Newsletter Economics: The Good, The Bad, and The Ugly

May 7, 2022—a date which will live in infamy.

On that fateful Saturday morning three years ago I launched the first iteration of this newsletter, which was then titled Field Research and hosted on CuckStack.

Since then, a lot has happened.

Leverage went from half-baked side hustle to splashy Big Five debut novel. The U.S.-led, post-War geopolitical order collapsed. And my wife's limitless contempt graduated from festering to smoldering.

And yet, rather than die ignominiously alongside representative democracy, this ridiculous little newsletter has continued to evolve. From weekly and free (May 2022), to weekly with recurring payments (Jan. 2023), to sorta weekly with one-time payments (Sept. 2023), to bi-monthly with recurring payments (Sept. 2024), to bi-monthly and free (Nov. 2024), to all the way back to weekly and free (Feb. 2025), to whenever I’m in the goddamned mood and free (May 2025).

Despite my incessant waffling—and the overwhelming evidence I have no idea what I'm doing—I’ve managed to grow my readership from 162 depressed corporate stooges to 1,344 depressed corporate stooges, starving artists, and internet randos. And despite sporting the worst financial ROI of any business venture I've ever attempted, I've refused to throw in the towel.

Why?

Well, like most things in life, the reasons are myriad and complex.

The mad scientist and corporate mercenary in my brain, who are coldly rational and deeply unsentimental, have repeatedly made the case for whacking this newsletter and tossing its profitless corpse in a pool of wet concrete.

But the flowery artist and loudmouthed extrovert in my soul, who believe this newsletter brings real joy to real people and makes me a stronger, more well-rounded writer, recognize its small but mighty contribution to our species.

Throughout the remainder of this essay, which features my patented panache and radical transparency, I’ve reflected upon the past three years of this maddening pursuit, and I’ve articulated the good, the bad, and the ugly things this newsletter's contributed to my nascent writing career.

The Bad

Note: I'm gonna begin with the bad, move to the ugly, then conclude with the good. This will ensure we traverse the tried and true "Man in a Hole" story arc.

Opportunity Cost

Let's start with the most obvious downside of running an email newsletter: opportunity cost.

These pieces take a ton of time to create, and every second I spend laboring over the grammar in an email most of you are gonna skim for the GIFs—or delete outright—is a second I could be doing something more productive. Working on my next novel. Pitching online pubs. Raging on social media. Building out a podcast. Masturbating.

I mean, the alternatives are endless, and given the amorphous nature of the creative enterprise it's always rational to wonder whether I could be spending my time more efficiently. This specific challenge is exacerbated by my own perfectionist psychosis, which fears the stinging sense of rejection brought about by even the slightest of mistakes. Parental abandonment dies hard, ya know.

Beyond my Freudian hang-ups, I also try to manage my "personal brand" with intention and I want people to associate everything I do with quality. When I invest my precious time and attention in a story, you can bet your bottom dollar it's gonna be worth your precious time and attention.

In a similar vein, the half-assed and reactionary nature of social media is exactly why I hate it so much. I can't begin to tell you how many allegedly serious people I wished I'd never “followed,” and who I view in a less than flattering light due to their antics online.

While I'm certainly quick with a one-liner, I hope to identify universal truths or capture complex, nuanced ideas with my creative content, i.e., the kind of material which doesn't rate on social media but plays well as long-form content.

In sum, writing this newsletter absolutely takes too much of my time, which is very bad, but I prefer this medium to the utterly useless alternatives, which is not so bad.

Metrics Madness

Because I'm afflicted with America's growth or death sickness, it's easy for me to spin myself in circles with dashboard data, email metrics, and growth hacks. Again, I suffer more than most in this regard because I'm a scientist by nature and pretty good at math.

Growing and monetizing an email newsletter seems like a soluble problem, which should be subject to tangible strategies and reproducible solutions, and my eager little monkey brain simply can't resist searching for the "correct" answers to these ostensible business problems.

This is why I'm constantly fiddling with publishing frequencies and monetization models: I'm always probing for more data so I can make sound, logical, NPV-positive decisions. Because, at the end of the day, if my newsletter's not turning a profit, I'm just another intrinsically worthless cog in our ruthlessly capitalistic machine.

The problems with this deranged mindset are, of course, obvious: There are way too many variables to consider, and the data available are, at best, inconclusive, and, at worst, hot garbage.

On this front, moving from CuckStack to Ghost has been a blessing. My dashboard data is cleaner and my financial incentives have been completely inverted.

