For years, I paid a freelancer to populate my underwriting spreadsheets: $100 per property and a wait of 3-4 days. At the time, I was happy to pay it; outsourcing the work freed up my time for higher-value tasks. The problem was the wait. You can't move on a deal until someone else finishes their part. Claude Cowork has automated this process entirely for me. For this month's newsletter, I'll walk you through how to train it to do the same for you.
Join 2,000 real estate investors as we dive deep into the world of multifamily investing. Subscribe to The Ridgeview Report
Before jumping in, take time to understand what you're working with. Claude Cowork is powerful because it can access and modify files directly on your computer, and that's also what makes it worth approaching carefully. I'd suggest starting with an introduction video like this one from YouTuber Jeff Su. A few setup steps are non-negotiable: require Claude to ask permission before modifying any file, give it access only to a dedicated folder, not your entire machine, and pay the $20/mo fee. for the Pro account.
The actual process is straightforward. Your underwriting spreadsheet has a set of input cells that need to be filled. Walk Claude through them one at a time, exactly as you would when training a new hire. For the property address, I instructed: "For cell C11, open the offering memorandum and find the listed property address. It is usually on the first four pages." It completes the action, I verify it, and we move on. For data not in the OM, Claude can search the internet. For the cell labeled Median Income, I instructed: "Search city-data.com for [city name] area median income of the subject property and input the figure." Give an instruction, check the result, and move to the next cell.
Translating the rent roll into a unit mix takes more work, but the key is to go carefully and slowly, one column at a time. Start by telling Claude to locate the rent roll file and upload it into the spreadsheet. Then give it this instruction: "Look at the rent roll and identify how many different unit layouts are present. List each one under Unit Type on the unit mix tab." Once that's populated and verified, move to the next column: Unit Count, then Average Square Footage, and so on until the table is complete.
The T12 follows the same approach. Tell Claude to locate the T12 file and upload it into the spreadsheet. Then instruct it: "Go through the T12 statement line by line and map each income and expense item to my standardized categories." Walk through your conventions explicitly. Late Fees map to Other Income. Snow Removal maps to Contract Services. Office Supplies map to General/Admin. For anything unclear, tell Claude to stop and check with you before mapping.
That first session took hours, but by the end, every component was working correctly. Worth noting: I have zero coding knowledge. The entire thing ran on verbal instructions, nothing more. When the session was complete, I asked Claude to save a "Skill" based on the conversation. This formally saves the workflow, so you don't need to repeat your instructions on the next deal. The following property, I dropped in the OM and rent roll, and Claude already knew the layout. It mapped the T12 without asking and flagged only the cells that needed my judgment. What had taken hours took 5 minutes.
It took half a day to train. In exchange, I eliminated a recurring cost, cut out a multi-day wait, and built something that gets better every time I use it. That's just underwriting. The same logic applies to any task in your business that follows a repeatable process. I'm still figuring out the edges of what's possible here, but I haven't been this excited about a new tool in a long time.
-Ben Michel
Ben Michel is the founder of Ridgeview Property Group, an investment firm specializing in multifamily real estate. Register Here to be notified of available investment opportunities.