Streamlined Solopreneur: Helping Solopreneurs Take Time Off Worry-Free

Streamlined Solopreneur: Helping Solopreneurs Take Time Off Worry-Free

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You started your business for freedom, not to be chained to your desk. I help solopreneurs replace manual tasks with a reliable system so they can take time off worry-free. 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...
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Episode List

Why I Love Talking to my Phone Now

Feb 23rd, 2026 7:00 AM

I remember when Nextel first launched its "push-to-talk" walkie-talkie feature back in the late 90s. It mostly resulted in people yelling into their phones at the mall, and it honestly made me hate the idea of talking to my phone in public for decades. But things have changed.Between the rise of asynchronous communication and the power of AI transcription, I’ve found that talking to my phone is actually one of the best ways to stay productive while I’m away from my desk.In this episode, I’m breaking down why I’ve embraced talking to my phone. I’ll share the two specific apps that have simplified my workflow—Whisper Memos and Todoist’s Ramble feature—so I can capture context, brain dump my shutdown routines, and turn spoken ideas into actionable tasks without losing a single thought.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 streamlined.fm/tools.Show Notes**Whisper Memos:** The iOS app I use for high-quality transcription and custom summaries.**Todoist:** My go-to task manager, specifically using the new "Ramble" feature for voice-to-task entry.Video: Todoist Killed My Favorite Automation (and I'm Happy About It)Streamlined Feedback: Share how you use voice notes at streamlinedfeedback.comTech Stack Assessment: Get clarity on your tools at streamlined.fm/tools Simplify your tech stack at  https://streamlined.fm/tools ★ Support this podcast ★

Why I’m Returning the remarkable 2 [Audio Note]

Feb 18th, 2026 12:00 PM

I tested the reMarkable 2 with the Type Folio keyboard hoping for a distraction‑free, E‑ink writing experience. It’s a great device but I found it wasn't great for my workflow. Here’s why. Plus, a new experiment. Let me know your thoughts at https://streamlinedfeedback.com.  Visit https://streamlinedsolopreneur.com/ for more insights.  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 ★

How to take more time off

Feb 16th, 2026 7:00 AM

I was recently stuck in an airport for 6 hours while my flight got more and more delayed. But instead of being mad about it, I realized something: this was a blessing of forced downtime.And while I’m usually really good about taking time off, I know many solopreneurs who aren’t. We feel like we need to work or the business will crumble. I was there a few years ago.But the good news is it’s not true. You can take time off and still have a thriving business. And in today’s episode, I tell you how.Want to start creating more space in your business? 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 Simplify your tech stack at  https://streamlined.fm/tools ★ Support this podcast ★

Your Members Don't Want More Content

Feb 9th, 2026 7:00 AM

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/LinksBecky Pierson DavidsonBuild with BeckyHow to be a Scrappy Researcher (to Actually Sell Products) with Becky Pierson DavidsonWhat do you think? Send your feedback to streamlinedfeedback.com Simplify your tech stack at  https://streamlined.fm/tools ★ Support this podcast ★

Working on Interoperability with the reMarkable 2 [Audio Note]

Feb 5th, 2026 2:25 PM

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.comIs 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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