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Now, for the last 20yrs I've been trying to fix a major weakness in my business skills.
A few weeks ago... I stopped.
My weakness... I’m terrible at managing people. Like really TERRIBLE.
Actually, consistently, for-two-decades terrible. I’ve hired and lost employees, contractors, editors, assistants, and managers across a 20-year career. My best revenue year was $2M with 13 employees, but I was working them and myself to death.
That team is no longer with me. Three weeks ago I was sitting in my office thinking about my brother. He’s my video editor. Great guy. Motivated. Capable of learning. But I’d realized I have set him up to fail because my management style is basically “here’s the task, go figure it out.”
Sink or swim.
No KPIs. No clear outcome statement. No weekly check-ins.
Just me expecting him to deliver. Sound familiar? Surely, I'm not alone here...
I know I’m not alone in this. Bill Bonner of Agora (billion dollar publishing company) famously ran a “sink or swim” management style. No training. You either figure it out and succeed, or you don’t and you’re gone.
I used to admire that approach. Now I realize it only worked because Agora hired copywriters, and copywriting output is binary. The copy either converts or it doesn’t. There’s no ambiguity to manage.
But here’s where my thinking shifted. Instead of asking “how do I become a better manager?” I asked a completely different question...
What if I redesigned my entire business so that my inability to manage people just didn’t matter?
The Self-Awareness Gap Most Entrepreneurs Ignore
We live in a business culture that worships “working on your weaknesses.” Read any business book. Listen to any podcast.
The advice is always the same:
identify your gaps build systems to close them hire people to fill them develop the skills you lack.
That advice assumes your weaknesses are worth fixing. MAJOR KEY = What if fixing weaknesses is fixing the bottom 20% and instead we are supposed to just play to our strengths instead??? 🤔
I refuse to focus on my weaknesses anymore.
Not because I’m lazy.
Not because I haven’t tried.
I’ve read the management books. I’ve hired the coaches. I’ve built the systems. I’ve written hundreds of SOPs. Every single time, the same pattern repeats. I set it up, it runs for a while, my attention drifts to the things I’m actually good at (copywriting, running ads, marketing), the system degrades, and I’m back to square one.
The business advice industry has a blind spot.
It treats every weakness as a skill gap that can be trained away. But some weaknesses are structural. They’re part of how you’re wired. Trying to fix them is like trying to make a fish climb a tree. The fish isn’t broken, the fish is just in the wrong environment.
The real skill isn’t fixing your weaknesses. It’s designing an environment where your weaknesses don’t trigger.
For example, if I'm bad at video editing, why not build a newsletter business instead. No videos necessary.
Sounds easy. I bet you're excited. But how do you accurately pinpoint your weaknesses... your strengths... and STRATEGICALLY choose a business model that fits better than OJ Simpson's glove?
For the first time in history we have a tool (AI) that can solve this for solo operators and small startups.
And I'm going to give you the exact 5 exercises and the prompts I used.
Enter AI Thought Partnering (It Changes Everything)
Here’s where I need to introduce a concept that very few people are talking about yet. Everyone knows AI can write your emails. Draft your blog posts. Generate social media content. That’s AI as a tool. You give it a task, it executes.
AI thought partnering is a fundamentally different way of using AI.
And it's sweeping the nation!
Fortune 500 CEO's are starting to do this...
“AI shouldn't be something you just 'follow'—it's a partnership. To really excel today, you need a thought partner. You need a system that can help you process information and logic more effectively than you can alone.”
-- Ray Dalio (Founder, Bridgewater Associates)
Thought partnering is when you use AI as a strategic collaborator to pressure-test your thinking, challenge your assumptions, and stress-test major decisions before you commit to them.
You’re not asking it to do a task. You’re asking it to raise your level of thinking.
Here’s how it works...
You start by importing as much context about yourself and your business as you can. This means creating a folder with your sales pages, marketing emails, customer personas, SOPs, transcripts of interviews you've been on. You need to feed the AI information about you, your business, your customers, and your market.
Then you bring a real strategic question to the conversation.
Something like “should I restructure my entire business?” or “should I eliminate this revenue channel?”
But you don't stop there, you ask it to run you through rigorous decision frameworks, one at a time, while you challenge and refine the analysis together.
The key word is “together.”
This isn’t “ask ChatGPT a question and do what ChatGPT says.” This is a multi-hour strategic session where you push back on the AI’s analysis, correct its assumptions with real-world data, and force it to recalibrate based on your input.
The AI brings frameworks, structure, and the ability to hold enormous amounts of context simultaneously. You bring your years of domain expertise and the ground truth that no model has access to.
The result? Decisions that are both rigorously analyzed AND grounded in reality.
