• How to Navigate Private Equity Deals: IAA CEO's $7.5 Billion Journey
    Jan 6 2026

    Former IAA CEO John Kett shares his remarkable 22-year journey building a damaged vehicle marketplace from $200 million to $7.5 billion through multiple PE transactions, public offerings, and a major merger. This unfiltered conversation covers private equity strategies, M&A lessons, and what it really takes to scale mid-market companies.

    In this episode, John reveals: ✅ The truth about working with private equity firms ✅ How to prepare your company for a PE sale ✅ Why technology should enable process, not the other way around ✅ Navigating the complexity of public vs. private company leadership ✅ Board meeting preparation strategies that actually work ✅ The cost of short-term thinking in PE-backed companies

    KEY TIMESTAMPS: 00:00 - Introduction 02:45 - John's Blue Collar Background & Path to CEO 05:30 - What is a Damaged Vehicle Marketplace? 09:15 - The IAA Business Model Explained 12:40 - First Exposure to Private Equity 16:20 - Preparing Your Company for PE Sale 19:45 - Working with Multiple PE Firms (The Four-Headed Monster) 24:10 - PE Time Horizons & Their Impact on Decisions 28:35 - Board Meeting Preparation Best Practices 32:15 - The Importance of Cross-Collaboration Among Leaders 35:40 - From Private to Public: The Spinoff Story 38:50 - The $7.5B Merger with Ritchie Brothers 42:20 - Rapid Fire: Career Lessons & Leadership Wisdom 45:10 - Why In-Person Leadership Development Matters

    ABOUT JOHN KETT: Former CEO of IAA (Insurance Auto Auctions), John Kett led the company through multiple transformations including PE acquisitions, public listings, and ultimately a $7.5 billion merger with Ritchie Brothers. With over 22 years of experience scaling mid-market companies, John now advises CEOs and serves on boards.

    ABOUT CEOS UNSCRIPTED: Real talk for mid-market leaders. Host Jane Gentry brings you unfiltered conversations with CEOs, founders, and executives navigating the challenges of scaling $10M-$500M businesses. No fluff, no jargon—just honest insights from leaders who've been where you are.

    SUBSCRIBE for bi-weekly episodes featuring: → Private equity strategies → M&A insights → Scaling best practices → Leadership development → Board governance → Exit planning

    TAGS: #PrivateEquity #CEO #MergersAndAcquisitions #BusinessGrowth #Leadership #ScalingBusiness #PEInvesting #BoardMeetings #ExitStrategy #MidMarketCEO #BusinessPodcast #Entrepreneurship #CorporateDevelopment #BusinessStrategy

    What's your biggest question about working with private equity? Drop it in the comments below!

    👍 Like this video if you found it valuable 🔔 Subscribe for more CEO insights 📤 Share with other business leaders

