The Reasoning Show - podcast cover

The Reasoning Show

Massive Studioswww.reasoning.show

The Reasoning Show AI moves fast. Thinking clearly matters more.


The Reasoning Show cuts through the hype to explore how the smartest people in enterprise AI actually make decisions — the strategy, the tradeoffs, and the hard lessons no press release mentions.


Every week, hosts Aaron Delp and Brian Gracely sit down with the founders building the tools, investors funding the shift, and operators running AI in the real world. Not hype. Not panic. Just clear-headed conversations with people who have to make actual decisions.


Because the AI revolution isn't just happening. It's being reasoned through. 

New shows every Wednesday and Sunday. 


Topics: Enterprise AI strategy · LLMs in production · AI leadership · Agentic AI ·  Digital Sovereignty · Machine Learning · AI startups ·  Cloud Computing 

Last refreshed:
Follow this podcast in the Metacast mobile app to refresh it and see new episodes.
Download Metacast podcast app
Podcasts are better in Metacast mobile app
Don't just listen to podcasts. Learn from them with transcripts, summaries, and chapters for every episode. Skim, search, and bookmark insights. Learn more

Episodes

The 2026 AI Draft

SUMMARY: Draft guru Brandon Whichard (Software Defined Talk) joins us for the inaugural AI Draft, where we predict the next year of AI winners, losers, trends, and headlines. GUEST: Brandon Whichard, Software Defined Talk SHOW: 1024 SHOW TRANSCRIPT: The Reasoning Show #1024 Transcript SHOW VIDEO: SHOW SPONSORS: ShareGate - ShareGate Protect. Microsoft 365 Governance, we got this! Nasuni - Activate your data for AI and request a demo SHOW NOTES: Brian’s Picks Google Major AI-centric IPO in 2026 (...

May 03, 202644 min

Halt & Retool: Rewriting Software Development in the Age of AI Agents

SUMMARY: Exploring how to fully embrace AI-driven, agent-based software development, resulting in dramatically increased productivity and faster feature delivery. It highlights a broader shift in engineering—from writing code to orchestrating AI agents. GUEST: Sam Ramji , CEO/Co-founder at Sailplane SHOW: 1023 SHOW TRANSCRIPT: The Reasoning Show #1023 Transcript SHOW VIDEO: https://youtu.be/q50s0oL37pQ SHOW SPONSORS: Nasuni - Activate your data for AI and request a demo ShareGate - ShareGate Pro...

Apr 29, 202635 min

The Zero-CVE Mirage: Hardening Software in the Age of AI Attacks

SUMMARY: How software development is rapidly evolving in the age of AI and automation. Matt Moore shares how his team is rethinking secure software supply chains, scaling infrastructure, and safely integrating AI agents into development workflows. GUEST: Matt Moore , CTO at Chainguard SHOW: 1022 SHOW TRANSCRIPT: The Reasoning Show #1022 Transcript SHOW VIDEO: https://youtu.be/9Q0kWkTYRs8 SHOW SPONSORS: ShareGate - ShareGate Protect. Microsoft 365 Governance, we got this! Nasuni - Activate your d...

Apr 26, 202635 min

The Grid’s Breaking Point: Can AI Save the Infrastructure It’s About to Crash?

SUMMARY: How real-time power flow optimization at the edge is helping data centers and the electrical grid handle surging AI energy demands more efficiently. By unlocking hidden capacity and dynamically managing power systems, we explain how existing infrastructure can support significantly more compute without massive new buildouts. GUEST: Marissa Hummon , CTO Utilidata SHOW: 1021 SHOW TRANSCRIPT: The Reasoning Show #1021 Transcript SHOW VIDEO: https://youtu.be/ItcpU8UjOFE SHOW SPONSORS: Nasuni...

Apr 22, 202625 min

Shadow AI is Faster Than Your Governance: Why Guardrails are Failing

SUMMARY: Shadow AI is growing much faster than known AI adoption across businesses. How can IT teams get Shadow AI under control? GUEST: Uri Haramati , CEO at Torii SHOW: 1020 SHOW TRANSCRIPT: The Reasoning Show #1020 Transcript SHOW VIDEO: https://youtu.be/AUrh_xICPzM SHOW SPONSORS: ShareGate - ShareGate Protect. Microsoft 365 Governance, we got this! Nasuni - Activate your data for AI and request a demo SHOW NOTES: Torii (homepage) Topic 1 - Welcome to the show. Tell us about your background a...

