Show Notes
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.
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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
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