Microsoft Cloud IT Pro Podcast

Welcome to Episode 429 of the Microsoft Cloud IT Pro Podcast. In this episode, Scott and Ben dig into the concept of LLM wikis, specifically building personal knowledge management vaults using Obsidian, markdown, and AI tooling like Claude Code, GitHub Copilot CLI, and Copilot Cowork. The core idea comes from a gist by Andrej Karpathy and involves creating a structured folder of markdown clippings that an LLM can reason over to extract entities, concepts, and sources, building a searchable, graph-linked knowledge base over time. Scott walks through how he wired up Obsidian Web Clipper and an RSS Dashboard plugin to feed articles into his vault automatically, then had the LLM help build a Python script to automate the ingest workflow and cut down on token usage.

The conversation expands into how Copilot Cowork fits into this workflow as a scheduling harness, with practical examples of using it to pull email from an inbox daily, convert messages to markdown, and generate a prioritized to-do list. Ben shares how he applied the same approach to 428 episodes of podcast transcripts, and both hosts note that token costs can run high fast without some upfront thinking about optimization. Scott closes with a reminder that pulling data into plain markdown sidecars outside of IRM and sensitivity label protections means teams should stay mindful of organizational data policies.

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Show Notes

LLM Wiki

GitHub Copilot Wiki: An AI-Powered Second Brain Template

Karpathy’s LLM Knowledge Base Wiki for Enterprise

Karpathy’s LLM Wiki? No Code with Claude or Github Copilot!

sametbrr/llm-wiki-manager

Sponsors

TrustedTech is a leading Microsoft Cloud Solution Provider (CSP) specializing in Microsoft Cloud services, Microsoft perpetual licensing, and Microsoft Support Services for medium and enterprise-sized businesses. Their robust team of in-house, U.S.-based Microsoft architects and engineers are certified in all 6/6 Microsoft Solutions Partner Designations in the Microsoft Cloud Partner Program.

M365 Licensing Consultation

M365 Tenant Assessment

Copilot Readiness Assessment

ShareGate is your migration and governance solution for Microsoft 365. ShareGate helps your teams simplify tenant migrations, get Copilot-ready, and take control of Microsoft 365 governance.

Nasuni is a leading unstructured data platform for enterprises where file data is mission-critical for both people and AI. Nasuni powers the operational file layer where work happens — helping organizations manage, protect, and activate data so teams can work smarter, reduce costs, and operate securely without limits.

Intelligink — Would you like to become the irreplaceable Microsoft 365 resource for your organization? Let us know!

Welcome to Episode 428 of the Microsoft Cloud IT Pro Podcast. In this episode, Ben and Scott unlock the secrets to modernizing your IT management by ditching pesky on-prem GPOs and embracing the future with Intune. They discuss how savvy IT pros are migrating thousands of GPOs into clean, manageable cloud policies. Dive into real-world workflows: from exporting and analyzing legacy GPOs with AI tools, to recreating policies in Entra ID, and finally decommissioning AD. You’ll discover how to think through the migration, avoid common pitfalls like leftover legacy configs, and implement a phased migration that minimizes disruption.

Your support makes this show possible! Please consider becoming a premium member for access to live shows and more. Check out our membership options.

Show Notes

DiskPrices.com

These HDD prices are getting crazy. An increase of 96.4% in 1 month for the same 26TB drive. $279.99 a month ago to $549.99 today. Where are we buying hard drives now?

Import and analyze your on-premises GPOs using Group Policy analytics in Microsoft Intune

Microsoft Copilot in Intune

Policy CSP

Use the Intune settings catalog to configure settings

Use the Intune properties catalog to get device hardware properties

Create a Settings Catalog policy using your imported GPOs in Microsoft Intune

Sponsors

 

ShareGate is your migration and governance solution for Microsoft 365. ShareGate helps your teams simplify tenant migrations, get Copilot-ready, and take control of Microsoft 365 governance.

