In this episode, Simon Cockram sits down with Jack Harrison, an ultra-endurance athlete from York, United Kingdom, who has tested his limits across an incredible 15 different disciplines. Unlike many athletes who specialise in one sport, Jack has competed in ultramarathons, Ironmans, marathon swims, long-distance cycling, sailing across seas, and even summiting some of the world’s highest peaks. His journey combines adventure, resilience, and an unstoppable drive to see how far the human body can really go. Jack shares powerful insights into the mindset required for ultra-endurance challenges—how to deal with pain, manage recovery, and harness curiosity as fuel to keep pushing forward. We dive into the lessons he’s learned from competing in some of the toughest events on the planet, including why understanding your muscles vs tendons matters, how to manage injuries, and the importance of balancing strength, endurance, and mental resilience.

With over 80 countries travelled, Jack also reflects on the beauty of racing in extraordinary locations, from skiing in Lapland to running on the Great Wall of China. This conversation is packed with motivation, mindset tools, and practical advice for runners, triathletes, and anyone drawn to testing their limits.

Chapters

00:00 – Why Endurance? Sport lessons that carry into life

04:00 – Type-2 Fun: discomfort now, reward later

08:00 – Raising Your Ceiling: unlocking new mental “levels”

12:00 – What the Finish Gives You: fulfillment vs immediate gratification

16:00 – Curiosity & Limits: why we seek the edge

20:00 – Multisport Approach: snow, water, land (and why)

24:00 – Training the Common Denominators: cardio + S&C + specific skill

28:00 – Running vs Cycling: impact, injuries, smart progression

32:00 – Load–Capacity Model: how to push without breaking

36:00 – Zone Training 101: using Zone 2 and avoiding the bonk

40:00 – Fueling in the Real World: supported vs unsupported

44:00 – Mind Games: breaking ultras into tiny wins

48:00 – Solitude & Headspace: 10 hours alone with your thoughts

52:00 – Expectation Setting: choosing hardship on purpose

56:00 – Pacing the Red Mist: managing the race-start adrenaline

01:00:00 – From Kid Racer to Adult Adventurer: shifting from perfection to enjoyment

01:04:00 – Niche endurance races: skiing, ice skating & Lapland

01:08:00 – Calf injuries, running setbacks & learning to adapt

01:12:00 – Muscles vs tendons: recovery, resilience & training age

01:16:00 – Next challenge: 24-hour solo swim (1 mile every hour)

01:20:00 – Why do this? Type-2 fun, curiosity & personal growth

01:24:00 – Writing the lessons: book ideas & stories from races

01:28:00 – Where to find more: World’s Hardest Endurance Races book & next steps

In this episode, Simon Cockram sits down with Matthew Stafford to explore the power of networks, the journey into venture capital, and what really makes founders and businesses succeed. Matthew shares how, despite leaving school with poor grades, he hustled through early jobs, discovered tech during the Y2K boom, and eventually transformed his career with a computer science degree at Durham University—proving it’s never too late to reinvent yourself. His path through consulting, an MBA, and into early-stage investing reveals valuable lessons about grit, persistence, and taking chances.

We dive into the creation of Nine Others, Matthew’s global network of curated dinners that have brought entrepreneurs together in over 50 cities since 2011. He explains why a “give-first” mindset, safe spaces, and accountability are key to meaningful connections, and why playing the long game in relationships beats short-term transactions.

From pitching basics to the reality of venture capital, Matthew breaks down what separates successful founders from those who fail, including the idea of “with or without you” energy. He also shares insights from his investments, including Unplugged’s digital detox cabins, and reflects on why the best opportunities often look obscure before they become obvious.

Chapters 00:00 – Why networking matters (from a reluctant networker)

04:00 – Business school lesson: “your network is your net worth” (reframed)

08:00 – Nine Others origin: small, curated dinners since 2011

12:00 – Give-first mindset: be helpful, connect, share generously

16:00 – Play the long game: relationships over transactions

20:00 – Designing safer rooms: rules, vulnerability, real challenges

24:00 – From investor dinners to founder circles: the aha moment

28:00 – Scaling to 50+ cities: community before “startup hubs”

32:00 – Common founder problems: money, people, communication

36:00 – Funding options and targeting the right investors

40:00 – Great pitch basics: keep it short, simple, get the meeting

44:00 – Relationship-first investing: truth, timelines, and trust

48:00 – School results, early jobs & first hustles

52:00 – John Lewis to Y2K: landing RBS IT role

56:00 – Learning tech on the job; consulting at Bank of New York

01:00:00 – Back to uni at 27: Durham CS degree, transformation

01:04:00 – Post-degree restlessness; MBA and discovering venture capital

01:08:00 – First early-stage investor role; portfolio math and exits

01:12:00 – Picking winners: grit, “with/without you” energy, Tesla lens; Unplugged case; wrap-up & contact info

In this powerful and wide-ranging conversation, Simon Cockram and Merlin Matthews dive deep into what it means to be a man in 2025. From fatherhood and role models to brotherhood and purpose, this episode explores the challenges men face today—and the opportunities for growth, strength, and connection. We begin by unpacking how traditional male roles have shifted and why so many men are struggling with isolation, silence, and the pressure to “go it alone.”

We discuss the missing rites of passage that once helped boys become men, and how modern substitutes—from gangs to the military—often provide structure without true support. The conversation turns to mental health, with an honest look at the male suicide crisis and the lack of spaces for men to share openly. We explore how men can replace shallow pub talk with real, vulnerable conversations—and why accountability, brotherhood, and coaching are so essential to thriving. From there, we dig into focus and goals. Why having more than three goals often leads to overwhelm, and how consistency, compounding, and long-term thinking unlock real transformation. We talk about regrets, the “future self” test, and why it’s always the things left untried that haunt us later in life. In one of the most personal parts of the episode, I share my dream of DJing hard techno to a live crowd—something I know I’ll regret if I don’t pursue. We break down the fears of age, failure, and even success, and how pursuing your passion sets a powerful example for your kids.

We finish with the importance of strength training, belonging, and purpose—not just for health today but for longevity and vitality tomorrow. This episode is about men, meaning, and movement—taking action, finding brotherhood, and living without regret.

Chapters 00:00 – Intro: Men in 2025 & shifting roles

04:00 – Fathers as role models: traits to keep vs reject

08:00 – Conditioning programming & the “lone warrior” script

12:00 – Male suicide crisis, men’s circles and support orgs

16:00 – Missing male presence: mentors, sport & rites of passage

20:00 – Initiation stories; “boys in man suits” & the loss of elders

24:00 – Modern initiation (gangs/military) & power under control

28:00 – Women’s daily support vs men’s silence; sharing struggles

32:00 – New-dad example: support gap & rebuilding community

36:00 – Coffee vs beers, ego, shallow chat; purpose after work, retirement

40:00 – Talking feelings without fixing stigma & real check-ins

44:00 – Accountability, brotherhood and going farther together

48:00 – Why three goals: focus, overwhelm & action over consumption

52:00 – Implement what you read: mentors, doing knowing, consistency

56:00 – 10-year thinking, compounding gains & choosing where to spend an hour

01:00:00 – Plan cascade, “gain vs gap”, Who Not How, 10x vs 2x, BHAGs

01:04:00 – Purpose over money; future-self & rocking-chair test; regrets of inaction

01:08:00 – Declaring the DJ dream; age fears; who’s stopping you; make a plan

01:12:00 – Role-modelling for kids; Blue Zones: purpose, belonging, exercise; lift for life

01:16:00 – Why people skip training; comfort culture; go with a crew; wrap-up & how to join Man Academy