Since my wife pays service fees based on how many "members" I host, I no longer feel that pang of disappointment when somebody unsubscribes. In fact, nowadays it's more like: Good fucking riddance you freeloading fuck.

Kidding aside—I'm not kidding—the situation is healthier for everyone. When a reader abandons ship, they remove unwanted content from their inbox, and I triangulate toward my "true fans" while concomitantly reducing my wife’s downstream expenses.

All this said, because I have an elephant memory, and savor my grudges, I will never forget nor forgive those freeloading fucks for betraying me.

The Ugly

Content Warning: This section lives up to its namesake. What you're about to read is ugly, and it's ugly because it represents my ugliest, innermost thoughts. I'm nothing if not honest, probably to a fault. Alright, bite down on something.

My Big, Dumb, Fragile Feelings

Consider these facts and anecdotes:

• People I've known for twenty-plus years tell me my work is hilarious and then open fewer than 10% of my posts
• People I've known for twenty-plus years tell me my work is hilarious and open 100% of my posts but have never financially supported my efforts—despite my persistent and pathetic pleading in the past
• Hundreds of people who work in Corporate America, or on Wall Street, and live in my ridiculous neighborhood, or in other big U.S. cities, and occupy the literal 1% class, and possess ample resources, tell me my work is hilarious and open 100% of my posts but have never financially supported my efforts—despite my persistent and pathetic pleading in the past
• Some of my very own in-laws, who'd been subscribed since day one, didn't realize they could pre-order Leverage until I texted them and asked if they'd done so [Note: I expunged their memberships.]
• People I know personally, and like very much, who have been subscribed to my newsletter for years, text or email me questions whose answers were provided within the contents of my most recent post, which my dashboard data confirms they received, and opened, and obviously didn't read

Bruh, this shit transcends demotivating.

This shit is demoralizing.

If I'd lived during the Achaemenid-Persian Empire, and I'd been subjugated and conscripted into Darius III's army, and I was told I had to fight for the King, and if I agreed I'd earn the luxurious rewards described above, but if I refused I'd get fed to a pride of starving lions, I would 100% choose mutilation and mauling via the pride of starving lions.

But wait—it gets worse!

Because I learned long ago depression is "anger turned inward," and I also learned how to repurpose and redirect my anger outward—at the people and institutions where it belongs—I often end up feeling extreme frustration with and bitter resentment toward you people.

Even though you voluntarily signed up for this newsletter—or I strong-armed you into subscribing during an awkward social interaction #alwaysbeclosing—and you never made an explicit promise of financial support.

And even when, in a saner, less neoliberalist version of reality, I'd simply appreciate the fact anyone reads this nonsense at all, and I'd recognize what an absolute privilege it is to do this kind of work, particularly for such a large and sophisticated audience.

Especially when I know zero people of sound mind want to willingly exchange U.S. dollars for a demented email blog written by a middle-aged asshole who's not even fucking famous!

Trust me, I realize I sound like an entitled, petulant dick. I’m just being brutally honest here. But there's good news, too. Even my stupidest, most self-indulgent feelings don't get to determine how I respond to these challenges or how I comport myself as a creator.

Which is why, despite countless pitiable and pathetic moments, for three motherfucking years I've given this goddamned newsletter my best possible effort. I'm very proud of that fact.

Financial Sinkhole

Finally, as if the whining above wasn't gratuitous enough, I earned orders of magnitude more money from one traditional book advance than I made during two combined years of operating paid iterations of this newsletter. Note: Without my wife’s emotional and financial largesse, both ventures would’ve qualified me for Medicaid.

In other words, even though traditional publishing has long been dead, when compared to monetizing this sad little email blog, querying bloodsucking literary agents and securing a Big Five book deal from a private equity-owned publishing house was a phenomenal investment decision.

Mercifully, we've now reached the bottom of the hole. Let's find a way to dig ourselves out and go home happy.

The Good

I wanted to tackle the bad stuff first because, believe it or not, operating this newsletter has been a net positive experience. Especially when I remember to zoom out and look at the totality of the evidence.

Sharpened Skills

Without a doubt, the biggest benefit of creating and producing this newsletter has been my continued development as a craft writer.

Sure I didn't find much any success monetizing previous variations of this publication, and in terms of building an online following perhaps I would've been better off focusing on a pure social media channel.

But the sheer amount of reps I put in because I committed to writing almost every week has absolutely been worth the effort, and I’m certain the experience will continue to pay dividends for the remainder of my literary career.

Many people assume creative pursuits are somehow immune to improvement through practice. Or believe there's some magic elixir which makes certain people more gifted at creative work than others.

