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- 🇮🇸IS · Technology#190500 to 3K
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150 to 900🎙 Daily cadence·367 episodes·Last published 5d ago - Monthly Reach
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200 to 1.2K
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Recent episodes
The AI Boom (and Bust?) Cycle: Lessons from the Gold Rush. Freestyle Fridays (June 19, 2026)
Jun 19, 2026
Unknown duration
The Missing Half of AI: Context, Agents, and the AI-Native Enterprise w/ Prukalpa Sankar (Atlan)
Jun 11, 2026
Unknown duration
Snowflake Summit 2026 Recap, Avoiding the Semantic Swamp, and more w/ Juan Sequeda
Jun 9, 2026
Unknown duration
Data Work in the Real World (Detroit Edition) w/ Ryan Dolley. Freestyle Fridays (June 5, 2026)
Jun 5, 2026
Unknown duration
How AI Agents Are Changing the Data Consultancy Game w/ Chris Tabb (Confluent Current London 2026)
May 29, 2026
Unknown duration
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| Date | Episode | Description | Length | ||||||
|---|---|---|---|---|---|---|---|---|---|
| 6/19/26 | ![]() The AI Boom (and Bust?) Cycle: Lessons from the Gold Rush. Freestyle Fridays (June 19, 2026) | Finished a jog on the high plains near South Pass, Wyoming, where there's a lot of history. Standing near the old Oregon and Mormon trails, I look at the remnants of the 1800s gold rush to draw parallels to the current AI boom. | — | ||||||
| 6/11/26 | ![]() The Missing Half of AI: Context, Agents, and the AI-Native Enterprise w/ Prukalpa Sankar (Atlan) | In this episode, I sit down with Prukalpa Sankar, the founder of Atlan, to discuss the missing piece that makes artificial intelligence actually useful in the enterprise: context. We dive deep into building the "second brain" of a company, the reality of agent development, and how to transition a traditional business into an AI-native organization. If you're looking to understand why your AI agents are getting abandoned in testing hell or how the roles of data and engineering are fundamentally shifting, this is the conversation for you. As always, we keep it practical and grounded. No hype, just education from the front lines of data architecture.What an Enterprise Context Layer Actually Is (Prukalpa's new article): https://www.linkedin.com/pulse/what-enterprise-context-layer-actually-prukalpa--avdqc/?trackingId=kq8lIdYdRnKsHu%2BdREYB3Q%3D%3DTimestamps01:15 - The missing half of AI: Contextual intelligence 02:15 - Reverse engineering business context and the second brain 05:06 - Escaping testing hell and hitting the 80% accuracy threshold for agents 07:54 - Simulating context for analytics use cases 11:34 - Does data quality matter for AI agents? 15:37 - Capturing tacit knowledge and human expertise 21:08 - The organizational chart of the future and "E-shaped" humans 26:26 - How Atlan transformed into a completely AI-native company 34:22 - Banning engineers from coding and the new mental model for work 39:05 - Societal resistance, historical context, and embracing technological change 46:00 - Optimism, childlike curiosity, and the path forward | — | ||||||
| 6/9/26 | ![]() Snowflake Summit 2026 Recap, Avoiding the Semantic Swamp, and more w/ Juan Sequeda | Juan Sequeda stops by after a massive month on the road to unpack the latest industry shifts, including takeaways from the Snowflake Summit. We dive into the real state of AI agents in the enterprise, separating the hype from the reality of adoption. We also explore the dangers of creating a "semantic swamp," (cousin of data swamps) the shifting landscape of vendor strategies with the rise of the modern monolith, and why data teams need to accept that getting work done (not data) is the true center of the universe. Finally, we discuss why pragmatism beats pedantry every time when building data architecture.🎙️ SPONSORSRevify - surprise Snowflake bills? One customer cut theirs 50% in 48 hours.→ https://revify.com/demo | — | ||||||
