What it really means to get that pretty orange checkmark

This article is about my journey to 101 paid members, the strategies I took, whether it was worth it, and what it means to get an orange checkmark. 

If you are a paid member, I recommend reading How to create a world-class Substack publication, How to get noticed on Substack, and How to get 5,000-20,000 new readers for your Substack publication every month to add context to this article.

If you are not a paid member, you can read everything with a 7-day free trial, or give us a one-time tip.

On Friday, August 25 at 9:12 AM, I got the email most of us have been striving for and became a Substack bestseller.

What does that really mean though?

Well, first off, I had actually become a Substack bestseller the day before, and as far as I can tell, you don’t actually need 101 paying members to receive bestseller status. All you need are 101 people who have agreed to either a trial membership, to start paying once their upgrade period is over, or to generate at least $1 in revenue from somebody without them canceling their membership.

At the time I received my orange checkmark, I had no less than 20 subscribers who hadn’t paid me even $1. How is that possible?

Eight of them were still in their initial “trial membership” of either 7 or 30 days, and another 12 had been comped a membership and agreed to upgrade once their comp ended.

That means, at the time of my “bestseller” status, I only had about 80 people who had given me any money at all.

Of those, another 17 people were on “hardship scholarships” where they pay as little as $1/year for their membership.

The day I got the email of my bestseller status, my gross annualized revenue was $4,211. That’s 83% of the expected $5,050 that a $50/yr membership should generate over the course of a year for 101 members.

***This is a long post that will be truncated in emails. I highly recommend you go to this page to read the whole 5,500-word post without interruption.***

Of course, the calculation of your gross annualized revenue is completely bonkers as a metric in the first place.

How much money have I actually made to date, though? Substack doesn’t tell me. Even though there are a bajillion metrics in my dashboard, I have to go into Stripe to find how much I’ve actually been paid by Substack.

Since I have a half dozen different websites hooked up to Stripe, this means I have to spend a bunch of unnecessary time trying to pin down how much Substack has actually paid me.

In order to find this information, I had to go to STRIP>PAYMENTS>EXPORT and export all my payments.

Then, I had to sort to find the ones that looked right. It seems like when Substack creates a payment, the description is Subscription Creation and when they invoice in future months the description is Invoice XXXXXXXX-XXXX.

Why is this so hard? I don’t know, but when I deleted and sorted “properly” it looks like my payments added up to $2514.30. Perhaps they don’t want you to be able to easily find out how little you’ve actually made for months of work, but I’ve never had a payment partner be this opaque with their numbers.

I should have easy access to this number right on the dashboard without having to search and guess. The nice thing about subscriptions is that they build over time. So, assuming I don’t royally muck it up, I should be able to maintain and build on this number in 2024.

Still, for some context, I’ve run three of my own Kickstarters and been involved in three others. The ones I personally ran raised $24,541. The ones others ran with/for me raised $34,591. Together, they raised $60,132.

Revenue is deceptive, so here is the profit I made from each campaign after production, printing, and shipping.

• The Obsidian Spindle Saga (Books 1-8) - $3233.54

• This is NOT a Book -  $3,271.30

• The Wicked Witch Academy duology - $2,800.39

• Cthulhu is Hard to Spell paperback campaign (Books 1-3) - $2,379.40

• Ichabod Jones: Monster Hunter card game - $680.74

That’s a total profit of $12,365.97 across these five campaigns. Whether you take the total revenue of just my campaigns (10%) total campaign revenue (4%) or profit across those five campaigns (20%), getting a Substack bestseller tag is a fractional share (4%-20%) of what I earn on Kickstarter alone.

This is not to knock Substack at all. Memberships are an entirely different business model, but it does show that bestseller status is a nice feather in your cap, and it’s great to strive for, but it doesn’t mean you’ll suddenly be making bank.

Additionally, this is only a comparison against one income source. I also co-own a conference and course business, consult with authors, and work with book marketing clients that have generated substantially more than what I showed above. I can’t share with you all my total revenue since Writer MBA does not have a full transparency policy, but this is how much revenue I have generated going back to 2016 that I can share.

