Winners Circle With Jay

Jay Adewole
  • 5.0 (10)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

Welcome to the Winners Circle Podcast! Your premier destination for unlocking the secrets to success in business and leadership. Prepare yourself for a dynamic mix of thought-provoking discussions, enlightening interviews, and comprehensive conversations with industry trailblazers, accomplished entrepreneurs, and seasoned professionals who have excelled across diverse fields. In the Winners Circle, we dive deep into the multifaceted aspects of leadership, entrepreneurship, business networking, and innovative ideas. Our aim is to empower and inspire you, providing you with actionable insights and knowledge to help you thrive in today’s competitive business landscape. Join us as we embark on this journey toward success together, and let’s elevate our goals to new heights!

  1. 1D AGO

    The Business of Art: Turning Talent into Income

    What if your creativity didn’t have to stay a passion—but could become a profitable, sustainable career? In this episode of The Winners Circle Podcast, Jay Adewole sits down with Tim Packer, founder of Tim Packer Art Academy, to unpack what it truly takes to turn artistic talent into consistent income—without sacrificing authenticity or creative freedom. Tim is an artist, educator, and entrepreneur who has helped countless creatives develop their skills, build strong personal brands, and create multiple income streams from their art. Blending real-world business strategy with deep respect for the creative process, Tim shows artists how to move beyond “hoping it works” and start building careers that last. This conversation goes beyond inspiration. It’s a practical roadmap for artists who want to stop struggling financially and start treating their creativity like the business it deserves to be. In this episode, you’ll learn: Why talent alone isn’t enough—and what artists must add to succeedThe first steps to monetizing your art with confidenceHow to price your work without undervaluing yourselfWays artists can build multiple income streams beyond originalsHow to market your art without feeling “salesy”The mindset shifts required to thrive creatively and financiallyHow to balance artistic integrity with smart business decisionsWhat a truly sustainable art career looks like long-termTim also shares how artists can navigate fear, rejection, and overwhelm—while building systems that support growth, stability, and fulfillment. Whether you’re a painter, illustrator, digital artist, creative entrepreneur, or someone sitting on untapped talent, this episode will challenge how you think about art, money, and success. 🎧 Listen now on all Winners Circle Podcast platforms and discover how creativity, strategy, and entrepreneurship intersect to turn talent into income—on your own terms.

    43 min
  2. The Vital Connection Between Entrepreneurs and Investors

    APR 8

    The Vital Connection Between Entrepreneurs and Investors

    What truly separates founders who struggle to raise capital from those who scale transformative companies? It’s not just the idea—it’s the connection between entrepreneurs and investors. In this episode of The Winners Circle Podcast, Jay Adewole sits down with Scott Kelly, Founder & CEO of Black Dog Venture Partners, for a masterclass on how innovation, capital, and trust intersect. With more than three decades of experience working on both sides of the table, Scott has helped founders refine their vision, sharpen their pitch, and access the right investors—while also guiding investors toward high-potential opportunities that sustain long-term innovation. His work bridges the gap between bold ideas and smart capital. Scott is widely known as the organizer and MC of VC Fast Pitch, where entrepreneurs connect directly with some of the world’s top investors, and as the host of the Emerging Managers Podcast, a show exploring why new and emerging VC funds may represent the next great investment opportunity. In this conversation, Scott shares deep insights from training thousands of salespeople, building investor networks, and watching firsthand what makes founder–investor relationships succeed—or fail. In this episode, you’ll learn: Why the entrepreneur–investor relationship is the foundation of scalable innovationHow founders can position themselves to attract the right investors—not just capitalWhat investors actually look for beyond the pitch deckCommon mistakes founders make when approaching investorsHow trust, alignment, and communication drive long-term successThe evolving role of emerging fund managers in today’s VC landscapeHow platforms like VC Fast Pitch accelerate meaningful connectionsThis episode is a must-listen for founders raising capital, investors seeking differentiated deal flow, and entrepreneurs who want to understand how money, innovation, and execution truly work together. 🎧 Listen now on all Winners Circle Podcast platforms and discover how powerful connections—not just capital—build winning companies.

