What AI Knows About You (That You Don't)

Most of us walk around convinced we know our weaknesses, but what if the thing that knows you better than anyone (your AI assistant) could tell you what you're actually missing? We asked ChatGPT one brutal question and got answers that hit way too close to home.
The uncomfortable truth: we're all playing smaller than we should, carrying more weight than we need to, and missing opportunities hiding in plain sight.
In this episode, we test a viral prompt that reveals your blind spots, squandered potential, and the influence you didn't know you had...then process the existential crisis that follows.

Key Episode Moments:

• The prompt that started it all: "Based on what you know about me, what are my blind spots?"
• Why ChatGPT knows you better than you think (and what that means)
• Jason gets told he's a Ferrari forcing everyone into a school bus
• The "super competent leader tax" — when being good at everything becomes the problem
• Jeremy's revelation: treating creative work as a side hustle instead of the main platform
• Imposter syndrome meets AI: "You're already operating at board level, stop asking permission"
• The technical vs. emotional problem-solving trap most high performers fall into
• Why "playing small" feels safer than taking the big swing
• ChatGPT's productization challenge: you're giving away thousand-dollar consulting for free
• The Taylor Swift wisdom nobody expected: ruin the friendship, take the risk

Timestamps:

• 0:00 The prompt that started everything
• 3:40 Jason's live AI assessment begins
• 6:12 "You're a Ferrari and everyone else is in a school bus"
• 9:01 The imposter syndrome AI detected immediately
• 11:45 Why treating every problem as technical backfires
• 14:27 The IP you're not monetizing (and should be)
• 18:30 Jeremy's gut-punch realization about playing small
• 21:35 How ChatGPT knows you better than you think
• 24:36 Why failure beats decades of "what if"
• 27:00 What to do with this uncomfortable information

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Safety/Disclaimer Note: This episode discusses using AI for self-reflection and personal assessment. Remember that AI tools provide perspective based on patterns in your usage—they're not substitutes for professional coaching, therapy, or mental health support. The hosts are sharing their personal experiences, not providing professional advice.