Conversations at the intersection of data engineering and business

with Eric Dodds and John Wessel

August 26, 2026

with Ruben Burdin

 – Founder and CEO, Stacksync

This episode is a re-air of one of our most popular conversations, featuring insights worth revisiting. This week on The Data Stack Show, Eric and welcomes back Ruben Burdin, Founder and CEO of Stacksync as they together dismantle the myths surrounding zero-copy ETL and traditional data integration methods. Ruben reveals the complex challenges of two-way syncing between enterprise systems like Salesforce, HubSpot, and NetSuite, highlighting how existing tools often create more problems than solutions. He also introduces Stacksync’s innovative approach, which uses real-time SQL-based synchronization to simplify data integration, reduce maintenance overhead, and enable more efficient operational workflows. The conversation exposes the limitations of current data transfer techniques and offers a glimpse into a more declarative, flexible approach to managing enterprise data across multiple systems. You won’t want to miss it.

July 29, 2026

with Eric Dodds and John Wessel

 – Podcast Hosts, The DataStack Show

This episode is a re-air of one of our most popular conversations, featuring insights worth revisiting. 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.

June 17, 2026

with Alberto Rizzoli

 – Co-Founder and CEO, V7

This episode is a re-air of one of our most popular conversations, featuring insights worth revisiting. This week on The Data Stack Show, AI entrepreneur Alberto Rizzoli shares his journey from early computer vision breakthroughs to leading the automation of back-office workflows at V7. The discussion explores the shift from bespoke model training to configurable AI solutions, the impact of automation on business roles, and emerging best practices for integrating AI into enterprises. Listeners will gain insight into how AI infrastructure is moving from labs to everyday businesses, which roles are most vulnerable or secure amid automation, and why future-proofing your career means focusing on creativity, first principles, and continuous improvement. Don’t miss it!

May 20, 2026

with Andy MacMillan

 – Chief Executive Officer, Alteryx

This episode is a re-air of one of our most popular conversations, featuring insights worth revisiting. This week on The Data Stack Show, Brooks and John chat with Andy MacMillan, CEO of Alteryx. Andy discusses the evolving landscape of data and AI, focusing on empowering business users to solve complex problems. He explores the concept of “citizen developers” and how tools like Alteryx can bridge the gap between IT and business teams by democratizing data access. The conversation also emphasizes the importance of creating controlled environments where business users can leverage cloud data platforms and AI technologies to reimagine workflows, without bypassing governance. Key takeaways include the need for organizations to enable innovation through accessible data tools, the potential of AI-driven agents to transform business processes, the critical role of employees who understand their business functions in driving technological transformation, and so much more.

April 22, 2026

with Michael Driscoll

 – Co-Founder and CEO, Rill Data

This episode is a re-air of one of our most popular conversations, featuring insights worth revisiting. This week on The Data Stack Show, Eric and John welcome Michael Driscoll, Co-Founder and CEO of Rill Data. Mike discusses the transformative impact of AI on business intelligence (BI) and data analytics. He also explores the shift from traditional dashboard-based tools to more dynamic, code-driven, and AI-powered interfaces that provide deeper insights. During the conversation, the group emphasizes the importance of a metrics-first approach, the potential of leapfrog architectures using technologies like data lakes and real-time analytical databases, and how AI agents are increasingly becoming the primary users of data tools. The conversation highlights the evolving landscape of data infrastructure, where open standards, flexibility, and intelligent interfaces are reshaping how businesses interact with and understand their data, and more. 

March 11, 2026

with Matt Kelliher-Gibson

 – The Cynical Data Guy

This episode is a re-air of one of our most popular conversations, featuring insights worth revisiting. This week on The Data Stack Show, John and Matt bring you another edition of the Cynical Data Guy. John and Matt dive into the evolution of customer data infrastructure, the growing influence of low-code tools like Clay, and the blurred lines around the “engineer” title in modern data roles. They also discuss the trade-offs between SaaS adoption and building custom solutions, the pitfalls of enterprise software buying, and the realities of platform lock-in—using Palantir’s unique business model as a case study. Key takeaways include the importance of simplicity and scalability in data engineering, the need for clear requirements when evaluating tools, and a healthy skepticism toward sales pitches and “art of the possible” features. Don’t miss this month’s Cynical Data Guy.