Tuesdays are 3 AI updates, one hot take, one action. Weekends are 1 practical real estate agent workflow.
On Tuesday I said your sphere lives in Messages. But it’s pretty intimidating to think about going back through all your past iMessages. OOF. Well your AI assistant is here to help.
What you'll have when you're done: a list of people who told you something real in the last year, a baby, a move, a renovation, a new job, and the chance to reconnect.
Step 1. Pick your tool (5 min)
ChatGPT is the faster setup. Open the desktop app on an Apple silicon Mac, go to Plugins, install Apple Messages. It runs inside ChatGPT Work and Codex rather than a regular chat, which is where most people get stuck looking for it.
Claude's version is at claude.com/plugins/imessage and works best in Claude Code (not ideal for agents). It reads your messages locally and never sends them to an outside server, and you can allowlist which contacts are able to reach it.
It’s not the only way. After Tuesday’s email a great agent emailed me and said they were using a combination of Base44 and Whatsapp. Regardless of who you use, everyone will want Full Disk Access on your Mac. Your phone is full of client conversations, so decide how you feel about that before you start.
Step 2. Mine a year of texts (2 min)
After you get the integration setup, paste this:
Search my messages from the last 12 months. Find every conversation where the other person mentioned a life event: a baby, an engagement or wedding, a new job, a move, a renovation, a kid starting school, a death in the family. For each one give me their name, the date, one line on what they said, and how long it's been since we last talked. Sort by how long it's been. Don't draft anything.
Step 3. Read the list (5 min)
You'll get ten to thirty names. Cross off anyone you already handled properly. What's left is your week. A few of them will hurt. Someone told you something that mattered to them while you were mid-showing, and it moved up the screen before you got back to it.
Step 4. Write them yourself (10 min)
Don't let AI send these. Use it to remember what was said, then type the message with your thumbs. Two sentences. Name the specific thing, ask one question, and leave out anything that sounds like "let me know if you ever need anything real estate."
"Hey Dana, I never properly said congrats on the new place in Sylvan Park. How's the kitchen holding up?"
If they want to talk about a house they'll bring it up. Don’t be surprised if it goes wrong initially. The first search may come back messy and pull in group threads. Tell it to skip those and run it again. Keep tinkering until you can send the message above. This is critical work to unlock a lot of sphere value.
BOSTON. ONE DAY. IN PERSON.
Thursday, September 24 I'm running a one-day Claude workshop in Boston. I’ll run through this exact setup in the room together, on your own phone and your own database, plus the rest of the system built live on your listings. It’s gonna be a small-ish room on purpose. Only $499. Grab your seat here.
Reply to this email with an example of how AI has transformed your day to day work, and I’ll send you an early bird code for 10% off.
-Matt
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