90 % of AI users leave it’s real value on the table, that the uncomfortable truth
Most founders are using AI like an expensive intern—writing emails, summarizing documents, generating social posts. While this is all good and productive, a small group of people are using it completely differently. And the gap in strategic advantages is widening every week.
Here’s what I’m seeing: The ROI of AI isn’t in the 30 minutes you save writing content. It’s in the 50K mistake you avoid because AI helped you see you were solving the wrong problem.
I spent the last month documenting how strategic founders actually use AI—not for task automation, but for strategic thinking. The pattern is clear across 10 different scenarios, from tax planning to pricing strategy to hiring decisions.
The difference comes down to how you prompt.
Generic: “What are common tax deductions for small business owners?” Strategic: “Challenge my assumption that S-Corp incorporation is right for my $180K sole proprietorship. What are three scenarios where staying solo is smarter given my 18-month hiring plan?”
One gives you a list you could Google. The other reveals entity structure timing insights worth $15K-30K annually.
Generic: “How should I price my product?”
Strategic: “I charge $99/month flat with 8% monthly churn. Customers range from 5 to 50-person teams. What does my churn rate reveal? Is this a pricing structure issue or a value delivery problem?”
One gives you tactics. The other helps you realize you’re capturing the wrong customers entirely—you’re too cheap for enterprise buyers who’d stay, too expensive for SMBs who churn.
Here’s the pattern in every strategic prompt:
-Rich context with specific numbers and constraints
-Explicit challenge to your core assumption
-Request for diagnosis, not just solutions
-Scenario planning for multiple possible futures
This transforms AI from a content generator into a strategic thinking partner.
I’ve mapped out 10 scenarios where this approach changes everything: personal tax planning, asset allocation, inventory management, marketing strategy, pricing, website conversion, cash flow, hiring, and growth positioning. A short description is given in the carousel
The founders winning with AI aren’t using it to work faster. They’re using it to think better. And that’s an unfair advantage that compounds monthly.
Swipe through the carousel to see all 10 scenarios. I’ll be breaking down each one in detail over the next few weeks.
Now what’s one strategic decision you’re facing where you’d benefit from someone challenging your thinking—not just executing your plan?
Drop it below. Let’s explore how the right prompt could reframe it.
