Winners Circle With Jay

Olanrewaju Jay Adewole
  • 5.0 (11)
  • Entrepreneurship
  • Updated Weekly

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

  1. 5d ago

    You’re Not Ready to Scale If Your Business Runs on Chaos

    Got something to say to this podcast? Send a voicemail, and you might hear yourself on the next episode! You Can't Scale Chaos: The Founder Trap Holding Your Business Back Guest: Esther Chukwujekwu | Founder, Timely Operations Host: Jay Adewole | Winners Circle With Jay Your business is growing. Revenue is increasing. Customers are coming in. Your team is expanding. So why does everything still fall apart the moment you step away? Here's a hard truth most entrepreneurs discover too late: A growing business isn't necessarily a scalable business. If every decision needs your approval, your employees constantly need direction, and your operations live entirely inside your head, you haven't built a business that can run independently. You've built a business that depends on you. And that dependence might be the biggest obstacle to your next level of growth. In this powerful episode of Winners Circle With Jay, business strategist and host Jay Adewole sits down with Esther Chukwujekwu, Founder of Timely Operations, to uncover the silent operational chaos that keeps entrepreneurs overwhelmed, teams underperforming, and promising businesses stuck. From ineffective delegation and missing standard operating procedures (SOPs) to unclear accountability, broken workflows, and founder burnout, this conversation exposes why working harder isn't always the answer. Because you can't scale chaos. You can only scale what you've built to work. What You'll Discover in This Episode ✅ The Founder Trap: Why successful entrepreneurs become the biggest bottlenecks in their own businesses—and how to break free. ✅ The Hidden Cost of Growth: Why more customers, employees, and revenue can actually create bigger problems without the right operational foundation. ✅ Systems That Actually Work: How to create practical SOPs, workflows, checklists, and accountability structures that your team will genuinely use. ✅ Delegation Without Micromanagement: How to empower your employees to make decisions without constantly seeking approval. ✅ People vs. Process Problems: How to identify whether poor performance comes from your team, your systems, your tools, or your leadership structure. ✅ The Automation Advantage: Why repetitive manual tasks drain productivity—and how standardization and automation can create breathing room. ✅ The 30-Day Operational Reset: Practical changes you can begin implementing immediately to create a more organized, efficient, and scalable business. Business owners, here's a question for you: If you disappeared from your business for 30 days, would it thrive, survive, or fall apart? Drop your answer in the comments. Let's talk about what it really takes to build a business that doesn't depend on you. If this conversation challenged the way you lead or operate your business: 👍 LIKE this episode. 💬 COMMENT with your biggest operational challenge. 🔔 SUBSCRIBE to Winners Circle With Jay for conversations on entrepreneurship, business growth, leadership, systems, and building sustainable success. 📤 SHARE this episode with a founder who is doing too much and delegating too little. Remember: Growth without structure creates pressure. Growth with structure creates freedom. Build smarter. Lead better. Grow sustainably. #WinnersCircleWithJay #BusinessGrowth #Entrepreneurship #BusinessSystems #Leadership #ScaleYourBusiness #BusinessOperations

    You’re Not Ready to Scale If Your Business Runs on Chaos

  2. Oct 14

    Your Business Is NOT Your Retirement Plan — The Wealth Mistake Entrepreneurs Can’t Afford

    Got something to say to this podcast? Send a voicemail, and you might hear yourself on the next episode! 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.

    Your Business Is NOT Your Retirement Plan — The Wealth Mistake Entrepreneurs Can’t Afford

  3. Oct 7

    The Observer State: How to Stop Reacting and Start Leading Clearly

    Got something to say to this podcast? Send a voicemail, and you might hear yourself on the next episode! 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

    The Observer State: How to Stop Reacting and Start Leading Clearly

  4. Sep 30

    The Fear That Nearly Ended the Mission — and Built the Pilot

    Got something to say to this podcast? Send a voicemail, and you might hear yourself on the next episode! 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 takeoffWhy he believes the checklist is one of the most powerful leadership tools in businessWhat his near-death moments taught him about clarity, courage, and executionHow silence, solitude, and inner peace become assets instead of obstaclesWhy fear should be faced, written down, and systematically eliminatedHow he built a mission around aviation, philanthropy, education, and world peaceRobert 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

