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Matthew Rathbun would rather be building a cabin in the Virginia woods than sitting at a laptop, and that is exactly why his approach to Claude Cowork is worth copying. He oversees 300 agents at Coldwell Banker Elite and has rebuilt how his firm produces listing kits, training, and client emails around one downloadable app.
On this episode of AI Agent Advantage, JMan and Matthew break down Claude Cowork for real estate from the ground up: what it is, how to give it safe access to your files, and how projects and skills turn your repeat work into a one-word command.
What You'll Learn:
1: Why treating AI like an assistant you onboard beats treating it like a search box, and the exact starter prompt Matthew uses
2: What Claude Cowork actually is, how it differs from chat, and why it runs as a downloadable desktop app rather than a browser tab
3: How to set up a single controlled folder so Cowork only touches the files you choose, and how to revoke access in seconds
4: How feeding years of your own presentations and emails teaches the tool your voice and brand
5: How to build a Project for a repeatable workflow like buyer representation, including a 5 a.m. off-market listing search
6: How to create a Skill that turns a seven-prompt listing kit into a slash command that runs in four minutes
TIMESTAMPS:
00:00 Introduction and the cold open
01:00 The woods, the gadgets, and a lifelong fascination with thinking machines
05:00 Signing up for ChatGPT on day one and early industry skepticism
10:00 The onboarding mindset and why voice beats typing
13:00 Why Matthew added Claude, persistent memory, and trust
17:00 What Claude Cowork is and how it differs from chat
22:00 Setting up a controlled folder for safe file access
25:00 Why more context wins: presentations, emails, and class transcripts
32:00 Projects explained, including off-market listing searches
38:00 Skills, the listing kit slash command, and sharing a brand kit with your team47:00 Common mistakes, the intimidation barrier, and trusting the tool53:30 The single best AI tip and where to find MatthewAbout the Guest: Matthew Rathbun is Executive Vice President at Coldwell Banker Elite and a licensed broker across DC, Maryland, and Virginia, where he oversees roughly 300 agents. He is a multiple-time national Instructor of the Year and trains real estate professionals across the country on technology and practice. His AI tutorials and downloads live at matthewrathbun.com/ai.Connect with Matthew RathbunWebsite: https://www.matthewrathbun.comGuest LinkedIn: https://www.linkedin.com/in/matthewrathbun1Instagram: https://www.instagram.com/matthew_rathbun/FOUNDING SPONSORS: 1: Wise Agent | https://wiseagent.com/jsquared - The all-in-one CRM that helps real estate agents manage contacts, automate follow-up, and grow their business.2: Subi | https://www.oksubi.com/ - Your AI transaction genie. From contract to close, your work is my command.3: The CE Shop | https://j2.theceshop.com/ Use the discount code jsquared for an additional 35% offAbout the Show: AI Agent Advantage is the tactical AI podcast for real estate professionals. Hosted by JMan, every episode breaks down one expert, one tool, and one thing you can implement before your next client call. New episodes every Friday.Subscribe so you never miss an episode. Share this with one agent who is still figuring out AI — that is how we grow this.Read the full episode breakdown:
