July 22, 2025

Ryan Bertrand, Fmr Chelsea, Southampton & England: ‘It Didn’t Feel Like the Chelsea I was Brought Up In; The Foundations of Champions League Success' (Ep78)

1 hour 15 minutes

This week, we’re delighted to welcome Ryan Bertrand to the show, the only man to make his Champions League debut in the final…and of course win it in historic style with Chelsea in 2012. The regulars of you will know a conversation like this is exciting for us both as big Chelsea fans, and the shirts we wore throughout gave the game away anyway. But Ryan isn’t just the player who won that cup, played over 260 Premier League games, and was capped 19 times by England.

This is a former athlete with a story to tell that incorporates exploration away from football; interests that fans, the media, even those within the game don’t associate with players. You can do business, learn business, all while playing at the highest level. You can also leverage the power of your network and your unique experiences to add something few others can to businesses outside of the game.

This is something we encourage athletes, the ones who are interested off their own back and the ones who may not have understood the possibilities, to do in a world where opportunity can come from multiple sources. Ryan has built businesses, managed people, and carved out a path that now positions him to succeed at scale. What can you learn from him? It’s the balance of the stories we of course are desperate to hear paired with his transition from player to multi-faceted operator.

On today’s show we discuss:

Football Culture, Clubs & Career Decisions

What Ryan learnt from being around legends like Drogba, Lampard, and Ashley Cole?
What makes a great dressing room character and why every team needs one
What happens when a club loses its “win at all costs” mentality?
Why the best Managers are honest with their players and who was the worst manager he played under
What really goes on during loan deals, and why he cancelled his own loan?
How do directors, signings, and behind-the-scenes agendas shape team selection?

Money, Fame & Mistakes

What’s the financial trap that catches most young players off guard?
Why do so many players go broke despite millionaire contracts?
The mistake that almost cost Ryan his England career
Why did Ryan get into investing and how’s he helping other players now?
What does Ryan think about today’s player brands?

Retirement, Identity & Reinvention

What’s the real emotional toll of retiring from football?
What happens to your identity when you’re no longer “the footballer”?
What advice does he give to younger players about career and legacy?
Why did Ryan refuse to be defined by punditry or football alone?
What would he change about how football prepares players for life after sport?

A huge thank you to our amazing partners on the show:

RUNNA Whether you’re an existing use or if it’s your first time on the app, use the code below for exclusive access! https://join.runna.com/lKmc/redeem?code=BOSRUNNA

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By Charlie & Harry Stebbings

4.1

88 ratings