The Feed

  • June 23, 2026

    Automate Without Losing Critical Thinking (My AI Philosophy)

    Register for my free workshop with Ecamm: https://ecamm.com/joe

    Lately, I’ve been hearing horror stories about how people use AI. Not “AI wrote me a program” stories — I mean people who can’t decide what to make for dinner, write their own feedback on a contractor’s work, or come up with a single question for a webinar without asking a chatbot first. I call it AI Brain Rot, and getting really bad.

    So I walk through the three warning signs you might be slipping into AI brain rot, my 5 Pillar AI Philosophy, and three rules to keep your brain sharp while you still automate your business. We get into where AI actually shines — crunching data, transcribing calls, processing your notes — and where it absolutely doesn’t.

    If you want to build solopreneur systems that rely on you in the right ways, this one’s for you.

    Want systems that will help you free up your time without killing your ability to think? Grab the Solopreneur Starter Kit — four systems to help you run your one-person business, with recommended tools and automations. Plus, it’s 100% written by me (not AI). It’s free at streamlined.fm/kit.

    Links

    • (00:00) – What is AI Brain Rot?
    • (04:11) – Warning Signs of AI Brain Rot
    • (13:10) – My 5-Pillar AI philosophy
    • (14:46) – Rules for preventing AI Brain Rot
    • (21:06) – Wrap-up

    ————
    Streamlined Solopreneur is the podcast for solopreneurs who want to automate their business and take time off worry-free. Each week, Joe Casabona shares practical systems, tools, and strategies to help you reclaim your time and run your business without sacrificing your the rest of your life, or your health. 

    Start with the free Solopreneur Sweep — a step-by-step method for finding where your business is losing time: https://streamlined.fm/sweep

    If this episode helped you, leaving a review on Apple Podcasts helps other solopreneurs find the show — it only takes a minute and means a lot.

    Connect with Joe on LinkedIn: https://www.linkedin.com/in/jcasabona/

    Listen to the Episode

    Read at Source

  • June 20, 2026

    The content organization system every solopreneur needs

    The content system I use to stay a month ahead — so I never recreate work or stare at a blank page. Here's the simplest version, then my full content planner.

    A few years back I re-recorded a podcast episode I'd already made six weeks earlier — total wasted time. So I built a content system that tracks every idea across podcast, newsletter, YouTube, and LinkedIn. In this video I show the simplest starting point (a free Trello board), then my actual Notion content planner, plus how I used Claude and the Kit MCP to backfill 18 months of newsletters so I can search my own archive and never start from scratch.

    Get my Solopreneur System Starter Kit — the full content system plus three other systems every solopreneur needs: https://streamlinedfm.com/kit?utmsource=youtube&utmmedium=description&utm_campaign=content-system

    Chapters

    0:00 The Pain of Creating Content Without a System 2:20 Why Solopreneurs Need a Content System 4:29 The Simplest Starting Point: Trello 8:13 A Walkthrough of My Notion Content Planner 12:42 Using Claude and Kit to Manage Your Database 16:46 The Ultimate Benefits of Having a System

  • June 20, 2026

    Is speaking worth my time, Zuck doesn’t get people, HotD [Friday Wrap-Up]

    This week I talk about why this is my heaviest speaking year since before the pandemic — and how I’m deciding whether all that travel and prep time is actually worth it, given the real cost of crafting talks and getting clients from them. Then a story about Mark Zuckerberg telling Meta employees to “have fun again” after brutal layoffs, including the absurd perk of a permanent desk. And a recommendation for House of the Dragon Season 3, which drops June 21st.

    Links:

    If you enjoyed this, consider joining my newsletter at https://streamlined.fm/wrap. You’ll get an additional Automation of the Week, as well as regular emails on how to approach building systems that help you take time off, worry-free.

    Register for my free workshop with Ecamm: https://ecamm.com/joe

    View the episode transcript

    • (00:00) – Introduction
    • (00:26) – On My Mind: Is speaking worth my time?
    • (07:17) – Zuck doesn’t get people
    • (12:41) – House of the Dragon S3
    • (14:21) – Free eCamm Workshop (June 25)
    • (16:15) – Outro

    ————
    Streamlined Solopreneur is the podcast for solopreneurs who want to automate their business and take time off worry-free. Each week, Joe Casabona shares practical systems, tools, and strategies to help you reclaim your time and run your business without sacrificing your the rest of your life, or your health. 

    Start with the free Solopreneur Sweep — a step-by-step method for finding where your business is losing time: https://streamlined.fm/sweep

    If this episode helped you, leaving a review on Apple Podcasts helps other solopreneurs find the show — it only takes a minute and means a lot.

