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Recent episodes
Prove Your Value at Work in the AI Era: Judgment Artifacts
May 31, 2026
Unknown duration
How I AI: My Weekly Codex Experiments
May 30, 2026
Unknown duration
Product Management When Software Creation Is Cheap
May 29, 2026
Unknown duration
Agent Product Analytics: What Your Dashboard Can't See
May 28, 2026
Unknown duration
How to verify AI-generated Office files before they ship
May 27, 2026
Unknown duration
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 5/31/26 | ![]() Prove Your Value at Work in the AI Era: Judgment Artifacts | For deeper playbooks and analysis: https://natesnewsletter.substack.com/What's really happening when AI makes everyone's work look polished?The common story is that AI makes people more productive -- but the reality is that it also makes old evidence less trustworthy.In this episode, I share the inside scoop on how to prove you are good at work when outputs are easier to generate than ever.Why portfolios are no longer enough on their ownHow whiteboard-style conversations reveal judgmentWhat situation, decision, risk, and change show about real workWhere Talent Board-style evidence fits into careers and hiringHow to make your reasoning visible without over-performingIf you hire, manage, build, or are trying to grow into a new role, the shift matters: the scarce signal is no longer just what you produced. It is whether people can see how you understood the problem, handled tradeoffs, and improved the work.Subscribe for daily AI strategy and news.Hosted on Acast. See acast.com/privacy for more information. Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
| 5/30/26 | ![]() How I AI: My Weekly Codex Experiments | For deeper playbooks and analysis: https://natesnewsletter.substack.com/What's really happening when AI stops being a chat box and starts becoming a working context system?The common story is that better prompting is about clever wording — but the reality is that the work is moving toward cleaner context, better task shape, and agents that can stay oriented through long runs.In this video, I share the inside scoop on how I'm using AI this week: assembling context windows, using Codex on local files, and shifting from prompt engineering into collaborative task definition.Why local folders can become clean context windows How Codex changes long document, spreadsheet, and code workflows What changed in prompting after agentic workflows got better Where Claude still fits for polish, salience, and design Why multi-threaded drafting now feels practicalFor operators, builders, marketers, and executives, the important shift is not just which model wins. It's learning how to structure the work so the model can help you think, execute, review, and iterate.Subscribe for daily AI strategy and news.Hosted on Acast. See acast.com/privacy for more information. Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
| 5/29/26 | ![]() Product Management When Software Creation Is Cheap | For deeper playbooks and analysis: https://natesnewsletter.substack.com/Product management is changing as AI makes first versions cheaper. The obvious advice is that PMs should prototype more, but the deeper shift is about judgment: deciding what should exist, what should be deleted, who a product is for, what standard it needs to meet, and what the company is willing to rely on.Nate walks through the move from rationing scarce engineering to classifying software abundance, including the Prototype Commons, production class ladders, and why promotion and demotion become core product work.Hosted on Acast. See acast.com/privacy for more information. Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
| 5/28/26 | ![]() Agent Product Analytics: What Your Dashboard Can't See | For deeper playbooks and analysis: https://natesnewsletter.substack.com/What's really happening when your user is no longer just clicking, but delegating work to an agent?The common story is that agent failures are engineering incidents — but the reality is that many of them are product analytics failures hiding inside the agent run.In this episode, I share the inside scoop on why product teams need a new analytics layer for agent products.Why chat logs are not enoughHow agent runs replace sessions as the unit of behaviorWhat Salesforce's Agent Work Units signal about SaaS metricsWhere completion, acceptance, and correction rates fitWhy product analytics becomes the rudder for agent autonomyOperators, product leaders, and builders should care because agents move too fast for old dashboards. If you cannot see intent, tool calls, permissions, corrections, completion, and trust in one run-level view, you are steering with missing instruments.Subscribe for daily AI strategy and news.Hosted on Acast. See acast.com/privacy for more information. Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
