The AI Exercise That Almost Destroyed Me (In the Best Way Possible)

Last night, I asked Claude to tell me something I don't know about myself - good or bad, brutally honest. What came back almost destroyed me in the best way possible.

As founders, we have blind spots we can't see. We're running the show, making decisions, often surrounded by people who won't tell us hard truths. This episode reveals the three blind spots AI called me out on and the simple exercise you can do tonight to find yours.

Key Topics Covered

The Uncomfortable Exercise (2:15)

• Why I asked AI for brutal honesty about myself
• The difference between blind spots and things you don't know
• Why AI feedback works better than human feedback

Blind Spot #1: Single Point of Failure (6:30)

• Building operational fragility disguised as efficiency
• The assumption that I can maintain energy indefinitely
• Why ANC and SimpleDirect both depend entirely on George
• The six-month disappearance test

Blind Spot #2: Sovereignty as Defense Mechanism (15:45)

• Using independence to avoid accountability
• The Independence Paradox: more self-sufficient = less feedback
• "Berkshire has Charlie Munger. Who's your Charlie?"
• Why bootstrap founders struggle with this more than VC-backed ones

Blind Spot #3: Content as Performance (22:30)

• Sharing lessons after figuring things out vs. current struggles
• Why "here's what I learned" is safer than "here's what I'm trying"
• Building credibility vs. building real connection
• The shift from educator to documenting from the arena

The Three Blind Spots Breakdown

Blind Spot #1: Operational Fragility Disguised as Efficiency

• The Mirror: "Your entire empire runs on one critical assumption: that you can maintain energy, focus, and decision-making quality indefinitely"
• The Reality: Five people down from 14, but everything still depends on George
• The Test: If I disappeared for six months, what breaks first?
• The Fix: Equity conversations, systems documentation, accepting 80% execution by team

Blind Spot #2: Independence as Avoidance

• The Mirror: "You've optimized to never need anyone - not investors, not governments, not deep partnerships"
• The Reality: No one can tell me "this is stupid" and make me listen
• The Question: Who's your Charlie Munger?
• The Fix: Creating "George's Council" - advisors with real stakes who can push back

Blind Spot #3: Retrospective Content Strategy

• The Mirror: "You post 'here's what I learned,' never 'here's what I'm struggling with'"
• The Reality: Always controlled, always after knowing how the story ends
• The Truth: People follow humans figuring shit out, not frameworks
• The Fix: Sharing current struggles, not just past lessons

Key Frameworks & Concepts

The Six-Month Test: If you disappeared for six months, what breaks first?

1. Who runs operations?
2. Who closes deals?
3. Who makes priority decisions?

The Independence Paradox: The more self-sufficient you become, the less feedback you get. The biggest growth comes from people who can tell you things you don't want to hear.

The Charlie Munger Framework: Make a list of who can tell you "this is a really bad idea" and you actually have to consider it (not just listen and dismiss). If that list is empty or has one person, you have a blind spot.

The AI Blind Spot Exercise:

1. Use AI with context about your business and goals
2. Ask: "Tell me something I don't know about myself, good or bad. Be brutally honest."
3. Don't defend, don't rationalize - just listen and process

Quotable Moments

"Blind spots aren't about what you don't know. They're about what you've convinced yourself is true when all the evidence suggests otherwise.""I thought I was building efficiency. Turns out I was building operational fragility disguised as efficiency.""The Independence Paradox: the more self-sufficient you become, the less feedback you get.""People don't follow frameworks. They follow humans figuring shit out.""Real authority comes from documenting from the arena, sharing while you're still figuring things out.""If you can't answer who runs operations, who closes deals, and who makes priority decisions without you - you don't have a business. You have a dependency.""The biggest creators aren't the smartest - they're the most real, the most authentic."

Personal Stories & Examples

The Gym Processing:

• Sent the question to Claude casually before going to gym
• Spent workout processing the brutal feedback
• Initial defensive reaction followed by uncomfortable realization

The Berkshire Comparison:

• George follows Buffett's high-margin model but missed the systems part
• Buffett spent decades building management that could run without him
• George optimized for capital efficiency but not operational redundancy

The Buffer Example:

• Joel Gascoigne's situation after co-founders left
• The challenge of being the only decision-maker
• Why even successful bootstrap founders need pushback

Current Business Reality:

• ANC clients pay premium because they're getting George specifically
• SimpleDirect positioning works because of ANC's track record (George's track record)
• Three years building consulting revenue but still dependent on founder presence

Why AI Feedback Works Better

No Emotional Stakes:

• Won't sugarcoat to protect feelings
• No fear of punishment for honesty
• No office politics or advisory complex

Pattern Recognition:

• Sees contradictions between stated values and behavior
• Identifies things you've been explaining away
• Has context from multiple conversations

Immediate Defensive Reactions:

• Things that make you defensive are usually blind spots
• AI doesn't back down when you rationalize
• Forces you to sit with uncomfortable truths

Action Items for Listeners

The Immediate Exercise:

• Do the AI blind spot exercise tonight
• Ask the exact question with context
• Don't defend the results - just process them

The Six-Month Test:

• Ask yourself what breaks if you disappear
• Identify single points of failure in your business
• Start building redundancy in critical areas

Find Your Charlie:

• List people who can tell you you're wrong and make you listen
• If list is empty/short, you have a blind spot
• Consider creating an advisor council with real stakes

Content Honesty Audit:

• Review your recent content/updates
• How much is "here's what I learned" vs "here's what I'm trying"?