Streamlined Solopreneur: Helping Solopreneurs Build Systems So They Can Take Time Off

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 ★

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.comAnd 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 ★

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 ★

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/toolsShow NotesWhen 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 ★

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 FrameworkWant 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 InsightLinksChristian 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 StudioMailmeteorWhat do you think? Send your feedback to streamlinedfeedback.com Simplify your tech stack at  https://streamlined.fm/tools ★ Support this podcast ★

“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 LinksJonathan StarkValue Pricing BootcampHourly Billing is NutsWhat do you think? Send your feedback to streamlinedfeedback.com Simplify your tech stack at  https://streamlined.fm/tools ★ Support this podcast ★

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 ★

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 NotesMy 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/ Chapters00:00 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 ★

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 ★

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 Made Your MotherMusic: SadMovie: Wicked: For GoodVideo Game: Hogwarts: LegacyApp: Tella.TVEcamm LiveBear Notes Simplify your tech stack at  https://streamlined.fm/tools ★ Support this podcast ★

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 you can improve your systems and prevent burnout? Try my self-assessment: https://streamlined.fm/impact LinksGrandparents Raising GrandchildrenPodlaunchPodmatchInterested in Coaching? Go here.What do you think? Send your feedback to streamlinedfeedback.com Read to build your perfect site? Check out StellarSites.Simplify your tech stack at  https://streamlined.fm/tools ★ Support this podcast ★

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

I started my Christmas vacation the minute my kids got out of school. I can do that because I’ve built a business that doesn't chain me to my desk. But if I’m being honest, I don’t take those two weeks off just to bake cookies and watch movies—I use that downtime to make next year even better.When the house is quiet, I run a full self-assessment on my business to figure out how I can further improve my processes, workflows, and systems. Think of it like a required annual car inspection for your business. You might uncover some unwanted "bills," but fixing small issues now prevents massive breakdowns later.In this solo episode, I'm walking you through the three crucial things I review before the new year: Tools, Workflows, and Systems. I’ll share how a tools assessment saved a client more than she paid me for coaching, the three use cases I have for my writing apps, and the single bottleneck I look for to make sure my team is running smoothly. This isn’t about adding more work; it’s about strategically refining what you already do to create more space and impact in the coming year.*Want to do this self-assessment? Get my template at https://streamlined.fm/impact*Submit feedback at https://streamlinedfeedback.com Read to build your perfect site? Check out StellarSites.Simplify your tech stack at  https://streamlined.fm/tools ★ Support this podcast ★

It’s a soon-to-be classic Pick 2 episode, where I pick 2 apps or tools I’m using and tell you about them. I say soon to be classic because I’ve wanted to do this for a while, and I’m finally going through with it!This week, it’s 2 apps I’ve used before and stopped using, but I’m revisiting. They are:Bear NotesBlinkistThanks to AppStories for the ideaWant to get the tools, apps, and automations I use delivered to your inbox? Join my mailing list. Read to build your perfect site? Check out StellarSites.Simplify your tech stack at  https://streamlined.fm/tools ★ Support this podcast ★

It’s no secret I’m a full-on AI skeptic. And while I still use it, I’m very, very worried about the long-term effects of overuse. I saw a number of stories over the summer that point to us losing our ability to connect with other people.We’ve decided that efficiency and productivity are more important than everything, including accuracy and trust. That we’ve decided to implicitly trust something made wholly by other people, some of whom don’t fully understand what their creation does.Here’s my approach to AI, how we can be better, and my hopes for 2026.And if you want to save time without giving up your humanity, check out my automations at https://streamlined.fm/quizShow NotesWe’re giving up too much to AIDon’t Rely on AI for Human Growth and HealingParents of teenager who took his own life sue OpenAIMeta’s AI rules let bots hold ‘sensual’ chats with childrenWe are rushing into the same mistakes we made with social mediaFaster Doesn’t Mean Better. Faster Means FasterThe AI Trap: Why Over-Reliance will Cost You Time (and Your Voice)The Urgency of InterpretabilityIt’s Been 2 Years Since ChatGPT Came Out. How do Solopreneurs Use It? Read to build your perfect site? Check out StellarSites.Simplify your tech stack at  https://streamlined.fm/tools ★ Support this podcast ★