Please note that this breakdown includes my mortgage and my salary, so this year is not quite as bad as it looks from the expenses. Total cash-on-hand and investments are up 13.06% from last year, and last year was a record year for us. So, we’re doing just fine at the moment.

From this, you can see how much revenue I generate every year compared to how much money it takes to become a Substack bestseller.

That said, I am only charging $5/mo or $50/yr. If I raised my price, then my revenue would likely increase.

Additionally, I have to state again in no uncertain terms that this is not a knock on Substack. Memberships tend to grow much slower than other areas of your business, and I’m happy that one is finally working for me after years of struggle. I only reveal all these numbers to show that a Substack bestseller doesn’t mean that much financially in and of itself.

It definitely means something, though. It means over 100 people have committed to going on a journey with you, and that’s amazing.

Now that I’ve beaten the financial dead horse, let’s talk strategy. I’ve been thinking a lot about how to break this down, and I think the only way it will make sense is chronologically.

The beginning

I started my Substack journey on August 12th, 2021 after a few of my comic book friends convinced me they were getting organic reach here and I decided to see for myself. I wasn’t in the headspace to create a full publication, but I got five subscribers that first day.

I then proceeded to do nothing with it until February 8th, 2023. In the intervening two years, I was able to accumulate 31 subscribers doing literally nothing.

On February 11th, and I decided to start sharing both of our Substacks with our audiences. Monica had already been putting effort into her Substack, The Author Analyst, for a while, but I wasn’t quite ready to dive into Substack with both feet. The day after we shared my publication, it leapt from 31 to 52 subscribers.

Then, I didn’t do very much until March 13th, when Facebook disappeared me. Here’s what I said about it then.

Between February 11th and March 13th, I had gone from 31 to 65 subscribers.

I nearly doubled my subscribers in the subsequent month, but it would be lying to say I was giving even minimal effort. That all changed when Facebook disappeared me. I had been working with Circle for a while, but it hadn’t been really going well. I decided that if I wanted to own the customer relationship, I needed a change, This is the moment when I decided to go all in on Substack.

Going paid

Backing up just a bit to that February 11th date, when Monica and I decided to start telling our audience about Substack, I also decided to “go paid”. I got my first paid subscriber on the first day.

By March 14th, I had four paid subscribers.

I consider this the nadir point when I started to focus on growth and designing a publication to attract new readers. Until now, most of the information I posted on Substack was reposted from Facebook.

has a lot of guidance on going paid. 

I didn’t listen to any of that. One day I just decided it was time to focus on Substack, and I turned on paid. I didn’t attract a lot of people at first, but enough that it showed there was a little bit of traction there.

I wrote an article about going paid. It’s all worth a read, but this is an exercise I think is hugely valuable and might help you.

The first design (and redesign)

Originally, I decided to call my publication The Author Ecosystem, based on a concept I had been working on for a couple of years at that point. Between March 15th and April 24th, I was building The Author Ecosystem.

During that same time, Monica and I were developing an archetype system, and it just happened to perfectly align with the Author Ecosystem brand. By that time I had 15 paid subscribers and 308 total subscribers.

This meant ceding The Author Ecosystem to our company, and completely changing the name of my publication. We had decided to do something pretty bonkers on the 28th, so I had to make some drastic changes pretty quickly.

I decided on The Author Stack (authorstack) because I assumed it would show up on a search for #authorstack pretty prominently. Additionally, I talk a lot about “the stack” and becoming a “full stack author”. So, I thought it would fit with the stuff I already talked about in my articles.

Comping 25,000 members

When that rebrand was done on April 27th, I had 378 subscribers and 15 paid subscribers.

Then, on the 28th, I started comping my main email list. We gave everyone on our Writer MBA email list a free three-month subscription. I also gave everyone on my 20,000-person writer email list a three-month comped subscription as well.

