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PODCAST

Streamlined Solopreneur: Automate Your Business, Take Time Off Worry-Free

Joe Casabona, Solopreneur Systems Coach

As a solopreneur, it can feel hard to take time off. I mean REALLY take time off. Not take a vacation where you still respond to email. The problem is that for many solopreneurs running a one-person business, taking time off means the business shuts down. As a result, you’re constantly worrying about it. But what if you had great systems in place to automate your business? That’s exactly what you’ll get with Streamlined Solopreneur. You’ll learn how to turn manual tasks into reliable systems, so

business entrepreneurship

All Episodes

14:59

The Solopreneur's Guide to Discipline: Systems, Time,...

Streamlined Solopreneur: Automate Your Business, Take... ·

2026/04/21

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 things solopreneurs need to hear.If you're not sure what you

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16:45

What is AI Brain + Recommendations [Friday Wrap-Up]

Streamlined Solopreneur: Automate Your Business, Take... ·

2026/04/17

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 exposes Polymarket's prediction markets for what they

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12:38

Thoughts and Recommendations for April 10, 2026...

Streamlined Solopreneur: Automate Your Business, Take... ·

2026/04/10

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 mindUsing AI to do all of the writing for you.Using Claude MAXRecommended ReadingRethinking RSS, newsletters, and how I read every morningThe 3 Question

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13:44

How to Plan Your Week as a Solopreneur (My Exact System)

Streamlined Solopreneur: Automate Your Business, Take... ·

2026/04/06

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 minutes every Sunday, but saves me hours of "buffer time"

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13:45

How to Understand How You Work with a Task Journal

Streamlined Solopreneur: Automate Your Business, Take... ·

2026/03/30

My absolute favorite task manager is Todoist. I’ve been around the block and used all the major ones — from Remember the Milk to OmniFocus and everything in between. Todoist is the best for me.But a task manager only tells part of the story — it tells us what we got done.It doesn’t tell us anything about how we were feeling that day. How many tasks did we move or ignore? How many have we checked off just so we’d stop seeing them?And it shouldn’t. That’s what task journaling is for.Here's

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35:01

How to Build a Better Relationship with Your Tools

Streamlined Solopreneur: Automate Your Business, Take... ·

2026/03/16

I remember getting annoyed at my mom in 1998 because she didn't understand how to "right-click." I just assumed technology was intuitive. But it was intuitive to me because I grew up with it. It’s not easy for everyone – a lesson I learned that day.Luckily, I took that lesson to heart and now I’m a much more patient teacher…much like today’s guest.In this episode, I’m joined by tech confidence coach Avital Spivak to talk about the mental hangups that keep solopreneurs from mastering their

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12:13

Why I'm Buying Music Again in 2026 [Paper & Smoke]

Streamlined Solopreneur: Automate Your Business, Take... ·

2026/02/25

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 deviceRead more over at https://paperandsmoke.comSimplify your tech stack at https://streamlined.fm/tools ★ Support this podcast ★

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15:13

Why I Love Talking to my Phone Now

Streamlined Solopreneur: Automate Your Business, Take... ·

2026/02/23

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

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22:41

How to take more time off

Streamlined Solopreneur: Automate Your Business, Take... ·

2026/02/16

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

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45:10

Your Members Don't Want More Content

Streamlined Solopreneur: Automate Your Business, Take... ·

2026/02/09

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

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54:54

How to Serve More People and Scale Your Income

Streamlined Solopreneur: Automate Your Business, Take... ·

2026/01/12

“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

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4:04

New Podcast: Paper & Smoke [Trailer Drop]

Streamlined Solopreneur: Automate Your Business, Take... ·

2026/01/09

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

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29:17

My Favorite Tech, Apps, and Media of 2025

Streamlined Solopreneur: Automate Your Business, Take... ·

2025/12/31

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 2025When is it Time to Switch Tools?Paper & SmokeBook: Fahrenheit 182Runner-up: The Anxious GenerationHonorable Mentions: Neverwhere, Tiny Experiments, Listening to the LawTV Show: Alex vs. A-RodPodcast: The Rest is HistoryPodcast Honorable Mentions: Central Air, How We

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39:21

How I Saved Laura Brazan More Than She Spent on my...

Streamlined Solopreneur: Automate Your Business, Take... ·

2025/12/29

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

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7:34

Replay: My Favorite Christmas Story

Streamlined Solopreneur: Automate Your Business, Take... ·

2025/12/25

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 NotesRead the Story at Casabona.orgSubmit feedback at https://streamlinedfeedback.comGet your free Time and Tools Self-Audit at

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52:16

How Liz Wilcox Built a Half-Million-Dollar Business...

Streamlined Solopreneur: Automate Your Business, Take... ·

2025/12/01

Save 30-50% on Learn Dash, GiveWP, The Events Calendar, and more: https://streamlined.fm/fridayWhat 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

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6:27

We should write less with AI and more like the...

Streamlined Solopreneur: Automate Your Business, Take... ·

2025/11/26

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. ★ Support this podcast ★

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18:50

The Best Gifts for Small Business Owners (2025 Edition)

Streamlined Solopreneur: Automate Your Business, Take... ·

2025/11/24

Save 30-50% on Learn Dash, GiveWP, The Events Calendar, and more: https://streamlined.fm/fridayEvery 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

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7:32

My Approach to Black Friday, and Affiliate Links

Streamlined Solopreneur: Automate Your Business, Take... ·

2025/11/21

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:

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11:23

The 3-Step Process for Your First Automation

Streamlined Solopreneur: Automate Your Business, Take... ·

2025/11/17

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

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