All Episodes

Episode 262

September 17, 2025

with Ryan Dolley

 – Vice President of Product Strategy, GoodData

This week on The Data Stack Show, Ryan Dolley joins Eric and John to discuss his unique journey from playwriting to leading product strategy in the data industry. The conversation explores the evolution of business intelligence (BI), the growing influence of AI on analytics, and the shifting skill sets required for data professionals. Key topics include the challenges of adapting to rapid technological change, the importance of embracing engineering practices in BI, and the need for continuous learning. Listeners will gain insights into how AI is transforming data roles, why storytelling remains central to analytics, practical advice for thriving in a fast-changing industry, and so much more. 

Episode 261

September 10, 2025

with Eric Dodds and John Wessel

 – Podcast Hosts, The DataStack Show

This week on The Data Stack Show, Eric Dodds and John Wessel explore how AI is reshaping the data industry, focusing on the ongoing cycles of bundling and unbundling within data infrastructure. They discuss the potential for closed ecosystems like Notion to deliver personalized, integrated experiences and examine recent industry moves such as Fivetran’s acquisitions. The conversation also highlights the challenges faced by both startups and incumbents, the influence of enterprise customers on product development, and the enduring importance of trade-offs when choosing between bundled and unbundled solutions. Key takeaways include the complexity of implementing AI across platforms, the likelihood that market cycles will persist despite technological advances, and the need for organizations to carefully weigh integration, flexibility, and long-term risk when adopting new data tools.

Episode 260

September 3, 2025

with Eric Dodds, John Wessel, and Matthew Kelliher-Gibson

 – Co-Hosts, The DataStack Show

This week on The Data Stack Show, the crew welcomes Eric Dodds back to the show as they dive into the realities of integrating AI and large language models into data team workflows. Eric, Matt, and John discuss the promise and pitfalls of AI-driven automation, the persistent challenges of working with APIs, and the evolution from big data tools to AI-powered solutions. The conversation also highlights the risks of over-reliance on single experts, the critical importance of documentation and context, and the gap between AI marketing hype and practical implementation. Key takeaways for listeners include the necessity of strong data fundamentals, the hidden costs and risks of AI adoption, the importance of balancing efficiency gains with long-term team resilience, and so much more.

Episode 259

August 27, 2025

with Kostas Pardalis

 – Co-Founder, typedef

This week on The Data Stack Show, Eric and John welcome back Kostas Pardalis, long-time co-host of the Data Stack Show and now Co-Founder of typedef. The group discusses the rapid evolution of AI and data infrastructure. The conversation also explores how AI is accelerating industry change, the challenges of integrating large language models (LLMs) into data workflows, and the limitations of current semantic layers. Kostas shares insights on building next-generation query engines, the importance of using familiar engineering paradigms, and the need to make AI seamless and almost invisible in user experiences. Key takeaways include the necessity of practical, incremental innovation, the reality behind AI hype, strategies for making advanced data tools accessible and reliable for engineers and businesses alike, and so much more.