The Digital Transformist

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.

The Digital Transformist is a business podcast hosted by Unknown Host, with 0 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Unknown Host hosts The Digital Transformist, a business show with 0 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #38

  The Hidden Tax on Cross-Border Payments

  Sep 16, 202629 minS3

  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 Banks, exchange rates, intermediaries, compliance requirements, and outdated payment rails can all make international payments slower, more expensive, and more complicated than they need to be.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

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  The Digital Transformist

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

  Sep 2, 202626 min

  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

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  The Digital Transformist

  3 Reasons Startups Fail with Kristi Ross

  Aug 20, 202636 min

  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

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  Episode #34

  Health Data and it's Importance to Chicago

  Aug 6, 202630 minS2

  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

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  Episode #33

  AI Should Amplify People, Not Replace

  Jul 16, 202627 minS2

  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

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