Human in the Loop: Two Ex-Microsoft Builders on AI

You have wanted to try Linux for years, and you quit in the same place every time: the install, the hotkeys, and all the ways to break the thing before you have done anything with it. After 20 years deep in Windows internals and three on a Mac, Sash hit exactly that wall, then installed Omarchy, DHH's Arch and Hyprland desktop, on a dusty Lenovo ThinkCentre off the SD card in his Sony a6000, because no USB stick in the house held s...

Your shipping carrier sends a bill. Your invoicing system sends invoices. Nobody has ever compared the two, because the systems were never connected and the reconciliation was a spreadsheet import somebody did by hand. Drummond's CIO pointed an MCP at both sides, extrapolated a year out, and found more than $600,000 in shipping charges the company had absorbed and never passed on to its clients. The same tooling caught carrier over...

Picture your company a year from now with two dozen agents running in it. One of them starts returning a number that is quietly wrong. Nobody is named as its owner, nothing recorded which data it touched, and the model underneath it changed three weeks ago without anyone noticing. No better model fixes that, because the model was never the problem.

That is the gap between two numbers from the same BCG read: 82% of CEOs are more opti...

Chris has spent months trying to get his agents to talk to each other, and this episode is the honest tour of three attempts: what broke, what held, and what he actually runs now. He frames it against four trust levers borrowed from how a person climbs through the ranks - human IS the loop, human IN the loop, human ON the loop, human OUT of the loop - and pins the current shift to Gary Vaynerchuk's 15/80/5 model: own the first 15 p...

Eric Brown, a Solution Engineer at Microsoft focused on Copilot and agents, joined Chris and Sash to walk through Copilot Cowork the way he demos it for enterprise customers. The framing up front: the bottleneck in most organizations was never a lack of knowledge, it is coordination across email, meetings, chat, and scattered documents - and Cowork is built to act as an agentic teammate inside that mess rather than another place to...

Sash drives this one, and he does not start with the tool. He starts with the failure. He was running Claude Code across two Macs, so his first move was the obvious one: put his intelligence folder of Markdown context files in a git repo and sync it to both machines. That worked until it did not. Every session ended with a push he had to remember, and every session started with a pull he had to remember, and forgetting either one m...

Kevin Johnson - KJ - leads the AI and automation practice at Pinnacle Financial Partners, a bank that closed a merger of equals in January between two institutions north of $60 billion each. He has been doing this hand-to-hand since ChatGPT launched in November 2022. Chris and Sash brought him on to answer the question every enterprise team is quietly stuck on: what actually has to be true before generative AI works in production.

H...

Anthropic started watermarking every piece of text Claude produces, worldwide, three days before this episode and Sash and Chris jumped on an unplanned morning show to work through what it actually does. The watermark has two parts: an invisible mark woven into the text itself, and C2PA metadata (the same provenance standard Microsoft and Google use) attached to generated artifacts like images and documents. It is not opt-in - Anth...

Rene Charbonneau returns three months after EP.009 to report on the promise he made on his way out the door: refactor his AgentOS. He didn't refactor it. He blew it up. What started as a two-week attempt to untangle a ball of yarn he and Claude had built together turned into a full rebuild once he realized the old assumptions (a single hand-built harness, a builder-first workflow, memory scattered across machines) no longer held. T...

Chris opened the show with roughly thirty seconds of himself that was not himself. The voice, the face, and the script were all generated, and the reveal was the point: the pipeline that produced that cold open is the same one that produces the trailer, the highlight reel, and the product demos. He then kicked off two real jobs live on stream, the EP.020 trailer and an iLink product demo, and let them run in the background while he...

Sash drove this one, and the framing he opened with does most of the work: a model is a faucet of intelligence, but a faucet on its own does not plumb a house. An agent is a model plus a harness, and the harness is the environment the model actually runs inside. It is the app. The chat window is a harness. Claude Code is a harness. Hermes and OpenClaw are harnesses. What the harness supplies is everything the model cannot supply it...

Chris drove this one solo-demo style, no guest, closing out the AI-for-enterprise arc for now to make room for other topics. He walked through TheGrove, his personal agent system, and specifically the Follow-up Engine: an agent that reads meeting notes and call transcripts and drafts the follow-up email in his own voice. The demo used a sanitized mock transcript (a made-up company, "Harborline Financial") - the agent identified att...

This is episode four of the AI for Enterprise series and the most practical one yet. Sash walks through what Claude skills actually are - a folder with a skill.md file written in plain English, plus any reference files, templates, or scripts the workflow needs. The standard was released by Anthropic in November 2025, and within two months 16 other vendors adopted it, including Microsoft (it shows up as skill.md in M365 Copilot Agen...

Chris and Sash spend this episode working through a problem most enterprise leaders already know exists but haven't acted on: employees running AI tools the company never approved. They define Shadow AI plainly - using a model or AI system your company hasn't sanctioned to do work - and draw a direct line from the old Shadow IT problem (pulling data into a personal Dropbox) to the new one (uploading confidential documents to a pers...

This is the re-record of episode two of the AI for Enterprise series - the first take went out with Sash's audio muted, so Chris and Sash ran it back. The topic is the one landing in every CFO and CTO inbox right now: why AI token budgets are blowing up and what to actually do about it. The catalyst is real - Uber gave engineers $1,500 a month of API budget and the whole company burned its entire year's allocation in four months. T...

Chris opens this episode - the first of a four-part AI for Enterprise series - with a challenge to the room: Responsible AI is the part of every AI presentation where people pull out their phones. Not anymore. The regulatory environment has shifted, and a $35 million EU AI Act fine has a way of making even the most skeptical CIO lean forward. Chris draws directly from his time at Microsoft, where he presented the company's OpenAI p...

Sash drives this one, screen-sharing the always-on AI agent he runs in the cloud and showing how Claude Code became the tool that keeps it alive. His agent (Blaze) runs on a standard OpenClaw image inside a Hostinger Linux VPS, controlled over Telegram, and reachable only across a private Tailscale network so no one outside his own devices can touch it. The kicker: Sash had never used Linux. He never SSH'd into the box by hand or h...

We called an audible. Fable 5 - Anthropic's first Mythos-class model the public can actually touch - dropped this week, so the planned episode went out the window. Sash drove. Instead of a launch-day reaction, he showed two days of real work: he handed Fable 5 a job he'd been deferring for weeks, a full 31-lesson curriculum review spread across roughly 40 markdown files, with instructions to reformat lesson timing, reconcile contra...

Chris drives EP.10, a direct sequel to last week's monitoring episode with Rene. He opens with a failure: he added a feature to his Life OS (TheGrove), it tested green, and three days later every automation had stopped. The one that stung was the 8am morning-journal prompt - the first automation he ever built and the thing the rest of the system sits on top of. The trigger was tiny: a change that moved a single file. Claude ran 671...