The Digital Transformist

Michael LaVista
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Welcome to The Digital Transformist, where we empower CEOs to lead their companies through digital transformation with confidence and clarity. If you’re a CEO of a midsize company between $100 million and $250 million in revenue or have those companies in your portfolio, and your goal is to create enterprise scale and exit, this podcast is your essential guide to leveraging technology for growth.Join us each week as we dive deep into the world of digital transformation, focusing on non-tech-enabled industries like manufacturing, construction, and distribution. We also extend our expertise to private equity and M&A firms, providing actionable strategies to drive digital excellence across investments, optimizing for both growth and exit.Whether you’re already on the path to digital success or facing obstacles in your journey, our interviews with CEOs provide valuable insights, practical advice, and inspiring stories.Discover how successful leaders are removing friction from their businesses, implementing innovative solutions, and driving tangible results. From overcoming challenges to seizing opportunities, The Digital Transformist offers actionable strategies for every stage of your digital transformation journey.

  1. 1d ago

    AI doesn't fail. Leadership does.

    What if your AI initiatives are failing not because of the technology, but because your leadership approach is fundamentally broken? Teri Hill drops a startling statistic: 44% of Gen Z employees are intentionally sabotaging AI rollouts—and the reason why should worry every CEO. In this episode, you'll discover why 70% of strategies fail at execution, how to measure the five keys to successful transformation, and why operational excellence through AI requires rethinking your entire approach to leadership and culture. Teri breaks down the hidden costs of disengagement (hint: it's $10 trillion annually) and reveals why documenting SOPs is just the beginning—the real opportunity is reimagining your processes entirely. Teri Hill is CEO of Hill Summit and former Managing Director of Strategy at Accenture, where she spent over a decade leading global transformation initiatives. She now helps small and mid-sized companies bridge the execution gap that large consultancies can't address. If you're rolling out AI or rethinking your operations, this episode will change how you lead. Subscribe for more insights on doing AI the right way. Chapters: 00:00 - Intro 01:13 - From Big Consulting to Serving SMBs 02:17 - Why 70% of Strategies Fail 04:42 - SOPs and the AI Documentation Surge 08:10 - Challenge the Process or Fall Behind 09:45 - The Gen Z Workforce Crisis 11:28 - Job Elimination vs. Job Enhancement 13:52 - Measuring Success with Line of Sight 16:23 - Building Leadership That Lasts 18:47 - The Future of Work and AI Get Mike's book "Superpowered" on Amazon: https://www.amazon.com/dp/B0F1Y2M3X4 Caxy Interactive -- Showing organizations how to play offense with technology. https://www.caxy.com | hello@caxy.com

    AI doesn't fail. Leadership does.

  2. Oct 28

    Are You Invisible to AI?

    What if your decades of expertise mean nothing because AI can't find you? Ashley Smith reveals a stunning truth: even seasoned executives with elite networks are becoming invisible as AI search rewrites the rules of discovery and trust. In this episode, visibility strategist Ashley Smith breaks down the "proof gap"—the dangerous disconnect between your real-world reputation and what actually shows up when someone searches for you online. You'll learn why Google's shift away from the "10 blue links" model means traditional SEO is dying, how LLMs decide who gets recommended (and who gets ignored), and practical strategies that don't require building an audience or spending hours on social media. Ashley shares why being cited by trusted sources matters more than ever and how executives can leverage their existing networks to close the visibility gap before it costs them opportunities. Ashley Smith is a visibility strategist with nearly 20 years of entrepreneurial experience in legacy sectors, helping professionals and executives translate real-world authority into online discoverability. If you're leading a mid-sized company and wondering why your expertise isn't translating online, this episode is your wake-up call. Subscribe for more insights on winning with digital transformation. Chapters: 00:00 - Intro 00:49 - What Is a Visibility Strategist? 02:56 - The Proof Gap Explained 06:16 - The Cost of Being Invisible Online 09:52 - How AI Search Is Changing Discovery 13:03 - Getting Cited by Trusted Sources 18:54 - LinkedIn Profile Optimization Tactics 26:11 - Building Authority Without an Audience 32:45 - Practical Steps for Busy Executives Get Mike's book "Superpowered" on Amazon: https://www.amazon.com/dp/B0F1Y2M3X4 Caxy Interactive -- Showing organizations how to play offense with technology. https://www.caxy.com | hello@caxy.com

    Are You Invisible to AI?

