“You cannot write a line of code that replaces the invisible labour, the thousands of terrible rough sketches, and the deeply human derangement required to make a truly great cartoon.”

If you try to launch a print humor magazine in the 21st century, most financial advisors will tell you to just set your money on fire instead; it’s faster, it requires less paperwork, and it keeps you warmer in the winter.

We live in the era of the digital churn. We live in an ecosystem where corporate media conglomerates are continuously gutting their editorial staff, pivoting to video, pivoting away from video, pivoting to AI slop, and generally treating the written word and the drawn cartoon as disposable ephemera. The conventional wisdom is that print is dead…

But if you’ve been reading this newsletter for more than five minutes, you know I am obsessed with the messy, unglamorous back-end of making a living as an artist. I love pulling back the curtain on the creatives who look at the “churn,” laugh, and figure out how to keep the lights on without selling their souls to the algorithm.

This week on Draw Me Anything, I brought in a guy who looked at a sinking ship and decided to build his own lifeboat.

I was thrilled to host the brilliant Michael Gerber. Michael is the publisher, editor, and mastermind behind The American Bystander, a publication that Newsweek literally called “the last great humor magazine.”

During the stream, we dug into exactly how you resurrect a print humor magazine in the 21st century without setting mountains of corporate cash on fire. It is a story of grit, absurd luck, and a publishing model that bypasses the corporate overlords entirely. But before we get to the Chinese oligarchs and the naked Kickstarter launch, we have to go back to a very small room in the One World Trade Center.

The Everest of Cartooning and the Mouse in the Car

My introduction to The American Bystander didn’t happen on a newsstand. It happened in the absolute epicenter of the New York cartooning world.

It was late 2014, maybe early 2015. I was a relatively new immigrant to America, still trying to figure out the brutal mechanics of the New York publishing scene. To my brain, the ultimate peak of the industry -the absolute Everest of cartooning- was getting into MAD Magazine and getting into The New Yorker. Those were the twin pillars of the comedy art world. Everything else was just scenery.

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I was sitting at The New Yorker in the cartoon lounge. Now, let’s be honest about the cartoon lounge at that time: it wasn’t really a “lounge” anymore. It was just a small room off to the side from where cartoon editor Bob Mankoff’s office was located. But the physical space didn’t matter, because of who was in it.

The legendary Sam Gross was sitting in the room. He was positioned right below a giant framed picture of his absolute classic cartoon—the one with the mouse driving the wind-up car. If you’re a cartoonist, sitting in a room with Sam Gross was like a guitarist sitting in a room with Keith Richards.

Sam was holding a copy of a magazine I had never seen before. “Kid, have you heard of this magazine?” he asked me.

I looked at the cover. The unmistakable, beautiful line work of Arnie Roth stared back at me. It was Issue Number Six. “I’m embarrassed to say that I haven’t heard of it,” I admitted.

Sam started explaining what it was, and as he flipped through the pages to show me the cartoons, my jaw hit the floor. I was looking at a murderers’ row of comedy art. “This is everyone I love,” I remember thinking. “These are all my favorite cartoonists in here. What the hell? How long has this thing been around?”

Sam saw the absolute shock on my face. “Yeah, right?” he smiled. “You should submit to this.”

Naturally, the moment he said that, the impostor syndrome kicked in with the force of a freight train. I looked at the names on the pages. I don’t belong in here, my brain screamed. This is ridiculous. These are giants in here. I don’t belong in here.

I was so completely enamored with this magazine, yet I had absolutely no idea it even existed.

When I told this story to Michael on the stream, he just laughed. “Well, that’s kind of the story of the business right there,” he said.

“Everybody loves it. Very few people know about it. We’re always trying to figure out how to get more people to know about it.”

Fast forward to today, and I am deeply proud to not only be a contributor to The Bystander, but to have hosted its “re-founder” to talk about exactly how this impossible publication came to exist.

The Trifecta and the Pitch

To understand The American Bystander, you have to understand the pedigree of the people who originally conceived it.

When I first sat down to chat with Jeremy Caplan about artificial intelligence and digital productivity tools, I genuinely did not think we would end up talking about him playing the violin. I certainly did not expect the conversation to pivot into a deep, philosophical appreciation for the irreplaceable magic of humans sitting in a room together, simply enjoying a live performance.

But tha’s the funny thing about talking to someone who spends their life evaluating machines. You inevitably end up talking about what it means to be human.

The frictionless technological utopia we were promised feels increasingly like a relentless, exhausting deluge. Every week brings a new platform to master, a new algorithm to appease, and a new artificial intelligence threatening to automate us into oblivion. It’s like drinking from a fire hose while someone yells at you to “pivot to video!”

This is exactly why I was so incredibly relieved to sit down with Jeremy on this episode of Draw Me Anything.

Jeremy is a rare beacon of sanity in the digital miasma. He is the Director of Teaching and Learning at CUNY’s Newmark Graduate School of Journalism. He is a former journalist for Time Magazine. Before that, he was a classical violinist. But more importantly for my own daily survival, he is the creator of the massively popular Wonder Tools newsletter on Substack. Jeremy spends his days wading into the chaotic, deeply overwhelming waters of the internet. He tests, breaks, and reviews new apps, software, and digital features so the rest of us don’t have to waste our precious human hours doing it.

