Meet Jay Adewole

Harvard Alumni | Award-Winning Business Coach | Entrepreneur | Speaker

Jay blends strategic consulting, leadership development, and media to empower entrepreneurs across borders.

Building Businesses That Are Structured, Scalable, and Built to Last

Winners Circle exists for one reason:
to help serious entrepreneurs stop operating in chaos and start running businesses with clarity, structure, and control.

This is not about hustle culture.
It’s about strategy, systems, and disciplined execution.

Winners Circle is a strategic coaching and advisory platform designed for founders, consultants, and service-based entrepreneurs who have outgrown trial-and-error and are ready to operate at a higher level.

Our Philosophy

Most businesses don’t fail because the founder isn’t talented.
They fail because the business was never properly designed.

At Winners Circle, we believe:

Clarity beats effort

Systems beat motivation

Structure creates freedom

Leadership determines scale

We help entrepreneurs replace guesswork with strategy, replace overwhelm with systems, and replace hustle with intentional growth.

AS SEEN ON

Meet Jay Adewole

Jay Adewole is a business consultant, coach, and strategic advisor known for helping founders transform scattered operations into structured, scalable businesses.

As the Managing Partner at Point of View Consulting and the host of The Winners Circle Podcast, Jay works at the intersection of strategy, systems, and execution—helping entrepreneurs move from operator mode into true CEO leadership.

With experience advising service businesses, consultants, and growth-stage founders, Jay’s approach is grounded in real-world execution—not theory.

He is known for:

Cutting through noise and complexity
Identifying structural gaps holding businesses back
Designing clear growth paths rooted in systems and pricing strategy
Holding leaders accountable to higher standards of execution

Winners Circle was created as a direct response to what Jay repeatedly saw in the market: talented people stuck because their business lacked structure.

Jay isn’t a motivational speaker pretending to be a coach.

He is a strategist — with real experience building businesses, optimizing operations, structuring teams, and elevating leaders.

✔ Harvard-trained thinking

✔ Award-winning leadership

✔ Real consulting background

✔ High-level strategic frameworks

✔ Media influence and brand authority

✔ Multi-industry business experience

✔ Emotional intelligence & mindset development

Most coaches teach theory.
Jay teaches clarity, execution, and systems — the things that actually change businesses.

Over the years, Jay has worked with:

Entrepreneurs across the U.S., Africa, and Europe

Service-based business owners, coaches, and CEOs

Leaders seeking clarity, direction, and confidence

Entrepreneurs building brands from scratch

Founders needing structure and systems

His coaching and strategic frameworks have helped entrepreneurs:

✔ Raise their prices
✔ Launch their business successfully
✔ Build authority in their industry
✔ Improve operations
✔ Increase revenue
✔ Become more confident leaders

Jay believes in:

Purpose. Clarity. Structure. Execution. Leadership.

His coaching is built on five core principles:

Clarity is the foundation of strategy.
Structure removes overwhelm.
Systems create freedom.
Leadership shapes results.
Consistency wins every time.

What Makes Winners Circle Different

Winners Circle is not a course library.

It’s not group motivation.
And it’s not generic coaching.

It is a strategic transformation platform.

We focus on:

Business architecture, not tactics
Pricing power, not volume chasing
Systems that reduce chaos
Leadership discipline that scales

“Every framework, session, and tool is designed to help clients build businesses that can grow without burning them out."

Winners Circle sits within a broader ecosystem designed to support growth at every level:

Point of View Consulting – Business strategy, operations, and systems design
- Winners Circle Podcast – Leadership, growth, and execution conversations
- POV CRM – Infrastructure and automation for scaling service businesses
Each part of the ecosystem supports one goal:
building businesses that operate with intention, clarity, and control.

Winners Circle is built for:

Service-based entrepreneurs
Consultants and coaches
Agency owners
Founders with revenue but no structure
Leaders ready to operate like CEOs

It is for people who are ready to implement, not just learn.

We believe:

Not everyone should be a client
Growth requires discipline
Structure is non-negotiable
Execution is the real differentiator

That’s why most of our programs begin with an application process.

Ready to Build Differently?

If you’re done guessing, done overworking, and ready to build a business that actually supports your life—not consumes it—Winners Circle may be the next step.