Hi Reader

Every December, Spotify sends you a report about yourself. Nobody there wrote yours. Nobody picked your top artist, or decided to mention that you played the same sad song ninety-four times in March.

Plenty of those reports are going to look skewed this year with Dolly Parton showing up more frequently. Mine will. Nobody at Spotify decided that either. A lot of us went back to her catalog this week, so the data moved, and the report will move with it.

It is the most automated thing in your inbox all year, and it feels like the most personal thing in it.

Two weeks ago Susan Thetford in Nashville hit reply on the dentist issue and asked the question I should have answered inside it: great, but how do you actually automate the Month 2 and quarterly touches?

Fair. I handed you a map and skipped the wiring.

So here's what I've learned building these. Most people try to automate the message, and that's exactly why the later touches break. You write a good Month 2 email, drop it in a drip, and it goes out on schedule forever. Except it says the same thing in month two of 2026 that it said in month two of 2024. A static message on a long timeline doesn't age well. It ages badly, and in public.

Wrapped works the other way around. The message is just a shell. The payload regenerates. Same automation, brand-new content every time it fires, because it's built from data that keeps moving on its own.

Your later touches need that. Automate the trigger, then let a live payload fill it in.

And for us the payload is already sitting there. What their home is worth this month. What sold on their street. Which new listing matches the thing they told you they wanted back in March. All of it changes on its own, and none of it needs you to write a word.

That's the split most tech stacks get wrong. Your CRM is very good at remembering and it generates nothing, so pair it with something that does. (Plenty of platforms will regenerate those three. RealScout does all of them, and it's been writing the listing alerts to read naturally for years, which spares you a few hundred listing blurbs a year.)

The Three-Layer Wire-Up. Build each later touch in this order. Works in whatever you already use.

• Layer 1: the trigger. It lives inside the system, set the moment the contact is created. Month 2, then every quarter after, forever. If setting it depends on you remembering, you already know how that ends.
• Layer 2: the payload. The one thing in the email that's different every time it sends: home value, neighborhood activity, or a matching listing. Pick one per touch. Not all three.
• Layer 3: your voice, in one place only. Here's the part nobody tells you: you don't need to write all of these. A listing alert and market report don't need a note from you. The data is the star. The home value alert is more personal and taking the time to set a standing line on it in your own words, once, goes far to personalize the touchpoint. "I keep an eye on your street. Anything moves, you'll hear it from me first."

And this is the part I'd protect. If wiring this up means a dozen emails a week sitting in a queue waiting for your approval, you've just rebuilt the thing that broke your follow-up in the first place. Nobody wrote your Spotify Wrapped in December, remember. The words were already sitting there. The data did the rest.

Pick one contact you're currently sending nothing to. Build their Month 2 touchpoint. Twenty minutes for the first one, because you're figuring it out. Then clone it. Once it’s set up, your time investment in the process gets shorter and shorter.

Susan, thank you for telling me where the map stopped instead of quietly filing the email away, because that's the actual deal here: you tell me where it stops and I go build the rest.

So keep going. Reply and tell me what you're stuck on this week. I read every one.

Have a great weekend!

Alice

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