Streamlined Solopreneur: Easy Productivity & Tech Systems for Solopreneurs
Overwhelmed? Feel like your business can't run for a day without you? You're not alone. When you're a solopreneur, everything ends up depending on you. You're the only one who can do the work, answer the email, keep the plates spinning, make the decisions. So you're on the hook every day: nights, weekends, even the vacations you do manage to take. The overwhelm never really lifts. But being a solopreneur doesn't have to mean doing it all yourself. With the right systems, parts of your business can run without you. That's what gets you your time back, and gives you the freedom to take a real break. And the freedom to do the work you actually want instead of the work you feel stuck doing. Joe Casabona learned this the hard way. He went from so overwhelmed he had a panic attack to taking 4–6 weeks off a year, worry-free, and he's helped hundreds of solopreneurs build systems that give them their time back. On Streamlined Solopreneur, each episode gives you one clear idea to help you get your time back — and exactly what to do, so you don't just have another decision to make. Start listening. And you want to take action right now, take the Solopreneur Systems Quiz to know which system you should fix first, and how: https://quiz.streamlined.fm
Episodes
Do you really need to answer every email right away? You definitely don’t. That’s a story we tell ourselves. But the truth is no one is sitting at their inbox waiting for your email. And in today’s episode, I tell you how you can start letting go…but more importantly, why you need to.
Are you ready to get your 25 hours back? Book a free strategy call — no strings attached.
Show Notes
This week I talk about whether AI is really saving us time and money, and how using Claude to rebuild my WordPress theme between sections made this newsletter take longer than usual. Then Cal Newport on AI's jagged abilities, and a recommendation for "Chronically Cautious" by Braden Bales on YouTube. Plus this week's systems tip: the Stream Deck + XL.
I'm working on a new cohort around how to vibe code your own tools. If you want to...
Should you replace your software subscriptions with tools you vibe code? I've replaced several of mine, but I'll never replace others. Here's how I decide, using four questions: skill, expertise, tools, and the one that matters most, dependency.
Want help figuring out what to replace and building it to last? Join the waitlist for my upcoming cohort on how to vibe code your own tools: streamlined.fm/waitlist
This week I share what I learned after speaking at Ecamm's Creator Camp: why listing the simple automations I use landed better than I expected, and how my "AI is for tasks, not craft" line ended up on the quote board. I also go through four questions I'm asking myself now.
Should I go back to Instagram? What should my YouTube pillars be? Do I need a simple digital product? And when should you code your own tool instead of paying fo...
My clients spend more time with their families, serve their community, and even have time to write their book. What would you do with 25 extra hours a month? While building a system is how you get there, today I want to focus on what you get.
Are you ready to get your 25 hours back? Book a free strategy call — no strings attached.
Show Notes
This week I talk about converting casabona.org from a 20-year-old WordPress site to a flat-file site in two days — and whether my mailing list needs the same "burn it all down" reset. Then Apple's final Friday Night Baseball broadcast of the year, shot on the iPhone 18 Pro Max, and a recommendation for my Italian music playlist on Apple Music. Plus this week's systems tip: Cue for Apple Music, the Stream Deck plugin I built w...
I hate lunch. I’m never prepared for it, so I just end up wasting a bunch of time before picking the fast, easy thing. If I did some meal prep, this wouldn’t be a problem.
But many solo business owners do the same thing with their work. They sit down, they shrug their shoulders, and wonder what to do. Everything takes more time because it's not written down.
That’s why today I'm walking through how to create an SOP ...
This week I'm doing a Pick Two for Voice Note apps (plus the one I’m not using, and a bonus transcription app)
#1 is Whisper Memos, which I happily pay for because of one killer feature.
#2 is Audio Pen, which gives me system-wide dictation: press a key, talk, and the text lands wherever my cursor is. That's what I use for long prompts to a large language model.
This week I talk about the iPhone Duo — my first real foldable — and why I'll trade away the telephoto lens, action button, and fast charging (and swallow a $2,100 price plus the end of the annual upgrade program) for a big anti-glare screen that folds into my pocket and takes an Apple Pencil.
Then an episode of Ditching Hourly with Nick Richtsmeier on doing things that don't scale and focusing on impact, which sold me ...
