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. 16h ago

    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

  2. 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

  3. 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

  4. 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

  5. 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

  6. Jul 16

    AI Should Amplify People, Not Replace

    Have you ever wondered what happens when a corporate executive "accidentally" becomes an entrepreneur? Stephanie Sylvestre wasn't looking to leave her comfortable corporate career—until a chance conversation about digital twins sparked an idea she couldn't ignore. In this episode, Stephanie shares her journey from corporate America to founding Avatar Buddy, LLC, an AI company dedicated to amplifying people rather than replacing them. You'll learn why she believes the biggest risk in AI isn't job loss but unsupervised implementation, how she turned her CFO's expertise into an AI agent that mirrors how humans think and solve problems, and why relying on uninformed opinions about AI replacing jobs can be dangerous." Stephanie Sylvestre is the co-founder of Avatar Buddy and former executive at The Children's Trust in Miami-Dade County, where she managed a $184 million portfolio. If you're navigating the messy middle of AI implementation in your business, this conversation will change how you think about automation. Subscribe for more candid conversations about digital transformation. Chapters: 00:00 - Intro 00:49 - From Corporate America to Entrepreneurship 03:13 - The No-Choice-But-to-Succeed Moment 04:38 - Avatar Buddy's Mission: Amplify People, Not Replace Them 05:51 - Why Jobs Are Just a Series of Tasks 07:52 - Creating Fiscal Buddy: Cloning a Rockstar CFO 11:13 - The Power of Removing Mundane Work 12:18 - Digital Howard and the 50-Page Marketing Strategy 14:36 - Why relying on uninformed opinions about AI replacing jobs can be dangerous 15:45 - The Terrifying Power of AI Finding Security Holes 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 Should Amplify People, Not Replace

  7. Jun 22

    Construction Opportunities Nearly Doubled in 2025

    Construction opportunities have nearly doubled in 2025—and it's not just about buildings. Regional President Damian Eallonardo of W.E. O'Neil Construction reveals that optimism is driving unprecedented demand across the Midwest and beyond, fueling growth in everything from tech campuses to healthcare facilities. In this episode, you'll discover what's really behind the construction boom, how successful builders solve problems before clients even know they exist, and why the skilled labor shortage is about to get much worse as baby boomers retire. Damian brings over 30 years of construction expertise, leading O'Neil's operations east of the Rockies. He shares candid insights on attracting talent in an "online business" world, the death of tribal knowledge management, and why AI might finally transform an industry notoriously slow to adopt new technology. From data centers powering our digital lives to the future of apprenticeship programs, this conversation goes deep on the forces reshaping how America builds. If you're interested in where business, technology, and infrastructure intersect, this episode delivers actionable insights you won't find anywhere else. Subscribe for more conversations with leaders navigating digital transformation in unexpected industries. To reach Damian, please visit https://www.weoneil.com/ Chapters: 00:00 - Intro 00:37 - Why W.E. O'Neil Construction 02:24 - What's Driving Construction Demand 05:59 - Problem Solving Mindset in Construction 09:16 - Finding and Retaining Skilled Labor 12:16 - Tribal Knowledge and Cultural Shifts 14:46 - Technology Adoption in Construction 19:20 - AI's Role in Construction Future 25:08 - Data Centers and Digital Infrastructure 31:45 - Apprenticeship Programs and Trade Schools 37:22 - Private Equity in Construction 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.

    Construction Opportunities Nearly Doubled in 2025

  8. Jun 16

    We Don't Have the Energy Infrastructure to Power AI

    The water shuts off mid-morning in Houston, and it's a stark reminder: we don't have the infrastructure to power AI at the scale everyone's betting on. Tamika Tyson, a veteran risk advisor with 25+ years managing infrastructure and energy investments, explains why she's not panicking about AI—and why you shouldn't either. In this episode, Tamika breaks down the real bottlenecks holding back AI adoption: energy grids that can't handle the load, water shortages competing with data centers (and golf courses), and the five-year timeline before we have real solutions. She shares hard-won lessons from managing risk through every crisis cycle, from dot-com to COVID, and explains why the best opportunities are created in downturns—if you're disciplined enough to see them. Tamika is the founder of Scale, a risk-informed advisory firm, and has spent her career at the intersection of energy, infrastructure, and capital markets. Her perspective cuts through the hype with practical insights on navigating uncertainty, making smarter capital decisions, and positioning for long-term value when everyone else is reacting. Subscribe for more conversations with leaders who've seen it all and know how to think clearly when the market doesn't. Chapters: 00:00 - Intro 00:35 - Tamika's Background in Risk and Infrastructure 02:24 - Why Markets Repeat the Same Patterns 03:48 - Finding Opportunity in Crisis 05:23 - The Energy Infrastructure Problem with AI 09:42 - Why We Need All Energy Sources 11:50 - How Companies Are Actually Using AI 15:09 - AI Assistants and Task Automation 19:07 - Building Trust in AI Systems 22:15 - Setting Realistic Expectations for AI ROI 25:48 - Strategic Planning in Uncertain Times 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

    We Don't Have the Energy Infrastructure to Power AI
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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
    43
  • Rating
    Clean
  • Copyright
    © 2026 The Digital Transformist
  • Show Website
    The Digital Transformist