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A
So I think like, my biggest advice is to send multiple emails. If you send just like one lunch email and oh, here's my paid plan. Some people will read it, some people will not read it, but most of the people will read it and then forget about it.
B
A mix of those and some other growth tactics. I'm sure I've gotten you to your 44,000 subscribers at this point. You've recently launched this paid side of things. I'm curious when you decided, like, okay, it's time to flip the switch. I'm ready. The time is now. How are you thinking about that?
A
Sure. So I had two, two things in my mind. First is to have a big enough mass of subscribers before I flip to switch. Flip to paid. I don't know why, I just felt like I wanted to make it first. Like to see if I can actually make a big enough newsletter. Even, like, only if I prove to myself that I can collect so many subscribers, then it will be like, I will be worthy enough to start a paid newsletter. And the second thing is that I wanted to wait until I have a really good plan for launching the paid newsletter. Like, I didn't want to do it. Like, oh, okay, by the way, new, new, new tier. You can join the paid like plans if you want. If you don't want, that's fine. I didn't want to do it. Like, by the way, as I said before, you must be mindful about what you do. You must really care. So building up this plan took a long time. And only when I felt confident enough that it's good, then I flip this. The switch to paid.
B
I love that. And just from seeing it and like hearing you talk about it, like behind the scenes, like it is a serious plan. Like, you were not joking around with this. Like, you had this full email sequence built out. You created a whole book around like the same time the launch.
A
Oh, nice. You have the book.
B
Just insane.
A
Yes, I have the book. You have the book?
B
Yes.
A
Yeah, it was. I saw other newsletter authors and how they launched their paid plans and it really seemed like a missed opportunity because it didn't really, like they didn't remind people enough about it and they didn't like have a sequence that makes people think like, it's like, you know, gradual learning about what's in the offer. So yeah, I built this plan and with the book, with everything I do, I tried to like every offer that I provide, the offer must be tangible and non calculatable. So tangible makes sense. But non calculatable meaning let's think about another newsletter that sends four emails per month and it costs $20. So in people's brains everyone is thinking, okay, so $20, four emails per month. It means I'm paying $5 per email, which is like a cup of coffee. And I don't want people to make those comparisons. So I thought about what tangible offers I could provide that will make the newsletter a bit more non calculatable. So, so the book is one of them and the community that I'm starting in the newsletter for like the marketing leaders that are paying is also part of it. So it's like making the offer much more holistic and again not non calculated.
C
Right. So like offering things that they can't actually say, well this is worth X amount per issue. You've like added so much value there that you can't just break it down like five bucks per issue. That's, that's really smart.
A
Exactly. I do it with everything by the way. Like for example, I give workshops and trainings for companies which is like a 90 minute Zoom call with their team. So like I don't want them to divide the amount of minutes by the cost. So I give other things like a 30 minute one on one with the leader and also follow up AMAs with the entire team via email and like to make the offer much more like holistic and less, less calculated.
B
Yeah, I love that. Okay, can we talk about exactly what you are including in the, the paid subscription offering just to start and then we can kind of dig into the launch and like how it's gone and that kind of thing.
C
Sure.
A
So as I said, I send one marketing idea every Friday and I actually kept my best marketing ideas until I could get the content because I know, but it's not really for monetization reasons because some of these ideas that I send every Friday now are like if everyone started using them, they will lose their power. Like it's like the law of declining growth channels. So I wanted to keep those specific marketing ideas to a smaller audience base. So I like, I wrote a lot of articles during those two years and just waited before publishing them because I didn't want to send those for everyone. So that's what I offer. And I also give archive access so you can read all of the past marketing ideas, which is something that I know people really love and they want to have like this library of marketing ideas. And it's, this is what's going on right now in marketingaries.com I also give the book a free PDF copy of the book that Chanel has a physical version of. And starting September, there will also be a community. So basically it's like a group chat with me and others and I plan to do it really well. So I plan to really have a schedule and like you will know in advance what are we going to discuss in the community every single day. And people will share ideas and I will post interviews and AMAs with my friends that will be there too. So it's going to be like a whole thing. And that's the offering of the paid tiers of marketingedits.com that's awesome.