| 5/27/26 | ![]() How to verify AI-generated Office files before they ship | For deeper playbooks and analysis: https://natesnewsletter.substack.com/AI can make PowerPoint decks, Excel workbooks, and Word documents faster, but faster is not the same as trustworthy. In this episode, Nate breaks down a practical workflow for AI Office files: prepare the sources, define the structure, constrain the artifact creation, and verify the output like a skeptical reviewer.The key idea: the file is not the whole thing. The file is the visible output of a knowledge-work system. If the claims, numbers, sources, assumptions, charts, and formulas cannot be traced, the artifact may look finished while quietly breaking trust.Hosted on Acast. See acast.com/privacy for more information. Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
| 5/26/26 | ![]() Public AI Work: How Teams Actually Learn From AI | For deeper playbooks and analysis: https://natesnewsletter.substack.com/What's really happening when AI work moves out of private chats and into shared company spaces?The common story is that AI adoption is mostly about buying better tools -- but the reality is that the companies learning fastest are making the work itself visible.In this episode, I share the inside scoop on how public AI workflows can become apprenticeship infrastructure for teams learning to work with agents.Why Slack is becoming a practical substrate for human-AI collaborationHow Shopify's River workflow makes agent work observableWhat most companies lose when AI work stays hidden in private windowsWhere senior operators should make non-sensitive AI work publicWhy constraints can turn AI use into shared learning instead of isolated productivityThis matters for operators, builders, executives, and team leads who need AI adoption to compound across the organization, not just live inside the habits of a few early adopters.Subscribe for daily AI strategy and news.Hosted on Acast. See acast.com/privacy for more information. Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
| 5/25/26 | ![]() AI Agents Create a Hidden Platform Team Bottleneck | What's really happening inside an AI infrastructure team when agents start doing the work? The common story is that AI makes every team faster. The reality is more complicated, because the speed arrives unevenly and someone underneath has to absorb it. I sat down with Emma, who leads data infrastructure engineering at OpenAI, to find out what her team is actually building to stay ahead of the agents.In this interview, I share the inside scoop on why platform teams become the bottleneck when AI agents scale across a company:- Why app teams and platform teams accelerate at completely different rates- How goal-directed agents start to feel adversarial without meaning to- What OpenAI's data platform team built to buy back time- Where a private eval suite fits into surviving constant model upgradesFor platform and infra engineers, this is the telegraph from the future: the pinch point is coming, and the teams that instrument the load now are the ones who stay standing.For deeper playbooks and analysis: https://natesnewsletter.substack.com/ Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
| 5/24/26 | ![]() Why Big Tech Now Runs an AI Factory | What's really happening inside the AI supply chain that powers every model you use?The common story is that AI is a software business with a fancy backend. The reality is more complicated, and it changes how you should buy, budget, and contract for AI.In this podcast, I share the inside scoop on why your AI vendor contract is now a supply contract in everything but name: • Why "capacity constrained" points to memory and packaging, not GPUs • How hyperscaler CapEx reshapes every vendor agreement you sign • What questions belong in your next AI investment review • Where a single supply chain delay stops you from shipping AIFor operators and CFOs, the takeaway is sober: cheaper tokens are real and serving costs keep falling, but the industrial base underneath your AI strategy still demands supply assurance, utilization discipline, and contracts that account for allocation risk.Subscribe for daily AI strategy and news.For deeper playbooks and analysis: https://natesnewsletter.substack.com/ Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
| 5/22/26 | ![]() AI Project Room: Organize Files Before Asking AI to Write | Now I have the full transcript. Building the deliverable.What's really happening when prestigious law firms file motions full of AI hallucinations?The common story is that better prompts prevent hallucinations — but the reality is more complicated.In this video, I share the inside scoop on the project room workflow that makes hallucinations structurally unlikely: • Why your first AI prompt should never be "do the thing" • How agents now walk folder trees and compare files cleanly • What artifacts make an agent's judgment visible and inspectable • Where most serious knowledge work breaks down before the draftOperators doing high-stakes knowledge work with AI agents need to shape the canvas before the writing starts, or they ship the same soft spots that landed Sullivan and Cromwell in front of a federal judge.Subscribe for daily AI strategy and news. For deeper playbooks and analysis: https://natesnewsletter.substack.com/ Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
