A Tale of Two (Email) Cities


This has been a unique week for Now I Know — chaotic, at times stressful, but ultimately, going in the right direction. Here’s the back story.

If you write an email newsletter, you can’t just put everyone on bcc: and send from your normal email address. You have to use a professional service; otherwise, the spam filters are going to destroy you.

They destroyed me anyway. This is that story.

I’ve been using Mailchimp for the first 13+ years of Now I Know. On Tuesday, I shared the news that I’m shifting Now I Know from Mailchimp to beehiiv, and the reasons why.

What I didn’t share is why I made the switch this week. I had been planning to make the move for months and had decided to do so starting Monday, January 22nd. But for reasons unclear to me, starting a few weeks ago, Mailchimp had a problem delivering the email to about 15% of the people on my list. Over the long MLK Birthday weekend, I received a few dozen emails from readers, telling me that they suddenly, and inexplicably, stopped receiving Now I Know. Here’s how the rest of my week went.

Monday, January 15, at about 3 PM

I was really frustrated with the problem I was having with Mailchimp. And I knew that switching to beehiiv would fix that problem. So late Monday night, I decided to make the switch early.

I had a note ready to go to tell you all about the switch. I had planned on sending it on Friday (that is, today), as it works in this “Weekender” format, but the calendar didn’t allow for that. So I followed up the three-day weekend with a random note, but whatever — audentes fortuna iuvat, as it’s said (I guess).

Tuesday, January 16

The Tuesday newsletter went to you through Mailchimp. The Wednesday one was going to you through beehiiv — and that took a lot more work than you’d think. I needed to import some subscribers over. I updated my website so that new subscribers would subscribe via beehiiv, not Now I Know. I set up an automated series of emails to welcome these new readers to the list. I created a test page on my site to make sure all of this worked right. There was one wonky thing, but I came up with a workaround. This took about four hours.

The story about the platypus? I wrote it — in beehiiv — a few weeks ago. It was ready to go, and everything else with the transition had gone basically fine. I was ready to go. I scheduled the platypus story to go at about 9 AM the next day and asked my support team at beehiiv if they had any last-minute suggestions. They did, but I didn’t listen (oops!). Whenever you send emails through a new service, you need to train all the email servers out there, letting them know that your newsletter is legitimate. A good way to do that is to only send to about 25% of your list, and send the email to the other 75% of the list through your old service. Given the issues I was having with Mailchimp, and given that I was already kind of tired, I just went for it — I scheduled Wednesday’s email via beehiiv, sending it to the entire list.

Wednesday, January 17, AM

The spam filters won. Most email services dumped Wednesday’s email in your spam boxes; some email services just filtered it out entirely. I went into panic mode. The worst part was that, as this point, there wasn’t much I could do.

Wednesday, January 17, PM

The beehiiv team looked into the problem and said, yeah, I probably needed to do that 25%/75% thing. So I created a segment of basically random readers on Mailchimp and reconciled that with the beehiiv list. Then, on Mailchimp, I send those 25% a note saying that the platypus email probably went to their spam box, with some instructions on how to fix it. That’s all I could do — and it wasn’t much — until that night. The panic continued.

Wednesday, January 17, Late Evening

I decided to not only take beehiiv’s advice, but also, to eliminate everything I could from Thursday’s newsletter that could possibly trigger up a spam filter. No ads, few images, only a handful of links. All good and not too hard, but easier with a re-run than something new. I actually had an email ready to go for Thursday but decided not to risk it.

This is where things got a little crazy (and why this is a tale of two email cities). I actually sent three different emails out yesterday — all the exact same story. Most of you got it via Mailchimp. About a quarter of you got it via beehiiv. But then I realized that the beehiiv version was geared toward long-time readers, and over the last few days, I had a handful of new readers join the list. So I wrote and scheduled modified version of the beehiiv version to them, using beehiiv.

Thursday, January 18

Last minute, I had the (brilliant, I think!) idea of asking you (unless you’re a new subscriber) to reply to the emails I sent, all in an effort to teach the spam filtering machines that the newsletter isn’t spam. All together, I think it worked. There was a new problem — explained in the Week in Review, below — but thankfully, it had nothing to do with the spam avoidance ordeal.

I kept an eye on the numbers and on your replies throughout the day, and it looked like I was on my way to beating the spam filters. I’m not there yet, so I decided that for Friday — this email — I’d do more of the same: 25/75 split, testing ads here and there. And I’ll do the same for Monday and maybe Tuesday of next week, too.

So, thank you for all your patience! We’ll get there.

The Now I Know Week In Review

Monday: No email — MLK’s birthday.

Tuesday: The Great Now I Know Transition of 2024: The note that explains more of the above.

Wednesday: The Pregnant Platypus With a Secret: This probably hit your spam folders, which is too bad because it’s a really good story.

Thursday: The Greatest Thing Since 1928: A brief history of sliced bread. Also, another cause of my panic. If you clicked the “From the Archives” story in this one, you received an error that said, “There has been a critical error on your website.” That’s not a good thing! But thankfully, it was something easy for me to fix. If you want to read the From the Archives story — it’s about the history of “reading them the riot act” — you can, here.

And some other things you should check out:

Some long reads for the weekend:

  1. The First Responders” (Atavist, 41 minutes, June 2019). The subhead: “The black men from Pittsburgh who made up America’s original paramedic corps wanted to make history and save lives—starting with their own.”
  2. How ‘Racism’ Made Its Way into the Dictionary” (The Atlantic, 9 minutes, September 2020). The title on the Atlantic’s website is different than what I have here but the website’s “title” tag uses what I wrote, so, good enough. Anyway, this is a fascinating story — I had NO idea that the word “racism” was so new.
  3. Mean Girls: The inside story of the hit movie, told by the non-plastic cast” (Cosmopolitan, 18 minutes, April 2019). An oral history of the movie, told by some of the minor characters (sorry, Damien) in the film. I hear the musical version of Mean Girls that is in theaters now is mediocre, which is too bad, because the original is great.

Have a great weekend!