In a nutshell:

• Walkthrough the all-new features of Substack that recently popped up in the app and on the publications

• The new publications of and how she grows using Instagram

• How grows using LinkedIn and his brand new book

• Welcomed a brand new VIP Member and talked about her upcoming launch

• The new ads monetization feature in Kit and how I use it

• Why Kit is useful for your Substack and how to use it to grow paid subscribers (I go deep into this in this video)

• and so much more…

This is the place where we share lessons, best practices, find collaborations, and help each other with anything that’s on our plate right now. We grow faster. Together.

Read more

If you’re serious about your Substack monetization, make this post your daily engagement routine. Share your posts, then read and join the conversation in the comments of the other members’ posts. This is how we grow!

If you’re not yet in the Writing Challenge, NOW IS the best time to join.

VIPs: You have new gifts👇

Here’s what you need to do now:

1. Add yourself to the Accountability tracker, so that you have a chance to win the award (a spotlight with me to get more exposure of your Substack)

2. Share a link to your posts in the comments below so that we can find it, read, comment, like, and share it!

3. Make this challenge for your daily engagement workflow - Check other people’s posts in the comments of this post. Find something you like to read more about and give it a like, comment and share - that’s how you grow faster (and you help others grow too).

Anyone from the Unplugged community can participate.

Let’s do this!!

Subscribe now

Share your link now 👇

P.S. If it doesn’t challenge you, it won’t change you. If you haven’t already, Join the Writing Challenge if you’re serious about growing on Substack.

P.S.S. If you’re not taking the Challenges, you can opt-out from receiving these weekly posts without unsubscribing for the rest of the content - do this from your settings here:

If you’re serious about your Substack growth, make this post your daily engagement routine. Share your Notes, then read and join the conversation in the comments of the other members’ Notes. It will help you and them grow.

Grab your Viral Notes Writer GPT & post some highly engaging Notes.

Notes are essential for your Substack growth. If you’re not yet in the Notes Challenge, NOW is the best time to join.

Here’s what you need to do now:

1. Add yourself to the Accountability tracker so that I consider you for the prizes.

2. Share a link to your Notes in the comments below so that we can find it, read, comment, like, and restock it!

3. Check other people’s Notes in the comments. Find something you like to read more about and give it a like, comment, and share. Make this challenge your daily engagement routine - it helps you, as well as the other members in the community, grow faster.

PLUS: if you have a Note with 100+ likes, DM me with a link, so that I can add it in the Unplugged Hall of Fame :)

You can share your Notes here throughout the whole week, until the next sharing post on Saturday.

Anyone from the Unplugged community can participate.

Subscribe now

Let’s do this!!

Share your link now 👇

P.S. If you haven’t already, Join the Notes30 Challenge if you’re serious about growing on Substack.

P.S.S. If you’re not taking the Notes Challenge, you can opt-out from receiving these weekly posts without unsubscribing for the rest of the content - do this from your settings here:

And every time I stare at that for a minute.

Because yes. I do.

And I keep repeating it - on lives, in Notes, in chats, in DMs…

But I never actually documented it, so this is it.

Truth is, I get on average ~ 3 new paid subscribers every time I publish a paid post.

And my conversion rate?

11.7%

That’s the highest free-to-paid subscriber conversion rate I got for people coming from Notes and App. Now it gravitates around 9% to 10%.

And I’m now at 534 paid subscribers and more than $22k in ARR, growing double-digit month over month:

How?

It took me an embarrassingly long time to recognize it as a template at all. I thought I was just writing the way that felt right. But when I analyzed my posts with AI (and I do that a lot) - especially the ones that had the highest conversion, there was a pattern.

The same seven elements. Every single time.

And when I tested posts without them? My conversion rate drops.

Why your posts aren’t converting, even when the content is good

Here’s the thing most Substack writers don’t talk about when they talk about newsletter growth.

You can have excellent content and terrible conversion. They’re not the same thing.

I see it constantly. Writers who are clearly smart, clearly writing useful stuff, with subscriber counts that should be printing revenue, and they’re not. The paid subscriber numbers are flat. Or growing at maybe 1–2% when they could be growing at 8–10%.

It’s not a content quality problem. It’s a structure problem.

When someone discovers you through Substack Notes, they arrive warm. They already liked something you wrote. They clicked through because they want more.

That’s an incredible moment, and most posts immediately waste it by opening with the same generic “here’s what I’m going to cover today” blog structure that gives the reader no reason to feel anything.

The result: they read the post, think “that was decent,” close the tab, and stay free forever.

Growing on Substack requires converting that moment of attention into a decision. Not a purchase decision, but an identity decision. “I see myslef in this.”, “This is me”, “This hit hard”, and ultimately “This is someone I want to follow at the paid level.”

That only happens when a post is built to produce it.

The thing that makes the difference

It’s not what I write about. Not so much my offers. Not even my posting frequency.

They do matter, but it’s something else.

The order of information inside every post.

That’s the pattern my AI analysis revealed.

And I repeat this everywhere:

My high-converting paywall strategy, in a nutshell: Give the WHAT and the WHY for free, paywall the HOW.

Simple. But not always easy to implement.

I lead with proof before I led with advice, and I started closing with a path instead of just a summary. And I added five other structural elements that each do a specific job in the conversion sequence.

Every element has one job. And the framework follows a specific logic - it moves through two dimensions before it ever asks for anything.

It’s a 7-part post structure I use for every almost Write2Sell piece and every post designed to convert. With a very intentional paywall placement logic (not just “put it in the middle”).

But you don’t have to remember this, I made an easy-to-follow checklist you can print today and have it by your side every time you decide to paywall.

Let’s get to it.

The 7-part paid post structure in a nutshell

I might have made you think it’s just 3 parts - the WHAT, the WHY and the HOW, but they are actually 7.

Why?

Because you have to work on both - emotional and rational triggers to make people buy.

When one element is missing (or out of order) the whole sequence breaks. And if you’ve been wondering why your posts get decent engagement but don’t convert subscribers to paid, the answer is almost certainly somewhere in those seven elements.

So here’s how they fit inside my high-converting paid post structure (no need to remember it, find the checklist at the end of the post)…

Read more

If your Substack has stalled and you can’t figure out why, run this diagnostic before you rewrite a single piece of content:

Your content is probably fine. Your positioning is probably the problem.

Positioning isn’t your niche. It’s who the reader thinks you are when they read you. If you’re an expert and you’re showing up as just another writer, you’re leaving your conversion rate on the table.

Build your positioning around what makes you specifically different. Not around what sounds good on a landing page.

Stack your content into clear pillars the reader can navigate. Kathleen’s three: understanding → stabilizing → rebuilding. Borrow the shape, not the topics.

Pick an offer that matches how you actually work best. One-on-one or group. Async or live. Depth or reach. Your conversion rate will thank you.

Don’t delete your quiet subscribers. The person not opening today is often the person buying in eighteen months.

And when your numbers dip (and they will) don’t panic. Diagnose, fix, keep showing up. Prepare for the up.

Watch on YouTube:

Few days ago I went live with

She’s a registered nurse of 30 years. A massage therapist of 18. A root-cause practitioner who looks for patterns most healthcare professionals miss. She’s been on Substack since June 2024, almost two years in at this point.

And she’s with me as a VIP Lifetime member ever since.

A few weeks ago she opened up the custom GPT I built for her, typed out her positioning and her topics and her current setup, and asked it for suggestions. She was expecting something about tone. Frequency. Maybe a content mix adjustment.

Instead, the GPT told her this:

“Everything you’re saying, what you’re doing, is accurate. But your positioning is not.”

That one sentence rewired her entire Substack strategy.

If your Substack feels stuck right now - not crashing, just quietly going flat - sit with that quote for a second. Because it might be your diagnosis too.

The numbers that stopped climbing

Let me give you the context before I get into the fix.

After Kathleen joined me things moved. Within a few months she was making $500 to $600 a month on Substack. That’s real momentum for someone in her first year on the platform.

Then around January-February it went flat.

February was $125. March was $155.

She wasn’t slacking. She was showing up. Writing. Posting. The content hadn’t gotten worse. And I want to stop here because this is the moment where most people misdiagnose what’s happening.

They blame the algorithm.

They blame their audience.

They blame their content quality.

And they start tweaking things that aren’t actually broken.

On the live, Kathleen kept asking “what changed?” And here’s what we landed on together.

Nothing changed about her work. What changed was that the quiet positioning mismatch she’d been carrying since day one finally caught up with her audience. New readers were subscribing to what they thought she was. Then realizing she was something else. Then churning. Old readers weren’t re-engaging at the same rate because the thing they’d subscribed for didn’t quite match what they were getting.

That’s how positioning failures surface.

What positioning actually is (and what it isn’t)

Most people confuse positioning with niching.

They’re not the same thing.

Niching is what topic you write about or, as I like to look at it, what problem you solve. Positioning is who the reader thinks you ARE when they read you. A health writer can niche into “gut health” and still fail at positioning because the reader can’t tell whether they’re reading a journalist, a coach, a clinician, a recovery story, or someone curating other people’s advice.

Here’s Kathleen’s specific version of this failure.

She was writing on Substack about stress, health, nutrition, and disease prevention. All topics that sit squarely inside her 30 years of clinical experience. So far, so good.

But she was showing up on the page as a WRITER - one voice among thousands of other Substack wellness writers. Her clinical authority wasn’t visible in how she framed herself.

The thing that actually makes her different is far from writing - she can order labs, she tracks patterns instead of single data points, she’ll tell you why your “normal range” potassium might not be normal for YOUR cardiac history - none of that was in her positioning.

The reader arriving at her publication couldn’t feel any of it. So they subscribed thinking “another wellness writer,” got a wellness writer, and either stayed flat or churned out quietly.

This is what I mean when I say you can have great content and broken positioning at the same time. The content works at the sentence level. The positioning fails at the who-is-this-person level.

And positioning is where conversion lives.

Here’s a video from the Substack Quest where I go deep about positioning:

How Kathleen repositioned

This is the part I want you to actually use.

She pivoted from “writer” to “expert practitioner who also writes.” Small distinction on paper. Huge consequence in practice.

She built three clear pillars:

One: Stress physiology & disease prevention. The understanding layer. Education grounded in her clinical background.

Two: Stress regulation & applied tools. The stabilizing layer. Practical protocols for people already in the thick of it.

Three: Survival, grief, and nervous system recovery. The rebuilding layer. This is where her lived experience lives.

Huge difference if you ask me.

Kathleen also made a specific business-model decision on the call that I want to flag. She said:

“I could make more money doing Zooms and do a bunch of people, but that’s not how I work best.”

She’s choosing one-on-one consultations over group calls. Less scalable. But she knows herself well enough to know that her conversion, her energy, and her client outcomes are all better when she goes deep with one person than wide with twenty.

That’s what positioning looks like when it’s done honestly.

It’s not just what your content says. It’s what your offer structure actually matches.

The moment she almost threw it all away

Earlier this year, Kathleen deleted about 25 email addresses from her list.

Someone on Substack had convinced her that inactive subscribers were hurting her performance. Her open rates. Her deliverability. The standard list-hygiene advice that circulates in creator circles.

She deleted.

Then she asked me about it. And I said, I hate to break it to you, but those were still your people.

Here’s the logic. The person who’s unsubscribed is telling you something - they’re done. That’s a clean signal, and yes, a clean list. But the person who’s just quietly not opening? They’re not telling you anything yet. They might be busy. Grieving. Broke. Burned out. Between jobs. Waiting for the right moment. Saving up for a bigger purchase.

Some of those 25 emails were going to buy her offer six months, a year, two years later.

You don’t delete those people.

Never make a decision based on someone else’s opinion.

If you’re going to prune your list, do it because YOU decided based on your data, your audience, your funnel, your deliverability. Not because someone on a podcast or in a Note said inactive emails hurt your algorithm.

Quiet is not gone.

The one piece of advice she wanted people to hear

Near the end of the live I asked Kathleen what she wanted people watching to take away.

Her answer was short.

“Don’t give up. Make the commitment. Be consistent. Don’t get discouraged, we’re going to get discouraged, but don’t let it stop you.”

And here’s why this lands differently coming from her than from almost anyone else I’ve had on for a live.

Kathleen just had a $125 month. In public. She told me the number on camera without flinching. She could’ve said “a down month” or “a rough quarter” or any of the softer phrases creators reach for when the number is embarrassing.

She gave the exact dollar figure.

