Rajesh Nagjee

CEO Coach | Founder, CEO Freedom OS™

I work with scale-stage CEOs who love their business but want their time, energy, and focus back. I help rebuild how the company runs so they can lead toward their vision again.

Rajesh Nagjee

CEO Coach | Founder, CEO Freedom OS™

Helping CEOs unlock their inner force to break through operational bottlenecks, scale without stress, and build profitable companies they actually enjoy running.

Rajesh Nagjee

CEO Coach & Mentor |
The Next Level Guy

Helping CEOs unlock their inner force to break through operational
bottlenecks, scale without stress, and build profitable companies they actually enjoy running.

Rajesh Nagjee

CEO Coach | Founder, CEO Freedom OS™

I work with scale-stage CEOs who love their business but want their time, energy, and focus back. I help rebuild how the company runs so they can lead toward their vision again.

30+

Years as Coach

350+

CEOs Mentored

40k

CXOs Coached

4+

Founder Exits

From Trapped CEO to Freedom Architect

I built my first seven-figure business early and nearly burned out doing it.

On paper, everything looked right. The company was growing. The team was capable.

In reality, every decision still came back to me. Every absence slowed things down.


I hadn’t built freedom. I’d built dependency.


Vacations were interrupted. Strategic work was constantly delayed. The business ran but only if I was holding it together.


That experience forced a hard reset.


Instead of asking how do I work harder, I started asking:

Why does the business need me for this at all?


That question became the foundation of everything I do today.

On paper, everything looked right. The company was growing. The team was capable.

In reality, every decision still came back to me. If I stepped away, things slowed down.


I hadn’t built freedom. I’d built dependence.


Vacations were interrupted. Strategic work kept getting pushed. The business ran, but only if I was holding it together.


That experience forced a hard reset.


Instead of asking how do I work harder, I started asking:

Why does the business need me for this at all?


That question became the foundation of everything I do today.

Built on Proven, Field-Tested Frameworks

The Journey Behind CEO Freedom OS™

Built from decades of running, scaling, and fixing real businesses

1975-1986

1975-1986

1975-1986

Sun Umbrellas Limited

Sun Umbrellas Limited

Sun Umbrellas Limited

Scaled the Hard Way

Scaled the Hard Way

Scaled the Hard Way

Scaled a Legacy Business

Increased market share from 23% to 37% and transitioned a 95-year-old family business into a professionally run operation. Lesson: Growth outpaces the way the business runs.

Increased market share from 23% to 37% and transitioned a 95-year-old family business into a professionally run operation. Lesson: Growth outpaces the way the business runs.

Increased market share from 23% to 37% and transitioned a 95-year-old family business into a professionally run operation. Lesson: Growth outpaces the way the business runs.

1986-1996

Nagjee Memorial Hospital



Founder & CEO

Founder & CEO

Founder & CEO

Founder & CEO

Built and ran India’s first professionally managed trauma-care hospital in rural India, saving 500+ lives annually. Operationally successful; personally overloaded. Lesson: Mission-driven work still breaks without decision systems.

1989

1989

1989

The Breaking Point

The Breaking Point

The Breaking Point

Lost Everything That Mattered

Lost Everything That Mattered

Lost Everything That Mattered

Lost Everything That Mattered

Personal loss, divorce, and a business under strain converged. This was the moment it became clear: I hadn’t built freedom. I’d built dependency. Lesson: If the business can’t run without you, it owns you.

Personal loss, divorce, and a business under strain converged. This was the moment it became clear: I hadn’t built freedom. I’d built dependency. Lesson: If the business can’t run without you, it owns you.

Personal loss, divorce, and a business under strain converged. This was the moment it became clear: I hadn’t built freedom. I’d built dependency. Lesson: If the business can’t run without you, it owns you.

1990

Chrysalis Management Institute Founded

CEO Freedom OS™ Born


Chrysalis Management Institute Founded

The roots of CEO Freedom OS™

CEO Freedom OS™ Born


Chrysalis Management Institute Founded

The roots of CEO Freedom OS™

Began deconstructing why capable CEOs become bottlenecks. Trained over 40,000 executives across 16+ industries. Outcome: The early frameworks that later became CEO Freedom OS™.

2002

2002

2002

London Business School

London Business School

London Business School

Sloan MBA | 14 disciplines mastered

Sloan MBA | 14 disciplines mastered

Sloan MBA | 14 disciplines mastered

Deepened formal training across strategy, constraints, leadership psychology, and systems thinking, combined with decades of operator experience. Lesson: Theory only matters when it survives real businesses.

Deepened formal training across strategy, constraints, leadership psychology, and systems thinking, combined with decades of operator experience. Lesson: Theory only matters when it survives real businesses.

Deepened formal training across strategy, constraints, leadership psychology, and systems thinking, combined with decades of operator experience. Lesson: Theory only matters when it survives real businesses.

2004-Present

Milestone Dubai

&
Milestone Carpentry



Co-Founder & Chairman

Built a profitable landscaping and carpentry business with my wife, Sejal (CEO). Delivered 1000+ projects across Dubai and won multiple industry awards. Lesson: Clear ownership and rhythm outperform hero leadership.

