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Winners Circle With Jay

Winners Circle With Jay

Di: Olanrewaju Jay Adewole
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The Winners Circle Podcast is a powerful business and leadership show hosted by Jay Adewole, award-winning business coach, consultant, entrepreneur, and founder of the Winners Circle movement.

This podcast is built for entrepreneurs, executives, creators, and ambitious professionals who are committed to growth, excellence, and legacy. Each episode features meaningful conversations with business leaders, founders, experts, and changemakers who are building, scaling, overcoming challenges, and creating impact in their industries.

Through honest dialogue, practical insight, and real success stories, The Winners Circle Podcast helps listeners discover what it truly takes to win — not just in business, but in life, leadership, purpose, and personal growth.

Whether you are launching your first business, scaling your company, building your personal brand, or seeking inspiration for your next level, this podcast gives you access to the mindset, strategies, and stories of people who are doing the work and making an impact.

What You Can Expect

On The Winners Circle Podcast, we discuss:

  • Entrepreneurship and business growth

  • Leadership and personal development

  • Wealth-building and financial discipline

  • Branding, marketing, and visibility

  • Overcoming failure and setbacks

  • Purpose, faith, discipline, and legacy

  • The real journey behind success

Winners Circle With Jay
Economia Gestione e leadership Leadership Successo personale Sviluppo personale
  • Your Business Is NOT Your Retirement Plan — The Wealth Mistake Entrepreneurs Can’t Afford
    Oct 14 2026

    Your business may create your wealth—but should it also be your retirement plan?

    In this episode of The Winners Circle Podcast, Jay Adewole sits down with Russ Gaiser and Mike Hoeflich, co-authors of Beyond Break Even and retirement income specialists, to discuss one of the biggest financial blind spots facing entrepreneurs: building a successful company without building a coordinated plan for life after the business.

    Russ and Mike explain why retirement planning for entrepreneurs requires much more than hoping for a large business sale someday. Social Security, taxes, investments, beneficiaries, survivor protection, business value, and an eventual exit strategy all have to work together.

    The conversation explores why Social Security should be treated as a strategic asset, how claiming decisions affect married couples differently, and why survivor planning needs to happen long before either spouse enters retirement.

    They also discuss the important shift from accumulating wealth to creating dependable income from that wealth. For entrepreneurs who have spent decades reinvesting, saving, and delaying gratification, learning how to efficiently use what they have built can be just as important as building it in the first place.

    Russ and Mike break down tax-bucket diversification, Social Security optimization, least-cost retirement planning, beneficiary reviews, and the importance of turning a business exit strategy into an actual income strategy.

    For entrepreneurs, the message is clear:

    Don’t wait until retirement to figure out how your business success becomes personal financial security.

    Whether you are decades away from retirement or already thinking about an exit, this episode will help you start asking the questions that protect your wealth, your spouse, and your legacy.

    Featuring Russ Gaiser & Mike Hoeflich Hosted by Jay Adewole

    Learn more and discover additional episodes at winnerscirclewithjay.com.

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    1 ora
  • The Observer State: How to Stop Reacting and Start Leading Clearly
    Oct 7 2026

    This episode explores why many entrepreneurs feel pressure even when the business looks successful from the outside. Jay Adewole speaks with Pratiqk Jaani; author of Drasty,

    The Perception and creator of the Drasty Method, about how childhood conditioning shapes identity, stress, and the way leaders interpret success. Pratiqk Jaani shares how shifting into the observer state can help entrepreneurs respond with clarity instead of reacting from fear, scarcity, or burnout.

    The conversation focuses on practical self-inquiry, internal calm, and why external achievement alone does not create peace.

