In Season Six of Doing the Opposite: Business Disruptors we’re turning the spotlight onto host of the podcast Jeff Dewing. Jeff is Founder and CEO of Cloudfm Group, keynote speaker, bestselling author, and a leader who rebuilt his life and company by doing the one thing most people fear: the opposite.

In this episode, Jeff and Sam explore what legacy really means to a leader; not as a monument to personal achievement, but as the living proof of the people you’ve empowered to thrive without you. Jeff opens with Turn the Ship Around, the story of a struggling US Navy submarine that became the fleet’s best performer once its new captain stopped granting permission and started demanding intent. The lesson, Jeff argues, translates directly to any organisation: specialists own their craft, and the leader’s job is to provide context and remove friction. 

Jeff traces how grief, reflection, and a Vistage CEO peer group helped him move from instinct to language, from knowing what good culture felt like to being able to articulate it, measure it, and embed it across the business. He shares how, after losing his father in 2017, he made a decision that changed everything: stop being a machine and start trusting the people around him. The result was going from 300 emails a day to three a week. His message to leaders who fear flexible working is blunt: if your people are killing time, the failure is yours, not theirs.

From there, Jeff makes the case for leaving ego at the door. He used to ask his teams to physically remove their shoes before entering a meeting room as a daily reminder that responsibility doesn’t make anyone better than anyone else. He names curiosity as the single most powerful leadership trait: be the last person to speak, ask what others think, and assume everyone in the room knows something you don’t. It’s a habit that keeps him close to people who think completely differently to him, and it’s where most of his learning comes from.

Jeff closes with Ikigai - the Japanese framework that helped him define success not as results, but as fulfilment. When his leadership team debates a hard call and someone asks, “What would Jeff do?” the answer is always the same: he’d ask what you would do. And when Sam gives him the pen and paper to write down the one message he’d send to any young entrepreneur, it takes just five words: It’s not about you.

In 2026 Cloudfm Group celebrates its 15th anniversary. 

Find out more about Cloudfm here.

Hosted by Sam Walker

Watch the podcast on YouTube

Discover Cloudfm Group:

Website  |  LinkedIn

Find the best-selling book Doing The Opposite by Jeff Dewing HERE

In Season Six of Doing the Opposite: Business Disruptors we’re turning the spotlight onto host of the podcast Jeff Dewing. Jeff is Founder and CEO of Cloudfm Group, keynote speaker, bestselling author, and a leader who rebuilt his life and company by doing the one thing most people fear: the opposite. 

In this episode, Jeff and Sam explore what it truly means to do the right thing in business - not as a PR exercise or a tick-box, but as a daily habit that reshapes culture, attracts talent and creates real competitive advantage. Jeff traces his own turning point to 2015, when a childhood memory of two lungs in a pharmacy window, one black, one pink, collided with his love of petrol engines and he could no longer justify the roar of a V8 over the health of the people around him. From that moment, he went fully electric personally and then drove the same shift across the entire Cloudfm fleet.

Jeff unpacks ESG beyond the jargon and brings it to life through the story of CloudFest: a solar-powered event for 250 people that produced just one bin liner of non-recyclable waste. The lesson was simple - it didn’t cost more money, it just required focus. And the pride that followed rippled back into everyday office behaviour, shaping how people saw themselves and the organisation they worked for.

Jeff and Sam consider the cultural pushback on ESG playing out in parts of the world. Jeff’s response is to point to norms that have already shifted permanently: nobody throws litter from a car window or lights a cigarette in a restaurant anymore, not because they were told to stop, but because the culture changed. The same trajectory is possible for ESG. His message to leaders is direct: find someone who cares deeply about it, appoint them, set goals you can measure, and let ethics quietly guide every decision.

In 2026 Cloudfm Group celebrates its 15th anniversary. 

Find out more about Cloudfm here.

Hosted by Sam Walker

Watch the podcast on YouTube

Discover Cloudfm Group:

Website  |  LinkedIn

Find the best-selling book Doing The Opposite by Jeff Dewing HERE

In Season Six of Doing the Opposite: Business Disruptors we’re turning the spotlight onto host of the podcast Jeff Dewing. Jeff is Founder and CEO of Cloudfm Group, keynote speaker, bestselling author, and a leader who rebuilt his life and company by doing the one thing most people fear: the opposite.

