ALL THE POWER
Roy Castleman standing at the base of a waterfall in Iceland

Four businesses. Five hours a week. And a life I actually want.

That's what my life looks like now. It took 28 years, a few spectacular failures, and learning to think completely differently to get here.

Roy Castleman is a business transformation coach, entrepreneur, and author who built multiple seven-figure IT service businesses over 28 years before discovering that the real breakthrough was not working harder — it was thinking differently. A certified BOS UP coach and Wim Hof Method Level 2 instructor based in Bedfordshire, UK, Roy now helps service company owners build businesses that serve their lives through the T.H.R.I.V.E. method. He is the author of “Thinking Outside Your Brain with AI” (2026, ISBN 978-1-0676727-0-6) and still actively operates his own companies.

What the life actually looks like

I pick my daughter up from school. I am present at dinner — actually present, not mentally rewriting tomorrow's operations list. Last month I was freediving under ice in Finland. The month before, running workshops in Portugal.

Three of my businesses run without me. The fourth — coaching service company owners through the same transformation I went through — is the one I choose to show up for. Not because it needs me every hour. Because I love the work.

I sleep seven hours a night. I have more energy at 50 than I did at 35. I make decisions from clarity instead of exhaustion. This is not a retirement story. This is what happens when you build the right systems and learn to think differently.

Roy Castleman working at his desk, phone in hand, smiling

How I got here

I landed in London in 1997 with seventy-five pounds in my pocket and no idea what I was doing. A recruitment firm sent me to buy a book called “Excel in 20 Minutes.” I read it in a cafe, passed their test, got the job. That evening I had five pounds left.

Over the next thirty years I built IT service businesses across more than thirty countries. Revenue grew. Teams grew. On paper, everything was working. But I was the business. Every decision ran through me. The money was good. The lifestyle looked impressive. And the weight of carrying everything alone was slowly crushing me.

The turning point

I was working ninety-hour weeks across multiple businesses. Sleeping two hours a night. Then I was hospitalised with a burst colon from the stress. I came close to ending it all. That was the lowest point of my life — and the moment everything changed.

Lying in that hospital bed, I knew I could not go back to the way things were. Something fundamental had to change. Not the businesses. Me.

What changed everything

I started with my body. Breathwork. Cold water. Learning to regulate a nervous system that had been running on cortisol for twenty years. For the first time in years, I could think clearly.

Then I found BOS UP — a business operating system that gave my businesses structure that did not depend entirely on me. I became the UK's first certified BOS UP coach.

And then AI. Not as another tool to manage. As a thinking partner. A way to get the ideas stuck in my head out, organised, and acted on. My podcast production went from two and a half days to fifteen minutes. But that was not the point. The point was that for the first time, my brain was not full.

Clear thinking first. Time back second. Business rebuilt third. In that order.

The proof

28
Years Building Businesses
30+
Countries
2,500+
Skydives
90 → 5
Hours Per Week
  • Certified BOS UP coach (UK's first)
  • Certified Wim Hof Method instructor (Level 2)
  • Oxygen Advantage certified
  • UK Help to Grow Mentor
  • Author of “Thinking Outside Your Brain with AI” (2026)
  • British head-down skydiving record holder
  • Freediver — ice freediving in Finland, Silfra in Iceland
  • Active operator of four businesses
Roy Castleman outdoors, relaxed and present

About Roy

What's Roy's background?+
Roy arrived in the UK from South Africa in 1997 with seventy-five pounds. Over 28 years he built multiple seven-figure IT service businesses operating across 30+ countries. He now runs four businesses — three on five hours a week — and coaches service company owners through the T.H.R.I.V.E. method. He is a certified BOS UP coach, certified Wim Hof Method instructor (Level 2), UK Help to Grow Mentor, and author of Thinking Outside Your Brain with AI.
What qualifications does Roy have?+
Roy is the UK's first certified BOS UP coach, a certified Wim Hof Method instructor (Level 2), Oxygen Advantage certified, and a UK Help to Grow Mentor. He has 28 years of experience building and operating IT service businesses across 30+ countries. He is the author of Thinking Outside Your Brain with AI, published in 2026.
Does Roy still run businesses?+
Yes. Roy actively operates four businesses — three of which run on five hours a week. He is not a retired founder giving advice from the sidelines. The methods he teaches are the same ones running his own companies right now.
What makes Roy different from other business coaches?+
Roy is the only coach who combines an AI thinking methodology (EVOLVE), a certified business operating system (BOS UP), and wellness-based performance into a single method. He didn't study business coaching — he built real service businesses for 28 years, nearly lost everything, and rebuilt using the exact system he now teaches.

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