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The Streamlined Solopreneur Newsletter

I help overwhelmed solo business owners go from overwhelmed to having their time back.

Featured Post

The dumbest thing I said as a teenager

Hey Reader, One of the dumbest things I’ve ever said came, unsurprisingly, as a teenager. My high school partnered with a local travel agent (who also happened to be a parent at the school) to organize a 2-week trip to Italy and Ireland…for just $900. Even in 2003, that was super cheap for a 2-week international trip. My dad urged me to go. “I’ll even pay for it. It will be a great experience.” “Why do I need to go when I can just look at pictures online?” 17-year-old Joe: you were so stupid....

The Friday Wrap-Up From The Streamlined Solopreneur Welcome to the Friday Wrap-Up for August 14, 2026. This is a short newsletter where I talk about 3 things: What’s on my mind this week, Recommended Reading, and Something Fun. Here's what's on my mind... On My Mind Am I wrong about AI-generated YouTube Thumbnails? You likely know how I feel about using AI for creative work (I don't like it). I fear too many business owners, including myself at times, suffer from AI Brian Rot from relying too...

The Friday Wrap-Up From The Streamlined Solopreneur Welcome to the Friday Wrap-Up for August 7, 2026. This is a short newsletter where I talk about 3 things: What’s on my mind this week, Recommended Reading, and Something Fun. Here's what's on my mind... On My Mind Resetting Claude Every 3 Months? My friend Doc Rock sent me an interview with Boris Cherny, who's the head of Claude Code, last week while I was on vacation, and the advice struck me. Cherny basically says we should reset our...

The Friday Wrap-Up From The Streamlined Solopreneur Welcome to the Friday Wrap-Up for July 24, 2026. This is a short newsletter where I talk about 3 things: What’s on my mind this week, Recommended Reading, and Something Fun. Here's what's on my mind... On My Mind The Simplicity of Yellow Legal Pads. I am a man who has spent $30-40 on a notebook. Over $100 on a leather-bound disc book with refillable pages. More than I'd like to admit on fountain pens. But over last weekend, I rediscovered...

Hey Reader, Over on LinkedIn last week, someone made a comment on my post that was so very obviously written by AI. And it really got me wondering: what’s the point? Do they think it’s convincingly good at writing comments? Do they think any comment is a good comment? Do they not care? I suspect it’s actually that they care a great deal, but they’re stuck. They want to show up on social media, but they don’t have the time, or they don’t know what to say. So they see AI commenting on their...

The Friday Wrap-Up From The Streamlined Solopreneur Welcome to the Friday Wrap-Up for July 17, 2026. This is a short newsletter where I talk about 3 things: What’s on my mind this week, Recommended Reading, and Something Fun. Here’s what’s on my mind… STREAMLINED SOLOPRENEUR: FROM OVERWHELMED TO BUSINESS YOU CAN STEP AWAY FROM • S2:E When is implementation the problem? [Friday Wrap-Up] 10:53 MORE INFO On My Mind When does implementation hinder you? I’m doing Kyle Adams’ Newsletter Power-Up...

Hey Reader, I just got back from MacStock, where Brett Terpstra mentioned something that inspired me to create my very first Mac app. He mentioned TableFlip, an excellent Mac app for just $10 that allows you to work with tables in Markdown. If you know Markdown, you know how awful tables are to work with. I've spent years creating them by hand. Getting them to look right takes a lot of time (and hope). Now, I didn't buy TableFlip. I actually decided to see if I could code my own version of...

The Friday Wrap-Up From The Streamlined Solopreneur STREAMLINED SOLOPRENEUR: HELPING SOLOPRENEURS AUTOMATE TO TAKE TIME OFF WORRY-FREE • S2:E Getting Distracted, Disney, and LEGO [Friday Wrap-Up] 16:09 MORE INFO Welcome to the Friday Wrap-Up for July 3, 2026. This is a short newsletter where I talk about 3 things: What’s on my mind this week, Recommended Reading, and Something Fun. Here's what's on my mind... On My Mind Getting Distracted: I almost re-joined IG this week. I was told in no...

The Friday Wrap-Up From The Streamlined Solopreneur Welcome to the Friday Wrap-Up for June 26, 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... STREAMLINED SOLOPRENEUR: HELPING SOLOPRENEURS AUTOMATE TO TAKE TIME OFF WORRY-FREE • S2:E I bought a tiny game controller for automation [Friday Wrap-Up] 12:44 MORE INFO On My Mind Hardware Automation Tools: This week I have a 4 hour...

The Friday Wrap-Up From The Streamlined Solopreneur Welcome to the Friday Wrap-Up for June 19, 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... STREAMLINED SOLOPRENEUR: HELPING SOLOPRENEURS AUTOMATE TO TAKE TIME OFF WORRY-FREE • S2:E Is speaking worth my time, Zuck doesn't get people, HotD [Friday Wrap-Up] 16:46 MORE INFO On My Mind I'm doing a lot of talking. I updated my /now...