The List Of People Who Already Paid You And Then Disappeared

Here's the thing though. You spend money and energy chasing strangers who've never heard of you, while sitting on a list of people who already gave you money, already liked the work, and just… drifted. Life happened. They moved. They forgot your name. Somebody else was in front of them at the right moment.

That list is the cheapest revenue you will ever touch and almost nobody works it, because it feels weird to text somebody from 14 months ago out of nowhere.

It's not weird. You're not selling them anything. You're a person they know, checking in, with something useful. Do it once a quarter and it pays.

What you need

• Wherever your customer records live: your invoicing app, your booking software, a spreadsheet, or the paper folder in your truck
• Claude
• About 30 minutes for the setup, then a couple hours of sending

Setup

1. Pull your list. Export or write down everyone who paid you between 6 and 24 months ago and hasn't been back. Most invoicing and booking tools have an export button, look for "Export" or "Download CSV" under customers or reports. If you're on paper, just type out the names.
2. Strip the sensitive stuff before you paste anything. You need first name, roughly what they bought, and roughly when. That's it. Delete addresses, card info, account numbers, anything medical. Leave phone and email in your own file, not in the prompt.
3. Run the first prompt to sort the list into groups. Different people need different messages.
4. Run the second prompt to write the messages.
5. Send them yourself, a few at a time, over a week. Not all 200 at once from one number, that's how you get flagged as spam.
6. Put a recurring reminder on your calendar for every 3 months. That's the whole system.

The prompts

Sort the list:

I run a [YOUR BUSINESS TYPE] in [YOUR CITY]. Below is a list of past
customers who haven't bought from me in a while. For each one I have
their first name, what they bought, and roughly when.

Sort them into groups based on the best reason to reach out to each
one. Think about things like: people whose thing is probably due for
service again, people who bought once and never came back, people who
used to be regulars and stopped, people who spent a lot, people whose
purchase suggests they'd want something else I offer.

Tell me what groups you made and why. Then tell me which group I
should contact FIRST and why that one.

Here's the list:
[PASTE: first name, what they bought, roughly when. Nothing else.]

Write the messages:

Same business. Write a message for each group you just made.

Rules:
- Text length, under 300 characters, unless you tell me a specific
  group should get an email instead and why
- The first line has to prove I know who they are. Reference the actual
  thing they bought. Generic openers get deleted.
- Give them a real reason I'm reaching out that isn't "we miss you"
- No discount in the first message. If a discount belongs anywhere,
  tell me which group and why.
- Make it dead easy to reply with one word
- Never guilt them for not coming back
- Do not say "long time no see" or "we haven't seen you in a while"
- Written how I talk: [DESCRIBE OR PASTE A REAL MESSAGE]

Write the follow-up for the ones who answer:

Same business. When someone from this list replies, write me short
responses for the 4 most likely answers:
1. They're interested, what's next
2. They already went with somebody else
3. They don't need anything right now
4. They had a bad experience last time and didn't tell me

For number 4, do not be defensive. That's a gift, treat it like one.
Show me how to actually fix it and ask them back.

What to check before you trust it

Cross-check the list against your recent work before you send. Texting "haven't seen you in a while" to someone you did a job for last month makes you look like you don't know your own business.

Check every name against people you let go on purpose. There's always a few. Leave them off.

Personalize the first line of every single message by hand. Yes, all of them. That's the one line that decides whether the rest gets read.

Space them out. Twenty or thirty a day, max, from a normal phone number. Blasting 300 texts at once gets your number flagged and then nothing you send lands.

If somebody says stop, stop, and take them off permanently. There are actual laws about this for texts and emails, and beyond that it's just the right way to operate.

Don't attach a discount to the first touch. You'll train the list to only respond when there's money off, and then you've made your own margin problem.

— Jordan