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.
15 months from 'last resort' to reality
Hi Reader, ChatGPT knows your questions, fears, and half-formed ideas. The career doubts you'd never say out loud. That weird rash you asked it about. The things you don't speak aloud. And now they're selling ads against it. The "Last Resort" That Took 15 Months Sam Altman, October 2024:"Ads are like a last resort for us as a business model." Sam Altman, January 2026:"We are starting to test ads in ChatGPT." X posts of Sam Altman in 2024 and 2025 talking about ads Fifteen months from "last...
I'm betting on Claude. Here's why.
Hi Reader, For years I said "use whatever AI works for you." ChatGPT, Claude, Gemini—pick one and go. This week, I stopped saying that. The Fork is Real The gap between AI tools is widening fast. Not in features. In actual business capabilities. Claude is shipping things that matter for real work: Claude Code (AI that actually writes and edits code) Claude Cowork (launched this week—Claude Code for non-coders) Computer use, file organization, data analysis ChatGPT is still a great personal...
Nobody noticed you were gone
Hi Reader,You come and go on social.You send a newsletter, then you don't.The world keeps spinning. The apology post is a trap.So is the "I know it's been a while since I sent one of these" email opener. Nobody was counting the days.They didn't notice. That sounds brutal.It's actually a gift. The Permission Slip You don't owe anyone an explanation. You don't need to start with "I know it's been a while..."You don't need to promise to be more consistent.You don't need permission to show up....
Everyone's building AI agents. Most are building the wrong thing
Hi Reader, Everyone’s talking about “AI agents” right now. But most people are confused about where automation stops and agents begin. Here’s the truth: they’re not as distinct as the charts make them seem. Automation: If this happens, do that. Boolean logic. Predefined rules. Fast, reliable, but rigid. AI automation: Same structure, but now you’re calling an LLM for one or more steps. Still deterministic overall, but with flexibility where you need it. AI agent: Non-deterministic. Adaptive....
Why your prompts fail — and the Meta Prompt that fixes it
Hi Reader, Save this (you’ll use it weekly). The right prompt is like magic. It gets you dependable results every time. It takes the frustration out of the creation process. It’s the foundation of a rock solid and repeatable workflow. But here’s the thing: A prompt needs to be custom to your task. So most copy-and-paste prompts aren’t valuable. Instead, you need to learn the Meta Prompt™. What it is: AI knows how to use AI better than people. Meta Prompting is using AI to create your prompt...
Is your ChatGPT memory working against you?
Hi Reader, ChatGPT has a hidden unlock that most people don’t know about. It’s called Project memory control. And it solves one of the biggest frustrations with using AI for multiple things: the messy, tangled memory that bleeds into everything. The Problem with a Shared Brain Memory is nice. It gives AI context so you don’t have to repeat yourself. But it’s messy. It remembers that one-off search you did for a gift and thinks it’s your new career path. It mixes the feedback from a client...
Scrooge McDucking in content gold 💰 (prompt inside)
Hi Reader, I’ve always struggled to post consistently. For the longest time, I thought it was just me being lazy. Or perfectionist. Or not having anything valuable to say. But I found an unlock that changed everything. The Struggle Was Real I still get all up in my head. I feel like I don’t have anything to say. Get frustrated when posts don’t perform. Sound familiar? Here’s what I didn’t realize: I was suffering from Content Blindness. Every day, I was having brilliant conversations. Solving...
ChatGPT and OnlyFans: Same business model (seriously)
Hi Reader, "Your tone is reasonable and logical. You presented clear facts and maintained professionalism throughout. The other party's response is erratic and unreasonable by comparison." Yessssss. What a relief. I was drowning in a contract disagreement. Emails back and forth for days. Getting nowhere. The kind of business friction that makes you question your sanity. So I threw the conversation thread at ChatGPT. "Analyze my tone," I said. And there it was. Digital validation. My AI...
5 words that fix bad AI (seriously)
Hi Reader, It only takes 5 words. That's all. Five simple words to transform AI from a frustrating waste of time into the thinking partner you actually need. The Problem Every Founder Faces I work with founders daily in my AI cohort and custom services. And I hear the same complaint over and over: "AI isn't that useful to us.""AI gives me garbage.""I spend more time fixing AI output than if I just did it myself." Sound familiar? You're not alone. And you're definitely not doing anything...
GPT-5 is driving everyone nuts (here's the fix)
Hi Reader, GPT-5 is driving everyone nuts. And honestly? I get it. Here's what happened & how to fix it: The Puppet Master Problem OpenAI is playing puppet master with something they call "model switching." They decide which model you get.Not you.Never you. Their logic sounds reasonable on the surface: "We'll make it easier on users by automatically selecting the best model for each task." The reality? It's a flaming pile of inconsistency that's making smart people feel like they're losing...
Weekly AI strategies to reclaim 15+ hours/week— without sounding like a robot. Real systems. Real results. Your voice intact. Join 14,000+ founders.