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Recent episodes
TOKENMAXXING IS FOR FOOLS - Freestyle Friday (May 1, 2026)
May 1, 2026
Unknown duration
Why Snowflake Bought SelectStar - and What "Data Catalog" Means Now w/ Shinji Kim
Apr 30, 2026
Unknown duration
WTF is a Software Moat in 2026? - Freestyle Friday (4/24/2026)
Apr 24, 2026
Unknown duration
The Future of Open Data Infrastructure with George Fraser (CEO of Fivetran)
Apr 23, 2026
Unknown duration
We're in 1905: Why Electricity (Not Dot-Com) Is the Right AI Analogy - Freestyle Friday, 4/17/2026
Apr 17, 2026
Unknown duration
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| Date | Episode | Description | Length | ||||||
|---|---|---|---|---|---|---|---|---|---|
| 5/1/26 | TOKENMAXXING IS FOR FOOLS - Freestyle Friday (May 1, 2026) | Stop Tokenmaxxing and step off the AI hamster wheel. Welcome to another Freestyle Friday! What's the overwhelming vibe in the AI zeitgeist? "If you aren't maxing out AI every second, you're going to be left behind." Therefore, Tokenmaxxing is the way, right?I strongly disagree. We're burning ourselves out with fake productivity and a graveyard of abandoned AI-generated projects.In this episode, I talk about my new minimalist travel setup, why I'm purposefully trying to minimize my AI usage for deep cognitive work, and what skills will actually get you left behind (hint: it's not missing the latest model release).Solve real problems. Focus on the fundamentals. Take a walk. You're going to be fine. | — | ||||||
| 4/30/26 | Why Snowflake Bought SelectStar - and What "Data Catalog" Means Now w/ Shinji Kim | Shinji Kim, founder of SelectStar (acquired by Snowflake in December), joins the show to discuss the deal, the integration into Snowflake's Horizon catalog, and where data cataloging is actually headed.We get into the weeds on a claim Shinji makes early: in a few years, we may stop calling these things "data catalogs" at all. The category is evolving into an AI context layer, a living surface that combines metadata, semantic models, business glossaries, and ontologies, continuously updated by both humans and agents. Shinji walks through how SelectStar built toward this with semantic model management, MCP server support, and an AI agent that started serving data analysts and eventually answered business users' questions directly.We also dig into where data catalog implementations go wrong (spoiler: it's almost always adoption, not tooling), why marketing teams are an underrated ETL persona, and what it actually took to get acquired by Snowflake after three years as a premier partner.Plus: if Shinji were starting SelectStar today, what would she do differently? We talk about distribution in the AI era and how the startup playbook is mutating.Connect with Shinji:LinkedIn — https://www.linkedin.com/in/shinjikim/ | — | ||||||
| 4/24/26 | WTF is a Software Moat in 2026? - Freestyle Friday (4/24/2026) | AI has completely inverted how we build and scale software, which begs the question: What exactly is a moat anymore? In this Freestyle Friday, recovering from jet lag and hiking through the beautiful hills of Salt Lake City, I’m breaking down a recent conversation with a VC friend about defensibility in the era of coding agents. I also look at this through Charlie Munger’s lens of "inversion" to figure out what isn't a moat anymore (spoiler: thin foundation model wrappers, "AI", and feature velocity are dead).I also dive into what is defensible today, from mission-critical systems of record like DuckDB and Postgres, to personal branding, to shifting SaaS pricing from per-seat to per-token. | — | ||||||
| 4/23/26 | The Future of Open Data Infrastructure with George Fraser (CEO of Fivetran) | Are vendors trying to lock down your data? In this episode, George Fraser breaks down why the "modern data stack" has evolved into "open data infrastructure". We discuss why data gravity is the most overrated concept in data management, how egress charges are often misunderstood due to poorly designed pipelines, and why companies must insist on having a true replica of their own data.George also shares his hands-on experience with AI coding agents, including how he manages his USTA tennis team with bots like OpenClaw and NanoBot. | — | ||||||
| 4/17/26 | We're in 1905: Why Electricity (Not Dot-Com) Is the Right AI Analogy - Freestyle Friday, 4/17/2026 | Walking through Tokyo and breaking down the reality of the AI revolution. In this Freestyle Friday from Shibuya Crossing, I look past the current AI hype cycle to examine the real bottlenecks of AI adoption. Is the current AI boom just a repeat of the dot.com bubble? Why is simply buying Copilot subscriptions for your team failing to move the needle?Drawing parallels to the 40-year adoption curve of the electric grid, I discuss why most AI projects fail to get traction in the enterprise. Hint: it's not the technology, it's the organization. Plus, a look at the danger of firing employees before capturing their tacit knowledge, and how to actually rewire your business to be AI-native. | — | ||||||
