Dan Cumberland
Weekly AI strategies to reclaim 15+ hours/week— without sounding like a robot. Real systems. Real results. Your voice intact. Join 14,000+ founders.
You got promoted into middle management
Hi Reader, The fear for the last two years: machine does your job. You disappear. What actually happened is stranger. AI took the production work. And immediately proved it has zero judgment. It writes without knowing who it’s writing for. It builds without understanding the context. It moves fast and breaks the things that matter. (Sound familiar? I’ve managed actual humans who worked exactly like this.) So whether you wanted it or not, you became the manager. Your new daily job: Giving...
The tool works. People just run out of ideas.
Hi Reader, The tool works. People just run out of things to ask it. Cowork shipped out of beta this week. And the questions I'm seeing— from coaches, architects, VPs, consultants, solopreneurs— is some version of: "What do I actually ask it to do?" I had it too, so you're not alone! They set it up. They run their first task. Maybe a second. Then they stare at the blinking cursor and wonder if they're doing something wrong. They're not. The bottleneck is inspiration, not technology. Why This...
The Beatitudes of AI
Hi Reader, Blessed are the AI headshot users, for they look younger but their skin also looks weird. Blessed are the AI early adopters, for they shall inherit middle management. Blessed are the AI hack hoarders, for there will always be more to hoard. Blessed are those who say coding is dead, for they don't read spaghetti code. Blessed are those who use AI for cold outreach, for theirs is the trash can and spam button. Blessed are the AI doomers, for they shall be vindicated...
Why I tell clients to ignore AI memory
Hi Reader, Last week I walked you through moving everything from ChatGPT to Claude. Four steps, everything comes with you. But here’s what I didn’t say— the migration is the easy part. The harder question is where that context should actually live. Someone commented on one of my LinkedIn posts: "ChatGPT’s memory is more reliable than Claude’s." They were right. And that’s exactly the wrong question. I’ve built context systems for a dozen clients this year. The pattern is always the same— the...
How to take everything from ChatGPT
Hi Reader, Quick note— the link to the Cowork Setup Guide in last week’s email was broken. Here’s the working link: Cowork Setup Guide. Apologies for that. People feel stuck in ChatGPT because it "knows them." Custom instructions. Conversation history. Preferences it's picked up over months. Walking away feels like starting over. Here's the thing— that context is portable. All of it. I've migrated a dozen clients this year. The process is the same every time— four steps. Step 1: Extract What...
I let AI do my accounting
Hi Reader, Claude has a mode called Cowork. It works on your desktop while you do other things. Here’s what it handled for me this week— while I was doing the work that only I can do: Fixed my DMARC records to rescue email deliverability Journaled accrual accounting entries (and caught mistakes I’d made) Organized my client project folders Built a new onboarding sequence in Kit, complete with automations Turned sales calls into proposals Cleared my inboxes. Four times. *Who loves figuring out...
72 minutes that might change how you use AI
Hi Reader, I recently did my first ever in-person interview. I sat down with Nathan Barry (founder of kit.com) and went deep for over an hour on AI. We called it The Ultimate AI Masterclass for Businesses in 2026, and honestly, that title earns its name. We get into the most important things you need to be doing right now to get the most out of AI:- context engineering, - workflow design, - the mistakes I see smart operators making every single day.- real examples, - and real systems you can...
I stopped re-explaining myself to AI
Hi Reader, Last week I posted something on LinkedIn about AI skills, and it went a little nuts. The response told me something: people are tired of re-explaining themselves to AI every single conversation. Same voice instructions. Same formatting preferences.Same "no, that's not what I meant" corrections.Same copy-pasting and heavy editing of everything. Every. Single. Time. That's the problem skill files solve. What's a Skill File? A skill file is a markdown document that teaches AI your...
AI gives you hours back. Then what?
Hi Reader, The hunger of our age isn't for more. It's for meaning. We have everything. And we're still starving. Two Kinds of Desire Some desires transform you.Some just distract you. Actually learning something hard rewires your brain.Scrolling leaves you exactly where you started. Both feel like satisfaction.Only one really is. This is the difference between deep desires and shallow ones. Deep desires change who you are. They require struggle. They leave you different than when you started....
I will die on the em dash hill
Hi Reader, A year ago, LinkedIn declared war on the em dash. For the record, I love the em dash. I will forever be waving the flag of the em dash. If there was an em dash brand, I'd buy all their stuff. I will never let it go. I will never give it up. Em dashes are the best. *ahem* Back to the war. Everyone said the em dash was an "AI tell." And it still is. But there's a bigger boogieman out to get you. The Real Pattern Look at these sentences: • "It's not about productivity. It's about...
Weekly AI strategies to reclaim 15+ hours/week— without sounding like a robot. Real systems. Real results. Your voice intact. Join 14,000+ founders.