I just did this for the biggest strategic decision of my career. And the output was a 30-page Threat Resistance Manual that documents every risk, every mitigation strategy, every structural decision, and the complete operating model for my business going forward.
And it's based on frameworks that are taught to Wharton MBA's.
It’s good enough to hand to my wife and say “this is why the business is changing and here’s how we’re protected.”
No consultant could have done this in a single evening. No advisor has the patience to let me challenge every point and recalibrate in real time. No human would sit with me for hours running five different strategic frameworks and updating a living document after each one.
AI did all of that. And it cost me $0 in consulting or coaching.
The 5 Exercises That Bulletproof Business Decisions
Let me walk you through the exact process.
I did not invent these frameworks, neither did AI. McKinsey consultants, Harvard professors, and Fortune 500 strategists use them every day. These are the kid of frameworks and thinking models they teach you in MBA classes.
The new part is that you can now run all five in a single evening with AI.
Exercise 1: The Pre-Mortem (Gary Klein Method)
You project forward one year and assume the decision has failed. Then you identify every plausible failure mode. Not the optimistic version. The honest one. What went wrong? Why did this blow up?
For my decision to eliminate YouTube and go writing-only, the pre-mortem surfaced five risks: writing fatigue, audience ceiling, competitor video threat, relationship depth, and single point of failure. Each one a very real threat to my success.
Then comes the critical step most people skip: you challenge each risk with your actual plans and counterarguments (if you have them). The AI updates its analysis based on your own assessments of the risks it brought forward.
After three rounds of challenge and response, four of my five risks were fully resolved and one was mitigated to “acceptable.” Now, I have a real plan, not just an emotion-fueled idea.
Exercise 2: SWOT Analysis
Standard SWOT. After the AI presents the initial analysis, you challenge any items you think are overstated or miscategorized. Then it recalibrates. Then you challenge again.
My initial SWOT had four weaknesses and four threats. After two rounds of challenge, it dropped to two weaknesses and two threats. Not because I argued them away, but because I had specific counterstrategies the AI hadn’t considered.
Exercise 3: Opportunity Cost Calculation
This is the one that puts real dollar figures on the decision. What are you giving up? What are you gaining? Be honest about the value of what you’re cutting. Don’t lowball the rejected path to make yourself feel good.
My first-pass calculation overvalued what I was walking away from because the AI assumed my YouTube audience (8,400 subscribers) was unique. I corrected it: most of those subscribers are already on my email list and Twitter. The actual unique revenue at risk dropped from $150K-$350K to $30K-$75K. While the recalculated net gain was $520K+ per year.
Exercise 4: Bezos Regret Minimization Framework
You project to age 80 and ask which path produces sharper regret. The critical rule: the path you’re rejecting must be shown in its BEST possible version, not the pessimistic one.
Ai (Claude) showed me a world where YouTube worked perfectly: 150,000 subscribers, $4-5M revenue, brand recognition. Was I really ready to pass that up? Should I dig in deeper and just learn???
Even against that best case, the writing-only path still won for reasons specific to my life (Diaconate formation classes, family time, structural freedom).
Exercise 5: The Reversibility Test
How reversible is the decision? What’s permanently lost? What can be recovered later? Is there an asymmetry between the two paths?
Through this exercise I found that both YouTube educational content and written content compound through search over time.
What Came Out the Other Side
After running all five exercises, I had something I’ve never had before for a major business decision... documented confidence.
Not gut-feel confidence. Not “I asked in an FB group” confidence. A 30-page document that captures every risk I could identify, how each one is handled, the complete operating model, the technology stack, the revenue architecture, and the profit margins in a plain-language summary my wife can read.
The decision? I’m restructuring all 3 of my companies as Zeropreneur business models that rely fully on written content. No employees. No video production. No YouTube channel. AI agents handle every operational role a team used to fill.
My entire job is writing, running ads, and reviewing agent outputs. Home for dinner every night. Not because I set a boundary. Because the business doesn’t require me to be anywhere else.
Could I have reached this decision without AI thought partnering? Sure, but how long? Would I have been too emotional? Would I have thought of every risk or held all the possible outcomes in my mind at the same time?
After months of going back and forth, talking to advisors who each have their own biases, and losing sleep over whether I was making the right call.
I did it in one evening.
Here are the exact prompts I used and the instructions for using them correctly. These are MEGA prompts, they are designed to dig far below the shallow layer and get to the real heart of your issues.
There's a bonus prompt included as well, that helps you find the highest leverage marketing strategy you should be doing more often.
These aren't "easy" prompts. You'll be answering tough personal questions and it's going to hold you accountable.
If you'll use both of these tonight, I promise you'll be thanking me tomorrow. These two prompts changed my entire business for the better, mentally and financially.
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