| 4/14/26 | The Godfather of Data Governance: Bob Seiner on Data vs AI Governance, and The Data Catalyst Cubed | In this episode, I sit down with Bob Seiner, a true pioneer who has been working in data governance since before it was even called governance. We dive into why he calls BS on the trendy term "data enablement" and how his trademarked approach, Non-Invasive Data Governance, formalizes what organizations are already doing without beating employees over the head.We also unpack his latest concept, The Data Catalyst Cubed, and get into a fascinating discussion about the precarious state of data security in the age of LLMs and autonomous AI agents like OpenClaw. Plus, Bob shares some great war stories about building the T-DAN newsletter using Microsoft FrontPage back in 1997 and drops his best advice for standing out and building a personal brand in the noisy data industry.Where to find Bob:KIK Consulting: kikconsulting.com LinkedIn: / robert-s-seiner-445313 Books: Non-Invasive Data Governance and The Data Catalyst Cubed | — | ||||||
| 4/10/26 | Do Data Fundamentals Still Matter in the Age of AI? - Freestyle Friday (April 10, 2026) | Do fundamentals still matter, or are we all just "vibe engineering" our architectures now? Coming to you live and sweating from the hillsides of Phuket, Thailand, this week's Freestyle Friday dives into the tension between chasing the newest tech and mastering first principles. After a recent LinkedIn debate suggesting teams "don't have time" for fundamentals anymore, I had to set the record straight.I cover why building data platforms without a theoretical framework is like building a house on a Thai hillside without a geologist (spoiler: it ends in a mudslide), the limits of Kimball, and why the rise of AI actually guarantees that data engineering is going to become more critical, not less.Plus, an update on my upcoming book, Mixed Model Arts, and where you can catch me keynoting around the world in the coming months.Links to my Upcoming Events:April 29: Agentic Analytics Summit (Cube)May 6-8: Data Innovation Summit (Stockholm, Sweden). Catch my Keynote on May 7th and my Mixed Model Arts workshop on May 8th!May 18-20: Current (London, UK) | — | ||||||
| 4/8/26 | Wes McKinney on AI Agents, The Mythical Agent Month, and His Wild AI Coding Setup | Wes McKinney is back to discuss his complete transition from AI skepticism to becoming heavily "locked in" on coding agents.Wes shares how he overcame his initial "existential dread" about the future of software engineering and completely rebuilt his personal productivity stack using tools like Claude and Codex. We dive deep into the reality of coding agents, why he believes Go has become the ultimate language for AI agents, and how he manages massive, multi-agent workflows to build production-level software without touching DevOps. Wes also breaks down his mission to fight the platform decay of services like Gmail by building his own local data sovereignty tools. | — | ||||||
| 4/3/26 | Surviving the AI Grind: Hustle Culture, Fear, and Finding Value w/ Eric Weber (Freestyle Friday Episode) | In this Freestyle Friday episode, I catch up with Eric Weber after our recent walk through downtown San Francisco. We dive deep into the very real fear and identity crises sweeping through the tech industry as AI accelerates. We discuss how packing a year of change into a single week is disorienting workers and how the constant hustle culture in SF might finally be hitting its threshold.We also get into the darker side of this shift, including the "reverse centaur" effect where humans are reduced to parts of a machine. Are white-collar engineers about to face the Amazon warehouse treatment through token consumption leaderboards? Eric also shares why he took a step back from leadership, his focus on writing, and the importance of genuine human connection right now.Eric Weber: https://www.linkedin.com/in/ericweberdata/ | — | ||||||
