1k sign-ups or bust: how I grew my independent Substack "boozeletter" this year, and stuff I've learned along the way
This piece originally appeared on LinkedIn (lmao), hence the hed. I regret nothing.
This post originally appeared on LinkedIn. I’ve never written anything on LinkedIn before but I figured that’s where this sort of thing belongs. For those of you curious about newsletters, or this one specifically, I’ve reproduced it below.
On Memorial Day Weekend 2020, I published the first edition of Fingers, an independent newsletter I had founded a few days prior during lull in my workday. By founded I mean I: stewed about the idea for an inordinate amount of time, bugged the shit out of my fiancé and friends about it, then finally created a free domain on Substack (fingers.substack.com), doodled a bad approximation of a logo on a piece of scrap paper I had sitting on my desk, and ported over a couple small email lists I had sitting dormant in MailChimp. It me: founder.
With about 200 people—mostly friends and family—on the Frankenstein'd Fingers distro for its inaugural outing, I hit "send" on the piece, an essay about John Cheever's "The Swimmer," the American love affair with swimming pools, and a viral video of dipshits at a mid-pandemic pool party in Lake of the Ozarks. Just like that, Fingers was born.
Since then, I've published a new edition of Fingers pretty much weekly, mixing original labor reporting with author interviews, cultural commentary with freewheeling aggregations of beverage industry bullshit. If it was even vaguely related to drinking culture or being online, and it interested me personally, I pursued it. I didn't ask for any money from subscribers, because a) I wasn't sure whether I had enough interest in the subject or time in my schedule to to post regularly; and b) I wasn't sure what I'd even be asking them to pay for, anyway. Instead of money, I focused on just growing my list, setting a goal of breaking 1,000 free subscribers by the end of the year.
I sent out the final Fingers edition of 2020 this morning to 1067 subscribers. Mama we made it! The project has grown modestly but steadily over the course of the past seven-ish months, and I'm very grateful to everyone who's welcomed my demented, drinks-related coverage and commentary into their inboxes in that time. I'm hoping to introduce a paid-subscription tier of Fingers next year, and I've got some other projects on the horizon that will (ideally) dovetail with this one. More on that soon enough; by all means subscribe to Fingers to stay updated on the latest developments here at HQ.
In the meantime, here are some notes and things I've learned from publishing Fingers this year.
Growth comes in fits and starts—but collaborations help a lot.
I didn't start entirely from scratch when building the Fingers list. Like I said, I ported about 200 email addresses from a pair of personal mailing lists. I had no idea how many of those people would stay on once I started sending them this new newsletter, and at first there seemed to be a fair bit of churn. After awhile, though, things evened out, and I began a slow, steady, but sloooow march up and to the right on my subscription chart.
Here's the last 90 days of subscription data from my Substack dashboard. As you can see, October and November were a fucking grind. With every edition I sent out, I seemed to lose a handful of subscribers and gain another handful, netting out just a few steps further than where I'd started.
Then, in early December, I got two big boosts:
Luke O’Neil, the writer of (very good) newsletter Welcome to Hell World named Fingers one of his favorite newsletters of 2020 in a year-end review for The Discontents.
My piece about lessons learned from the failed union elections at Surly Brewing Co. and Spyhouse Coffee Roasts, two craft F&B businesses in Minneapolis, got some good pick-up amongst labor types on Twitter, and introduced Fingers to a bunch of new people.
These two events, the sum of which pushed me well over the 1,000-subscriber mark, are actually kind of related. O'Neil was gracious enough to trade emails with me here and there as I was getting this project going, so in early September, I pitched him on co-publishing a story about the union drive then getting underway at Surly. He ran that story in WTHW on Labor Day Weekend, which put me in front of his (much larger) audience and yielded a bunch of new sign-ups at the time. (Side note: Thanks Luke, everyone subscribe to WTHW, it's great.) The follow-up piece was purely a Fingers joint, but seemed to tap into a lot of the same energy of the first one.
I saw smaller but structurally similar boosts each time I was asked to be a podcast guest, which happened organically 4x over the course of the year. The lesson I take from all this is hardly groundbreaking shit, but still worth mentioning: crossovers/collaborations/whatever really can bring new readers into the fold, whether directly or indirectly.