Because that’s what consistency actually looks like. It’s the months where your number drops by 75%, and you keep writing, keep showing up, keep fixing what’s actually broken (like the positioning) and you trust the next up-cycle is coming.

You prepare for the up while you’re in the down.

That’s the whole game.

Watch the full live above for the parts I couldn’t fit in here. Kathleen goes deeper on the root-cause approach she uses with her clinical clients, the YouTube + Substack ecosystem strategy that’s growing both her channels at once, and why her Croatian Substack subscriber is flying into Atlanta in May to stay at her house for ten days. (Yes, that actually happened, and it started with a comment on a Note.)

Go subscribe to Kathleen’s publication — she’s one of the most grounded, honest voices on this platform, and she’s doing the repositioning work out loud in real time. That’s rare, and it’s worth watching up close.

Yana

P.S. Kathleen mentioned the QUEST several times on the live — she’s a VIP lifetime member, and going back through the foundations is the exact work she’s doing right now to tighten her positioning. If you want the same system she’s using, it’s here.

Kickstart Your Substack Growth:

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Wall of Love

If you’re serious about your Substack monetization, make this post your daily engagement routine. Share your posts, then read and join the conversation in the comments of the other members’ posts. This is how we grow!

If you’re not yet in the Writing Challenge, NOW IS the best time to join.

VIPs: You have new gifts👇

Here’s what you need to do now:

1. Add yourself to the Accountability tracker, so that you have a chance to win the award (a spotlight with me to get more exposure of your Substack)

2. Share a link to your posts in the comments below so that we can find it, read, comment, like, and share it!

3. Make this challenge for your daily engagement workflow - Check other people’s posts in the comments of this post. Find something you like to read more about and give it a like, comment and share - that’s how you grow faster (and you help others grow too).

Anyone from the Unplugged community can participate.

Let’s do this!!

Subscribe now

Share your link now 👇

P.S. If it doesn’t challenge you, it won’t change you. If you haven’t already, Join the Writing Challenge if you’re serious about growing on Substack.

P.S.S. If you’re not taking the Challenges, you can opt-out from receiving these weekly posts without unsubscribing for the rest of the content - do this from your settings here:

If you’re serious about your Substack growth, make this post your daily engagement routine. Share your Notes, then read and join the conversation in the comments of the other members’ Notes. It will help you and them grow.

Grab your Viral Notes Writer GPT & post some highly engaging Notes.

Notes are essential for your Substack growth. If you’re not yet in the Notes Challenge, NOW is the best time to join.

Here’s what you need to do now:

1. Add yourself to the Accountability tracker so that I consider you for the prizes.

2. Share a link to your Notes in the comments below so that we can find it, read, comment, like, and restock it!

3. Check other people’s Notes in the comments. Find something you like to read more about and give it a like, comment, and share. Make this challenge your daily engagement routine - it helps you, as well as the other members in the community, grow faster.

PLUS: if you have a Note with 100+ likes, DM me with a link, so that I can add it in the Unplugged Hall of Fame :)

You can share your Notes here throughout the whole week, until the next sharing post on Saturday.

Anyone from the Unplugged community can participate.

Subscribe now

Let’s do this!!

Share your link now 👇

P.S. If you haven’t already, Join the Notes30 Challenge if you’re serious about growing on Substack.

P.S.S. If you’re not taking the Notes Challenge, you can opt-out from receiving these weekly posts without unsubscribing for the rest of the content - do this from your settings here:

Not $50k. Not “six figures while you sleep.”

$5,804.

I’m putting that number right at the top because the internet is full of people selling you a $10k/month, even $100k/month - and the moment you open their “blueprint” it’s a bunch of bullet points about “mindset” and a link to their $2,000 cohort.

This is not that.

This is the actual math and what it takes to get there. Every month.

The exact model I follow for my self and for my 1:1 clients. I’m also gonna give you a one-pager cheatsheet pdf which you can print and follow.

So here’s what $5,804/month looks like for me today (I hit 5k every month, and I do this on the side of my 9-5):

Four income streams. Running in parallel.

Not one spike and then praying a Note goes viral.

And here’s the part most people don’t realize: you can hit this with a tiny list.

Paid member Jennifer Dragonette, said it better than I ever could: “I have 19 subscribers and I already got a paid high ticket client from here.”

Nineteen. Subscribers.

So if you’re sitting on 100 free subs thinking “I need 10,000 before I can monetize,” stop. That’s the wrong math. The right math is the one above.

Now.

The reason most people never hit $5k/month on Substack isn’t audience size. It’s not niche. It’s not talent.

It’s that they’re running one engine.

You need three.

Why Substack beats every other platform for this

Before I break down the engines, let me answer the question I get often: why substack and not [literally anything else]?

Short version?

Substack is the only platform I know of that gives you blog, podcast, social, newsletter, community, AND monetization in one place. Without paying for six separate tools and wiring them together with duct tape.

That’s six tools collapsed into one. At $0/month to start.

And the best part? You post and you get subscribers, not just followers.

Every other platform gives you rented audience. Substack lets you own it.

Bottom line: the platform already stacks the deck for you. You just have to build the system on top of it. I wrote a very detailed breakdown about how Substack works, check it if you’re new to the platform:

The 3 engines behind $5k/month

OK. Here’s the whole model.

Three engines. Running at the same time. Each one doing a specific job.

#1 The Offer Engine (what you sell)

This is where you start.

Not the audience. The offers.

This is the portfolio. Here’s how mine looks like today:

• DIY at the low end (guides, templates).

• DWY in the middle (courses, GPTs, workshops).

• DFY at the top (done-for-you services, high-ticket coaching).

Intertwined with my paid subscription and building on top of it.

Plus - my paywall formula: WHY and WHAT stay free. HOW goes behind the paywall.

#2 The Growth Engine (how you grow)

This is not “post more.” This is a specific stack of levers that feed your Substack business with fresh blood:

• Notes, 3 to 10 per day

• Engagement, replies to every comment daily

• Collaborations, cross-posts, guest posts, lives

• Recommendations, the most passive growth feature Substack has

• Posts, one SEO-optimized free post per month

• Lead magnet inside the welcome email

Recommendations alone have brought me thousands of subscribers with zero extra work. 4,308 to be exact.

If you’re not set up to give AND receive them, you’re leaving the biggest free growth channel on the table.

#3 The Sales Engine (how you sell)

Here’s the part most people miss. 71% of buyers convert in the first 30 days of subscribing. If you don’t have a welcome sequence pointing at a paid offer, you’re watching money walk out your door.

Every post must point to a paid offer with a CTA. No exceptions. And you’re selling transformation, not information. Information is free on the internet. Transformation is what people pay for.

From there I optimize with automations. Sequences, funnels, up-sells, x-sells. You can do that manually, but you have to do it every month and it’s less efficient. For someone with a 9-5 I prefer to outsource to the machines.

If your engine needs you to show up every day to produce sales, it’s not a sales engine. It’s a job.

The ONE BIG thing most people still overlook

Here’s what I wish someone had told me two years ago.

All three engines have to run at the same time. Not one at a time. Not “I’ll focus on growth this quarter and monetization next quarter.” At the same time.

Why?

Because growth without an offer is a waste of effort. An offer without growth is a dead page. And sales automation without either is an empty pipeline.

That’s why “grow your audience first” advice is dead. It’s as if you launch adverting and you’re leading people in an empty shop.

This model is the difference between a creator who complains about burnout and a creator who takes a Sunday off and still makes money.

How to actually build this

This doesn’t happen overnight. It needs a structured order.

There’s a certain way to build these three engines and things you can do that get you to $5k/month faster than the “figure it out as you go” approach I see most people take (and then quit, six months in, blaming “the algorithm”).

Today I’m giving you the exact 5-step build order that took me to consistent $5k+/month with 500+ paid subscribers at a high free-to-paid conversion rate.

Here’s what I did and how you can replicate it in 5 simple steps…

Read more

She’s a bestselling author, a storytelling strategist, and a top 1% podcaster. She also had 19 Substack subscribers. And she already landed a high-ticket coaching client off this platform.

Nineteen.

Sit with that number for a second. Because every time someone tells me they “need 10k subscribers before they can monetize,” I think of conversations like this one.

What's her secret?

No secret. She just applied the strategies in the SUBSTACK QUEST with what she already knows best: how to use storytelling for business.

You can watch the full recording above. But if you want the condensed version, here’s what stuck with me.

The quote I can’t stop thinking about

Halfway through the live, I asked Jennifer what she thinks about Substack compared to the other platforms she’s used.

Here’s what she said:

“I have 19 subscribers and I already got a paid client from here.”

Then she clarified. It wasn’t a paid subscriber. It was a high-ticket client. Someone found her on Substack, a conversation happened, and that person became a high-ticket client.

19 Substack subscribers → one high-ticket client → pretty decent money off Substack already.

Compare that to the standard growth advice. Grow first, monetize later. Wait until you hit 10k.

You know me, I lean on data. And the data says something different. Monetization isn’t about audience size. It’s about the match between the reader and your offer.

Jennifer is the living proof.

Why she’s done chasing virality

Jennifer came to Substack burned out.

Top 1% podcast. Bestselling book. Keynote on a stage of 3,000 people last year. All the metrics most creators are trying to hit.

And she said this, out loud: “I’m done with virality.”

Ok, let me tell you why that line hit me. A lot of us nod along the first time we hear something like this - and then go back to chasing subscirbers on Notes the next morning.

Jennifer’s argument is different. She’s not saying virality is bad. She’s saying it didn’t build her business.

Her top 1% podcast, her viral stage moment, her thousands of listeners - those didn’t move the needle the way one real Substack conversation with the right person did.

She calls it “look at me” content versus “oh my goodness, that sounds like me” content.

The second one is what converts.

And Substack, she argues, is structurally built for the second one. “It’s a depth platform,” she said. “I like to go deep with people.”

The storytelling technique that changed how I think about content

This was the part of the live where I had to stop and process.

I asked Jennifer for one technique anyone could use to find their story. I was expecting a framework. Three steps. Maybe a worksheet.

Her answer:

Record yourself telling your whole story. Then listen back. Pay attention to where your body reacts.

That’s it. That’s the whole method.

“There’s going to be parts of that story that are going to react in your body,” she said. “Those are the parts that you infuse into your thing.”

Here’s why this is brilliant.

Most people try to manufacture a story that “sells.” They look for the problem hook. The one that sounds marketable. The transformation story that’ll test well on a sales page. And the result is content that sounds performative….because it is.

Jennifer’s method flips it. Your body already knows what matters. The lump in your throat, the tightening in your chest, the place where your voice catches- those are the moments of actual truth. And those are the only moments that transfer emotionally to a reader.

Try it this week. See what happens.

The metric that isn’t a vanity metric

asked a great question in the chat: how do you quantify storytelling beyond engagement metrics?

I watched Jennifer light up.

Her answer surprised me.

“For me, 19 subscribers and a paid client - that’s a pretty good metric.”

And she asked me back: “If that was your metric, would that be enough for you for knowing a story was great?”

Ok, I’ll be honest. I’m a data person.

My version of her answer would probably involve conversion rates, cohort analysis, and a dashboard. I shared with her that I currently run around 9–10% free-to-paid conversion for readers coming from Notes and recommendations — which is well above the Substack benchmark, and it’s a number I track closely.

But Jennifer’s deeper point is right. Engagement for its own sake is noise. The real metric is whether it landed somewhere. Whether it changed something. Whether a person did something different because of what you wrote.

Her 19-to-1 ratio? Actually, that’s a better conversion than mine.

Your competitors aren’t competitors

I believe competitors are your best collaborators.

And Jennifer shares this belief.

When she talks about other creators in her niche, she doesn’t call them competition. She says they’re “hanging out on your block.”

“We’re having a block party,” she said. “Who can you kind of collaborate with - their audience might share your audience, you might be able to give and take.”

This is such a better model than the scarcity-brained creator advice of “find your gap in the market and defend it.” Especially on Substack, where the whole platform is built around collaborations, cross-recommendations, restacks, and guest appearances.

Her entire business runs on referrals. Not because she has some sophisticated affiliate program. Because she showed up and gave first, for years. The block party kept growing until it became a business.

If you’re wondering what to actually do on Substack besides posting - this is it. Go to the chat. Do restacks with intention. Set up lives. Comment meaningfully on people you actually admire. Reach out for a collab. That’s the work.

What she’d do differently (this is the good part)

I asked Jennifer what she’d change if she could rewind her Substack journey.

