Scaling the Wall: Charlie Naughton-Rumbo on creativity, cyber security and career change

Charlie Naughton-Rumbo, CEO of LeftBrain, recently appeared on the Scaling the Wall podcast, a show that explores the real and often unexpected routes people take into information security.

In the episode, Charlie shares how his career evolved from theatre and literary fiction into tech leadership and security strategy. He talks about the creative foundations of LeftBrain, the value of career switchers in cyber, and how communication and creativity are essential to building effective security teams.

It’s a fascinating listen for anyone interested in unconventional career paths and the intersection of creativity and information security.

From creative studios to cyber strategy

Charlie shares how LeftBrain began as an MSP focusing on Mac environments, especially for creative studios. "Back in the day, Macs were the weird tech no one else understood, except creatives," Charlie explains. As more tech companies adopted Macs, the demands evolved. "Tech firms need tight security and have regulatory requirements, so we built our capabilities around security architecture and GRC, including ISO 27001."

Theatre, literature and Apple geniuses

Charlie's unconventional career began in children's theatre, touring the UK and Ireland. "When you're spending months with the same three people, you find ways to stay creative. I wrote my first play on the road and staged it when I was 19." He later studied directing at drama school, becoming the only student to both write and direct a final showcase.

But theatre’s economics proved challenging. “I sold everything, bought a one-way ticket to Australia, and started writing literary fiction.” One manuscript garnered attention from 10 literary agents and nearly landed with a top UK agency, but Charlie admits his work was often “too cerebral.”

While chasing writing dreams, he held down tech support roles and eventually worked at the Apple Genius Bar to support his theatre ambitions. “I just needed enough money for rent and food, nothing more.” That experience became a springboard into full-time tech roles, where he began managing clients with complex security needs.

Security by design and by passion

Charlie’s pivot into information security wasn't immediate. “There were two jumps, first into tech, then sideways into security.” While working in technical account management, he found himself drawn to securing high-trust environments. “Something about securing things just clicked.”

Driven by both passion and life changes, including the birth of his daughters, Charlie pursued certifications such as CISSP, CCSP, and AWS Solutions Architect. “Security architecture gave me the same buzz as running a theatre production. It’s about leading a team towards a shared vision.”

Creativity in leadership and risk

Charlie sees strong parallels between theatre directing and business leadership. “If you hire people with unique skills and backgrounds, and you set a clear direction, the output is better than top-down control. It's like working with a great designer. You give them the vision and they come back with something even better.”

LeftBrain's recruitment reflects this mindset. “We prioritise career switchers. We've hired a former teacher, someone from TV, and even an artist on our helpdesk. They approach problems differently, and that helps us speak our clients’ language.”

One team member recently restructured risk assessments into a narrative format. “Instead of ‘risk mitigations,’ he said, ‘Here’s what you have, here’s what could go wrong, here’s how to fix it.’ It made risk relevant to businesses that don’t think in those terms.”

Why the name ‘LeftBrain’?

While the company now focuses on left-brain activities like compliance and cyber security, the name has creative roots. “We were the left brain to our creative clients’ right brain. Now, I say we’re bringing a right-brain approach to left-brain problems. Diversity and creativity into structure and logic.”

Lessons from a non-traditional path

Reflecting on his journey from children’s theatre to cyber security leadership, Charlie emphasises purpose and alignment. “What I’ve always wanted is to write, create, lead. Whether it’s a play or a business, it’s about leading people toward a vision.”

He no longer writes literary fiction regularly, although he has a middle-grade children’s book in the works for his daughters. “I haven’t missed writing because I get the same buzz from building a company and leading a team.”

Final thoughts: unicorns do exist

Charlie concludes with a message for creatives and career switchers. “Cyber security needs diverse perspectives. The technical skills are teachable. What we need are people who can communicate, lead, and see the bigger picture. We don’t need unicorns, we just need more people with creative backgrounds who are willing to learn.”