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. 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

  2. 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

  3. 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

  4. Sep 2

    80% of Employee Productivity Is Left on the Table with Kathy Eastwood

    What if 80% of your team's potential productivity is sitting idle right now? Kathy Eastwood, CEO and founder of E Equals Y, reveals that employee engagement hovers around just 20%—meaning leaders are leaving massive performance gains untouched simply because they haven't learned to speak their people's language. In this episode, Kathy shares her journey from CPA at Ernst & Young to Chief People Officer, uncovering the repeatable patterns that separate successful transformations from expensive failures. She introduces her "FEUD" framework (Fear, Ego, Uncertainty, Doubt) to help leaders identify what's actually blocking change in their organizations, and explains why understanding whether your team makes decisions from the head or the heart is the key to unlocking performance. Kathy brings a rare combination of financial rigor and people-first leadership, having led digital transformations across tech companies and nonprofits alike. Her insights on generational differences, growth mindset, and why command-and-control leadership is costing you talent are essential for any leader navigating today's complex workplace. Subscribe for more conversations on leading transformation that actually sticks, and share this episode with a leader who needs to hear it. Chapters: 00:00 - Intro 00:28 - Kathy's Career Journey from CPA to People Officer 03:51 - Why Growth Mindset Matters in Leadership 06:18 - The FEUD Framework: Fear, Ego, Uncertainty, Doubt 09:33 - Eradicating Poor Management Styles 13:07 - Generational Shifts in Employee Expectations 16:48 - Understanding Individual Motivation and Energy 21:21 - The Cost of Disengagement and Low Morale 28:03 - Building Trust Through Consistency and Transparency 34:15 - Remote Work, Autonomy, and Modern Leadership 42:30 - Final Thoughts and Where to Find Kathy 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

    80% of Employee Productivity Is Left on the Table with Kathy Eastwood

  5. Aug 26

    Philosophic lessons from leadership with William Crossan

    What if your business success isn't about working harder, but about bringing your whole self—head, heart, and gut—to work? Former Air Force member turned Fortune 100 leader William Crossan shares how he discovered that disconnecting from emotion in leadership was sabotaging everything. In this episode, William reveals why "culture" is more than a buzzword and how spiritual principles drive tangible business results. You'll learn about the three neural networks that inform decision-making, why we're shifting from knowledge workers to empathy workers in the AI age, and how wilderness experiences can unlock authentic leadership. William walks us through his journey from building the #1 organization at a Fortune 100 company to founding Campfire Culture, where he helps leaders reconnect with purpose. William Crossan is the founder of Campfire Culture and Chief Visionary Officer at Financial Growth Partners, where he led a turnaround that took a nonprofitable firm to profitability in under three years. If you're rethinking what leadership means in today's world, subscribe and share this episode with someone who needs to hear it. Chapters: 00:00 - Intro 01:05 - Military Background to Leadership Philosophy 02:33 - Culture Drives Structure Drives Results 04:52 - Why Everything in Business Is Spiritual 07:46 - Three Neural Networks in Decision Making 12:19 - Wilderness as Leadership Development Tool 17:42 - Rites of Passage and Modern Masculinity 24:31 - Philosophy Meets Business Strategy 29:15 - Creating Meaningful Work Environments 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

