Winners Circle With Jay

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,

Winners Circle With Jay is a business podcast hosted by Olanrewaju Jay Adewole, with 104 episodes on record and a Required Pod Score of 80.

Olanrewaju Jay Adewole hosts Winners Circle With Jay, a business show with 104 episodes published.

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  Episode #8

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

  Sep 30, 202656 minS6

  Fear gets loud at 35,000 feet. Jay Adewole sits down with aviator, author, businessman, and global adventurer Robert DeLaurentis, known as the Zen Pilot and the Peace Pilot, for a powerful conversation about flying through fear, leading with purpose, and staying committed when the mission is bigger than the risk. Robert shares the mindset that carried him through solo circumnavigations of the planet, including brutal moments over the North Pole, emergency landings, and a terrifying fuel spill in Dakar that could have ended everything. But this episode is not just about aviation — it is about what it takes to keep going when you are alone, under pressure, and forced to make decisions with no room for panic. You’ll discover: How Robert prepares for major flights by identifying and mitigating risk long before takeoff Why he believes the checklist is one of the most powerful leadership tools in business What his near-death moments taught him about clarity, courage, and execution How silence, solitude, and inner peace become assets instead of obstacles Why fear should be faced, written down, and systematically eliminated How he built a mission around aviation, philanthropy, education, and world peace Robert also opens up about the deeper purpose behind the Citizen of the World aircraft, the DeLaurentis Foundation, his books, his films, and the airport projects designed to inspire the next generation. From kids staring up at planes to entrepreneurs building alone, this conversation makes the case that noble purpose changes everything.If you are leading a team, building a business, chasing a calling, or just trying to stay steady in turbulent seasons, this episode will challenge you to think bigger, prepare better, and move forward with more courage than fear. Essential listening if you need a reminder that the mission matters, and that peace begins within. #Winnerscircle #Aviation #Leadership #Entrepreneurship #OvercomingFear #PersonalDevelopment #PurposeDriven #PilotLife #BusinessLeadership #Inspiration

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  Episode #7

  The 60-Second Elevator Speech Every Entrepreneur Needs

  Sep 23, 202642 minS6

  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

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  Episode #6

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

  Sep 16, 202639 minS6

  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 it How to tell whether you need a web app, mobile app, or no app at all Why AI-powered “vibe coding” is useful for proof of concept, but not enough for scalable products The biggest red flags to watch for when hiring a software developer or technology partner How custom technology can help service businesses become more valuable, more profitable, and more sellable Why the businesses that win over the next five years will be the ones that adopt AI, agents, and automation now Ghazenfer 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.

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  Episode #5

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

  Sep 9, 202633 minS6

  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

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  Episode #4

  Why Hourly Billing Is Broken in the AI Era

  Sep 2, 202643 minS6

  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

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