Yana G.Y. is a director at a bank. Full-time, board minus one level, the whole corporate package. On the side, she runs Unplugged by Yana, a Substack that just crossed $20,000 in a single month.
And no, she doesn’t publish more than you. She automated the parts of the business that most Substack writers still do by hand, usually badly, and the automations now do the selling for her.
I interviewed her live this week and made her walk me through the entire system. Here’s what she actually built, piece by piece, and what you can copy this month.
FYI: I just updated my premium membership. It now includes my entire AI skill system, the one I use every single day. The Viral Notes writer, the Anti-AI Writer, the full article pipeline, all of it. You can buy them individually for $49 each here, or get them all as part of my premium membership.
The question that changed everything
Before any automation, Yana made one decision that most substackers skip.
New writers ask her the same questions constantly. What should I write about? How do I grow my audience? She says those are the wrong questions.
The right question is: what do I sell?
Her comparison was a great example: No physical shop opens its doors and starts advertising with empty shelves. That’s exactly what most creators do on Substack. They write for months, build an audience, and only then wonder what the product is.
Yana started with the product. She noticed that people wanting to learn AI were drowning in free education and still didn’t know where to start. So instead of teaching AI, she built ready-made custom GPTs her paid subscribers could plug in and use. At one point, 200 of her 400 paid subscribers had downloaded them. Half her paid base came from one product insight.
Everything else in this article sits on top of that decision, because you can’t automate the selling of a product that doesn’t exist.
Automation 1: The free-to-paid email machine
This is the big one. It now drives 50 percent of her paid subscription growth, and she hasn’t manually promoted her paid tier since she built it.
Here’s the setup:
Substack notifications for new subscribers get forwarded to email
Make.com reads those emails and extracts the subscriber’s address
The address lands in Kit, which triggers an automated sequence
When someone upgrades to paid, another trigger pulls them out of the sequence
The sequence itself is where her marketing background shows. Days 1 through 10: a free email course on growing your first 1,000 subscribers. It doubles as her lead magnet. Days 11 through 20: pure sales, explaining her paid subscription with a time-limited promotional offer.
The timing is deliberate. From her corporate work she knows new subscribers convert within their first one to three months. After that they go cold, and almost no amount of effort brings them back. Most substackers let that window close in silence. Her system sells into it automatically, every single time someone subscribes.
She subscribed to dozens of newsletters when she joined Substack to check whether others were doing this. Almost nobody was. She kept thinking she must be missing some good reason people skip it, and eventually concluded there just isn’t one.
Automation 2: The webinar that sells while she sleeps
Yana built a large course called the Substack Quest and couldn’t sell it. Emails alone weren’t enough. She felt embarrassed about it, marketing director that she is.
She saw others selling big courses through live masterclasses. But she has a day job. Running live webinars every week wasn’t an option.
So she asked ChatGPT to find her a platform that automates webinars. It suggested eWebinar, a tool she’d never heard of. She recorded one masterclass, studied what makes masterclasses convert, mapped the structure from proven examples, and set it to run on autopilot with built-in interactions that keep people engaged.
The result: 10 percent of everyone who signs up for the free masterclass buys the course. That’s roughly $5,000 of her $20,000 month, fully automated.
The masterclass gets promoted at the end of her Kit sequence, to subscribers who went through the sales emails and didn’t join her founding tier. So everyone who enters the funnel gets offered a next step, whichever door they didn’t take the first time.
The growth engine: One mega post, engineered to spread
Automations convert subscribers. She still needed more subscribers coming in.
Her answer wasn’t posting more often. She wrote one 10,000-word post answering every question a Substack beginner could have, framed around her 500 paid subscriber milestone. She knew posts like that tend to get distributed by Substack’s algorithm.
She published it. Nothing happened.
So she engineered the traction manually. She asked people to share it and shared their posts in return. She linked to it from every other post she wrote. Dozens of small, unglamorous actions. Eventually the post caught, got picked up by Substack’s distribution, and became her biggest source of new free subscribers. A viral note about her 700 paid subscriber milestone added another wave.
Her takeaway was almost annoyingly simple: once your conversion funnel works, growth is just a leads problem. Get more free subscribers in and the funnel turns a predictable share of them into revenue.
She then poured fuel on it with Meta ads, mostly Facebook, getting free subscribers at around $2 each and eventually cracking paid subscriber acquisition too. Her margins dropped from 60 to 30 percent. She’ll take it, because the absolute cash is higher.
The fear that keeps everyone else broke
I asked her about the worry I hear constantly, especially from smaller accounts: won’t all these emails annoy my subscribers?
Her answer: that’s a problem in your head, not in your data.
When you send more emails, one or two people will write you something nasty. Those same emails are running your business. The people who unsubscribe over a sales email were never going to buy, and removing them cleans your list.
Her test for the fear goes like this. If you owned a physical shop, there would be no day, no hour when you’d choose not to sell. A newsletter business is still a business, and you’re the owner.
What to build first if you’re small
Yana’s system took years of trial and error. I asked what someone with 300 subscribers should do first.
Decide whether this is a business or a hobby. If it’s a business, decide what you sell before you optimize anything else. Build something small, give it to a few people free or cheap, learn what they actually need, and grow from there. She did exactly this with fans who followed her from Medium.
Then, in order:
Nail one offer that solves a proven problem
Set up a simple welcome sequence that sells it inside the first 90 days
Write one definitive post in your niche and push it relentlessly
Only then: automate, upsell, run ads
The order matters more than the tools. Yana said it herself about her ads: they only amplify what’s already working, and if the funnel underneath is broken, they just create a bigger disaster faster.
Yana’s last words on the live: go build your product and monetize, because now would be the time. I couldn’t have scripted a better ending.
Quick FAQ
What tools does Yana’s system run on?
Make.com to catch Substack’s new-subscriber notifications, Kit for the email sequences, and eWebinar for the automated masterclass. She stays with Kit over Substack’s native automations because it gives her segmentation, triggers, and visibility into what actually got sent.
Can’t I just use Substack’s built-in automations?
Maybe. They’ve improved a lot and Yana thinks they can replace Kit for many writers, but they’re currently limited to bestsellers. Kit also lets her pull people out of the sequence the moment they upgrade, which she can’t reliably track on Substack.
How is her email sequence structured?
Ten days of a free email course (her lead magnet, on growing your first 1,000 subscribers), then ten days of sales emails with a time-limited offer. The timing targets the first one to three months after someone subscribes, the only window where free subscribers reliably convert.
How much of the $20K is actually automated?
Roughly half. The Kit sequence drives 50 percent of her paid growth, and the automated masterclass adds about $5,000 a month at a 10 percent conversion rate. Coaching is the main part she still delivers manually.
Won’t more emails make people unsubscribe?
Some will. Yana’s point is that those people were never going to buy, and losing ten free subscribers to gain one paid one is a trade you take every time.
I have a small list. Where do I start?
Not with automation. Decide what you sell first, validate it with a handful of people free or cheap, then build a simple welcome sequence that sells it. Automate once something converts.
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Claudia Faith holds a Master of Science in AI. She’s a VC-backed founder who’s worked with Fortune Global 500 companies to deploy AI where it actually matters. As a Fractional Chief AI Officer, she handles strategy and implementation, and offers 1:1 coaching for business owners who don’t want to be the last in their industry to figure this out. If you want help thinking through your own AI strategy, start here.