It took until May 12th to figure out the comps and get everyone situated, and by then I had 21 paid subscribers.

It should be noted that this strategy caused a big hit to my gross annualized revenue. As some of my paid members were on one or both of those lists, my income took a dip, on May 11th, my gross annualized revenue was $1,060.

At the lowest point of the dip, it went down to $740, even though I had more paying members than ever.

It rebounded after that, but oof. It was a big hit. So, why did I do it? I talked about that in my article about Substack sections, but here is the relevant part.

More than any of the reasons above, I love experimenting with weird things nobody else would try. I’m really into first-hand data and have said for years that I either want to be a horrible warning or a shining example and I don’t much care which one.

My bet was that if I could comp people for three months and let them see all the value, then they would want to stick around and pay for content. On top of all that, Substack claimed that 5-10% of your free subscribers will eventually become paying members, and the allure of 2,500 paid members was too much to pass up. 

[SPOILER ALERT: This might be true for people who find you through the internal Substack network, but I have certainly not found it true with imported subscribers, even if they have already bought something from you on another platform.]

One last thing I will note, if you are importing multiple different lists, then make sure there are no duplicates. I didn’t do my due diligence, so some people were comped up to 9 months when it was all said and done. Don’t be like me, be better than me.

The slow, steady climb

After doing those imports, I decided to spend the summer providing maximum value. My content schedule includes a serialized novel chapter that is released every Monday, an article or tutorial every Wednesday, and then a weekly digest every Saturday filled with links to other articles I loved during the week. Plus, members have access to a dozen novels and all three of my non-fiction books.

Between May 12th and July 18th, I grew from 21 to 45 paid members.

Between July 28th and August 12th, over 4,000 members would lose their comped status, so I decided to prepare for it by culling anyone who hadn’t opened even one email in the preceding three months. Here’s what I wrote about that first purge. 

Looking back, I probably should have waited to cull until after the next part of my strategy, but hindsight is 20/20. It was surely nice to see a 10% increase in my open rate after this purge with no discernable decrease in the number of opens.

Between July 28th and August 12th, 4,500 members lost their comp status, and my total paid subscribers only rose from 45 to 69. As members lost their comp status, some of them unsubscribed, and I purged still more until I stabilized my list on August 12th.

This is what I wrote about it at the time.

At the lowest point, my subscriber count dipped to 17,960.

However, I’m still getting roughly the same number of opens as I did before culling. It might be down a couple hundred opens for every article I post, but it’s within a standard margin of error of where it was with a 25,000+ person list.

One time offer

If you’re following along, then currently you will note that 69 paying members on even a 17,000 person list is nowhere near the 5-10% Substack talks about in their conversion percentage discussions.

I’m not surprised at the fact my number is currently under 1%. I expected with the introduction of Notes and more casual readers that the actual conversion percentage would be closer to 1%.

Additionally, I assumed that the highest conversion percentage would come from people who found my publication through the Substack network, as they were already “bought-in” to the subscription model. This has certainly been the case.

I had always converted roughly 1-2% of my audience into my Kickstarters, and that was what I expected here, too. I’m not surprised by the results, but I am a bit disappointed in them.

That said, I was still pretty close to the 101 paid subscribers that it took to get a checkmark next to your name.

I was only 31 away on August 12th. On August 13th, I sent out a winback offer.

I created a segment of subscribers who chose not to continue their subscription and sent them the following email.

There are a couple of things to note about this offer. The most important of which is that every word is true. Several people did email and tell me they couldn’t afford to pay full price.

The second thing is that this offer really did go away on August 31st. I strongly believe in the pay-what-you-can-afford model, especially for counties with pay disparity. If you email me at russell at wannabepress dot com I would be happy to discuss a hardship scholarship with you.

I never want money to get between somebody reading my work. That said, it’s not something that I advertise, and I do hope people use it responsibly. However, if they abuse the system that’s their karma. I don’t have time to worry about somebody scamming me out of $5.