Innate talent is a real thing. But anybody who's ever played organized sports or been on a team in Corporate America knows it's always better to suit up with a comrade who has low talent and elite work ethic than with a prima donna who has elite talent and low work ethic.

Humbly speaking, I've always had writing talent. I've had a way with words since I was a kid and a knack for storytelling since I was in high school. But the secret to my writing success is I'm an insatiable sociopath who's fueled by spite.

When I first declared myself a novelist in November 2018, my "raw" talent was only good enough to produce a bloated piece of dogshit which couldn't even elicit "nice" rejections from literary agents.

It was only after I put the work into that novel and started Leverage from scratch and studied craft techniques and attended writing conferences and began writing these weekly missives that I took my game to the professional level.

I like to use weightlifting as an analogy.

Even the purest athletes don't walk up to the squat rack and load the bar with plates. They start light and focus on technique. Then they systematically add plates as they get stronger and stronger. And over time, they eventually start jacking crazy amounts of weight like an absolute beast.

Creative writing is no different.

I've got almost 200 pieces in my portfolio, from poetry to flash fiction, from gonzo journalism to personal essays, from conceptual humor to cultural criticism, all of which have made me a better and stronger writer, and have leveraged my latent talent. (See what I did there?)

In that regard, writing this newsletter has been a slam dunk, grand slam, hat trick, sixer, [insert your favorite sports slang].

Rewarding Relationships

Networking with industry professionals and establishing connections with other authors—from forming loose acquaintances to creating close friends—has been an absolute boon to my authorial endeavors, and these relationships were all made possible because of my newsletter.

By writing every single week and taking big swings with my creative output, I got on the radar of some incredibly talented people who've gone on to form the foundation of my literary fam. For example, I met up-and-coming superstars Dennard Dayle and Andrew Boryga via the Substack network, and they each beta read and wrote blurbs for Leverage which helped me snag my literary agent and bank my book deal.

From there, I parlayed those relationships—and my own schmoozing superpowers—into additional networking opportunities with literary hotshots Mateo Askaripour, Lincoln Michel, and Leigh Stein, all of whom contributed fantastic blurbs for my novel.

Aside from those Leverage-related wins, the sheer quality of the people who read this newsletter—corporate executives, librarians, university professors, publishing professionals, K-8 teachers, comedians, financial analysts, award-winning novelists—is, frankly, astonishing.

You brilliant humans keep me humble and hungry.

Creative Freedom

The final benefit of sustaining this newsletter is the creative freedom it affords.

Unlike many people in the newsletter game, I'm not an anti-institutionalist blowhard. I bulldozed my way into the traditional publishing ecosystem by working like a madman, and I did this precisely because of the imprimatur of credibility and quality that's conferred by such an association (even if it’s often undeserved).

That said, contending with gatekeepers at every turn can be creatively stifling and highly demotivating. My incompatibility with McSweeney's is well-documented, and I honestly can't think of a single piece I've written which would've fit the bill at Shouts & Murmurs.

Every story I've loved and submitted to those outlets has been rejected, and those same stories have all been well-received by you people. Every time I think about what types of pieces would match the "taste and aesthetic" of those august publications, I lose interest. That's not to say they're low-quality outlets or I'll never take another shot on goal, but rather an honest acknowledgement I don't do what they do.

I do what I do.

By maintaining my own personal playground, I get to flex my creative muscles, and I get to transfer that positive energy into my long-form, commercially viable projects.

What's Next?

But, like, what does it all mean, Man?

Three years and hundreds of thousands of words later, a clear-eyed takeaway mocks and eludes me. As I detailed throughout this essay, the qualitative benefits of running my newsletter are immense, but the quantitative elements leave much to be desired.

If I had unlimited money and unlimited bandwidth, I’d keep on keeping on. But I don’t. And like any artistic enterprise, the fundamental—and perhaps irreconcilable—tension between creative fulfillment and commercial self-immolation remains a constant concern.

I can produce “content" for days. But content doesn’t buy groceries or fund 529s or assuage my wife’s perpetual disenchantment.

On the other hand, the paid newsletter business model is mostly bullshit, definitely unsustainable, and certainly experiencing a CuckStack-inspired bubble period. The bust will come and the aftermath will be quite painful for the fly-by-night creators who are attempting to build their careers using the “thousand true fans” scam paradigm.

When I step back and consider why I launched this newsletter in the first place, I remember my overarching objective was to establish an “author platform.” In theory, said platform would showcase my abilities and connect me with future readers of Leverage.

So...mission accomplished?

Yes!

But with one major caveat.