Distilling the Chaos

We kicked off the stream talking about the exhaustion of trying to keep up with tech news. It is not just about discovering new tools anymore. It is about tracking the constant, aggressive updates to existing tools. ChatGPT has a new voice feature. Gemini just launched a massive update. Claude is now doing something entirely new with your phone. And you can’t opt out of it.. It never stops.

Jeremy explained that his superpower for distilling this madness down to accessible, bite-sized pieces actually came from his time writing for Time for Kids. When you have to explain complex global news to an eight-year-old in exactly one hundred words, you learn to cut the jargon immediately. You learn to anticipate a human reader’s questions and preemptively answer them.

He also cited the legendary tech writer Walt Mossberg as a major mentor and influence. Mossberg succeeded wildly at The Wall Street Journal because he approached technology not as a deeply entrenched engineer, but as an ordinary guy just trying to figure out how a tool could actually be useful in his daily life.

“I find writing to be extraordinarily difficult. I read The Elements of Style. I read Anne Lamott’s Bird by Bird. I read David Sedaris constantly to study comedic pacing and essay structure. But actually getting the words out of my head and onto the page feels like passing a kidney stone…”

That is exactly what Jeremy does with Wonder Tools. He doesn’t just list fifty new AI tools that launched on Product Hunt this week. He gives you three specific, highly actionable ways to use one feature of NotebookLM to make your Tuesday slightly less miserable. He gives you templates. He shows you what a forty-page deep research report from Gemini actually looks like, so you do not have to spend twenty minutes generating one just to see if it is useful.

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Evergreen Processes over Disposable News

One of the most fascinating things about Jeremy’s approach is his focus on evergreen content. We’re constantly blasted with disposable news. A tech CEO gets fired, a new app launches and dies in a week, a company changes its name. Jeremy actively avoids the daily churn. He wants to create resources that a reader can save and return to three weeks later, knowing the information will still be fundamentally useful.

This really resonated with me. I told him about a post I wrote on Medium over a decade ago. People constantly ask me how I manage to juggle cartooning, stand-up comedy, writing, and running a business without completely losing my mind. The answer is timeboxing. I work strictly from a calendar, not a to-do list. I estimate how long a task will take, block it out in my iCal, and adjust the time block later if it took longer or shorter than expected.

I wrote a simple, straightforward piece explaining this exact process. I thought it was old news. Cal Newport had written about it years prior. But the piece went incredibly viral, and I made two thousand dollars from the Medium partner programme purely off that one specific workflow explanation. Sometimes the most valuable tools are not shiny new apps. Sometimes, they are just fundamentally sound ways of organising a chaotic human brain.

The Ethical Calculus of AI

We eventually had to talk about the elephant in the room. Artificial intelligence…

I frequently get accused of being either a doomer or a total Luddite, but the truth is, I am an early adopter. I was one of the very first cartoonists in my circle to embrace Wacom tablets, Cintiqs, and the iPad Pro. I actively test out tablets for companies like Xencelabs. I do not shy away from folding digital tools into my workflow when they help automate the absolute drudgery of administrative freelance life.

However, the rapid acceleration of generative AI requires a lot of mental arithmetic. I told Jeremy about my personal ethical boundaries. I use Grammarly for proofreading. I am currently experimenting with Gemini for deep research. But I absolutely refuse to use Meta AI or Elon Musk’s Grok because I fundamentally distrust the ethics of the people building them. I opt out of the platforms where I find the creators ethically compromised.

Putting these streams together, wrangling brilliant guests, manually untangling the spaghetti bowl of a brain to pull out the best insights, and writing these recaps requires a heady cocktail of intense caffeine and sheer willpower. If you value this little digital monastery, please consider upgrading to a paid subscription for just $1 a week. It pays for my time, repays the time and labour of writing these up, and keeps Morris supplied with the unnecessarily expensive dog food he demands…

Jeremy had a fascinating, highly pragmatic take on this. He acknowledged the massive macro issues. He is deeply aware of the environmental cost of data centres, the terrifying water usage, and the flawed predictive models being used to evaluate people in hospitals and prisons. But he treats his newsletter strictly as “service journalism.”

He used a brilliant restaurant analogy. When we go out to eat, we sometimes evaluate the ethical supply chain of the ingredients, the working conditions of the farmers, and the environmental impact of the transportation. But other times, we just need to eat a sandwich because we are hungry. He doesn’t believe we need to litigate the macro ethics of AI every single time we try to automate a tedious spreadsheet or fix a typo. He leaves the heavy investigative journalism to the experts, specifically citing Karen Hao’s brilliant book Empire of AI, and focuses entirely on practical utility.

The J. Jonah Jameson Editor

I find writing to be extraordinarily difficult. I read The Elements of Style. I read Anne Lamott’s Bird by Bird. I read David Sedaris constantly to study comedic pacing and essay structure. But actually getting the words out of my head and onto the page feels like passing a kidney stone.

Because I no longer work in a physical newsroom, I deeply miss having a ruthless editor. When I was coming up in newspapers at nineteen years old, I had a classic, cantankerous, ink-in-his-veins editor. He was a J. Jonah Jameson type who had absolutely no compunction about telling me my work was complete garbage. It hurt my precious feelings constantly, but I learned faster than I ever would have with a polite sycophant.

