Check-out any time you like?

California Hotel, by Sonny Abesamis, CC BY 2.0

September 10 update: as it turns out, the following post turned out to be a draft of the first email I sent out via a new-to-me newsletter provider. You may read the more refined piece over at the new home for my newsletter On Management, where I do most of my bloggity writing these days .

Last night I dreamt that my email newsletter, On Management was (already) up and running on Ghost. I haven’t published in a little over a month.

I’ve been running email newsletters on and off since the late 1990s. Originally, from my email client, RIP Eudora. In the late 00s, I sent out quarterly notes, using Constant Contact. There was a curation experiment in the early ‘10s, RIP Bitly Bundles.

I’ve published evolving iterations of On Management since 2015. I’ve used Mailchimp, Substack, and Buttondown.

The tl;dr is that I’m moving my newsletter to Ghost, where a version of this post will be the first email I send out. Some time after Labor Day.

I’m excited to get tools (content tags!) that better align with the way I write the newsletter. If the conversion process I’m now working through is any indication, I’ll also have more robust and engaged support than was possible from Substack or Buttondown.

(Mailchimp support for paid folks absolutely rocks. They’re also an apparently-profitable 20-year-old company with hundreds of experienced employees.)

Subscribers to On Management know that I send emails a couple of Sundays a month. I think the dream was my anxious wish that I’d be ready to send something out this weekend, after this long and conversion-related break.

The remainder of this post may be of interest to supporting members of the newsletter who pay to receive it, and/or newsletter and operations nerds.

Tl;dr for supporting members of the newsletter, if you’re reading the blog. Some of you received a notification that your subscription has been canceled. Others may receive such a notification, as I will not be able to move all of the paid subscribers to Ghost. I will make everyone whole, one way or another. I apologize, and thank you for your endurance.

Now, the part for the newsletter and ops nerds.

This has all been an absolute mess. Leaving Buttondown after leaving Substack has given me an insight about what made the mess. It’s a hypothetical insight. As such, it’s based on experience and inference. It may or may not be accurate.

The problem, as I see it, is with Stripe. You may know Stripe, a tech company that provides of many of the “frictionless” payments you’re making on the internets.

The problem is not Stripe itself. Works great, 10/10, would do business again.

It’s, hypothetically, that Stripe is an enterprise product. It’s meant to be used by companies that have teams of programmers who tirelessly integrate Stripe’s product with the company’s systems, so that the company can be paid.

So, paid newsletter companies like Substack, Buttondown, and Ghost serve as virtual teams of programmers for people like me, who can be paid, after simply connecting our Stripe accounts to the newsletter service. Boom.

The friction in these frictionless payments happens behind the scenes.

Because, hypothetically, like Tolstoy’s unhappy families, each newsletter company has its own way of integrating with my Stripe account.

The Anne Libby Stripe account shows unique customer accounts for every paid reader. Leading Anne (aka me) to believe newsletter providers saying, they’re your readers, you can leave any time, and take them with you.

Bear with me, ops and newsletter nerds. It gets knotty.

A reader’s friction-free purchase of a newsletter subscription appears to create a customer account in Anne Libby’s Stripe account, and charges them for the subscription product they purchased. The product corresponds to the subscription price quoted at the time of purchase. The product, hypothetically, may be unique to the newsletter provider.

Example, one of my business values is to increase prices for my services every year. I work for myself, and nobody else is going to give me a raise. And, the newsletter is part of my business, where I see expenses go up every year. (Hashtag, capitalism!)

  • So, 2018 Substack readers bought a different Stripe product — unbeknownst to me — than 2019 Substack readers, because they paid different prices.
  • In my early Substack days, I experimentally offered discounts, which involved Stripe coupons. Each discount offer apparently created different Stripe products.
  • Pre-Substack, I used Moonclerk as my Stripe payment processor. Early paid subscribers frictionlessly purchased unique Stripe products when their payments were processed by Moonclerk, which was never connected to any email service.

Hypothetically, different Stripe products at different prices — and possibly different Stripe-newsletter company/payment-processor integrations — do not lend themselves to automated conversion from one provider to the next.

Indeed, last month, as a final step in my extended conversion to Buttondown, with everyone “on Buttondown,” I closed seemingly redundant Moonclerk accounts for pre-Substack readers, to prevent double-charging anyone. I did this while in communication with Moonclerk support, and thought I was golden. However, though there was no relationship between Moonclerk and Stripe, closing those accounts triggered something at Stripe. Success? Nobody was charged twice — these readers were unceremoniously unsubscribed by Buttondown from their paid subscriptions, and won’t be charged at all. (Even though Moonclerk and Buttondown have never had anything to do with one another. WTH.)

Ghost’s conversion team has told me that that they can only convert member (paid) accounts that are currently being charged at the price I establish for subscriptions at Ghost. (Humming “Hotel California” rn.) Kudos to the folks at Ghost for not just telling me, “No problem.”

The bottom line is that some of the member (paid) accounts will not convert over to Ghost. And I’m worried that when I disconnect Buttondown from Stripe, more people will be unsubscribed.

I’ll take manual steps to be sure that everyone receives the correct level and term of subscription, and/or issue pro-rata refunds as necessary. If any of the supporting members happens to be reading this on my blog, I’ll be in touch with you directly after the conversion.

And true story, one of my goals with this newsletter was to write some weird and insightful things. Which I hope to get back to after this hopefully last conversion*.

While I never thought I’d stop consulting and coaching to make my newsletter a full time job (lol) my other goal has been to develop my newsletter, over a multi-year period, into a small but meaningful line item on my income statement. Over the last several months, my time that would have gone into working on that side of the newsletter has gone towards a lot of conversion stuff. And for the last month, so has the time I would have spent actually writing my newsletter. It has not been friction free.


(*It is certainly my last conversion to any service standing between me and Stripe. I also see Stripe working to service folks in the no-code space. If this is you, I’d say, be sure that you know how Stripe customer accounts and products actually work. I’m still not sure that I do.)

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