Nasuni is a leading unstructured data platform for enterprises where file data is mission-critical for both people and AI. Nasuni powers the operational file layer where work happens — helping organizations manage, protect, and activate data so teams can work smarter, reduce costs, and operate securely without limits.

TrustedTech is a leading Microsoft Cloud Solution Provider (CSP) specializing in Microsoft Cloud services, Microsoft perpetual licensing, and Microsoft Support Services for medium and enterprise-sized businesses. Their robust team of in-house, U.S.-based Microsoft architects and engineers are certified in all 6/6 Microsoft Solutions Partner Designations in the Microsoft Cloud Partner Program.

M365 Licensing Consultation

M365 Tenant Assessment

Copilot Readiness Assessment

 Intelligink — Would you like to become the irreplaceable Microsoft 365 resource for your organization? Let us know!

Welcome to Episode 427 of the Microsoft Cloud IT Pro Podcast. In this episode, Ben and Scott open with a quick look at YAKO (getyako.com), a browser extension built by community member Merrill that replaces the new tab page with a customizable dashboard of Microsoft 365 and cloud links. From there, the conversation turns into an extended follow-up on Copilot Cowork, covering some of their recent hands-on experience with custom skills, artifact management, session crashes tied to an Anthropic API outage, and the friction of working with IRM-protected documents in Copilot Cowork.

The bigger thread running through the episode is data security. Listen in to hear more about considerations for onboarding to Copilot Cowork in its early days.

Your support makes this show possible! Please consider becoming a premium member for access to live shows and more. Check out our membership options.

Show Notes

Yako

Get started with Cowork (Frontier)

How does Cowork handle my data?

Does Cowork connect to external models for processing?

Are there unsupported countries/regions?

Sensitivity labels for Microsoft 365 Copilot and Microsoft 365 Copilot Chat

Sponsors

TrustedTech Team is a leading Microsoft Cloud Solution Provider (CSP) specializing in Microsoft Cloud services, Microsoft perpetual licensing, and Microsoft Support Services for medium and enterprise-sized businesses. Their robust team of in-house, U.S.-based Microsoft architects and engineers are certified in all 6/6 Microsoft Solutions Partner Designations in the Microsoft Cloud Partner Program.

M365 Licensing Consultation

M365 Tenant Assessment

Copilot Readiness Assessment

ShareGate is your migration and governance solution for Microsoft 365. ShareGate helps your teams simplify tenant migrations, get Copilot-ready, and take control of Microsoft 365 governance.

Nasuni is a leading unstructured data platform for enterprises where file data is mission-critical for both people and AI. Nasuni powers the operational file layer where work happens — helping organizations manage, protect, and activate data so teams can work smarter, reduce costs, and operate securely without limits.

Intelligink — Would you like to become the irreplaceable Microsoft 365 resource for your organization? Let us know!

Welcome to Episode 426 of the Microsoft Cloud IT Pro Podcast.Ben and Scott are back together this week to talk through Microsoft 365 Copilot Cowork, including how it compares to Claude Cowork and where each one makes sense. The two products share a name but work pretty differently. Claude Cowork runs locally on your desktop and can access files on your machine, supports MCP server connections while M365 Copilot Cowork runs in the cloud, requires files to be in OneDrive, and does not support MCP connectors yet. On the flip side, the Microsoft version runs scheduled tasks without needing your machine to be on, has native access to all your M365 data through Graph, and fits inside your existing compliance and security controls through Purview, which matters a lot for regulated organizations.

Your support makes this show possible! Please consider becoming a premium member for access to live shows and more. Check out our membership options.

Show Notes

Quentin Amaudry – As everyone knows, Cowork is coming within Copilot and it is extremely promising

Copilot Cowork vs Claude Cowork: Same AI, Different Worlds

Copilot Cowork: A new way of getting work done

Cowork overview (Frontier)

About the sponsors

 

TrustedTech is a leading Microsoft Cloud Solution Provider (CSP) specializing in Microsoft Cloud services, Microsoft perpetual licensing, and Microsoft Support Services for medium and enterprise-sized businesses. Our robust team of in-house, U.S-based Microsoft architects and engineers are certified in all 6/6 Microsoft Solutions Partner Designations in the Microsoft Cloud Partner Program.