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    47 mins
  • 500 Remote Employees, Zero Office Space: The Anti-Traditional Playbook
    Dec 23 2025
    In this powerful episode of CEOs Unscripted, host Jane Gentry sits down with Brad Stevens, founder and CEO of Outsource Access, to explore his remarkable journey from serial entrepreneur to building a 500-person remote workforce in the Philippines—all while navigating a global pandemic. 📍 TIMESTAMPS: 00:00 - Introduction: Brad Stevens & Outsource Access 02:15 - The Entrepreneurial Origin Story: Third Grade Micro Machines Business 05:30 - Wharton to Unemployment: The $20K Signing Bonus Plot Twist 08:45 - First Company: Patient Assistance Programs for Seniors 11:20 - The Nutritional Supplements Journey 13:40 - Teeth Whitening Product Fiasco: 10,000 Units, 18 Countries 16:25 - Discovering Outsourcing & Launching Outsource Access in 2019 19:10 - Growing to 500 Employees in 4.5 Years Across 85 Industries 22:30 - Launching Right Before COVID: Building Remote Culture from Day One 25:45 - EOS Framework: The System That Prevented Implosion 28:20 - Jim Collins' Level 5 Leadership in Practice 30:50 - Writing Personal Welcome Messages to Every New Hire 33:15 - Virtual Leadership: Intentional Communication & Cadence 36:40 - The Five Chronological Steps Framework 39:20 - Building Culture Remotely: Virtual Success Magazine & UN Goals 42:10 - Employee Engagement: Recognition, Purpose, and Autonomy 44:50 - "What Got You Here Won't Get You There": Scaling Challenges 47:30 - Ferrari Intensity vs. Cargo Ship Reality: Managing Growth Speed 50:15 - The 2-Question Exercise That Reveals Business Constraints 52:40 - The 90-Day Onboarding Process & Playbook Creation 55:20 - Rapid Fire: Reading List, Early Lessons & Advice for Young Leaders 57:30 - Closing Thoughts What You'll Learn: The Remote Leadership Framework - How to build culture, maintain communication, and drive performance with 500 employees in another country Scaling Without Implosion - The systems, frameworks, and leadership principles that enabled 4.5 years of hypergrowth The Onboarding Advantage - Why most companies fail at onboarding and Brad's 90-day playbook that actually works Level 5 Leadership in Action - Practical applications of Jim Collins' principles for mid-market CEOs Key Takeaways for Mid-Market CEOs: ✅ The EOS framework combined with Four Disciplines of Execution creates accountability and clarity ✅ Recognition matters more than you think—Brad spends 10-15 hours monthly writing personal welcome messages ✅ The 2-question exercise that reveals your biggest business constraints in one survey ✅ Why onboarding takes 90 days (not 2 weeks) and how to structure it for success ✅ Ferrari intensity doesn't work with cargo ship reality—managing expectations during hypergrowth Featured Topics: Remote workforce managementPhilippines outsourcing strategyEOS implementationVirtual leadership during COVIDOnboarding frameworksAssessment tools (Predictive Index, CliftonStrengths)Level 5 LeadershipDecision velocityBusiness process documentationAI integration for remote teamsEntrepreneurial Operating SystemCulture building remotelyStrategic focus vs. diversificationLeadership developmentScaling challenges Whether you're managing remote teams, scaling rapidly, or struggling with onboarding, this episode delivers battle-tested frameworks from a CEO who grew 500 employees across the world during a pandemic. RESOURCES MENTIONED: Books & Frameworks: Good to Great by Jim CollinsBuilt to Last by Jim CollinsThe Four Disciplines of Execution by Stephen Covey21 Irrefutable Laws of Leadership by John MaxwellWho Not How by Dan SullivanThe Four-Hour Work Week by Tim FerrissPredictable Success by Les McKeownAlex Hormozi content and programs ABOUT THE GUEST: Brad Stevens is the founder and CEO of Outsource Access, a company that helps small to medium-sized businesses integrate talented offshore staff from the Philippines to drive scale and profitability. Since launching in 2019, Brad has grown the company to 500 employees across 85 different industries, building a distributed workforce model before the pandemic made it necessary. A Wharton graduate and serial entrepreneur for 25 years, Brad has built and sold companies in pharmaceuticals, nutritional supplements, teeth whitening products, and now outsourcing. He's a 14-year member of EO (Entrepreneurs' Organization) and served as President of EO Atlanta. Brad is passionate about level 5 leadership, systematic onboarding, and proving that remote teams can build exceptional culture and deliver outstanding results. ABOUT CEOS UNSCRIPTED: CEOs Unscripted is a bi-weekly podcast by mid-market CEOs, for mid-market CEOs. Host Jane Gentry brings 20+ years of enterprise consulting experience and firsthand CEO leadership to deliver unfiltered conversations about what it really takes to scale, lead, and win in today's business landscape. No fluff. No jargon. Just real talk that drives real growth. Subscribe for new episodes every other week! 💬 JOIN THE CONVERSATION: What's your biggest challenge with remote team management or ...