| 4/2/26 | Why 90% of Your Data is Wasted (and How AI Reclaims It) w/ Amit Prakash | I recently sat down with Amit Prakash, the brilliant mind who co-founded ThoughtSpot and led AI teams at Google and Microsoft, to talk about a massive shift happening in the data world.For decades, we’ve been forcing the "messy reality" of business into rigid database tables, losing about 90% of the actual information in the process.Amit is now building Ampup to flip that script. We dive deep into how he’s using dynamic ontologies to extract high-fidelity insights from unstructured data, like the nuances of a 60-minute sales call—to drive massive ROI.In this episode, we explore:- The "SaaSpocalypse" and the Future of Agents: Why the early stages of the sales cycle might soon be a "dance" between AI buying and selling agents.- Sales as Athletics: Why high-stakes negotiation is more like football than a desk job.- The "Business Brain": Moving beyond simple CRMs to a central strategy engine that understands every department’s unstructured data.- Human-to-Human Trust: Why large contracts will always require a human touch, even in an AI-saturated world.- Amit’s perspective on how AI can deliver real value to the GDP by fixing the "distribution bottleneck" of innovation is a must-listen for anyone in tech, data, or leadership. | — | ||||||
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| 3/31/26 | Breaking Into Data Engineering in 2026: AI Tools, Standout Resumes, and more w/ Chris Gambill | In this episode, I sit down with Chris Gambill, a data strategy and engineering leader, fractional consultant, and career coach. We dive into the realities of the data engineering job market in 2026, exploring what it takes to stand out, the massive shift AI coding tools are causing, and why mastering the fundamentals of data engineering remains crucial.Chris shares his unfiltered thoughts on coaching career switchers into data engineering , why finance professionals make great data engineers , and the exact resume and portfolio strategies hiring managers are actually looking for. We also get into the weeds on the latest AI development tools, comparing GitHub Copilot, Claude, and Codex. If you're looking for solid, no BS advice on the field of data engineering in 2026, this is a great discussion!Gambill Data Engineering: https://www.gambilldataengineering.com/LinkedIn: https://www.linkedin.com/in/databasemanagement/ | — | ||||||
| 3/27/26 | AI in Healthcare - The Real-World Realities w/ Gowtham Chilakapati | In this episode, I sit down with Gowtham Chilakapati, an analytics veteran of 18 years and Executive Director at Humana , to pull back the curtain on the reality of Agentic AI in the enterprise.We dive deep into the recent wave of tech layoffs—like the news of Block cutting 40% of its workforce —and debate whether AI is truly driving these decisions or simply serving as a convenient excuse for broader management failures.Gowtham shares his firsthand experience navigating an astounding $1 billion AI investment during the early adopter rush of 2024. He details the chaotic first six months of that initiative and the multi-dimensional framework his team developed to measure true return on investment beyond the traditional, and often flawed, software implementation mindset. From the massive risks of pasting PII into LLMs to how AI prototyping is finally bridging the historic gap between product and engineering teams, this conversation is a masterclass in pragmatism for anyone looking to cut through the AI hype, especially in highly regulated industries. | — | ||||||
| 3/24/26 | Inside the AI "Frankenact" Disaster & The Fight for Developers w/ Jake Ward | In this episode, I sit down with Jake Ward, founder of the Application Developers Alliance. We dig into the AI "Frankenact," aka the EU AI Act, and why policymakers regulating tech they fundamentally misunderstand creates a cold wind for software innovation.Jake drops some harsh truths about why giving developers a voice in Washington is harder than it looks, why collective bargaining and developer unions probably won't work, and how bad policy is forcing companies to build for compliance rather than ship great products. | — | ||||||
| 3/17/26 | Is SaaS Cooked? Why "Local First" AI Agents Are Taking Over w/ Demetrios Brinkmann | In this episode, I sit down with Demetrios Brinkmann (godfather of the MLOps Community) to talk about the absolute Wild West of AI right now. We cover how fast coding agents are changing the game, the reality of "vibe coding" your own CRM , and how Demetrios's community saved $20,000 just by ditching bloated enterprise tools.But we don't just talk tech. We get into the weeds on the content creation pipeline, from the bizarre rise of AI OnlyFans to the "Doorman Paradox" of automated content. Finally, we spill some serious inside baseball on the tech sponsorship game, calling out the sheer audacity of heavily-funded startups expecting free labor from communities , and why protecting your reputation is worth more than any quick paycheck. | — | ||||||
| 3/13/26 | The Buzzword Industrial Complex, AI Agents & The Future of Data w/ Matt Housley | In this episode, Matt Housley and I reunite for a Friday catch-up, bringing back some of that classic Monday Morning Data Chat energy. We dive into the absurdity of the "buzzword industrial complex," and why declaring it the "Year of Context" is mostly just industry hype, per usual.We also tackle the chaotic reality of deploying AI agents (including the ultimate YOLO, OpenClaw) without proper data governance, the Anthropic class action lawsuit regarding copyright, and why regional conferences like DataTune are awesome. Finally, we discuss the shifting landscape of media, the death of traditional book publishing models, and the rise of the independent, niche creator. | — | ||||||
