Q&A with Ann Friedman: “What is good about being truly independent that I’m always thinking: Is this the way I want to do it?”

Within the individual newsletter economy, you can pretty much trace the lineage of any highly curated ‘stack back to one of the internet’s foundational ‘letters: The Ann Friedman Weekly. Which makes this week’s interview with Ann Friedman — about her earliest models for the newsletter, the non-glamorous details around building an independent subscriber and classifieds business, and her ambitions for its next form — both a long-awaited revelation and tactical blueprint. Enjoy! 


So first, I want to say congrats to The Ann Friedman Weekly on recently turning 8...

She’s in second grade! Or maybe third.

...which means you started it back in...2013! That’s basically lightyears before our current newsletter renaissance. Was there anything you looked to as a model for the newsletter back then?

It still did feel at the time like everyone had a newsletter — it was the TinyLetter years. It’s hard to compare to now in terms of volume, but it did feel like I was joining a crowd of people and not like I was doing a weird solo thing even in 2013. 

Model-wise, I had long been a fan of the Harper’s weekly email. Harper’s Magazine sends a weekly digest written in paragraph form that’s like, here’s what happened in the week, with one sentence for each news item. Harper’s being Harper’s, nothing is hyperlinked, so I would often read it and copy-paste sentences to Google for the full item. I really liked that paragraph format; I stole that and obviously included links. In general, I wanted my newsletter to feel like a magazine’s front of book. 

When did you move off TinyLetter?

My TinyLetter was ugly as hell. It was always reformatting my paragraphs, so it wasn’t like I was sad to leave it, but the real inspiration was that I got too big for it. TinyLetter back then had a cap of a few thousand subscribers [editor’s note: now it’s 5,000]. I hit that cap pretty quickly and then emailed TinyLetter personally and was like, will you give me more, and they said yes. 

But they wouldn’t keep raising the cap indefinitely, and so I upgraded to using MailChimp in 2015. But MailChimp cost money, so that’s when I was like, I’m going to have to start charging. If my newsletter had stayed small or it wasn’t costing me money, I would have done it on TinyLetter forever. 

And you’re still on MailChimp now?

Yes. I love that you can’t easily tell that I’m on it. I’m not endorsing MailChimp by using it. It’s just a tool I use; I will maybe use a different tool in the future. It’s truly just the pipes through which I push my stuff. 

It’s funny because with Substack, obviously, you can tell when a newsletter is on that.

Look, I give my money to MailChimp, and if MailChimp did something I was really opposed to, I would look into switching providers. But I don't feel like I'm a brand ambassador for MailChimp. Meanwhile, Substack is like, these are our writers. This is a leaderboard of our writers.

I’ll be honest with you. If Substack existed as an option in 2015, when I was like oh shit I’m too big for TinyLetter and there’s no payment processor plus email option, I would have just done it. But I’m really, really happy to not be brand-associated with any platform. 

How long did it take for you to set everything up on MailChimp?

The transition from TinyLetter to MailChimp was nothing. It took me like a day with MailChimp customer support. The email service provider with the payment processor layered over the top is the hard part.

The reason is this: there are lots of software options if you want to start charging people and put them on a list when they sign up. There are not a lot of options if you already have a list — some people who are paying you, some who aren’t, and they might float back and forth between those two statuses — so you need something that updates their status to “paid” or “unpaid.” So instead of adding a subscriber to a new list, I needed software to update the status of a particular subscriber on my existing list. And that is the thing that did not exist way back when. That is the thing Substack makes really easy, and even now, membership software doesn’t all do that very well.

I use a payment processor called MoonClerk. It’s really cheap. Like really cheap. Then Amina [Aminatou Sow] introduced me to this woman Jacque Boltik, who you should very much know. Jacque is a tech genius who specializes in newsletters — she managed newsletter tech at the LA Times and designed a bunch of early independent newsletter templates, like Lenny Letter. 

So Jacque wrote me some Python code to make MoonClerk, a payment processor, talk to MailChimp and update the list. So every Friday, before I send the email, I run a snippet of Python code to update MailChimp and make sure every user is tagged as paid or unpaid.

Oh my god! You have bespoke code.

Yeah! It was the only option back then. If you asked me in 2015, are you happy that you have to learn about all this shit? I would be like no! I just want to do my job! But I have to say, I feel like a different kind of business person in that I have to understand all these tools. 

How do your classified ads fit into this? Is that a different layer?

Yes! The problem was that I didn’t want to email with everyone who wanted to buy an ad. I wanted an online checkout system so people could buy whenever. So I ended up using Squarespace Commerce and creating a digital product — when you make commerce items in Squarespace, it can be a physical product/service or a digital product — and the “item” was the day the ad would run. 