Three things:

• Turn on paid from day one.

• Launch the founding membership immediately.

• Go back to the foundations before anything else.

“Substack offers you such great opportunities,” she said. “I would have turned on paid sooner. I would have launched my founding membership as my community.”

This is exactly what I keep telling new writers. And Jennifer is the proof of why it matters. She enabled paid once she realized what was possible - and within weeks she had a high-ticket client from the platform.

Most people wait until they have “enough” subscribers before they monetize. And they miss the window where the tiny, early audience is often the most ready to buy.

If you’re new here and still holding off on turning paid on — this is your sign.

One thing I’d add to what Jennifer said

Jennifer’s whole argument is that Substack rewards depth over surface. I agree with her. But I’d add a layer.

Depth without structure is still a hot mess.

Jennifer said this herself. She described her early Substack as “a hot mess express.” Then she went through the QUEST, did the foundations, tightened her positioning, clarified her offer - and the results followed within weeks.

The story matters. But the story has to be attached to an offer someone can actually buy.

That’s the piece a lot of storytelling-first creators miss. They get so invested in crafting the narrative that they forget to build the product underneath it. Then they wonder why the beautiful writing doesn’t convert.

Jennifer’s 19-to-1 happened because the story AND the offer were both in place. Not one without the other.

The TLDR version

If I had to compress this live into something you can actually use on your Substack this week:

You don’t need a big audience. You need the right readers and an offer that fits them.

Find the parts of your story that react in your body. Those are the parts worth sharing. Everything else is filler.

Stop chasing virality. Start chasing depth. Substack is built for the second one.

Turn on paid on day 1. Not after 1k subs. Not after 10k. When the offer is clear - that’s where you start.

And talk to people. In the chat. In restacks. In lives. Substack is not a content machine, it’s a place to connect.

Watch the full live above for the parts I couldn’t fit in here. Jennifer goes deeper on the storytelling method, the referral strategy, and the moment she almost tapped out of Substack early on.

And if you’re into story-first business, subscribe to Jenn’s publication - she’s one of the most grounded, vulnerable, and practical voices I’ve met on this platform in a long time.

Yana

P.S. Jennifer mentioned the QUEST several times in the live, that’s the 7-domain Substack strategy system she went through before her foundations clicked. If you want what she had, it’s right here.

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I want AI to send me clients

You have a product. Nobody is buying it.

You did the things you were supposed to do.

You built something real. You showed up. You created content. Maybe you even ran some ads. And it still feels like you are invisible.

Meanwhile the internet is flooded with “make money with AI” content. Use AI to write faster. Use AI to post more. Use AI to create digital products.

I tried it too. Most of it is AI-generated content that is barely worth putting your name on. That is what most people do to make money with AI: generate something, launch ads, count on one-time sales. That is not sustainable.

The problem is not how much content you create. The problem is that AI does not know you exist, and AI is now where your buyers go to find people like you.

37% of people now start their search on AI tools like ChatGPT, Claude, and Gemini. Not Google. Not social media. AI.

And when someone types “recommend me a good [your niche] course”, AI gives them 3 names. That is it. No page 2. No second chance.

Either your name is one of those three, or you simply do not exist to that buyer. Most people are still sleeping on this. That is the gap. And it is getting bigger every month.

The old way (Google)

1. Search Google

2. Click 10 links

3. Compare options

4. Read reviews

5. Ask people on social media

6. Evaluate more

7. Decide. Maybe buy.

The new way (AI)

1. Ask AI

2. Get 3 names

3. Click one

4. Buy.

4 steps · minutes.

This is not future speculation. This is already happening. One of those buyers found me through ChatGPT and signed up for my highest coaching package. Another found me through Claude and another through Google and became a paying founding member. This is happening to me right now, and it can happen to you. If you implement what I’m giving you.

Here’s what ChatGPT said about me:

What’s Inside:

• The BIG Shift

• AI SEO vs Google SEO

• Optimize Your Articles for AI Recommendations

• Optimize Your Sales Pages for AI Recommendations

• Elements that increase AI recommendations

• Optimizing for the major AIs

• How to Optimize for Specific Keywords

• How to Optimize Titles

• The Importance of Video

• How to Use Link Building

• The most important metrics to track

• AI TOOLS - Sales Page & Article Optimizers

• The only way to make money with AI

• Build Your High-Converting Products

In the Unplugged Toolbox (also linked in the Notion Doc):

• AI TOOLS: SEO & AI SEO Audit & Optimization for ChatGPT, Gemini and Claude for your Sales Page and Article (this thing is gold)

• THE ULTIMATE SEO & AI SEO CHECKLIST

• SEO COMPARISON: GOOGLE vs AI

• How to post same article on Medium SEO Friendly way

VIP Only: Here are the Links to the Notion Doc & The Unplugged Toolbox:

Read more

If you’re serious about your Substack monetization, make this post your daily engagement routine. Share your posts, then read and join the conversation in the comments of the other members’ posts. This is how we grow!

If you’re not yet in the Writing Challenge, NOW IS the best time to join.

VIPs: You have new gifts👇

Here’s what you need to do now:

1. Add yourself to the Accountability tracker, so that you have a chance to win the award (a spotlight with me to get more exposure of your Substack)

2. Share a link to your posts in the comments below so that we can find it, read, comment, like, and share it!

3. Make this challenge for your daily engagement workflow - Check other people’s posts in the comments of this post. Find something you like to read more about and give it a like, comment and share - that’s how you grow faster (and you help others grow too).

Anyone from the Unplugged community can participate.

Let’s do this!!

Subscribe now

Share your link now 👇

P.S. If it doesn’t challenge you, it won’t change you. If you haven’t already, Join the Writing Challenge if you’re serious about growing on Substack.

P.S.S. If you’re not taking the Challenges, you can opt-out from receiving these weekly posts without unsubscribing for the rest of the content - do this from your settings here:

If you’re serious about your Substack growth, make this post your daily engagement routine. Share your Notes, then read and join the conversation in the comments of the other members’ Notes. It will help you and them grow.

Grab your Viral Notes Writer GPT & post some highly engaging Notes.

Notes are essential for your Substack growth. If you’re not yet in the Notes Challenge, NOW is the best time to join.

Here’s what you need to do now:

1. Add yourself to the Accountability tracker so that I consider you for the prizes.

2. Share a link to your Notes in the comments below so that we can find it, read, comment, like, and restock it!

3. Check other people’s Notes in the comments. Find something you like to read more about and give it a like, comment, and share. Make this challenge your daily engagement routine - it helps you, as well as the other members in the community, grow faster.

PLUS: if you have a Note with 100+ likes, DM me with a link, so that I can add it in the Unplugged Hall of Fame :)

You can share your Notes here throughout the whole week, until the next sharing post on Saturday.

Anyone from the Unplugged community can participate.

Subscribe now

Let’s do this!!

Share your link now 👇

P.S. If you haven’t already, Join the Notes30 Challenge if you’re serious about growing on Substack.

P.S.S. If you’re not taking the Notes Challenge, you can opt-out from receiving these weekly posts without unsubscribing for the rest of the content - do this from your settings here:

If you’re new to Substack or you already have a Substack but you feel stuck, your newsletter has slow growth and you struggle to convert paid subscribers.

Save this playbook - you’ll want to come back to it many times in the future. It has everything I wish I had on day one.

You’ll get a clear action plan with 5 simple steps you can start implementing today, plus a bunch of shortcuts I had to figure the hard way. And: the things no one talks about but every new Substacker needs to hear.

It’s long. Intentionally. It will walk you from the stage of a total beginner to the advanced level of growth and monetization.

Save it. Bookmark it. Come back to it. Use the section you need right now and ignore the rest until you’re ready.

Before we start, I’m curious:

Because this is kinda long, here’s a table of contents:

This Substack playbook contains:

1. What is Substack, and how does it work?

2. The business model - how you make money on Substack?

3. Part 0 - Decide if this is a business or a hobby (stop here if it’s a hobby)

4. Part 1 - Set up for a high conversion rate

5. Part 2 - What to write

6. Part 3 - How to grow on Substack

7. Part 4 - How to monetize

8. Part 5 - How to automate and scale

9. The things nobody tells you (but you need to hear before you go all in)

10. The real secret that makes or breaks your Substack game

Hint: read this on a desktop and click on the right side to use the Substack automatic navigation - you can jump between sections easily:

Ok, now let’s deep dive!

Before the actual playbook, let’s get the basics fixed.

I’ve compiled everything I wish someone told me when I started. Because of this I wasted months in the learning curve which you can now skip.

So here it is…

What is Substack, and how does it work?

Substack is an all-in-one publishing platform - you can publish long-form posts, short-form posts called Notes (the social media of Substack), podcasts, video, and chat threads.

You have a personal profile and from it you can run multiple newsletters called “publications”.

You can host a free publication, a paid one, or both. You can build a community, run live events, and integrate digital products, sponsorships, affiliates and other revenue streams.

You can also collaborate with other Substackers, which helps you grow even faster.

The simplest way to think about it: it’s a blog, an email list, and a social network that helps you create real community - a place where we all talk to each other, create meaningful connections that can grow into friendships and partnerships.

The Substack community is the most authentic one. The conversations here feel natural, human, and deep. Not transactional like on X or LinkedIn.

And the content is of the best quality I’ve ever found.

Subscribers vs followers — and why it matters

This is one of the first things that confuses new writers, so let me clear it up.

Subscribers are people who give you their email address. They receive your posts directly in their inbox. This is the relationship that has real value - you own it, and it survives any algorithm change.

Followers are people who follow you on Substack’s social layer (Notes, the app feed) without giving you their email. They can see your Notes and your posts in their feed on the app. Much like social media, they can interact with your profile, but they don’t get your posts unless they subscribe.

The goal is to convert followers into subscribers. Email is the real asset.

How?

By using Notes, engaging with them, and collaborating with them. More about this below.

Types of content you can create

• Notes - short-form posts, like tweets - can be text, image, carousel, video, you can also add links. They live in the Substack feed and are your primary discovery tool. Your subscribers and followers will see them first. If they get engagement, Substack will distribute them outside of your “bubble”. Unlike social media, people can directly subscribe to you, giving you their email address, not just follow you. Substack makes it easer to subscribe than to follow, intentionally. The entire platform is designed to help you grow.

• Posts - long-form articles delivered by email and hosted on your Substack page. The core product. You can publish them without sending them as emails, or you can publish and send to your subscribers’ inboxes. Posts also get distributed in the feed like Notes, so your followers will also see them, but only in the app, not on their inboxes.

• Video - video posts - you can upload, embed or even record natively on Substack.

• Audio - you can add your own audio recording of your article, as well as run a full-blown podcast - upload audio episodes, host them natively on Substack, and connect them with Spotify, YouTube, Apple.

• Live - you can go live - alone or with someone else. Your subscribers get notifications and can interact with you in the chat. You can then publish the recording like a video, with thumbnails and multiple short videos automatically generated out of the recording.

• Chat - a community thread feature, like a group chat for your subscribers.

• Emails - you can send emails to your entire subscriber base or a segment of it using predefined filters. These emails are not published on the platform.

The paywall can be placed all across these multiple types of content, so that you can create a powerful paid subscription.

You don’t need to use all of them. Most successful newsletters run on posts + Notes, and add the rest only when it makes sense.

Hint: if you plan to offer coaching services, showing your face on camera helps. A lot.

Features of the platform that help you grow

• Recommendations - a native feature to recommend other publications to your new subscribers (and receive recommendations in return).

• Referral program - an automated way to reward people who help spread the word about your Substack. Rewards are based on the number of free subscriptions you get from someone.

• Gift subscriptions - when someone becomes a paid subscriber, they get 3 gifts with a 1-month paid membership to give to people who they know might be interested in your Substack.

• Pledges - in case you’re not ready to enable paid subscription, you can enable pledges - a way for people to “promise” they will pay you when you enable the payments.

• Promotions - you can use trials and multiple discounts to help sell your Substack more.

• Automated upsells - your most active free subscribers will get an automated email with a special offer you predefine.

• Drip campaigns - an automated sequence of emails for your free subscribers, paid subscribers, founding members, or people who decided to stop paying you so you can try to win them back. These campaigns are meant to replace the welcome emails in the future. For now they are in beta and only available to bestsellers.

• Collaborations

  • Cross-posting - you can cross-post a post you like and decide if you also want to send it to your subscribers’ inboxes.

