7 mins S2 #546 Aug 18, 26 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. 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 people are just wired for this, and they're not, that it's a willpower fail. I don't buy it. Thinking in systems is a skill you can learn, not a gift you're handed. Here’s how. Looking for a place to start? Grab the free Solopreneur Systems Starter Kit — the 4 systems every solopreneur needs, plus the exact tools, automations, and AI prompts to set them up: https://streamlined.fm/kit
9 mins S2 #545 Aug 14, 26 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 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 that gathers my recorded calls, summarizes them into Obsidian, routes action items to Todoist, and files client transcripts for voice-of-customer research.Links:AI Brain RotvidIQ-generate Thumbnail of meSuperintelligence is a dragon (Platformer) Call Debrief Prompt: I want you to pose to me three extremely precise, very hard-hitting questions, all of which are independent and have different coverage, that if sufficiently answered, would yield some kind of transformative, genuinely novel, impactful insight. Please make reference to the primary source material where appropriate in the context of the question.These episodes are about taking more time off — especially on the weekends. The best way you can do that is by having a good system. If you're not sure where to start, head over to https://streamlined.fm/quiz. Answer a few questions, and I'll send you exactly where you should start to build a less overwhelming business.
11 mins S2 #544 Aug 11, 26 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 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 bullet that produced articles for him. That's what I want to talk about this week — the lie that AI is a magic shortcut, that if you're not using it you're going to fall behind. And sure, AI can write stuff. So can my five-year-old. That doesn't mean it's going to be good. Here's the truth: if you stop doing the craft, you will no longer be good at the craft. Let’s make sure that doesn’t happen. Want some actually good ways to use AI? Grab the free Solopreneur Systems Starter Kit — the 4 systems every solopreneur needs, plus the exact tools, automations, and AI prompts to set them up: https://streamlined.fm/kit Links3 Signs You Have AI Brain Rot
9 mins S2 #543 Aug 07, 26 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 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 setting inbox boundaries. Links:Boris Cherny interview (YouTube)Destiny of the Republic by Candice Millard2026 Yearly Theme: Digital DetoxOps AhoyThese episodes are about taking more time off — especially on the weekends. The best way you can do that is by having a good system. If you're not sure where to start, head over to https://streamlined.fm/quiz. Answer a few questions, and I'll send you exactly where you should start to build a less overwhelming business.
8 mins S2 #542 Aug 04, 26 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. 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 some reason, when it comes to our business, a lot of us tell ourselves: I have to fix everything right now, immediately. But you can’t when you don’t know the first step. In this episode, I’m going to tell you how to take the first step. And if you are still looking for a place to start? Grab the free Solopreneur Systems Starter Kit — the 4 systems every solopreneur needs, plus the exact tools, automations, and AI prompts to set them up: https://streamlined.fm/kit