🔴 Lessons in newsletter growth from Brad C. Onversion

ft. Alex Dobrenko — comedian, writer, and creator of Both Are True

Author

Francis Zierer
November 15, 2024 • Estimated Reading Time: 15 minutes

Your guide to the newsletter world — new stories every Friday. Brought to you by beehiiv.

Today’s guest is Alex Dobrenko, creator of a newsletter called Both Are True, Head of Creative for knowledge-management app Sublime, and, generally, a writer-comedian with a natural talent for self-expression.

Alex is very much a “newsletter creator” — his work is unmistakably his, deeply personal, and born wholly of the medium. His is not a traditional industry-news newsletter; it’s more like a personal essay blog.

In this issue:

  • 🪞Notes on writing personal essays in a newsletter context

  • ✍️ Learning to professionalize a personal creative practice

  • 🫂 Building community to become a better creator and grow audience

  • 🎭️ A few techniques from the world of improv comedy to add to your writing

— Francis Zierer, Editor

Stand-up comedy newsletter

“Stand-up has always been my dream, sort of my Moby Dick, my great thing that I’ve never been able to do like I wanted.

During the pandemic, I quit my job. I was like, ‘I’m going to do stand-up for real.’

But we’d just had a little kid and doing open mics sucks really bad.”

Alex Dobrenko isn’t afraid to look like a complete idiot, something that over 15,000 people seem to love about him. He writes a newsletter called Both Are True and is one of the best personal-essay-columnist stylists currently working in the medium.

It reads like a diary acknowledging an audience.

In one post two years ago, he wrote, “I guess my north star has been to just be as honest as I can possibly be without upsetting my parents.” I asked him if that’s still the case.

“Honestly, the new frontier is upsetting my parents. That's genuinely the stuff I'm struggling to write now, what I know they won't like — it deals with stuff they don’t really know about, like addiction.”

Alex’s most popular post to date is an essay called Beautiful Disasters. It clocks in around 7,000 words, takes about half an hour to read, and has received over 100 comments. It’s written in a raw, stream-of-consciousness style. It’s about being addicted to marijuana. Going to Burning Man. Friends, family, love. Microdosing acid. Hitting rock bottom. Getting sober. One commenter called it “searingly great.”

You must always remember that both are true

The newsletter's name comes from those acid trips — realizing, in the throes of the trip, that two things can be true at once; it’s never just one or the other. As he writes in Beautiful Disasters:

“Once, during an early acid trip, I realized that nothing matters, which means everything does. Or, more specifically, anything can. Nothing mattering allows us to create our own meanings.“

Alex has been developing this voice — here harried and hilarious, there crystal and profound — over about 3 years of newsletter writing (and 30-some years of bopping around, but that’s beside the point). Before choosing newsletters as the outlet for his comedy instincts, he made videos for Twitter; before that, he made a webseries about a long-distance relationship called Distance.

That’s years of playing various comedy games; only in newsletter world did Alex find a project he could both sustain longterm and monetize.

(We’ll get into a few replicable comedy techniques you might apply to your own writing down in the “Steal This Tactic” section of today’s newsletter.)

Professionalizing a personal creative practice

Though he first posted to Substack in 2019, Alex didn’t start posting regularly until February 2022. He had around 49 subscribers and hoped to hit 200 by the end of the year. In a post sent 1 year later, he shared a subscriber count of 2,177, including 63 paid subscribers.

This piece, like any other Alex has written for his newsletter, is funny, self-flagellant, and open-hearted. It’s the first in a series he’s written about growing his audience and developing his newsletter concept. (Find more posts from this series linked at the bottom of this newsletter.)

He doesn't always write these growth retrospectives from his own perspective — sometimes, he plays a character named Brad C. Onversion, supposedly his twin brother.

Brad seems like a way for Alex to sublimate his anxieties about selling out, a squirminess about building a business around a creative outlet, a product of his desire to monetize without snuffing some spark. It’s hardly a rare anxiety — a look in the comments of any post from this series surfaces dozens of fellow travelers.

Core to Alex’s talent as a personal-essay newsletterist is this ability to struggle with his fears and problems in public. To process his struggles with addiction, he writes Beautiful Disasters. To process his conflicting desires around professionalizing as a creator, he writes this growth-recap series and becomes Brad. It’s cathartic for him and cathartic for his readers — this catharsis is a core appeal for the audience.

It’s also telling that of the 11 pieces of advice he shares in that 1-year-anniversary-of-regularly-posting post, 5 come down to simply interacting with other people in earnest:

  • “#4 make friends!”

  • “#5 The Hail Mary Email™”

  • “#6 Accountability buddies”

  • “#7 Read other people’s stuff!”

  • “#11 Make the comments feel like a party”

He’s a prosocial essayist.

It takes a team and a village

Alex has always seen success by reaching out to people. Early on, subscribed to multiple fellow writers’ newsletters, he would comment on their posts and participate in their Discords. He would meet people there. They would recommend each other’s posts, swap essay drafts, and share feedback.