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    58 mins
  • AI Is Killing the Agency Model (And How We're Using It to Win)
    Dec 10 2025
    In this compelling episode of CEOs Unscripted, host Jane Gentry sits down with Raj Choudhury, founder of Alloy Marketing and Purpose Group PE, to explore how purpose-driven leadership and strategic AI adoption are reshaping mid-market companies. 📍 TIMESTAMPS: 00:00 - Introduction: From Uganda to Atlanta - Raj's Journey 03:45 - The Two Tracks: S1 (Blue-Collar Businesses) vs S2 (Agency Platform) 08:20 - What is The Purpose Playbook Framework? 12:15 - Open-Book Management: Why Transparency Wins 17:30 - The Four-Bucket Goal Framework (People, Quality, Brand, Financials) 23:45 - How AI is Disrupting the Agency Business Model 28:10 - Agentic Roles: The Future of Service Industries 33:25 - The Grieving Process: Managing AI-Driven Change 38:40 - Why Engineers Shouldn't Do Sales (And Other CEO Blind Spots) 42:15 - Creating Safe Environments for AI Experimentation 46:30 - Legal and Security Considerations for AI Implementation 51:20 - The Great Game of Business Integration 55:10 - Building Context in a Social Media World 58:45 - Naivety as a Superpower in Business 1:01:30 - The Language of Business is Numbers 1:03:15 - The 8-Minute Rule: When to Stop and Reset 1:05:45 - Final Thoughts and Where to Connect What You'll Learn: 🎯 The Purpose Playbook Framework - How open-book management and transparent goal-setting create employee engagement and drive sustainable growth in blue-collar businesses 💡 AI Implementation Strategy - Moving beyond tools to transform business models: Why agentic roles are disrupting the traditional services industry and how to prepare your team 📊 Breaking the Linear Growth Model - How AI is enabling agencies and service businesses to scale revenue without proportionally increasing headcount 🔄 Change Management in the AI Era - The "grieving process" employees need when core skills become automated, and how to guide teams through transformation Key Takeaways for Mid-Market CEOs: ✅ The four-bucket framework (People & Product, Quality, Brand Awareness, Financials) that aligns every role from C-suite to shop floor ✅ Why gamification and context matter more than compensation in driving performance ✅ How to implement AI tools within established methodologies rather than letting technology dictate your processes ✅ The critical difference between building for income versus building for wealth when positioning for exit Featured Topics: - Private equity strategies for blue-collar businesses - Open-book management and financial transparency - Conscious capitalism in practice - Agency business model disruption - Agentic AI and synthetic roles - Employee engagement through shared purpose - Strategic change management - M&A insights for service businesses Whether you're scaling a mid-market company, implementing AI initiatives, or exploring PE opportunities, this episode delivers actionable frameworks and unfiltered insights from a CEO who's been in the trenches. 📚 RESOURCES MENTIONED: The Purpose Playbook: The Definitive Guide to Building Your Team's Purpose, Vision, Tenets, & Values (PVTV) By Jeff Hilimire, Teresa Caro, and Megan Barney Companion guide to the Turnaround Leadership Series Tools & Frameworks Mentioned: Writer.ai (AI-powered editing tool) Google Gemini / Notebook LM The Great Game of Business by Jack Stack RACI Matrix for decision-making 13-Week Cash Flow Forecasting 🔗 Purpose Group Newsletter: purposegroup.substack.com 👤 ABOUT THE GUEST: Raj Choudhury is the founder of Alloy, a marketing agency serving mid-market technology brands, and Purpose Group, a PE firm focused on acquiring and transforming blue-collar businesses. With his partner Jeff Hilimire and co-founder David Cummings, Raj implements the Purpose Playbook framework across their portfolio companies, including Gerald Printing & Liberty Imaging. With 25 years of experience in M&A within the agency space, Raj brings unique insights into building sustainable, people-first organizations that scale profitably. ABOUT CEOs UNSCRIPTED: CEOs Unscripted is a bi-weekly podcast by mid-market CEOs, for mid-market CEOs. Host Jane Gentry brings 20+ years of enterprise consulting experience and firsthand CEO leadership to deliver unfiltered conversations about what it really takes to scale, lead, and win in today's business landscape. No fluff. No jargon. Just real talk that drives real growth. Subscribe for new episodes every other week!