No one wants more email.
Judd Legum, who publishes Popular Information, was another Substack power user who was kind enough to answer my early questions about the platform. He told me, pretty much verbatim, what O'Neil had: nobody wants more email.
Legum (along with researcher and frequent co-author Tesnim Zekeria) sends out Popular Information 4x a week, an absolutely inhuman velocity of which I am both awed and terrified. O'Neil publishes more sporadically but also puts out a truly staggering number of newsletters. Honestly, I think both of these very-different publications could publish like, half as much and still be totally "worth" their subscription fees (both of which I pay, by the way.) But what do I know? Their overarching point—that sending your audience more emails won't necessarily endear you to them any more, and may actually annoy the shit out of them—made sense to me then, and still does.
At Fingers, I publish like once-a-week-ISH. Sometimes more, usually a bit less. This works for me because I am doing Fingers very much as a side project on my nights and weekends; it also seems to work for my audience, who has not (yet, at least) demanded more frequent editions from me. The opposite is probably more true: in the few instances where I've sent back-to-back editions at too short an interval—say, two newsletters over 72 hours—I seem to see more unsubscribes than normal. So I try to avoid this, because in addition to hindering Fingers' growth, unsubscribes hurt my feelings, and I take them irrationally personally. Which brings me to my next point...
Stats are stupid, yet very difficult to ignore. Try to anyway.
People are going to unsubscribe from your newsletter! It will be a bummer! Try not to let it get to you!
I have not been very successful at internalizing my own advice. Maybe you'll have better luck. As my now-wife can attest, I have at times gotten a bit obsessive about Fingers' subscription growth, open rates, etc. It's a huge distraction. The newsletter's day-to-day performance has a remarkable effect on my mood and sense of self-worth; if it's up, I'm cautiously optimistic, and if it's down, I am fucking miserable. And I don't even make any money off it! I would make a terrible CEO; one bad day for the company's stock price and they'd find me in a broom closet in the fetal position.
What I'm trying to say is staring at Substack's dashboard after every newsletter you send is probably not a great use of your time. Said dashboard (at least, the one for people like me with no paying subscribers yet) is really straightforward, so there's actually not a ton to look at. I suspect this makes it even more appealing for audience-development neophytes (like myself) to sit there and stare at the performance of individual emails. For example, here's a recent Fingers story in the Substack back-end:
Like I said, not a ton to look at. Are these good numbers? Dismal? Who knows! This is a pretty typical outcome for Fingers editions, but the email before this got half as many views. I think that might have been due to the Gmail outage of mid-December, but maybe the subject line just sucked, or people were busy, or whatever. MAYBE ALL MY READERS HATE ME NOW?!?, I remember thinking at the time. And yet, next email, dramatically better performance.
Try not to catastrophize over the metrics day-to-day. It's just not worth your time, especially if you're just Substacking for fun. If you want to stress yourself out that much about day-to-day audience development, get a job at a media company, that's all you'll be allowed to do! (Just kidding, there are no jobs at media companies any more. But you catch my drift.)
B2B/trade stuff is probably a surer bet to $ than whatever you'd define Fingers as.
Some of the most successful writers on Substack publish newsletters that have direct applications to a specific business sector. There are some bona fide trade publications on there, plus a ton focused on start-up culture and productivity and #mindset. I thought about launching something like this for the beer industry (which I am somewhat credentialed to cover), but I realized doing B2B trade coverage didn't sound very fun at all. It would basically just be a job, and I already have several of those.
The dream, or at least one of my dreams, is to write only about things I'm interested in, when I'm interested in them, and to be paid handsomely for this. Sadly, that's not the way things work for 99.999999% of us pathetic humps who write "professionally" for a "living." Instead, I positioned Fingers in a lane where I have (some) expertise—the beverage industry and American drinking ritual/culture/practice—and looked for opportunities within said lane to write about shit I genuinely care about, be it labor practices, politics, memes, etc.
This makes for quite a menagerie of stories, styles, and formats, and probably isn't the best way to strengthen Fingers' "value proposition." Will people pay me for a hodgepodge of reporting, blogs, interviews, and aggregation that has no immediate effect on their approach to the beverage business? I don't know; we'll see. But I've had more fun doing Fingers than I would have if I'd taken an Axios-for-alcohol approach to this project, so that's gotta count for something. Right? Anybody? Dad?
