Brought to you by beehiiv.
Today’s guest is a newsletterist covering the tech industry who makes his living by productizing his analysis in three different packages. He sells paid subscriptions, ads, and higher-ticket consulting.
It’s a sustainable but demanding model; he told us he works until his body “collapses into bed” each night.
In this episode:
— Natalia Pérez-González, Assistant Editor
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Building a premium tech newsletter
Six months after Evan Armstrong launched The Leverage, his publication analyzing the tech market, his audience began to shrink. This came as a shock; his subscriber list had only surged up to that point.
This surge was by design. Evan had spent four years at Every, a media and AI company, writing a business and strategy column called Napkin Math — his transition was amicable and tactical.
He announced he was leaving Every to go independent, Every linked its readers out to The Leverage, and he promoted it heavily on X (where he has just under 10k followers). Readers shared it with friends, recommendations fueled new subscriptions, and thus his list numbered roughly 30,000 people just six months after he’d made the leap.
Then subscriber growth slowed, flattened, and spent the back half of 2025 in reverse. Evan told himself it was simply the curious-passersby contingent moving on while the real audience stuck around — "the culling of the herd," as he put it.
Adapted from Evan’s most recently publicized metrics.
By December 2025, he was in a full-on panic. With a young kid, a wife finishing a PhD, and no shortage of bills on the way, his shrinking business was a “fix this or die” type of problem.
Evan committed himself completely to fixing it.
“[I’m] working until my body collapses into bed, unable to muster another ounce of effort. In practice these changes look small: a custom chart style here, one more research call to validate a thesis there. But over time, these incremental improvements have added into a company that is actually working.”
He works all day, then, after his daughter goes down for the night, he works a second shift several nights a week, typically from 7:30 pm to midnight. Now in his second year, he’s working more of these late shifts than ever.
Writing from a place of opinionated experience
"I approach each piece in the right emotional state of mind, which allows me to be more clear in my arguments, more interesting in my insights […] If your users are shrinking, it's because your product isn't good enough."
Until half a decade ago, Evan was always, in his own words, a "math guy." He worked in strategy and business operations — deploying capital and advising rapidly scaling tech companies on complex decisions — and had never written “anything longer than a 50-word email.”
In early 2020, he spent a couple of months working at Substack, and started publishing on it himself to better understand the product and customer. A piece on dating-app ethics, promoted on Facebook, surfaced a talent "so secret I didn't even know about it."
These early essays were bad, he admits, "but they felt really good at the time," good enough that he was soon shipping legal software by day and writing late into the night, soon realizing he'd rather spend his working hours writing than do anything else.
He started his own newsletter, People Speak — more sociological and theoretical than his work today — and soon sold it to Every in a modest acquihire deal.
Evan’s operator background forms the root of the authority his base follows him for today; he covers the tech industry as someone who lived and made decisions within it.
There’s a deep trust between Evan and his audience. His decision to go solo, after four years at Every, came in large part from a desire to completely own that relationship. Life as a solo operator is more difficult, but he is, by his own admission, “a sicko.”
Going solo made his opinions more credible, too; he has advertisers, but none of them can control what he writes — the selling and the analysis must stay separate. "I'll frequently publish things that I know my advertisers will dislike, but I don't care," he says. The freer he is to be prickly and selective, the more his analysis is worth to both reader and advertiser.
How Evan makes money
Evan strives for a specific audience of, as puts it, “people who can sign million-dollar checks” — venture investors, founders, and operators running large teams at tech companies. He doesn’t run surveys to measure the makeup of this audience, partly on principle: "I don't want the kind of readers that have time to fill out an audience survey.
The Leverage goes out two to three times per week, a high-frequency schedule requiring a steady supply of news to react to, and Evan is not a reporter; his raw material is everyone else's reporting.
"I'm a bottom feeder, taking the scraps from what all these other publications are creating and assembling it into something new."
The value Evan offers is in the assembly, curation, and analysis; he’s telling you which bits of the week's news actually matter, digesting it all into relevance for you. This analysis splits into three revenue streams, each one productizing his skill and sensibility in a different container.
Newsletter subscriptions (25-30% of revenue). The Leverage reaches roughly 35,000 free subscribers. They all receive the free “Weekend Leverage,” a concise take on the week’s news, and paying subscribers also receive the “Deep Dives:” longer, paywalled strategy essays featuring heavier analysis.
