Bill Perkins: Early Career & Path to Success, Youth vs. Net Worth, Trading Philosophy | Ep 21 PART 1

We dive into balancing health, wealth, and time, taking massive risks, and snapping off autopilot. Bill Perkins breaks down his million-dollar trading mindset, behind-the-scenes details of his heads-up poker match against Landon Tice, buying Ernie Barnes’ Sugar Shack painting, and why converting money into real life experiences takes practice. 🎙️ LATE REG PODCAST — EPISODE 21 ♠️ Guest: Bill Perkins 🎤 Brian Rast 🎤 Phil Laak Play on Phenom Poker with code: latereg 🔗 Join Phenom Poker: https://play.phenompoker.com/register... __________________________________ 🔗 Follow the Late Reg Podcast: 📸 Instagram → / lateregpodcast 🐦 X (Twitter) → / lateregpodcast 📺 YouTube → / @lateregpodcast ⏱️ CHAPTERS: 0:00 Welcome to Late Reg: Bill Perkins 0:57 Why Bill Perkins Got Addicted to Wake Surfing 7:55 Fitness, Night Surfing & Staying Safe as You Age 10:51 Longevity: Could Bill Perkins Live to 140? 11:52 Would You Give Up Your Wealth to Be 21 Again? 14:41 Die With Zero: Health, Wealth & Time 18:45 The Life Calendar: Making Every Week Count 20:54 Why Bill Perkins Wrote Die With Zero 23:23 Bill Perkins vs. Landon Tice: The Heads-Up Challenge 25:03 Studying Poker, GTO & Exploiting Opponents 32:54 Poker, Trading & Learning at an Elite Level 35:03 Energy Trading, Venture Capital & Building Wealth 38:56 Phenom Poker Break 39:59 Brian Rast’s Brutal Bike Prop Bet 45:04 Bill Perkins’ Biggest Jump in Net Worth 46:34 The Car Crash He Hid From His Mom 49:22 Testosterone, Risk-Taking & Overconfidence 52:44 How Much Money Do You Actually Need to Survive? 56:57 The Moment Bill Realized He Could Stop Working 57:17 Does More Money Really Make You Happier? 59:16 Building the Jupiter Supper Club in Austin 1:03:18 Turning Money Into Fulfillment 1:04:57 Expensive Purchases That Brought No Happiness 1:06:26 Alcohol, Drugs & Avoiding the Wrong Experiences 1:07:46 Lamborghinis, McLarens & Materialism 1:10:02 The Story Behind Bill Perkins’ “Sugar Shack” Painting 1:13:02 Art, Culture & Preserving History 1:15:51 The Wild Auction Battle for “The Sugar Shack” 1:17:43 Why Bill Believes the Painting Is Undervalued 1:20:36 Afroman, Free Speech & “Lemon Pound Cake” 1:23:06 Why Bill Perkins Loves Prop Bets 1:24:13 Using Bets to Push People Beyond Their Limits 1:25:44 Bill’s Own Body-Fat & Discipline Prop Bets 1:28:23 Surviving the Mud at Burning Man 1:30:43 Bill Perkins’ Biggest Financial Losses 1:31:26 Why Traders and Poker Players Need Stoicism 1:32:40 Losing Money, Losing His Job & Starting Over 1:33:29 Building Systems to Stay Off Autopilot 1:35:33 Bill Perkins’ Best Advice for Traders 1:38:10 Connection Issues & Wrapping Up Part One