I know I give way more than $50/yr in value. Any one of these posts could easily make you $500.

By the following week, I was up to 82 paid members.

On the 23rd, I was up to 86.

On the 24th, I sent a follow-up email telling everyone who didn’t choose to upgrade that they only had one week left. I ended that day with 103 paid members and 7 on the free trial.

Even though I only got the email on the 25th, I saw the badge come through at 10:30 AM or so during Substack Office hours. When I checked I had 93 Paid and 8 Free Trials, which is why I assume that free trials count toward the overall total.

For those of you saying “I didn’t know we can email people!” Yes, you can. All you have to do is go to DASHBOARD>SUBSCRIBERS and click on the box next to a certain subscriber’s name. It will come up with a box that says EMAIL.

You can also create filters, or check the box on the left of where it says Subscriber at the top to select everyone on that page. It should say something like 50 matching readers selected. Select all XXX.

If you’d like to email everyone in that segment, click the Select all XXX link and then email. I really dislike it when people fill my Substack inbox with special offers. I would much rather they just email me and keep my app filled with nothing but articles.

As far as I know, this bypasses the “disable email” option in the settings. So, if you email people through this method, it will get to people’s inboxes, even if they disabled emails. This is the one downside of using it, so use it sparingly.

One time offer, redux

Between October 24th and November 12th, 12110 members lost their comped status.

Therefore, since I had just a successful time of it the first time, I thought I would run the same one-time offer again. It should be noted that it was impossible to segment out the people who got the offer the first time, so I actually sent this offer to 16,300 people. Since there were 2.5x the amount of people losing their comped status the second time, I expected 2.5x more new members than last time.

The first time I ran this in August I received 70 new paid subscribers. This time, it was 130.

Based on the tracking I’ve been doing all year, I thought it was possible to hit 300 paid subs this year. I just passed that number after this second round of one-time pricing.

I’ve got a lot of other way to bring in revenue, so I don’t know how much you can use me as a model, but I’ve only seen a 1.5% conversion rate, which is again right around the 1-2% I would expect but far below the 5-10% Substack claims.

I’ve recently added another round of uploads to my Substack, and I have 400 people coming off their comps in January, so it’s possible I might run this one more time to try and hit 500 members, but I think this is probably the last time I’m running this playbook.

The only reason I ran it this time is because so many people on my old lists have supported me for years. It’s not something I want to offer people who are new to my ecosystem. It’s something I wanted to give as a gift to people who have been around for a long time.

This is where I stand right now on 12/2/23, with 310 paid subscribers paying an average of $28/yr.

Before this, on November 15th, I had 180 subscribers with a Gross annualized revenue of $7,271, for an average of $40/yr. As you can see, while I got more paid members, it came with a significant hit to my average subscriber revenue.

For me, it’s worth it to make that sacrifice to build a more robust membership base. As I mentioned, I have several other streams of revenue that fund my business. This subscriber revenue is something I plan to build slowly over time so that it can support me in the future. I hope that by the end of 2024, I can increase my membership to 1,000 active members with over a million page views a month.

That would necessitate roughly a 300% increase in both in the next year. Since I’m focusing mainly on those two metrics, focusing on my gross annualized revenue would work in direct conflict with that goal.

Comps (finally) ending

On April 28th, 2023, I comped 25,000 subscribers from my previous mailing list to The Author Stack. Because of some mistakes I made while uploading my list, some people received 9+ months of comped access, which finally ended on 1/26/24. This is what it looked like on that date.

On December 1st, there were 310 paid subscribers, and now there are 353. That’s not incredible by any stretch, and 39% of them came from the Substack network, but that’s still a significant amount of money. My publication is at $10,700 in gross annualized revenue, and if $6,000 of that is from my old comp list, and I get a chance to grow my relationship with them in a non-salesy way, it was probably worth it. Due mostly to running ads, I’ve been able to grow my publication by over 2,000 subscribers since December 1st as well, but that doesn’t help us get to 1,000 paid subscribers, so I’ll leave it there.