This Friday is April 2, so I’d make the item “April 2” and make six of that item for the six slots in the classifieds. Squarespace allows you to create a form in the checkout, so I said in the form, put your ad text here.

Then I have an assistant who receives the receipts when people buy an “item” and logs them in a spreadsheet based on date. So on Friday, I look at that spreadsheet and see the exact text of the ads for this week. That way, it’s automated in the sense that people can buy an ad in the middle of the night, but there’s a human — my assistant — who’s looking at them to make sure it’s not something offensive and the links work. I pay her $30 an hour, and it’s less than two hours a week that she spends on the classifieds. It took a while to ramp up, but I’m now sold out six weeks in advance, always. 

This is blowing my mind. My method is...emailing with every single person and putting it in a sheet.

Noooo Delia! [Laughs]

I’m learning so much.

Squarespace Commerce! I swear to god.

Also, I have to say about classifieds — when I had this idea, I emailed the people I knew who had independent newsletters, and I was like what do you think? And they were all like, it’s too much management. Just do banner ads. I’m glad I didn’t listen.

Wait, so now I’m trying to figure out if you’re the first newsletter that ran classifieds.

Obviously, this is how print publications paid for themselves for years. Like, lots of low dollar ads is not my personal innovation. But it is true that before I started my classifieds section, people were like, “Banner ads! Those would be better.” [Editor’s note: this is the part where we laughed long and hard]

But I am fairly certain that there was not another newsletter with classifieds before mine, because there was no one else to ask about it back then. 

Is there a reason why you wanted to do classifieds over, say, banner ads?

I had a sense that it was my peers who read the newsletter, not people who were controlling marketing budgets for major companies. At the time I started doing this, I had 25k subscribers, which is a lot in Newsletter Land, but not a lot in Corporate Advertising Land. It just felt more like in sync with who was reading and who would be more likely to advertise. 

Nowadays, what’s the biggest challenge of running an independent newsletter? 

I would never sit here and tell you that on a level of tech, my system’s the best. My system is held together with paper clips and scotch tape. But I keep my scotch tape/paper clips system, because if I were to pay more for a tool like MemberSpace, I would have to charge more. 

I weigh factors like, am I undercutting myself in this weird gold rush market? I have a lot of questions about pricing. I do sometimes feel like a sucker because I don’t want to charge $30 a year. There is a constant re-evaluation that is difficult, but what is good about being truly independent that I’m always thinking, is this the way I want to do it? Is this the way I want to run my business?

Ultimately, it's the slow road. I feel like there's always too much time lag between when I decide I need to make a change (use new software, up my prices, redesign my template) and when that change comes to fruition. One example: I worked on the initial paid-membership and classifieds plan (setting up Squarespace commerce, Stripe, and MoonClerk) for most of 2015. MailChimp gave me the first year free (because I was a TinyLetter power user, and because I asked them!), so then I had 12 months to figure out how to earn enough to cover the costs of the software. My 2015-16 budget info is at the bottom of this announcement post. I spent a lot of my time doing unsexy tech and business things throughout those years. 

Plus, if something breaks, you have to fix it yourself, right?

Well, if something breaks, I send a panic text to Jacque. Jacque’s current startup, Yellow Brim, built the email production workflow that Ben Thompson uses for Stratechery, and they have this forthcoming newsletter software called Osmosys, which is going to be amazing. It’s more for established publishers, about easily converting a web page into a beautiful email.

So Jacque is a very busy person, but she’ll always pause and help me when I’m in panic mode on Friday a half hour before the newsletter goes out. We have a collaborative relationship — me from the editorial side and her from the tech side — so in that sense, it doesn’t feel like I’m on my own trying to troubleshoot with a bot. That’s a real reward, to build relationships with humans who are not the customer service department of an app that’s making money off of me.

This actually leads into my last question. To me, reading your newsletter is like reading the tea leaves on what direction newsletters overall can go, and last month, you announced the first Ann Friedman Weekly writing fellows. It made me wonder if we’re about to see individual newsletters take on the role of indie zines. Is that something you’re interested in, turning the newsletter into something larger and less synonymous with just you?

Maybe! One of the great things about being fully and truly independent is that this project can evolve in whatever direction I want. That feels really good. I’m working on a redesign — Jacque is making me a new template that does feel a little more magazine-y. The first two writing fellows are about to start publishing their work in my newsletter. But mostly, the fellowship is a way to acknowledge the amount of power I’ve accrued our industry and redistribute some of it. The editorial direction is evolving to complement other goals I have. I want to better use the power that I have, and that might look more like a magazine.


Deez Links is a weeklyish newsletter written by delia cai.

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