Winners Circle With Jay

Olanrewaju Jay Adewole
  • 5.0 (10)
  • 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. 2d ago

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

    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

  2. Sep 9

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

    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

  3. Sep 2

    Why Hourly Billing Is Broken in the AI Era

    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

  4. Aug 26

    The Hidden Financial Mistakes Tech Professionals Make

    A wealth manager for tech professionals shares why small business owners can learn a lot from the same money strategies used by high earners. If you’re trying to make smarter financial decisions, protect your income, or build long-term stability, this quick shoutout points you toward a podcast designed to help you do exactly that. Stanley Leong brings a focused perspective on managing wealth for tech professionals, making this a useful listen for anyone who wants practical financial insight without the fluff. Even in a brief introduction, the value is clear: the right money habits can change how you run, grow, and protect your business. You’ll get a sense of what the Winner Circle podcast is about and why it may be especially valuable for small business owners looking to sharpen their financial thinking. It’s the kind of recommendation that can lead you to better decisions, better questions, and a better handle on your money.If you care about business growth, personal wealth, or learning from people who work with ambitious professionals every day, this is an easy one to explore next. Short, direct, and worth your time. www.winnerscirclewithjay.com #WinnerCirclePodcast #SmallBusinessOwner #TechProfessionals #WealthManager #PodcastRecommendation

    The Hidden Financial Mistakes Tech Professionals Make

  5. Aug 19

    The Legal Path Families Miss When Mental Health Crisis Hits

    Mental health crises and addiction can turn into legal emergencies fast - and most families wait too long before acting. Mark Astor explains the options that can protect a loved one, preserve dignity, and help families make the right move before the situation spirals into jail, hospitalization, or worse.Jay Adewole sits down with Mark Astor, a Florida attorney who built a law firm focused on helping families navigate the intersection of behavioral health and the legal system. Mark shares why so many families feel trapped, why denial keeps crises alive, and how the right legal strategy can create a path toward treatment instead of punishment. You’ll discover: Why families often miss the window to act earlyWhat the Marchman Act and related Florida statutes can doHow emergency orders, treatment placement, and court intervention actually workWhy recovery is a long game and the first year matters so muchThe difference between enabling, waiting, and taking decisive actionMark also breaks down the biggest misconceptions around addiction and mental illness, including the stigma that keeps people silent and the dangerous myth that loved ones can simply “choose” to get well on their own. He explains why families often need to make the decision the struggling person cannot make - and what happens when they wait for rock bottom. The conversation also goes beyond the courtroom. Mark talks candidly about building a niche law firm from scratch, why specialization matters, and how he turned a mission-driven practice into a scalable business with real systems, staff, and reach. If you care about entrepreneurship, leadership, or building something meaningful while helping people in crisis, this part of the episode is just as valuable as the legal guidance.He also addresses access to treatment, the gap between resources and quality care, and why mental health and addiction will remain urgent issues for years to come. This is practical, compassionate, and often eye-opening listening for parents, spouses, business leaders, and anyone who may one day have to make a life-changing decision for someone they love. Mark Astor is a Florida attorney and founder of a specialized law firm focused on mental health and addiction cases, known for helping families use the legal system to pursue treatment and protection. He has handled thousands of cases across criminal law and civil commitment, and now concentrates on guiding families through crisis with clarity and urgency. Perfect for parents, spouses, entrepreneurs, and community leaders who want to understand what to do when a loved one is in crisis - and how to act before it’s too late. #MentalHealthAwareness #AddictionSupport #FamilyCrisis #WinnerCirclePodcast #FloridaLaw

    The Legal Path Families Miss When Mental Health Crisis Hits

  6. Aug 12

    What It Means to Build a Business With Purpose and Impact

    A conversation that gets straight to the heart of building a business with purpose - and the real-world pressure to make it matter. Jay Adewole and Hanna Bauer bring the kind of honesty that cuts through surface-level advice and leaves you thinking about what your company is actually here to do. Hanna Bauer opens with a powerful endorsement of the conversation, pointing to the way it goes beyond tactics and into the deeper reason founders build in the first place. This is not about chasing vanity metrics or vague inspiration - it is about aligning ambition, impact, and the kind of business that creates real change. You will hear a conversation shaped by: the heart behind a founder's visionwhat it takes to build a business that truly serves its missionthe difference between running a company and making a differencewhy purpose matters when growth gets complicatedIf you are building something of your own, leading a team, or trying to reconnect your work with a bigger mission, this episode will resonate. It is a reminder that the best businesses are not just successful - they are intentional.Perfect for founders, operators, and anyone who wants their work to mean more than revenue alone. Tag someone who needs that reminder today 👇 What stood out most to me was this: Growth means nothing if you lose the heart behind it. The real win is building something that actually makes a difference. *The best conversations don’t just inspire you - they realign you. That’s what this one did for me. If you’ve been grinding without checking the mission lately, this is your sign to pause. #TheWinnerCircle #BusinessMindset #EntrepreneurTalk #PurposeDrivenBusiness #BuildWithHeart

