DataDay with Greg Michaelson is a podcast about the real lives of people who work with data and AI every day. Not the polished conference-talk version, but the messy, clever, practical, human side of analytics work. Each episode sits down with someone who’s in the trenches building models, shipping dashboards, wrangling pipelines, or experimenting with agentic AI to get actual work done.
Host Greg Michaelson digs into how these practitioners think, how they solve problems, and the quirks that make each of them unique. Learn about the shortcuts they swear by, the habits they can’t break, the tools they love, the ones they avoid, and the weird constraints that shape their day-to-day.
You’ll hear stories about debugging agents at 2AM, designing workflows that survive contact with real users, navigating organizational chaos, and figuring out how to stay curious while the field changes under your feet. It’s a practical, grounded conversation about doing data and AI work in the real world, one day at a time.
William Morgan and The Future of AI Infrastructure: Kubernetes, Open Models & What Comes Next
William Morgan, founder and CEO of Buoyant and creator of Linkerd, joins Greg Michaelson to talk about how modern software infrastructure is changing in the age of AI.
William breaks down Kubernetes and service meshes in plain English, shares lessons from helping scale Twitter during its early years, and explains why Buoyant built Linkerd as an open-source project.
They also dig into how AI is changing software development, where AI-generated code can—and absolutely cannot—be trusted, and why the next major shift may be companies running powerful open-weight AI models inside their own infrastructure rather than relying entirely on external model providers.
Topics include Kubernetes, Linkerd, service meshes, platform engineering, open-source business models, AI-assisted coding, local AI inference, open-weight models, GPUs, and the future of enterprise AI infrastructure.
28 Jul 2026
Chris Nyhuis - Inside the Mind of a Cyber Defender
Most cyberattacks never make the news—but they happen every day. In this episode, Greg Michaelson sits down with Chris Nyhuis, CEO of Vigilant, to explore how modern attackers infiltrate organizations, why most companies don't detect breaches for months, and how Vigilant has reduced that window to just four hours. They discuss supply chain attacks, AI-powered cybersecurity, critical infrastructure, ransomware myths, protecting your home network, and Chris's remarkable work fighting human trafficking through technology.
21 Jul 2026
Derek Crager: Why AI Should Think With People, Not Replace Them
In this episode, Greg sits down with Derek Crager, founder of Practical AI and creator of the Human-First AI philosophy. Derek shares his journey from industrial construction to Amazon, where he built the company's highest-rated employee training program and helped reduce technician attrition from over 80% to around 30%. The conversation explores why most enterprise AI initiatives fail, how voice-based AI mentors can preserve critical workforce knowledge, why specialized AI models outperform general-purpose chatbots for many tasks, and what it really means for AI to augment—not replace—human expertise.
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