    45 min
  3. Transitioning from Employee to Entrepreneur

    APR 1

    Transitioning from Employee to Entrepreneur

    What does it really take to move from a steady paycheck to owning a business that aligns with your goals, lifestyle, and long-term vision? In this episode of The Winners Circle Podcast, Jay Adewole sits down with Rick Morgin, a seasoned franchise consultant and business development executive with over 30 years of experience helping professionals transition from employees to confident entrepreneurs—using the franchise ownership model. Rick’s passion for franchise consulting is rooted in helping individuals pursue business ownership, freedom, and the American Dream—without starting from scratch. His process is deeply personal, practical, and strategic, guiding clients through identifying the right industries, franchise concepts, investment levels, and long-term exit strategies. With a career spanning global brands such as WineDirect, Constellation Brands, Treasury Wine Estates, and Joseph E. Seagram & Sons, Rick brings rare insight into finance, sales, marketing, and franchising—because he’s worn all those shoes. In this conversation, Rick explores the emotional, financial, and strategic realities of entrepreneurship—and how franchising can offer a proven path with reduced risk for the right individual. In this episode, you’ll learn: What it truly means to transition from employee to entrepreneurWhy franchising can be a smart entry point into business ownershipHow to identify industries and franchise models that fit youThe real costs involved in franchise ownership—and what to expectHow to assess your transferable skills for entrepreneurial successWhy clarity, trust, and alignment matter more than hypeHow to think about long-term goals and exit strategy before you investRick also challenges listeners with a powerful question: “What would make you jump out of bed every morning?” From there, he shows how the right business model can be intentionally built around your lifestyle, values, and financial goals. Rick is known for building deep trust between his clients and franchisors, ensuring integrity, transparency, and alignment every step of the way. His consulting services are free of charge, making this episode especially valuable for professionals considering entrepreneurship but unsure where to begin. 🎧 Listen now on all Winners Circle Podcast platforms and discover whether franchise ownership could be your bridge from employment to entrepreneurship.

    36 min
  4. Investing for Beginners: Where to Start


    MAR 25

    Investing for Beginners: Where to Start


    If investing feels confusing, intimidating, or out of reach—this episode is for you. In this episode of The Winners Circle Podcast, host Jay Adewole sits down with Joey Mure, Managing Partner of Wealth Without Wall Street, to break down investing for absolute beginners—in simple, practical terms anyone can understand. Joey has helped thousands of individuals escape traditional financial confusion and build wealth with confidence by focusing on clarity, discipline, and strategic decision-making. His philosophy is rooted in empowering everyday people to take control of their money—without relying solely on Wall Street or complicated systems. In this episode, you’ll learn: 💡 What investing really means for beginners (without the jargon) 💡 The very first step to take before investing any money 💡 Common beginner mistakes—and how to avoid them 💡 How much money you actually need to start investing 💡 How to tell if an investment is safe, risky, or simply not right for you 💡 Why mindset matters more than math when building wealth 💡 The role of cash-flowing assets in long-term financial freedom 💡 How to move from fear and confusion to confidence and clarity Joey explains why financial freedom isn’t reserved for experts or the wealthy—it starts with understanding your options, building the right habits, and taking consistent action. Whether you’re brand new to investing or someone who’s been “meaning to start” for years, this episode gives you a clear roadmap to begin your wealth-building journey—starting right where you are. #WinnersCirclePodcast #JayAdewole #JoeyMure #InvestingForBeginners #FinancialFreedom #WealthBuilding #PersonalFinance #MoneyMindset #BeginnerInvesting #CashFlow #FinancialEducation #BuildWealth #WealthWithoutWallStreet