Since I can’t afford to hire a human to yell at me in my apartment, I built a custom AI editor in Gemini. I programmed it with the specific persona of a grumpy, hard-assed, chain-smoking newspaper editor. Now, when I finish a draft by hand, I feed it to the bot. It yells at me about my weak verbs, my terrible grammar, and my overly long paragraphs. I ignore half of its advice because I know the rules well enough to break them, but it forces me to actively defend my choices.

Jeremy agreed completely. He relies heavily on Claude Projects for his micro-editing. He feeds it all of his past writing to establish context, background, and tone, and then uses it as a highly critical sparring partner to catch redundant phrasing and double commas.

He pointed out a provocative but entirely true reality. There are incredible human editors out there. But the average human copy editor simply doesn’t have the bandwidth, the time, or the willingness to ruthlessly tear apart paragraph four and analyse your four different verb choices on a Tuesday night. An AI will do it instantly, comprehensively, and without worrying about hurting your feelings.

Drawing by Hand Before Hitting Undo

This brings us right back to the violin. We talked about where different artists draw the line with these tools. I brought up a story from a previous stream with Liza Donnelly, the brilliant New Yorker cartoonist. She mentioned using AI purely as a brainstorming partner to bounce ideas around.

Our mutual friend, the wonderful British cartoonist Alex Hallatt, heard that and decided to try it. Alex took some scattered, messy notes from a walk, fed them into an LLM, and started riffing on gag premises. It was a great, highly functional workflow. Right up until the bot cheerfully asked, “Do you want me to draw this for you?”

That is the exact moment the panic sets in. It is the moment you realise the tool wants to replace the human element entirely.

I firmly believe that the wobble in the line, the physical imperfections, and the distinct human voice are the only things keeping us from being completely swallowed by the generic digital void. When young students ask me if they should learn to draw on an iPad, I always tell them absolutely not…

Learn to draw by hand first. Learn the absolute fundamentals with ink and paper. If you draw a bad line with a Hunt 101 dip pen, you cannot hit undo. You have to draw that exact line forty-five times until you get it right. You need those neural pathways to form, and you need to understand the physical mechanics of the craft, before you start relying on digital safety nets. You have to learn how to play the instrument before you let a computer tune it for you.

I spent the rest of the stream doing exactly what I love to do. Drawing wobbly, imperfect lines while navigating the absurdities of the modern world. I am deeply grateful for guys like Jeremy who do the heavy lifting in the digital trenches so I can safely retreat to my analogue drafting table.

Now, if you will excuse me, I need to go figure out why Adobe is demanding another subscription fee.

‘til next time!Your pal,

PS. Look, if this actually did something for your brain (or at least distracted you from the creeping dread of your own inbox for six minutes), please consider restacking this and sharing it with your people. It’s the only way the word spreads.

The Tools We Discussed

* Wonder Tools: Jeremy Caplan’s brilliant, incredibly useful Substack newsletter. If you are overwhelmed by tech, start here.

* Claude Projects: Jeremy’s preferred tool for maintaining context and generating ruthless micro-editing feedback.

* Gemini: The engine behind my custom J. Jonah Jameson editor, and a powerful tool for deep research generation.

* NotebookLM: A fascinating tool for organising notes and research that Jeremy frequently writes actionable guides for.

* IA Writer: A beautifully simple, distraction-free writing tool Jeremy relies on.

* Grammarly: My go-to for catching the embarrassing typos that slip through the cracks at 2:00 AM.

* Wacom & Xencelabs: The digital drawing tablets that keep my freelance career afloat.

The Processes We Discussed

* Timeboxing: The absolute lifesaver of a scheduling method where you work strictly from blocked-out calendar chunks rather than a sprawling to-do list.

* Macro vs. Micro Editing: Understanding the difference between fixing a structural narrative flaw (macro) and tightening up a weak verb in paragraph three (micro).

* Custom AI Personas: Training an LLM with a specific voice and set of instructions to act as a specialised sparring partner for your writing.

Resources and Artists Mentioned

* Cartooning in the Age of AI: Alex Hallatt’s incredibly thoughtful Substack documenting her journey and boundaries with digital tools.

* Liza Donnelly: Legendary New Yorker cartoonist and previous DMA guest.

* Walt Mossberg: The legendary tech journalist who proved that writing for the ordinary user is far more valuable than writing for the engineers.

* Cal Newport: The author of Deep Work and a champion of timeboxing.

* AI Snake Oil: The book by Arvind Narayanan and Sayash Kapoor that Jeremy’s new Wonder Tools book club is tackling first.

* Bird by Bird: Anne Lamott’s absolute bible on the excruciating, beautiful process of writing.

If you joined me last time I had the legendary Kevin “KAL” Kallaugher on the stream, you’ll remember we discussed the “Cartoonist’s Paradox”- the absurd reality where cartooning is incredibly easy to start, but absolutely impossible to stop once it gets its hooks into you. This time around, our conversation shifted gears. Instead of talking about how to get into the game, we talked about how to survive it. We dug into how to stay sane in a politically fractured world, how to defend the analogue line against the digital horde, and the sheer mechanical joy of making marks on paper.