    The Fear That Nearly Ended the Mission — and Built the Pilot

  5. Sep 23

    The 60-Second Elevator Speech Every Entrepreneur Needs

    Got something to say to this podcast? Send a voicemail, and you might hear yourself on the next episode! Most leaders do not have a communication problem. They have a clarity, confidence, and delivery problem—and it is costing them opportunities in rooms they never get to re-enter. Jay Adewole sits down with Joe Abreu, founder of GloVisor and creator of Get Up and Speak, for a practical conversation about turning anxiety into presence, packaging your message with impact, and sounding authentic instead of rehearsed. If you have ever frozen when asked, “What do you do?” or felt your mind go blank right before you speak, this episode gives you a way forward. Joe breaks down the mindset behind strong speaking, the 70/30 split between mindset and mechanics, and why most people are far more judged in their own heads than they are by the audience. You will hear how he helps clients build a 60-second elevator speech, how he coaches people to memorize the beginning and ending of a talk, and why storytelling, timing, pauses, and body language can turn an ordinary message into something memorable. We also explore the hidden cost of staying silent, the difference between performing a speech and genuinely connecting, and why your message lands best when it is aligned with who you are. This episode is essential listening for entrepreneurs, executives, leaders, and anyone who knows their voice should be opening doors—not closing them. If you are ready to speak with more clarity, confidence, and courage, this conversation will push you to start using your voice on purpose. #PublicSpeaking #Entrepreneurship #CommunicationSkills #Leadership #ElevatorPitch #Confidence #BusinessGrowth #Storytelling #PersonalBranding #Entrepreneurs

    The 60-Second Elevator Speech Every Entrepreneur Needs

  6. Sep 16

    AI Will Leave Your Business Behind: What Every Founder Needs to Do Now

    Got something to say to this podcast? Send a voicemail, and you might hear yourself on the next episode! Most businesses are chasing AI the wrong way. Ghazenfer Mansoor reveals why the real advantage is not just building faster - it is building the right system, solving the right problem, and turning technology into a growth engine. If you are a founder, business owner, or leader wondering whether you really need an app, a custom platform, or a smarter internal process, this conversation will change how you think about technology. Jay Adwole pushes past the hype to uncover what actually matters before you spend a dollar on software.Ghazenfer, founder of Technology Rivers, shares how companies can use software development, AI, and digital transformation to reduce mistakes, improve efficiency, and create more valuable businesses. He explains why so many products fail, why “we need an app” is usually the wrong starting point, and how blueprinting, discovery, and clear requirements can save you from expensive mistakes later. You'll discover: Why technology should serve your business, not force your business to change around itHow to tell whether you need a web app, mobile app, or no app at allWhy AI-powered “vibe coding” is useful for proof of concept, but not enough for scalable productsThe biggest red flags to watch for when hiring a software developer or technology partnerHow custom technology can help service businesses become more valuable, more profitable, and more sellableWhy the businesses that win over the next five years will be the ones that adopt AI, agents, and automation nowGhazenfer also breaks down how small and mid-sized businesses can compete with larger companies without copying them, using smarter systems, lower-cost automation, and technology that supports the business model instead of distracting from it. He shares practical insight from building software for regulated industries, healthcare, and service businesses, plus lessons from his book Beyond the Download.Essential listening if you want to stop guessing, avoid costly tech mistakes, and build a business that scales with clarity, systems, and AI.