What happens when you stop chasing numbers and start solving problems? Jeff and Sam explore why purpose-driven leadership isn’t just a feel-good philosophy but a practical strategy that changed everything at Cloudfm. Drawing on his years in corporate environments where financial targets trumped client outcomes, Jeff explains the moment he decided no one would ever be fired for missing their numbers—and how that single shift unlocked a culture built on honesty and accountability. Using the Carillion collapse as a cautionary tale of what happens when reported performance drifts from reality, he shows why truth has to be baked into the operating system, not bolted on afterwards.

They dig into the hard work behind defining a company purpose, including a gruelling three-day offsite that produced one sentence the entire team could carry: restore trust in a failing industry by changing the rules. Jeff walks through how values—humility, integrity, empathy, and freedom—were given plain-language definitions so they could be lived rather than laminated, and why saying no to misaligned clients protects the system that creates real value. Day to day, it comes down to a single rule on the wall: do the right thing, whatever it costs.

Culture becomes the engine for growth. Jeff shares how listening to detractors instead of removing them lifted employee engagement from around forty percent to eighty-five percent, and why the most engaged company on the planet makes oil in a can. They unpack why engagement must be measured at the manager level, how coaching replaces command-and-control, and what it means to invert the traditional pyramid so frontline teams can act fast for customers. Profit and purpose are not in competition here—profit emerges as the byproduct of solving meaningful problems with integrity and speed.

In 2026 Cloudfm Group celebrates its 15th anniversary. 

Find out more about Cloudfm here.

Hosted by Sam Walker 

Watch the podcast on YouTube

Discover Cloudfm Group:

Website  |  LinkedIn

Find the best-selling book Doing The Opposite by Jeff Dewing HERE

In Season Six of Doing the Opposite: Business Disruptors we’re turning the spotlight onto host of the podcast Jeff Dewing. Jeff is Founder and CEO of Cloudfm Group, keynote speaker, bestselling author, and a leader who rebuilt his life and company by doing the one thing most people fear: the opposite.

What if telling a client “we won’t hit that date” could make them trust you more? Jeff and Sam sit down to pull apart the myth that leaders must project certainty, and show how truth, humility, and well-designed systems can change outcomes. From childhood lessons to boardroom moments, Jeff shows why owning mistakes turns confrontation into collaboration. They dig into the messy middle of transparency: how to be open without creating panic, and how to time information so it helps rather than harms. 

They also flip a common narrative about technology. Instead of using software to polish the story, Jeff built systems that cannot edit, hide, or delete operational data. Raw field notes reach clients untouched, forcing real behaviour change and signalling that nothing is swept under the rug. It’s uncomfortable and powerful, and it turns a platform into a trust engine.  

Jeff also offers practical steps you can use to embed this culture: align your team, practice public ownership of small misses, and design tools that preserve reality. 

In 2026 Cloudfm Group celebrates its 15th anniversary. 

Find out more about Cloudfm here.

Hosted by Sam Walker 

Watch the podcast on YouTube

Discover Cloudfm Group:

Website  |  LinkedIn

Find the best-selling book Doing The Opposite by Jeff Dewing HERE

In Season Six of Doing the Opposite: Business Disruptors we’re turning the spotlight onto host of the podcast Jeff Dewing. Jeff is Founder and CEO of Cloudfm Group, keynote speaker, bestselling author, and a leader who rebuilt his life and company by doing the one thing most people fear: the opposite.

“There's no such thing as work-life balance, there's only life”. This episode explores how culture is the strongest competitive advantage a business has, but also how leaders must model the behaviour they expect.

We also discover the power of output over presenteeism and the clarity that makes autonomy work: no meetings before 10 or after three, school runs protected, and explicit trust to decide when work fits around family. Jeff walks through the moment productivity surged when teams stopped performing hours and started delivering outcomes. He shares why hiring for behaviours and values opens the door to more diverse thinking, stronger collaboration, and genuine equity. 