  • Guest-posting - you can contribute to another publication when you write a post for it or a snippet that can be added into a post written by multiple writers.

  • Mentioning (a.k.a. shout out, or tag) - you can mention other Substackers and their publications.

  • Affiliate - you can collab with other Substackers by promoting each others offers using affiliate links (you can simply share your affiliate links from Amazon and other sources).

• Custom domains - you can move your newsletter to a custom domain for a one-time fee of $50. Worth considering if you intend to promote it on social media.

There are tons of others not so important things you’ll see in the settings, but those are the most vital ones you need to know and learn how to use.

Badges on Substack

There are three tiers of bestsellers, based on the number of paid subscribers they have. You can hide your badge if you want to.

There are also petal badges, indicating whether you pay for other newsletters. You can also manage the visibility of those on your profile.

How Substack works?

You have two options - you run a hobby, or you run a business. If it is a hobby, don’t ask me for advice, you can do whatever you like.

But if you run a business, you need to focus on three engines:

• free subscribers growth - new fresh leads. Post Notes, engage with others, grow your recommendations network, collaborate with other Substackers.

• paid subscribers / buyers growth - new sales. Simply said, you need to promote your paid tier. Yes, you sell. This is a business. Businesses sell to survive (and thrive).

• paid subscriber / buyers retention - retain existing sales. You need to build the relationship with your paid members and the value you deliver to their inboxes after they subscribe, so that they stay.

More on these below.

The business model - how you make money on Substack?

Substack existence heavily depends on people who run it like a business. There are no paid ads, just revenue share from what you earn from your paid subscriptions.

But you can monetize in multiple other ways. I’ve built an entire business around it, and the paid subscription is only 20% to 30% of my monthly revenue (you can see my breakdown here).

How you make money

There are several ways to monetize on Substack, but here’s a list of the most viable options:

• Paid subscriptions — readers pay a monthly or annual fee to access your paid content. This is the core model.

• Founding Member tier subscriptions — a higher-priced tier for your most committed readers. You set the price and define the benefits that come on top of the standard paid membership. The price is only annual.

• Digital products — sell one-time products directly to your audience (guides, templates, courses). You have to host them elsewhere, as Substack doesn’t have one-time payments. I use Gumroad and Teachable.

• Paid sponsorships — you can publish sponsored content and get paid for this. Usually works when you reach 5k subs and beyond. I use passionfroot to find sponsors.

• Affiliate partnerships — promote relevant products of other Substackers or Amazon, or else. Your subscribers click, buy, you earn commission.

• Coaching, consulting, done for you services — use your newsletter as the top of a funnel that leads to 1:1 work and clients to your high ticket services.

Is Substack Free?

Yes, Substack is free. You pay nothing to start your newsletter.

It’s has a win-win business model.

Substack takes 10% from your paid subscription revenue. On top of that, Stripe (the payment processor) takes approximately 2.9% + $0.30 per transaction.

So on a $100 annual subscription, you keep roughly $87 after both cuts.

There is no monthly platform fee for free publications. You only pay when you earn from Substack native subscriptions.

Substack doesn’t charge for any additional monetization activities you incorporate in your newsletter.

Basically, if you run a free newsletter monetized with coaching and courses, it’s free of charge. There’s no other platform that does that!

Important: Substack payments run exclusively through Stripe. If Stripe is not available in your country, or if you have issues with Stripe’s verification process, you cannot receive paid subscriptions. This is a real limitation — check Stripe availability in your region before you build your entire business model around paid subscriptions.

Ok, so now let’s move to the actual business.

Part 0 - Decide if this is a business or a hobby (stop here if it’s a hobby)

Most people skip this step and I believe that’s exactly the reason most people fail.

Here’s what happens:

Someone gets inspired, signs up for Substack, picks a topic they love, and starts publishing. Three months later they have 60 subscribers, no income, and a creeping suspicion that they’re doing something wrong.

They’re not doing anything wrong. They just built the house before they drew the blueprint.

So before you touch your profile, your bio, your first post, or your posting schedule you need to answer one question honestly.

Is this a business or a hobby?

Both are valid. But they require completely different approaches. And mixing them up is how you end up frustrated, underpaid, and writing into a void.

If it’s a hobby - write freely, post when you feel like it, don’t stress the numbers. Substack is a beautiful place for that. You’ll connect with amazing people, make some friends, and probably also make a few bucks.

And honestly, you can stop here, no need to go further with this playbook. Because if there’s one thing I can do best, it’s to help people build a business that converts.

But if it’s a business, you’ve got a 3-step simple strategy exercise next. Here it goes:

Step 1: Define the problem you solve

Not your passion. Not your niche. The problem.

The writers who monetize successfully on Substack aren’t necessarily the ones who write about what they love. They’re the ones who write about what they can do best (like I do). The ones who write for someone who has a specific, recurring problem, and who position their newsletter as the solution to that problem.

The question isn’t “what do I want to write about?”

It’s: who has a problem I’ve already solved, and what would they pay to understand how I did it?

Get that answer before you write a single word. Everything else - your name, your content pillars, your free vs. paid split, your pricing - comes after it.

Shortcut: Write this in one sentence: “I help people achieve [specific outcome] without [specific frustration].” If you can’t finish that sentence, you’re not ready to set up your profile yet. Stay here until you can.

For a paid newsletter, the problem doesn’t have to be huge. It just has to be real and recurring. Then make your solution difficult or impossible to replicate - that’s how you stand out. I’ve mapped exactly how I did it here:

Step 2: Build your paid tier

This is the part of my philosophy that surprises people most.

Most writers think the sequence goes: write → grow → monetize.

My sequence was different: monetize → write → grow. And that’s how I managed to build a full-time income on the side of my 9-5.

Here’s what I mean.

If you wait until you have an audience to figure out what you’re selling, you risk building the wrong audience. You attract readers based on your free content, and if your free content isn’t pointing toward a clear paid offering or isn’t connected to what you plan to sell in the future, you’ll convert almost none of them when the time comes.

The paid tier isn’t something you add later when you’re “ready.” It’s the destination you design the entire publication around from day one.

When I launched my Substack I enabled the paid tier immediately. And I got 3 annual paid subscribers on the spot.

Tip: You don’t need to have the product fully built before you launch. You need to know what it is. Even a rough answer like “I’ll a deeper strategic frameworks and templates to help people solve [this specific problem]”

You can build your paid tier in public - one post at a time. Actually, that’s how authors write and monetize their book - chapter by chapter.

Step 3: Choose your monetization model before you set up a single thing

There are two fundamentally different ways to run a Substack. They look similar from the outside but they require completely different setups.

Model A: Substack as the product. Your paid subscription is the business. Readers pay for access to your content - deeper frameworks, templates, research, analysis, community. Everything you publish either attracts subscribers (free) or converts them them to paid. This is the model I run.

Model B: Substack as the funnel. Your newsletter is free. The business lives behind it - courses, coaching, products, services. Substack is how people discover you and learn to trust you. You monetize off-platform.

Neither model is better. But they produce completely different editorial strategies, content ratios, posting frequencies, and growth priorities.

If you don’t know which model you’re running, you’ll make decisions that contradict each other. You’ll write free content that undercuts your paid tier, or you’ll push paid subscriptions when your readers actually want to hire you for a high ticket service.

Decide this now. Then set up everything else.

The order of operations

This is the sequence that actually works — based on what I’ve seen across hundreds of writers and what I’ve built myself:

1. Define the problem you solve. No need to define the person who has it

2. Choose your model - Substack as the product, or Substack as the funnel

3. Design your paid tier or core offer - at least in outline

4. Set up your publication to reflect that positioning

5. Write free content that attracts the right reader and points toward the paid layer

6. Write paid content to convert free subscribers to paid (skip if you run a free newsletter)

7. Promote. Promote. Promote. In both cases you have to sell. And it’s best to sell without actually selling.

Most people start at step 4. Some start at step 5. Almost nobody starts at step 1.

That’s the gap. And it’s the reason two writers can publish on the same topic, with similar quality, for the same amount of time — and get completely different results.

Now. With that in place, let’s build your high-converting Substack.

Part 1 - Set up for a high conversion rate

I sell (without selling) at every possible place I can, that’s partially how I keep a high conversion rate (the rest is automated - more below).

Here’s a list of the most important elements you need to clearly communicate your paid tier, product or service.

Your publication name isn’t just branding

Here’s the mistake I see constantly.

Writers name their newsletter something vague and poetic, then spend the next year trying to explain what it’s actually about.

“Wandering Thoughts.” “The Weekly Pulse.” “Scattered Notes.”

Or just put their name on it.

Fine if you’re in the hobby scenario. Terrible at converting readers into subscribers.

Especially if you want to build a business.

I named mine “Unplugged” because I write about AI and automations, helping people unplug themselves from the grind and plug AI into work. And also because it’s the raw version of who I am, as Substack is the only place I can write like that.

Make your name point the problem you solve, even if it’s indirect (like in my case).

Test your name before you commit. Say it out loud to 3 people who don’t know you and ask: “What would you expect this newsletter to be about?” If they can’t guess, rethink it. This takes 10 minutes and saves months of confusion.

Tip: Your publication name and your Substack URL are two different things. You can change the name later. You change the URL without breaking every link you’ve ever shared only once. Choose it carefully.

Your profile, bio, and about page

Most writers treat these like an info pannel. They’re not.

They’re sales pages.

Lead with the reader’s problem, not your CV.

Nobody lands on your about page thinking “I wonder who this person is.” They’re thinking “what’s in it for me?” Answer that question in the first two sentences.

Tip: Write your publication description in second person first: “If you’re trying to [achieve outcome] without [frustration], you’re in the right place.” Then introduce yourself. The reader always comes before you do.

Write your bio for them - say how you help them first, then say who you are. Your bio shows up everywhere - search results, Recommendations, your profile card. It has to work out of context, without the rest of your page around it. Write it like a standalone pitch, not a chapter of your memoir.

Use a photo that looks like a real human, not a LinkedIn headshot. Substack is personal. People follow and subscribe to people they feel they know. A warm, real photo does more work than any credential.

If you don’t want to show your face or tell your real name go with a pen name, but make sure your profile picture looks human.

When I started I wanted to keep my profile secret, separated from my day job. So I published a photo where I wear sunglasses and my face is barely visible - people couldn’t tell it’s me. It’s a way to approach this.

Make your about page for them, not for you. I talk about what’s inside and why tey should upgrade immediately.

The welcome email

Your welcome email is statistically the most-opened email you will ever send. Open rates of 50–80% are completely normal. Some writers hit 90%.

Here’s something most new writers don’t know: it’s also the one with the highest conversion rates.

And most people send two sentences. Or keep Substack defaults.

Set expectations + make them feel something in the first 3 lines. Then pitch your paid tier - give them a reason to upgrade on the spot.

More than 20% of my paid subscribers upgraded on day 1. Make your first email count.

Tip: Ask a question at the end of the welcome email. A real one, not a formality. Replies train Gmail to put you in Primary, not Promotions. This matters more than most people realize.

Your pinned post

This is the highest converting post I have.

Your pinned post is prime real estate.

Most writers waste it on a welcome note nobody reads twice. I pin a “Start Here” guide that links to my top paid pieces with a soft nudge to upgrade explaining what they miss if they don’t

Hint: The most common mistake I’ve seen during my reviews: inconsistent messaging across all of the above places. Use the same wording when you communicate your benefits. Most people need to hear the same thing multiple times before they buy. It’s how you build trust. It’s how you create what I call “confirmation moments” - small steps that move a reader to a become a buyer.

Part 2 - What to write

The blank page problem is actually a positioning problem. When you nail positioning, you’ll never run out of ideas to write about.

The one question that solves “what do I write about” forever

Most writers approach this as a content question.

It’s not. It’s a positioning question.

The best newsletters aren’t written by people with the most credentials. They’re written by people who figured something out the hard way and are honest about what that looked like.

Tip: The best content angle sits at the intersection of three things - what you know deeply, what people keep asking you about, and what you’d write even if no one read it. If all three overlap, you’ve found your lane.

Go into your sent emails, your DMs, your comments right now. The questions people ask you unprompted are your editorial calendar. Write those answers first.

Content pillars

If your newsletter covers more than 3 topics, it covers nothing.

Readers can’t recommend what they can’t describe in one sentence. And recommendation is big part of how any Substack grows.