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    1 hr
  • How This CEO Built a $160M Firm While Staying 100% Independent | Thomas Grealish
    Nov 26 2025
    In this powerful episode of CEOs Unscripted, host Jane Gentry sits down with Thomas Grealish, leader of Henderson Brothers, one of Pittsburgh's most respected independent insurance and financial services firms with over 160 employees. What You'll Learn: 🔹 Culture as Competitive Advantage - How Henderson Brothers protects their independence and uses culture to naturally "weed out" bad fits while attracting top talent 🔹 The Stay Interview Strategy - Why Thomas asks employees two critical questions about leaving (before they ever consider it) and how this prevents turnover 🔹 Hiring Without Mistakes - The "messy but effective" referral-based hiring process that prioritizes cultural fit over impressive resumes 🔹 The Two-Minute Drill - Thomas's crisis preparation exercise that helped his team navigate the 2008 financial crisis, tech bubble, and COVID without panic 🔹 Financial Transparency That Works - How sharing P&L statements weekly creates ownership mentality across the entire organization 🔹 Strategic Growth Done Right - Expanding to Columbus, Ohio organically while maintaining culture remotely 🔹 Community Giving as Leadership Development - Why Thomas encourages 30-year-olds to join nonprofit boards and how Henderson Brothers supports employee philanthropy 🔹 Family Business Survival - Navigating 40+ years in a family business with his brother while maintaining alignment on vision and values Key Timestamps: 00:00 - Introduction & Pittsburgh Culture 04:32 - Culture as Everything: Independence & Heroic Service 09:15 - The Stay Interview: Two Questions Every CEO Should Ask 14:20 - Hiring Process: Slow, Careful & Referral-Based 18:45 - The Two-Minute Crisis Drill That Prepares Teams 23:10 - Financial Transparency & Weekly P&L Sharing 28:30 - Operationalizing Culture as You Scale 33:15 - Community Philanthropy & Developing Young Leaders 38:40 - The Mario Lemieux Foundation Story 42:20 - Strategic Expansion to Columbus, Ohio 46:15 - Family Business: Alignment & Good Intent 51:30 - Rapid Fire: Books, Career Advice & Getting Unstuck About Thomas Grealish: Thomas has led Henderson Brothers for decades, growing it into a major regional insurance and financial services firm while maintaining private ownership and a culture-first approach. He serves on multiple nonprofit boards including the Mario Lemieux Foundation and is a Duquesne University graduate deeply committed to the Pittsburgh community. About CEOs Unscripted: CEOs Unscripted is a bi-weekly podcast by mid-market CEOs for mid-market CEOs. Host Jane Gentry, a veteran consultant and former mid-market CEO herself, delivers unfiltered conversations with founders and executives navigating the unique challenges of leading $10M-$500M companies. No fluff, no jargon—just real talk that drives real growth. Subscribe for More Leadership Insights: New episodes drop bi-weekly featuring candid conversations with CEOs who've scaled businesses, navigated crises, and built lasting organizations. Tags: CEO leadership, company culture, mid-market business, family business, hiring strategy, organizational development, business growth, Pittsburgh business, insurance industry, leadership podcast, executive coaching, crisis management, corporate culture, talent retention, strategic planning, employee engagement, business scaling, CEO interview, entrepreneurship, business strategy, workplace culture, leadership development, talent management, business expansion, independent business, private company, heroic service, stay interviews, financial transparency, nonprofit leadership, community impact, succession planning, organizational culture, CEO advice, business podcast, executive leadership, team building, business management, regional growth, family business leadership Related Topics: #CEOLeadership #CompanyCulture #MidMarketBusiness #FamilyBusiness #HiringStrategy #OrganizationalDevelopment #BusinessGrowth #PittsburghBusiness #InsuranceIndustry #LeadershipPodcast #ExecutiveCoaching #CrisisManagement #CorporateCulture #TalentRetention #StrategicPlanning #EmployeeEngagement #BusinessScaling #Entrepreneurship #WorkplaceCulture #LeadershipDevelopment Listen now and discover how one CEO built a $160M+ firm without sacrificing culture, independence, or community impact.
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    58 mins
  • How to Fix Your Hiring Process: CEO Reveals Why You're Losing Top Talent | Executive Search Expert
    Nov 11 2025

