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.
WORK WITH JAY
If you’re ready to gain clarity, elevate your strategy, and grow your business with intention, Jay offers three levels of coaching:
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.
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