What 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 kid’s beach days.We talk about launching imperfectly, setting clear expectations, and building a business that runs with your life, not against it. Liz’s energy and honesty are unmatched, and her story will change how you think about pricing, productivity, and purpose.Top TakeawaysA low-ticket offer can be high value — if you set clear expectations and deliver consistently.Don’t wait for perfect — Liz launched her $9 membership using Google Docs and built from there.Transparency builds trust. Tell your audience what you’re doing, why you’re doing it, and when they can expect it.Liz’s signature $9 membership is here: https://streamlinedsolopreneur.com/liz  — hit the hot pink button to grab her free email templates (and sneak a $1 trial of the membership).🎧 Listen on: streamlinedsolopreneur.comWhat do you think? Send your feedback to streamlinedfeedback.com Read to build your perfect site? Check out StellarSites.Simplify your tech stack at  https://streamlined.fm/tools ★ Support this podcast ★

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

Every 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 bushes every December, these are the gifts that save time, reduce friction, and make running a solo business just a little more fun.If you’re shopping for yourself or a small business owner in your life, you’ll find something here that genuinely improves work and home life — without adding clutter or complexity.Want to check out a written version of the gift guide? Head here: https://streamlinedsolopreneur.com/2025-gift-guide/Show NotesGift Guide for Small Business OwnersA Fantastic EpisodeKindle ColorsoftTRMNLSoundcore Sleep A20 EarbudsI Bought, and Returned, the Ozlo SleepbudsFull Review – Soundcore Sleep A20 EarbudsDJI Mic Mini (2 TX + 1 RX + Charging Case)Zoom PodTrak P4 Podcast RecorderBose SoundLink Max Bluetooth SpeakerPhilips Hue Indoor/Outdoor Holiday 130-Foot Festavia String LightsAqara Zigbee Motion Sensor P1Eve Aqua Smart Water ControllerGitryin 10-in-1 Desktop Charging StationAnker Nano Charging StationAnker 9-in-1 Charging StationHoverBar DuoSee HoverBar Duo SetupUGREEN NASync DXP4800 4-Bay Desktop NASPost-it Super Sticky Easel PadProfessional Grade Gaffer TapeKeeping Equipment in PlaceAnalog Card Bar by UgmonkCalDigit E5 – Thunderbolt 5 Element 5 HubTwelve South HiRise 3 DeluxeMotorola razrSanDisk 2TB Extreme Portable SSDBellroy Tech Kit (Tech Accessories Organizer Pouch)Tella.tvObsidianGling.aiGoodLinksMasterClassSenja Read to build your perfect site? Check out StellarSites.Simplify your tech stack at  https://streamlined.fm/tools ★ Support this podcast ★

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: https://streamlinedsolopreneur.com/3-black-friday-deals-on-tools-i-cant-live-without/ Here's my 2025 Gift Guide: https://streamlinedsolopreneur.com/2025-gift-guide/ Simplify your tech stack at  https://streamlined.fm/tools ★ Support this podcast ★

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 isn’t a sandbox for people starting out. The secret is to look at the work you're already doing.I'll walk you through my simple, three-step process to get started. It starts with documenting your tasks, listing your apps, and then using one specific (and often overlooked) page on Zapier's website that will show you exactly what's possible for you.Stop staring at the screen, wondering where to begin. Let's get your first automation built.Want to see some real-world examples tailored to your biggest struggles? Take my free quiz at https://streamlined.fm/quiz and I'll email you four automation ideas you can use today.Show NotesTake the Automation Quiz: streamlined.fm/quizExplore the Zapier Apps Page: zapier.com/appsWatch the Zapier Apps Page Walkthrough VideoLeave feedback: streamlinedfeedback.com Read to build your perfect site? Check out StellarSites.Simplify your tech stack at  https://streamlined.fm/tools ★ Support this podcast ★