B
I love it.
C
I have one question before you decide to go paid, just for some context, were you monetizing the newsletter in any other way prior?
A
No. I don't know why, but it felt wrong to monetize with ads or stuff like that. But it's just a hunch because I wanted to build trust with my audience so I wanted them to really like, really enjoy free. And it worked. When I flipped the switch, the two paid people really loved it.
C
Yeah, you did the ultimate like give, give, give, give, give, give, give, give and then ask basically. Right. Like two years basically of, of providing really high quality, engaging free content. And then when it was time to flip the switch, which obviously you put lots of strategy and thought behind, it was an easy and a much easier ask for people, which is why it was so successful. I know you don't want to share exact numbers, but we can safely say that you have over 500 paid subscribers to the newsletter now.
A
And all of those 500 joined in the first few days after launching the paid newsletter. Which is amazing because it means that like 500 people joined the premium plan before I even sent a single paid world article. So it's great and people trust me and it shows because 500 people pay for a product that they have not experienced yet. So it's great.
C
Yeah, yeah, I'm included in that. I definitely joined especially. Especially what, Tom? Honestly, one of the tactics that worked on me was like, hey, I'm offering this entry level price and it's going to go, it's going to basically double at a certain period. And so I was like, yeah, I want to get in on the, the entry level price. So I mean, I don't know how much thought went even into that. But that, that was, that was something that worked on me.
A
That was actually Chanel's idea. I actually went with Chanel before flipping the switch and that's what she owe.
C
Chanel a hundred bucks actually, actually said.
A
Like, I actually like told Chanel, okay, I'm going to charge 100 bucks. And she said, no, it's too cheap. You should increase the prices and only have the $100 for the first day or two. So that, that's what, that's what happened. Yeah.
C
Amazing. That's, that's very amusing how that went.
B
That's why I made sure to end.
C
This conversation right now. My God.
B
That's why I made sure to buy when it was a hundred bucks. Because I was like, I know this is coming. I love it.
A
Thank you.
B
That's great. Okay, so this launch, just seeing it, like we had talked and you had mentioned a couple of other things and so I'm just curious, like, can we talk through, like your strategy for launching, like all of the pieces of the puzzle? Like, there's so much going on in this. I think a lot of people see, you know, Eleni Richeski or someone who has a paid newsletter and they get so overwhelmed of like, how do I even begin? Like, where do you start going from a free newsletter to a paid newsletter? Like, how did you think through the process? Like, what was involved in the launch? I'm just curious of like, how you've been started with that.
C
Well, I'll also add just one more follow up question to that. Is you mentioned sequences and with Substack you can't really quite do that. So I'm curious if you had any other software that you're using as well.
A
Yeah, it's not really a real sequence. It's like a manual sequence that is planned out in an Excel sheet beforehand. And like, and then every single day or a few hours I go ahead and send the image. So I think like my biggest advice is to send multiple emails. You know what I mean? Like, if you send just like one lunch email and oh, here's my paid plan, like, some people will read it, some people will not read it, but most of the people will read it and then forget about it. So you need to send a lot of emails, like, my plan real quick.
B
Before you keep going. When did you start sending emails? Like, hinting at this? Like, was it early on? Was it just a couple days before hinting?
A
Never, like, it was a surprise, I think.
C
Sorry.
B
No, but you never, like, before you.
C
Actually open the doors, like, open the cart, if you will.
A
Yeah, never. Like, no one knew, like, except for 10 friends like Chanel who helped me with the advice. No one knew before, I think so.
B
Interesting because you always hear marketing people say, like, tease it beforehand.
A
Let people know why like if I tease them and they cannot pay, how will it help me? I'm wondering, like. Interesting.
