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PODCAST

Streamlined Solopreneur: Helping Solopreneurs Take Time Off Worry-Free

Joe Casabona, Business Systems Coach

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 business

business entrepreneurship

All Episodes

22:41

How to take more time off

Streamlined Solopreneur: Helping Solopreneurs 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: Helping Solopreneurs 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: Helping Solopreneurs 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: Helping Solopreneurs 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: Helping Solopreneurs 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: Helping Solopreneurs 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: Helping Solopreneurs 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: Helping Solopreneurs 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: Helping Solopreneurs 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: Helping Solopreneurs 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: Helping Solopreneurs 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: Helping Solopreneurs 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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3:14

Thinking About Affiliate Emails During Cyber Week

Streamlined Solopreneur: Helping Solopreneurs Take... ·

2025/11/15

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 ★ Support this podcast ★

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18:38

The 4 Core Components of Every Automation

Streamlined Solopreneur: Helping Solopreneurs Take... ·

2025/11/10

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

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46:16

The #1 Mistake Solopreneurs Make With Newsletters

Streamlined Solopreneur: Helping Solopreneurs Take... ·

2025/11/03

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” newsletterHow to actually warm up your audience so they buy when you make an offerBut we also get into the impact becoming a new dad

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48:22

Growth by Subtraction: How to Make Time for What...

Streamlined Solopreneur: Helping Solopreneurs Take... ·

2025/10/27

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

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9:05

How I Built Episode 500

Streamlined Solopreneur: Helping Solopreneurs Take... ·

2025/10/24

Episode 500 of the show came out on Monday. Here’s I I put it together using Google NotebookLM★ Support this podcast ★

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5:52

Big milestone episode coming Monday!

Streamlined Solopreneur: Helping Solopreneurs Take... ·

2025/10/16

Am I overthinking how to approach episode 500? Plus, I got an android phone. Send feedback to https://streamlined feedback.com★ Support this podcast ★

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52:25

The Productivity Tools Draft

Streamlined Solopreneur: Helping Solopreneurs Take... ·

2025/10/13

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 SchmitzLayla PomperCat MulvihillJoe CasabonaWondering how you can manage your time to find the

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28:55

Stop Being the Bottleneck in Your Business

Streamlined Solopreneur: Helping Solopreneurs Take... ·

2025/10/06

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

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