I Found $180K by Asking the Wrong Question
Bezos used this mental model to build Amazon. I used it to find six figures hiding in a $10M agency's spreadsheets. I'll teach you how to do it with an AI prompt.
The year is 1994. Jeff Bezos had a stable Wall Street job. Good money. Clear path up.
Then he asked himself a weird question.
Not “How do I succeed?” Not “What’s the smart career move?”
He asked: “At age 80, will I regret NOT doing this?”
That’s inversion thinking. Work backward from failure instead of forward from success.
Bezos decided he’d regret not starting Amazon way more than he’d regret leaving Wall Street. So he left. You know how that turned out.
Here’s the thing most people miss about that story.
Bezos didn’t focus on success. He focused on avoiding regret. That’s fundamentally different.
And it’s the same thinking that helped me find $180K in annual revenue leaks for a $10M agency last year. Let me show you how.
The Problem Most Business Owners Don’t See
You’re asking the wrong question.
When revenue is flat or you need growth, what do you ask?
“How do we get more clients?” “What new services should we launch?” “How do we scale faster?”
All forward-looking. All focused on gains.
Meanwhile, money is bleeding out the back door and you don’t even see it because you’re not looking there.
I learned this the hard way working with a PR agency doing $10M in revenue. Three retainers. Team of 30. Looked healthy from the outside.
CEO kept asking me: “How do we grow to $15M?”
I inverted the question: “What’s killing deals right now? Where’s money leaking?”
Found $180K in annual revenue hiding in plain sight.
Here’s what was happening. (And I bet it’s happening in your business too.)
Two retainers were covering expenses for a third retainer that wasn’t optimized. Client paying for work that had nothing to do with their actual business. Money allocated to projects that were basically subsidy for other stuff.
The agency was so focused on signing NEW retainers (gain-seeking) they completely missed the revenue leak in EXISTING retainers (loss-avoidance).
Classic inversion failure.
Charlie Munger (Warren Buffett’s partner for 60 years) has a line I love:
“All I want to know is where I’m going to die so I’ll never go there.” - Charlie Munger
That’s inversion thinking.
Don’t just study success. Study failure. Then avoid it.
Most business owners study competitors who are winning. They read case studies about companies that scaled. They follow the playbook of people ahead of them.
All survivorship bias. You’re only seeing the winners.
Inversion says flip it: Study where businesses like yours DIE. Find the failure modes. Then make sure you never go there.
What the 5% Do Differently
So here’s the inversion framework.
Instead of asking “What should I build?” ask “What’s killing deals right now?”
Instead of “How do we grow revenue?” ask “Where’s revenue leaking?”
Instead of “What’s our competitive advantage?” ask “What would make us irrelevant?”
I worked backward from the agency’s problems.
Started with: Revenue isn’t growing fast enough.
Inverted it: Where is revenue shrinking or leaking that we’re not seeing?
Then I pulled the data. Last 50 client interactions. Support tickets. Churn analysis. Retainer utilization rates.
Pattern emerged immediately: Clients were paying for retainers but only using 60% of allocated hours. The other 40%? Being spent on work unrelated to their business.
That’s $180K annually just evaporating.
Nobody saw it because everyone was asking “How do we sign MORE retainers?” Nobody was asking “Are we optimizing the retainers we HAVE?”
Inversion thinking found it in about 45 minutes.
Here’s where AI makes this a force multiplier.
In the paid section, you’re getting:
The Complete Inversion Analysis Framework - The 4-step process I use to find hidden opportunities in any business
5 Copy-Paste AI Prompts - Exact prompts for analyzing revenue leaks, lost deals, and failure patterns at scale
The Opportunity Scorecard - Decision tree for prioritizing what to fix first (by ROI and complexity)
Real Case Study Breakdown - The full $180K revenue leak story with numbers, timeline, and how we fixed it
Monday Morning Action Plan - One thing you can do this week to find your first leak (30 minutes max)