I frequently have moments during these streams where I completely forget I’m hosting a broadcast. I find myself just sitting there, slack-jawed, realising how profoundly lucky I am to have an hour to pick the brains of my absolute heroes. KAL is a legend of the medium. He is coming up on his 50th year at The Economist and is currently putting together a massive retrospective exhibition of his work. Getting to draw alongside him is a ridiculous privilege.

The Outsider’s Advantage: We kicked things off by talking about the absolute circus of modern politics. KAL and I both know what it’s like to be an expat trying to explain American madness to the rest of the world. KAL spent a decade living in the UK, and he noted that being an outsider gives you a unique, clear-eyed view. You aren’t tethered to the deep-rooted tribalism of the country you’re in. You can look at the idiocy on both sides of the aisle and criticise it without feeling like a traitor. It’s a perspective he brings to The Economist, which he praised for its critical thinking and reasoned assessment of global madness.

The Human Line vs. The Human Centipede: We eventually touched on the unavoidable elephant in the room: AI and the internet’s right-wing “meme wars”. KAL pointed out a fundamental difference between a viral meme and a great political cartoon: a cartoon is signed. You know a human being sat down, thought about it, and drew it. In an era of increasing detachment and digital takeover, a hand-drawn line stands out because it has life, energy, and personality.

Or, as Paul Nesja so poetically put it in the live chat: “AI is to creativity as the human centipede is to fine cuisine”. (We probably could have ended the broadcast right there.)

Putting these recaps together requires a unique cocktail of intense caffeine, squinting at my monitor, and manually untangling the spaghetti bowl of my brain to pull out the best insights. If you value this little digital monastery, please consider upgrading to a paid subscription for just $1 a week. It pays for my time, repays the labour of writing these up, and keeps Morris supplied with the good dog food he has foolishly become accustomed to.

The Magic of Crosshatching: KAL is an absolute surgeon when it comes to crosshatching. He explained that the technique really evolved out of necessity in the 19th and 20th centuries. Printing in colour or half-tones was prohibitively expensive, and newspapers used terrible, cheap newsprint that made ink bleed. Cartoonists had to use juxtaposed fine lines to denote colour, shading, and texture. KAL even talked about the maddening challenge of using hard black lines to crosshatch something as airy and shapeless as a sky.

Diagon Alley for Cartoonists: My favourite story of the stream was KAL explaining where he gets his dip pen nibs. Back when he lived in London, an art director sent him to Philip Poole, a legendary pen dealer on Charing Cross Road. KAL found a tiny, unmarked door squished between two buildings and walked into a dark, heavily wooded room filled with tiny drawers of nibs. He described it as disappearing into Harry Potter’s Diagon Alley.

A hunched, cantankerous guy in a white trench coat shuffled out and started handing him nibs to try. KAL eventually settled on the George W. Hughes 1319. Years later, when he tried to order more, the guy informed him they hadn’t been manufactured in 150 years. KAL eventually got a box of 144 of them, and he is still drawing with them today.

The 5-Line Rule: We talked about the difficulty of line economy—knowing when to stop drawing and not overwork an image. KAL told a brilliant story (often attributed to Phil May or R.O. Blechman) about a cartoonist getting confronted by editors in a pub.

The editors complained that the cartoonist was paid an awful lot of money, yet his latest cartoon only had seven lines in it.

The cartoonist replied: “If I could have done it in five lines, I would have charged twice as much”.

Thanks for tuning in!‘til next time!

Your pal,

PS. Look, if this actually did something for your brain (or at least distracted you from the creeping dread of your own inbox for six minutes), please consider restacking this and sharing it with your people. It’s the only way the word spreads.

The Tools We Talked About:

* George W. Hughes 1319 Nibs: KAL’s unicorn tool of choice. Good luck finding them; they haven’t been made in a century and a half.

* Hunt 101 Imperial: My wobbly weapon of choice.

* Duo-Shade Board: The chemical-laden drawing board that old-school tabloid guys used to use to pull out different shading tones.

The Artists We Discussed:

(Warning: Clicking these links will result in a minimum three-hour Wikipedia rabbit hole.)

* David Levine: The absolute master of crosshatching and caricature.

* James Gillray: The godfather of the political cartoon. His work was so biting that the Royals used to send people to buy out his entire print run just to hide the drawings.

* David Low: The brilliant New Zealand cartoonist who ended up on Hitler’s kill list for his work.

* Ronald Searle: The man whose inky fingerprints are on the style of almost every modern cartoonist alive.

* R.O. Blechman: Legendary graphic designer and illustrator (and possible originator of the 5-line story).

* Paul Rigby & Bay Rigby: The Australian father/son duo who dominated the NY Post and Daily News tabloid cartooning wars.

* Pat Oliphant: The Aussie who brought the energetic, sprawling tabloid style to America.

* Bill Mitchell & Peter Broelman: Absolute masters of Australian editorial line economy.

* Catherine Woodman-Maynard: The Minneapolis graphic novelist who launched “Comics for Change” in response to local tragedies.

Other Resources:

* KAL’s Substack: If you aren’t subscribed to KAL yet, fix that right now. He is generously opening his sketchbooks and sharing a lifetime of process and wisdom.

* Comics for Change: The initiative started by Catherine Woodman-Maynard that gathered over a thousand entries worldwide.