    Connect with Joe on LinkedIn: https://www.linkedin.com/in/jcasabona/

    Listen to the Episode

    Read at Source

  • June 17, 2026

    2026 Summer and Fall Speaking Events

    I’m back on the speaking circuit this year, speaking at several events online and throughout the USA. It kicked off with Solo Summit by Lettuce Financial in May, and it’s continuing on here:

    June 25–26: Make Time For Content That Connects (Virtual)

    • Event: Online Workshop
    • Dates: June 25–26, 2026
    • Location: Virtual
    • Full Talk Title: Make Time for Content That Actually Connects

    I’m partnering with Ecamm to bring you a free 2-day workshop where I’ll show you exactly how I produce my weekly YouTube show / podcast in less than 90 minutes.

    Most people I talk to want to use AI to make content faster. But faster isn’t better — it’s just faster. The real issue is that we have so much to do, we need to prioritize a few things and find shortcuts for the rest.

    Find the right shortcuts, and you’ll have the time and space to make content that actually connects.

    Register Here For Free

    July 9–12: Ecamm + Automation = Perfect Setup (Macstock)

    • Event: Creator Camp: Mac Edition at Macstock
    • Dates: July 9–12, 2026
    • Location: Crystal Lake, IL
    • Full Talk Title: Combining Ecamm Live with Automation for the Ultimate Hands-Off Setup

    Join me live in Crystal Lake, IL (near Chicago) at Macstock, where we’ll go hands-on on how to combine Ecamm with native Mac automations to give yourself a better system that takes up less of your time for process tasks. That way, you can focus on making great content.

    Register for Macstock

    Sept 16–18: How I Created Boundaries in My Inbox (Ops Ahoy)

    • Event: Ops Ahoy
    • Dates: Sept 16–18, 2026
    • Location: Philadelphia, PA
    • Full Talk Title: How I created boundaries in my inbox to help my daughter become a top Girl-Scout Cookie seller instead

    Checking your email is one of those things that feels productive, but quickly leads to prioritizing other people’s tasks over your own. And we know that auto-responders saying you only check your email once per day or having an LLM write responses for you doesn’t solve the problem either. In this session, you’ll learn how I built boundaries and reset expectations in my inbox so I can be present for things that matter most, and work as a group to brainstorm similar implementation tactics that work for you and your team.

    Register for Ops Ahoy

    Sept 28–30: Make Time for Content That Actually Connects (Creator Camp)

    • Event: Creator Camp
    • Dates: Sept 28–30, 2026
    • Location: Portsmouth, NH
    • Full Talk Title: Make Time for Content That Actually Connects

    Most people I talk to want to use AI as part of their content creation process to make it faster; but faster isn’t better…it’s just faster.

    The real problem is that we have so much to do that we need to prioritize certain things and find shortcuts for others. But if you can find the right shortcuts you will have the time and space to create authentic content that helps your audience connect with you. Ecamm Live can help you do that.

    Register for Creator Camp

    Oct 15–18: How to Figure Out What’s Worth Your Time (Momentum Weekend)

    • Event: Momentum Weekend
    • Dates: Oct. 15–18, 2026
    • Location: Disney World (Orlando, FL)
    • Full Talk Title: Figure Out What’s Worth Your Time With a Task Audit Matrix

    Busy and productive are not the same, but it can be hard to know what tasks you definitely need to do vs. what tasks you can automate. In this workshop, I’ll show you my Task Audit Matrix to determine what your Focused, Planned work should be, vs. the stuff you can automate. Then you’ll build your own!

    SAVE $200 WITH CODE JOE200

    Register for Momentum Weekend

  • June 16, 2026

    You Can’t Automate What You Can’t Explain

    Here’s the problem: most solopreneurs don’t know exactly what they do. They can’t explain it, so they can’t build systems around it. And when we try to build systems without explaining them, they end up with bad, ineffective systems. Because when we explain, we scrutinize.

    How do you fix it? Pick one task you do often, fire up a screen recorder, and narrate how you do it and why. Recording yourself doing your task is the blueprint. It is the plan. That’s the first step to understanding the systems you can build, so you can automate your business and take time off worry-free.

    Want a second set of eyes on yours? Record one task or workflow you do regularly and submit it at https://taskteardown.com — if I pick your video, I’ll break it down on my YouTube channel with feedback on how to do it better. It’s completely free.

    • (00:00) – Intro
    • (05:59) – When we explain, we scrutinize
    • (10:20) – The exercise: record how you do one task
    • (12:57) – Recording for yourself vs. recording for others
    • (22:13) – Task Teardowns

    ————
    Streamlined Solopreneur is the podcast for solopreneurs who want to automate their business and take time off worry-free. Each week, Joe Casabona shares practical systems, tools, and strategies to help you reclaim your time and run your business without sacrificing your the rest of your life, or your health. 

    Start with the free Solopreneur Sweep — a step-by-step method for finding where your business is losing time: https://streamlined.fm/sweep

    If this episode helped you, leaving a review on Apple Podcasts helps other solopreneurs find the show — it only takes a minute and means a lot.

