Mark Devlin is the CEO of Leyton Orient, a team that’s been riding the rollercoaster of English football right on the edge in recent years. From nearly going out of business and dropping into non-league football to bouncing back into League One playoff finals, the fans have been on a ride the few would choose. However, new ownership and big plans to build both on and off the pitch make this London club a hugely exciting football proposition for the next decades.

What has this journey looked like from the inside and how is success being built into the fabric of the future? Having been so close to joining the list that no one wants to be near, alongside Bury, now Morecombe and even Sheffield Wednesday, Orient’s struggles are another glaring reminder of the house of cards an owner financing model presents to the Football League.

Mark is an experienced CEO, leading Brentford through the early years of their ride to Premier League consistency. His take on what is required to build a club for the community and fan while keeping the finance team happy is what sets the O’s apart, and promises big things for a fanbase juggling the mixed emotions of just being happy to still have a football team alongside a want and expectation to win.

On today’s show we discuss:

Recovering from Financial Disaster:

• They story of Leyton Orient's near terminal financial crisis; what happens when a club runs out of money and the owner will no longer cover the losses?
• Relegation to non-league football and the impact falling through the decisions has on a club.
• How do you claw yourself out of a situation like this. The stories are often of disaster, but Leyton Orient have more than recovered in the past few years.
• Are they in a better place now than they were before?

The Value of New Ownership:

• What are the ambitions of new owner David Gandler and why did he decide to buy the club earlier this year?
• Where does the value lie in modern day football?
• What areas of the club need to be developed to both elevate the fan experience and make more money to fund the desired growth?
• What does it take to build a new stadium: from finding a site to financing a project in the hundreds of millions.
• Why this is an opportunity to build something that stretches beyond football; the value of a multi-sport model.

Matching Ambition with Longevity:

• Finding the balance between financial sustainbility and ambition is the hardest part of modern football ownership/management; what is Orient's plan to chase promotion while ensuring the business is safe?
• How much does it cost to get promoted? The crazy finances of the Championship laid bare...
• What did Mark learn from his time in charge of Brentford and applying some of the model they have so successfully been able to implement to reach and thrive and in the Premier League.
• The ambition is to be a sustainable Championship club, but do they dare to look beyond this?

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

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Peter McCormack is the Owner and Chairman of Real Bedford, who play in the 8th tier of English Football. But this is unique for a number of reasons. We always look for the stories that represent a different approach to running sports assets, and building your Premier League ambition around Bitcoin is certainly one of those.

Peter is the host of one of if not the biggest Bitcoin podcasts. As you’ll hear his journey to club ownership is as colourful as it is extraordinary; this is someone who has come through some challenging times to get to where he is now. As you’ve just heard in the intro, everyone laughed at him when he laid out the plan for Real Bedford, but with a wealth of both deep pocketed sponsors and investors, most notably the storied Winklevoss twins (of Olympic rowing, Facebook lawsuit, and Gemini fame to many of you I’m sure), this is quickly becoming a team with both the resources and strategy to fly up the pyramid.

With a women’s team competing in the third tier and proving equally ambitious, the plan is to build a club fully representing the community, full of opportunity and success. The usual challenges remain: success vs profit, full attendances, wider football governance. But as this is a place where we want to look at how to create sustained value beyond football’s historic and increasingly out of date financial levers, the Real Bedford model is a captivating alternative. Not for everyone, not guaranteed to work, and certainly unorthodox, but a bold attempt to break the wheel.

On today’s show we discuss:

Buying a Football Club

• How Peter went from addiction to building a media brand around Bitcoin
• The inside story of how Peter bought Real Bedford FC with podcast money
• How he convinced the Winklevoss twins to back a team in the tenth tier
• Why Real Bedford is run more like a startup than a sports club
• The brutal financial reality of owning a non-league football team
• Why so many lower-league clubs are unsustainable

Brand, Identity & Culture

• Why Real Bedford has a clearer identity than most football clubs
• The value of cult storytelling, local community, and crypto-native branding
• What clubs get wrong about women’s football and how Real Bedford does it differently
• How ambition and relentlessness are what drives the project
• Why does crypto present an opportunity on the financial side of football ownership that traditional approaches miss?

Leadership & Legacy

• What owning a football club taught Peter about management, burnout, and ego
• Why he’s building a club for his kids, not just for wins
• How he thinks about failure and what he’d do differently next time
• "It's not all about winning": Having this approach allows you to recognise success in broader terms, but does it only work at a lower level?

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!
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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