| 6/5/26 | ![]() Data Work in the Real World (Detroit Edition) w/ Ryan Dolley. Freestyle Fridays (June 5, 2026) | In this Freestyle Friday episode, Ryan Dolly and I record straight from the historic Guardian Building in downtown Detroit to talk about life, tech, and data outside the San Francisco bubble. We had an amazing time connecting at the Data in the D town hall and exploring a city undergoing massive revitalization. Detroit was once the Silicon Valley of its time, peaking at nearly 1.9 million residents. Now, the city has a tangible "comeback" energy, moving past its history of empty fields and boarded-up buildings to build something entirely new. We discuss why building a career away from the coasts offers incredible lifestyle advantages, especially if you want to avoid the hyper-focus on AI software tools and work with real-world physical assets like automotive, mobility, and robotics.I'm excited about Detroit's potential and plan to spend more time here.🎙️ SPONSORSRevify - surprise Snowflake bills? One customer cut theirs 50% in 48 hours.→ https://revify.com/demo | — | ||||||
| 5/29/26 | ![]() How AI Agents Are Changing the Data Consultancy Game w/ Chris Tabb (Confluent Current London 2026) | If you're a consultant and you're not using AI agents yet, your competitors are. No surprise, but they're delivering faster, cheaper, and better than ever.Chris Tabb, founder of LEIT Data, joins me live at Confluent Current London 2026 to talk honestly about how AI agents are reshaping the consultancy model, from billing structures and team rollouts, to building internal tribal knowledge and outpacing firms that are still staffing up the old way.Timestamps:0:33 — How Chris is Going Agentic1:56 — Token Maxing Leaderboards5:26 — AI Agents: Year-Over-Year7:08 — Tagile: Agentic Development9:00 — AI in Consultancy17:22 — Prompt Management & Context Quality | — | ||||||
| 5/27/26 | ![]() Why You Feel Behind in AI (And Aren't) w/ Eric Weber | Everyone in tech is telling you to go faster. Eric stepped away from his role to do the opposite.In this conversation, we get into why so many people feel like they're falling behind in AI, and why that feeling is mostly manufactured. Eric makes the case that we're miscalibrated: assuming what's true for the 0.1% (the SF AI inner circle) is true for the 10%, when by definition almost no one is keeping up with that group. We talk about why judgment, not throughput, is the real bottleneck right now, why most AI products feel boring even as code output explodes, what the "flatten the org" experiments are actually measuring (spoiler: yesterday's stock price), and why people are leaving corporate roles at a rate that's hard to ignore.We also get into the parts nobody wants to say out loud: layoffs by email, the gap between who people are in private vs. on LinkedIn, the ghost routines after you leave a job, and what walking around San Francisco actually feels like when every billboard is AI and every person you pass looks depleted.If you've felt the FOMO and wondered whether the problem is you or the framing, this one's for you.Eric Weber is a data and product leader formerly at Grammarly, Yelp, LinkedIn, and Stitch Fix. | — | ||||||
| 5/20/26 | ![]() Why AI Agents Are the New Consumers of Data with Tristan Handy (CEO @dbt Labs) | In this episode, Tristan Handy and I sit down to unpack a massive shift coming to the data industry: over the next 12 months, the primary consumers of data won't be humans. They will be AI agents. We dive deep into what this means for data infrastructure, compute costs, and the tools we use every day. We also talk about processing high-volume agent queries, building "context stores", and why the industry shouldn't just build "horses with wheels" when designing agentic data engineers. We also take a fun detour comparing the current AI landscape to the early days of dial-up modems and Mosaic browsers , and discuss why stepping away from the screen and going old-school might be the ultimate productivity hack. | — | ||||||
