Streamlined Solopreneur: Helping Solopreneurs Take Worry-Free Time Off

Joe Casabona, Business Systems Coach
  • 4.1 (101)
  • TECHNOLOGY

You started your business for freedom, not to be chained to your desk. I help solopreneurs build better systems they trust, so the can take time off without worrying. On Streamlined Solopreneur you'll get real-world strategies, smarter workflows, and practical tools to help you reclaim your time and actually enjoy the freedom you set out to create. Your host, Joe Casabona, is a seasoned technologist with over 25 years of experience. He's seen how the right systems can transform a business. But more than that, He's a teacher at heart. His goal isn’t to overwhelm you with jargon, but to make complex ideas simple and give you an actionable plan you can actually use. Because your business should support your life—not take it over. Tune in every Monday, wherever you get your podcasts.

  1. What do we lose by relying on AI too much?

    FEB 2

    What do we lose by relying on AI too much?

    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, I think you what you really need to do is create time and space to do good work. AI can help you do that. I talk about how in this episode. Looking to create even more time and space? Check out my free tools audit so you can make sure the apps and gear you use to run your business are actually helping you, not hurting you: https://streamlinedsolopreneur.com/tools/ What do you think? Leave feedback at https://streamlinedfeedback.com And finally, if you need Girl Scout Cookies and haven’t had someone come to your door, check out the video Teresa made for you at https://teresacasabona.com Simplify your tech stack at  https://streamlined.fm/tools ★ Support this podcast ★

    18 min
  2. January Accountability Report for Digital Detox [Audio Note]

    JAN 30 · BONUS

    January Accountability Report for Digital Detox [Audio Note]

    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.comSubmit feedback: https://streamlinedfeedback.com ★ Support this podcast ★

    7 min
  3. Why Gear and Tools Actually Matters

    JAN 26

    Why Gear and Tools Actually Matters

    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 hit "record," I stand by that. But when it comes to the daily operations of your business, the right gear—both hardware and software—matters immensely. Every minute you spend wrestling with a slow laptop, a glitchy hosting provider, or a manual process is a minute taken away from your family or your core mission. In this episode, I’m breaking down the "Gear" pillar of my GAPS framework. I'll share the specific tools that save me hours every week and give you a practical framework to audit your own toolbox. It’s time to stop letting bad systems eat your time so you can finally focus on your important work. Stop guessing which tools you need and start streamlining. Download my free Tools Audit at streamlined.fm/tools Show Notes When is it Time to Switch Tools?TodoistMy Stream DeckRodeCaster Pro 2Ecamm LiveTella.tvHave a question or a favorite tool? Share it with me at streamlinedfeedback.com. Simplify your tech stack at  https://streamlined.fm/tools ★ Support this podcast ★

    22 min
  4. How AI Can Actually Help Your Critical Thinking, not Hurt It

    JAN 19

    How AI Can Actually Help Your Critical Thinking, not Hurt It

    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 look to classic philosophers, like Aristotle, for the answers to how we should approach AI. The Walk and Talk Framework Want a great way to use AI? Use Christian’s Walk and Talk Framework:  Gather Your "Digital Exhaust": First, collect the raw data you've already produced. The AI Prompt: Copy and paste your text into a large-context model (like Google AI Studio) and use this specific prompt:"I want you to pose to me three extremely precise, very hard-hitting questions, all of which are independent and have different coverage, that if sufficiently answered, would yield some kind of transformative, genuinely novel, impactful insight. Please make reference to the primary source material where appropriate in the context of the question."The "Thinking" PhaseDon't look at the questions yet.Copy them into a mobile notes app and go for a wayRead only the first question. Open a Voice Memo and monologue your answer. Don't worry about being polished—mumble, ask yourself follow-up questions, and grapple with the idea until you feel you've reached a breakthrough. Repeat for the remaining questions. Distill the InsightLinks Christian Ulstrup on LinkedInThe First Draft is Where the Magic HappensHow Much is AI Harming Our Ability to Connect?Deep Questions Ep. 380: ChatGPT is Not AliveAristotle's Four CausesGSD at WorkRadiant Meeting RecorderGoogle AI StudioMailmeteor What do you think? Send your feedback to streamlinedfeedback.com Simplify your tech stack at  https://streamlined.fm/tools ★ Support this podcast ★

    44 min
  5. How to Serve More People and Scale Your Income

    JAN 12

    How to Serve More People and Scale Your Income

    “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 you can do more value-based pricing? Download my solopreneur self-assessment: https://streamlined.fm/impact  Links Jonathan StarkValue Pricing BootcampHourly Billing is Nuts What do you think? Send your feedback to streamlinedfeedback.com Simplify your tech stack at  https://streamlined.fm/tools ★ Support this podcast ★

    55 min
  6. New Podcast: Paper & Smoke [Trailer Drop]

    JAN 9 · BONUS

    New Podcast: Paper & Smoke [Trailer Drop]

    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 ★ Support this podcast ★

    4 min
  7. The Year of Digital Detox (2026 Yearly Theme)

    JAN 5

    The Year of Digital Detox (2026 Yearly Theme)

    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 ThemeMy 2025 Yearly ThemeYearly Theme ArchiveMy Interview with Amanda Goetz (It was 496, not 498!)My Favorites of 2025Paper & SmokeMy AI ManifestoLeave feedback at https://streamlinedfeedback.com/ Chapters 00:00 Introduction03:30 Grading The Year of Being Present11:27 What I Learned from The Year of Being Present14:57 My 2026 Yearly Theme17:06 Goal 1: Using my Devices Less22:55 Goal 2: Live in the Analog World27:35 Wrapping Up (00:00) - Introduction (04:12) - Grading The Year of Being Present (12:09) - What I Learned from The Year of Being Present (15:39) - My 2026 Yearly Theme (17:48) - Goal 1: Using my Devices Less (23:37) - Goal 2: Live in the Analog World (28:17) - Wrapping Up Simplify your tech stack at  https://streamlined.fm/tools ★ Support this podcast ★

    30 min
  8. An End of the Year (Beginning of the Year?) Update

    JAN 1 · BONUS

    An End of the Year (Beginning of the Year?) Update

    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 Simplify your tech stack at  https://streamlined.fm/tools ★ Support this podcast ★

    4 min
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About

You started your business for freedom, not to be chained to your desk. I help solopreneurs build better systems they trust, so the can take time off without worrying. On Streamlined Solopreneur you'll get real-world strategies, smarter workflows, and practical tools to help you reclaim your time and actually enjoy the freedom you set out to create. Your host, Joe Casabona, is a seasoned technologist with over 25 years of experience. He's seen how the right systems can transform a business. But more than that, He's a teacher at heart. His goal isn’t to overwhelm you with jargon, but to make complex ideas simple and give you an actionable plan you can actually use. Because your business should support your life—not take it over. Tune in every Monday, wherever you get your podcasts.

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