Requesting email newsletter advice!

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Do you have professional expertise with email newsletters? Perhaps you can advise me!

Compared to social media — and the algorithms that control what you do or don’t see in your feed — email has classically been considered a safer, more reliable way of reaching readers.

However, you still have to GET your email into the inbox of your readers, and I’m finding that harder than expected these days.

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In 2025, my ambition is to return to publishing new Wondermark comics on a regular, consistent schedule. In preparation for that, I’ve been blowing dust off of things and seeing what still works and what needs to be fixed.

My goal is pretty simple: to have a website where you can read my comics, and to provide my comics to you in convenient ways!

Some individual sub-functions of that effort have used third-party services, which have come and gone over the years, and so I’ve been trying to find replacements when necessary.

One key thing I’m troubleshooting right now is email delivery of my comics.

This (WordPress) site generates an RSS feed, and ages ago, you could plug that feed into Feedburner and it would send out an email to your subscribers on any day there were any new posts created.

Then, Feedburner was bought by Google, and of course that meant it was eventually shut down, and now that service no longer exists. So, the goal is to replace that functionality.

Options I’ve considered so far, and what I’ve learned:

• There is a one-for-one replacement for Feedburner called FeedPress. (You can sign up for the beta-testing FeedPress version of the Wondermark newsletter here.)
  
  It does exactly what Feedburner did, with one major downside: The FeedPress mailing servers do not appear to be widely trusted by spam filters, so there is no guarantee that the emails will actually make it into every subscriber’s inbox.
  
  This is my initial observation about the service based on some limited testing — if that proves to be true, I think that’s a fatal flaw.
  
  It is not a free service, but the cost is reasonable and within my budget.
  
  
• Mailchimp and similar email providers also offer RSS-to-email functions. I find myself in a double-bind, though, because my email list is large enough (~5k) that Mailchimp would be a $100+/month outlay, and it would only increase from there.
  
  If that cost is unavoidable, it’s unavoidable; but I’m trying to explore all options before committing to that, since ideally this would be a commitment for the long term.
  
  Every other email provider in this class seems to be roughly the same cost (including newsletter-focused providers such as beehiiv and ButtonDown).
  
  I do like Mailchimp’s robust tools for segmenting and so on.
  
  
• Notable exception to the above blanket statement is ConvertKit, which has a free tier up to 10k subscribers… But this free tier does not support RSS automation. This means every email would have to be manually created.
  
  And their goal, of course, is to lock you into their ecosystem if/when I exceed the threshold of the free tier — but perhaps by then I’d be back into the swing of things here, with a more reliable income stream again.
  
  
• If you’ve been getting my emails over the past year or so, you’ve been getting them from Sendfox, which is a pay-once provider (rather than a monthly subscription).
  
  That felt like a great solution at first, except that recently I’ve run into some troubling hiccups with their service that has me rethinking sticking with them for the long haul.
  
  Additionally, using their service requires drafting a manual email for every single update, and over the past year I’ve realized that what I really want is an automated solution.
  
  
• I think there is probably a way to use an app within WordPress to send out emails directly from the blog.
  
  This would involve hitching up an app to a third-party mailing server such as MailerSend, and I am not familiar enough with that process to know what it involves or whether it is a good option.
  
  The costs involved appear to be similar to a service like Mailchimp.
  
  
• I use Shopify for my online store, and customers who opt into the newsletter at checkout are one main source of new subscribers.
  
  So I briefly considered whether there might be a way to use Shopify’s marketing tools as the entire newsletter platform. I imagine it would once again mean drafting manual emails each time the WordPress site updates.
  
  
• Finally, some cartoonists are starting to use Substack as a newsletter platform, meaning that becomes a mirror to their main blog, and their subscribers are reached through Substack instead of via the WordPress blog.
  
  Substack is another potential source of exposure and new readers, but once again it means duplicating everything onto another platform, and also, I don’t care for that platform much personally.

Making the choice

I want to figure this out once and be confident with the decision. The ideal platform is:

• Cost-effective — it’s a free service I’m providing to readers, after all.
• Reliable — the whole point is for subscribers to actually get the emails they’ve asked for. This factor seems to depend a lot on the particulars of the sending servers.
• Simple — automated via RSS would be really great, but I would also accept a Zapier or similar automation that generates emails from the RSS automatically.
• Flexible — custom segments and the like are nice. My main complaint with Sendfox is that they control the parts of your subscriber list that you can send emails to, and yet have no useful tools for segmenting your list yourself. Super frustrating!!

I guess the point I’ve come to now is: I only know what I know so far, and I’m not super happy with what I know. It doesn’t yet point to a clear choice.

I would love to hear from anyone with good ideas in this realm who can give me their best advice, or some kind of sanity check on whether I’m considering the above in the right way.

Or do you have experiences with any provider mentioned above that you can share, positively or negatively?

ALTERNATIVELY, if you would like to become a SPONSOR of my email list to help cover the cost of one of the more reliable solutions, I would consider including SPONSORED MESSAGES in the emails while also providing ABSOLUTELY NO GUARANTEE of their effectiveness in terms of ROI or whatever!

The way to reach me about any of the above topics is, of course, email: dave@wondermark.com

I figure there’s got to be smart people who have already been around the block on this, and I would love to hear from you if you have!

(Comments is yet another thing I’ll have to figure out how to fix on this site.)