Streamlined Solopreneur: Helping Solopreneurs Automate to Take Time Off Worry-Free

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, but I don't even know where to start." That was maybe the most important thing I've heard since I moved away from web development. So I finally decided to solve it.

That's why I built the Solopreneur System Starter Kit, and today I walk you through the four systems every solopreneur nee...

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 key combos and Raycast actions — and why these little tactile hardware automations are easier on your brain than memorizing keyboard shortcuts. Then a MacStories write-up that inspired the whole experiment, walking through real use cases for turning a game controller into a Mac...

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 Pilla...

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 Drago...

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. ...

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 ...

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 ...

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 form your own opinion, and I'd rather read one primary source than 14 summaries I'll forget. Then a heavy but admirable piece from The Dispatch on Ben Sasse facing terminal cancer with poise, and what it teaches us about being present with our families, and a recommendation for L...

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 you’re a solopreneur, you know that’s a big deal. It’s all thanks to my startup and shutdown routines. And I know I’ve talked about them on the show before, but something interesting has happened over the last year.

As LLMs and AI tools have been able to connect t...

This week I talk about my surprisingly productive Saturday mornings — and why I'm hoping that same quiet, distraction-free focus carries into summer with all three kids out of school. Then The Creative Act by Rick Rubin, which pulled me out of a months-long reading slump in just a few days, and a recommendation for my early-to-mid 2000s pop punk discography playlists on Apple Music.

Links:

• We're trying to summer camp again ...

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 somehow still get home without the one thing you actually needed.

Running a one-person business without a real task capture system feels exactly the same.

When everything falls on you, important work slips through the cracks. And without a plan, it's easy to spend your day on somethi...

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 instead of grinding through business prep. Then a wholesome story about a teen umpire who handled a coach's meltdown with poise, and a recommendation for SNL's The Rundown series on YouTube.

Links:

• Solopreneurs and forced downtime
• A teen umpire tossed a baseball coach in a now-viral...

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 urgent. What if a client needs something? What if you miss a deal?

But after nearly a decade of refining my approach, I've built a technical system that keeps my inbox at (or close to) zero — without having to check it constantly.

In this episode, I walk through the full ...

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 Reading, and Recommended Media. Here's what's on my mind...

Earlier this week I found myself fighting Claude on something I felt was a pretty basic problem — one that I had used it to solve before. I kept going back and forth with Claude. I would ask it questions. It would then ...

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 hear constantly when I coach solopreneurs. Either they don't have a newsletter because it feels like too much work, or they have one, but they're paying for a plan they don't actually need. And in almost every case, it's not a strategy problem. It's a tool problem.

That's why ...

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 great article about why it might actually be bad that you're storing every little thing in your second brain, and a fantastic performance from SNL.

Finally, a pay small tribute Yankees legend, John Sterling, who passed away earlier this week.

Get the newsletter version at https://streamline...

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 overstimulated and realized it would take about five minutes to clean it up. So we did — and suddenly it was a great place to hang out again.

A lot of solopreneur businesses are like that sunroom. They're not broken. They don't need a massive overhaul. They need a quick sweep —...

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 my friend invited me to see it with him. 

He realized I had never seen the Original Trilogy when I was surprised that Qui-Gon Jinn died (spoiler, I guess). We fixed that quickly, but this movie, despite being considered the worst Star Wars movie of all time (maybe bottom 2 no...

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 not quite my way, and I'm not the only one.

 Also: a well-researched piece on why AI isn't actually coming for your job, and some very good news for Ted Lasso fans.

• On My Mind: Single purpose apps/the age of personalized software.
• Recommended Reading: The task is not the job
• Recomm...