Hamish McKenzie is Right About Everything But Substack | Gimme Schalter №41

Ty Schalter
6 min readJun 20, 2022


I know Hamish McKenzie is a writer, because writers process their most difficult feelings by pouring them all out onto the page and hitting “publish,” with no regard for their self-interest.

The Substack co-founder’s latest newsletter issue, “Escape from Hell World,” is a gift I’m glad for: A glimpse into the mindset of a man who set out to make the world better for people like him, but is realizing now realizing he’s not actually ‘like’ all the people he thought were kindred spirits.

Last time I wrote about Substack, I said I was hesitant to do it again. Now, I’m doubly so — but this is a newsletter about life as a producer and consumer of digital media, and I pointedly did not build it on Substack.


Journalist, Observe Thyself

McKenzie focuses his emotions through the lens of Luke O’Neil, a writer he personally recruited to Substack. O’Neil’s “Welcome to Hell World” newsletter would go on to be not just brilliant, but a big financial success. McKenzie describes O’Neil with journalistic detachment, but clear admiration — and an emphasis on his own proximity:

I was there to convince him to start a newsletter. Luke’s friend Judd Legum, who had recently started Popular Information, thought Luke could do well on Substack because of his distinctive voice, cracked sense of humor, and livewire Twitter presence. Luke wore a fitted baseball cap and smoked cigarettes as if it were 1994. Tattoos crawled over his arms.

Over cocktails, I gave him my best pitch.

McKenzie might have been a businessman trying to land a client, but he wants you to know he was also out drinking with a Cool Guy at a bar in his hometown. McKenzie was talking shop, writer-to-writer, with an influential chronicler of late-capitalist America.

His pitch was right over the plate: A handful of mega-outlets were devouring the news-media ecosystem, book publishers had consolidated to squeeze more profits out of authors and staffers, and it was harder than ever for freelancers to make a living consistent and comfortable enough to focus on doing the work.

“It was a shitty time to be a writer,” McKenzie writes. It still is.

McKenzie went on to hold up O’Neil’s success as proof Substack could change everything.

But McKenzie didn’t really want to change everything.

As we sit here blogging, U.S. state and local governments are trying to separate queer parents and/or kids, gender-affirming health care, forbid trans kids from playing in sports, and even take LGBTQ+ books off the shelves of libraries and bookstores alike. It’s a movement of hate platformed online and enabled by media executives too chickenshit pass up the clicks.

McKenzie and the other public faces of Substack get hopping mad when you accuse them of recruiting and paying right-wing transphobes. They think it’s so unfair that they’re untruthfully accused of platforming and promoting writers Just Asking the Trans Question. Writers whose questions were answered by not just a global wave of anti-trans sentiment, but a digital-media hate machine daily getting individual trans people harrassed, fired, and assaulted.

Yet McKenzie’s post contains all the same giant obvious dots everyone else connected, albeit obfuscatingly scattered around the post. He also added a big one: An admission Substack saw the rise of MAGA not as a threat to the progressive platform they’d built, but an opportunity to stop being progressive.

“For a while, we worried that Substack’s left-wing lean would make the platform an unwelcoming place for people with different points of view,” he admitted.

“We could attract great writers, get them set up with thriving businesses, and sometimes we’d even make money on the deals,” he said about their Substack Pro concept.

“In the space of a few months,” he later added, as if it was some kind of accident, “[Bari] Weiss, [Andrew] Sullivan, and [Glenn] Greenwald subsequently moved to Substack and massively increased their income and influence.”

Throughout the criticism, McKenzie and PR chief Lulu Meservey have pretend Substack’s policies of secrecy around Pro are hand-tying laws of nature.

If the world can’t prove any particular writer was given a six-figure check from Substack, Inc., they think, we can’t criticize them for platforming (and profiting off of) a bunch of odious right-wingers directly responsible for fomenting this civil-rights rollback:

McKenzie whines that Substack’s critics aren’t listening to his explanations. But the ‘explanations’ didn’t fall on unfairly deaf ears, they simply don’t fit the facts.

Substack, for the sake of growth, set out to create the perception among creators and audiences that they were MAGA-friendly. However much money they spent in the effort, they succeeded. Surely, it was all to the delight of their venture-capitalist investors.

McKenzie was clearly affected when O’Neil first told him Substack was “fucking up” — and again when O’Neil left Substack. O’Neil was McKenzie’s archetypal Substacker, and the two of them mutually benefitted from their relationship.

But while McKenzie might still be a writer, he is not a Cool Guy. After building his company’s visibility and legitimacy on the backs of progressive writers, he lavished a bunch of VC money on regressive ones. He earned all the criticism he’s getting, such as from literary agent DongWon Song:

McKenzie is clear-eyed when assessing writers’ place in the world, and the many challenges they face:

Writers have been belittled and demeaned by bad systems for decades now. The gulf between their cultural value and economic value is tragically large. The work that writers do is important: it shapes how we think, how we cooperate with others, and who we are. It is the foundation of a functioning society. And yet, in recent years writers have continued to be shunted down the economic order, forced to sublimate themselves to fickle gatekeepers and algorithms while living with acute financial anxiety.

I just wish he’d see that when he used the labor of working-class, often marginalized progressives to patronize and enrich the conservatives marginalizing them, he became exactly the kind of fickle gatekeeper he decries.

Everything Awesome

Polley, a Canadian actor and activist, published one of six essays collected in her book “Run Towards the Danger.”

In it, she recalls her terrifying experience as a child actor in Terry Gilliam’s “The Adventures of Baron Munchausen” — and, crucially, her changing relationship to the film, the experience, and Gilliam over the years.

Many celebrities who write books simply write things down as they recall them, and we all gossip about the most salacious bits and move on. But Polley has done a lifetime’s worth of work processing these events, revisiting them over and over with the people who were there and taking meaning from each iteration and interaction.

A portrait artist re-painting thrift finds into amazing fan works, Julia went all-out in turning a bland dime-a-dozen shepherd boy statue into a remarkable goth objet d’art.

I…just. Yeah.

If you were into hip-hop in the Aughties, you know about the Ruff Ryders.

Or…do you? Because I’d never heard of Yayi Ramos, let alone her central role in building up a bunch of street racers into the iconic motorcycle crew that was synonymous with DMX’s record label.

Nina St. Pierre’s research and writing are absolutely on-point in this one, walking us not only through all the incredible things Ramos said, did, or was a part of, but how and why she came to do, say, and be a part of all those things. Not to mention why we don’t all already know her name, what DMX’s death meant to and for her, and how she ends this story much the same person she was at the beginning.


I haven’t had much fiction-writing time over the last little bit here, because I had three teenagers wrapping up public school for the year — and one wrapping up public school forever!

That said, I wrote, revised, and submitted a brand-new fantasy short story in a flash of inspiration. I’m super pumped about this one, called “The Steepest Cliff,” and I’ll be sure to let you know if it finds a home.



Ty Schalter

Professional writer & talker (@FiveThirtyEight, etc.). Sports things & nerd stuff. Rather cleverer than most men; mistakes correspondingly huger. He/him.