    Struggling to find and retain top talent? You're not alone. In this episode of CEOs Unscripted, I sit down with Brandt Handley from ROI Executive Search to uncover why most mid-market companies are getting hiring ALL WRONG.

    What You'll Learn: ✅ Why the traditional interview process is fundamentally broken ✅ Cultural fit vs qualifications: What ACTUALLY matters in hiring ✅ The true cost of a bad hire (3-4x annual salary!) ✅ How to create an effective onboarding process that retains talent ✅ Why hiring "mini-me's" destroys innovation and growth ✅ The power of psychographic assessments in talent acquisition ✅ When CEOs should step back from day-to-day operations

    Book Mentioned:

    A Whole New Mind: Why Right-Brainers Will Rule the Future

    Featured Expert: Brandt Hanley brings 21+ years of executive search experience, previously working with Procter & Gamble and Walt Disney Company across international markets.

    Perfect for:

    • Mid-market CEOs and founders
    • HR professionals and talent acquisition teams
    • Business leaders struggling with employee retention
    • Companies experiencing rapid growth
    • Anyone responsible for building high-performing teams

    💡 The biggest takeaway? Stop hiring for tenure and start hiring for cultural fit and giftedness. In today's market where average tenure is just 4 years, the old rules no longer apply. KEY TIMESTAMPS: 00:00 - Introduction & Welcome to CEOs Unscripted 02:30 - Brandt's Background: From P&G to Disney to Executive Search 08:45 - Why Mid-Market CEOs Struggle with Talent Acquisition 12:20 - The Broken Interview Process 15:40 - Cultural Fit vs Qualifications: What Really Matters 19:15 - The Age Discrimination Problem in Hiring 23:50 - Finding Your True Gifts vs Following Passion 27:30 - The Power of Psychographic Assessments 31:45 - The Cost of Impatience in Hiring (3-4x Salary!) 36:20 - Understanding Your Company Culture Before Hiring 40:15 - The MBA Myth: Why Degrees Don't Guarantee Success 43:50 - Hiring for Different Stages of Company Growth 47:25 - The "Mini-Me" Mistake: Why Diversity Matters 52:10 - The Importance of Professional Reference Checks 55:40 - Onboarding: The Missing Link in Talent Retention 58:30 - The Inverted Pyramid Leadership Model 61:45 - Rapid Fire Questions & Final Wisdom

    🔔 Subscribe to CEOs Unscripted for bi-weekly conversations with real CEOs sharing unfiltered insights on leadership, growth, and scaling mid-market companies.

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    1 hr and 4 mins
  • The Hidden Crisis Behind Your 5G: A CEO's Mission to Save the Telecom Workforce
    Oct 29 2025

    In this compelling episode of CEOs Unscripted, host Jane Gentry sits down with Letizia Latino, CEO of Neptune USA, to explore the unique challenges of leading in the telecommunications infrastructure industry. From managing the boom-and-bust cycles of wireless construction to championing workforce development through apprenticeships, Letizia shares her unfiltered insights on modern business leadership.

    What You'll Learn:

    ✅ Industry Challenges & Innovation:

    - The "all-you-can-eat buffet or starvation" reality of the telecom industry - How AI and drone technology are revolutionizing tower inspection and engineering - Navigating tariff impacts and supply chain complexities in steel manufacturing - The critical infrastructure behind your cell phone connectivity

    ✅ Workforce Development & Talent:

    - Why apprenticeship programs are the future of skilled labor - The untapped potential of hiring military veterans in technical roles - How to retain skilled workers during industry downturns - Breaking the stigma around trade jobs vs. four-year degrees

    ✅ Leadership Lessons:

    - Overcoming "we've always done it this way" resistance to change - Managing change initiatives effectively through transition periods - The importance of staying curious and aligned with your values - Balancing family business legacy with personal identity

    ✅ Change Management Insights:

    - Why most growth initiatives fail (hint: it's not the strategy) - The critical role of middle managers in executing change - Using AI to predict resistance to organizational change - Communication strategies that actually work

    ✅ Featured Topics & Keywords:

    Telecommunications CEO | Women in Leadership | Wireless Infrastructure | Tower Construction | Change Management | Workforce Development | Apprenticeship Programs | Veterans Employment | AI in Business | Drone Technology | Digital Twin Technology | Supply Chain Management | Tariff Impact | Business Strategy | Family Business | CEO Challenges | Trade Jobs | Skills Gap | Construction Industry | 5G Infrastructure | Telecom Innovation | Leadership Development

    Guest Bio:

    Letizia Latino is the CEO of Neptune USA, a telecommunications infrastructure company specializing in steel tower manufacturing and engineering services. Born in Venezuela to Italian immigrant parents, Letizia brings an international perspective to business leadership. Before joining the family business, she gained experience at Merrill Lynch and Nortel Networks. She's passionate about workforce development, serves on several FCC committees, and hosts the podcast "Back to Basics: Reconnecting to the Essence of You."

    Timestamps:

    00:00 Introduction & Letizia's International Background 05:30 The Path from Corporate to Family Business 12:15 The "Buffet or Starvation" Challenge in Telecom 18:45 Innovation Through AI & Drone Technology 25:20 Change Management & Status Quo Resistance 32:10 Tariff Impacts & Manufacturing Challenges 38:00 Apprenticeship Programs & Trade Education 45:30 Hiring Veterans in Technical Roles 52:00 Rapid Fire Questions 58:30 Final Thoughts & Future Goals

    About CEOs Unscripted:

    CEOs Unscripted is a bi-weekly podcast by mid-market CEOs for mid-market CEOs, hosted by Jane Gentry. Each episode delivers unfiltered, behind-the-scenes conversations about the wins, losses, and real-world strategies of leading and scaling businesses in today's dynamic landscape.

