The Data Stack Show

In this bonus episode, Eric and John preview their upcoming conversation with Alberto Rizzoli of V7.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.

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. Highlights from this week’s conversation include:Ryan’s Journey: From Playwriting to Data (1:05)Making a Living as a Playwright (3:02)Transitioning to BI: Night School and First Data Jobs (4:12)Storytelling and Data: The Art of BI (6:22)Early BI Work: Data Warehouses and PDF Reports (8:33)Moving from Utilities to Consulting (13:03)Building vs. Implementing: Product Strategy Lessons (16:37)The AI Shift in BI and Analytics (18:41)Automation Anxiety: The Human Side of Data Change (22:16)The Evolving Role of BI Experts (25:18)Adapting to Change: Learning Code and Experimentation (29:34)AI and the Future of Embedded Analytics (33:38)Capturing Intent: The Value of Modern BI Interfaces (37:03)Bridging the Data and Software Engineering Gap (39:13)The Historical Divide: Data vs. Software Engineering (43:06)Organizational Challenges: Where Does BI Belong? (46:05)Reflections on Self-Service BI and Value (48:46)If Not Data: Ryan’s Alternate Career Paths (49:04)Final Thoughts and Takeaways (50:17)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.

In this bonus episode, Eric and John preview their upcoming conversation with Ryan Dolley of GoodData.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.

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 (15:53Longevity 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.

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.Highlights from this week’s conversation include:Eric is Back from Europe (0:37)AI and Data: Jurisdiction and Comfort Level (4:00)APIs, Tool Calls, and Practical AI Limitations (5:08)Scaling, Big Data, and AI’s Current Constraints (9:16)Stakeholder-Facing AI and Data Team Risks (13:20)Self-Service Analytics and AI’s Real Impact (16:04)AI Hype vs. Reality and Uneven Impact (20:27)Cost, Context, and AI’s Practical Barriers (25:25)AI for Admin Tasks and Business Logic Complexity (29:13)Tribal Knowledge, Documentation, and Context Engineering (32:07)AI as a Productivity Accelerator and the “Gary Problem” (35:10)Healthy Conflict, Team Dynamics, and AI’s Limits (39:15)Back to Fundamentals: Good Practices Enable AI (41:47)Lightning Round: Favorite AI Tools and Workflow Integration (45:56)AI in Everyday Life and Closing Thoughts (48:14)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.

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. Highlights from this week’s conversation include:Kostas’s Background and Career Timeline (1:10)Transition from RudderStack to Starburst Data (4:25)AI Acceleration and Industry Impact (9:37)AI Hype, Investment, and Polarized Reactions (12:05)Historical Parallels and Tech Adoption (13:54)AI Disrupting Tech Workers and Internal Drama (18:56)Experimentation Phase and Future AI Applications (24:01)Invisible AI and User Experience (28:21)AI in Data Infrastructure and LLMs (34:24)SQL, LLMs, and Engineering Solutions (36:35)Standardization, Semantic Layers, and Data Modeling (41:01)Introduction to typedef (45:49)Productionizing AI Workloads with typedef (51:36)Familiarity, Reliability, and Engineering Best Practices (57:24)Security, Enterprise Concerns, and Open Source Models (1:00:48)Final Thoughts and Takeaways (1:01:47)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.

In this bonus episode, Eric and John welcome back longtime co-host of the Data Stack Show Kostas Pardalis to talk through all things AI and his co-founding of typedef.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.

This week on The Data Stack Show, John and Matt dive into the latest trends in AI, discussing the evolution of GPT models, the role of tools in reducing hallucinations, and the ongoing debate between data warehouses and agent-based approaches. They also explore the complexities of risk-taking in data teams, drawing lessons from Nate Silver’s book on risk and sharing real-world analogies from cybersecurity, football, and political campaigns. Key takeaways include the importance of balancing innovation with practical risk management, the need for clear recommendations from data professionals, the value of reading fiction to understand human behavior in data, and so much more. Highlights from this week’s conversation include:Initial Impressions of GPT-5 (1:41)AI Hallucinations and the Open-Source GPT Model (4:06)Tools and Determinism in AI Agents (6:00)Risks of Tool Reliance in AI (8:05)The Next Big Data Fight: Warehouses vs. Agents (10:21)Real-Time Data Processing Limitations (12:56)Risk in Data and AI: Book Recommendation (17:08)Measurable vs. Perceived Risk in Business (20:10)Security Trade-Offs and Organizational Impact (22:31)The Quest for Certainty and Wicked Learning Environments (27:37)Poker, Process, and Data Team Longevity (29:11)Support Roles and Limits of Data Teams (32:56)Final Thoughts and Takeaways (34:20) 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.

In this bonus episode, John and Matt preview their upcoming conversation about trends in AI, the evolution of GPT modes and the ongoing debate between data warehouses and agent-based approaches.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.

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.

In this bonus episode, John and Matt preview the next installment of the Cynical Data Guy. 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.

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.

In this bonus episode, Brooks and John preview their upcoming conversation with Andy MacMillan of Alteryx.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.

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 quirky world of data analytics, exploring common challenges like unrealistic data requests, the limitations of self-service BI, and the evolving role of data analysts. They also discuss the importance of understanding business context, the need for effective data storytelling, and the emerging trend of "BI as code" which promises more flexible and version-controlled analytics tools. The conversation highlights the gap between technical data capabilities and business user needs, emphasizing that the real value of data professionals lies not just in tool proficiency, but in their ability to provide meaningful insights and guide decision-making. Key takeaways include the importance of context in data analysis, the limitations of self-service tools, the ongoing evolution of data roles in modern organizations, and more. Highlights from this week’s conversation include:Reading and Reacting to the LinkedIn Data Request Post (1:36)Changing KPIs and Data Skepticism (2:21)The Burden of Proving Data Integrity (5:00)Handling Metric Changes and Historical Comparisons (7:16)Preparing Stakeholders for New Metrics (9:16)BI Code, Version Control, and Modern Dashboards (11:20)Scoping and Business Context in Data Roles (14:38)Technical vs. Business Understanding in Data Teams (16:29)GUI vs. Code in Dashboard Customization (20:41)The Analyst’s Role: Guidance Over Tools (23:23)Hiring and the Real-World Analyst Skillset (28:11)Final Thoughts and Takeaways (30:36)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.

In this bonus episode, John and Matt preview the next edition of the Cynical Data Guy. 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.