| 5/15/26 | ![]() Why 90% of Data Teams Are Failing at Modeling - Freestyle Friday (May 15, 2026) | NOTE - Sorry for the edits in this video. I used Descript to edit out the umms and uhhs, and it was a bit too aggressive. Will make it less jarring in future videos. Thanks.Freestyle Friday, May 15, 2026Walking around Salt Lake City and unpacking the April 2026 data modeling survey results (334 respondents). Across three surveys now: January's State of Data Engineering (1,100), March's AI usage poll (193), and April's data modeling deep-dive. Not surprisingly, the same two pain points keep surfacing: time pressure and lack of clear ownership.90% of respondents have a data modeling pain point. When asked what would actually help, only 4.8% wanted better tools. Training, business requirements, time, and ownership crushed tooling in the rankings. Will AI improve things or make them worse? Time will tell...Also covered:Why physical data modeling has become the default (and why that's a problem)Data modeling vs. schema design - they're not the same thingSemantic layers (yay or nay?), Lloyd Tabb, and MalloyConway's Law, Reis's Law, and what changes when org charts get flattened by AIWhy leadership is under more pressure than everThe June half-year survey is coming🎙️ SPONSORSFivetran - stop cobbling pipelines together. Set it, forget it, scale as you grow.→ https://fivetran.comRevify - surprise Snowflake bills? One customer cut theirs 50% in 48 hours.→ https://revify.com/demo | — | ||||||
| 5/14/26 | ![]() The Hidden Costs of AI Agents & Cloud Data with Sanjay Agrawal (Revefi, co-founder ThoughtSpot, MS) | Are AI agents silently draining your cloud data budget? With the rise of consumption-based pricing and autonomous AI queries, data teams are facing a perfect storm of skyrocketing costs and operational chaos. In this episode, I sit down with Sanjay Agrawal, CEO and Co-founder of Revefi, to discuss the intersection of data engineering, cloud warehouse optimization, and FinOps in the age of AI.We chat about how legacy on-prem habits are bankrupting modern data platforms, why query optimization is more about ROI than just speed, and how AI agents are changing the landscape of data consumption. Sanjay shares his deep expertise from building world-class databases at Microsoft and ThoughtSpot, revealing how to automate cost management and performance tuning for Snowflake, Databricks, and BigQuery.Key Topics:The evolution of cloud data warehouse pricing and why it breaks traditional budgets.How AI agents are causing massive, unpredictable spikes in compute spend.Real-world horror stories of ""lift and shift"" cloud migrations.Why database benchmarks focus on speed but ignore the actual ROI of data.The future of open table formats (Iceberg) and multi-engine routing. | — | ||||||
| 5/9/26 | ![]() Zach Wilson - Data Engineering in 2026, Traveling, and more - Freestyle Fridays - May 8, 2026 | Zach Wilson and I happen to be in Stockholm, Sweden, this evening. In this Freestyle Friday chat, we talk about what it takes to be a data engineer in 2026 and much more. | — | ||||||
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| 5/7/26 | ![]() AI Agents Can't Fix Data - Josh Wills on Where AI Breaks in Data Engineering | Josh Wills has spent 25 years writing data pipelines, with a career spanning Cloudera, as Director of Data Engineering at Slack, on the dbt DuckDB adapter, and now training foundation models at Datology AI. He uses coding agents every day. And he keeps running into the same wall: the agents jump to conclusions, fix the wrong thing, and ship pipelines no one understands.In this conversation, we unpack why AI agents struggle with the messiest, highest-stakes parts of data work, and what it means for the engineers managing them.We get into:- Big Data is back- Why AI agents jump to conclusions on benchmarks and complex bottlenecks- The $200K vibe-coded pipeline problem nobody wants to talk about- Why there's no training data for the gnarly enterprise pipelines that actually power businesses- "We're all managers now" - managing unreliable agents like managing unreliable people- Wicked problems and the limits of intelligence- Why politics is the last human endeavor to fall to LLMs (the data is never written down)- Whether classical ML still has a place (yes)- What Josh would tell a new grad starting in data today | — | ||||||
| 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. | — | ||||||
| 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. | — | ||||||
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Chart Positions
1 placement across 1 market.
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