How I grew this newsletter from 56 to 2,177 subscribers in less than a year
i know the title is clickbait but i'm told that these sorts of posts 'do numbers'
I, Alex Dobrenko, by the power vested in all of you actually, have somehow amassed a readership of 2,177, which just so happens to be the exact number tattooed on my arm:
The room where it happened:
I started writing regularly in February 2022. At that point I had 49ish subscribers, all of whom were my dad.
Knowing myself to be a scrappy little overachiever — an energy I did NOT want to bring to my writing here — I set a VERY MODEST goal of reaching 200 subs by the end of 2022.
It felt doable but, more important for me, it felt sorta non-existent. It implied that GROWTH was not the point, which gave me space to have fun. To goof. (fun fact my original blog was called goofing with friends RIP).
And now, less than a year later, we are 2177 strong!! And though that number is impressive — you should see the ladies at the bar they go nuts and ask if I want to “get outta here” but usually they make the bouncer ask me which is like so weird — the truth is: the most challenging parts of the last year for my fragile psychosocial headspace were when I most cared about the numbers. They are a false god, like Pepsi, and do not deserve the time nor care we so often give them.
What does matter, and what makes me feel the least bad, is the actual readers. Getting to know y’all in the comments, hearing that my lil word barfs meant something to you? That matters.
A lot of y’all write me in response to my ‘welcome to the newsletter’ email. Though I don’t always respond right away (I owe a good amount of you responses actually, those are coming soon I promise), I do read them all RIGHT AWAY because I am a grubby lil sicko. In just the past few days, there have been several that all basically say: “I like writing, but I stopped. your writing makes writing seem fun again.”
That melts me like a grilled cheese sammich. Numbers can’t melt people.
(oh actually there’s a lil tip right there — ask for ppl to respond in your welcome email. A good chunk actually will which is a great way to get to know who the heck is reading your newsletter.)
Some people even pay!
This is great. Y’all are great. A small percentage of you — 63 human people — EVEN PAY FOR THIS which is the greatest. Whenever I’m glum, my friends remind me ‘strangers are paying you money because they like your writing.’
It is sad, that the money is The End All Be All proof, but hey, as Adam Smith once said, “show me the money!” (later on he said, and this is no joke, “you had me at hello.”)
Seriously though — imagine if we arrived anywhere 64 people strong (I’d be there too)? Everyone would be like wow, that’s a lot of people, we’re gonna need to keep an eye on them.
And I don’t even offer any real perks (yet) - that’s all gonna change this year though.
Let’s get to 100!
Speaking of... OH MY GOD NO HE IS NOT GOING TO ASK FOR PAID SUBSCRIPTIONS IN THE MIDDLE OF THIS HEARTFELT...I did want to quickly mention - you can become a paid subscriber of Both Are True. Why?
Mostly because I want to have one of those orange checkmarks that says “hundreds of paid subscribers.” We are currently 37 people away. We can do this. So if you’ve been on the fence or something, get off the fence who the hell wants to be ON a fence that is ridiculous.
But also because it really does go a long way in supporting this little dream of mine, especially when nighttime comes and Lauren says “Al, let’s look at the finances,” and I just pull up the # of paid subscribers and she goes, “that’s great, hun, but it isn’t really enough to-” and then I cut her off and scream - ‘THESE ARE MY FANS’ and she moves to a hotel.
Anyways. Let’s get to THE LEARNINGS.
#1 write good
This is the most important thing and also the hardest thing, because its….really hard. So let me just share this one piece of wisdom at the core of my upcoming book tour (no book, just a tour): make your writing good.
I don’t know? I guess my north star has been to just be as honest as I can possibly be without upsetting my parents.
Talking about my approach to writing - besides being the most boring fucking thing this side of CSPAN - would take much longer than I’ve got here, but I will say one thing, less about writing and more about how I got here (my life had, in fact, been turned upside down).
I was trying to be a stand up comic. A goofball like Rodney Dangerfield. Take my wife, please! No seriously, take her to the hospital, she’s bleeding.
And then we had a child. A human child who woulda never forgave me if he one day learned that papa missed most of his childhood hanging in random dudes’ backyards waiting hours for 3 minutes of stage time performing for other standups all of whom hate me / are looking at their phones / etc. No disrespect to the open mic circuit, y’all are warriors, but I just couldn’t justify it.
So I thought - hey ok, what if I did standup, but on Substack.? Like what if I treated each post like a lil stand up set?
I dug this strategy because it went anti-wheat, aka against the grain, of what everyone else is doing. So on Substack I’m competing with a lot less standups, so it’s easier to be noticed? I don’t fucking know. This is starting to sound like a 3 hour podcast CUT IT LETS CUT.
But what posts did good?? Crazy that the top post by ALOT is still Messy Ass Spaces, which I published to only 350 peeps. More on how that happened soon.
#2 motivation, like Tom Hanks, is Big
I’d wanted to write seriously for…a decade, but I was too scared or shy or judgmental of my own stuff to ever do it for more than a week without having a full on meltdown.