    AI Will Leave Your Business Behind: What Every Founder Needs to Do Now

  7. Sep 9

    Clarity Before Growth - Why Smart Founders Don’t Scale Blind

    Got something to say to this podcast? Send a voicemail, and you might hear yourself on the next episode! In this episode, Jay Adéwólé sits down with Daniel Nikic to unpack clarity, identity, discipline, and what it really takes to build a business people can trust. The conversation centers on personal reinvention, the habits behind credibility, and how founders and investors can make better decisions through sharper self-assessment and research. Daniel shares how his background in research, finance, and global markets shaped his approach to investment research, AI, and founder decision-making. If you are building a company, evaluating startups, or trying to separate signal from hype, this conversation is packed with practical perspective. Key topics Jay opens with the idea that growth without clarity leads to noise, not progress, and frames the episode around identity, reinvention, and discipline.Daniel Nikic shares his background as someone born and raised in Canada with Bosnian roots, with early work experience in administration, tax analysis, railway, and accounting.He explains how his interests in research, data, finance, sports, and global events shaped the way he thinks about business and opportunity.Daniel says entrepreneurship appealed to him because it puts responsibility fully on the operator, which makes discipline, routine, and prioritization essential.He emphasizes that reputation takes years to build and only seconds to ruin, so business leaders must back up what they say.The conversation defines clarity as knowing what you can deliver, what you cannot, and when to outsource instead of pretending to do everything.Daniel breaks down self-assessment as a process of accountability, reviewing failed tasks, missed signals, bad assumptions, and the lessons hidden in mistakes.They discuss AI as a tool, not just an industry, with Daniel arguing that human judgment, context, and auditing remain essential in investment research.Daniel explains that real investment research gives investors clarity on risks, opportunities, markets, competitors, financials, and the team behind a company.For founders, he stresses the importance of MVPs, demos, numbers, simplicity, and evidence of traction rather than just saying a business is scalable.He warns against copying trends without research and says founders must be mentally strong, open to rejection, and willing to pivot in a global market.Jay and Daniel close on due diligence, valuation, market maturity, and the difference between doing research and actually interpreting it well.“Reputation is key. It takes years to build a reputation, but it takes twenty seconds to ruin it.” “AI is a tool. I don't look at it as an industry.” “Research is only good if you use it and if you get insights or takeaways into making a decision.” #winnerscirclepodcast #jayadewole #ClarityBeforeGrowth #Entrepreneurship #StartupInvesting #InvestmentResearch #ArtificialIntelligence #BusinessGrowth #FounderMindset #DueDiligence #Discipline #Leadership #StartupFounders #BusinessStrategy #PersonalDevelopment #EntrepreneurshipPodcast

    Clarity Before Growth - Why Smart Founders Don’t Scale Blind

  8. Sep 2

    Why Hourly Billing Is Broken in the AI Era

    Got something to say to this podcast? Send a voicemail, and you might hear yourself on the next episode! This episode explores when bookkeeping stops being enough and why strategic financial leadership becomes essential for scaling companies. Jay Adewole speaks with Jody Grunden, co-founder of Summit CPA Group and an early pioneer of the virtual CFO model, about cash flow, subscription billing, specialization, and how AI is reshaping accounting. We discuss how founders should think about finance before a crisis hits, why visibility matters more than raw revenue, and what separates a bookkeeper, controller, and CFO in practice. Key topics In this episode, Jody Grunden explains how he moved from traditional accounting into a model built around forecasting, cash flow, and advisory support after realizing hourly accounting did not solve the real problems clients faced.He shares why many business owners know their operations well but lack financial leadership, and how simple weekly cash forecasts can change decision-making.We discuss the difference between bookkeeping, controller-level work, and CFO services, including how a virtual CFO sits on top of the accounting structure and focuses on the future.Jody breaks down the revenue stage where a growing company should seriously consider a virtual CFO, pointing to the $1.5 million range as a key inflection point.He explains why cash is the number one KPI for scaling companies and recommends holding at least 10 percent of annual revenue in cash, with 30 percent as a strong reserve for risk-averse founders.We cover why subscription pricing was a major shift from hourly billing, including predictable cash flow, fewer receivables, clearer client expectations, and easier access to help without bill anxiety.Jody argues that hourly billing is increasingly vulnerable in an AI-driven world, where faster work will make value-based pricing more defensible than time-based pricing.He shares how AI is pushing accountants away from repetitive bookkeeping and into true advisory work, where human judgment and business context matter more.We discuss how Summit scaled by becoming fully remote, building repeatable systems, and focusing on specific verticals like marketing agencies, law firms, nonprofits, and others.Jody emphasizes that specialization helped Summit become a recognized authority, while repeatable processes made consistent growth possible across teams and clients.Notable quotes "Consistency is the important factor." "Subscription no-brainer hourly is broken." "Growing companies don't fail because of lack of effort. They fail because of lack of financial visibility and strategic guidance." #VirtualCFO #BusinessGrowth #ScalingBusiness #FinancialStrategy #CashFlowManagement #FounderAdvice #Entrepreneurship #SmallBusinessTips #StartupFinance #BusinessPodcast #Leadership #CFO #SubscriptionBusiness #FinancialPlanning #BusinessSystems

    Why Hourly Billing Is Broken in the AI Era
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About

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

Information

  • Creator
    Olanrewaju Jay Adewole
  • Years Active
    2023 - 2026
  • Episodes
    108
  • Rating
    Explicit
  • Copyright
    © Winners Circle With Jay
  • Show Website
    Winners Circle With Jay