Three years ago, this platform building exercise and the so-called content strategy I’d come up with complemented my novel writing practice. Today, however, running this newsletter often feels like an impediment to my primary goals.

This is especially acute since I’m now grappling with an extremely high-class conundrum: How do I write my next novel while also promoting Leverage while also writing my newsletter while also dicking around on social media while also being a domesticated house dad trapped in a decaying condo?

Given those wide-ranging constraints, I’ve concluded this diatribe by first discussing the alternative pathways I evaluated, and then explaining how I plan to construct the next pillar of my media empire.

Tap Out

On one extreme, I considered choosing the rational course of action and terminating this newsletter with extreme prejudice. My corporate mercenary brain was all-in on this plan, but my flowery artist brain wondered: How will we infect the others with our diseased thoughts?

Status Quo

On the opposite extreme, I considered staying the course. I tried telling myself I just needed to accept this is a fun but wildly unprofitable enterprise with intangible benefits galore. Alas, even my flowery artist brain was skeptical of this bandwidth-sucking approach, and my corporate mercenary brain was like:

Go—But Not Get—Paid

Another possibility would be to reintroduce paid subscription tiers and attempt to compensate myself for my self-inflicted troubles. Beyond completely contradicting the shade I threw on the paid newsletter model above, neither my flowery artist brain nor my corporate mercenary brain wanted to go back down this path.

Let’s consider the reasons:

• I’m not super famous and it’s exceedingly unlikely I will be anytime soon
• It’s legit degrading and deflating to constantly beg for money and constantly get rejected
• I don’t want to feel trapped in some kind of dysfunctional internet marriage with the eight generous souls who do decide to pony up
• I’m incapable of conjuring up and committing to a coherent content strategy

Be Normal

Thinking way outside the box, I also considered converting this debauched email blog into a proper author newsletter. You know the type: Here’s what I read this month, here’s what I watched, here’s a link to a podcast I blathered on, and here’s a picture of my dog. Like a high-fiber diet, these newsletters are boring but sensible. I, of course, am not those things.

Back to the Future

Finally, I debated an intriguing but self-defeating approach where I'd keep creating similar content, but stop sending my newsletter via email. In essence, my modern-day email blog would revert to an old school web blog.

The benefits would be considerable:

• I'd cap my wife's annual expenses at $300 per year
• I'd no longer need to obsess over email metrics or worry about spam filtering by newfangled “inbox management” programs
• I could stop worshipping at the altar of growth
• I could write whatever TF I want, whenever TF I want (Note: Contrary to popular opinion, I do exercise some editorial judgement)

Of course, the downsides would be even bigger: Seven people would visit my online blog each month—at best—and I’d need to build a sizable social media following for (ineffective) distribution and (ineffective) discovery.

This latter element was the dealbreaker.

I have fuck-all social media presence as is and, to be honest, little interest in changing that fact. In a more hopeful version of the future, Leverage will sell super well and deliver definitive proof social media is not only culturally worthless, but—at least for this author—commercially useless, too.

Final Answer

After analyzing the options above, and synthesizing three years of lessons learned, here’s the hybrid solution I cooked up.

• I’ll continue to create content I enjoy, because when I love a new piece you people tend to as well. The majority of posts will still be sent via email—for free—but I’ll also mix in some direct blogging to my website.
• I’ll aim to send out at least one piece per month, but no more than one piece per week. Sometimes I might disappear for weeks (or months) on end, and sometimes I’ll have a smorgasbord of ideas to share. The crucial element here will be flexibility, which is nigh impossible with a traditional paid newsletter since subscribers rightfully demand value for their dollars.
• I will paywall the majority of my existing portfolio on Sunday, June 1. This needle-threading move will establish a vehicle for monetizing my prior work without creating an obligation to constantly deliver new material. In essence, you people can support the show by paying for past performance, which we all know—but frequently forget—is not a predictor of future performance. Pro tip: Stories listed as “Members only” are currently free to read after signing in. Effective June 1, access to those posts will change to “Paying members only,” so be sure to log in and read any- and everything that interests you beforehand.
• The one and only pricing tier is active and the flat fee is $19.99 per year. There are no bells, whistles, discounts, gimmicks, or strings attached. It’s a take it or leave it proposition, and experience suggests 99.9% of you discerning consumers will tell me to get bent.

Parting Thoughts

All told, writing an email newsletter is damn hard and financially foolhardy work, but I’m glad I’ve stuck with it.

A huge, massive, mega thank you for all the support and engagement over these past three years.

As always, stay frosty out there.

—Amran