Apr 19, 202629 min

The Junior Dev Crisis: Who Inherits the Code When AI Does the Work?

SUMMARY: Have we reached a point where coding is a solved problem? And if so, what are the downstream effects on companies that need software to differentiate their business? GUEST: Brandon Whichard , Co-Host of Software Defined Talk SHOW: 1019 SHOW TRANSCRIPT: The Reasoning Show #1019 Transcript SHOW VIDEO: https://youtu.be/q0mksIKcBzk SHOW SPONSORS: ShareGate - ShareGate Protect. Microsoft 365 Governance, we got this! Nasuni - Activate your data for AI and request a demo SHOW NOTES: The New Ki...

Apr 15, 202633 min

RAG Won’t Save Your Messy Data: The Brutal Truth About AI Reliability

SUMMARY: The RAG (Retrieval Augmented Generation) pattern is one of the most frequently used to augment LLMs with context-specific information. Let’s explore RAG. GUEST: Roie Schwaber-Cohen , Head of Developer Relations at Pinecone SHOW: 1018 SHOW TRANSCRIPT: The Reasoning Show #1018 Transcript SHOW VIDEO: https://youtu.be/-kZZEMR341Q SHOW SPONSORS: Nasuni - Activate your data for AI and request a demo ShareGate - ShareGate Protect. Microsoft 365 Governance, we got this! SHOW NOTES: Topic 1 - We...

Apr 12, 202629 min

The Productivity Paradox: Why More AI Code is Slowing Down Shiptimes

SUMMARY: Discover how AI is transforming software development and what it means for engineering leaders. GUEST: Jeff Keyes , Field CTO at AllStacks SHOW: 1017 SHOW TRANSCRIPT: The Reasoning Show #1017 Transcript SHOW VIDEO: https://youtu.be/cXPu8iWeB0k SHOW SPONSORS: ShareGate - ShareGate Protect. Microsoft 365 Governance, we got this! Nasuni - Activate your data for AI and request a demo SHOW NOTES: Topic 1 - Welcome to the show. Tell us a little bit about your background, and what you focus on...

Apr 08, 202634 min

The Production Chaos: Why AI-Generated Code is Breaking Traditional SRE

SUMMARY: With the explosion of AI-generated code and applications, the modern SRE requires an AI-native approach to managing complex systems. GUEST: Anish Agarwal - CEO/Cofounder of Traversal SHOW: 1016 SHOW TRANSCRIPT: The Reasoning Show #1016 Transcript SHOW VIDEO: https://youtu.be/hF3MCRDhMno SHOW SPONSORS: Nasuni - Activate your data for AI and request a demo ShareGate - ShareGate Protect. Microsoft 365 Governance, we got this! SHOW NOTES: Traversal (homepage) Topic 1 - Welcome to the show. ...

Apr 05, 202633 min

The Future of Service belongs to Self-Improving AI

SUMMARY: Today’s episode is all about a transformation happening in customer service—one that’s moving us from static systems and scripted workflows into something far more dynamic: AI systems that can actually learn and improve over time. GUEST: Shashi Upadhyay (President of Product, Engineering, and AI at Zendesk) SHOW: 1015 SHOW TRANSCRIPT: The Reasoning Show #1015 Transcript SHOW VIDEO: https://youtu.be/IQaxE-DjIpo SHOW SPONSORS: ShareGate - ShareGate Protect. Microsoft 365 Governance, we go...

Apr 01, 202634 min

The $26B Pivot: Why Big Tech is Abandoning the AI "Wrapper" Model

SUMMARY: Brian (@bgracely) and Brandon Whichard (@bwhichard, Software Defined Talk and Failover Media) discuss the biggest AI news stories from the month of March, 2026. SHOW: 1014 SHOW TRANSCRIPT: The Reasoning Show #1014 Transcript SHOW VIDEO: https://youtu.be/XwyAC-hxOQY SHOW SPONSORS: VENTION - Ready for expert developers who actually deliver? Visit ventionteams.com SHOW NOTES: Links to all the AI News covered in this months show FEEDBACK? Email: show @ reasoning dot show Bluesky: @reasoning...

