Streamlined Solopreneur: Helping solopreneur parents stop checking email at the playground
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Streamlined Solopreneur: Helping solopreneur parents stop checking email at the playground
Overwhelmed? Feel like your business can't run for a day without you? You're not alone. When you're a solo business owner, everything ends up depending on you. You're the only one who can do the work, answer the email, keep the plates spinning. So you're on the hook every day: nights, weekends, e...
Recent Episodes
591 episodes![Writing With AI Isn't Like Using a Calculator [Friday Wrap-Up]](https://img.transistorcdn.com/FSqgO_m0RJmtsO2-7EqOopR2YbpC-VdL66fZvkr9Vx8/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS82OTYz/NWNlMzMxYzUzMTYz/MTg4OTg3OGE4MmFm/MzI4My5wbmc.jpg)
Writing With AI Isn't Like Using a Calculator [Friday Wrap-Up]
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...
When to Use Automation vs. When to Use AI
AI and Automation are not the same thing. But people seem to use the terms interchangeably. Tools like Zapier and Make are deterministic automation —...
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Are You Practicing Conscientious AI Usage? [Friday Wrap-Up]
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...
How to Start Thinking in Systems
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. Half...
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Am I wrong about AI-generated YouTube thumbnails? [Friday Wrap-Up]
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 o...
The Lie That AI Is a Magic Shortcut
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 mor...
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Resetting Claude Every 3 Months? [Friday Wrap-Up]
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...
You Don't Have to Fix Everything — Just Start With One Thing
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. Bus...
"No One Can Do It Like Me" Is a Lie (And It's Costing You)
For most of my life, I believed that if I wanted something done right, I had to do it myself. I held it all the way until I had a panic attack and had...
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The Simplicity of Yellow Legal Pads [Friday Wrap-Up]
This week I talk about rediscovering the humble yellow legal pad after years (and hundreds of dollars) sunk into fancy notebooks and fountain pens. Th...
Welcome to The Streamlined Solopreneur
Imagine you finally logged off. It's the first real vacation you've taken in years. The coffee's hot (or iced), the phone's in the other room, and for...
How I Produce a Week of Content in 90 Minutes
I was at a retreat with my mastermind group. We were going over our big takeaways, and my friend Cat reminded me of something: I output more content t...
![When is implementation the problem? [Friday Wrap-Up]](https://img.transistorcdn.com/uKRkv3fqi2c1jjd-HFDGFjYn9aIf--FZaSWoj1146lE/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS8zZDA2/MDc1NjU5NzdlMTM5/N2Y1MGU4ZjIzNzQz/ODJjNi5wbmc.jpg)
When is implementation the problem? [Friday Wrap-Up]
This week I talk about when implementation itself becomes the blocker — how working on a new welcome sequence in Kyle Adams' Newsletter Power-Up Cohor...
Why Your Solopreneur Business Feels So Complicated
One of my favorite shows is Scrubs, and there's one episode that's stuck with me for nearly 2 decades, and I think about it nearly every day. In it, t...
![Is Claude Winning? [Friday Wrap-Up]](https://img.transistorcdn.com/QF5sju0ROLuaLtSvNqzwd4OeS83lReg9HQZCgx-UgLM/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS9iNDdi/ODVmNDEyZDI5Mjhh/MzA0NGI0NzkwMDRi/OWFhNC5wbmc.jpg)
Is Claude Winning? [Friday Wrap-Up]
This week I talk about whether Claude is quietly winning the AI war — at least among business owners and tech nerds — after every speaker at Ecamm Cre...
Stop Being the Bottleneck in Your Content Creation
Imagine making yourself a bowl of cereal. But instead of grabbing a bowl from the cupboard, you head to your backyard, throw a brand-new bowl on the p...
![Getting Distracted, Disney, and LEGO [Friday Wrap-Up]](https://img.transistorcdn.com/rLvCSi5NZRW-tdk0-6JGO2Si4pD8ZtFVWqIbs3v9fGQ/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS9jNTUx/ODVhNzE3NDhlNjUy/MWZiODg5YWZiMjhj/MTc5NC5wbmc.jpg)
Getting Distracted, Disney, and LEGO [Friday Wrap-Up]
This week I talk about almost re-joining a platform I know I'd hate. Then a look at Disney's next-gen audio-animatronic transforming from a pirate to...
The 4 Systems Every Solopreneur Needs to Take More Time Off
A few months ago I was doing a series of research calls, and the same piece of feedback kept coming up: "I read all your stuff, this sounds awesome, b...
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I bought a tiny game controller for automation [Friday Wrap-Up]
This week I talk about my latest Mac automation tool: the 8BitDo Micro, a $15 tiny game controller I picked up during Prime Week and mapped to complex...
Automate Without Losing Critical Thinking (My AI Philosophy)
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 fo...
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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...
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 t...