    43 min
  5. The Hidden Costs Draining Your Business — And How to Fix Them

    MAR 18

    The Hidden Costs Draining Your Business — And How to Fix Them

    What if your business isn’t struggling because of revenue—but because of invisible costs you don’t even see? In this episode of The Winners Circle Podcast, host Jay Adewole sits down with Jason Kruger, Partner at Citrin Cooperman and a seasoned business advisor with over 20 years of experience helping leaders uncover financial blind spots that quietly drain profitability. Jason specializes in transforming unclear, incomplete, or chaotic financial data into clear, actionable insights that empower smarter decisions. As the founder of Signature Analytics and now a leader at Citrin Cooperman, he has helped companies cut unnecessary costs, improve reporting, optimize cash flow, and build financially resilient organizations. In this episode, you’ll learn: 📊 What “hidden costs” really are—and why most leaders miss them 📊 The top operational and financial leaks draining growing businesses 📊 How internal inefficiencies quietly erode profit margins 📊 Why poor financial visibility leads to bad leadership decisions 📊 The role of accurate, timely reporting as a competitive advantage 📊 Early warning signs of cash-flow problems before they become crises 📊 How pricing mistakes and staffing decisions impact long-term profit 📊 Practical steps to regain control of your numbers—starting now Jason explains why financial clarity isn’t just an accounting function—it’s a leadership skill. When executives truly understand the story behind their numbers, they gain the power to reduce waste, protect margins, and scale with confidence. If you’re a business owner, executive, or founder who feels like money is slipping through the cracks—this episode will help you identify where it’s happening and how to fix it before it costs you growth. #WinnersCirclePodcast #JayAdewole #JasonKruger #BusinessFinance #HiddenCosts #Profitability #CashFlow #FinancialClarity #Leadership #BusinessGrowth #OperationalEfficiency #ScalingSmart #FounderMindset #ExecutiveLeadership

    40 min
  6. Financial Lessons They Don’t Teach in School: Real-World Money Education Everyone Needs

    MAR 11

    Financial Lessons They Don’t Teach in School: Real-World Money Education Everyone Needs

    Why do so many intelligent, hardworking people still struggle with money? In this eye-opening episode of The Winners Circle Podcast, host Jay Adewole sits down with Robert Rolih, a financial educator and advocate for practical money knowledge, to uncover the financial lessons most of us were never taught in school—but desperately need in real life. Robert’s mission is simple yet powerful: to bridge the gap between traditional education and real-world financial skills. With years of experience guiding individuals through budgeting, investing, credit, and wealth-building strategies, he helps everyday people gain clarity, confidence, and control over their money—regardless of age or background. In this conversation, Robert breaks down money concepts in a way that’s easy to understand, actionable, and immediately applicable. In this episode, you’ll learn: 💡 The most important financial lessons schools often leave out 💡 Why budgeting is actually a tool for freedom—not restriction 💡 How beginners can start investing safely without feeling overwhelmed 💡 Common financial pitfalls that keep people stuck—and how to avoid them 💡 How to manage debt, credit, and cash flow responsibly 💡 The mindset shifts required to build long-term financial confidence 💡 Practical steps anyone can take to begin their journey toward financial independence This episode is perfect for students, young professionals, entrepreneurs, parents, and anyone who wants to make smarter money decisions and break cycles of financial uncertainty. If you’ve ever felt confused, intimidated, or behind when it comes to money—this conversation will remind you that it’s never too late to learn the fundamentals that truly matter. 🔖 Hashtags #WinnersCirclePodcast #JayAdewole #RobertRolih #FinancialLiteracy #MoneyEducation #WealthBuilding #PersonalFinance #InvestingBasics #FinancialFreedom #MoneyMindset #RealWorldFinance