Jeff also shares the tear-jerking story of how his company stepped up and helped a member of staff when it felt like their life was falling apart. 

How do you really motivate your workforce?  By providing fulfilment - the personal north star that keeps teams accountable, creative, and resilient.

In 2026 Cloudfm Group celebrates its 15th anniversary. 

Find out more about Cloudfm here.

Hosted by Sam Walker 

Watch the podcast on YouTube

Discover Cloudfm Group:

Website  |  LinkedIn

Find the best-selling book Doing The Opposite by Jeff Dewing HERE

In Season Six of Doing the Opposite: Business Disruptors we’re turning the spotlight onto host of the podcast Jeff Dewing. Jeff is Founder and CEO of Cloudfm Group, keynote speaker, bestselling author, and a leader who rebuilt his life and company by doing the one thing most people fear: the opposite. 

What happens when a CEO says “I don’t know” at the worst possible moment? In this episode Jeff looks back on the time when COVID shattered revenue. Jeff didn’t bluff; he admitted he was lost. That choice flipped a switch. The board stepped up with 11 bold scenarios, and set a course not just to survive, but to thrive.  Jeff describes the response in his company: “frontline staff from help desk operators to managers to directors, were sitting there and all they wanted to do was help. I was the old lady that fell over. All they wanted to do is come and help me up.” Vulnerability, used with intent and authenticity, became the catalyst that unlocked scale, trust, and decisive action.
 
Jeff and Sam explore how transparency spreads across teams and client relationships. Instead of legal threats over unpaid invoices, Jeff’s team chose radical openness and ‘little and often’ repayments to keep suppliers alive. The response? Deeper trust, cleaner communication, and partnerships that were stronger coming out of the crisis than going in.  If you’ve ever feared that honesty would erode your authority, this conversation shows the opposite: truth builds credibility, disarms critics, and invites your team to grow taller.

In 2026 Cloudfm Group celebrates its 15th anniversary. 

Find out more about Cloudfm here.

Hosted by Sam Walker 

Watch the podcast on YouTube

Discover Cloudfm Group:

Website  |  LinkedIn

Find the best-selling book Doing The Opposite by Jeff Dewing HERE

In Season Six of Doing the Opposite: Business Disruptors we’re turning the spotlight onto host of the podcast Jeff Dewing. Jeff is Founder and CEO of Cloudfm Group, keynote speaker, bestselling author, and a leader who rebuilt his life and company by doing the one thing most people fear: the opposite.

 In this episode, Jeff breaks down what “Doing the Opposite” really means to him — not change for the sake of change, but having the courage to ask better questions, challenge outdated practices, and put culture ahead of profit so trust and performance can compound over time.

Drawing on his career, Jeff reflects on cultures he’s seen across multiple firms where success is measured solely by financial results. He explains how this mindset encourages people to be economical with the truth, driven by fear rather than purpose. Instead, Jeff argues that failure should be treated as a learning opportunity, not a threat.

We also explore the true role of leadership: you can’t motivate people, but you can inspire them by showing progress, celebrating wins, and making the next step clear, meaningful, and achievable.

In 2026 Cloudfm Group celebrates its 15th anniversary. 

Find out more about Cloudfm here.

Jeff’s book ‘Doing the opposite: A life, its lessons & building success’ is available to buy on Amazon.

Hosted by Sam Walker

Watch the podcast on YouTube

Discover Cloudfm Group:

Website  |  LinkedIn

Find the best-selling book Doing The Opposite by Jeff Dewing HERE

In Season Six of Doing the Opposite: Business Disruptors we’re turning the spotlight onto host of the podcast Jeff Dewing. Jeff is Founder and CEO of Cloudfm Group, keynote speaker, bestselling author, and a leader who rebuilt his life and company by doing the one thing most people fear: the opposite.

In this episode, Jeff reflects on failure and how it has shaped both him and his subsequent successes. Jeff recalls the knock on the door at 7:30 a.m, two cars leaving the drive, neighbours watching through the curtains. Jeff opens up about losing his business, his home and the image of success he’d built, and how that free fall uncovered a better way to lead and to live. What starts as a story of collapse turns into a blueprint: take radical ownership, protect time to think, and build environments where people can win.