Now, if you’ll excuse me, I need to go see if I can find a guy in a white trench coat hiding in a London alleyway…

I live in an ancient little apartment a block from Times Square, because I love cooking dinner in my bedroom.

It’s more of a ‘Pre-War Cupboard’ really. I ordered a mini fridge the other day because I needed a guest bedroom. Morris, my French bulldog, is asleep on a pile of discarded drawing paper, completely unbothered by the fact that his gourmet kibble requires legal tender. My radiator clangs with the aggressive rhythm of a stolen Citibike being dragged backwards down a flight of subway stairs.

It’s a very particular kind of anxiety. You want to make art, but you also want to occasionally eat a Chipotle burrito (strictly no beans). It’s an impossible Venn diagram. I’ve made my living for twenty-one years as a freelance artist and comedian. I don’t have a day job, I don’t have a side hustle, and I don’t have a wealthy patron bankrolling my Blackwing addiction.

Luckily, Mason Currey came on the show this week. He’s the author of Daily Rituals, a book I devoured during the pandemic, and his new hardcover is out right now. It’s called Making Art and Making a Living: Adventures in Funding a Creative Life.

When I first saw the title, I told Mason my immediate thought process. “I initially, when I got the book, thought it was finding a creative life,” I said. “And I was like, oh no, it’s way more important. Funding! It’s about money.”

We got into the weeds of how historical geniuses paid their bills, and honestly, it’s comforting to realise they were mostly just flailing around like the rest of us.

I started by asking about Arthur Schopenhauer, who managed to dodge a soul-crushing life in mercantile finance solely because his father died and left him an inheritance. I spend half my time wandering the concrete canyons of Manhattan, wondering how to pay my rent, so I had to ask Mason: Is the secret to artistic genius really just having a rich dad who dies at the exact right time?

“James Joyce, for instance, was an absolute nightmare of a human being…”

It turns out, the answer is a complicated ‘yes and no’. We discussed Charles Baudelaire, whose letters to his mother sounded violently familiar. I’ve always carried this quiet, crushing shame that I can’t just sit at a desk at 9:00am and produce brilliance. I struggle with regulating attention on demand and initiating tasks without a heroic amount of friction. When I can’t meet expectations, it feels intensely personal, like a reflection of who I am at my core.

I asked Mason if Baudelaire’s legendary financial chaos was a symptom of executive dysfunction. Mason pointed out that Baudelaire would let pressure build up until he was in a mad panic. “He talks about how he can’t make himself do the thing until it’s built up so much pressure that he finally does it in this explosion,” Mason said. “He sort of had run up so much debt that he’s forced to dodge creditors and continually be moving from place to place.”

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Leaving things until the absolute last second to manufacture adrenaline is a textbook symptom of ADHD. Baudelaire didn’t have the diagnostic criteria to explain his dopamine dysregulation, but he had the frantic, desperate energy of a man trying to outrun his own brain. He blew his inheritance, dodged his landlords, and begged his mother for loans just to buy firewood.

“The odd jobs that used to support young artists have basically evaporated… They’ve been swallowed up by algorithms and artificial intelligence.”

We talked about the absolute absurdity of how some artists survived their financial ruin. John Cage funded his avant-garde music by going on an Italian television quiz show as an amateur mushroom expert. (As one does). He won the modern equivalent of ninety grand and bought a Volkswagen van. I asked, "Are we all just one weird reality TV appearance away from funding our next creative project? Do I need to go on a baking programme and pretend I care about fondant just to afford fresh watercolour pans?” (I’m kidding. I did that already…)

Then there’s Fernando Pessoa, who inherited a hefty chunk of change. Did he invest it sensibly to live off the interest? Hell No! He blew the entire inheritance in less than a year, having an incredibly expensive printing press shipped from Spain to Portugal, of course…

We also spoke about the absurd methods we use to force ourselves into a productive headspace. For sixteen years, the only way I could get my daily newspaper comic strip done was a highly specific, slightly unhinged ritual. I told Mason all about Scotch Bath Sunday. I would get in the bathtub, pour myself a generous glass of peaty Scotch, and sit there with a yellow legal pad. No phones, no iPads, no laptops. Just me, the boiling water, and the looming terror of a deadline.

Mason loved it. “I think there is a little bit of superstition there,” he said, “but there’s also something really powerful about the repetition. You train your mind to get into that particular headspace on a somewhat regular basis.”

Margreet is a brilliant Dutch comic artist and the former Comics Laureate of the Netherlands. She spent three years acting as an ambassador for the medium, literally compiling guides to help teachers get graphic novels onto high school reading lists. She is also someone who intimately understands the frantic reality of a creative life.

The Court Jesters & the Freedom Fighters

Margreet and I talked about the bizarre cultural divide in cartooning. In Australia, people generally look at comic artists like we are overgrown toddlers playing with crayons. It is treated as a silly little hobby. But if you take a train to France or Belgium, comic artists are treated like absolute rock gods.

I told her about a cartooning conference I went to in France called RIDEP. I was standing in a room with cartoonists from Tunisia, Sudan, and China. They had been exiled or forced into hiding for drawing anti-propaganda cartoons against dictatorial regimes. They were actual, literal freedom fighters. I draw jokes about talking dogs. I realised very quickly that I am more of a court jester. It was a profoundly humbling reality check.

