In this episode of Deep Dive, we explore what it takes to lead higher education IT teams through profound uncertainty. Drawing on lessons from four major disruptions—the dot-com crash, the Great Recession, the COVID-19 pandemic, and today’s unfolding federal policy-driven changes—this episode offers a leadership playbook built on clarity, emotional endurance, and calm. Whether you’re a CIO, a mid-career leader, or someone navigating change on your campus, this conversation unpacks the quiet skills that matter most when the road ahead disappears.

Based on Substack article:

https://dispatchesinternetpioneer.substack.com/p/resilience-in-the-fog-of-uncertainty

Energetic Business Background Music by LolaMoore -- https://freesound.org/s/754966/ -- License: Attribution 4.0

In this week’s dispatch, we unravel the complex legal challenges surrounding generative AI—challenges that could shape not just the future of technology, but America’s role in leading it. From The New York Times v. OpenAI to Getty Images v. Stability AI, the courtroom battles are heating up, raising urgent questions about what counts as fair use in a GenAI-driven world. We explore what’s at stake for U.S. innovation, contrasting America’s legal gridlock with China’s more permissive approach to copyright and data use. As China accelerates GenAI development with fewer restrictions, we examine whether the U.S. can strike the right balance—protecting creators without stifling the very innovation that built Silicon Valley.

Based on Substack article:

https://dispatchesinternetpioneer.substack.com/p/the-fair-use-dilemma-innovation-china

Energetic Business Background Music by LolaMoore -- https://freesound.org/s/754966/ -- License: Attribution 4.0

This episode explores why the long-standing strategy of scaling through vendor standardization is now putting higher ed IT at risk. As costs rise and vendor flexibility shrinks, institutions need a new playbook—one built on diversification and leverage. Drawing from real-world examples, including a survey tool negotiation turned case study, we break down how CIOs can regain control by adopting a “Lexus and Toyota” model across their IT portfolios.

Based on Substack article:

https://dispatchesinternetpioneer.substack.com/p/breaking-scale

Energetic Business Background Music by LolaMoore -- https://freesound.org/s/754966/ -- License: Attribution 4.0

In this episode, we explore how the Internet, smartphones, and artificial intelligence have fundamentally reshaped the way we connect—not just to information but to one another. Drawing from decades of experience, we walk through the three major tech shifts of our time—1993, 2007, and 2022—and examine how each one chipped away at the traditional institutions that once structured our social and civic lives. What began as a promise of empowerment has left us tethered to algorithm-driven platforms, disconnected from shared norms, and increasingly polarized. From the collapse of gatekeeping to the rise of brittle, many-to-many networks, this episode reflects on what we’ve lost, what we’ve learned, and what it might take to rebuild trust in the digital age.

Based on Substack article:

https://dispatchesinternetpioneer.substack.com/p/from-institutions-to-algorithms

Energetic Business Background Music by LolaMoore -- https://freesound.org/s/754966/ -- License: Attribution 4.0

In today’s episode, we’re talking about mentorship—but not the kind you find in structured programs or formal pairings. This is about the kind of mentorship that happens in the trenches—when you’re working for someone who believes in you, challenges you, and shapes you through how they lead every day. If you’re early in your career, this episode will give you a sense of what to look for in a great boss. If you’re further along, it’s a reminder of the kind of leader we should all strive to be.

Based on Substack article:

https://dispatchesinternetpioneer.substack.com/p/mentorship-is-overratedunless-you

Energetic Business Background Music by LolaMoore -- https://freesound.org/s/754966/ -- License: Attribution 4.0

Generative AI tools like ChatGPT, Microsoft Copilot, and Google Gemini retain more user data than most people realize, raising serious ethical, legal, and privacy concerns. In this episode, we explore the hidden memory of GenAI, including sensitive data retention in a government agency and the growing challenges of AI-driven profiling and data transparency. We discuss how AI systems silently build user “digital twins,” why privacy compliance is struggling to keep up, and what needs to change. If you think AI forgets, think again—tune in for a deep dive into AI memory, regulation gaps, and the urgent need for user control.

Based on Substack article:

https://dispatchesinternetpioneer.substack.com/p/forget-agiworry-about-what-genai

Energetic Business Background Music by LolaMoore -- https://freesound.org/s/754966/ -- License: Attribution 4.0

Extreme anchoring isn’t just a negotiation tactic—it’s a strategy for shifting the entire debate in your favor. In this episode, we explore how leaders use extreme anchoring to move the Overton Window, forcing counterparties to react while keeping the final outcome closer to their desired outcome. Drawing from negotiation theory, we break down real-world examples from business, reality TV, and politics and discuss how other leaders have successfully redefined mainstream discourse. Plus, we dive into an FBI negotiator's playbook to explore how to counter extreme anchors effectively in leadership, business, and everyday conversations. Listen in to learn how to recognize and respond when someone shifts the playing field on you.

Based on Substack article:

https://dispatchesinternetpioneer.substack.com/p/extreme-anchors-and-the-overton-window

Energetic Business Background Music by LolaMoore -- https://freesound.org/s/754966/ -- License: Attribution 4.0

This episode examines why low-code everyday AI is the smarter, more sustainable choice for higher education—and why the old “build-it” mentality no longer works. IT organizations are under pressure to adopt everyday AI, but custom-built solutions are expensive, insecure, and impossible to maintain at scale. We break down the real costs of DIY everyday AI, the security risks of homegrown models, and why universities have already moved away from custom development in other areas. Tune in to explore a practical everyday AI adoption strategy that balances innovation, cost containment, and long-term viability.

Based on the Substack article:

https://dispatchesinternetpioneer.substack.com/p/the-case-for-low-code-everyday-ai

Energetic Business Background Music by LolaMoore -- https://freesound.org/s/754966/ -- License: Attribution 4.0

This episode examines how GenAI could drive economic transformation by radically simplifying workflows, contrasted with the Internet's success in 1993 and the iPhone's limited productivity impact in 2007. Learn practical work simplification principles inspired by Toyota and their application in sectors like healthcare and cybersecurity. We also address the cultural hurdles and structural resistance that slow GenAI adoption, featuring insights from a CIO's leadership journey.

Based on Substack article:

https://dispatchesinternetpioneer.substack.com/p/the-missing-piece-in-genais-economic

Energetic Business Background Music by LolaMoore -- https://freesound.org/s/754966/ -- License: Attribution 4.0

This episode examines the real role of AI in higher education—what’s useful, what’s overhyped, and where universities should actually invest. With AI adoption accelerating, institutions face a critical choice: embrace low-cost everyday AI for efficiency or pursue high-stakes, game-changing AI with long-term impact. We break down the differences, explore real-world use cases, and discuss smart AI strategies that balance innovation with financial sustainability. Tune in to cut through the hype and discover how AI can truly transform higher ed—without unnecessary risks.

Based on Substack article:

https://dispatchesinternetpioneer.substack.com/p/ai-in-higher-ed-what-matters-and

Energetic Business Background Music by LolaMoore -- https://freesound.org/s/754966/ -- License: Attribution 4.0