Mar 29, 202640 min

Living the Claude-centric Life

SUMMARY: With @bwhichard, we dig into how daily work-life changes when you make @AnthropicAI @claudeai the center of all workflow activities. SHOW: 1013 SHOW TRANSCRIPT: The Reasoning Show #1013 Transcript SHOW VIDEO: https://youtu.be/zEmEH0t67js SHOW SPONSORS: VENTION - Ready for expert developers who actually deliver? Visit ventionteams.com SHOW NOTES: Topic 1 - How long have you been living the Claude-life, and when did it dawn on you to make this central to your day-to-day activities? Topic ...

Mar 25, 202637 min

NVIDIA’s Open Software Trap: The Real Cost of the New Inference Stack

SUMMARY: We dig into the NVIDIA GTC keynote and highlight three things - accelerated computing for everything, the complexity of the new inference stack, and NVIDIA’s “open” software stack including NemoClaw. SHOW: 1012 SHOW TRANSCRIPT: The Reasoning Show #1012 Transcript SHOW VIDEO: https://youtu.be/aXOr91q76yM SHOW SPONSORS: VENTION - Ready for expert developers who actually deliver? Visit ventionteams.com SHOW NOTES: NVIDIA GTC 2026 (Keynote) NVIDIA NemoClaw - OpenClaw + OpenShell + NVIDIA Ag...

Mar 22, 202628 min

Kagenti - A Kubernetes Control Plane for AI Agents

SUMMARY: Morgan Foster talks about the Kagenti project, which enables an AI Agent agnostic framework for security, authentication, identity and zero-trust. SHOW: 1011 SHOW TRANSCRIPT: The Reasoning Show #1011 Transcript SHOW VIDEO: https://youtu.be/djFZruLEDiw SHOW NOTES: Kagenti (homepage) Kagenti (use-cases) “Old Things that look like Agents” “What makes Agents different?” CNV - What Makes Agents Different? “Handing your phone to a stranger, why Agents need their own identity” Topic 1 - Welcom...

Mar 18, 202641 min

Your Career is Legacy Code: Why 'All Jobs are Software' is a Warning, Not a Trend

SUMMARY: Brian talks about the rapidly expanding gap between people and companies that augment their work with AI and those who are making AI the center of their work world. SHOW: 1010 SHOW TRANSCRIPT: The Reasoning Show #1010 Transcript SHOW VIDEO: https://youtu.be/tFyLlCnkbsM SHOW SPONSORS: VENTION - Ready for expert developers who actually deliver? Visit ventionteams.com SHOW NOTES: WHY THE NEED FOR A CODE RED? Velocity of Code (new companies) Velocity of Productivity (employees) Velocity of ...

Mar 15, 202621 min

Inside OpenClaw and Open Source Innovation

SUMMARY: Sally O’Malley (Principle Software Engineer @RedHat, Maintainter @OpenClaw) talks about her early experiences of immersing herself into OpenClaw and evolution of the OpenClaw community. SHOW: 1009 SHOW TRANSCRIPT: The Reasoning Show #1009 Transcript SHOW VIDEO: https://youtu.be/7xARBtgiMQg SPONSORS: VENTION - Ready for expert developers who actually deliver? Visit ventionteams.com SHOW NOTES: OpenClaw - Personal AI Assistant OpenClaw - Reddit OpenClaw, OpenAI and the Future (Peter Stein...

Mar 11, 202626 min

Understanding NeoClouds with Crusoe

Erwan Menard - SVP Product Management @CrusoeAI talks about the evolution of NeoClouds, the challenges of matching the speed of data centers, GPUs and software, and how everything is evolving to megawatts and tokens. SHOW: 1008 SHOW TRANSCRIPT: The Reasoning Show #1008 Transcript SHOW VIDEO: https://youtu.be/eA8vpPmSW0Y SPONSORS: VENTION - Ready for expert developers who actually deliver? Visit ventionteams.com SHOW NOTES: Topic 1 - Welcome to the show. Tell us a bit about your background, and w...

Mar 08, 202628 min

Beyond the Chatbot: Why Most "Agents" are Just Glorified Automation

OVERVIEW: Welcome to The Reasoning Show! We dig into one of the foundational building blocks of modern Generative AI, the AI Agent. So what is an AI Agent, and what do we need to think about for the next couple years? SHOW: 1007 SHOW TRANSCRIPT: The Reasoning Show #1007 Transcript SHOW VIDEO: https://youtu.be/4tdj0S0AyhM SHOW SPONSOR: VENTION - Ready for expert developers who actually deliver? Visit ventionteams.com SHOW NOTES: Topic 1 - We’re 3+ years into the Generative AI era. Why do you thin...

