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” **** Get your copy of Personal Socrates: Better Questions, Better Life   Connect with Marc >>> Website | LinkedIn | Instagram | * A special thanks to our mental fitness + sweat partner Sip Saunas. 🧠  x 🥵 = 😃 * Special props 👇 Music: Clouds - Joakim Karud See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.