C
Yeah, that's the whole Jeff Walker's like product launch formula I or something along those lines. I can't remember the exact name of the, of the book but he's always like you got to seed your list or seed the, you know, pre sell the, the thing that you're going to be launching with people basically at the most being able to sign up for like on a wait list or maybe add their names to like a pre launch sort of list and then they're kind of primed once you actually like open the doors. So you didn't do anything along those lines?
A
Yeah, that's smart. What I, what you said I didn't do it. But it's a smart, it's a smart idea. I think people should do it. But I think it's a mess. Like especially in substack when there is no automations, it's a mess to keep a separate list of waitlists. But it's smart like conceptually I like it, it should work. Well what you just said anyway. No, I didn't tease anything. I just dropped the bomb one morning, it was a Wednesday morning and I said, here is everything that I offer. It was a very long email with a lot of social proof and tangible things and if you join in the next 24 hours you will get a very discounted price. So that was the first email. And again of course after 12 hours in the evening of that same day I sent a reminder. And each reminder is not like, you know, a chatgpt generated email like oh, reminding you about things. It's usually with added value like my feelings, my experience or like hinting at another thing that is coming and et cetera. The day after there was unfortunately I had to extend the sale. I had an issue with the stripe again. First time charging anything online. So sale extension for another 24 hours and then that evening another reminder that the sale is going to end soon. So that's the first 48 hours. Friday morning Bookland. I initially wanted to launch the book with everything else but Chanel smartly told me not to do it. Like to wait with the book for Friday. So that's great. So I launched the book and I said that each paid subscriber gets the book for free, like a PDF copy. So that's Friday and then Saturday, like an FAQ about the book, Sunday, the first chapter of the book for free. And then if you want more, click here to subscribe and read the rest. Monday, social proof that I generated within the last five days, like social proof of the paid subscribers and the things that they've been saying in the last four days. So that's like a lot of testimonials and quotes. Tuesday is another, like, sale that's going on, like a smaller sale than before and only until Friday. Wednesday, another reminder. Reminder. So as you can see, it's a lot of emails and like the entire lunch week or campaign ended the Friday after. So it's like nine days where each day was about one or two emails. Now, not all of the emails were sent to everyone. Some of the emails, I only sent them to the most engaged subscribers because I didn't want to like people to unsubscribe. So some of the reminders were only sent to the top 2000 most engaged readers. So that was part of the strategy. And yeah, that's how the launch plan looked like.
B
So what? Because substack shows you which emails drove the most paid subscribers. Can you see, like, was it the beginning of the launch, the end, the middle? Like, which emails had the biggest impact?
A
The. The. The one email that had the biggest impact is the reminder email of the first day. Why? Because it had the most urgency. I think it was like 10, 10 hours left for the one time or like one time sale. Also, the book launch was big. People really want the book. The COVID looks good and it's a PDF copy. It's like 400 pages. You get to keep it forever. Like, why not? And I anticipated that a lot of people will just do one month and then cancel just to get a book, which is fine, like if it's their choice. But today, exactly 30 days after that launch, I see that all of like most of the subscribers are still subscribed, like the paid one. So almost no one unsubscribed, which is great.
B
Sam.
Podcast: Newsletter & Email Growth: Growth In Reverse
Hosts: Chenell Basilio and Dylan Redekop
Date: January 29, 2026
In this candid, strategy-packed episode, Chenell Basilio and Dylan Redekop interview “A” (the creator behind a fast-growing marketing newsletter) about how he launched a paid version of his previously free Substack—and earned over $50,000 with 500+ subscribers in the first few days. The conversation digs into the full playbook: when and how to flip the paid switch, crafting an irresistible value proposition, launch tactics, and the importance of not making your offer “calculatable.” Anyone growing or monetizing a newsletter will walk away with concrete, actionable ideas.