Mar 04, 202626 min

AI & Cloud News of the Month - Feb 2026

This episode marks the transition from The Cloudcast to The Reasoning Show, focusing more on AI and cloud topics. Brian Gracely (@bgracely) and Brandon Whichard (@bwhichard, @SoftwareDefTalk) discuss recent trends in AI, the evolution of tech teams, and the shifting landscape of enterprise AI tools. SHOW: 1006 SHOW TRANSCRIPT: The Cloudcast #1006 Transcript SHOW VIDEO: https://youtube.com/@TheCloudcastNET NEW TO CLOUD? CHECK OUT OUR OTHER PODCAST - "CLOUDCAST BASICS" SHOW NOTES: Link to February...

Feb 28, 202642 min

How The Cloudcast is changing in 2026?

Aaron and Brian discuss how The Cloudcast will be changing going forward, signaling an industry shift from Cloud Computing to AI. SHOW: 1005 SHOW TRANSCRIPT: The Cloudcast #1005 Transcript SHOW VIDEO: https://youtube.com/@TheCloudcastNET NEW TO CLOUD? CHECK OUT OUR OTHER PODCAST: "CLOUDCAST BASICS" SHOW NOTES: Topic 1 - What are we announcing? (“The Reasoning Show”, a.k.a. “Reasoning”) New name, same RSS feeds (same podcast players) New logo Some existing/renamed and some new social media channe...

Feb 25, 202618 min

What's Your Token Budget?

This episode explores the evolving economics of AI development, the rising costs associated with AI agents, and the implications for businesses and developers. It highlights the shift from centralized to decentralized computing, the importance of understanding token budgets, and the future of AI project management. SHOW: 1004 SHOW TRANSCRIPT: The Cloudcast #1004 Transcript SHOW VIDEO: https://youtube.com/@TheCloudcastNET CLOUD NEWS OF THE WEEK: http://bit.ly/cloudcast-cnotw CHECK OUT OUR NEW POD...

Feb 22, 202619 min

Evaluating AI Models in 2026

Aaron and Brian review some of the latest AI model releases and discuss how they would evaluate them through the lens of an Enterprise AI Architect. SHOW: 1003 SHOW TRANSCRIPT: The Cloudcast #1003 Transcript SHOW VIDEO: https://youtube.com/@TheCloudcastNET NEW TO CLOUD? CHECK OUT OUR OTHER PODCAST: "CLOUDCAST BASICS" SHOW NOTES: Last Week in AI Podcast #234 Artificial Analysis.AI Opus 4.6 Release GPT Codex 5.3 Release GLM-5 Release OpenAI Preparedness Framework Sam’s Tweet that 5.3 Codex hit “hi...

Feb 18, 202629 min

Three AI Rooms to be a Fly on the Wall in 2026

As we move into Q1 2026, Brian talks about 3 rooms where he'd like to be a fly on wall to see the blueprints of significant AI companies shaping the markets. SHOW: 1002 SHOW TRANSCRIPT: The Cloudcast #1002 Transcript SHOW VIDEO: https://youtube.com/@TheCloudcastNET NEW TO CLOUD? CHECK OUT OUR OTHER PODCAST - "CLOUDCAST BASICS" A FLY ON THE WALL IN 3 ROOMS IN 2026 Room1 - NVIDIA’s M&A Room (Chips, Software Stack, Hosting Services, Agentic Tools, etc.) Room 2 - Anthropic’s Agentic Vision Room ...

Feb 15, 202613 min

What we wish we knew about the next 3 years of AI?

Aaron and Brian explore the evolving landscape of AI over the next three years, discussing its economic implications, political influences, technological advancements, partnership dynamics, changing buying patterns, and the potential impact on job creation and destruction. They emphasize the uncertainty surrounding AI's future and the need for understanding its broader implications. SHOW: 1001 SHOW TRANSCRIPT: The Cloudcast #1001 Transcript SHOW VIDEO: https://youtube.com/@TheCloudcastNET NEW TO...