  3. Oct 21

    When AI Breaks More Than It Fixes

    AI can write code faster than ever. But what happens when that speed comes at the cost of smarter decisions? In this episode of The Digital Transformist, host Michael LaVista sits down with CTO Josh Deason-Schroeder to explore the hidden risks of AI-assisted development and why faster coding doesn't always mean better software. Drawing from real-world experience, Josh breaks down how AI can steer developers toward short-term fixes, create costly architectural decisions, and introduce more bugs than it solves. He shares why even the most advanced AI tools still need human oversight and how developers can avoid building themselves into a corner. From technical debt to technology lock-in, this conversation explores what happens when teams rely too heavily on AI and why understanding your own code is more important than ever. If you're building software with AI or leading a development team, this episode is a must-watch. Subscribe for more conversations on the realities of AI, technology, and digital transformation. Chapters: 00:00 - Intro 00:43 - When AI First Appeared on the Radar 01:58 - The Honeymoon Phase and Early Disappointments 03:46 - Learning AI as a Student vs Expert 06:06 - Where AI Falls Short in Strategy 07:48 - Architecture Decisions and Technology Lock-In 10:36 - The Supabase Example and Refactoring Costs 12:58 - Setting Up Infrastructure with AI Tools 15:24 - Code Review and Quality Control Challenges 19:15 - Testing Limitations and Security Concerns 22:40 - When to Use AI vs Human Judgment 25:30 - Future of AI in Software Development Get Mike's book "Superpowered" on Amazon: https://www.amazon.com/dp/B0F1Y2M3X4 Caxy Interactive -- Showing organizations how to play offense with technology. https://www.caxy.com | hello@caxy.com

    When AI Breaks More Than It Fixes

  4. Oct 14

    Why AI Fails in the Real World

    Your AI works perfectly in testing. So why does it fall apart in the real world? Matt Soltau, Global Director of Strategy and Operations at Intelliphas, joins The Digital Transformist to reveal why even the most promising AI projects fail when they move from concept to production. From an AI-powered call center in Singapore confidently giving customers incorrect information to companies still relying on printing, scanning, and emailing documents in 2026, Matt exposes the hidden data and infrastructure problems holding businesses back. In this episode, we explore: - Why AI succeeds in a sandbox but fails in production - How poor data integration can derail even the smartest AI solutions - Why outdated systems and disconnected data create expensive bottlenecks - The hidden security risks of citizen developers - How to balance AI innovation with governance and compliance Matt brings real-world experience from regulated industries to explain why successful AI transformation isn't just about the technology. It's about building the right foundation. If your organization is investing in AI, this is a conversation you don't want to miss. Chapters: 00:00 - Intro 01:18 - Common AI and Data Readiness Problems 04:27 - Real Story: Insurance Call Center AI Failure 07:58 - Sandbox to Production: The Critical Leap 11:10 - Data Governance in the Age of Citizen Developers 14:56 - Balancing Innovation with Compliance Get Mike's book "Superpowered" on Amazon: https://www.amazon.com/dp/B0F1Y2M3X4 Caxy Interactive -- Showing organizations how to play offense with technology. https://www.caxy.com | hello@caxy.com

