The Data Stack Show

Pete Hunt, CEO of Dagster Labs and a pioneer behind React, traces his journey from Facebook and Twitter to modern data infrastructure. He explores data complexity, orchestration, observability, and the power of strong abstractions. The conversation also looks at AI-powered developer tools, self-service pipelines, component marketplaces, and the future of collaborative data engineering.

Ruben Burdin, founder and CEO of StackSync and YC alum who builds real-time two-way syncing between CRMs, ERPs, and data warehouses. He explains why two-way syncs are so hard and why zero-copy ETL is overhyped. He walks through real-time SQL syncing, handling mismatched keys and complex ERP workflows, and how declarative triggers and upserts simplify operational data flows.

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. Highlights from this week’s conversation include: AI’s Value and Early Ecosystem Integration (1:11) Closed Ecosystems and AI Opportunities (3:21) Personalized Software and the Blank Page Problem (6:17) Transition to Data Industry: Bundling Trends (9:56) Market Cycles and AI’s Role in Bundling (12:56) Incumbents, Innovation, and AI Layering (15:53 Longevity of Legacy Systems and Ecosystem Risks (17:56) Switching Costs and Incumbent Advantages (20:33) People Dynamics and the Startup-to-Incumbent Arc (22:50) Enterprise Data Infrastructure: Engineering Challenges (26:33) Fragmentation, Bundling Value, and AI’s Insulation Effect (29:54) Too Many Tools: The Real Meaning Behind Bundling Demand (31:36) Trade-offs in Bundling, Unbundling, and AI (33:40) Final Thoughts and Takeaways (34:34) The Data Stack Show is a weekly podcast powered by RudderStack, customer data infrastructure that enables you to deliver real-time customer event data everywhere it’s needed to power smarter decisions and better customer experiences. Each week, we’ll talk to data engineers, analysts, and data scientists about their experience around building and maintaining data infrastructure, delivering data and data products, and driving better outcomes across their businesses with data. RudderStack helps businesses make the most out of their customer data while ensuring data privacy and security. To learn more about RudderStack visit rudderstack.com. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Alberto Rizzoli, co-founder and CEO of V7 and longtime AI entrepreneur, shares his shift from early computer vision to building configurable AI for back-office automation. He discusses scaling AI from bespoke models to off-the-shelf workflows. Topics include enterprise-grade multi-step reasoning, capturing tacit SOPs, ROI from automation, and which roles are most exposed or protected as AI spreads.

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. Highlights from this week’s conversation include: Andy’s Background and Journey in Data (0:54) Early Web Development at General Motors (2:23) AI Challenges in the Enterprise (9:03) What is Alteryx and Its Value Proposition (11:25) The Importance of Empowering Business Users (16:10) Bridging the Gap Between Data Platforms and Business Users (20:04) Evolution from Desktop to Data Cloud (25:28) Access and Governance in the Cloud Era (27:57) The Return of Local Data Work and AI Governance (31:24) AI Data Clearinghouse and Governance (34:11) AI-Enabled Workflows and Business Impact (38:13) The Future: Agents, Data Platforms, and Business Logic (41:05) How to Get Started with Alteryx or Learn More (46:54) Product Management Lessons for Leadership and Parting Thoughts (47:56) The Data Stack Show is a weekly podcast powered by RudderStack, customer data infrastructure that enables you to deliver real-time customer event data everywhere it’s needed to power smarter decisions and better customer experiences. Each week, we’ll talk to data engineers, analysts, and data scientists about their experience around building and maintaining data infrastructure, delivering data and data products, and driving better outcomes across their businesses with data. RudderStack helps businesses make the most out of their customer data while ensuring data privacy and security. To learn more about RudderStack visit rudderstack.com. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Mike Driscoll, Co-founder and CEO of Rill Data, a leader in BI-as-code and AI-driven analytics. He discusses AI transforming BI, moving from static dashboards to code-first and AI-native interfaces. Topics include metrics-first design, leapfrog architectures with data lakes and real-time databases, MCP servers for natural language querying, and agents becoming primary data users.

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.  Highlights from this week’s conversation include: Reacting to the Rise of the GTM Engineer (1:11) Is "Engineer" the Right Term? (4:49) Low-Code Tools, AI, and Future Workflows (7:14) Simplicity in Data Engineering (14:38) The Pitfalls of "Simple" Solutions (15:18) Choosing SaaS vs. Building In-House (18:26) Business Process Abstraction and SaaS Adoption (21:31) Enterprise Software: Art of the Possible vs. Practicality (24:31) Sales Advice: Focus on Customer Needs (27:11) Forward Deployed Engineers and Delivery Models (29:05) Platform Lock-In: When Is It a Dirty Word? (36:41) Legacy Systems and the Reality of Lock-In (39:53) Final Thoughts and Takeaways (40:55) The Data Stack Show is a weekly podcast powered by RudderStack, customer data infrastructure that enables you to deliver real-time customer event data everywhere it’s needed to power smarter decisions and better customer experiences. Each week, we’ll talk to data engineers, analysts, and data scientists about their experience around building and maintaining data infrastructure, delivering data and data products, and driving better outcomes across their businesses with data. RudderStack helps businesses make the most out of their customer data while ensuring data privacy and security. To learn more about RudderStack visit rudderstack.com. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Ben Rogojan, owner of Seattle Data Guy and data consultant who advises companies on analytics strategy and community building. He talks about how data teams must prove tangible value in tight budgets. Conversation covers AI’s impact, prioritizing high-impact work over vanity metrics, delivering minimal actionable outputs, and the skills needed to bridge data and business.

Barry McCardel, CEO and co-founder of Hex, shares his vast expertise in data tools and AI integration. He tackles the anxieties surrounding AI’s impact on job roles, emphasizing the shift from coding to strategic problem-solving. Barry discusses the benefits of embedding AI in workflows, enhancing team structures, and fostering innovation. He highlights the infinite demand for data insights and the necessity for organizations to adapt by leveraging AI-driven tools. Overall, he paints a picture of a rapidly evolving data landscape brimming with opportunity.

In this insightful discussion, Matt, known as the 'Cynical Data Guy', shares his experience with the evolution of AI, particularly GPT-5, noting its modest improvements and persistent issues. He delves into the risks of relying on tools, highlighting the need for control layers to mitigate AI hallucinations. The conversation addresses the ongoing debate of data warehouses versus agent-based approaches, and how understanding risk through poker can inform data teams. Matt also recommends reading fiction to enhance comprehension of human behavior in data work.