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.
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...
Letting go is harder than you think
Hi Reader, Six+ months ago, I moved my family of 5 from Seattle to Mexico. That was the easy part. We packed up our belongings, And came with just 1 suitcases + carry ons. Stepped into the unknown: A city we’d never even visited. A school we hadn’t seen. A climate that we’d never lived in. A language we barely spoke. (Hello Duolingo! 😅) Everyone asks “why?” But the better question is “why not?” Why keep doing the same thing if it’s not lighting you up? Here’s what nobody tells you about...
I'm selling a house to bet on myself (again)
Hi Reader, I have news. I'm selling a house to spend $140,000 to grow my business this year.Last time I bet big, I lost everything. The target is a $500k run rate. I know. It's a lot of 0's. This is the biggest single investment I've ever made in myself. I'm terrified.And excited. But here's the story: (If you're following close enough, you can put together the pieces on your own.So I may as well spill the beans.) Last year's gross was just about $250k.Most of it wasn't recurring.Much of it...
My Unexpected Ally in the Quest for Meaning
👋 Hi! I'm Dan. I help entrepreneurs and creatives find the clarity and motivation to get their work out into the world. If that sounds good, let's go! 🚀 Hi Reader, I hope this finds you well! Great things ahead for today's issue: ✅ Lesson's Learned: an essay on the return of humanity to work🤖 An update on the AI Mastery Cohort❤️ A sponsor🎉 My favorite things (plus a big milestone) Let's get into it! ✅ Lesson's LearnedThe Generalist's Moment: AI and the Return of Human Work All my life, I've...
Weekly AI strategies to reclaim 15+ hours/week— without sounding like a robot. Real systems. Real results. Your voice intact. Join 14,000+ founders.