2018-Present

2018-Present

2018-Present

CEO Coach & Mentor

CEO Coach & Mentor

CEO Coach & Mentor

YPO Certified Forum Facilitator

YPO Certified Forum Facilitator

YPO Certified Forum Facilitator

Facilitated 150+ YPO and CEO forums globally. Work focused on scale-stage founders ($5M–$25M) redesigning how decisions, leadership, and execution work. Result: CEOs reclaim 20+ hours per week while growth stabilizes.

Facilitated 150+ YPO and CEO forums globally. Work focused on scale-stage founders ($5M–$25M) redesigning how decisions, leadership, and execution work. Result: CEOs reclaim 20+ hours per week while growth stabilizes.

Facilitated 150+ YPO and CEO forums globally. Work focused on scale-stage founders ($5M–$25M) redesigning how decisions, leadership, and execution work. Result: CEOs reclaim 20+ hours per week while growth stabilizes.

Why This Mission

This work comes from lived experience.

I’ve seen what happens when a CEO carries a business alone for too long. I lived that burnout cycle myself.

And over the years, I’ve watched strong CEOs lose clarity and energy as everything continues to depend on them.

That’s why I do this work. To help CEOs redesign how their companies run so leadership, decisions, and execution don’t collapse back onto one person.

This isn’t about visibility. It’s about building businesses that support the people leading them.

"I want to impact the lives of 1 million people who will never know my name."

"I want to impact the lives of 1 million people who will never know my name."

"I want to impact the lives of 1 million people who will never know my name."

Rajesh Nagjee

CEO Mentor & Coach

Here’s What Some of the World’s Most Influential Business Gurus Have to Say

These are leaders and strategic thinkers who’ve seen real businesses from the inside and how leadership shows up when the pressure is real.

Here’s What Some of the World’s Most Influential Business Gurus Have to Say

These are leaders and strategic thinkers who’ve seen real businesses from the inside and how leadership shows up when the pressure is real.

Here’s What Some of the World’s Most Influential Business Gurus Have to Say

These are leaders and strategic thinkers who’ve seen real businesses from the inside and how leadership shows up when the pressure is real.

Here’s What Some of the World’s Most Influential Business Gurus Have to Say

These are leaders and strategic thinkers who’ve seen real businesses from the inside and how leadership shows up when the pressure is real.

How We'll Work Together

We identify and remove the real bottleneck so your time goes to leadership, direction, and decisions that move the business.

My goal is simple: build systems that free you from operations so
you can finally do CEO-level work.

My goal is simple: build systems that free you from operations so you can finally do CEO-level work. Here’s what makes this different.

My goal is simple: build systems that free you from operations so you can
finally do CEO-level work. Here’s what makes this different.

Inner Game vs. Outer Game

Most CEOs try to solve inner game problems (clarity, decision-making, leadership presence) with outer game tactics (more tools, more meetings, more hustle). It doesn't work. We fix the inner game first then your outer game accelerates effortlessly.

Most CEOs try to solve inner game problems (clarity,
decision-making, leadership presence) with outer game tactics (more tools, more meetings, more hustle). It
doesn't work. We fix the inner game first then your
outer game accelerates effortlessly.

Business Physics vs. Philosophy

SWOT analysis helps you understand. Bottleneck identification helps you breakthrough. We will focus on the physics of your business.

SWOT analysis helps you understand. Bottleneck identification helps you create breakthroughs. We will focus on the physics of your business, finding the constraint, what's slowing you down, not philosophy that sounds good in theory.

Systems Over Advice

Your business isn't mine. Your team isn't my team. Generic advice doesn't scale. Proven systems do. I don't tell you what to do. I help you build the infrastructure that makes the right decisions obvious.

Your business isn't mine. Your team isn't my team.
Generic advice doesn't scale. Proven systems do. I don't
tell you what to do. I help you build the infrastructure
that makes the right decisions obvious.

Ruthless Compassion

I learned this from Mother Teresa in 1986. Real compassion isn't soft. It's a relentless demand for people to show up at their best. That's how I coach. High standards. Deep support. Zero coddling.

I learned this from Mother Teresa in 1986. Real
compassion isn't soft. It's a relentless demand for
people to show up at their best. That's how I coach.
High standards. Deep support. Zero coddling.

You've Seen My Journey. Now Let's Focus On Yours.

Freedom doesn't come from working harder.
It comes from building systems that don't rely on you.

Book your complimentary strategy call. We'll identify your #1 bottleneck and map the exact path to scale your business without burning you out.

You've Seen My Journey.
Now Let's Build Yours.

Freedom doesn't come from working harder.
It comes from building systems that don't rely on you.

Book your complimentary strategy call. We'll identify your #1 bottleneck and map the exact path to scale your business without burning you out.

You've Seen My Journey. Now Let's Build Yours.

Freedom doesn't come from working harder. It comes from building systems that work without you.

Book your complimentary strategy call. We'll identify your #1 bottleneck and map the exact path to scale your business without burning you out.

You've Seen My Journey. Now Let's Focus On Yours.

Freedom doesn't come from working harder.
It comes from building systems that don't rely on you.

Book your complimentary strategy call. We'll identify your #1 bottleneck and map the exact path to scale your business without burning you out.

© 2025 Rajesh Nagjee. All rights reserved.

© 2025 Rajesh Nagjee. All rights reserved.

© 2025 Rajesh Nagjee. All rights reserved.

© 2025 Rajesh Nagjee. All rights reserved.

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