Streamlined Solopreneur: Helping Solopreneurs Take a Guilt-Free Vacation Podcast By Joe Casabona Business Systems Coach cover art

Streamlined Solopreneur: Helping Solopreneurs Take a Guilt-Free Vacation

Streamlined Solopreneur: Helping Solopreneurs Take a Guilt-Free Vacation

By: Joe Casabona Business Systems Coach
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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.© 2016 - 2025 Joe Casabona Economics Leadership Management & Leadership
Episodes
  • Stop Selling Content: The Shift Toward Transformational Communities
    Feb 9 2026

    Memberships and Communities are a great way to stop selling hours for dollars. But you need to do it right.

    I recently sat down with my good friend Becky Pierson Davidson to talk about why so many communities fail and how she helps solopreneurs turn "ghost town" memberships into thriving, seven-figure assets It hinges on this: people don’t want a library of 150 hours of video; they want to solve a problem.

    If you’ve ever felt like your membership is a "traffic circle with no signs," this conversation is the GPS you need to create a clear member journey and build a business that supports your life instead of consuming it.

    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/

    Links

    • Becky Pierson Davidson
    • Build with Becky
    • How to be a Scrappy Researcher (to Actually Sell Products) with Becky Pierson Davidson

    What do you think? Send your feedback to streamlinedfeedback.com


    Simplify your tech stack at https://streamlined.fm/tools

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    45 mins
  • Working on Interoperability with the reMarkable 2 [Audio Note]
    Feb 5 2026

    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/tools


    Simplify your tech stack at https://streamlined.fm/tools

    ★ Support this podcast ★
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    7 mins
  • What do we lose by relying on AI too much?
    Feb 2 2026

    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 ★
    Show more Show less
    18 mins
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