| 3/12/26 | The Tech Job Market is Brutal. Is Freelancing Your Plan B? w/ Jody Hesch | The white-collar tech industry isn't what it used to be, and anyone could be on the chopping block at a moment's notice. With tens of thousands of highly skilled people getting laid off from Big Tech on a seemingly bi-weekly basis, competing in the traditional job market is brutal right now.In this episode, Jody Hesch and I discuss why building a freelance data consulting business isn't just a career pivot—it is a necessary Plan B. We break down the exhaustion of constantly reinventing yourself and navigating new team dynamics every time you switch full-time roles. We also explore the counterintuitive reality that by going freelance, you only have to build your network and reputation once to create a repeatable motion. Whether you are actively looking for an exit or just realizing that the gig economy is coming for data engineering, this conversation covers the realities of making the jump. | — | ||||||
| 3/10/26 | The OGs of AI Analytics: Building Data Agents Before It Was Cool w/ Paul Blankley and Ryan Janssen | In this conversation, Paul Blankley and Ryan Janssen, founders of Zenlytic, drop in to discuss the massive shift in how we build software and handle data. We trace their journey from studying early NLP and Transformers at Harvard right when the BERT paper dropped, to building a company that relies on cutting-edge LLMs. As far as I know, they're the first to use LLM's for analytics.We dive deep into the reality of the agentic era: engineers are no longer writing the bulk of the code; they are managing agents, verifying outputs, and maintaining ridiculously high standards. We also explore why the industry needs to embrace "net negative scaffolding" as models get smarter, and why having good "taste" might be the ultimate human moat left in tech.Bonus: To prove that software development is changing faster than ever, we literally "vibe coded" a brand-new CRM called "Slop Force" in 20 minutes during this episode. Zenlytic: https://www.zenlytic.com/ | — | ||||||
| 3/5/26 | Are Software Engineers the New Data Engineers? w/ Tim Delisle & Chris Crane (514) | In this conversation, I sit down with Tim Delisle and Chris Crane, co-founders of 514, to discuss bridging the gap between software development and data engineering. We cover their experience leading global data engineering at Nike and why software teams are increasingly taking ownership of heavy analytical workloads.We also dive into how they are building the Moose Stack to give developers a local-first, code-first analytics experience. Finally, we explore how AI co-pilots are acting like an "army of interns" to fundamentally change how we write code , and why the "personal data lake" might be the future of privacy and local compute.Check out 514 & The Moose Stack: https://www.fiveonefour.com/ | — | ||||||
| 3/3/26 | The AI Orchestrator & Building Human-Machine Teams w/ Sadie St. Lawrence | Sadie St. Lawrence joins me to unpack her concept of the "AI Orchestrator," explaining how it shifts our mindset from being a musician to a conductor in the age of AI. She shares insights from her work at the Human-Machine Collaboration Institute (HMCI), detailing how her team is building AI-powered solutions and tackling complex problems. We also chat about the common pitfalls in AI adoption, from unfounded fears to "work slop," and why foundational systems thinking remains paramount. | — | ||||||
| 2/26/26 | Marketing to Developers During the AI Gold Rush w/ Prashant Sridharan | In this episode, I sit down with Prashant Sridharan, a 30-year veteran of developer marketing who has shaped go-to-market strategies for tech giants like Sun Microsystems, Microsoft, AWS, Facebook, and Twitter, and currently runs product marketing at Supabase. We dive deep into the origins of DevRel and how marketing to developers has evolved in an increasingly noisy, AI-saturated landscape.Topics covered:- Transitioning from massive tech companies to the fast-paced startup world - How to genuinely measure the success of Developer Relations without ruining communities - Using AI tools like Claude to accelerate mechanical marketing tasks while preserving authentic storytelling - The shift from traditional SEO to GEO (Generative Engine Optimization) for developer tools - The thrill of live, unscripted coding demos and stories from sharing the stage with Steve Ballmer - Prashant's upcoming fiction novel, The Midnight Coders Children, and the craft of writing Find more from Prashant at StrategicNerds.com and check out his non-fiction book, Picks and Shovels: https://amzn.to/4cJ2TRO | — | ||||||