I was gearing up for another collapse in late January 2022 when I asked my friend Paul Millerd for help on Twitter:
And the rest, as we say in social studies class, is history.
Paul is a DIY your life path sorta guy (read his dope substack Boundless here) who left consulting and sorta roams around the internet like a self-employed buddha, helping people who feel ready to leave the corporate / 925 world behind. I definitely had doubts about him at first - like who the fuck is this guy he and what does HE get out of this, but after running several double blind experiments (meaning neither he nor I were aware of the experiment), I can safely say he is simply a good man.
He kept sending me kind messages that at least did not feel like they were bullshit:
And for a frail, young writer who was confident that everyone hated his work, that genuinely meant the world. Paul had no reason to reach out and say that unless he meant it. Or maybe this just means he pulled off the perfect crime that sunuva! But it seemed genuine and so I believed him.
I wrote four pieces in February, three in March, five in April and May, six in June, and nine in July. After that, I didn’t really need to do the $ trick, but before that, it worked SO WELL for me. It may not be for everyone, but it somehow checked all my guilt, shame boxes. Plus I just can’t lie. That was key - I knew I wouldn’t be able to lie to him, and I really could not live with losing my money, period, especially if it went to a bad guy.
#3 figure out what your deal is
For this, and almost everything else in my life, I thank Substack Grow. Katie and Bailey and the rag tag crew over there (who btw are always at Office Hours every Thursday to hang and answer questions and again, are the best) led this badass 6 week thing last summer that helped me in many ways, one of which was figuring out what the hell my substack WAS.
What do you offer to your readers, they asked. For others it was easy - fintech (different ways fish can swim), crypto, the news, cooking, but what do I offer?
My heart? My soul? And a fart joke or two?
But I didn’t know how to put that in a way that people would understand, nor did I know who my actual audience was.
I was real stuck, tbh, so I commented in our Grow threads and asked what the hell I should do — here’s my question and Katie’s genius response:
Absurd, honest comedy delivered twice a weekish through the vulnerable personal essays of Alex Dobrenko: friend to all, father to one, and tv actor+writer to anyone hiring.
I love that because it both Shows and Tells you that I try to blend absurd goofs with vulnerable troofs. Dang wait that might actually be a better tagline brb.
#4 make friends!
Grow helped jumpstart this for me because we were doing breakout rooms with other writers in our category, so I was hanging every week with the humor kids including Anne Kadet who is a close pal now and also the writer of Cafe Anne, which is actually too good they might make it illegal soon.
Then, at an LA meetup, I got to know a lot of cool writers including Michael Estrin of the super funny Situation Normal and Geoffrey Golden who makes the choose your own adventure game newsletter Adventure Snack, both of whom intimidated me in that sort of “these guys are great and probably better than you but you should go talk to them.
But I didn’t know them, not really, and so I employed a very specific tactic which I have trademarked:
#5 The Hail Mary Email™
So it’s just like a normal email, except you have little hope that the other person will answer it. It’s a long shot. No expectations. A last minute prayer. And surprisingly often, it works!
Like with Anne, Michael, Geoffrey, and Liz Donnelly, to name a few.
But definitely not always hahaha. I emailed E. Jean Carroll recently and SHE HAS Not RESPONDED which I am NOT AT ALL ANXIOUS ABOUT.
#6 Accountability buddies
Creating accountability groups ROCKS. I’m in one with Anne and Michael and Jane Ratcliffe who writes Beyond where she interviews actually famous authors like Cheryl Strayed! which is so good.
We meet weekly to talk about our goals AND most importantly, for me, to have a space to ask all of my annoying questions — safe space where I can be honest and vulnerable and know that I wont be judged. Its pretty amazing, honestly, and to all of them I am grateful.
Also I have a writing group! It’s just with one other person though one of my best friends in the world Rae Katz who writes Inner Workings which she describes as “Living with chronic mysterious "women's diseases," while parenting, while still inconveniently harboring unreasonable capitalist ambitions that I hate/can't let go of. Boldly personal weekly column + monthly long-form essays.’’ Her newsletter is so fucking good and she’s one of the best funniest deepest soul humans I know. SUBSCRIBE!
We did the Artist’s Way a couple years back together and then were going to do it again but realized that it would be a lot more fruitful to skip all the feelings and just start writing. So we now share something almost every week, get feedback, and talk through it on a call. Rinse. Repeat.
I do not know where I’d be without these groups. I mean, I do. I’d be at the same house I live at now but I’d be sad.
#7 Read other people’s stuff!
Find people whose work you love and become a FAN. Comment on their posts, email them to tell them why you love their work, etc.
Also, you can learn SO MUCH from other people’s Substacks, especially The Big Ones with tons of subscribers. Before I started writing seriously, I was already a die hard fan of Culture Study, Today in Tabs, and Garbage Day, all of whom have a Discord server for paid subscribers where I’d just sorta hang out and chat with very cool people, some of whom are readers of BAT today because I promoted one of my essays in the ‘promo your stuff’ channels.
