Getting comfortable with the uncomfortable: Rupert Bedell, Fasthosts

What does it take to lead real transformation? For Rupert Bedell, Managing Director (MD) at Fasthosts, the answer lies not in control, but in creativity. In a career shaped by bold moves and bigger thinking, he has discovered that uncertainty is not something to be feared—it's the space where growth happens.

In the latest episode of the Pivot Points podcast, Rupert reflects on the moments that have defined his journey from corporate heavyweight to challenger brand MD. His story is not linear. From engineering to marketing, from big institutions to fast-moving disruptors, it's a series of brave departures. And at each junction, the same theme recurs: let go of the old playbook, and trust in something more instinctive and more human.

A leap into the unknown

Rupert's first pivot was a personal one. Originally trained as an engineer, he found himself drawn to a different kind of problem-solving. “I was fascinated by how people behave,” he recalls. “Marketing gave me a creative lens to explore that.”

It was a move from systems to stories, from precision to persuasion. And it laid the foundation for a career that would thrive not on certainty, but on navigating ambiguity.

His formative years at American Express and NatWest gave him a masterclass in scale, structure, and stakeholder complexity. But they also revealed a deeper truth: as businesses optimise for performance, creativity often gets left behind.

“The creativity in big brands has been poor in the last 10 years,” Rupert says. “We're nowhere near where we were in terms of original thinking and brilliant campaigns.”

He began to notice the cracks. The short-termism. The reluctance to take risks. It led him to question, what if marketing wasn’t just about delivering ROI, but creating belief?

Leading a challenger brand

That question led him to his boldest pivot yet—leaving the corporate world to lead a challenger brand.

At Fasthosts, Rupert stepped into a business with lower awareness, smaller teams, and fewer resources but bigger expectations. As a new leader for the business, he was eager to not just signal change but signal the right kind of change. "You’ve got to figure out fast where the latent potential is and where the legacy thinking is holding things back. It’s not about blowing it all up. It’s about being brave enough to change the right things."

Building trust without the cushion of big brand equity meant focusing on clarity of positioning and consistency of experience. "People don’t give you the benefit of the doubt in the same way," he explains. "You have to earn trust with every interaction—every customer touchpoint matters more when your name isn't already known."

Navigating team dynamics mid-transformation brought its own complexity. Rupert inherited a team already in motion, with habits, norms and expectations built under previous leadership. "The challenge was establishing new direction without destabilising the momentum that was already there. It’s a fine balance—respecting what works while creating space for what’s next."

Culture is brand

One of Rupert’s most powerful insights is deceptively simple: “Your brand is your culture.”

For brands, it’s more than what you say but about how you show up. “What you deliver, how the customer touchpoints feel, how your people behave—it all has to be aligned.”

This alignment between internal culture and external experience is fast becoming a critical differentiator for brands. Rupert puts it simply: culture is what customers encounter. That’s why the culture inside your business must be deliberately designed—because culture is the brand in action.

In Rupert’s view, brand-building isn’t a marketing job. It’s a leadership job. And culture is the canvas on which it’s painted.

Leading without the playbook

For Rupert, Fasthosts gave him the freedom to reimagine. “Legacy thinking can hold you back,” he says. “When you strip that away, you find a clarity and creativity that’s hard to get in larger businesses.”

His biggest takeaway for leaders is to get comfortable with the uncomfortable and unleash their creativity.

“You don’t need to have all the answers,” Rupert says. “What you need is clarity of direction, belief in your people, and the bravery to back an idea when the numbers aren’t all there yet.”

In a world obsessed with optimisation, Rupert makes the case for imagination.

His pivotal moments weren’t moments of arrival. They were moments of departure. Moments when he chose uncertainty and found clarity on the other side.