There are three key collaborators — Erin Shetron, hired in January 2023, handles creative producer duties, from editing to strategizing. Rachel Katz is a writing partner and sounding board; they exchange drafts and kvetch. Prolific BAT commenter Madeline provides additional editing support; they share a Slack channel where early drafts and ideas bounce around and germinate into drafts.

Look: nobody is building an audience or making high-quality content alone. The more the merrier! I interviewed Caitlin Dewey a few weeks ago, and she mentioned seeing a bump in paid subscriptions when Rusty Foster put his Today in Tabs newsletter on hiatus; he recommended his readers look to her in his absence. Not coincidentally, it was in Rusty’s Discord that Alex began several collaborative, fruitful relationships.

Another example is PJ Milani, who I interviewed this past spring. He first built an audience by participating in Dickie Bush and Nicolas Cole’s Ship 30 for 30 program, which is cohort-based. The group would post to Twitter each day and reply to each other’s posts. I saw the latest cohort doing this just the other day. Creating on the internet in community with other people always works.

Personal essays alone don’t pay the bills

Alex makes around $15,000 a year from paid Both Are True subscriptions. Which is, as he says, “for that 27-subscriber guy, crazy. But how do you support a family on that?”

In a classic Both Are True situation, the newsletter itself doesn't pay all the bills, but it has opened doors that do allow him to make a full living.

At one point, writing the newsletter but still without a full-time job, he began reaching out to other writers, offering to help them define their brand, edit their writing, and market their newsletters. He found most were interested in the latter. After helping a few people pro bono, he had testimonials and began picking up paid clients.

He then, about 1 year ago, got an offer from Sari Azout, the founder of Sublime, a knowledge management app, to work on their newsletter and handle a number of other responsibilities as Head of Creative. This is his full-time job; the newsletter and consulting work provide supplementary income.

I asked Alex if he had any idea what he might be doing 2–3 years from now. He hopes to still be working at Sublime and publishing Both Are True — and to have published a book of essays.

“I once wrote in a post, like, ‘If any agents out there want to help me sell my book, Crime and Punishment? Please reach out.’ And this agent from WME reached out.”

He and the agent went back and forth, and he asked about the next steps. She asked if he had anything he was trying to write; he “manically” wrote out a pitch he’d had in mind “forever” and sent it over. She told him what to do next, and he hasn’t done any of it, but “basically, I have a book deal,” he says.

If you take only one lesson from Alex’s work, let it be this: take your work extremely seriously, never let it get too serious, and talk to people about it. Other people are what it’s all about.

Connect with Alex on Twitter.
Read and subscribe to Both Are True.

🎙️ I had a great time chatting with Alex. He’s funny! He’s a great conversationalist! I really think you’ll enjoy this episode; it’s a great entry point into the podcast if you’ve yet to listen.

  • 💵 There’s a difference between monetizing your work and “selling out”

  • 🎤 We go deeper on applying stand-up comedy mindset to newsletters

  • 📈 Much more chat on how Alex grew his newsletter

  • ✍️ The only writing advice that matters

A very brief improv course

When I interviewed Rachel Karten, who writes Link in Bio about and for social media managers, she told me that the most common trait among people who are good at social media is a background in improv or comedy; I asked Alex to share a few techniques from that world.

You gotta riff

"You're not afraid to come up with bad ideas,” Alex says. Improv is about coming up with ideas at a rapid clip and supporting those ideas in real time — exploring them and pushing them to their logical and illogical conclusions. This is something you can practice. It does require other people. Ideas bounce better off of other people than they do off a wall.

Idiot work

There’s a genre of comedy called “idiot work.” For our purposes here, it’s about being able to accept failing in front of an audience … which makes the audience feel safe.

“What makes an improv show great is when a mistake happens and how the performers react to it.

Good improvisers, when something weird or dumb or bad happens that's clearly a mistake, they'll fold it into the show. And that will often be the best part of the show.

What they're actually saying to the audience, especially in live shows, is ‘I'm okay with failing,’ which is really saying to the audience, ‘You're safe.’”

Your audience is smart; treat them like it

I distinctly remember my 5th-grade teacher giving me feedback on a paper about “pretending my audience was stupid.” It’s possible I’d just left out a bunch of necessary context, but regardless, this is advice I’ve tried to lose. Alex says he was taught, in improv sessions, to “play to the top of [the audience’s] intelligence.”

“Don't dumb stuff down, don't slow down to explain anything, and don't worry if people don't get your references.

It's a respect thing. What it shows is, I respect you regardless of where you're at. Like, I'm just going to talk to you as though you're a cool friend”

Listen to the latest episode of Tasteland, the weekly podcast about media, tech, and business hosted by Spotlight editor Francis Zierer and Dirt Media CEO Daisy Alioto.

This week, we’re joined by Lauryn Menard, CEO and co-founder of Gob, a compostable, plastic-free, mycelium-based earplug company.

We discuss Tesla’s influence on green marketing, developing wild new biomaterials, and disrupting a market producing 40 billion disposable plastic earplugs per year.

More writing and growth advice posts from Alex:

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