| 5/21/26 | ![]() MIT Says Half Your AI Gains Come From How You Ask. Not the Model. | Now I have the full transcript. Building the deliverable.What's really happening inside prompting now that AI agents are 100x more powerful than six months ago? The common story is that prompt engineering is dead — but the reality is more complicated.In this podcast, I share the inside scoop on the AI Question Method and why heavy knowledge work with frontier models demands a new mental model:• Why prompt engineering is now table stakes, not a skill • How to treat AI like a senior partner, not a junior • What three question principles unlock agentic knowledge work • Where most users still prompt like it is 2025For operators and builders, the agentic shift is a real opportunity, but only if you evolve your prompting alongside the models and learn to ask sharper questions instead of issuing tasks.Subscribe for daily AI strategy and news. For deeper playbooks and analysis: https://natesnewsletter.substack.com/ Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
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| 5/20/26 | ![]() I Asked Seven Questions About Our AI Agent. We Failed Five. | What's really happening inside the AI agent stack as agents move into production? The common story is that OpenAI and Anthropic decide whether your agent ships — but the reality is more complicated.In this podcast, I share the inside scoop on the infrastructure companies quietly deciding whether AI agents reach production:Why runtime, identity, and data are the real control layersHow Cloudflare, Auth0, and Snowflake gate agent deploymentWhat separates a kill switch from telling the model to stopWhere Stripe and the card networks are racing on paymentsFor builders and operators, the agentic shift is a real opportunity, but only if you map runtime, identity, data, payments, and observability for each workflow before it ships, not after.Subscribe for daily AI strategy and news. For deeper playbooks and analysis: https://natesnewsletter.substack.com/ Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
| 5/19/26 | ![]() Six protocols emerged. Three decide which agents survive. | What's really happening inside the agent protocol stack as Google I/O kicks off? The common story is that every new protocol is a must-have standard — but the reality is more complicated.In this postcast, I share the inside scoop on the six agent protocols shaping how AI agents actually ship and how customers experience them:Why three protocols are becoming the real agent stackHow MCP, A2A, and AGUI map to core agent jobsWhat separates a standard from a contested protocolWhere payment protocols collide with customer trustFor builders and operators, the agentic substrate is a real lever on customer experience, but only if you stop chasing acronyms and start asking which protocols actually shape the workflow you're shipping.Subscribe for daily AI strategy and news. For deeper playbooks and analysis: https://natesnewsletter.substack.com/ Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
| 5/18/26 | ![]() Marketing for Humans and AI Agents in 2026 | What's really happening inside the AI-driven shift in marketing?The common story is that AI makes marketing faster — but the reality is that the entire internet economy is moving from attention to interpretation, and most marketers are still optimizing for the wrong one.In this video, I share the inside scoop on the two-internet economy and what it means for marketers and individuals: - Why AI agents now sit between buyers and brands in B2B and consumer - How a truth layer wins where emotional marketing copy fails with LLMs - What AI-washing costs companies and candidates trying to look AI-native - Where marketing has to touch — website, pricing, docs — to stay relevantThe marketers and candidates who win in 2026 will be the ones who build memory in humans and clarity for agents, not the ones automating the back office faster.Subscribe for daily AI strategy and news.For deeper playbooks and analysis: https://natesnewsletter.substack.com/ Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
| 5/17/26 | ![]() AI Build Buy Hire Wait Decision Matrix for Teams | What's really happening inside AI investment decisions at most companies? The common story is that you need an AI strategy — but the reality is more complicated.In this video, I share the inside scoop on how to allocate capital across build, buy, hire, and wait for AI agents and workflows:Why workflow shape, not AI strategy, drives investmentHow to pick between automate, build, buy, hire, waitWhat separates a real AI hire from a unicornWhere most agentic AI projects quietly failFor operators and executives, the agentic era opens unprecedented upside, but only if you stop chasing a singular AI strategy and start making disciplined capital allocation decisions one workflow at a time.For deeper playbooks and analysis: https://natesnewsletter.substack.com/ Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