Making a living as an artist requires you to constantly ask people for money, which is something most cartoonists are fundamentally terrible at doing. Margreet is an expert in crowdfunding, having run multiple successful campaigns in Holland to bypass the traditional publishing gatekeepers.

The Kickstarter Scam…

But she recently got targeted by a very clever, highly sophisticated Kickstarter scam. Scammers will pledge a massive amount of money to your campaign just to get your attention. Then, they send a highly convincing email from a “notification bot,” claiming your account is suspended, and your money is frozen. They provide a link to steal your credentials. Margreet described it as the digital equivalent of being lured away from a busy high street into a dark alley. We are already sweating over our drawing boards; we do not need thieves making it harder.

Related viewing:

My interview with the Founders of Zoop:

Theology and Annoying Mrs Lee

Margreet has a fascinating background. She originally flunked out of school because she hated the technology, so she pivoted to studying theology at the University of Amsterdam. Both of her parents are ministers, so it was in her blood. While she was there, she drew a comic for the faculty paper called The Adventures of Jesus. (Which sounds like the working title for The Bible).

I completely related to her fascination with religion as a storytelling mechanism. I went to an Anglican high school, and I used to infuriate my Bible study teacher, Mrs Lee. I would sit in the back, drawing cartoons and interrogating the text with the obnoxious persistence of a discount detective. I just wanted to know how the plot holes were resolved. Mrs Lee did not appreciate my feedback. She hated me.

The 3:00 AM Eyeball Hack

The absolute most valuable thing I took away from our chat was a neurological trick for my broken, sleep-deprived brain. We were talking about meditation and dealing with anxiety, and Margreet told me about an EMDR-style hack she uses when she is trapped in a rumination loop.

If you want to read about my annoying high school Bible study questions, a completely bizarre neurological hack to cure insomnia, and the absolute hazard of using a dip pen in bed, consider upgrading to a paid subscription for just $1 a week. It keeps the ink flowing & Morris fed.

Episode Links: Book // Socials // Podcast // Website

If you caught this chat live on Thursday, you know my chat with Sarah Elizabeth Hill didn’t bother with small talk. We dove straight into the deep end.

Sarah writes, produces, and runs Bobi Media. She took $400 and built it into an agency that works with Oscar winners, Deepak Chopra, and brands you see on billboards. On paper, it looks like she just levitated to the top of New York media. Spoiler: nobody floats in this city. You claw your way up, or you get chewed up.

But on Draw Me Anything, we don’t do glossy. We go straight for the mess under the sink. We talked about the invisible sacrifices—the stuff nobody puts on LinkedIn. The reality of trying to keep a business alive in a city that’ll eat you for breakfast if you blink.

Here are a few things we unpacked in the first half of the conversation…

The Reality of the Creator Grind

Turns out, creative brains are actually built for business… if you can keep the lights on, swallow your pride, and remember to actually send the invoice. We talked about those early days, stretching that initial $400 investment, and the sheer, unadulterated panic of realising you are the only safety net you have.

But that same tunnel vision required to build something out of nothing? It’ll burn you out faster than a …ugh. I’m too exhausted. I can’t think of a simile.

Sarah didn’t sugarcoat the human cost of the hustle. She talked about the time the grind nearly broke her completely:

“I was working so much I wasn’t leaving my desk... I hadn’t developed my habits and so was hospitalised, because I couldn’t get my brain to stop spinning.”

Building the “Infrastructure” of You

When your brain is your business, a breakdown isn’t just a personal crisis; it’s a corporate bankruptcy. We talked about the absolute necessity of building a team. And I don’t just mean hiring a virtual assistant. I mean building the infrastructure of you: Accountants. Therapists. The guy who tells you to stop staring at the screen and breathe. All of it.

Sarah made a brilliant point about treating your physical and mental health like non-negotiable client meetings. If you don’t carve out an hour to lift something heavy, walk around the block with the dog, or just stare at the ocean on a Friday afternoon, you’ll crash. The city doesn’t care. The algorithm doesn’t care. You have to work to live, not the other way around.

The “Hell Yeah or No” Rule

New York is an all-you-can-eat buffet of opportunities, which means the most dangerous thing you can do is say “yes” to everything. We dug into Derek Sivers’ famous rule: if it’s not a hell yeah, it’s a no.

“You have to protect your time like it’s the last glass of water in the desert. If you don’t aggressively filter what comes across your desk, you end up building someone else’s dream while yours slowly starves.”

The only way to keep your time from getting mugged by every shiny offer is to know your “Big Why.”

The Reframe, the Churn, and the AI Survival Guide

In the second half of the stream, we got into the stuff that actually keeps you up at night. The heavy hitters. The things we usually only talk about at the bar after the gig is over.

We cracked open the New York Churn- the endless, exhausting loop of people showing up, burning out, and getting spit back out to the suburbs. Sarah handed me a new way to look at the concept of “personal sacrifice” that completely rattled my brain. It made me rethink what it actually takes to stick around, keep your friends, and build a life here that doesn’t fall apart the second the rent goes up.

And then, we finally wrestled with the elephant in the room: Generative AI.