In taking over a football club, Jeff discovered the power of company culture and empowering people to thrive. At the club the same players in a different environment were suddenly winning everything. But Jeff admits the football club diverted his focus away from the business, which led ultimately to its collapse. 

From the job centre queue to a £65m rebuild, Jeff lays out the steps that work in any crisis: accept that it’s your responsibility, not to blame yourself but to regain control; choose humility over image; and carve out quiet space to reflect until patterns become clear and a plan emerges. 

In 2026 Cloudfm Group celebrates its 15th anniversary. 

Find out more about Cloudfm here.

Jeff’s book ‘Doing the opposite: A life, its lessons & building success’ is available to buy on Amazon.

Hosted by Sam Walker 

Watch the podcast on YouTube

Discover Cloudfm Group:

Website  |  LinkedIn

Find the best-selling book Doing The Opposite by Jeff Dewing HERE

In Season Six of Doing the Opposite: Business Disruptors we’re turning the spotlight onto host of the podcast Jeff Dewing. Jeff is Founder and CEO of Cloudfm Group, keynote speaker, bestselling author, and a leader who rebuilt his life and company by doing the one thing most people fear: the opposite.

This isn't a podcast about business. It's a podcast about courage. About reinvention. About leading with heart. And daring to do things differently. This podcast isn't about business strategy. It's about the openness to rethink what leadership really is. It's about choosing purpose over ego, innovation over habit, culture over control.

Sam Walker is a broadcaster and journalist, and she’ll be sitting down with the entrepreneur and CEO of Cloudfm Group Jeff Dewing, a man who rebuilt his life after losing everything by challenging the norms we all assume are unshakable. He discovered that doing the opposite isn't rebellion, it's a route back to meaning. Together Sam and Jeff explore resilience, authenticity, purpose, technology, impact, and uncover what's possible when you stop following the crowd and start doing the opposite.

Conversations with Jeff Dewing launches 14th January. Watch on YouTube or listen wherever you get your podcasts. 

In 2026 Cloudfm Group celebrates its 15th anniversary. 

Find out more about Cloudfm here.

Hosted by Sam Walker 

Watch the podcast on YouTube

Discover Cloudfm Group:

Website  |  LinkedIn

Find the best-selling book Doing The Opposite by Jeff Dewing HERE

Doing the Opposite x PropTech Connect is a mini-series celebrating Europe’s largest real estate tech event. In this episode Jeff Dewing speaks to PropTech Connect’s Founder and CEO, Matthew Maltzoff. 

Matthew shares his incredible journey from running a meal delivery startup during COVID to founding Europe's largest PropTech event. Defying conventional wisdom about industry expertise, his refreshing perspective reveals how knowing nothing about real estate or events became his greatest advantage.

When getting started with the event, Matthew’s approach was to ask "How big could it be on the first go?" – setting targets that industry veterans might have dismissed as impossible. Matthew admits that what some may have seen as naivety became his greatest asset: “Because we didn't even know that this was a ridiculous thing, we just figured, well, how will we do this? Failure wasn't really an option” Matthew says. 

What makes Matthew's approach particularly inspirational is his commitment to vulnerability and genuine curiosity. Rather than pretending to have all the answers, he asks fundamental questions about what really matters to the built environment: "How does this make the building more valuable? How does this improve the tenant experience?" This focus on essentials cuts through the noise of "nice-to-have" technologies that don't address core industry needs. 

Matthew highlights a significant shift he’s witnessing in real estate – the move from authoritarian landlord-tenant relationships to collaborative partnerships where property owners ask, "What do you need? What can we do better?". This vulnerability-based leadership creates environments where people feel safe to admit what they don't know and work together on solutions.

A huge thank you to everyone who was part of this year’s Proptech Connect Europe

Hosted by Jeff Dewing

Watch the podcast on YouTube

Discover Cloudfm Group:

Website  |  LinkedIn

Find the best-selling book Doing The Opposite by Jeff Dewing HERE