M365 Licensing Consultation

M365 Tenant Assessment

Copilot Readiness Assessment

Your migration and governance solution for Microsoft 365. ShareGate helps your teams simplify tenant migrations, get Copilot-ready, and take control of Microsoft 365 governance.

Nasuni is a leading unstructured data platform for enterprises where file data is mission-critical for both people and AI. We power the operational file layer where work happens — helping organizations manage, protect, and activate data so teams can work smarter, reduce costs, and operate securely without limits. Visit nasuni.com to learn more.

Would you like to become the irreplaceable Microsoft 365 resource for your organization? Let us know!

Welcome to Episode 425 of the Microsoft Cloud IT Pro Podcast. In this audio and video episode recorded live at Microsoft headquarters during the MVP Summit, Ben welcomes a return guest, Joy Apple, to the Microsoft Cloud IT Pro Podcast and discuss her 20-year career in the Microsoft collaboration space, from financial services to SharePoint training, consulting, and her current role at Orchestry Software. Joy explains Orchestry as a Microsoft 365 governance automation layer covering templated provisioning for SharePoint and Teams, archiving policies (including Microsoft 365 Archive), guest management, and OneDrive governance. They emphasize that AI and Copilot amplify existing information architecture, permissions, and data hygiene issues, making governance more critical. They describe the MVP Summit as a “family reunion” where MVPs attend sessions and reconnect with peers. Joy and Ben also spend some time describing paths becoming an MVP and how much they just enjoy the community around the Microsoft 365 ecosystem and connecting with people both at MVP Summit as well as various conferences throughout the year.

About Joy Apple

Joy is a Microsoft MVP and Director of Success and Enablement at Orchestry. With years of experience as an information technologist, I’m dedicated to helping organizations implement technology with a purpose-driven, “human-first” approach, ensuring tools like Microsoft 365 empower people to do their best work.

Teaching and knowledge-sharing are at the heart of what I do. Whether it’s through volunteering in the Microsoft Community, speaking at events, or writing as the “Joy of SharePoint,” I’m passionate about helping others unlock their potential with modern workplace solutions.

Im also a cohost of the Guardians of M365 Governance podcast, where I explore the challenges and rewards of governance, and a columnist for She is Tulsa, a quarterly magazine celebrating impactful stories from my local community.

Outside of work, you’ll often find me enjoying live music or discovering new spots in Tulsa, Oklahoma, combining my love of connection and creativity wherever I go.

Show Notes

See the recording from the Microsoft Studios!

Joy Apple on LinkedIn

The Microsoft 365 Maturity Model – Governance, Risk, and Compliance Competency

The Microsoft MVP Communities

About the MVP Program

Overview of Microsoft 365 Archive

Guests in the Microsoft 365 admin center

Mitigate Oversharing to Govern Microsoft 365 Copilot and Agents

Orchestry

About the sponsors

 

TrustedTech is a leading Microsoft Cloud Solution Provider (CSP) specializing in Microsoft Cloud services, Microsoft perpetual licensing, and Microsoft Support Services for medium and enterprise-sized businesses. Our robust team of in-house, U.S-based Microsoft architects and engineers are certified in all 6/6 Microsoft Solutions Partner Designations in the Microsoft Cloud Partner Program.

M365 Licensing Consultation

M365 Tenant Assessment

Copilot Readiness Assessment

Your migration and governance solution for Microsoft 365

ShareGate helps your teams simplify tenant migrations, get Copilot-ready, and take control of Microsoft 365 governance.

Our Microsoft 365 experts and Microsoft Azure experts focus on the Microsoft cloud, so you can focus on what you do best! Learn more how we can help you!