Winners Circle With Jay

Hosted by Olanrewaju Jay Adewole

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100

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Aug 2026

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About the show

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

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September 9, 202632 min

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

September 2, 202642 min

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

August 26, 202646 min

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

August 19, 202645 min

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 early What the Marchman Act and related Florida statutes can do How emergency orders, treatment placement, and court intervention actually work Why recovery is a long game and the first year matters so much The difference between enabling, waiting, and taking decisive action Mark 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

August 12, 202655 min

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 vision what it takes to build a business that truly serves its mission the difference between running a company and making a difference why purpose matters when growth gets complicated If 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

August 5, 202656 min

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

July 29, 202639 min

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 independence How to increase your business value through leadership development, documented processes, and targeted marketing systems The sellability score: what it is, why it impacts your valuation, and how to improve it before it’s too late The biggest risks that can derail your exit, including unexpected events like death, divorce, and disasters, and how to safeguard against them Why most owners regret hurried sales and the emotional, financial, and identity-related consequences that follow Practical steps to start your exit strategy today — from assessing your current value to planning your legacy and tax mitigation strategies Whether 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.

June 25, 202639 min

Unlocking the Secret to Market Domination: The Strategy Top CEOs Don't Want You to Know

Most entrepreneurs accept competition as an unavoidable reality—and lose the opportunity to dominate their market. Charles Gaudet reveals why smart positioning, not just marketing, is the real game-changer for predictable profits. What if the key to growth isn’t fighting for attention but rewriting the rules of your industry using proprietary frameworks and demand architecture? This episode will shift the way you think about competition and show you what top companies do to own their market space. Joining us as a special host for this episode is Dr. Osaretin Agbonavbare, sitting in for Jay Adewole. Dr. Osaretin brings a fresh perspective and insightful questions that drive the conversation deeper into the strategies that matter. Discover how leading companies leverage unique advantage points—think patented systems and tailored frameworks—that allow them to scale beyond dependence on founder intuition. Charles shares concrete strategies for turning intangible expertise into tangible, owned assets that boost credibility and drive relentless demand. You'll learn why most businesses sound alike—and how to stand out by packaging what makes you differently uncommonly effective. We break down the essential steps to craft a market strategy that eliminates head-to-head competition. Charles discusses the power of niche focus—whether you’re already established or just starting—and how to dominate your category in an AI-driven landscape. Plus, insights into how marketing as a function, demand creation, and content consumption can make your sales more predictable and repeatable—without reliance on meetings or pushy tactics. The stakes are high: in the future, 100% of high-ticket sales will happen before that first call, thanks to the rise of AI and research-driven buyers. If you want to lead in this new era, understanding how to build an expert profile, leverage AI to your advantage, and position yourself as an undeniable authority is essential. Without it, competitors will simply outshine you—and invisibility will follow. Perfect for founders and funders eager to innovate their approach, this episode offers actionable lessons on dominating your industry, not just competing within it. Connect with Charles Gaudet at predictableprofits.com or LinkedIn by mentioning the Winner’s Cycle Podcast to get exclusive resources, workshops, and the proven systems that turn industry frameworks into profits. Don’t just keep up—learn to own your market, elevate your positioning, and unlock the growth your business deserves. Market Domination, Smart Positioning, Proprietary Frameworks, Demand Architecture, AI-Driven Landscape, Charles Gaudet, Dr. Osaretin Agbonavbare, Business Strategy, Competition, Entrepreneur Growth

June 17, 202650 min

Why Most Startups Fail Before They Even Reach the First Milestone

Most startups collapse not because of their ideas, but because of fundamental missteps early on. Mike Armistead, a seasoned CEO with over 40 years of experience—from IPOs to multi-million acquisitions—reveals the crucial pitfalls that derail businesses before they even get started. If you’re a founder or executive aiming for longevity and impact, this episode is your blueprint for avoiding common traps and building a resilient company that can withstand market shifts. Joining Mike is Dr. Osaretin Agbonavbare, stepping in for Jay Adewole, to provide additional insights into the dynamics of startup success. Together, they dig into the real reasons behind startup failures, emphasizing the importance of market fit, product value, and stage-specific leadership. You'll discover: why understanding your market dynamics is vital for survival, how to evaluate product-market fit beyond surface metrics, and why revenue growth alone isn’t enough without strategic value creation. They unpack how early-stage founders can sidestep disastrous mistakes—like overestimating market size or neglecting customer engagement—and how to position your company for acquisition or sustained growth. We break down actionable strategies: from assessing when to scale, building an enterprise value, to maintaining discipline and passion over the long haul. Mike and Dr. Osaretin share insights on managing distributed teams in a world shifting toward remote work, and why AI is a game-changer—not a threat—for established businesses. Their advice? Jump into AI tools now to innovate and stay ahead, but do so with purpose. You’ll also hear first-hand lessons from failures, including how gut-wrenching downturns and strategic missteps became turning points for future success. This episode is a must-listen for any founder serious about longevity. Whether you're scaling from six figures or preparing for your exit, understanding these fundamentals can mean the difference between burning out or building a legacy. Get ready to rethink growth, resilience, and leadership—because success lies in mastering the basics when nobody’s watching. Mike Armistead is a veteran CEO and managing partner at Pulse Security AI, bringing unrivaled insight from leading globally recognized startups and tech giants. His journey from early startup struggles to strategic acquisitions offers invaluable lessons for today’s entrepreneurs and investors. Startups, Failure, Market Fit, Product Value, Leadership, Resilience, AI Tools, Strategic Growth, Entrepreneurship, Business Success, Mike Armistead, Dr. Osaretin Agbonavbare, Remote Work, Innovation, Acquisition, Longevity, Founders, Business Strategy, Cybersecurity, Distributed Teams

June 10, 202637 min

The Hidden Power of Authenticity in a World Obsessed with AI and Homogeneity

When you build your own table, you create space for authentic leadership that actually works in today's world. Nikki Barua reveals how shedding the need for approval and embracing your true self can unlock extraordinary success—both personally and professionally. In a landscape where traditional systems favor conformity and superficial connections, Nikki shares her journey from trying to fit in to designing a life and career rooted in authenticity. She explains how the relentless pursuit of belonging often costs leaders their depth, influence, and genuine impact—and how choosing to be visible as yourself is the most powerful leadership move you can make. You'll discover: Why authenticity is your greatest competitive advantage in the age of AI and rapid change How to navigate unspoken systemic standards without losing your identity The difference between assimilation and acculturation—and how the latter empowers you The importance of differentiation through your unique story, scars, and perspectives Practical steps for building powerful, authentic networks and partnerships The stakes are high: if you ignore the power of authenticity, you risk blending in, missing opportunities, and remaining on the outside looking in. But if you lean into your true self, you'll craft a pathway to influence that’s resilient, scalable, and uniquely yours. It’s about leading with courage, not conformity, and designing systems that amplify your voice and value. Perfect for ambitious leaders, entrepreneurs, and change-makers tired of playing by rules they didn't create—this episode is your blueprint for building a legacy rooted in authenticity. When you step into the light of your real self, the right opportunities, people, and impact follow. Join Nikki as she shares how to turn your authentic leadership into your greatest asset—and why building your own table isn't just metaphorical, but a strategic move for future-proof success.