Tip: Name your pillars like columns or frameworks. Not “personal growth” — “The Anti-Hustle Files.” I named one of mine “Write2Sell” not “marketing tips”. A named column becomes a brand inside your brand. It increases the perceived value of your offer.

Rotate your pillars in a predictable sequence. Readers form habits. When Tuesday feels like “data breakdown day,” they show up for it.

Free vs paid content

Free posts attract. Paid posts convert and retain.

Honestly, I thought paid post need to be more, but when you have a good positioning and when you write about the product you solve and point to at least one of your offers in every post, even free posts will do the heavy (sales) lifting.

My latest analysis showed I have a ratio of about 50/50.

Post formats that work

Long-form essays. Personal stories with a lesson baked in. Data breakdowns using your own numbers. How-to frameworks. Hot takes. Interviews. Behind-the-scenes posts. Curated round-ups.

The top 3 posts that worked really well for me so far:

• Analysis post - where I deliver the outcomes of my latest analysis with AI

• Case study posts - where I showcase how I (or someone else) achieved a great result

• Tangible asset drop - where I explain how to use my latest AI tool, give an AI prompt or some

I also see good performance of the hot take type - a contrarian opinion, argued thoroughly, the interview type - a live with a recording published later, and the behind the scenes - where I share how I built stuff.

The community is a big growth driver. Start your chat, runs some challenges, do a community live call. Connect with your audience - that’s how you maintain high retention rates.

On video: I know video is uncomfortable for most people but on Substack you can be who you are. This is not YouTube. You don’t need to be polished. Just go live, share the recording, see what people say about it. It’s the fastest way to build trust.

How often to post

Here’s the honest answer.

The more you post, the more you’ll earn.

Now, I know this is not something most people like, but it’s what data shows me. It’s proven industry standard.

Do you need to publish on the same day and time every week? Not so much, I thrive in chaos.

Gurus say readers form habits, so you have to pick a day, tell your subscribers, then protect it like it’s a meeting with a very important client. But the one thing I can confirm is that Tuesdays and Wednesdays are the best time to send emails.

Everything else is noise.

As for Notes - I do about 10 per day. Substack recommends 3 to 5, and I also know people who do really great with about 3 per day.

It’s all about the content.

I’ve built a custom GPT that writes viral Notes - brought hundreds of subscribers to me and my most committed paid members. I use it to solve the Notes daily task in just 15 minutes.

Tip: Schedule posts in advance. Substack lets you queue them. Write on weekends, schedule for Tuesday. Batch your Notes on Sunday for the week. Your readers don’t need to know your process, they just need to see you show up.

Your first 10 posts

Don’t start with whatever feels easiest. Start with what builds the fastest trust.

• Post 1: Your origin story - why this newsletter, why now, why you specifically

• Post 2: Your strongest contrarian take in your niche

• Post 3: A personal failure and what you learned (vulnerability builds loyalty faster than expertise)

• Post 4: A data-backed breakdown of something your readers care about

• Post 5: A “how I actually do X” behind-the-scenes

• Post 6: The answer to the most common question you get asked

• Post 7: A curated resource list (easy to write, high shareability)

• Post 8: A hot take - one hill you’ll die on and why

• Post 9: A reader story, case study, or interview

• Post 10: Your contrarian take - what you believe about your niche that most people get wrong

Tip: Don’t wait until post 10 to have a point of view. Have one in post 1. Opinions attract subscribers faster than information. Information is everywhere. A specific perspective you can stand behind is rare.

Tip: Cross-link your first 10 posts to each other as you go. Build the web early. New subscribers binge. Make that binge as deep and interconnected as possible.

The most common mistake I see: people try to get others to like them, so they aim to be rounded, polished and ultimately boring. Or they overuse AI. Here’s the essence of how I actually write - you don’t need to know anything else:

Part 3 - How to grow on Substack

Growth isn’t random or viral. It’s actually better not to go viral - the quality of the subscribers you can get with consistent growth is much better than a viral spike.

With a newsletter business, you have three core engines you need to move together:

1. Convert readers to free subscribers

2. Convert free subscribers to buyers (paid subscription, product or service)

3. Retain buyers so that your business grows

Once you get that done, you’re ready to scale.

Substack’s built-in growth engine

This is the most underused, highest-ROI growth mechanism on the platform.

When someone new subscribes to any Substack, the platform shows them a list of recommended publications. If you’re in those Recommendations, you get passive subscriber growth around the clock — without publishing a single additional post.

Go to your Substack dashboard → Grow → Recommendations. Recommend someone you love. Substack will send them an email notification asking them to recommend you back.

When you recommend someone, tell them. It opens a natural conversation. Conversations turn into collaborations.

You don’t need 10K subscribers to start getting Recommendations. You need one writer with an overlapping audience who trusts you enough to recommend you. Start there.

Notes - the most underused tool on the platform

Most writers treat Notes like a social media feed they’re supposed to post on.

That’s not what it is.

Notes is a powerful discovery engine. When you post a Note, it surfaces to people who don’t follow you yet, through the people who do. It’s the closest thing to organic reach Substack has ever offered. Yes, it looks like social media, even Substack calls it like that now.

But unlike social media, it is more a conversation starter. A connection invite. An extension of your post.

The core difference: Substack algorithm works to get you subscribers, not followers. There is a one click “subscribe” button next to your Note.

Subscribe. Not Follow.

It’s social media done right.

In the comments, you’ll see real discussions, not just one-word comments aiming to get an automated DM with some kind of freebie.

My first Note that genuinely took off and went viral was a story about my mom. Because of it I quickly learned that viral is good, but consistent growth is better. The quality of the subscribers is much higher.

The Notes that get reshared have one thing in common — they make the reader feel seen. Not impressed by you. Seen by you. Write for recognition, not admiration. “I felt this” beats “wow” every time.

I frequently get comments of the sort “I needed to hear this today, thank you Yana”

Respond to every comment on your Notes. I often get a bunch of new subscribers after I respond all of my comments. I try to do that daily, but sometimes because of my job I do it in the weekend.

Repost other people’s Notes with a meaningful comment added. Not “great point!”, but a genuine extension of the idea.

Screenshot your best data and post it as an image Note. Numbers stop the scroll every single time.

Batch your Notes. Write 7 in one sitting on Sunday. Save as drafts or schedule them. You don’t need to be on the platform daily, you just need to appear to be.

Cross-promotion and collaborations

One deep collaboration beats ten shallow ones.

The easiest collab format is to write one section of each other’s newsletter on a shared topic. Low lift, genuine value, new audience exposure. Neither of you is doing extra work, you’re redistributing it.

Co-host a one-time free event, a live conversation, a shared challenge, a joint thread. Events create urgency. Urgency drives sign-ups from people who were sitting on the fence.

Create partnerships for continuous collaboration with people who fit your business and audience. Even of you see them as your competitors. This is help you both get more exposure to external audience.

Here’s how I got 8 new subscribers from a single live:

Growing from outside Substack

Pick one external channel, master it, then funnel it. It does’t have to be social media, can be Medium or some kind of a community where you’re active.

It you don’t have any, stay with Substack and go all in.

I decided to try growing on social media with automations and paid ads. I don’t want to invest any effort in organic growth as it requires a lot of time which I don’t have because if my 9-5.

But some social media are way much bigger than Substack (like facebook and YouTube), so it’s still a good way to grow faster when you leverage your presence there.

YouTube is integrated with Substack, so you can post your videos automatically on your YouTube channel. Just make sure you optimize it so that it’s distributed well on the platform. I got a coaching client from my channel, and all I do is to report my lives and spotlights there - videos I already do for Substack.

LinkedIn is the most underrated feeder channel for Substack right now — especially if your audience is in the professional field. One post that lands well on LinkedIn can bring in 200+ subscribers overnight.

Add your Substack link to every email signature, every bio, every platform you’re already on. This is free growth you’re leaving behind every single day if you don’t do it.

If you’re on Medium, link to your Substack at the end of every post. Medium readers are already newsletter-shaped. They convert at a higher rate than most other traffic sources. I get free and paid subscribers frequently and my conversion rate is about 20%!

SEO & AI SEO

Write 1 evergreen pillar post per month targeting real search terms and let them work while you sleep. I’m getting traffic, subscribers and coaching clients from Google, ChatGPT and Claude.

Use your primary keyword in the first 100 words, in at least one H2 subheading, and in your preview text. That’s 80% of on-page SEO done in 5 minutes.

Make sure your images have proper file names and alt texts.

Substack’s preview text field is your Google meta description. Most writers leave it blank. Write 150 characters that include your keyword and a reason to click. Don’t waste it.

Part 4 - How to monetize

People will pay. You just have to make it easy, obvious and no brainer.

Paid or Free newsletter

Even if free newsletters feel easier, there’s a list of pros and cons you should know before you decide:

Free Newsletters - Why Choose Free?

1. Simple & Easy: Free newsletters are straightforward. You write, grow your audience, and build trust.

2. Monetize from day 1: Even without a paywall, you can monetize right away through:

   • Selling digital products (like courses and ebooks)

   • Affiliate marketing

   • Sponsorships

3. Faster growth: Free posts tend to viral - it helps you grow faster on Substack, especially if you’re active on Substack Notes (the social media of Substack). And if you have a solid portfolio of offers, you can easily grow to 6 figures in just a few months.

The Downsides:

• Needs constant creation of new offers on top of your content: Selling the same digital product to the same subscriber is impossible. You need to build a new offer (ideally) every month to maintain a 6 figure revenue and grow from there.

• More sales skills required: You’ll need strong marketing and especially copywriting skills to continuously sell digital products. And there’s the additional effort required in building the digital products, setting the landing pages and building the sales funnels.

• Against Substack’s business model: Substack thrives on paid subscriptions, so there’s always a risk they might limit free content distribution in the future (just a hunch, no data to prove that).

Paid Newsletters - Why Choose Paid?

1. Aligned with Substack’s model: Substack’s tools are designed to support paid subscriptions, and the platform prioritizes features that help you grow a paying audience. It’s the best place to grow a paid newsletter, because Substack specializes ONLY in that business model, so the tools and features are state-of-the-art. Substack literally helps you sell more subscriptions.

2. Your content Is the offer: With paid newsletters, your content itself becomes the product. You don’t need to constantly create new offers—you can even build digital products in public, one piece at a time. You can write a book or build a course chapter by chapter and paywall it.

3. Low pressure - you can build your catalogue in public, no need to create products upfront.

4. Long-term income: Paid newsletters compound over time. With each new subscriber, your recurring revenue grows.

The Downsides:

• More Complex: Running a paid newsletter is running a business. But not any kind of business, it’s a subscription business. One of the most complex business models. Yet, one of the sweetest and most lucrative ones because of the faulty belief people will continue to pay indefinitely. You’ll need to keep providing tangible benefits to your subscribers (e.g., tools, guides, case studies). And you need to retain them (no need when you sell one-time offers). You need to build relationships.

• Takes Time: Paid newsletters don’t scale overnight. You’ll need patience to see the compound effect. You don’t get to the 6 figures fast, but rather steadily.

So, What’s the Best Approach?

For me - both are demanding, you have to choose your poison, or do both. That’s how you get the best of both worlds.

When to turn paid on

Let me save you the debate.

Immediately. And make sure you have at least 3-5 posts from your paywalled content already published before you launch your Substack.

When your content consistently delivers one clear, specific outcome to one specific type of reader.

“Ready” is a feeling. It never arrives. Turn paid on when your content is consistent and your positioning is clear, not when you hit an arbitrary number. Positioning without a big number still converts. A big number without positioning doesn’t.

And if you want to grow your audience first, without any clear vision about how you’ll monetize, you’ll probably find out that you have built the wrong audience.

It happens so often.

That’s why I built the SUBSTACK QUEST - it’s the exact model you need to follow, step by step, to build and launch a high-converting Substack.

Pricing and what actually converts

Annual plans convert better than monthly, and most writers don’t push them nearly hard enough. My share is more than 90% annual.

Make it feel like a no brainer.

For an annual I’d stay below $50 and I’d increase the monthly so that there’s zero rationale to buy it. That converts, but only if you nail the positioning and build a killer offer, one that sells itself.

Now there’s one thing most people avoid telling you and I had to learn it the hard way:

You have to promote your paid membership, product or service all of the time. At any place possible. Or it won’t sell.

Most people think it’s enough to publish one post about it.

It’s not.

Because who’s gonna buy it if no one knows about it?

Here’s how to write your posts so that your offers sell themselves:

The post-subscription experience

This is where most writers completely drop the ball.