Subscriptions cost $15 per month or $145 per year.
Advertising (25-30% of revenue). Evan runs two ad products across his newsletter.
The first is a short, conventional placement in the free “Weekend Leverage.”
The second, "What's the Bet," sees a company pay Evan to publish a full strategic breakdown of their business (the technology, their strategic bet, the competition) while he keeps total editorial control. Originally, he built the format as part of a Notion sponsorship, ran it as a free issue, and it was so successful that it still converted a couple thousand dollars worth of paid subscribers.
Consulting (remainder; 40-50%). The most lucrative arm of the business. Startups and investment funds pay for Evan’s analysis on specific problems — "a brain for hire with deep market context," as he describes it. The newsletter acts as top of funnel for this service.
"I view my job as to make you do something. You should finish a piece of my analysis and know: I now need to do X and Y thing in my portfolio, in my career, in my company."
Evan measures success through the quality of cold emails, consulting offers, and co-investment opportunities that land in his inbox unprompted. A quiet inbox tells him his last piece missed the mark.
Another sign that Evan is hitting is mark? This spring, after half a year of shrinkage and stagnation, The Leverage’s audience started growing again.
Adapted from Evan’s most recently publicized metrics.
As he sharpens his analysis, he knows it needs more places to land.
In year two, Evan is investing heavily in YouTube video essays, defining success as videos that average anywhere from 100,000 to 1 million views, and hosting a series of live events. His inaugural The Leverage Live happened in Boston on May 26th and in NYC on June 3rd. In these rooms, the core of his audience, those million-dollar signatories, will gather.
Subscribe to The Leverage.
Connect with Evan on LinkedIn, X, and YouTube.
A few notes on building a premier product ✍
Evan is relentlessly committed to quality. He’s constantly studying, testing, and improving every part of his business, from paywall logic to pricing structure.
While listening to this interview, three of his methods stood out to me:
He borrowed his paywall strategy from cam girls.
This one was fascinating. Evan shared that one of his biggest weaknesses as a newsletterist is knowing what to paywall and when, so he went looking for the best paywallers on the planet and found a blog post by an OnlyFans creator on what to make free and what to make paid. "Who are the best people on paywalling on the planet? Cam girls. They can monetize anything," he tells us.
He turned her approach into a Claude skill — a saved set of instructions he can run any draft against — and refined it over months. The workflow: he writes the essay, drops the paywall where he thinks the argument naturally breaks, then runs the piece against the skill to pressure-test that placement. It usually suggests a new paragraph right before the cut, the tease that pulls a reader toward subscribing.
He never uses that copy as-is — "the writing is never good enough" — but it shows him what the paragraph should be doing, so he changes a word, cuts a sentence, adds one. The result was a real lift in his paywall conversion rates.
He uses Claude to grade his own track record.
Recently, Evan published an issue titled, “The Leverage Has Yet to Die,” wherein he used Claude to grade every prediction he's published on a 1-to-5 scale, from falsified to vindicated. This first pass covered 131 claims across 86 essays and 13 Weekend Leverage editions: 48 fives, 49 fours, three he'd call mostly wrong, and none flatly false.
His self-imposed rule is that if accuracy ever drops below 85%, he shuts the publication down. He's the first to admit this doesn't move revenue; readers don't think about it. It's a discipline he holds for himself, because the whole product rests on readers trusting his calls.
This practice dates to his time at Every, where he published a year edition titled, "Should You Fire This Newsletter?"
He prices for quality, and keeps raising prices.
The Leverage costs $15 a month, $145 a year, or $500 a year for a founding tier, steeper than most newsletters and more expensive than NYT or WSJ. Rather than compete on affordability, he bets on depth and rigor — trusting the work to earn the premium.
"The number one thing you can do to increase your income is increase your prices. Always, always, always.”
He set the original price mostly by instinct: Every charged $20 at the time, $10 felt too low, and $15 "sounded about right."
Today, he treats pricing as both a quality signal and a filter for the audience he wants — venture investors, founders, and operators running large teams at tech companies — and the $500 founding tier reinforced that belief. Subscribers largely ignored the perks and paid because they wanted to support the work — many wealthy enough that $500 a year "feels like $15." Above a certain price, he learned, you're not selling features; you're selling people a way to back you. He plans to keep raising prices, and if subscriber growth slows or churn rises, he'll learn where the ceiling is.
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