Plotting the Media Rebellion from a Hidden Bar
Why the lifeboat is starting to look a lot better than the cruise ship.
February 27th 2026
Lower East Side, NY
I spent last night in a room full of people who usually only exist as disembodied avatars in my inbox.
To get in, I had to walk through an underground corridor that smelled of damp brick and prohibition-era corpses, finally emerging into a genuinely ornate speakeasy called The Back Room. It felt entirely appropriate. If you’re going to gather a group of writers and artists ostensibly plotting the overthrow of legacy media, you should probably do it in a place that requires a secret entrance and a minor tetanus risk to access.
It was the Substack Bestsellers event, a room packed with the writers, artists, musicians and others who have somehow convinced the internet to actually pay for human-made words and pictures again. It’s a strange (but great) feeling to put 3D, carbon-based faces to the 2D names I’ve been reading for years. I bumped into Liza Donnelly (who mercifully survived live-drawing the State of the Union AND being on my show this week), Jeremy Caplan from Wonder Tools, Suzy Weiss from The Free Press, and my friend Samantha Dion Baker from Draw Your World, squeezed in with a number of the people who actually work in the Substack engine room and keep the whole thing humming along.
At one point, Hamish McKenzie, one of the co-founders grabbed a microphone. He opened with a line that instantly warmed my cold, cynical heart:
“I’m writing a book. It’s called How to Save the Media - and it’s called that mostly so I can piss off everyone in New York…”
I didn’t hate it. There is an entrenched, cocktail-party snobbery in this city’s media establishment that desperately needs a poke in the eye. But then he pivoted, and what he said next is exactly why I’ve tethered my own leaky dinghy to this particular ship:
“But really, it’s not quite the right title. Because what we’re actually trying to do -what the book is about, what Substack is about, what this room is about- is rebuilding the media.”
We don’t have anything against the institutions that were built on the old infrastructure of previous eras. We wish them the best. But our job isn’t to prop up these ailing businesses.”
I stood there, sipping my Negroni from a coffee mug, and realised how aggressively correct he is. For years, cartoonists, writers, and journalists have been acting like palliative care nurses for dying newspapers and magazines. We’ve watched budgets get slashed, editors and art departments get fired, and our own work get buried under a mountain of programmatic banner ads for fungal creams and weird belly fat tricks. We’ve absorbed the stress of corporate cowardice and shrinking column inches. Hamish isn’t suggesting we throw a brick through the window of Condé Nast. He’s just saying we don’t have to actively go down with the ship.
I’ve been cynical in the past about all of this, but on the topic of Substack being something different from the enshitified social media platforms, I do have some hope.
“Our job is to build something new, and to show people that this media ecosystem can be better. That there’s something to hope for. That it can be more open, more diverse, more interesting, richer, and more valuable than at any time in history…
…And that job is not Substack’s job - It’s the job of everyone in this room - the people doing the work, showing what’s possible when you serve communities more deeply and start with a fresh page.”
When you sit alone in a studio all day, scratching away with a dip pen, it’s incredibly easy to feel like you are just shouting into a void. You forget that there is an entire ecosystem of other solitary neurotics doing the exact same thing.
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What Hamish was saying (and what this platform actually facilitates)is that we aren’t just independent contractors begging for scraps from the old gatekeepers anymore. We are the new infrastructure. By serving our own weird, niche communities, we are collectively building a lifeboat that is vastly superior to the cruise ship we all jumped off of.
I walked back out through the damp tunnel and onto the chaotic, garbage-scented streets of the Lower East Side. My phone buzzed in my pocket with a new notification that someone had upgraded their subscription to paid. The timing was perfect. It felt like a small piece of a much more hopeful future for whatever the hell it is I’m doing on here.
Anyway. Thank you for reading my work and putting up with these musings. I’m keen to hear what you think- throw some thoughts in the comments.
‘til next time!
Your pal,
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What do you mean by “But wait, there’s less?” I look for Morris and find that instead. 🥺 Regarding the cofounder’s remarks, I suppose that time will tell.