    Subscribe for more conversations with CEOs who are changing the game.

    SEO Tags:

    #CEOPodcast #BusinessLeadership #TelecommunicationsIndustry #ChangeManagement #WorkforceDevelopment #WomenInBusiness #ApprenticeshipPrograms #VeteransEmployment #AIInBusiness #DroneInnovation #ConstructionIndustry #CEOInterview #LeadershipPodcast #BusinessStrategy #FamilyBusiness #TowerConstruction #WirelessInfrastructure #TradeJobs #SkillsGap #BusinessInnovation

    Category: Business | Entrepreneurship | Leadership | Technology | Telecommunications

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    50 mins
  • The $50M Exit Blueprint: How a Blue-Collar Kid Built & Sold an International Business
    Oct 16 2025

    What happens when a blue-collar kid from South Jersey transforms into a business-scaling expert? In this episode of CEOs Unscripted, host Jane Gentry sits down with her longtime mentor and business partner Pat Alacqua to uncover the raw truth about entrepreneurial growth, leadership transformation, and the psychological barriers that keep founders stuck. Pat shares his remarkable journey from working at his grandfather's grocery store to co-founding and scaling a trade show services company (The Nth Degree) into an international operation before successfully exiting in 2001. But this isn't just a success story—it's a masterclass in the messy, challenging reality of business growth. What You'll Learn: - The critical psychological shift from "doer" to leader and why most entrepreneurs struggle with it - How to manage your business by assumptions instead of budgets or checklists - The five distinct phases every company must navigate from startup to enterprise - Why spawning competitor companies from your best employees isn't always bad - The importance of having "one foot in the present and one foot in the future" - Practical strategies for identifying and addressing blind spots in your leadership. Key Insights: ✓ The three psychological barriers preventing delegation: identity, control, and validation ✓ Why "what got you here won't get you there" applies to every growth stage ✓ How to earn the right to keep things simple by first understanding complexity ✓ The power of assumption-based planning in uncertain markets ✓ Why asking the right questions matters more than having all the answers Whether you're a mid-market CEO navigating growth challenges, an entrepreneur struggling to scale, or a business leader looking to avoid common pitfalls, this conversation delivers actionable frameworks you can implement immediately. Book: Obstacles to Opportunity: Transforming Business Challenges into Triumphs https://tinyurl.com/5fr8fhy2 About the Guest: Pat Alacqua is a business growth strategist with over 40 years of experience building, scaling, and exiting companies. After co-founding and growing a trade show services company from startup to international operation, Pat now partners with CEOs to help them navigate the complex transitions from entrepreneur to enterprise leader. About the Host: Jane Gentry brings 20+ years of enterprise consulting experience and firsthand CEO leadership to CEOs Unscripted, creating a space where mid-market leaders share unfiltered stories, practical playbooks, and hard-won wisdom. 🔔 Subscribe to CEOs Unscripted for bi-weekly conversations with founders and executives who've navigated the challenges you're facing. 💬 Join the Conversation: What's your biggest challenge in transitioning from doer to leader? Share in the comments below. Timestamps: 00:00 - Introduction: Meet Pat Alacqua 03:15 - Growing up in small business: Early influences and work ethic 07:42 - From concrete business to trade shows: The entrepreneurial journey 12:30 - Navigating union labor and legal battles while scaling 16:45 - Building systems and the art of working ON vs. IN your business 21:20 - The painful reality of becoming the bottleneck in your own business 25:10 - Three psychological barriers to delegation: Identity, control, and validation 30:15 - Understanding business life cycles and the entrepreneur-to-enterprise journey 35:40 - The five phases of business growth every CEO must master 40:25 - Managing by assumptions vs. managing by budgets 45:30 - Solving root cause problems instead of applying band-aids 48:50 - Modeling leadership behavior and developing your team 52:15 - The importance of blind spots and continuous learning 56:40 - Earning the right to keep things simple 01:00:20 - The science and art of building effective systems 01:03:45 - Rapid fire questions: Books, early lessons, and advice for young professionals 01:08:30 - What to do when you get stuck as a leader 01:11:15 - Closing thoughts and key takeaways Tags #CEOsUnscripted #BusinessGrowth #LeadershipDevelopment #Entrepreneurship #ScalingBusiness #MidMarketCEO #BusinessStrategy #LeadershipTransformation #BusinessSystems #CEOPodcast #BusinessPodcast #ExecutiveLeadership #BusinessScaling #DelegationSkills #BusinessProcesses #StrategicLeadership #CompanyGrowth #BusinessMentor #EntrepreneurialGrowth #LeadershipMindset #BusinessLifeCycle #BusinessExit #SmallBusinessGrowth #MidMarketLeaders CEOs Unscripted is a bi-weekly podcast by mid-market CEOs for mid-market CEOs, delivering unfiltered conversations about what it takes to lead, grow, and scale in today's business landscape.