Subscriber Milestone Before Monetization
“First is to have a big enough mass of subscribers before I flip to switch. Flip to paid. ...Only if I prove to myself that I can collect so many subscribers, then it will be like, I will be worthy enough to start a paid newsletter.” (00:32–01:03)
Need for an Intentional Plan
“I wanted to wait until I have a really good plan for launching the paid newsletter. ...You must be mindful about what you do. You must really care. So building up this plan took a long time. And only when I felt confident enough that it’s good, then I flip this. The switch to paid.” (01:03–01:32)
Avoiding Simple Value Calculations
The goal: make benefits so comprehensive, no one simply divides price by number of emails.
“With everything I do, I try to... the offer must be tangible and non-calculatable....I don’t want people to make those comparisons.” (01:55–03:07)
Strategies included:
Value Stack Example
“So I give other things like a 30 minute one on one with the leader and also follow up AMAs with the entire team via email and like to make the offer much more like holistic and less, less calculated.” (03:18–03:44)
Premium Content Reserved
“Some of these ideas...if everyone started using them, they will lose their power. ...So I wrote a lot of articles during those two years and just waited before publishing them because I didn’t want to send those for everyone.” (03:56–04:20)
Archive, Book, and Community Access
“A free PDF copy of the book that Chanel has a physical version of. ...Starting September, there will also be a community...a group chat with me and others. ...You will know in advance what are we going to discuss in the community every single day.” (04:45–05:25)
Entry-Level “Founders” Price
“One of the tactics that worked on me was like, hey, I’m offering this entry level price and it’s going to go, it’s going to basically double at a certain period.” (06:50–07:13)
No Pre-Announcement/Teasing
“Never. Like, no one knew, like, except for 10 friends like Chanel who helped me with the advice. No one knew before... I just dropped the bomb one morning, it was a Wednesday morning.” (09:08–10:07)
The Manual Launch Email Sequence
Flooding the Inbox (Intelligently)
“My biggest advice is to send multiple emails. ...Most of the people will read it and then forget about it. So you need to send a lot of emails.” (08:29–09:00)
| Day | Action / Email | |-------|----------------------------------------------------------------------------| | Day 1 | Big surprise email with all details, social proof, tangible bonuses | | Day 1 | Reminder email with added urgency/value | | Day 2 | Extended sale period due to Stripe issues; another reminder | | Day 3 | Book launch email: PDF free for paid subscribers | | Day 4 | Book FAQ email | | Day 5 | First free chapter as teaser/conversion driver | | Day 6 | Social proof (testimonials from new paid subs) | | Day 7 | Small “last call” sale/discount | | Day 8 | Final reminders | | - | Note: Some emails only sent to highly engaged segment (top 2,000 subscribers) |
“The one email that had the biggest impact is the reminder email of the first day. Why? Because it had the most urgency.” (12:59–13:14)
On “Non-Calculatable” Offers:
“Tangible makes sense. But non calculatable meaning...I don’t want people to make those comparisons.” (A, 01:55–03:07)
On Trust Before Monetization:
“I wanted to build trust with my audience so I wanted them to really like, really enjoy free. And it worked. When I flipped the switch, the paid people really loved it.” (A, 05:37–05:57)
On the Power of Multiple Launch Emails:
“My biggest advice is to send multiple emails. ...Most of the people will read it and then forget about it.” (A, 08:29–09:00)
On Launch Surprises Versus Teasing:
"If I tease them and they cannot pay, how will it help me?" (A, 09:30–09:37)
On Social Proof and Stickiness:
"...Today, exactly 30 days after that launch, I see that all of like most of the subscribers are still subscribed, like the paid one. So almost no one unsubscribed, which is great." (A, 13:25–13:46)
This episode lifted the curtain on a high-trust, high-urgency paid newsletter launch. The strategies discussed are a must-listen (and must-implement) for list-builders ready to monetize—and for anyone seeking to add value that subscribers can’t put in a spreadsheet.