January 20, 2023

RIP My Inbox

Huge thanks to everyone who replied to confirm they got my daily broadcast yesterday 🙏

As I said in that message, I’m in the process of switching email providers and wanted to make sure I didn’t screw anything up.

As it happens, I DID screw something up... just not the thing I was worried about ;-)

Rather than people getting no message from my new provider (i.e., my actual fear), tons of people got TWO of the same message - one from my old system and one from my new system, about 30 minutes later.

My apologies about the double send, and thanks for all the hilarious and kind replies! I happily spent today manually responding to each and every one (695 and counting)

Among your messages, there were a few frequently asked questions. Here are the top three:

If you don’t care about any of these questions, you can stop reading now and come back tomorrow for more on market demand :-)

If you are interested (or morbidly curious), please read on...

Q: What email provider are you switching from?

Until this week, I had been using Drip for my opt-in forms and email sequences and Mailgun for sending my daily broadcast.

Q: What email provider are you switching to?


Q: Why are you switching email providers?

(Grab a beverage, this is going to take a while.)

Chapter 1: Drip

I’ve been a Drip user since about 2015. Back then (when Rob still ran it), it was very well suited to my needs. I loved it and recommended it to everyone.

Then LeadPages bought Drip, and then I think someone bought LeadPages, and slowly but surely, the product started moving away from being a good fit for me.

More and more features were added that I didn’t need, the interface got more and more convoluted, the performance got slower and slower, etc...

You get the idea.

Even though Drip was an increasingly bad fit for me personally as a daily broadcaster, it was still okay enough if I minimized my use of the product itself.

So I started using outside apps and automation to author and send messages through Drip without ever having to open the actual interface.

Then in 2022, my goal for the year was to automate everything possible about my business. Since my daily broadcast is, well, daily, removing all friction from that activity was at the top of my list.

I don’t want to bore you with the details of my daily publishing workflow, but it went something like this with Drip:

  1. I would post an article on my website
  2. The article would get added to a secret RSS feed
  3. Drip would see the new article in my RSS feed
  4. Drip would create a draft email message based on the article
  5. I would log into drip and send the message

That last step drove me crazy.

It usually only took a couple of minutes, but the Drip UI for it was slow and clunky (and seemingly kept changing every couple of months).

Furthermore, Drip still hasn’t updated the UI to be mobile-friendly, so even the simple act of sending a draft message was very difficult to do from my phone.

For me - Mr. Mobile Web - this was a big pain point.

I mean... I could very easily write and publish a new daily message with my phone from virtually anywhere. Then I’d have to get up and go find a laptop with an internet connection (or tether it to my phone) and navigate through four or five screens in Drip merely to click a SEND button.

Worst of all, I had to remember to do it, which I sometimes didn’t if I got distracted in the middle by the kids or dogs or whatever. I’d remember that I wrote and published the article on my phone and forget that I never clicked SEND in Drip.


All of this frustration - plus my annual goal of automating everything - was enough to make me look for an alternative that would automatically send out the email as soon as it appeared in my RSS feed.

Which is where Mailgun comes in.

Chapter 2: Mailgun

I wouldn’t be surprised if you had never heard of Mailgun. It’s not exactly considered an alternative to Drip.

“Drip” is to “Mailgun” as “Microwave Oven” is to “Large Hadron Collider”.

In other words, Mailgun is not for the faint of heart.

For example, you can’t even write a message in Mailgun. You write it somewhere else and send it to Mailgun with the API.


I knew MG was WAY more than I needed, but it is delightfully developer friendly and is very much capable of sending out messages in real-time based on an RSS feed which was my goal.

So I configured a bunch of things in MG, wrote some short but arcane PHP-based endpoints, and set up Zapier to trigger the endpoints when new articles were published in my feed.

With that in place, I configured Drip to move new subscribers to Mailgun once they completed my orientation sequence, and BOOM! Drip was handling my forms and automated email sequences, and Mailgun was sending my daily broadcast automatically in real time without me having to remember to log in and click a SEND button.


. . . .

. . .

. .



It turns out there are some real difficulties with having two email providers handling your emails.

For example, unsubscribes.

When someone unsubscribed, I had to make sure they were unsubbed in both systems.

I knew this going in, but I thought that once someone was moved from Drip to Mailgun, I could just delete them from Drip. And that’s what I did.

But it ended up not being that simple.

For example, someone could have made it from Drip onto my daily broadcast in Mailgun and then LATER subscribe to a new campaign in Drip. This resulted in the same email address being in both systems, which I originally had (foolishly) thought would never be the case.

This scenario was actually quite common because lots of people on my daily broadcast (in Mailgun) would add their email addresses to a notification campaign for an upcoming workshop (in Drip).

Not only did this get quite confusing when it came to unsubscribes (and other things like when someone wanted to update their subscription to a new email address), but it meant that I was paying twice for this non-trivial subset of subscribers.

Not a huge expense on its own, but definitely sub-optimal.

Speaking of paying...

It turns out that unlike Drip and most other email service providers, Mailgun charges by the number of messages sent, NOT by the number of subscribers.

This is a significant distinction for someone who sends tens of thousands of emails per day, which works out to more than three-quarters of a million messages per month.

Here’s what I mean...

In a subscriber-based billing system, I get charged the same whether I send daily or weekly.

In a message-based billing system, I get charged seven times more if I send daily than I would get charged if I sent weekly to the same number of subscribers.

Long story short, Mailgun gets expensive for daily emailers.

With something like 35,000 subscribers between Drip and Mailgun, I was paying around $1,000 a month combined.

This is not a deal breaker considering that my daily broadcast is the heart of my business, but when I have a recurring monthly bill with a comma in it, it gets my attention :-)

The combination of the cost and the complexity of having addresses in two systems inspired me to take a fresh look at ConvertKit.

Chapter 3: ConvertKit

Let’s start with the money because it’s simple:

For 35k subscribers on a daily list, ConvertKit is roughly a quarter of the cost of Drip + Mailgun.

Again, this is because ConvertKit bases its prices on the number of subscribers, not the number of messages. So, in theory, I could email the entire list ten times per day for the same price as once per day (or once per month, for that matter).

But more importantly, I get all the subscribers into the same system, so I don’t have to write custom code to handle unsubscribes, address updates, template changes, and a bunch of other little things that - turns out - add up to a big PITA.

Okay, but...

Why didn’t I just move from Drip to ConvertKit instead of Mailgun back when I made that decision?

Great question!

The answer is this:

At the time I chose Mailgun, CK didn’t have (or I couldn’t find) a feature that would AUTOMATICALLY send an email to a list in response to a new item appearing in an RSS feed.

I knew it could create a DRAFT from an RSS feed in ConvertKit, but Drip already did that, and it wasn’t worth migrating to CK if I still had to click SEND on a draft message.

After living with the costs and drawbacks of the Drip + Mailgun solution for months and then learning that ConvertKit COULD send automatically from an RSS feed, the move to CK was a no-brainer.

Here’s the thing...

This message has gotten even longer than I expected, so I’ll stop now.


If you’re thinking about starting a BRAND NEW email list, I’d recommend using ConvertKit. This recommendation may (will probably?) change in the future, but in 2023 at least, CK is the best fit I’ve seen for people building an expertise-based business.

That said...

If you ALREADY HAVE an email list on Drip or Mailchimp or something similar and you are reasonably happy with it, I’d probably stay there because migrating is a pretty big undertaking.

If you have specific questions about any of this, please feel free to hit reply and ask.

And hopefully, you don’t get this email twice :-)