According to the state of newsletters report from Beehiiv, over 80% of independent newsletters aren’t using any automation beyond a basic welcome email. That’s a huge opportunity cost.

My data shows that 71% of my paid subscribers converted within the first 30 days after subscribing. If you don’t do anything within this window, you’re leaving money on the table.

Run a welcome sequence, deliver value, build trust, then pitch your offer.

Substack has native automations, but at the time of writing this they’re still available only to bestsellers. Even though I can use them now, I still run my automations in Kit, just because I have complete functionality.

Here’s how I set my welcome sequence that sells my paid subscription so that I don’t have to promote. It alone brought me more than 150 paid subscribers so far.

Retention is the name of the game of the paid subscriptions. Make sure you have a quality service or your paid subscribers will churn.

I can’t stop repeating this. It’s the core of any subscription business and I know it not only from Substack - from my 15+ years in product sales and marketing of paid subscriptions for consumers and businesses, generating billions per year.

My retention is quite good on Substack because I know this:

Simply said: take care of your people.

How to paywall and send emails

One of the main reasons why I have a high conversion rate is that I send every email to all subscribers. Yes, even the paywalled ones.

My way of paywalling delivers a lot of value for free and keeps only the tangible stuff paid. So when my free subscribers receive a paid post they don’t unsubscribe.

Here’s what I do:

• Keep the WHY and the WHAT for free

• Add some proof it works

• Add some results it delivers

• Keep the HOW to implement it paid

That’s my conversion engine in a nutshell.

Beyond subscriptions

Once you have a consistent paid subscribers growth, its’ time to build more income streams.

I now run a $5k-$10k a month newsletter, but the paid subscription is merely about 30% of it.

Digital products. Courses. Templates. 1:1 coaching. Affiliate partnerships.

I use my paid subscription to validate a potential new product, here’s the workflow:

1. Write a paid post about the core problem and it’s solution

2. If it resonates, if it brings new paid subscribers, then you’re on to something

3. Expand it into a product out of it and sell it to your entire subscriber list. Paid members can have a discount.

Buyers will buy again. That’s why is so important to retain them. Make sure you have a quality paid service and also have offers for your paid subscribers so that your business grows.

Affiliate partnerships work on Substack when the product is genuinely relevant. One authentic mention in a high-traffic free post can generate meaningful income with zero extra content creation.

Part 5 - How to automate and scale

Two hours a day. That’s all this takes for me now, but only because I stopped doing it the hard way.

When I started it used to take me almost a day to write a paid post. And a couple of hours to come up with a good Note.

Writing is a muscle, you have to train it every day. It gets easier with time.

But I also added my minions into the game - my AI agents that help me stay sane along with my 9-5, and still have some quality time with my partner, my dog and our friends and families.

I have a GPT that writes highly engaging Notes for me, designed to bring me subscribers.

I have one GPT that writes long form, one for CTAs and one for Titles and subtitles.

They’re all available to my paid members because this is what I do on Substack - test, prove, enable for my people to help them speed up growth.

AI without sounding like a robot

The writers who will be unbeatable in the next 3 years aren’t the ones who refuse to use AI or the ones who outsource their voice to it. They’re the ones who use it to think faster and edit cleaner, while keeping every word unmistakably theirs.

Read your AI-assisted draft out loud. If you stumble, your reader will too. If it sounds like a LinkedIn thought leader wrote it, rewrite it.

Use AI to generate your first outline, not your first draft. The structure is the hard part. The voice is yours, and no prompt can replicate the specific way you see the world.

Build a custom AI skill with your voice, your frameworks, and your editorial standards. A generic prompt gives you generic output. A voice-encoded skill gives you a first draft that sounds like you wrote it on a good day. Here’s how I do this:

Repurposing

Of course you can repeat yourself. One idea shouldn’t live in one place. Actually people need to hear it more than once before they make a decision.

One long-form post can become: an email broadcast, 3–5 Notes, a LinkedIn post, a video script, and a short-form clip. Same thinking. Five formats. Five audience touchpoints.

Tip: Your best Notes often started as a paragraph in a long-form post you almost deleted. Mine your drafts. The throwaway lines are sometimes your best standalone ideas.

Automations

Substack doesn’t have an official APIs which is one of the heavy burdens for someone who love automations. But this is how Substack maintains authenticity and quality of the content, and they’re serious about it.

Make sure you read the content guidelines before you think about anything automated.

Besides the welcome email sequence I shared above, I also have an automated webinar that sells my digital products - this converts and 10%, brings me another 30% of my monthly revenue, and I do nothing about it.

I’ve automated my social media post entirely and I don’t expect anything since I don’t engage but I do get subscribers.

And I’m just starting.

Automate anything that can be outsourced to a machine, but make sure you keep the quality high and you don’t risk your account.

Because time is our most valuable resource.

How to scale

Scaling isn’t doing more. It’s doing the right things more often.

The 4 metrics that actually matter

I make data driven decisions. That’s how I scale.

I know most people hate data, but it holds the answers to all of your growth pains.

Just look at what resonates, what works, what doesn’t and double down on that.

The data and the metrics that matter most:

1. New subscribers growth & sources

2. Free to paid conversion rates

3. Paid subscribers NPS

4. Paid subscribers retention rates

NPS is the early signal you should track to understand how your paid membership is doing. The good thing is Substack has the survey feature we can use to measure it. I’ve created a template that calculates it automatically here:

I don’t care that much about open rates, click rates and engagement. It is a signal when I decide what to create next, but it’s not so relevant to judge whether my business is growing or declining.

The above four are.

Tip: Conversion rate below 3%? Positioning problem. Retention rate below 50%? Product & customer service problem. New subscribers growth less than 5-10/day? Discoverability problem. NPS below 60? Future retention problem. Every metric tells a different story.

The things nobody tells you (but you need to hear before you go all in)

Ok, now here comes the tricky part.

This is my brutally honest take on Substack for the 2 years I’m on the platform.

I firmly believe Substack is the place to be right now if you want to grow a sustainable business online. Still there are few things to have in mind before you go all in.

This post would be dishonest without this section. So here’s what I’ve actually run into, and what you should know before you go all in.

Platform limitations

The all so many notifications bring deliverability problem. Substack sends a lot of notifications. Every Note, every comment, every recommendation, tons of it. Readers get notification fatigue and start ignoring them. Some disable them.

The app has an option to disable all email notifications and read everything in the app. This prevents you from receiving emails from people you subscribed to.

It’s a real deliverability problem which can impact your conversion rates. Especially with the way I promote my paid subscription (as described in the paywalling part above).

For comparison: my deliverability on Substack is about 95% and 100% on Kit. It’s not a big deal, but it exists.

The sales tax nightmare. If you have paid subscribers in the US, sales tax obligations vary by state. Substack doesn’t handle this for you the way other platforms like Teachable, Gumroad and Kit do.

As you scale, this becomes a real compliance question. Talk to an accountant before you hit significant revenue.

I handle this using Stripe tax and some US based services.

The failed payments problem. Stripe’s dunning system (the process for chasing failed subscription payments) is not very sophisticated. Failed payments happen more than you’d expect, and the recovery rate isn’t always great.

Some subscribers lose access without realizing it, some churn accidentally. It’s a leaky bucket you have to monitor closely and fix manually. You’ll face this once your paid subscribers start to renew their subscriptions.

No personalization, tagging, segmentation, or real automation. You can’t tag subscribers by interest. You can’t send different emails to different segments. You can’t build complex automated flows. The sequence feature is very basic right now. If you’re used to proper email marketing tools like Kit or Mailchimp, the limitations here will frustrate you.

No landing page builder. You can forget about lead magnets. At least in the classical way. I have a page explaining that my lead magnet comes after subscribing but people get confused.

You can read the comments on my page:

Your Substack welcome page is your landing page, full stop. If you want a custom opt-in page with your own design and copy, you’re building it somewhere else and redirecting.

This limits my paid ads activities A LOT. I recently found a way to work around this is that I can get a decent cost per lead, bit’s not optimal. I raised this to Substack, other did too, but so far we have no feedback. It’s a basic feature most email platforms have. I mean, that’s BASICS.

The UX is still a work in progress. It’s a blog, but without submenus or proper navigation. Even with the recent update of the headers and footers, it’s still basic.

Posts in the app can’t be saved as drafts and continued on desktop, and there’s no workaround.

If you serialize video content, like a course, it’s not very convenient for the user to consume - no way to mark as completed or an easy way to move to the next video (we have such a button but it’s hidden at the bottom of the post).

The profile vs. publication distinction confuses new users constantly. Some features that feel like they should exist simply don’t.

In-app purchases on iOS are painful. Apple takes its ~30% cut on all in-app subscriptions. If a reader subscribes through the iPhone app rather than the web, your effective revenue per subscriber drops significantly.

You can decide whether you pay for this or you charge your subscriber on top. Both are a pain. All we can do is to disable in app purchases.

New features go to Bestsellers first. Substack rolls out features to bestselling publications before everyone else. That makes sense from a business perspective, but it means the playing field isn’t completely level when new growth tools launch.

Some features like welcome sequences (drip campaigns) can help people become bestsellers faster, but it is what it is.

It’s Substack’s way to incentives us to go paid. After all, it’s a business.

The analytics are a mess. There are no Notes analytics. No comprehensive subscribers analytics. We get only exports with detailed subscriber data. You can’t see what you need to see without exporting CSV files and doing the analysis yourself. I export and analyze with AI.

No way to track unsubscribed people over time — which could be a legal data compliance issue for some writers, depending on their jurisdiction. I enabled email subscription notifications, so at least I get every subscribe or unsubscribe event tracked on my email.

The chat features are limited. We can’t organize threads, set rules or easily moderate. And we can’t even edit DMs. It’s a very basic feature for now. I’m sure it will be improved in the future though. Substack is always improving, so this is me being patient.

No one-time payments. We get only recurring subscription payments. So no native way to sell one-time offers - we have to send people to external platforms. Gumroad is a good option, it’s free and also takes 10% - perfect for a beginner.

Honestly, I’d be less frustrated if I knew this in the beginning, but no one is perfect. Those are flaws I can live with and it’s still the best place to be right now.

The real secret that makes or breaks your Substack game

Even with all of this — the setup, the strategy, the systems, the tools — you’re still not set for success. It’s not granted.

The one thing that actually separates the writers who build something real from the ones who don’t is simpler and harder.

They stayed.

They stayed long enough to get good. Long enough to understand their reader. Long enough to stop writing for hypothetical subscribers and start writing for the real ones who showed up.

Substack is not a fast game. But it’s an incredibly fair one. The compounding is real. The relationships are real. The income is real.

I’ve been trying to make money online for years. Ever since 2010. And I succeeded with some initiatives, but nothing stayed with me more than an year. It just didn’t fit my demanding schedule.

Substack feels like home to me.

And none of it happened because I had some secret advantage.

It happened because I stayed in the room long enough to figure it out.

You can too.

Yana

P.S. If you want to take the fastest way possible, skip the learning curve and get to the earning part, check this page.

Kickstart Your Substack Growth:

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• Work with me to get your Substack up and growing

Save Tons of Time! Use My Custom GPTs:

• The Title Generator that gives me headlines that stop the scroll

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Or get the bundle with all the tools, now at a very special price ;)

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Wall of Love

If you’re serious about your Substack monetization, make this post your daily engagement routine. Share your posts, then read and join the conversation in the comments of the other members’ posts. This is how we grow!

If you’re not yet in the Writing Challenge, NOW IS the best time to join.

VIPs: You have new gifts👇

Here’s what you need to do now:

1. Add yourself to the Accountability tracker, so that you have a chance to win the award (a spotlight with me to get more exposure of your Substack)

2. Share a link to your posts in the comments below so that we can find it, read, comment, like, and share it!

3. Make this challenge for your daily engagement workflow - Check other people’s posts in the comments of this post. Find something you like to read more about and give it a like, comment and share - that’s how you grow faster (and you help others grow too).

Anyone from the Unplugged community can participate.

Let’s do this!!

Subscribe now

Share your link now 👇

P.S. If it doesn’t challenge you, it won’t change you. If you haven’t already, Join the Writing Challenge if you’re serious about growing on Substack.

P.S.S. If you’re not taking the Challenges, you can opt-out from receiving these weekly posts without unsubscribing for the rest of the content - do this from your settings here:

If you’re serious about your Substack growth, make this post your daily engagement routine. Share your Notes, then read and join the conversation in the comments of the other members’ Notes. It will help you and them grow.