| 5/16/26 | ![]() Claude Recovered $400K in Bitcoin. That's Not Even the Big Story. | What's really happening inside the AI agent ecosystem this week? The common story is that the model launches are the main event — but the reality is more complicated.In this video, I share the inside scoop on five AI agent stories reshaping how real work gets done:How Notion turned its workspace into an agent platformWhy Claude usage limits are breaking the subscription modelWhat Anthropic passing OpenAI on business customers signalsWhere Mythos and GPT 5.5 push AI cybersecurity nextFor operators and builders, the agent era is opening real workflow leverage, but it also forces hard choices on pricing, security posture, and which AI stack to commit to.Subscribe for daily AI strategy and news.For deeper playbooks and analysis: https://natesnewsletter.substack.com/Listen to this video as a podcast. Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
| 5/15/26 | ![]() SaaS Agent Licensing: What Your 2026 Renewal Will Look Like | What's really happening inside SaaS pricing as AI agents take over the work? The common story is that agents will just replace seats — but the reality is more complicated.In this video, I share the inside scoop on how the agent era is rewriting SaaS economics and what to negotiate before your next renewal: • Why seat-based pricing is breaking under AI agents • How Salesforce, Microsoft, and ServiceNow meter agentic work • What separates a fair agent license from rent-seeking pricing • Where SAP-style API policies could lock out your agentsFor operators and builders, the agentic shift is a real opportunity, but only if you negotiate the meter, the caps, and the access path before usage gets embedded and your leverage disappears.Chapters:00:00 Agentforce hits $800M run rate00:55 Four questions before your next renewal01:45 Why the seat model is breaking02:50 Salesforce Flex Credits and work units03:40 Microsoft Copilot credits and hybrid pricing04:45 The 8 billion token developer story05:30 ServiceNow Action Fabric and operational metering06:30 SAP 2026 API policy and agent lock-out07:45 Pricing follows platform control08:40 Fair license versus rent-seeking patterns10:00 What builders must know about cost structure11:30 Negotiating agent access before usage embeds13:00 The commercial unit of software is changingSubscribe for daily AI strategy and news.For deeper playbooks and analysis: https://natesnewsletter.substack.com/ Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
| 5/14/26 | ![]() The Enterprise AI Deployment Layer: Why Model Access Isn't Enough | What's really happening inside the AI agent implementation war?The common story is that the AI agent battle is between OpenAI and Anthropic on raw model quality — but the reality is that private equity, hyperscalers, consultancies, and systems of record are all converging on the implementation layer where trillions of dollars actually live.In this video, I share the inside scoop on why generic enterprise AI is getting squeezed from four directions at once: • Why frontier labs are moving down the stack into deployment • How private equity became a distribution channel for AI agents • What the implementation layer actually contains for AI agents • Where the real defensibility lives in agentic workflowsBuilders, buyers, and PE all need to get specific about workflow design, data access, authority, evals, and audit trails — generic AI wrappers will not survive the squeeze that is now hitting enterprise agentic workflows.Subscribe for daily AI strategy and news.For deeper playbooks and analysis: https://natesnewsletter.substack.com/Listen to this video as a podcast.- Spotify: https://open.spotify.com/show/0gkFdjd1wptEKJKLu9LbZ4- Apple Podcasts: https://podcasts.apple.com/us/podcast/ai-news-strategy-daily-with-nate-b-jones/id1877109372 Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
| 5/13/26 | ![]() RAG for AI Agents: Knowledge Layer Architecture Guide | What's really happening inside the AI agent memory infrastructure war?The common story is that bigger context windows and better vector search will solve it — but the reality is every serious infrastructure vendor is racing to fix a deeper problem that classic RAG can't touch.In this video, I share the inside scoop on why memory is now the real battleground for production AI agents: • Why classic RAG was built for chatbots, not agents • How Pinecone, PageIndex, SAP, and GraphRAG attack different shapes • What a retrieval contract actually looks like for AI agents • Where most agent builds quietly waste their token budgetBuilders who write down what their agent needs before picking a database will ship reliable systems — the ones who shop vendor-first will keep paying for rediscovery on every run.Subscribe for daily AI strategy and news.For deeper playbooks and analysis: https://natesnewsletter.substack.com/ Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