Find ways to have fun that make sense for your "brand."
Because I'd already written off being a serious B2B newsletter, I made a conscious decision to avoid overly professionalizing Fingers. Consider the artwork. I hired my buddy Daniel Fishel for a logo and some basic graphics that I use in each newsletter, but besides that, all the artwork that appears on Fingers is my own doing.
As such, it is typically weird:
Bad:
Lazy:
Or weird, bad, and lazy, my personal favorite:
I do these in either Preview (on Mac) or Canva. I have no design experience, though graphic design is my passion. I get such a kick out of making these images, so when I get done writing a newsletter, it's a little reward to myself that I get to come up with one of these deeply flawed graphics. And since I'm not trying to appeal to professional beverage business bois with Fingers, I don't feel like I'm undercutting my credibility by fucking around with the visuals. Your mileage may vary, but the idea here is to look for opportunities to make your newsletter yours, rather than just what you think your readers expect. It'll probably make the project more fun.
Reader feedback is hard to come by.
It's hard enough to get people to pay attention to your writing, so if you're hoping that they'll regularly take the time to not only read but also respond to your newsletters, you're probably going to be disappointed. Substack has a comments function, and I'm active-enough on social media, but eliciting consistent response to my newsletters on those platforms in a way that approximates a "community" has definitely been a challenge.
More popular newsletters don't seem to have this problem. I've stumbled across Substack posts that have tons of engagement, and—with plenty of jealousy—tried to figure out what they're doing that I'm not. Creating compelling comment threads? Writing open-ended Tim Ferriss-brain #business posts? Just generally writing about topics that get people talking more? Probably all of the above.
To be fair, I've probably received a few dozen direct email replies to various pieces (not just from my mom, either, but shoutout to her!) Those are tight. And I so appreciate the friends and media colleagues who retweet my work and text me about turns-of-phrase that they got a kick out of. So I don't always feel like I'm blasting Fingers into the void... but sometimes, I very much feel like I'm blasting Fingers into the void.
Relentless self-promotion seems to help, but I don't know how much.
I don't have a ton to say on this front. I've always been pretty shameless when it comes to promoting my work on social media and in-person. I think it has helped me achieve some of my goals in the past, and I think it has helped me achieve my goals with Fingers too. But I don't, like, track this assumption.
I could: I promote Fingers on Twitter, Facebook, LinkedIn, and Instagram, and could probably set up some UTM tags or bit.ly links to see whether my posts there were driving meaningful eyeballs to the newsletter, and/or getting people to subscribe. This sounds exhausting, but maybe I should be doing it. Does anyone know how to do this with a minimal expenditure of brain power? Please advise.
At the very least, I don't think shouting out my own work has hurt the enterprise.
Newsletters are an art form I've yet to master.
I've been writing professionally for about a decade. I have never been a particularly succinct writer (witness: the sheer length of this fucking LinkedIn post) but writing newsletters has been uniquely challenging for me. Keeping stuff punchy, fun, and cohesive in this medium is tricky because you're trying to write good shit while also "optimizing" your newsletter (or at least, not completely de-optimizing it) for the delivery mechanism by which it gets to your readers, which is mostly on their phones. Who wants to read a long-ass post on their phone? Not me!
Obviously, there are exceptions here: Welcome To Hell World, for example, is typically so good that I will scroll and scroll basically as far as Luke O'Neil decides to let his editions run. Ditto a few others, like Fostertalk, a media gossip sheet/criticism blog published by my pal Foster Kamer.
I don't think I've really nailed the right length for Fingers yet. I'm hoping in the new year I can keep my editions column-length (i.e., 800-ish words) more often. Better for readers, better for me, just better!
***
That's all I got. If you've made it this far, clearly you are very interested in either newsletters, drinking culture, Substack, or me. I'm flattered either way. Feel free to message me on LinkedIn or shoot me an email (dave@dinfontay.com) if you'd like to hear more about any/all of this. And of course:
Self-promotion, bay-bee! Alright, goodbye.