Anniversary pledge drive

After the comps ended and settled, I thought it would be a good time to host another pay-what-you-can-afford pledge drive. I started with 362 paid members, and decided to offer discounts from 0% ($50) to 80% ($10)

My gross annualized revenue was $10,831 before I did the pledge drive.

I ran it from February 1st, 2024 to February 19th 2024. When it was over I had 473 paid members, and $12,647 in gross annualized revenur.

This will be the last time I offer $10 or $15/yr. pricing and unsurprisingly those were the two most popular tiers. Interestingly, we were able to get as many new members at $10/$15 as we did when we offered $1/$5 tiers. We’ll offer this again in May with $20 being the lowest tier and I’m interested to see if we can maintain this level of enrollment.

The “correction”

According to this graph, the worst thing I can do is…post words, especially words from other people.

I thought we ended on a bonkers high when we finished our last pledge drive, but I’m surprised to see so many people fall off so quickly. We’ve lost hundreds in Gross Annualized Revenue (GAR) this week alone.

I thought when I started guest posts that it would be a boon to subscriber growth, but I haven’t seen that as such. I thought it would be great for retention. It honestly hasn’t been great for either.

I have seen people stop their payments more with guest articles than my own…

…but like, I want to do that stuff, and I want to center other people’s stories because that makes us better writers.

Often, people look at me like a business stooge, but I only know all the rules so I can break most of them. I know what I want out of my career and what I should expect from my career, so that I can chart a course that makes sense to me.

Also, a lot of people do like it. Over 10,000 people read just about any post from anyone on my publication, and it’s usually over 12,000 people at least.

For many publications, that is more reads than they get in a month, and it’s important for me to keep doing that work for the industry at large, and for those writers specifically.

I think it’s important to center other voices even if my subscribers don’t, and I think over time they will agree with me if they think about it. Are these people maybe unsubscribing to become a paid member at one of my contributor’s Substack? Well, I hope so.

I want to drive growth for them, even if it takes it away from me.

One of the hardest things to do in business is to force other people to take their medicine. Almost every business book I’ve ever read tells you to do the things your customers want, but I care mostly about what they need. 

I have no idea which one of these posts with sing with a reader, but I know one of them will if they stick with it. Knowing how to do marketing and sales helps me do that and craft a long-term narrative about how to build a thriving, sustainable business with people who stick with it, even though most people won’t.

Also, they can get what they want anywhere. They probably do, in fact, and it doesn’t work. They don’t know why it’s not working, but they know it doesn’t work.

That’s my job, as a writer, an editor, and a curator.

Why would somebody subscribed to my publication know what they need? They don’t even know how to surface their problem, let alone deal with it.

I know what they need because I’ve been through the shit of it and know all the pitfalls.

When you don’t give people what they want, they leave, and they do…a lot, for all sorts of reasons. When you placate them, they stay, docile and happy.

They also stay complacent, and I’m not about that life.

By all metrics, this is bad business. I know what people want. I could just give it to them. They would never leave. They would think they are happy…

…but they would be miserable. I don’t want you to be happy. I want you to be content. I want you to thrive.

I want you to take your fucking medicine.

Even if this number drops to $0 GAR, I’m still gonna do it, because it’s important work to do, whether it’s appreciated or not.

Nobody ever revolutionized an industry by giving people what they want, or even what they need.

They did so by giving them something they didn’t even know they wanted or needed in a way that suddenly made it all make sense for them.

There are plenty of people who will feed you convenient lies and false platitudes. Their bank account will always be fatter than mine because I deal in harsh truths.

There you have it. My strategy and journey to 101+ paid subscribers.

If you enjoyed this article, consider becoming a paid member. If you are a paid member, I recommend reading How to create a world-class Substack publication, How to get noticed on Substack, and How to get 5,000-20,000 new readers for your Substack publication every month to add context to this article.

If you are not a paid member, you can read everything with a 7-day free trial, or give us a one-time tip.