| 5/12/26 | ![]() Agentic Commerce Is A Protocol War. Here's Who's Fighting. | What's really happening inside the agentic commerce protocol war?The common story is that AI agents will just plug into existing checkout — but the reality is that six camps are fighting over who carries the responsibility when an agent spends your money.In this video, I share the inside scoop on the six layers where AI agents, merchants, and payment networks are battling for control: • Why ACP and UCP answer completely different merchant questions • How AP2 and Stripe authorization create the agent permission layer • What stablecoins and x402 unlock for machine-to-machine payments • Where AWS Bedrock Agent Core fits as the governance runtimeAgentic commerce is the biggest internet economy shift since the 1990s — operators who understand the layers will shape it, and those who don't will get sidelined by it.Subscribe for daily AI strategy and news.For deeper playbooks and analysis: https://natesnewsletter.substack.com/ Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
| 5/11/26 | ![]() Your AI Agent Doesn't Need A Better Prompt. It Needs A Judge. | What's really happening when AI agents take real actions in production, and why do better prompts keep failing to stop them?The common story is that prompt engineering and human approval will keep AI agents safe — but the reality is that frontier-model agents now need their own manager: a separate LLM-as-judge that guards your intent at the action boundary.In this video, I share the inside scoop on the architectural pattern that's quietly replacing prompt-based guardrails in serious agentic systems: • Why prompts and manual approval both break under real agent workloads • How Lindy redesigned its system after agents started sending unauthorized emails • What the four action-risk classes mean for read, write, and high-stakes calls • Where correlated judgment fails and frontier models change the calculusBuilders shipping agents without a judge layer are gambling on every tool call — the teams who classify actions, instrument a four-way decision scope, and put a frontier model in the judge seat are the ones whose agents will actually be trusted to do real work.Subscribe for daily AI strategy and news.For deeper playbooks and analysis: https://natesnewsletter.substack.com/ Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
| 5/10/26 | ![]() Enterprise AI Buying Process: Why Roadmaps Fail in the Build Room | What's really happening with AI agent security — and what does it mean for your AI roadmap?The common story is that McKinsey's Lilly platform had a security lapse — but the reality is a procurement and organizational design failure that most companies are quietly repeating right now.In this video, I share the inside scoop on why AI agent exploits are a strategy problem, not a tech hygiene problem: • Why 22 unauthenticated endpoints signal culture, not carelessness • How traditional SaaS procurement breaks down with AI agents • What every vendor announced this week and why it matters • Where to start if your AI stack can't distinguish humans from agentsIf your team is buying or building AI software this quarter, the cheapest move is bringing your developers to the table before you sign — not after.Subscribe for daily AI strategy and news.For deeper playbooks and analysis: https://natesnewsletter.substack.com/ Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
| 5/9/26 | ![]() Codex Plugins: Why the AI Bottleneck Moved to Workflow | What's really happening with codex plugins, skills, prompts, and MCPs as agents start doing real work? The common story is that plugins are just app store add-ons — but the reality is more complicated.In this video, I share the inside scoop on the agentic scaffolding that actually makes AI useful: • Why prompts work for one-offs but break under repeated workflows • How skills encode your house style across any LLM you use • What plugins package up and why they're bigger than MCPs • Where hooks, scripts, and connectors fit inside the larger systemFor operators and builders, the leverage in 2026 lives in knowing which part of your workflow belongs in a prompt, a skill, a plugin, or an MCP — and packaging the right ones so your team can actually reuse them.Subscribe for daily AI strategy and news.For deeper playbooks and analysis: https://natesnewsletter.substack.com/ Hosted on Acast. See acast.com/privacy for more information. | — | ||||||
| 5/8/26 | ![]() 271 Vulnerabilities: What Mozilla's AI Found Changes Everything✨ | software securityAI in code review+4 | — | MythosFirefox+2 | — | software vulnerabilitiesAI code review+6 | — | 30m 40s | |
| 5/7/26 | ![]() Your AI Agent Is Locked To One Model. OpenClaw Just Killed That.✨ | AI agentsruntime abstraction+4 | — | CodexOpenBrain+3 | — | OpenClawAI agents+6 | — | 25m 46s | |
| 5/6/26 | ![]() Your AI Fails At Real Work. The Model Isn't Why.✨ | AI strategysemantic work primitives+4 | — | SalesforceSAP+1 | — | AIagents+6 | — | 23m 16s | |
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