    Connect with Joe on LinkedIn: https://www.linkedin.com/in/jcasabona/

    Listen to the Episode

    Read at Source

  • June 15, 2026

    The Fewest Links Philosophy: How to Build Automations That Don’t Break

    There’s a children’s game in Philly / eastern PA that’s called “Whisper Down the Lane.” Pretty much the rest of the USA calls it “Telephone.” If you’re unfamiliar with the game, a bunch of kids sit in a line, and the first person whispers…

    The post The Fewest Links Philosophy: How to Build Automations That Don’t Break appeared first on Streamlined Solopreneur.

    Read at Source

  • June 13, 2026

    Siri’s big update, and a CRAZY LEGO scandal [Friday Wrap-Up]

    This week I talk about WWDC and the big Siri update Apple just announced and why Apple’s measured, context-aware approach feels like the right application of AI.

    Then the wild, still-unfolding Reckless Ben vs. Bricks and Minifigs saga, where a consigned Star Wars LEGO collection turned into a legal nightmare, and a recommendation for my own Alphabet Playlist: one album from one band for every letter of the alphabet, on Apple Music and Spotify.

    Links:

    If you enjoyed this, consider joining my newsletter at https://streamlined.fm/wrap. You’ll get an additional Automation of the Week, as well as regular emails on how to approach building systems that help you take time off, worry-free.

    View the episode transcript

    • (00:00) – Introduction
    • (00:28) – WWDC and Siri’s Big Update
    • (05:30) – Reckless Ben vs. Bricks and Minifigs
    • (09:58) – Recommended Media: The Alphabet Playlist
    • (13:54) – Free Ecamm Workshop
    • (16:08) – Outro

    ————
    Streamlined Solopreneur is the podcast for solopreneurs who want to automate their business and take time off worry-free. Each week, Joe Casabona shares practical systems, tools, and strategies to help you reclaim your time and run your business without sacrificing your the rest of your life, or your health. 

    Start with the free Solopreneur Sweep — a step-by-step method for finding where your business is losing time: https://streamlined.fm/sweep

    If this episode helped you, leaving a review on Apple Podcasts helps other solopreneurs find the show — it only takes a minute and means a lot.

    Connect with Joe on LinkedIn: https://www.linkedin.com/in/jcasabona/

    Listen to the Episode

    Read at Source

  • June 10, 2026

    How Claude Makes Notion Easy for Solopreneurs

    I stopped fighting Notion and let Claude build it for me — databases, migrations, a full content hub. Here's the whole thing on camera, with Claude.

    If you've bounced off Notion because it felt like too much, this is the workaround: let Claude do the building. I connect Notion to Claude, create a clean database in a couple of prompts, move 20+ posts over automatically, and pull everything into one content hub — without touching a single formula.

    Try it on one of your own messy systems and show me in the comments.

    Check out my full Solopreneur Systems Starter Kit at https://streamlined.fm/kit

    Did Claude build something good for you? Drop it in the comments — I read every one.

    0:00 Making Notion Easier for Solopreneurs 1:41 Connecting Claude to Notion via MCP 3:07 Testing the Notion Integration 4:11 Designing a Custom LinkedIn Database 7:23 Transferring and Populating Data 9:06 Building a Multi-Source Content Hub 10:25 Conclusion and Next Steps

    Related: https://www.youtube.com/watch?v=d7lb_v67btQ

  • June 9, 2026

    AI for Solopreneur Systems: Two Projects That Actually Worked

    I talk a lot about the wrong ways to use AI. But a rainy weekend gave me a few free hours and two pet projects that I used Claude Cowork for— and the results actually impressed me.

    The first: I used Claude to vibe-code a custom Obsidian theme from scratch. No CSS, no digging through the inspector — just a few prompts and some back-and-forth until it looked exactly the way I wanted.

    The second: a Claude skill that plans trips for me end-to-end — packing list, budget, Todoist project, calendar entries, the works. It’s now maybe my favorite thing I’ve ever built in Claude.

    Does all of this sound interesting, but you’re not sure where to start with your systems? Grab the free Solopreneur Systems Starter Kit — including the trip planning skill from this episode — at streamlined.fm/kit

    Links

    • (00:00) – Intro
    • (01:28) – What AI is actually good at (and what it’s not)
    • (04:22) – Vibe-coding a custom Obsidian theme
    • (11:00) – A Claude skill that plans trips end-to-end
    • (17:42) – Wrap-up

    ————
    Streamlined Solopreneur is the podcast for solopreneurs who want to automate their business and take time off worry-free. Each week, Joe Casabona shares practical systems, tools, and strategies to help you reclaim your time and run your business without sacrificing your the rest of your life, or your health. 

    Start with the free Solopreneur Sweep — a step-by-step method for finding where your business is losing time: https://streamlined.fm/sweep

    If this episode helped you, leaving a review on Apple Podcasts helps other solopreneurs find the show — it only takes a minute and means a lot.

    Connect with Joe on LinkedIn: https://www.linkedin.com/in/jcasabona/

    Listen to the Episode

    Read at Source