How Alex Dobrenko Got Two Dream Jobs Because of His Newsletter
Bonus Material for Launch & Grow a Newsletter to Boost Your Writing Career
Hi writers!
This is the final post of our newsletter month. I’m a little verklempt. Putting together this month of educational programming was a tremendous undertaking, but it also reinforced one of my favorite things about the power of newsletters:
Writing forces you to think through ideas and concepts more thoroughly to convey the information effectively. So, despite the fact that I’ve been writing my newsletter for two and a half years and I’ve taught three newsletter classes, working on these posts has elevated my thinking and performance on the topic. I wound up updating my welcome emails and making a ton of other tweaks to my own operation.
You can still upgrade if you want access to the recent lessons on growing your newsletter and going paid (and other ways to monetize)!
Our last Q&A is with a writer who I’ve seen have such great success on Substack in a relatively short amount of time. His name is
, and he’s the creator of . Alex is not only hilarious, but he seems to be genuinely having fun with it (when he’s not being tortured by life; hence, “both are true”). There are so many great takeaways from this one, so without further ado…
What’s the basic premise and tagline of your newsletter?
AD: Both Are True is an absurd, honest comedy delivered twice a weekish through the vulnerable personal essays of Alex Dobrenko: TV actor and writer to some, father to
onetwo, and friend to all.
When and why did you start your newsletter?
AD: During COVID, I decided to finally try a lifelong passion: standup comedy. Except I had a newborn at home, which between us, girls made doing open mics most nights of the week kind of… suck. So I decided to try writing instead with a basic premise of, what if I did standup on the page? And so Both Are True was born.
Who’s your main audience?
AD: I truly do not know, so I decided to ask my audience who they were via Substack chat. After reading everyone’s responses, I still have no idea who they are, but I can tell you one thing: they’re a buncha weird, funny lil idiots like me.
How is your newsletter differentiated from the other newsletters in your niche?
AD: My writing is super personal — the stories are about my life as an immigrant from Ukraine, a Jew with a lootttaaaa mental health stuff, a dad, an only child, and, through it all, just a lil guy, so no one else can really replicate it. But within the Humor category, my work mixes the absurd with the vulnerable in a way that’s unique, I think, from anything else that’s on Substack. That didn’t happen by design though, but more by just writing honestly and seeing what came out.
What’s your editorial strategy? Including: What kind of content are you focused on offering? What’s your publishing cadence? How far in advance do you plan your content calendar?
AD: I publish twice a week on Tuesdays and Thursdays, but there’s definitely flexibility built in. I try to be consistent, but if I’m stuck on a piece, then I give it the extra time it needs. That’s new though, the allowing, that’s new for me. For a long time, I would lose my shit if I was gonna miss a deadline. Ultimately I realized that it truly doesn’t matter. I wrote about this in my 6666 tips on how I reached 6666 subscribers on Substack:
Your readers will go days - WEEKS - without thinking about your newsletter even once. Your baseline in their minds is between neutral and a mild to high-key 'yay.
When they see your newsletter, it might make them happy, but not seeing your newsletter won't make them sad.
No one is thinking about you as much as you're thinking about you, and the same goes for your work. I spend zero time thinking about MY FAVORITE ARTISTS in the world unless something new of theirs comes out. And even then, I'll enjoy the hell out of it and continue on my day's agenda of worrying about shit like my own newsletter.
This is liberating! This is good! This is the best. The writing exists to help people, entertain them, or whatever. And it can do all those things. But if that writing isn't there, or is weird or doesn't achieve those goals, no one will care! Which brings me to my next tip.
My focus is pretty squarely in the CPEU (comedic personal essay universe) with shorter topical rants sprinkled in. I plan about a month in advance, which I can pull off because I’ve got an amazing producer named
who works with me. She’s been my Both Are True sidekick since the early days — we started together when I had 2K subscribers — and has been integral to my growth. You can learn more about her work here.
How many subscribers do you have?
AD: 9,908, which is so close to 10K I cannot believe it. Honestly, I bet by the time this is published, I will have probably crossed over into the 10K club, which is honestly insane.
[Editor’s note: Alex has indeed crossed over into the 10K club. Big congrats!]
Do you offer paid memberships? If so, explain when and why you turned that on, what your subscription offering includes, the cost, how many subscribers are part of your paid community, and any takeaways from going paid.
AD: Yes. I turned on paid subscriptions in July 2022. We’ve got about 400 paid subscribers, which includes 100 comps (that’s one takeaway — give out lots of comps!). To be honest, I’m not really sure what works and what doesn’t, but I know what doesn’t work: obsessing over figuring out what is gonna work. All of the “gimmicky” things I’ve tried to do to quickly get subscribers haven't worked.
The only thing that works is the hardest thing, which is to write good stuff. It’s hard because I can’t ever predict which of my pieces will be hits and which won’t. So I try to cheat and lure readers with additional perks (more essays, monthly videos, etc). They move the needle a little, so maybe they are worth trying out, but then there’s always some drop-off, so it’s hard to say whether that growth really sticks. Actually, maybe another thing that worked decently well was promoting a season/series of essays and spending a good chunk of time teasing it before it launched, including offering a discount on subscriptions. Then we launched the season with a paywalled essay.
