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Feb 27, 2025 6 min read

You gotta automate that

Quarter moon above the Gulf of Mexico - image credit: NASA

I’m in Mexico City sitting across from systems builder Devin Lee.

Systems have been on my mind all week because it’s hard to hang with Devin and not talk about them.

The reason we are in Mexico is that Devin, Kari Ginsburg and I talked about how we wanted to write books so we hatched this plan to have a writer’s retreat, but now that we’re here, only Kari has made good on the goal to write a book.

Devin and I are spending our time writing hella newsletters. Devin could probably be a competitive newsletter writer. She pumped out like 10 in an hour yesterday.

How does she do it?

She made a newsletter system.

SOUNDS USEFUL.

You might not know this about me, because I cosplay as someone who’s very organized, but I wing it a lot of the time. Especially if I’m not accountable to anyone else.

That’s not gonna cut it much longer. I’m hitting a growth plateau and it’s time to get serious.

To hit my next milestone of 200 paid contributors and I need to:

a) work faster
b) automate more

So here’s everything I am going to automate…

I talk a lot about how YOU need to automate. But I am very behind on my own automations and it’s time to take my own advice.

So I made a “You gotta automate that” map for myself, inspired by how Devin maps systems (she does that professionally by the way if you wanna hire her)

I’m sharing this automation set with you a little raw, but rest assured that I will be cleaning it up and posting it as recipes and instructions on the Paid Sub Playbook for you to grab soon.

In the meantime: View my automation map | Copy the template in Canva

Here’s what’s on the list…

Website
The more available the paid subscription is, the more likely people will subscribe. Right now it’s buried on my site and it needs a real sales pitch.

Homepage: Pin an intro post.

About page: Make it more scanable and plug the paid subscription (I love Max Read’s About page)

Contribute page: Sales page for the paid subscription. (Not that different from the About page, but more focused on the subscription).

Upgrade page: Make benefits sound more fun and make sure they’re all there.

Join page (on lexroman.com): Add both my paid subscriptions to my own website (lol)

Social media
I love using a tool like Hypefury to auto-plug my newsletter and subscription every couple days but they don’t support Bluesky so I’m building something with Airtable + Buffer + Zapier to recycle evergreen plugs.

Join the email list plugs: 10 messages that rotate and autopost throughout the month to encourage signups.

Get the Paid Sub Playbook plugs: 10 messages that rotate and autopost throughout the month to encourage subscription upgrades.

Just got a new subscriber triggers: This is already automated and it works so well, I wrote you the recipe.

When someone new subscribes (Welcome sequence)
Introduce them to me, this project and get them reading issues. I see welcome sequences as a habit builder and I wrote you a bunch of recipes here.

Welcome email 1: Why this newsletter/who is Lex

Welcome email 2: Best issue preview → read it

Welcome email 3: What the Paid Sub Playbook is

Existing reader who hasn’t upgraded (Upgrade sequence)
These are sequences that encourage regular readers to upgrade throughout the year. I call them “why pay” sequences and I will be writing recipes for you soon but you can also take any one off sales pitches you’ve sent that worked and plug ‘em in here.

3 months post-subscribe

Why pay email 1: Why I care about journalists making money

Why pay email 2: What’s in the Paid Sub Playbook

Why pay email 3: The vision for the Paid Sub Playbook

Why pay email 4: Bet you thought you’d never be the business guy

Why pay email 5: Why Paid Sub Playbook subscribers upgrade

6 months post-subscribe

Why pay email 6: Are you growing a paid newsletter?

Why pay email 7: Start with the 3×3×3 growth system

Why pay email 8: What’s in the paid sub playbook

12 months post-subscribe

Why pay email 9: You’ve been here a year. How’s your publication grown?

Why pay email 10: Where we’re heading with this project together

Why pay email 11: Best recent issue preview

Why pay email 12: Paid Sub Playbook success story

Why pay email 13: Needs a topic

When someone upgrades (Paid welcome sequence)
By far the highest priority sequence I need to work on because anyone running a subscription business knows retention and referral > acquisition. If I want subscribers to stick around, get the most out of this and be a contributing part of this project, I need better onboarding and year round communications.

Paid welcome email 1: Get access to everything/set up the 3×3×3 Growth System

Paid welcome email 2: How to get in touch with me, AMAs, events, questions

Paid welcome email 3: What to do with your 3×3×3

Paid welcome email 4: Top 5 ways to grow your newsletter (feat. 32 ways to grow your newsletter)

Paid welcome email 5: Set up a why pay automation

3 months post-upgrade

Paid adoption email 6: The 3×3×3, how it works and how to use it

Paid adoption email 7: Automated vs manual promotions

5 months post-upgrade

Paid adoption email 8: “Just got it” Subscriber automations

Paid adoption email 9: Creating a messaging bank

Year round

Quarterly check ins: how are subscriber goals going, biggest challenges

Biannual feedback/testimonial: ask for input and gather testimonials

Readers who don’t open emails (List clean sequence)
To remove inactive readers and/or win them back.

List clean email 1: Reminder of what the newsletter is, how you got here

List clean email 2: Recent popular issue

List clean email 3: What’s coming up this year

Whoa Lex! That’s so much work and I’m drowning in other work to do! How do we do it all!!!!!!

meme of so much work


Yep, it is a lot of work. I’ve been putting it off for weeks but one thing that will make it easier is knowing which one off emails I’ve already sent that landed well.

Behold! My beehiiv dashboard which shows me what already worked.

I particularly love the little dollar sign which signifies emails that paid subscribers liked (and motivated them to upgrade!)

my emails with stats
my emails with stats


Another thing I’m thinking about is how we can just take on a small slice of this every month or so—together. Pick one thing to make better at a time and not drown in the full weight of everything we could possibly do.

I’m cooking up an idea for how we do that and will share it with you soon.

The last thing I’ll mention is that you may not need to work this hard to grow your subscription business.

These are options. Opportunities. You might not need them. If you’re on track for your goals, nice work! You’re all set!

And also, if you haven’t run a manual promotion yet, don’t automate yet. Test your messages first, then automate them.

automation map

automation map
As for me, I definitely gotta get to work.

Check out my automation map and make a copy for yourself.

🎲 Lex

P.S. If you don’t have access to the Paid Sub Playbook and you’re part of Legends, send me a reply and I’ll add you.

Same goes the other way. All my paid contributors can have access to the full Lex universe. Just ask. I don’t add you to everything because it’s quite a lot.

P.P.S. Here’s us at Lucha Libre last night. It was the best.

Lucha Libre

Lucha Libre
Rob, Devin, Kari and me

Los luchadores in the ring in Mexico City


Los luchadores

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