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    54 mins
  • AI Strategy for Mid-Market CEOs: How to Start, Scale & Succeed Without Getting Left Behind | Chris Happ
    Oct 1 2025

    Is AI overwhelming your mid-market business? You're not alone. In this unfiltered episode of CEOs Unscripted, host Jane Gentry sits down with Chris Happ, CEO of Virtuous AI and serial entrepreneur, to break down exactly how mid-market CEOs should approach AI strategy—without the tech jargon or corporate bureaucracy.

    What You'll Learn:

    ✅ Why AI is a STRATEGIC initiative, not an IT project ✅ How to identify the right business problem to solve with AI first ✅ The MIT study revealing why 95% of Fortune 500 AI pilots fail ✅ Why mid-market companies have a competitive advantage over enterprise ✅ How to manage AI as a change initiative (and avoid employee resistance) ✅ Real case studies: inventory optimization, workflow automation, and BI transformation ✅ The critical mistake of "bolting on" AI tools that create more silos ✅ How to protect your competitive advantage and proprietary data ✅ Why you should never wait to start experimenting with AI

    Key Takeaways:

    🔹 Start with ONE meaningful business problem (growth, profitability, or retention) 🔹 AI can clean your dirty data BEFORE you even begin analysis 🔹 You don't need a massive budget—nimbleness is your superpower 🔹 Think "revenue per head" metrics (target: $1M per employee) 🔹 Avoid the subscription trap—consolidate around strategic platforms 🔹 Your AI strategy should be owned by the CEO, not delegated to IT

    Perfect For: Mid-market CEOs, founders, business leaders navigating digital transformation, operations executives, and anyone feeling overwhelmed by the AI landscape.

    Guest: Chris Happ is the CEO of Virtuous AI and a proven mid-market CEO who has successfully sold multiple companies. He specializes in helping businesses implement AI strategically without the enterprise complexity.

    Timestamps: 0:00 - Introduction: Why AI is overwhelming mid-market CEOs 2:34 - The MIT study: 95% of Fortune 500 AI pilots fail 5:38 - AI as a change initiative, not just technology 8:59 - Why mid-market CEOs have the advantage 12:33 - Predictive vs deterministic AI explained simply 15:48 - Start with a business problem, not the technology 19:10 - Case study: AI-powered inventory optimization 21:42 - The dirty data problem and how AI solves it 27:09 - Common mistakes and opportunities 33:35 - The subscription model trap killing mid-market budgets 40:18 - AI for business intelligence and real-time reporting 44:44 - Critical cautions: protecting your competitive advantage 49:58 - What happens if you need to switch vendors? 55:32 - Final takeaways and next steps

    Resources Mentioned:

    • MIT Fortune 500 AI Study
    • Virtuous AI Platform (BAYO - Business Automation Intelligence & Outcomes)

    📌 Don't get left behind—subscribe for more candid conversations with CEOs who've been where you are!

    Hashtags: #AIStrategy #MidMarketCEO #BusinessTransformation #AIForBusiness #CEOPodcast #DigitalTransformation #BusinessAutomation #AIImplementation #LeadershipPodcast #CEOInsights #ArtificialIntelligence #ChangeManagement #BusinessGrowth #VirtuousAI #CEOsUnscripted

    About CEOs Unscripted: CEOs Unscripted is a bi-weekly podcast by mid-market CEOs, for mid-market CEOs. Host Jane Gentry brings 20+ years of consulting experience and firsthand CEO leadership to deliver unfiltered conversations about what it really takes to lead, grow, and scale a business. No fluff. No jargon. Just real talk that drives real results.

    🔔 Subscribe and hit the notification bell to never miss an episode! 💬 What's your biggest AI challenge? Drop it in the comments below!

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    57 mins