How different would your life look today if you stopped preparing for “good enough” and started preparing for “extraordinary”?

In this conversation, entrepreneur, investor, author, and extreme-preparation evangelist Randall Kaplan opens up about the surprisingly painful origins of his work ethic: childhood bullying, a debilitating stutter, and a long journey toward becoming a clear, confident communicator.

Randall shares the exact mental frameworks he used to transform his life — from landing a book deal through a cold email, to becoming a TED speaker, to interviewing some of the world’s most accomplished leaders on his podcast.

We explore extreme preparation, the habits that separate average performers from exceptional ones, and why “no” is often just the beginning of the road to “yes.”

Timestamps:

00:00 — The question that opens every interview: “Who are you?”

02:00 — How photography and beaches shaped Randall’s creative identity

04:30 — Building Sandee: cataloging 100,000+ beaches around the world

06:15 — How a cold email landed Randall a book deal

08:00 — Childhood bullying, stuttering, and the start of extreme preparation

10:30 — The breakthrough moment at the McDonald’s drive-thru

14:00 — How speech therapy reprogrammed his mind and confidence

15:30 — The emotional weight and triumph of giving a TED Talk

17:00 — Studying the top TED Talks and dissecting what works

19:00 — Cutting a 70-minute keynote into 18 minutes

21:15 — Why the painful story had to stay in the talk

22:00 — The team behind the TED Talk: coaches, comedians, voice experts

26:00 — The Roger Love experience and knowing when not to change

28:00 — The balance between outside coaching and trusting your intuition

30:00 — Extreme preparation in interviewing: The EPT “torpedo question”

32:00 — Why most people aren’t prepared — and how to stand out instantly

35:00 — Randall’s research process: thousands of pages, distilled

37:00 — “If you’re early, you’re on time; if you’re on time, you’re late.”

38:00 — When life derails your plans: broken schedules and mental resets

40:00 — Gratitude walks and the 40,000-foot reset

42:00 — Never send an email when angry — Randall’s practice

46:00 — Why AI should assist your preparation, not replace it

47:00 — The small details that cost people opportunities

50:00 — A coaching story: preventing a $3M mistake

52:00 — The doctor who went from zero net worth to $10M in a year

54:00 — The difference between success and stagnation: making a plan

56:00 — Closing wisdom: “Why you must do what no one else does”

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Get your copy of Personal Socrates: Better Questions, Better Life  

Connect with Marc >>> Website | LinkedIn | Instagram |

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A special thanks to our mental fitness + sweat partner Sip Saunas.

🧠  x 🥵 = 😃

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Special props 👇

Music: Clouds - Joakim Karud

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