I also joined the Soaring Twenties Social Club which is basically like a cool kids club for writers to hang and share their work (after joining and meeting Craig Burgess, I realized this was not where the cool kids lived). There’s a ton of talented people in there doing incredible work, and Thomas runs the place like a man who believes in principles, which is weirdly rare these days.
OH - one of my biggest early jumps in subscribers was because I had a dumb idea to do a series called Messy Ass Spaces where we feature people’s messy ass workspaces (counter programming to the super sleek nice HD photos of people’s perfectly manicured desks). I posted mine and shared it in the Today in Tabs server where Rusty, the king of Tab town, shared it on his newsletter which has a lot of readers!
That was the second time Rusty featured my essay, actually. The first was the Piña colada post - which is probably the post I least expected to ever gain any traction whatsoever. I just wrote it for me - that song is insane, the lyrics are a travesty and no one knows it. I had so much fucking fun writing that piece, and I guess it showed. Rusty is so great everyone go subscribe to Today in Tabs plz.
This brings me to my maybe final few points, which I’ll try to do in a drum roll pees:
A SPEED ROUND:
#8 Turn off notifications — The ‘new subscriber’ emails used to rule my days, but there were never enough of them! I always felt like a failure and so I just turned em off. Did that stop me from staring at the numbers? NO. I tried everything to stop, but nothing really worked until one day I just sorta stopped.
#8A the day’s numbers always suck, no matter how good they are. I managed to stop staring at the numbers until Substack featured me (which was so amazing and accounts for like 50% of my growth). After that, I got hooked again like I’d bought Zoom before Covid and just kept checking the ‘ticker’ tape as it shot to the moon. (fun fact: I actually bought a few Zoom stocks before the pandemic and sold them right before Covid started because I am a SMART BUSINESS MAN). Right now they don’t have a grip on me but who knows, they might by the time I publish.
#9 Get your stuff in front of people - There are many newsletter recommendation services - I’ve had a lot of success with The Sample, both free and paid placements. And the dude who made it — Jacob O’Bryant, also just launched a similar yet newer version called Yakread (both of those links are referral links so if you sign up I win a boat). Lots more to say about this but i’m running out of time and energy so I will leave it at this for now and maybe follow up soon with more idk. Also if you can pay for ads, there’s lots of places to run ads including a marketplace for them called Swapstack. The best luck though is from reaching out directly to people who say in their newsletters that they are selling ads—those people usually have audiences and there’s no easier way to pitch your newsletter than to someone who is already reading one.
#10 Experiment - I tried all sortsa shit including having my twin brother Brad C. Onversion come and do some guest posts. It led to chaos and I think he died, but it also led me to try Help Wanted as an advice column which I really love doing and will do more of this year.
#11 Make the comments feel like a party — Not sure how this happened, but it did and I love it. The more people comment and get involved, the more I love writing stuff and the less I dislike myself. Speaking of…
Whenever I read posts like these - and trust me I’ve read a few - there is an implicit pedestal upon which I place the Successful Writer, who is of course different from me, Mr. Sucks A Lotmcgee. Sure, i’ll read the tips but i’ll never be who that writer is because, as outlined in Appendix A: I suck butt.
But now I am on the other side (i broke on thru), and I must report with great trepidation - I still suck! Or more specifically - I haven’t changed! I’m still the same guy and…there is no pedestal.
In other words - I often find myself embodying one of two beliefs:
I am the worst
I am the undeniable best (which is just a defense to protect from #1).
In either scenario, I can differentiate myself from everyone else - I’m special (either in how much I suck or how good I am, doesn’t matter).
But reader beware, because In this case, neither is true! (RING THE OTHER BELL). I’m not the worst nor the best, I simply am. Just like everyone else on Substack, tryna figure it out and get their ideas into the world.
There is power in realizing that, if only for a moment .
Plus - and frankly, furthermore, forevermore -- success is in the eye of the beeholder (don’t let go of that bee, it’ll sting u). This success is one because I decide it is, a fact I find myself fighting tooth and claw, resisting, negating, etc-ing (this is correct Latin i checked).
So, to end: I DO, despite myself, view this as a success. I am proud of myself for getting this far with something that I really love doing, and I’m excited to keep going.
this is no humble brag, either. I am simply walking you through my brain like they do on MTV Cribs (walking up to the amygdala this is where the magic happens!).
My eyes keep falling asleep as I try n finish this LIKE I AM A GRANDPA !!! Ok time to be done. Thanks and let’s make the next quarter one for the record books (books about old musical LPs_.
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Questions? Thoughts? Advice?
Despite the glibness of this essay, I do genuinely hope some of this stuff helps people. To that end, if you have any questions or anything or even better some advice for me, please let me know in the comments!!
i keep reading this as ‘despise myself’
I keep recommending this post to people, it's brilliant. "Word Barf" should be it's own separate section/stack.
Thanks for this Alex! Love how honest you are with your thoughts and feelings, they are very relatable!
I'm at this point of my own newsletter thinking of how to find my topic and who I'm writing to. It's been a bunch of personal essays now and I want to find an angle. Will try to connect with my writers in the community, and keep supporting others as well! What a reminder that we're all just a really supportive and friendly group.