Grab your Viral Notes Writer GPT & post some highly engaging Notes.

Notes are essential for your Substack growth. If you’re not yet in the Notes Challenge, NOW is the best time to join.

Here’s what you need to do now:

1. Add yourself to the Accountability tracker so that I consider you for the prizes.

2. Share a link to your Notes in the comments below so that we can find it, read, comment, like, and restock it!

3. Check other people’s Notes in the comments. Find something you like to read more about and give it a like, comment, and share. Make this challenge your daily engagement routine - it helps you, as well as the other members in the community, grow faster.

PLUS: if you have a Note with 100+ likes, DM me with a link, so that I can add it in the Unplugged Hall of Fame :)

You can share your Notes here throughout the whole week, until the next sharing post on Saturday.

Anyone from the Unplugged community can participate.

Subscribe now

Let’s do this!!

Share your link now 👇

P.S. If you haven’t already, Join the Notes30 Challenge if you’re serious about growing on Substack.

P.S.S. If you’re not taking the Notes Challenge, you can opt-out from receiving these weekly posts without unsubscribing for the rest of the content - do this from your settings here:

That’s why this Challenge is so important.

Alright! Let’s now announce the winners from the last month!

WINNERS AWARDS

First, I want to personally congratulate all of the members who took their growth seriously last month and were active:

, , , , , , , , , , , , , , , , , ,

Congrats to all of you! You’re ABSOLUTELY amazing!

Now, to select the winners, I have to see you in the Accountability tracker AND in the comment section of the weekly sharing posts, and since not all of you added yourselves to the tracker, I’m gonna honor that and select ONLY among the ones who did.

Ok, so the winner is….

….drumrolls please.…

Winner from last month Writing Challenge:

→ ←

BIG Congrats to Daniel !!! I can’t wait to jump into the session with him, and talk about all things Substack growth! Looking forward to it!

The Spotlight Session Award

→ #1 Award is a Spotlight Session to talk about your Substack and more. To give you and your Substack more exposure, I will share this session:

• all subscribers

• my YouTube channel

• my BiTES atomic newsletter

• my other social media accounts

→ Watch all previous spotlight sessions here.

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Time to kick off the ALL-NEW WRITING Challenge!

If you haven’t already, take my new data-driven online writing course to convert at higher rates and make your writing contagious:

And the all-new data-driven copywriting course to make your paid offer sell itself:

This new Challenge comes with a couple of my all-new Data-Driven Courses designed to help you sell (without selling). It’s short, it’s essential, and it’s zero fluff. For you, if you’re still struggling to “find your voice” or to get high-quality output from AI.

Why a Writing Challenge?

It’s clear: posts do get you new subscribers. And sales.

But it might be challenging to stay consistent.

And it’s often hard to find who or what to engage with to grow faster, especially when you search for a good read.

That’s why this challenge exists.

Within Unplugged, you have everything you need to grow your Substack:

• the monthly Notes30 Challenge where you grow your free subscribers,

• the weekly Write2Sell column where you convert them to paid and keep them paying,

• the Substack Quest to bring you to your first (or next) bestseller badge faster,

• the QUEST LABS with all the AI and automations, which helps you grow while you sleep, and…

• this monthly Writing Challenge where you apply the knowledge from the Write2Sell column and the Quest in practice and actually work to grow your paid subscribers,

• plus: the AI tools you can use to grow easier and faster (find the links below).

• and: the ALL-NEW Data-Driven Online Writing Course and the Data-Driven Copywriting Course to make your writing contagious + make sure it sells.

What is it?

It’s a challenge for writing.

But not just writing.

It’s built to help you convert more subscribers, applying everything from the Write2Sell column and the Quest in practice, and feed your automations with more sales. Because learning how to do things is nothing if you don’t take action.

So, in this challenge, we’ll take action.

The Challenge:

PARTICIPANTS:

UNPLUGGED PAID MEMBERS

As usual, Paid and V.I.P. members have their private access to the GPTs, and the Data-Driven Online Writing Course, the Data-Driven Copywriting Course with all templates, cheat sheets, formulas, checklists, data banks, and supporting materials.

What you need to do:

• Write and publish at least 1 post per week.

• Join the challenge by adding yourself to the Accountability tracker

• Make this challenge your daily engagement workflow: share your posts in the weekly thread (you can do that every day until the next post comes on Sunday), read, like and comment on other people’s posts - it helps them, AND YOU grow.

How to do that (faster)?

• Take the ALL-NEW Data-Driven, NLP-infused, Online Writing Course and the Data-Driven Copywriting Course to make your writing contagious, AND make sure it sells for you (without selling).

• Watch the Positioning, the Product, and the Content Strategies from the QUEST: to make sure your content matches your audience's needs.

• Use my custom GPT the CREATIVETECH Writer Pro (free for paid members - use the link below) for outlines. I give my GPT one of my notes and ask it to expand it into a 1000-word article. I then edit and post for free. It works.

• Make sure you add links to other posts, so that people keep reading (or start buying if they are paywalled - that’s what I did)

• Add a compelling headline, one that opens a curiosity gap. Use my custom GPT the TITLE Generator (link below) - give it your entire article and it will come up with 10 titles suggestions.

• Make sure you have a CTA at the end of your post, selling your product in a non-salesy way. How? Use my brand new custom GPT High Converting CTAs Writer (link below). Just give it the product description and it will generate you 10 non-salesy CTAs that convert. If you don’t have products to sell, become my affiliate and earn 30% from each sale. Apply here (I approve everyone).

• Make the weekly boost posts your daily engaging routine:

  • Share a quote from your post on Notes (select some shareable sentence & restack quote)

  • Share a link to it on the Weekly Writing Challenge Sharing post: I will publish one every Sunday - it will arrive in your inbox.

  • Read, like, comment and restack some of the other posts you like. Make this Challenge your daily engagement routine - it will help YOU and other Unplugged members grow faster.

• Track your consistency: add yourself to the Accountability Tracker. I have a Prize for the most active!

The GOAL?

Real CA$H!!

Sales is what I do best, and in this newsletter, I help you do it too, without the fear of failure or alienating our audience. It’s all in the Quest.

WINNERS AWARDS:

Spotlight Session with me to talk about you and your Substack.

Rules for the winners’ selection:

• I’ll select one of the most active participants in the Challenge based on the Accountability Tracker and your activity in the sharing posts. Rules:

  • 1. must be in the Accountability tracker and stay active in the weekly sharing posts

  • 2. must have completed the challenge (at least one post a week)

  • 3. you can win the same challenge more than once but in different months

  • 4. you can’t win both Writing and Notes challenges in the same month. If you do, I’ll invite the next most active person for a session

• Priority of selecting winners:

  • 1. most active among the VIP members

  • 2. most active among the annual paid members

  • 3. most active among the monthly paid members

• Announcement of the winners: start of next Challenge - 2nd day of next month

• When do we do the spotlight: during next month upon your availability. We’ll do the session only if you’re willing to. If not, I’ll invite the next most active member until I get a “yes”.

• How do we do the spotlight: over Zoom. I ask you questions (we initially agree on the list), and we discuss :). You can prepare slides if you want to (not a must, nobody did so far :D). I’ll do the spotlight sessions monthly after the Challenge finishes.

• To give you and your Substack more exposure, I will share the spotlight session:

  • all subscribers

  • my YouTube channel

  • my BiTES atomic newsletter

  • my other social media accounts

The Challenge includes (download links at the end of this post):

• Link to the Accountability Tracker. If you haven’t already, add yourself now!

• ALL-NEW Data-Driven, NLP-infused, Online Writing Course and the Data-Driven Copywriting Course to make your writing contagious, AND make sure it sells for you (without selling)

• Training courses from the Substack Quest: everything you need to nail positioning, product, growth, and sales.

• A mini workshop on how to Generate Stunning Midjourney Images without Prompting (link below)

• My custom personalized GPT CREATIVETECH Writer PRO trained on my viral stories to write high-quality long-form articles. Just updated with new training data. (link below)

• My custom GPT TITLE Generator 2.0 trained on 1000+ viral titles on Medium to generate titles that drive clicks. Just updated with new training data. (link below)

• My custom GPT High Converting CTAs Writer trained to turn your product descriptions into non-salesy CTAs you can use in your posts. Just updated with new training data. (link below)

• Dedicated Weekly Writing Challenge Sharing Post. I’ll ask you to share links to your posts, so that it can get even more traction. Comes every Sunday, you can share through the entire week. Make sure you also check other’s posts - that’s how we grow together!

Find the links below. Use this knowledge. Adapt the templates and guidelines to your niche and style.

Ready?

Let’s do this!

Here’s your Challenge pack of resources:

You’ll never get a price increase in the future! You can unsubscribe at any time.

Link to Challenge Resources

Read more

And I can’t wait to announce the WINNERS from the previous month 🤩

WINNERS AWARDS

Before I announce the winners, I want to personally congratulate who got multiple viral Notes in the Unplugged Hall of Fame, which also got her a bunch of sales of her newly published book!

And of the members who took their growth seriously last month and were active:

, , , , , , , , , , , , , ,

Congrats to ALL of you! You ARE ALL AMAZING!

Now, to select the winners, I also have to see you in the Accountability tracker, and since not all of you added yourselves, I’m gonna honor that and select ONLY among the ones who did.

As a reminder, I select the winners based on the Accountability tracker AND activity on the weekly sharing posts. Thanks to and his StackContacts I can now very easily extract the data and see who was the most active in my comment section.

Ok, so the winners are….

….drumrolls please.…

Winners from last month’s Notes Challenge:

This month’s awards are brought to us from who is so kind to grant 10x14 Days free of the Enterprise edition of his amazing Notes scheduling & analysis tool WriteStack. And now, since Substack enabled native scheduling, you don’t need to keep your PC open anymore!

So the winners are:

1. SPOTLIGHT SESSION + 14 DAYS FREE WriteStack Enterprise

   → ←

2. 14 DAYS FREE WriteStack Enterprise:

BIG Congrats to all the winners!!! I can’t wait to jump into the session with Vinayak, to talk about all things Substack! Looking forward to it!

The WriteStack Enterprise Award

Look for a DM from me about how you get the 14 days free.

The Spotlight Session Award

→ #1 Award is a Spotlight Session to talk about your Substack and more. To give you and your Substack more exposure, I will share this session:

• all subscribers

• my YouTube channel

• my BiTES atomic newsletter

• my other social media accounts

→ Watch all previous spotlight sessions here.

Time to kick off the new Challenge!

Challenge PARTICIPANTS:

This month for the last time: again, I’m gonna run the weekly sharing boost posts for ALL UNPLUGGED MEMBERS - you can all add yourself to the accountability tracker and participate in the sharing posts, but all training materials and AWARDS are reserved for PAID MEMBERS ONLY.

As usual, Paid and V.I.P. members also have their private access to the GPT, and the Viral Notes Writer Course with EVERYTHING below.

So this month, you have a fully automated workflow for Notes (paid members only):

1. Write with my custom GPT using the Viral Notes Writer System

2. Schedule using Orel’s Write Stack or Finn’s Studio Pro - now you don’t have to keep your PC active

3. Automatically re-post to social media using my automation app so you can grow even beyond Substack

What you need to do (short version):

• Join the challenge by adding yourself to the Accountability tracker

• Use my custom GPT to write and publish at least 3 Notes per day.

• Share your Notes in the weekly thread posts and make them your daily engagement routine - interact with others (you can do that every day until the next post comes on Saturday). The more activity, the greater the chances to win.

WINNERS AWARDS:

I’m gonna select 1 from the most active people who will win a Spotlight with me.

Rules for the winners selection:

• I’ll select the most active participants in the Challenge based on the Accountability Tracker and the activity on the sharing posts. Rules:

  • 1. must be in the Accountability tracker AND be active in the sharing posts (the more you share AND interact with others, the higher chances you have). I now extract data automatically (thanks to ), so there’s zero chance for error.

  • 2. must have completed the challenge (at least three Notes every day)

  • 3. you can win the same challenge more than once but in different months

  • 4. you can’t win both Writing and Notes challenges in the same month. If you do, I’ll invite the next most active person for a session

• Priority of selecting winners:

  • 1. most active among the VIP members

  • 2. most active among the annual paid members

  • 3. most active among the monthly paid members

• Announcement of the winners: start of next Challenge - 1st day of next month

• When do we do the spotlight: during next month upon your availability. We’ll do the session only if you’re willing to. If not, I’ll invite the next most active member until I get a “yes”.