    What It Means to Build a Business With Purpose and Impact

  7. Aug 5

    How Entrepreneurs Can Turn Difficult Conversations Into Breakthroughs

    Unlock the secret to transforming conflict into connection—fast. Doug Noll, a renowned peacemaker and conflict resolution expert, reveals how a simple yet powerful skill can de-escalate even the most heated conversations in under 2 minutes. Whether you're leading a team, negotiating with clients, or handling disputes in your personal life, mastering this approach can turn potential crises into breakthroughs. Imagine turning angry, resistant moments into opportunities for collaboration, trust, and understanding. Doug shares his journey from a high-stakes trial lawyer to a mediator with a revolutionary method rooted in neuroscience, emotion recognition, and nervous system regulation. His insights are backed by groundbreaking studies and real-world success—including transforming prison conflicts and high-pressure corporate disputes. You’ll discover how naming emotions—yes, just saying "you're angry"—can instantly lower hostility and open pathways to effective problem-solving. We break down: Why emotion is at the root of every conflict (and why ignoring it makes things worse) The step-by-step process to calm any upset person—clients, colleagues, or loved ones—without blame or judgment How to recognize and regulate your own emotional triggers during crucial conversations Practical tactics for leaders to have difficult performance discussions with confidence The “empathy paradox” and how genuine care can make you a stronger, more authoritative leader Failing to address emotional undercurrents in business can lead to disconnect, turnover, and missed opportunities. Conversely, embracing emotional intelligence through proven techniques creates resilient teams, loyal clients, and a culture of trust. Perfect for founders, CEOs, managers, and anyone tired of conflicts spiraling out of control—this episode equips you with tools to turn tension into teamwork, anger into insight, and obstacles into opportunities. About our guest Doug Noll is a leading authority in de-escalation, conflict management, and empathy leadership. His work has been featured in TEDx talks and his books are in five languages. As a coach and trainer, he’s helped thousands—from prison inmates to Fortune 500 executives—master the art of emotional literacy and nervous system regulation. Don’t just learn how to listen—learn how to name, tame, and transform. Your next breakthrough awaits just one conversation away. Comment below with the toughest conversation you've faced—let’s unlock the secret to transforming conflict into breakthrough moments. Most of us try to "fix" the problem with logic or advice, but emotions are the real driver behind reactions. When you simply name what someone feels, their brain calms, and the tension melts away. That’s not just theory—it's science supported by brain scans! 🧠 Imagine halving your conflict resolution time and transforming tense moments into opportunities for trust. When you understand and regulate emotions, leadership becomes less about control and more about connection. Are you ready to master this? Start practicing daily—name emotions in everyday encounters and watch your relationships—and your business—thrive. Worth thinking about. #LeadershipSkills #ConflictResolution #EmotionalIntelligence #DeEscalate

    How Entrepreneurs Can Turn Difficult Conversations Into Breakthroughs

  8. Jul 29

    The Exit Strategy Every Business Owner Needs Before It’s Too Late

    Most business owners focus on growth and day-to-day operations — but neglect the one thing that could secure their legacy and financial freedom: a strategic exit plan. What if you could confidently sell your business for top dollar, avoid costly mistakes, and transition with clarity — all on your own terms? Discover the critical planning steps that can transform your company into a valuable asset, rather than just a job.In this episode, wealth advisory expert Joseph Lopresti, founder of Clay Point Family Office, pulls back the curtain on the overlooked art of strategic business exit planning. With nearly four decades of experience helping entrepreneurs protect wealth, reduce taxes, and build long-term legacy, Joe explains why waiting until it’s “too late” often leads to regret — and how early, intentional planning can double your business’s sale value without any additional growth.You'll discover: The true meaning of designing your exit — and why it’s often the game-changer for preserving wealth and independenceHow to increase your business value through leadership development, documented processes, and targeted marketing systemsThe sellability score: what it is, why it impacts your valuation, and how to improve it before it’s too lateThe biggest risks that can derail your exit, including unexpected events like death, divorce, and disasters, and how to safeguard against themWhy most owners regret hurried sales and the emotional, financial, and identity-related consequences that followPractical steps to start your exit strategy today — from assessing your current value to planning your legacy and tax mitigation strategiesWhether you're years away from selling or just beginning to think about your future, this episode delivers proven frameworks to help you build a business that works for your life — not just until you sell. Perfect for entrepreneurs who want clarity, confidence, and control over their legacy, it’s a must-listen for anyone serious about their long-term wealth.Joseph Lopresti is the co-author of Exit by Design and CEO of Arlington World Management. His mission: helping entrepreneurs transition their businesses smoothly, maximize value, and secure their personal freedom. With his guidance, you’ll learn how to craft an exit that honors your vision — so you can enjoy the business you built, without regret.Don’t wait until it’s too late. Your ideal exit begins with strategic planning — now. Listen now and start designing your exit today.

    The Exit Strategy Every Business Owner Needs Before It’s Too Late
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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
    103
  • Rating
    Explicit
  • Copyright
    © Winners Circle With Jay
  • Show Website
    Winners Circle With Jay