Sarah’s new book, Chat Sh!t Crazy, is all about using these tools to sharpen your sense of self, not erase it. Instead of complaining about the robots taking our jobs, we got into the weeds on how to use AI as a mirror for your own blind spots. We talked about how to survive the AI flood without losing your soul (or your rent money.)

To my free subscribers: If you want the whole thing -the raw, uncut hour- you’ve got to step inside the studio. The full replay is for the folks who keep the lights on and put dog food in Morris’ tummy.

If you care about real art, the messy back-end of the creative process, and actual human connection, I need you in the inbox. Upgrade your subscription. Help keep this thing alive so I can keep bringing you these conversations.

The sheer logistical terror of running a comedy festival is not something the average person truly understands.

You have to convince nearly a hundred highly neurotic, sleep-deprived stand-up comedians to travel to a single location. You have to make sure they get picked up at the airport. You have to house them. You have to pray they have the personal o…

If there’s one thing I’ve been banging on about this week more than anything, it’s that finding a genuinely distinct visual voice in the modern cartooning landscape is brutal.

You need to be instantly recognisable. You need to be deeply funny. You need to build a world. (Oh, and try to make a living doing it.) Tom Chitty has built an entire universe. He is a British cartoonist based in Toronto, a regular contributor to the New Yorker, and an absolute master of the absurd and whimsical (okay, ‘silly’). His characters feature blocky bodies, wide stances, and an otherworldly charm. We sat down for Draw Me Anything yesterday to decode the mechanics of his highly specific, deeply funny brain.

Here is exactly how he builds his worlds…

The Serial Killer Sketchbook

Young artists obsess over perfect sketchbooks. They paint immaculate, highly composed spreads and post them online. It is a complete lie. Real sketchbooks look like the manifesto of a deranged serial killer. Look at the horrendous s**t I just found when I flicked open one of mine…

Tom learned this the hard way in animation school. A tutor looked at his work, told him to stop designing, and ordered him to just start generating ideas. he dropped the pressure of making a pretty picture. He started treating his drawings like handwriting. He now keeps a sketchbook on hand constantly, capturing raw, unfiltered nonsense. Six months later, he opens the book and finds completely forgotten, bizarre ideas that actually make him laugh.

You can’t force inspiration by sitting down and staring at a blank piece of paper. Taking a leaf out of every great artist’s book, he walks to the coffee shop every morning after dropping his son at school. Moving through the world and seeing the horizon literally dislodges ideas from the deep dark recesses of your skull.

The Regret of the “Send” Button

Pitching cartoons is an exercise in psychological torture. You curate a batch of ideas. You arrange them like you are sequencing a Radiohead album. (Yes, we’re exactly the same as Thom Yorke. Thank you.) You convince yourself the order matters. Then you hit send on the email.

The regret is immediate. You look at the batch two hours later and see nothing but glaring flaws. You wonder why you ever picked up a pen in the first place.

Tom survives this weekly cycle by treating it as a boot camp. He gets up, generates ideas, and commits to the sheer volume of the work. Early in his career, veteran cartoonists Matt Diffee and Bob Mankoff gave him ruthless, honest feedback. The ultimate lesson is simple: Do not draw what you think the New Yorker ‘wants’. Draw what makes you completely unique.

Ghost League Baseball and Wonky Parsnips

Tom is launching a Kickstarter on April 1st for an absolute masterpiece. It is called Nooks and Crannies of New York. It is compiled from the fictional chronicles of an eccentric explorer named Baron von Schoogenheimer.

The book is a staggering achievement in world-building. It took him three and a half years to draw. He documents Ghost League Baseball teams, including the Mysterios and their star pitcher Hodge Wang, famous for his penguin-wing throwing action. He documents subterranean trolls making furniture in the interborough tunnels. He draws Roof Mables, who live in disused water towers and help New Yorkers retrieve lost memories.

He grounds the absurdity by pulling from his own family history. He turns a childhood memory of eating Dutch Speculaas biscuits into an elaborate drawing of Schneek’s Belgian magic pedal-powered hot dog production cart.

He also understands the phonetic rhythm of comedy. Some words are just inherently funny. Tom used to run a website dedicated entirely to words with intrinsic humour value. Balloon. Spoon. Guff. Wonky parsnip. He injects this phonetic absurdity into every character name and fictional contraption he draws.

The Caboon and the Fly Ball

Halfway through the stream, we flipped the cameras and started scribbling. Tom uses a Staedtler 0.3 fineliner to achieve his incredibly detailed, controlled line work. After a suggestion from Hue Walker of a Frog on a Bat, he and I began drawing a Caboon, which is a feline-looking primate from his book that accompanies French Canadian taxi drivers to judge the character of potential passengers.

Meanwhile, the live chat was throwing out prompts. Paul Nesja suggested drawing the above-mentioned frog catching a fly ball. I sketched it out, immediately regretting my lack of reference material for amphibian anatomy. Drawing live while trying to conduct a coherent interview is basically an extreme sport, but it forces you to rely entirely on your muscle memory.

Wrestling with glitchy streaming software, fighting the algorithm, and writing these detailed process breakdowns requires a heady cocktail of caffeine and sheer willpower. If you value this virtual bullpen and want to watch the full, unedited video replay of Tom and me drawing live, please consider upgrading to a paid subscription for just $1 a week. It keeps the inkwell full, repays the massive labour, and keeps Morris supplied with the treats he demands.

