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CEOs Unscripted

CEOs Unscripted

Written by: Jane Gentry
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 Real Talk. Real Growth. Real Results in the Mid-Market Jane Gentry consulted in enterprise for 20 years. And, after being a CEO in a mid-sized company, she realized why they say it is loneliest at the top. Mid-market CEOs learn their craft through trial and error or by reaching outside their organization for help. She launched CEOs Unscripted as a bi-weekly podcast by mid-market CEOs for mid-market CEOs. Our purpose is to provide insight into the unscripted, unfiltered journeys of CEOs and Founders as they talk about their wins, losses, lessons and playbooks for growing and scaling their organizations. There is no better forum than learning from your peers.Copyright 2025 All rights reserved. Economics Leadership Management Management & Leadership
Episodes
  • How to Navigate Private Equity Deals: IAA CEO's $7.5 Billion Journey

    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

    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)

    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
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