Pricing has been a little all over the place. I started at $5/month and $50/year then increased to $7/month and $65/year, which did pretty well for me, but I also felt like I was keeping a lot of people from subscribing, even though I gave out a bunch of comps. So recently, as I’ve started a new job and money’s been less tight, I’ve cut the price back to $5/month and $35/year to focus on volume of subscribers over payout.
I’ve also written a few pieces about growth, which you can check out here:
How I grew this newsletter from 56 to 2,177 subscribers in less than a year
a bunch of tips for using Notes + my origin story using the platform++
Alex Dobrenko, comedian and writer, on how to have fun in Notes – my interview with Co-Founder /CEO of Substack, Hamish McKenzie about Notes
Have you tried any other methods of monetization?
AD: Late last year, I began offering my services as a writing coach/editor/Substack support person. You can see my launch post for that here. It has gone surprisingly well, though I have stopped taking on new people because I was recently hired as the Head of Creative at Sublime, a job I was offered because the founder really loved Both Are True.
Tell us about your newsletter’s growth trajectory. What have been the most effective ways for you to promote your newsletter? Did you have any growth spurts, and what did you learn from those?
AD: I feel like a lot of this depends on the stage that you’re at! In the beginning, I was posting stuff in Discord a lot and sharing really anywhere it seemed okay to do so. Once things started going, recommendations have been clutch — like 50 percent of my entire subscribers come from recs. Growth spurts came in January 2023, from Substack highlighting me in
as a featured newsletter, and again in August 2023, when I did an interview with Substack co-founder about using Substack Notes. “PR” things like that make a huge difference, but I’ve also gotten huge influxes of new subscribers from just writing good pieces, like this essay about addiction from October.
What’s been your most popular content, and your guess as to why?
AD: Beautiful Disasters, the post I just linked to above, is my most popular essay, and it tracks with what usually does the best: vulnerable, relatable essays about my struggles with myself and/or my family, where the writing is really strong; there’s tension built, there’s funny moments, serious moments, and some kind of resolution. Another good example is this essay about how my Soviet parents act when I don’t answer their phone calls.
Also hating on AI and stupid new tech has worked out pretty well! I think people really love to hate stuff together.
How has your newsletter served your career as an author?
AD: It’s been huge! I’ve landed two really cool jobs from it, including my role now as Head of Creative at Sublime. I’m going to be heading up their newsletter, too, which you can check out here. Both of those full-time gigs came from people seeing Both Are True and saying that they wanted me to bring that energy to their company.
I’ve also been contacted by some book development people to adapt a young adult novel. It ended up not happening because the company closed their book division but still, it was pretty sweet!
I also spend a lot of time in the comments, and I get a ton of material from responding to people. It almost feels like doing crowd work. I see what they said and come up with a funny/good response. This is also why Help Wanted, my advice column, is so fun — people ask questions, and I answer ‘em! I’ll be relaunching Help Wanted as soon as my brand new baby girl, Emma June, says it’s okay.
What’s your #1 tip for writers who want to start a newsletter?
AD: Make friends with other newsletter writers. It’s a lonely gig — community is KEY. I have a writing partner —
— who I talk to all the time about our writing and Substacks, and I also have a writing group with three other Substack writers named , , and — we meet up over Zoom monthly. It’s essential to have people you can go to and say, “Hey, is this crazy?” and have them actually understand what you’re writing about.
What’s your #1 tip for writers trying to grow their existing newsletter?
AD: Send a survey! You can learn so much about what your audience is like simply by asking them. Plus you get great testimonials. I did two surveys — one for my free subscribers and a different one for my paid subscribers. A lot of what I did was based on this article which I recommend checking out too!
Also, craft a welcome/hello email that’s authentic to you. Here’s my welcome email and a bit of info on why I think it works. Seriously, I get probably three to ten responses a week to that thing, it’s amazing — it’s such a nice way to get to know the readers.
Shout out another writer-newsletter that you admire and enjoy consuming.
AD:
Inner Workings by Rachel Katz,
Anything else you’d like to add?
AD: Before Substack, I did a lot of comedy stuff on Twitter/X, and so did every other comedian, lol, which meant it was hard to get your stuff seen since it was such a saturated place. On the other hand, no one was really doing comedy on Substack, so I figured if I could pull it off, I’d have a better chance of getting noticed.
Thank you so much, Alex! Make sure you subscribe to his Substack,
.Bye for now to all my amazing WOD101 friends! I’ll be back again for a full month on how to build your writer platform. In the meantime, see you in the comments. :)
Your Newsletter Bestie,
Courtney Kocak
P.S. If you’re trying to get published, join me for my upcoming Write or Die workshop, Land Big Bylines by Writing for Columns. I would love to see you there!
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I love the Alex wrote, of his audience, "They’re a buncha weird, funny lil idiots like me." Not that I agree with his self-assessment, but I do think it's true that when it comes to newsletters, the readers tend to be a reflection of the writer.
This was great! Really glad Alex talked about Beautiful Disaster. It’s not just my favorite Alex essay, it’s my favorite personal essay period. It’s deep and smart and moving and vulnerable. And it’s damn funny, like I’m jealous of how funny it is because the dude literally found an original take on the old chicken and egg joke, which ought to be impossible. Go read this essay, people.