    Why AI Fails in the Real World

  5. Oct 8

    Fashion in Gaming: $105B Market by 2030

    Your next wardrobe might not hang in a closet. It might live in a game. Digital fashion is becoming a massive business, with the market projected to reach $105.5 billion by 2030. And major brands are already paying attention. On this episode of The Digital Transformist, Mike LaVista sits down with Tracy Greenan, CEO and founder of Fashion Entertainment TV, co-author of Skins in the Game, and co-founder of the Fashion and Gaming Awards. After 30 years in traditional fashion, Tracy made a surprising pivot into gaming, digital wearables, and virtual identity. She shares what she’s learned about the rapidly evolving intersection of fashion, gaming, and digital commerce, including: • Why brands like Balenciaga and Dior are racing into gaming • How Travis Scott generated $20 million from a 10-minute Fortnite concert through virtual merchandise • Why people are spending real money on digital clothing and accessories • What entrepreneurs and brands need to understand about the virtual economy • How gaming is changing the way we think about fashion, identity, and consumer behavior The line between fashion, entertainment, and technology is getting harder to see. Tracy offers an inside look at where digital fashion is headed—and the business opportunities emerging along the way. Subscribe for more conversations about innovation, technology, and digital transformation. Chapters: 00:00 - Intro 01:05 - Traditional Fashion to Digital Pivot 03:08 - Gaming Market Size and Demographics 04:02 - Avatar Changes and Shopping Behavior 07:30 - Travis Scott Fortnite Concert Case Study 09:22 - Brand Protection in Digital Fashion 10:28 - Digital vs Physical Merchandise Economics 12:36 - Data Collection and Product Iteration 14:30 - Fashion and Gaming Awards Launch 17:37 - Tommy Hilfiger Gaming Collaboration Get Mike's book "Superpowered" on Amazon: https://www.amazon.com/dp/B0F1Y2M3X4 Caxy Interactive -- Showing organizations how to play offense with technology. https://www.caxy.com | hello@caxy.com

    Fashion in Gaming: $105B Market by 2030

  6. Sep 23

    Become a “Connected Connector”: Give More Than You Ask

    What if the person negotiating on your behalf isn’t actually on your side? Bill Himmelstein, CEO and founder of Tenant Advisory Group, pulls back the curtain on commercial real estate and explains why going without tenant representation can cost you far more than you realize. In this episode, Bill reveals: • Why some of the biggest landlords would rather you skip the broker • Why your attorney may not be able to protect you from overpaying • Why only about 20% of available properties ever make it to online searches • The costly mistakes tenants make when negotiating leases • And the networking philosophy that helped Bill build his business without relying on cold calls His secret? Becoming a “connected connector” — someone who creates opportunities for others instead of constantly asking for them. Bill has spent 17 years representing commercial real estate tenants across Chicago and nationwide. His approach to relationships, business development, and networking offers lessons that go well beyond real estate. If you sell a service, negotiate major deals, or want to build a network that actually creates opportunities, this conversation is worth a listen. Chapters: 00:00 - Intro 01:52 - What Tenant Advisory Group Does 03:54 - Red Flags When Negotiating Leases 05:57 - The Friend Landlord Myth 08:23 - Hidden Market vs Public Listings 12:01 - The Connected Connector Philosophy 13:40 - Givers Gain and BNI Origins 16:54 - Three Rules for Networking Partners 22:11 - Building Trust Through Generosity 27:30 - Managing Your Network Strategically 32:45 - The ROI of Being a Connector Get Mike's book "Superpowered" on Amazon: https://www.amazon.com/dp/B0F1Y2M3X4 Caxy Interactive -- Showing organizations how to play offense with technology. https://www.caxy.com | hello@caxy.com