    Key topics

    • In this episode, Pratiqk Jaani explains how 20 years as an accountant and tax advisor showed him that business problems are often mindset problems, not resource problems.
    • He shares how fear of failure, fear of judgment, and insecurity kept him in a job for 7 to 8 years before he finally launched his own business.
    • Pratiqk Jaani explains that many people chase success, money, and approval because they were conditioned in childhood to believe fulfillment comes from outside themselves.
    • He introduces the observer state as the part of us that watches thoughts and emotions without becoming them.
    • He compares the conditioned self to a car and the observer self to the driver, emphasizing that emotions and reactions are learned, not fixed identity.
    • He says stress, imposter syndrome, and pressure are often copied responses from childhood experiences, such as watching parents react to deadlines and frustration.
    • Pratiqk Jaani describes the Drasty Method as a 3-day immersive experience designed to help people directly experience the observer state rather than simply learn techniques.
    • He explains that the 30-day integration practice, guided audios, and live experiences support the shift from conditioned reacting to conscious observing.
    • He says entrepreneurs should ask themselves what they are feeling, why they are feeling it, and what childhood experience taught them to react that way.
    • He defines real success as fulfillment, wholeness, and joy in the process, not just money or achievement.

    Key frameworks:

    • Observer state — The detached awareness that notices thoughts and emotions without being controlled by them.
    • Conditioned self — The identity built from childhood praise, punishment, family culture, and repeated emotional patterns.
    • Drasty Method — A 3-day immersive process focused on realizing the observer state and changing how life is experienced.
    • Internal state first — The idea that external reality shifts more effectively after internal perception shifts.

    Notable quotes:

    “The good processes or good structure or good team does not create a successful business. Instead the mindset.”

    “Your external life may not change overnight, but the way you experience it can transform immediately.”

    “Stress is just a way of you know wasting our energy, our focus.”

    Action items

    • Ask yourself what you are feeling before trying to fix the situation.
    • Identify why you are feeling it and what memory or pattern it connects to.
    • Pause, breathe, and observe the feeling instead of immediately reacting.
    • Notice whether you are creating because it brings joy or because you want something back.
    • Use stress as a signal to examine conditioning, not as proof that you are failing.

    #EntrepreneurMindset #FounderLife #BusinessLeadership #WinnerCirclePodcast #MindsetShift

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    54 min
  • The Fear That Nearly Ended the Mission — and Built the Pilot
    Sep 30 2026

    Fear gets loud at 35,000 feet. Jay Adewole sits down with aviator, author, businessman, and global adventurer Robert DeLaurentis, known as the Zen Pilot and the Peace Pilot, for a powerful conversation about flying through fear, leading with purpose, and staying committed when the mission is bigger than the risk.

    Robert shares the mindset that carried him through solo circumnavigations of the planet, including brutal moments over the North Pole, emergency landings, and a terrifying fuel spill in Dakar that could have ended everything.

    But this episode is not just about aviation — it is about what it takes to keep going when you are alone, under pressure, and forced to make decisions with no room for panic.

    You’ll discover:

    • How Robert prepares for major flights by identifying and mitigating risk long before takeoff
    • Why he believes the checklist is one of the most powerful leadership tools in business
    • What his near-death moments taught him about clarity, courage, and execution
    • How silence, solitude, and inner peace become assets instead of obstacles
    • Why fear should be faced, written down, and systematically eliminated
    • How he built a mission around aviation, philanthropy, education, and world peace

    Robert also opens up about the deeper purpose behind the Citizen of the World aircraft, the DeLaurentis Foundation, his books, his films, and the airport projects designed to inspire the next generation.

    From kids staring up at planes to entrepreneurs building alone, this conversation makes the case that noble purpose changes everything.If you are leading a team, building a business, chasing a calling, or just trying to stay steady in turbulent seasons, this episode will challenge you to think bigger, prepare better, and move forward with more courage than fear.

    Essential listening if you need a reminder that the mission matters, and that peace begins within.

    #Winnerscircle #Aviation #Leadership #Entrepreneurship #OvercomingFear #PersonalDevelopment #PurposeDriven #PilotLife #BusinessLeadership #Inspiration

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    56 min
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