| 2/17/26 | From ODBC to ADBC: Modernizing the Data Stack for AI and Analytics w/ Ian Cook | Why are we still using row-based protocols like ODBC and JDBC in a column-oriented world? In this episode, I sit down with Ian Cook, co-founder of Columnar and a long-time Apache Arrow contributor, to discuss the critical infrastructure changes needed to speed up modern analytics and AI.We dive deep into the technical bottlenecks of legacy standards - specifically the "serialization tax" of converting columns to rows and back again - and how ADBC (Arrow Database Connectivity) solves this by keeping data columnar from end-to-end. Ian also shares his insights on the intersection of tabular data and LLMs, why AI agents need better access to OLAP systems, and the tension between vibe coding speed and the stability required for critical open-source infrastructure. | — | ||||||
| 2/11/26 | Vibe Coding, Agents, and The Future of Streaming Data w/ Paul Dudley and Ricky Thomas (Streamkap) | I sat down with Paul Dudley (CEO) and Ricky Thomas (CTO) from StreamKap to catch up on where the world of streaming data is heading—and things have changed fast since we last spoke.We dive into the concept of "vibe coding" and how AI is radically accelerating how we build software (I even share a story about building a data analysis tool in an hour). But the real meat of this conversation is about the intersection of streaming data and AI agents. Everyone is building agents, but without real-time context, they’re flying blind. We discuss why streaming is a missing link for agentic workflows, the shift from dashboards to automated decision-making, and why SaaS companies are racing to build walled gardens around their data.We also get into the nitty-gritty of the UK vs. US tech markets, the resurgence of PR in the AI era, and StreamKap’s upcoming move into the Snowflake native app ecosystem.Streamkap: https://streamkap.com/ | — | ||||||
| 2/4/26 | Dashboards vs. Agents: Navigating the New Era of BI and Analytics with Mike Driscoll | In this episode, I sit down with Mike Driscoll, founder of Rill Data, to discuss the evolving landscape of business intelligence and data engineering. We explore why the industry keeps "rediscovering" old concepts like the semantic layer and how the rise of AI agents is forcing us to rethink how we structure data.Mike shares his insights on the "shape" of analytics, debating whether conversational interfaces will replace dashboards or simply complement them. We also dig into the growing demand for data engineering, the importance of watermarks and temporal semantics, and why data visualization remains a critical tool for "trust but verify" in an AI world.Rill Data Mike’s Podcast: Data Talks on the Rocks | — | ||||||
| 1/28/26 | "I Needed to Be Back in the Game": Leaving PE & Big Tech to Build Vertical AI w/ Lak Lakshmanan | Lak Lakshmanan had a successful career in Private Equity and Big Tech, but he realized he couldn't just "coach the game" while the rules were changing. He had to get back on the field play it. We discuss vertical AI, the "foolhardiness" required to start a company , the reality of the AI technology wave, and why sitting on the sidelines is the biggest risk of all.LinkedIn: https://www.linkedin.com/in/valliappalakshmananGenerative AI Design Patterns (book): https://amzn.to/45v0xBO | — | ||||||
| 1/21/26 | Cory Doctorow on Enshitification, The AI Bubble, Reverse Centaurs, and The Post-American Internet | In this episode, I sit down with science fiction author, activist, and journalist Cory Doctorow to unpack his viral concept of Enshitification, the three-act tragedy of platform decay: 1. be good to users 2. lock them in 3. extract value from users to feed advertisers and shareholdersWe also dive into:- The AI bubble: Cory’s case that parts of the sector are propped up by aggressive accounting and incentives, not durable value.- The “Reverse Centaur”: How workers (from Amazon drivers to radiologists) are being reorganized to serve machine workflows, rather than machines serving humans.- Software engineering vs. “vibe coding”: Why autocomplete isn’t engineering, and why AI can’t replace process knowledge and domain context.- The Post-American Internet: What happens when the U.S. weaponizes platforms, and the rest of the world builds alternatives.About Cory Doctorow: Cory is a multi-time international bestselling author, special advisor to the Electronic Frontier Foundation, and creator of the blog/newsletter Pluralistic.If you got value from this conversation, hit Follow and share it with one person who cares about the future of tech. | — | ||||||
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