Streamlined Solopreneur: Helping Solopreneurs Take a Guilt-Free Vacation
Joe Casabona, Business Systems Coach
You started your business for freedom, not to be chained to your desk. I help solopreneurs build better systems they trust, so the can take time off without worrying.
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. But more than that, He's a teacher at heart.
His goal isn’t to overwhelm you with jargon, but to make complex ideas simple and give you an actionable plan you can actually use.
Because your business should support your life—not take it over.
Tune in every Monday, wherever you get your podcasts.
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. But more than that, He's a teacher at heart.
His goal isn’t to overwhelm you with jargon, but to make complex ideas simple and give you an actionable plan you can actually use.
Because your business should support your life—not take it over.
Tune in every Monday, wherever you get your podcasts.
Episodes
Mentioned books
Feb 5, 2026 • 7min
Working on Interoperability with the reMarkable 2 [Audio Note]
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 ★
Feb 2, 2026 • 18min
What do we lose by relying on AI too much?
A contrarian take on AI hype and what we risk when we outsource creativity. A look at how famous creators worked without AI and why making time for original thought matters. Practical rules for when to use AI for research, data, and proofreading but not for first drafts. A charming Girl Scout cookie story as a metaphor for showing up and doing the work.
Jan 30, 2026 • 7min
January Accountability Report for Digital Detox [Audio Note]
A January accountability check on a Year of Digital Detox and what’s working so far. Switching to analog tools like a reMarkable for distraction-free writing. Cutting back social media while noting slips to LinkedIn and Blue Sky. Reading more physical books and planning classic and nonfiction reads. Leaving the phone behind for presence and setting tangible goals for February.
6 snips
Jan 26, 2026 • 22min
Why Gear and Tools Actually Matters
A practical look at how hardware and software can save hours in daily business operations. Stories about calendar chaos and hosting headaches show how bad tools multiply work. Specific setups like Stream Deck, Rodecaster Pro 2, Ecamm Live, Tella, and Todoist illustrate time-saving choices. Learn a simple audit framework to spot friction and decide when switching tools is worth it.
Jan 19, 2026 • 44min
How AI Can Actually Help Your Critical Thinking, not Hurt It
Join Christian Ulstrup, an Applied AI practitioner and consultant, as he dives into the intriguing intersection of AI and critical thinking. Christian argues that AI, rather than dulling our intellect, can enhance our thinking by compressing digital exhaust into actionable insights. Discover his innovative Walk and Talk Framework, which helps users provoke deep thought through AI-generated questions. They also tackle the potential of AI in education, advocating for project-based learning to adapt to a rapidly changing world.
Jan 12, 2026 • 55min
How to Serve More People and Scale Your Income
Join Jonathan Stark, a solo consultant and author specializing in value-based pricing, as he shares insights on scaling income without burnout. He discusses the pitfalls of hourly billing and how it limits efficiency. Stark emphasizes the potential of value-based pricing by focusing on client outcomes and creating distinctive offerings. Learn how solopreneurs can leverage automation and AI to deliver greater value while avoiding competition on price. With advice on targeting high-value problems and creating product ladders, Stark offers a roadmap to success in the solo business landscape.
6 snips
Jan 9, 2026 • 4min
New Podcast: Paper & Smoke [Trailer Drop]
In a world dominated by digital distractions, the host embarks on a digital detox to reconnect with the tangible. He reflects on the importance of analog experiences and the joy of hands-on craftsmanship. Exploring the balance between technology and real-life activities, he emphasizes the unique value human effort brings that AI cannot replicate. Listeners are invited to join a journey of rediscovery, focusing on hobbies like fountain pens and cigars, while celebrating the enduring significance of paper and fire.
12 snips
Jan 5, 2026 • 30min
The Year of Digital Detox (2026 Yearly Theme)
This discussion dives into the idea of a digital detox for the upcoming year. The host reflects on lessons learned from a year focused on being present. He shares goals like using devices less, enjoying the analog world, and reducing reliance on social media. Tactics include leaving phones behind and gaining knowledge through craft and books. The emphasis is on finding balance and engaging in physical activities. It’s a refreshing take on how to unplug and reconnect with the real world.
Jan 1, 2026 • 4min
An End of the Year (Beginning of the Year?) Update
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 ★
11 snips
Dec 31, 2025 • 29min
My Favorite Tech, Apps, and Media of 2025
Get ready for a whirlwind tour of 2025's top media and tech picks! Highlights include the captivating documentary 'Alex vs. A-Rod,' the emotional memoir 'Fahrenheit 182,' and the must-listen podcast 'The Rest Is History.' Joe shares his favorite tunes, including the melancholic 'Sad' by Mayday Parade, and discusses gaming fun with 'Hogwarts: Legacy.' Discover transformative apps like Tella that revolutionize video workflows. Plus, hear about Joe's shift from Dropbox to Google Drive and reflect on the benefits of leaving social media behind!
