The Problem With Being Your Business: James Haskell

James Haskell joins James Smith for a brutally honest conversation about life after professional sport, the chaos of building multiple businesses, and what it actually takes to stay relevant when the game is over. A former England rugby star, Sunday Times bestselling author, and DJ, Haskell pulls no punches on the mental cost of reinvention — and why his obsession with performing has never really left him. 👁️ Try Neutonic: https://www.neutonic.com/jamessmith 🧪 Check your Test: https://www.manual.co/smith 📝 Business Mentoring: https://www.jamessmith.business 🏋🏼‍♂️ Online Coaching: https://www.jamessmithacademy.com James Haskell on Instagram – https://www.instagram.com/jameshaskell James Haskell's music – https://open.spotify.com/artist/5ry5gHsT7l1X84yGPZeVIj The Good, The Bad & The Rugby – https://open.spotify.com/show/1LJJ9KUF4aAjcSPimyKfp3 James opens up about the fear of failure that drove him through rugby, the strange emptiness that follows success, and why 40 felt like the moment everything had to change. From DJing in a music industry that doesn't return emails, to launching Black Eye Gin with a £1.50-per-bottle charity model, to finally getting his testosterone tested — this one covers ground most people won't. He covers: ◼️ Why being your own business is feast or famine — and how to future-proof it ◼️ The DJ career no one takes seriously (yet) ◼️ Building undeniable proof against self-doubt ◼️ Why catastrophising your future can be a legitimate motivational tool ◼️ What testosterone at level 3 actually feels like — and what TRT changed ◼️ The email list gap that's costing him (and you) real money Chapters: 00:00 There Are a Lot of Lost Men Out There 01:23 The Problem With Being Your Own Business 03:22 Life After Rugby — Planning vs Panic 05:05 Finding What You Actually Want to Do 05:30 The DJ Career: 12 Years, 31 Records 07:22 MMA, Surgeries and the Body Paying the Price 09:24 Going Back to Basics in 2026 10:18 Why Haskell Got Into DJing 12:01 Building Undeniable Proof Against Self-Doubt 13:31 Imposter Syndrome, Evidence Bases and Therapy at 17 15:35 Creating Common Enemies as Motivation 18:06 Catastrophising as a Motivational Mechanism 18:44 Defining What Success Actually Looks Like 19:21 Why Very Wealthy Men Lose Their Money 20:01 The Rocky Montage Years: Fear of Failure as Fuel 20:52 Learning to Sit In the Moment 22:00 The Music Industry Is a Wild West Shambles 24:50 The 50 Cent Tour Story — Music vs Every Other Business 27:03 Drug Culture, Harm Reduction and the Honest Conversation 30:49 What He'd Tell His Daughter About Drugs 32:02 Social Media, Innocence and Raising Kids Today 33:39 Does Civilisation Correct Itself? 35:40 On Politics, Reform and Weak Leaders 37:13 Hair Transplants, Prince William and Shaving Your Head 39:14 The James Haskell Effect on Rugby Back Rows 41:47 Henry Pollock, Pranks and the England Camp 44:03 The Witch Teeth Prank at the Dentist 45:24 The 2007 World Cup — and Ronny Ring's Band of Brothers Moment 49:01 Maidenhead RFC, Getting Dropped and a Mate's Game of His Life 53:41 Black Eye Gin — The Charity, the Recipe and the Origin 57:06 Rugby, UFC and Sports That Don't Apologise for Themselves 59:55 Trying Neutonic for the First Time 01:01:05 Building an Event That Combines Sport, Music and Fitness 01:07:19 Peptides, BPC-157 and Healing a Torn Bicep 01:09:05 Testosterone at Level 3 — Getting on TRT 01:20:32 The Relevancy Trap and Running Active Businesses 01:22:38 The Infinity Pool Story — Getting the Balance Right 01:26:36 Why Haskell Doesn't Have an Email List (Yet) 01:27:46 The Email Marketing Masterclass He Didn't Ask For 01:37:57 What's Coming Next: Music, DJ Gigs and the Tequila Launch This is one of those conversations that goes everywhere — rugby war stories, music industry chaos, drug policy, fatherhood, hormones, hair transplants, and the uncomfortable truth that being very good at performing doesn't automatically make you good at business. Haskell is funnier, more self-aware, and more switched-on than most people give him credit for — and this is the version of him you don't usually get to see. Learn more about your ad choices. Visit megaphone.fm/adchoices