• How do we do the spotlight: over Zoom or Substack Live — whichever you prefer. I ask you questions (we initially agree on the list), and we discuss :). You can prepare slides if you want to (not a must, nobody did so far :D). I’ll do the spotlight sessions monthly after the Challenge finishes.

• To give you and your Substack more exposure, I will share the spotlight session:

  • all subscribers

  • my YouTube channel

  • my BiTES atomic newsletter

  • my other social media accounts

The Substack Notes30 Monthly Challenge - Full Description

Your fully automated Notes Growth Engine step by step:

• Add yourself to the Accountability tracker.

• Post at least THREE Notes every day. One is not enough, especially if you’re new to the platform. If you have a few thousand subscribers, you can do one/day - you’ll still grow, but you’ll grow much FASTER if you post more. The effect compounds. As you saw in my examples from above, I get just a few subscribers from each Note => MORE Notes = MORE Subscribers!

• Take the Viral Notes Writer course. It’s beginner-friendly and it’s only 3 hours of bite-sized easy to digest lessons.

• Take the SUBSTACK QUEST Growth strategies - because it all works together as one engine.

• Use my custom Viral Notes Writer GPT the way I described in this video (the link to the GPT is below the video). It will turn your idea into 5 viral-ready Notes, you only need to edit and publish. Takes less than 15 minutes/day. Brings you subscribers (as many of you reported). Check out the latest update here.

• Use Write Stack to schedule and Substack Pro Studio GPT Bundle to analyze, optimize and schedule your Notes. Posting in the right times is crucial.

• Engage daily with at least 5 to 10 Substack members. Apply everything described in this video from the course, and this video from the QUEST.

• Share your Notes in the weekly Notes boost post: I will post one each Saturday, you’ll get it in your inbox. The next one comes next Saturday (post on the most recent one till then). I also share it in the chat. And remember to read, like, comment and restack some of the other Notes you like. Make this challenge your daily engagement routine - it helps YOU and other members grow faster.

• Use this automation to repost them to social media, so that you grow even more from external sources (as recommended by Substack).

• And if you have a Note with 100+ likes, DM me with a link, and I’ll add you to the Unplugged Hall of Fame.

If you follow all of the above, I’m confident you’ll pump your subscriber growth and you’ll see the effect immediately. People who do already report significant progress.

It’s time to make the most out of your paid subscription and get a proper return on your investment! Join that challenge!

The goal?

To gain subscribers who are engaged with your writing and who can (and will) be converted to paid subscribers later.

How?

Follow my system from this short but powerful course: The Viral Notes Writer System. I created it for you. It’s how I get to that high conversion rate.

The Challenge includes (links at the end of this post):

We’ll simplify everything with the course, now you have only 3 things:

• Link to the Accountability Tracker. Add yourself now!

• PAID MEMBERS ONLY: The Unplugged Hall of Fame (link at the end of the post) - I’ve set a place to display all Notes from the Unplugged paid member community that received 100+ likes. If you have a Note with 100+ likes, DM me with a link, and I’ll add you.

• PAID MEMBERS ONLY: Link to the The Viral Notes Writer System course - it’s only 3 hours, and it has EVERYTHING you need to implement my system. In it you’ll find:

  • My exact system I used to triple my subscribers growth in a month (takes just 15 minutes per day to write the Notes).

  • How to use my custom GPT to adapt it to your niche and audience (+ prompts)

  • How to use my custom GPT to grow outside of Substack (+ prompts)

  • As well as:

    • My custom GPT Notes Writer trained to write Substack Notes that go viral. I just upgraded its training using tons of data to sharpen it even more.

    • The right way to use the GPT Notes Writer in order to turn likes into subscribers (like me, Jeff and Daniel). Three SIMPLE steps to achieve it (you do the first two only once).

    • ChatGPT Prompting Strategy to help you write more relatable Notes based on data collected for your audience with the standard ChatGPT 4o model.

    • My Content Strategy: what type of Notes get the most traction - I incorporated this in the custom GPT.

    • My Engagement Strategy to attract new subscribers that are convertible to paid. You’ll have three modes:

      • EASY: engage with at least 5 new accounts per day

      • HARD: engage with at least 10 new accounts per day

      • TURBO: engage with at least 15 new accounts per day

    • A set of 11 Notes Templates (including the one that got me 10 200 likes and 167 subscribers) I’m using with a short guide on how to write them and an example from my Notes:

      • Image [with Canva template]

      • Opinion

      • Mini story

      • Mini listicle

      • Mini how-to

      • Mini analysis

      • Success story

      • Personal update

      • Personal Story (based on my first viral Note with 10k+ likes)

      • Journey (based on my second viral Note with 2k+ likes)

      • Comparison

      Image with simple text are performing well. They are highly re-stackable. I’ve prepared a Canva template you can easily edit (see resources below).

    • My Notes Guiding Principles on how to use Notes to gain convertible subscribers. A set of short rules about:

      • How to write powerful hooks

      • What types of Notes to write currently

      • How to engage with others on the platform

    • List of 17 types of Notes Ideas you can easily craft. If you don’t want to stick to my templates, you can use these as references in case you get stuck.

    • My list of 17 Rules of Short Form Writing I’ve proven to be working on Substack. I used them to train the GPT. The majority of these rules also work on Medium, X, LinkedIn, Quora. You can use them anywhere.

    • And how to use the Custom GPT for X, Bluesky and LinkedIn

• Link to the automation template that helps you automatically repost Notes to social media.

You have all this packed in The Viral Notes Writer System course (value $197).

Here’s your Challenge pack of resources:

Links to Resources for Paid Members:

Read more

This course is reserved for Unplugged VIP Members

If you’re a standard paid member or a free subscriber, you can still get access to this piece of gold at a very special launch price of just $47, valid till Easter’26

Make Your Offers Sell Themselves

This thought kept me awake at night for years.

To my employer, I was a liability. The goal was to maximize their returns and minimize mine. To my business I’m my biggest asset.

The ONLY skill that will set your business to success is selling.

When I sent my first sales email, I was terrified. Literally shaking. I hit send, watched 10 people unsubscribe immediately, and I wanted to crawl under my desk.

The next day, I got a bunch of sales.

That changed everything for me.

The problem isn’t that you can’t sell. It’s that you’ve been taught to sell in a way that doesn’t work anymore.

Classic copywriting tells you to stack features and benefits. To create desire. To push urgency. To position yourself as the expert who has all the answers.

But here’s what the data actually shows: people resist all of that. They’ve been burned too many times. They’ve bought courses that didn’t deliver. They’ve clicked on fake countdown timers that reset the next day. They’ve read sales pages that felt like someone was trying to reach into their wallet.

So they shut down. They don’t trust experts. They don’t trust hype. They don’t trust “buy now before it’s too late.”

And they shouldn’t.

What actually makes people buy (from my data, not theory)

I didn’t figure this out from a book. I figured it out by applying everything I learned in my 9-5 and by testing and tracking the numbers obsessively.

Here’s where I am right now:

10% conversion rate on native Substack subscribers — people who discover me on the platform and become paid members.

10% conversion rate on my automated webinar — a single recorded presentation, following the exact framework inside this course. It’s generated over $10,000 and converts strangers who’ve never heard of me before.

11.3% conversion rate on my Gumroad store — across 2,000+ sales. For context, industry average for online sales is about 3%. I’ve run paid ads and organic traffic for digital agencies for years. I have never seen conversion rates like this.

I now have more than 600+ buyers in my audience. Only 2 refund requests and that’s not a typo.

I run this as a side business next to my nine-to-five. It brings in $5,000 to $10,000 per month.

And I’ve packed everything in this course.

And for the first time I share my piece of GOLD - the exact slides of my high-converting Masterclass for you to plug into AI, reverse-engineer and apply to your offers.

Why most creators fail at selling (it’s not what you think)

It’s not a skills problem. It’s a confidence problem.

When you’re not confident about your offer, you try to convince people with features, benefits, and outcomes. You talk to the rational part of the brain. You stack proof and credentials and hope that’s enough.

But buying decisions are emotional. Every single one. The rational part of the brain just kicks in after to justify the decision that was already made.

So the real question isn’t “how do I convince people to buy?”

It’s: “How do I present my offer so well that I’d want to buy it myself?”

That’s the shift. And that’s what this course gives you.

What’s Inside:

In the Notion Doc:

• INTRO - The mindset shift most writers miss

• THE FRAMEWORK

• THE FORMULA & THE CONVERSION FORMULA TEMPLATE

• ADDRESSING OBJECTIONS BEFORE THEY EMERGE

• The HIGH CONVERTING OFFER CREATION TEMPLATE

• VALUE-FIRST SALES TEMPLATES [EMAIL & POST]

• EMAIL SEQUENCE ARCHITECTURE

• TOP 5 CLASSIC COPYWRITING MODELS

• SUMMARY

In the Unplugged Toolbox (also linked in the Notion Doc):

• 20+ PROVEN TITLE FORMULAS SWIPE FILE

• 5 HIGH CONVERTING SEQUENCE TEMPLATES

• THE 10 MOST COMMON CLASSIC COPYWRITING FORMULAS CHEAT SHEET

• The HIGH CONVERTING SALES PAGE CHECKLIST

• THE HIGH CONVERTING OFFER CREATION TEMPLATE

• CTA LIBRARY - 30 Calls-to-Action That Convert

• My HIGH CONVERTING MASTERCLASS PRESENTATION (I reveal this for the first time)

VIP Only: Here are the Links to the Notion Doc & The Unplugged Toolbox:

Read more

This post stays active for one week, so make it your daily engagement routine. Share your posts, but also read and join the conversation in the comments of the other members’ posts. It will help you grow, it will help them grow.

If you’re not yet in the Writing Challenge, NOW IS the best time to join.

VIPs: YOU HAVE A GIFT👇

Do you use my custom GPT that generates viral headlines? I just updated its data training, PLUS - it now gives you subtitles as well!

Have you tried the High Converting CTAs custom GPT? It will help you sell more with your posts. It also got a fresh, new data-driven training update optimized for conversions.

If not, NOW is the time to start!

Here’s what you need to do now:

1. Add yourself to the Accountability tracker, so that you have a chance to win the award

2. Share a link to your posts in the comments below so that we can find it, read, comment, like, and share it!

3. Make this challenge for your daily engagement workflow - Check other people’s posts in the comments of this post. Find something you like to read more about and give it a like, comment and share - that’s how you grow faster (and you help others grow too).

Anyone from the Unplugged community can participate.

Let’s do this!!

Subscribe now

Share your link now 👇

P.S. If it doesn’t challenge you, it won’t change you. If you haven’t already, Join the Writing Challenge if you’re serious about growing on Substack.

P.S.S. If you’re not taking the Challenges, you can opt-out from receiving these weekly posts without unsubscribing for the rest of the content - do this from your settings here:

This post stays active for one week, so make it your daily engagement routine. Share your Notes, but also read and join the conversation in the comments of the other members’ Notes. It will help you grow, it will help them grow.

So grab your Viral Notes Writer GPT & post some highly engaging Notes.

If you’re not yet in the Notes Challenge, NOW IS the best time to join, because THIS MONTH YOU WIN:

🎁 This month: Win FREE WriteStack Enterprise 🎁

This month I’m selecting 10 winners!

1. TOP 1 most active: Spotlight with me + 14 Days of WriteStack Enterprise 🎁

2. Next 9 people: 14 Days of WriteStack Enterprise 🎁

Rules available here.

Here’s what you need to do now:

1. Add yourself to the Accountability tracker so that I consider you for the prizes.

2. Share a link to your Notes in the comments below so that we can find it, read, comment, like, and restock it!

3. Check other people’s Notes in the comments. Find something you like to read more about and give it a like, comment, and share. Make this challenge your daily engagement routine - it helps you, as well as the other members in the community.

PLUS: if anyone has a Note with 100+ likes, DM me with a link, so that I can add it in the Unplugged Hall of Fame :)

You can share your Notes here throughout the whole week, until the next sharing post on Saturday.

Anyone from the Unplugged community can participate.

Subscribe now

Let’s do this!!

Share your link now 👇

P.S. If you haven’t already, Join the Notes30 Challenge if you’re serious about growing on Substack.

P.S.S. If you’re not taking the Notes Challenge, you can opt-out from receiving these weekly posts without unsubscribing for the rest of the content - do this from your settings here: