale outsource it in the AI era. But what if we can actually enhance our critical thinking with AI? I’m too much of a skeptic to tackle this topic on my own, which is why I brought in Christian Ulstrup, who’s doing some truly interesting things in the AI space. We talk about how AI is changing the education space, how we work, and why we should lo...
Jan 19, 2026•43 min•Season 2Ep. 513
“What’s your exit strategy?” Someone actually asked me this when I was starting my business. I didn’t have one. I’m not in it for the exit. But the question went to something deeper: how are you going to make actual money? Because the problem is most solo business owners charge hourly. Or they need to hire to scale. OR they need to sell the business. But there’s a better way: Value-Based Pricing. And Jonathan Stark is here today to tell us about it. Want to see how you’re spending your time so y...
Jan 12, 2026•54 min•Season 2Ep. 512
I am no Luddite. I have three pieces of technology that monitor my health and wellness. I’ve come to rely on many devices. That is why I am doing a digital detox. This is Paper and Smoke. It’s a look at how real-world craft happens, through the lens of a technologist going through digital detox. In a society increasingly online (and outsourcing thinking to AI), Paper and Smoke celebrates the real, the tangible, and the analog. Learn more at https://paperandsmoke.com...
Jan 09, 2026•4 min
There comes a time in everyone’s life when they’ve consumed too much of something, and they find the very notion of consuming more sickening. This is the very basis for my yearly theme. 2025 was finally the year were I felt my overconsumption of technology was getting the best of me. So this year, my theme is digital detox. Read the full article here: https://casabona.org/2026/01/2026-yearly-theme-digital-detox/ Show Notes My 2026 Yearly Theme My 2025 Yearly Theme Yearly Theme Archive My Intervi...
Jan 05, 2026•29 min•Season 2Ep. 511
We're almost at the end of Christmas break and I decided to record a quick update on how it's going...plus test my new camera. Check out the (somewhat unflattering) video here: https://youtu.be/HvSTnzOP01g ———— Streamlined Solopreneur is the podcast for solopreneurs who want to automate their business and take time off worry-free. Each week, Joe Casabona shares practical systems, tools, and strategies to help you reclaim your time and run your business without sacrificing your the rest of your l...
Jan 01, 2026•4 min
It's one of my favorite episodes of the year: my Favorites of the year! I'll go through all of my favorite media and tech of the year, as well as some close runners up and honorable mentions. Links below! My Favorites of 2025 When is it Time to Switch Tools? Paper & Smoke Book: Fahrenheit 182 Runner-up: The Anxious Generation Honorable Mentions: Neverwhere , Tiny Experiments , Listening to the Law TV Show: Alex vs. A-Rod Podcast: The Rest is History Podcast Honorable Mentions: Central Air , ...
Dec 31, 2025•29 min
Knowing when to get help is so, so, so crucial to prevent burnout. Laura Brazan knew this, which is why she decided to hire me for coaching. During our few months together, I was able to save her a ton of time, help her create process automations, and consolidate her tech stack. She even said that she’s saving more than she paid me! In this interview, we look at where she was before she hired me, the changes we made, and what she’s able to do now with the extra time she has. Want to see how you ...
Dec 29, 2025•39 min•Season 2Ep. 510
I knew from a young age, I wanted to play the drums. I got my first small kit when I was five, and when my friends and I started a "band," heavy quotes, I played paint buckets. When I was 15 years old, I knew I needed a real kit. This is the story of how I got it, and how one man's incredible kindness had a profound effect on me. Show Notes Read the Story at Casabona.org Submit feedback at https://streamlinedfeedback.com ———— Streamlined Solopreneur is the podcast for solopreneurs who want to au...
Dec 25, 2025•7 min
I started my Christmas vacation the minute my kids got out of school. I can do that because I’ve built a business that doesn't chain me to my desk. But if I’m being honest, I don’t take those two weeks off just to bake cookies and watch movies—I use that downtime to make next year even better. When the house is quiet, I run a full self-assessment on my business to figure out how I can further improve my processes, workflows, and systems. Think of it like a required annual car inspection for your...
Dec 22, 2025•23 min•Season 2Ep. 509
It’s a soon-to-be classic Pick 2 episode, where I pick 2 apps or tools I’m using and tell you about them. I say soon to be classic because I’ve wanted to do this for a while, and I’m finally going through with it! This week, it’s 2 apps I’ve used before and stopped using, but I’m revisiting. They are: Bear Notes Blinkist Thanks to AppStories for the idea Want to get the tools, apps, and automations I use delivered to your inbox? Join my mailing list . Read to build your perfect site? Check out S...
Dec 15, 2025•14 min•Season 2Ep. 508
It’s no secret I’m a full-on AI skeptic. And while I still use it, I’m very, very worried about the long-term effects of overuse. I saw a number of stories over the summer that point to us losing our ability to connect with other people. We’ve decided that efficiency and productivity are more important than everything, including accuracy and trust. That we’ve decided to implicitly trust something made wholly by other people, some of whom don’t fully understand what their creation does. Here’s my...
Dec 08, 2025•21 min•Season 2Ep. 507
What if your business could support your life instead of consuming it? That’s exactly what Liz Wilcox has built — a $9/month membership that supports her family, her sister, and three other families … all while she takes summers off. In this conversation, Liz shares how she built a half-million-dollar lifestyle business that aligns with her values — without sacrificing her time, her sanity, or her kid’s beach days. We talk about launching imperfectly, setting clear expectations, and building a b...
Dec 01, 2025•54 min•Season 2Ep. 506
I’m reading Amy Coney Barrett’s book, Listening to the Law , and it struck me that instead of writing using AI, we should write more like the Supreme Court…at least if we care about our audience. ———— Streamlined Solopreneur is the podcast for solopreneurs who want to automate their business and take time off worry-free. Each week, Joe Casabona shares practical systems, tools, and strategies to help you reclaim your time and run your business without sacrificing your the rest of your life, or yo...
Nov 26, 2025•6 min
Every year, I put together a massive gift guide for small business owners — but this year, I wanted to do things differently. Instead of rattling off every gadget and tool I’ve ever tried, I’m sharing the handful of products that actually made my life easier in 2025. From sleep earbuds that help me get more rest (even with kids and a dog) to the smart home lights that let me skip climbing into bushes every December, these are the gifts that save time, reduce friction, and make running a solo bus...
Nov 24, 2025•20 min•Season 2Ep. 505
Well, we're in the holiday gauntlet now. I've gotten several emails from small, service-based business promoting Black Friday sales, and I'm not sure that's a very good approach. I share my experience with successful, and less successful BF/CM deals I've run. I also talk about my approach to affiliates, and what I'm thinking about for that strategy in 2026. Check out the 3 tools I'm actually promoting for Cyber Week: https://streamlinedsolopreneur.com/3-black-friday-deals-on-tools-i-cant-live-wi...
Nov 21, 2025•8 min
My oldest daughter loves asking me to tell her a funny story about my wife from when we were dating... and I almost always freeze. It's not because there aren't any funny stories. It's because there are too many to pick from. This is exactly what happens when you open Zapier without a plan. You're faced with a "blank canvas" and endless possibilities, so you freeze and do nothing. You've heard about "triggers" and "actions," but you're not sure what your triggers or actions should be. Zapier isn...
Nov 17, 2025•12 min•Season 2Ep. 504
Our inboxes are about to be inundated with sales emails and affiliate-link riddled round-ups. Should I contribute to the noise? I'm thinking yes...but I want it to feel different. What do you think? Let me know at https://streamlinedfeedback.com ———— Streamlined Solopreneur is the podcast for solopreneurs who want to automate their business and take time off worry-free. Each week, Joe Casabona shares practical systems, tools, and strategies to help you reclaim your time and run your business wit...
Nov 15, 2025•3 min
Remember diagramming sentences back in school? I always thought it was pointless, but the real goal wasn't the diagram itself—it was understanding the structure of a good sentence. The same exact logic applies to building automations. It's tempting to just jump into a tool like Zapier or Make and start connecting things, but that's like throwing a bunch of random words on a page and hoping it makes sense. If you want to build automations that actually save you time (and don't break), you need to...
Nov 10, 2025•19 min•Season 2Ep. 503
Ever wonder if your newsletter should be the product…or just promote the product? I’ve been treating mine more like a magazine than a sales tool — and it’s cost me. So I sat down with Dylan Bridger, who helps course creators and coaches turn their newsletters into profit machines. We talk about: The difference between a “magazine” newsletter and a “sales team” newsletter How to actually warm up your audience so they buy when you make an offer But we also get into the impact becoming a new dad ha...
Nov 03, 2025•47 min•Season 2Ep. 502
When I was a kid, I said things like, “I won’t forget,” or “When I’m a dad, I won’t get mad.” Or…”I’m bored.” But as you get older, and life puts you in various, unforeseen situations, it’s easy to get blindsided and react in a way you hoped you wouldn’t. I think about this a lot when I consider what’s changed between turn 20 and turn 40. And there’s a common theme that has cropped up: pruning. Letting go of what doesn’t work. Of where you used to spend your energy. About making more space in yo...
Oct 27, 2025•49 min•Season 2Ep. 501
Episode 500 of the show came out on Monday. Here’s I I put it together using Google NotebookLM ———— Streamlined Solopreneur is the podcast for solopreneurs who want to automate their business and take time off worry-free. Each week, Joe Casabona shares practical systems, tools, and strategies to help you reclaim your time and run your business without sacrificing your the rest of your life, or your health. Start with the free Solopreneur Sweep — a step-by-step method for finding where your busin...
Oct 24, 2025•9 min
Nine years. 500 episodes. And one big question I've asked since the beginning. Do you have any trade secrets for us? When I started this show (back when it was How I Built It ), I was a newly married web developer with a side hustle and a curiosity for how others built their businesses. Ten years and three kids later, I’ve realized the mission has always been the same — helping solopreneurs build a business that supports their life, not consumes it. In this special milestone episode, I’m sharing...
Oct 20, 2025•27 min•Season 2Ep. 500
Am I overthinking how to approach episode 500? Plus, I got an android phone. Send feedback to https://streamlined feedback.com ———— Streamlined Solopreneur is the podcast for solopreneurs who want to automate their business and take time off worry-free. Each week, Joe Casabona shares practical systems, tools, and strategies to help you reclaim your time and run your business without sacrificing your the rest of your life, or your health. Start with the free Solopreneur Sweep — a step-by-step met...
Oct 16, 2025•6 min
We turned productivity into a fantasy draft! 🏆 Four small business owners battle it out, picking the apps and tools we cannot live without — with some surprise steals, hot takes, and even a bonus round for our favorite analog gear. Looking for new ways to save time, systemize your business, and actually enjoy the tools you use? This draft is packed with ideas you’ll want to steal. Draft Order: Mike Schmitz Layla Pomper Cat Mulvihill Joe Casabona Wondering how you can manage your time to find th...
Oct 13, 2025•52 min•Season 2Ep. 499
I just wrapped up a Social Growth for my friend Chenell’s community where I posted on LinkedIn for 40 days. Here’s what I learned and what’s next. Send your feedback at https://streamlinedfeedback.com ———— Streamlined Solopreneur is the podcast for solopreneurs who want to automate their business and take time off worry-free. Each week, Joe Casabona shares practical systems, tools, and strategies to help you reclaim your time and run your business without sacrificing your the rest of your life, ...
Oct 11, 2025•12 min
Can you really delegate out when you are your business ? Don’t people hire you to work with…well, you? That’s the question Justin Moore and I wrestle with. We talk about the challenge of running personality-driven businesses, why it’s so hard to step away, and how to build a company that serves your life instead of consuming it. Justin shares how he’s built a coaching business with a team he trusts, why impact is his North Star, and the mindset shift that helped him let go of control. We also ge...
Oct 06, 2025•29 min•Season 2Ep. 498