    Become a “Connected Connector”: Give More Than You Ask

  7. Sep 16

    The Hidden Tax on Cross-Border Payments

    Moving money across borders sounds simple. In practice, it can be anything but. Banks, exchange rates, intermediaries, compliance requirements, and outdated payment rails can all make international payments slower, more expensive, and more complicated than they need to be. In this episode of The Digital Transformist, host Michael LaVista sits down with Ari Good, an attorney with more than 30 years of experience in fintech, blockchain, and international payments, to explore how businesses can rethink the way they move money around the world. Ari breaks down how stablecoins and compliant payment systems are creating faster, more efficient ways to make cross-border payments, whether you're paying suppliers in Mexico, manufacturing partners in Germany, or flower vendors in Colombia. They also dig into KYC compliance, common cryptocurrency mistakes, and how to choose the right payment rails for your business. If your business operates across currencies and borders, this conversation offers a practical look at where international payments are headed—and what businesses should be thinking about now. Subscribe for more episodes on digital transformation and emerging technology that drives real business results. Chapters: 00:00 - Intro 01:11 - Moving to Colombia and Working Remotely 03:13 - How International Payments Actually Work 06:11 - The Hidden Costs in Cross-Border Transactions 08:37 - Know Your Customer and Compliance Requirements 09:29 - Choosing the Right Stablecoin (USDC vs Others) 10:57 - Horror Story: Don't Hold Bitcoin Unhedged 12:03 - Stablecoins in Volatile Currency Markets 13:28 - Argentina and Venezuela Use Cases 15:41 - AI's Role in Payment Compliance 19:44 - Starting Your First International Payment Project 24:13 - Finding the Right Fintech Partner Get Mike's book "Superpowered" on Amazon: https://www.amazon.com/dp/B0F1Y2M3X4 Caxy Interactive -- Showing organizations how to play offense with technology. https://www.caxy.com | hello@caxy.com

    The Hidden Tax on Cross-Border Payments

  8. Sep 10

    The Guest Is the Game

    What if deploying AI is the easy part—and reinventing your business around it is the real challenge? Tommy Rhoads, Chief Reinvention Officer at Brave Business AI, flips the AI conversation on its head. The biggest obstacle isn’t the technology. It’s the way organizations think about work, change, and transformation. In this episode, Tommy breaks down: Why tribal and commercial casinos face very different challenges when adopting AI Why the future of work isn’t about cutting headcount, but creating a super workforce Why treating AI like another ERP implementation can set organizations up for failure The difference between change management and true organizational reinvention Why tribal gaming organizations approach new technology with a unique level of caution How to rethink work when AI is changing what thousands of people do every day Tommy Rhoads is CEO of Rhoads to Impact, Chief Reinvention Officer at Brave Business AI, and a Lean Six Sigma Master Black Belt with decades of experience transforming organizations across tribal gaming, hospitality, and Fortune 500 companies. If you’re leading digital transformation in gaming, hospitality, or any organization trying to figure out what AI means for the future of work, this conversation is for you. Chapters: 00:00 - Intro 00:52 - Tommy's Multi-Enterprise Portfolio 02:24 - AI Fatigue vs Real Implementation 04:57 - Deploying AI is Easy, Reinvention Isn't 07:35 - The Super Workforce Helmet Concept 09:02 - ERP Implementations vs AI Transformation 11:35 - The Valley of Despair in Change 14:08 - Storytelling and Organizational Change 16:40 - ROI Challenges in AI Projects 20:29 - Tribal vs Commercial Casino Perspectives 24:28 - Data Governance and AI Readiness 29:47 - Guest Experience as the Foundation Get Mike's book "Superpowered" on Amazon: https://www.amazon.com/dp/B0F1Y2M3X4 Caxy Interactive -- Showing organizations how to play offense with technology. https://www.caxy.com | hello@caxy.com

    The Guest Is the Game
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Ratings & Reviews

5
out of 5
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About

Welcome to The Digital Transformist, where we empower CEOs to lead their companies through digital transformation with confidence and clarity. If you’re a CEO of a midsize company between $100 million and $250 million in revenue or have those companies in your portfolio, and your goal is to create enterprise scale and exit, this podcast is your essential guide to leveraging technology for growth.Join us each week as we dive deep into the world of digital transformation, focusing on non-tech-enabled industries like manufacturing, construction, and distribution. We also extend our expertise to private equity and M&A firms, providing actionable strategies to drive digital excellence across investments, optimizing for both growth and exit.Whether you’re already on the path to digital success or facing obstacles in your journey, our interviews with CEOs provide valuable insights, practical advice, and inspiring stories.Discover how successful leaders are removing friction from their businesses, implementing innovative solutions, and driving tangible results. From overcoming challenges to seizing opportunities, The Digital Transformist offers actionable strategies for every stage of your digital transformation journey.

Information

  • Creator
    Michael LaVista
  • Years Active
    2024 - 2026
  • Episodes
    51
  • Rating
    Clean
  • Copyright
    © 2026 The Digital Transformist
  • Show Website
    The Digital Transformist