![Siri's big update, and a CRAZY LEGO scandal [Friday Wrap-Up]](https://img.transistorcdn.com/tO1-xxhMHcmuO3u1GVrx1PXHqBM4CP2vUcL4au1mzMs/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS8yMTdm/NTNiMjM4NjdlOTBi/NTcyZTAzOTg2ZWQw/MGUzZC5wbmc.jpg)
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 applica...
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...
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Why Summarize Everything, Ben Sasse, and Lou Gehrig [Friday Wrap-Up]
This week I talk about why summarizing everything isn't actually reading more — summaries rob you of the experience, the context, and the ability to f...
The Automated Routine That Lets Me Leave Work at Work
I left work early recently to volunteer at my daughter's ice cream social and sit through her spring concert without checking my phone once. And if yo...
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Saturday Mornings, The Creative Act, and Pop Punk [Friday Wrap-Up]
This week I talk about my surprisingly productive Saturday mornings — and why I'm hoping that same quiet, distraction-free focus carries into summer w...
"I'll Remember It" Is a Lie: 3 Ways Solopreneurs Can Capture Tasks Faster
Have you ever gone to the grocery store without a list? You walk down every aisle, grab whatever looks good, spend way more than you planned — and som...
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Do you work while driving? [Friday Wrap-Up]
This week I talk about how I used 4 hours of solo driving to and from a mastermind retreat in Baltimore — and why I chose to turn everything off inste...
Inbox Zero for Solopreneurs: The Exact System I've Used for 8 Years
Have you ever seen a 5-digit notification badge? It’s most stressful things I see on someone's phone. And I get it — as a solopreneur, email feels urg...
![Do LLMs employ variable rewards, Spike Lee's hat, and a chilling video [Friday Wrap-Up]](https://img.transistorcdn.com/mB4dwYEsGHRVJkbsQxKlkfsrN7mLFevvyu11jjp1R-s/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS9iMGY5/ZjM3NzBjYTE1MjAw/MjE5MjI4MzkwNGIx/MzMwMC5wbmc.jpg)
Do LLMs employ variable rewards, Spike Lee's hat, and a chilling video [Friday Wrap-Up]
Welcome to the Friday Wrap-Up for May 15, 2026. This is a short newsletter where I talk about 3 things: What’s on my mind this week, Recommended Readi...
The Right Newsletter Tool Makes All the Difference: Why Solopreneurs Should Use Kit
Does having a mailing list feel like too much for you? Like it’s adding “one more thing” to your list as a one-person business?
That's what I he...
![Don't Miss Out on What You're Doing, Deleting Second Brains, drop dead [Friday Wrap-Up]](https://img.transistorcdn.com/x7UNEtnVUCU7uQLvywUjnE7Vz_HjTDq0obrlkAcIvrI/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS9kM2Zl/ZmY4MjlmMTllMmNh/YWNlMjBkMjBlMjEy/ZGEwMy5wbmc.jpg)
Don't Miss Out on What You're Doing, Deleting Second Brains, drop dead [Friday Wrap-Up]
Are you so concerned with FOMO that you're Missing Out On What's There, rendering your real life MOOWT? That's what's on my mind today.
Plus, a...
Why Your Solopreneur Business Feels Overwhelming (Fix This First)
The most overwhelming room in my house is the sunroom. Three small kids, all their toys, total chaos. One day, I was sitting in there feeling overstim...
What Solopreneurs Can Learn From Star Wars
I have a confession to make: The first Star Wars movie I ever saw was Episode 1: The Phantom Menace. I was 13, and it just hit the dollar theater when...
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Single-Purpose Apps, AI Won't Take Your Job, Ted Lasso is Back [Friday Wrap-Up]
Are single-purpose apps going to replace SaaS? I've been building small, focused tools with AI to replace subscriptions that solve my problem, just no...
The One Thing Solopreneurs Shouldn't Automate (And What to Automate Instead)
Using AI to write your book is like using a car to run your marathon. Sure, you covered the distance — but nobody's impressed.
Here's what I'm s...
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Trading Algorithms + Claude MYTHos [Friday Wrap-Up]
This week I've been deep in my SEO and content strategy, and it got me thinking: am I just trading one algorithm for another? I left social media to s...
The Solopreneur's Guide to Discipline: Systems, Time, and Delegation
What if the best business advice you ever got came from a book about ancient philosophy?
I've been on a bit of a reading bender this year — phys...
![What is AI Brain + Recommendations [Friday Wrap-Up]](https://img.transistorcdn.com/lffazziQsjB86hn6iKR2xYzHlOnGaZW4_VS8iR4u4Ig/rs:fill:0:0:1/w:1400/h:1400/q:60/mb:500000/aHR0cHM6Ly9pbWct/dXBsb2FkLXByb2R1/Y3Rpb24udHJhbnNp/c3Rvci5mbS9hNTVh/MDVkMjg3MWIzNGIx/MDA1ZDY2MTg0YmMw/NzdiMC5wbmc.jpg)
What is AI Brain + Recommendations [Friday Wrap-Up]
AI brain is when you've come to rely on AI for even the most basic things -- and after a week deep in Claude Max, I felt it creep back in. I'm sharing...