    42 min
  7. From Burnout to Breakthrough: A Dialogue with Justin Montgomery

    MAR 4

    From Burnout to Breakthrough: A Dialogue with Justin Montgomery

    What happens when the career that once inspired you begins to drain your energy, time, and freedom? In this powerful episode of The Winners Circle Podcast, host Jay Adewole sits down with Justin Montgomery, a former ER Nurse Practitioner who transformed frontline burnout into an eight-figure continuing education business. After years in emergency medicine, Justin witnessed firsthand the exhaustion, rigid schedules, and capped earning potential facing healthcare professionals. Instead of remaining stuck in a system that no longer aligned with his vision, he leveraged his clinical expertise to build ProCourse Start—a scalable education platform that helps physicians and advanced practice providers create new income streams, impact more lives, and reclaim time freedom beyond the bedside. In this episode, you’ll learn: 🧠 What truly causes burnout—and why it’s not just about workload 🧠 The mindset shifts required to move from clinician to entrepreneur 🧠 How Justin turned expertise into scalable, sustainable education products 🧠 What “freedom beyond practice” really looks like in today’s economy 🧠 How professionals can diversify income without abandoning their field 🧠 The systems and decisions that helped scale an education business to eight figures 🧠 How to build impact, income, and purpose without sacrificing balance Justin shares an honest, practical breakdown of how skills earned in one career can become the foundation for an entirely new chapter—one defined by choice, leverage, and alignment. If you’re a healthcare professional, high achiever, or expert feeling burned out, boxed in, or ready for more—this conversation will show you that your experience isn’t limiting you. It may be your greatest asset. 👉 Watch now and discover how burnout can become the starting point for your breakthrough. #WinnersCirclePodcast #JayAdewole #JustinMontgomery #BurnoutToBreakthrough #HealthcareEntrepreneur #CareerPivot #ProCourseStart #FreedomBeyondPractice #ExpertToEntrepreneur #PurposeDrivenBusiness #ScalableEducation #TimeFreedom

    44 min
  8. Why Most Marketing Fails — And How to Finally Get Results

    FEB 25

    Why Most Marketing Fails — And How to Finally Get Results

    Why does marketing feel so hard—and why do so many business owners do “everything right” and still see no results? In this episode of The Winners Circle Podcast, host Jay Adewole sits down with Sean Garner, a marketing strategist, business coach, and founder of Sean Garner Consulting, to break down why most marketing fails and what actually works if you want consistent, predictable growth. Sean specializes in helping small and medium-sized businesses scale by mastering one critical advantage: positioning power—becoming the trusted expert in your niche instead of blending into the noise. Through years of coaching founders and building profitable service businesses, Sean has seen the same mistakes repeated over and over: unclear messaging, weak positioning, and chasing trends instead of results. In this episode, you’ll learn: 📌 The #1 reason marketing fails, even when you’re posting and running ads 📌 Why positioning matters more than tactics, tools, or algorithms 📌 How to fix messaging that kills conversions 📌 The most overrated marketing strategies to stop relying on 📌 Underrated strategies that consistently drive leads and sales 📌 How to attract qualified leads, not just traffic 📌 Simple frameworks to build predictable marketing systems 📌 How to become the trusted expert in your niche without feeling salesy Sean shares practical, no-fluff insights that help business owners move from scattered efforts to clear, strategic marketing that converts—without burning time, money, or energy. If you’re tired of guessing, overwhelmed by trends, or frustrated with inconsistent results, this episode will help you rethink marketing with clarity, confidence, and control. 📌 About the Show The Winners Circle Podcast features actionable conversations with entrepreneurs, strategists, and leaders who share real frameworks for growth, leadership, and sustainable success. #WinnersCirclePodcast #JayAdewole #SeanGarner #MarketingStrategy #WhyMarketingFails #PositioningPower #BusinessGrowth #LeadGeneration #ServiceBusiness #Entrepreneurship #MarketingSystems #BrandPositioning #SmallBusinessMarketing #DigitalMarketing #PredictableGrowth #FounderMindset #MarketingClarity

    31 min
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Trailer

5
out of 5
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About

Welcome to the Winners Circle Podcast! Your premier destination for unlocking the secrets to success in business and leadership. Prepare yourself for a dynamic mix of thought-provoking discussions, enlightening interviews, and comprehensive conversations with industry trailblazers, accomplished entrepreneurs, and seasoned professionals who have excelled across diverse fields. In the Winners Circle, we dive deep into the multifaceted aspects of leadership, entrepreneurship, business networking, and innovative ideas. Our aim is to empower and inspire you, providing you with actionable insights and knowledge to help you thrive in today’s competitive business landscape. Join us as we embark on this journey toward success together, and let’s elevate our goals to new heights!

Information

  • Creator
    Jay Adewole
  • Years Active
    2023 - 2026
  • Episodes
    85
  • Rating
    Clean
  • Copyright
    © Winners Circle With Jay 2024
  • Show Website
    Winners Circle With Jay