When I was 17, my high school organized a two-week trip to Italy and Ireland for $900. My dad offered to pay for it. I said, "Why do I need to go when I can just look at pictures online?"
Seventeen-year-old Joe, you were so, so stupid. I’ve since learned that photos aren’t the experience. Just like ideas aren’t the fully fleshed-out thought.
On top of a passionate credo about why we need to write for ourselves, I te...
This week I talk about a Steve Thompson video that's had me rethinking my whole approach — the idea that teaching tactics on YouTube actually costs you clients, because when you hand people the solution they assume they can do it themselves. After a rough summer where teaching hasn't yielded new business, I've decided to make September an experimental month: teach less, shift beliefs more, and stop being afraid to sell. Then ...
There was a time when building a quiz as a lead magnet seemed insurmountable to me. The setup, the configuration, the routing — not to mention how much those tools cost. It never felt like the juice was worth the squeeze.
LLMs have changed that. So today I'm walking through exactly how I built my Conscientious AI Usage quiz, and how you can too.
Take the quiz at quiz.lovehate.ai — find out if you're at risk of AI brai...
This week I talk about why writing with AI isn't the same as using a calculator for math — financier Stanley Druckenmiller defended his AI-written WSJ critique of Scott Bessent by calling it "using a calculator," and I break down why that misunderstands math, calculators, and words.
Then the unraveling of Ashley Flowers' true-crime podcast empire, and what a founder pulling 3 a.m. alarms on weekends and holidays has to teach ...
AI and Automation are not the same thing. But people seem to use the terms interchangeably. Tools like Zapier and Make are deterministic automation — you know the input, you know the output, and it's incredibly consistent. Large language models are what I'm calling interpretive automation. Run the same thing multiple times and you can get different outputs.
Both can do similar things. I don't treat them the same. And in this e...
This week I talk about Conscientious AI Usage (a term my mastermind group gave me). Then a Six Colors article on Anthropic's lexical watermark and why making LLM output worse might be a net good, and a recommendation for Halo 3 on Game Pass. Plus this week's systems tip: building an "Are You Suffering From AI Brain Rot?" quiz with Claude in a couple of hours between meetings.
Links:
A few years ago, I was helping my friend Jeff rebuild an automation — getting his intake form to talk to his CRM and his project management tool. Halfway through the screen share, he stopped and said, "So you just think like this?" That's when it hit me: not everyone's brain defaults to systems. Mine does…but I wasn't born with it. I learned it.
That's what this episode is about. A lot of solopreneurs tell me some peopl...
This week I talk about whether I'm wrong about AI-generated YouTube thumbnails — I've told my designer to never use AI on them, but if a thumbnail's only job is to get the click, does it matter? Then Casey Newton on Mark Zuckerberg's AI manifesto and why "superintelligence is a dragon" is the analogy that actually fits, and a recommendation for Schmigadoon! on Apple TV. Plus this week's automation: a Daily Call Debrief skill ...
I was talking to an acquaintance recently who told me how he has AI agents write his articles for him. He sends a voice note of an idea, and every morning it picks the ideas, writes the drafts, sends them to him, he requests edits, and then it writes and publishes them. So I asked him: at what point do you feel uncomfortable putting your name on this? And he couldn't even see the issue.
He just thought AI was some amazing magic bull...
This week I talk about a piece of advice from Boris Cherny, head of Claude Code — that you should reset your prompts, projects, and skills every time a new model ships — and why I'm not doing it. Then a recommendation for Destiny of the Republic, Candice Millard's book on James Garfield, and why I've started walking a mile every morning without headphones. Plus a quick promo: I'm speaking at Ops Ahoy this September on s...
Back in 2016, I ran…well, *completed…*a Disney half marathon. And the thing about Disney is they make it impossible not to find the starting line. Buses from the resort, signs, gates, pre-race emails. Everything points you to where to start.
And if I didn’t know any of that, I wouldn’t just start running. I would start simple…like asking a cast member when the race is, and go from there.
But for s...
Popular Podcasts
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com
The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!
The Clay Travis and Buck Sexton Show. Clay Travis and Buck Sexton tackle the biggest stories in news, politics and current events with intelligence and humor. From the border crisis, to the madness of cancel culture and far-left missteps, Clay and Buck guide listeners through the latest headlines and hot topics with fun and entertaining conversations and opinions.
Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by Audiochuck Media Company.