    Philosophic lessons from leadership with William Crossan

  6. Aug 20

    3 Reasons Startups Fail with Kristi Ross

    What if the secret to building a mass market company was hiding in something as simple as a coffee bean? In this episode, Kristi Ross reveals how understanding her employees financial literacy turned into a competitive advantage. Michael sits down with Kristi Ross, co-founder of TastyTrade and founder of U3 Coffee, to explore the surprising challenges of building a coffee ecosystem company. With 35 years in trading and over 40 mergers and acquisitions under her belt, Kristi shares why she left the financial world to unite farmers, entrepreneurs, and customers through specialty coffee. You'll discover the three critical reasons startups fail, why basic technology still solves massive problems in ancient industries, and how Quantum in Chicago is the next big thing. Kristi brings hard-won wisdom from building 7 companies in 10 years and transitioning from serving 7% of Americans (options traders) to 75% (coffee drinkers). Her insights on employee engagement, financial education, and community impact will change how you think about mass market businesses. Subscribe for more conversations with founders who are transforming traditional industries through innovation and heart. Chapters: 00:00 - Intro 00:55 - Why Coffee After TastyTrade Exit 03:56 - Disrupting the Coffee Supply Chain 06:31 - Financial Literacy for Employees 11:16 - The U3 Coffee Bank Mission 14:41 - Blockchain and Tipping the Farmer 19:49 - Three Reasons Startups Fail 29:10 - Building a Family Business 35:22 - Mass Market vs Niche Strategy 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

    3 Reasons Startups Fail with Kristi Ross

  7. Aug 12

    Desmond Clark's Journey: From NFL to Logistics

    What if the secret to thriving in logistics isn't newer technology, but older wisdom about human connection? Former NFL tight end Desmond Clark reveals why his brokerage firm flies to remote Texas oil fields and shows up at customer job sites—a rare move in an industry that's increasingly automated. In this conversation, Des walks through his winding path from 12 years in professional football to founding Bear Down Logistics in 2021. You'll learn why he believes AI should enhance human relationships rather than replace them, how showing up in person during a crisis can turn potential disaster into deeper trust, and what "standards over feelings" really means when you're building a company culture. Des brings hard-won lessons from the NFL locker room to the logistics boardroom, sharing frameworks from his book *Principles of Winning* that apply whether you're moving freight or moving the needle on company performance. If you're rethinking how technology and humanity intersect in your business, this episode is for you. Subscribe for more conversations with leaders who are transforming industries through people-first innovation. Chapters: 00:00 - Intro 00:34 - NFL Career to Entrepreneurship Journey 02:01 - Human Connection Over Technology 04:45 - Meeting Customers in Person 06:31 - Discovering Hidden Opportunities on Site 09:00 - Crisis Management and Problem Solving 10:35 - Standards Over Feelings Philosophy 14:44 - Giving Honest Feedback on Teams 18:23 - Accountability and Culture Building 24:16 - Personal Growth and Self-Awareness 28:40 - Building Bear Down Logistics 32:15 - Operational Excellence in Practice 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

    Desmond Clark's Journey: From NFL to Logistics

  8. Aug 6

    Health Data and it's Importance to Chicago

    What if a difference of just a few miles could mean 20 years of life? In Chicago, where you live dramatically impacts how long you live—and Juan Rojas is using health system data to close that gap. In this episode, Juan Rojas shares how the Rush Health Equity Analytics Studio is transforming community health by breaking down data silos and making critical health information accessible. You'll learn why hospital records reveal more than surveys, how census-tract-level data can pinpoint hypertension hotspots, and what happens when communities can see their own health landscape for the first time. Juan explains the critical role of applying an "equity lens" to clinical problems and why bridging the gap between technical and clinical teams is essential for meaningful change. Juan Rojas is the Associate Chief Medical Officer at Rush University Medical Center and Director of the Rush Health Equity Analytics Studio, where he translates complex healthcare data into actionable insights for Chicago communities. Subscribe to The Digital Transformist for more conversations on using data and AI to solve real-world problems. Chapters: 00:00 - Intro 01:01 - Creating the Rush Health Equity Analytics Studio 02:12 - Chicago's 20-Year Life Expectancy Gap 03:52 - Health System Data vs Survey Data 06:21 - Bridging Clinical and Technical Worlds 08:16 - Data Bias and Equity Challenges 10:45 - Mapping Hypertension Across Census Tracts 12:41 - Exploring ChicagoHealthMap.com 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

    Health Data and it's Importance to Chicago
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Ratings & Reviews

5
out of 5
2 Ratings

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
    46
  • Rating
    Clean
  • Copyright
    © 2026 The Digital Transformist
  • Show Website
    The Digital Transformist