Feb 11, 202631 min

The Economics of Software Developers

If someone walked into your office today and asked you to build a framework for how to value software development, what would you think about it? SHOW: 1000 SHOW TRANSCRIPT: The Cloudcast #1000 Transcript SHOW VIDEO: https://youtube.com/@TheCloudcastNET NEW TO CLOUD? CHECK OUT OUR OTHER PODCAST - "CLOUDCAST BASICS" SHOW NOTES: Chainguard introduces Factory 2.0 On running a startup of Claude Code agents Agentic Product Development and the Theory of Constraints Software Abundance HOW SHOULD SOMEON...

Feb 08, 202616 min

The Future of Enterprise Software?

Are we ready to move into an era of wild predictions about where the future of Enterprise software is headed in 2026 and beyond? SHOW: 999 SHOW TRANSCRIPT: The Cloudcast #999 Transcript SHOW VIDEO: https://youtube.com/@TheCloudcastNET CLOUD NEWS OF THE WEEK: http://bit.ly/cloudcast-cnotw CHECK OUT OUR NEW PODCAST: "CLOUDCAST BASICS" SHOW NOTES The SPAC-king is going to fix legacy software All Enterprise software is dead Microsoft and Software Survival (Stratechery) WHAT HAPPENS TO ENTERPRISE SOF...

Feb 04, 202627 min

The Rise of Digital Sovereignty

We take a listener question about digital sovereignty, tariffs and UK/EU independence from large US cloud providers, also Brian reaches out to the Melbourne, AUS listeners. SHOW: 998 SHOW TRANSCRIPT: The Cloudcast #998 Transcript SHOW VIDEO: https://youtube.com/@TheCloudcastNET CLOUD NEWS OF THE WEEK: http://bit.ly/cloudcast-cnotw CHECK OUT OUR NEW PODCAST: "CLOUDCAST BASICS" SHOW NOTES AWS European Sovereign Cloud Azure European Sovereign Services Google Cloud Sovereign Cloud Red Hat Digital So...

Feb 01, 202633 min

AI & Cloud Trends for January 2026

Aaron Delp (@aarondelp), Brian Gracely (@bgracely) and Brandon Whichard (@bwhichard, @SoftwareDefTalk) discuss the top stories in Cloud and AI from January 2026. SHOW: 997 SHOW TRANSCRIPT: The Cloudcast #997 Transcript SHOW VIDEO: https://youtube.com/@TheCloudcastNET NEW TO CLOUD? CHECK OUT OUR OTHER PODCAST: "CLOUDCAST BASICS" SHOW NOTES: Link to January 2026 News and Articles FEEDBACK? Email: show at the cloudcast dot net Bluesky: @cloudcastpod.bsky.social Twitter/X: @cloudcastpod Instagram: @...

Jan 28, 202648 min

10 Questions about what Cloud 2.0 might look like

Following on the discussion of the Cloud 1.0 to Cloud 2.0 transition, we explore what that future cloud might look like. SHOW: 996 SHOW TRANSCRIPT: The Cloudcast #996 Transcript SHOW VIDEO: https://youtube.com/@TheCloudcastNET NEW TO CLOUD? CHECK OUT OUR OTHER PODCAST - "CLOUDCAST BASICS" SHOW NOTES: Q1 - What didn’t Cloud 1.0 achieve from the grand vision? Q2 - What seemed promising but might have been the wrong timing? Q3 - Why didn’t more SaaS get bundled by the hyperscalers? Q4 - Does multi-...

Jan 25, 202624 min

The Cloudcast Playbook - Lessons from 1000 Shows

After 1000+ shows of The Cloudcast, when critical lessons have we learned about the industry, our our journey, and tips for anyone in tech. SHOW: 995 SHOW TRANSCRIPT: The Cloudcast #995 Transcript SHOW VIDEO: https://youtube.com/@TheCloudcastNET NEW TO CLOUD? CHECK OUT OUR OTHER PODCAST - "CLOUDCAST BASICS" SHOW NOTES: Lesson 1 - Why did we create The Cloudcast? [Career expansion] Lesson 2 - How did we learn all the topics we covered? [Skills development] Lesson 3 - What have been the biggest Cl...

Jan 21, 202649 min
Hosted on Buzzsprout
For the best experience, listen in Metacast app for iOS or Android