We are actively fighting a deluge of generic, machine-generated content. You need to support live, human artists who spend years crafting weird, beautiful things. Go to Kickstarter on April 1st and search for Nooks and Crannies of New York. Back the project. Buy the book, and the folks at The American Bystander's Viral Load. Support the absolute necessity of being silly.

Now, if you will excuse me, I need to go burn my sketchbooks before the detectives arrive...

‘til next time!Your pal,

Jason

Tools and Resources We Yapped About Today:

Trying to succeed as a cartoonist is stupid. Trying to succeed as a stand-up comedian is masochistic. Trying to do both simultaneously is a clear cry for psychiatric help. Emily Flake does both, and she makes it look infuriatingly easy.

My guest on Draw Me Anything this week is a cartooning powerhouse. She just won the 2026 Thurber Prize for American Humour. She is one of the rare artists whose distinct comic voice translates perfectly from the printed page directly to the stage. She also possesses a genuinely terrifying amount of hustle. Here is exactly how you build an absurd, multi-hyphenate career without completely losing your mind.

The Alt-Weekly Education

Finding your voice requires failure. You need a low-stakes environment to make mistakes, draw weird things, and test boundaries. For Emily, that was the Baltimore City Paper.

She drew a strip called Lulu 8Ball for the alt-weekly. Alt-weeklies are dead now, which is a massive cultural tragedy. They gave artists absolute freedom. Emily figured out a four-beat joke structure, she honed her timing, and she cussed profusely. The traditional papers would never allow that. She is now bringing Lulu 8 Ball back to life on her brand-new Substack. Subscribe to it immediately please and thank you:

The Fraud Detector (Joke in a Box)

Writing jokes is a terrifying puzzle. I arrogantly assumed I knew exactly how to write one. Then I opened Emily’s physical card deck, Joke in a Box.

I read the exercises. I immediately realised I am a total fraud. The prompts are ruthless, practical, and highly effective. Fellow cartoonist Hillary Fitzgerald Campbell actually used the deck to write a joke and ended up selling a cartoon to the New Yorker. You can still buy this box of magic on Bookshop. Do not buy it on Amazon to fund a billionaire’s joyride.

St. Nell’s and the Ghost Hotel

Williamsport, Pennsylvania is a lumber town. It has haunted hotels and a bizarre vacuum of silence. It is also the home of St. Nell’s…

Emily bought a house out there during the pandemic after heading out there and staying in the haunted 100+ year-old hotel, The Genetti, as a little getaway to save her family from murdering each other in their sleep. Her husband told her they had absolutely no money for a second house, so she launched a Kickstarter and raised fifty grand. She turned the property into a free writer’s residency for women and marginalised genders. Three residents stay at a time for two weeks. They write, they sleep, and they create incredible work.

She even launched an entire comedy festival out there called Nellsfest. The town actually shows up and supports the artists. It is a brilliant community. (A lot of medical professionals, as it turns out.)

Longtime readers will remember our eventful booksigning event there earlier this year:

Hell Gigs and Toddler Jazz

Stand-up comedy is an exercise in public humiliation. We brought Hillary Fitzgerald Campbell onto the stream to discuss the absolute worst gigs we’ve ever survived (with emotional scars).

Hillary’s hell gig involved abruptly stopping a family jazz festival. The organisers forced three women to tell dirty jokes to a room full of toddlers. It is the textbook definition of a comedy nightmare.

Emily performed at a children’s play space in Stroudsburg. The audience consisted of exactly one woman sitting on a couch. The woman only spoke Spanish. She stood in a cavernous echo chamber, speaking English into a microphone taped to a stand with packing tape, essentially making bird noises.

My personal hell gig took place in a Williamsport bar. A massive basketball game played on the screens right next to the stage. The bartender connected her phone to the venue’s Bluetooth speakers. She forgot to turn off her keyboard sounds. I tried to tell jokes while the aggressive tap, tap, tap of her text messages blasted through the sound system… more below:

Boxing and Bombing

Getting punched in the face and bombing on stage are the exact same physical sensation.

Emily boxes. I box. Will Sylvince at the Comedy Cellar boxes. The overlap between comedians and fighters is massive. When you take a hit in the ring, it is not the pain that ruins you. It is the disorientation. You have to force your brain to stay in the game while you are completely compromised.

Comedy is identical. When a joke dies, the room turns hostile. You have to stay entirely in control while you are deeply uncomfortable. You eat dirt, you respect the hustle, and you get back up… I’ve written about this before:

Wrestling with glitchy streaming software, cutting through the digital noise, and writing these detailed recaps requires a unique cocktail of intense caffeine and sheer willpower. If you value this virtual bullpen and want to watch the full, unedited video replay of Emily and Hillary drawing live, please consider upgrading to a paid subscription for just $1 a week.

Thank you Andi Penner, chris eliopoulos, Bear Edwards, Ann Feild, PJ Pierce, and many others for tuning into my live video with Alex Hallatt! Join me for my next live video in the app.

Some notable quotes from this week’s episode:

* “We can’t just be blinkered and think, ‘Oh my God, as creatives, this is an existential threat, and we have to stop it, because we’re not stopping it. It’s like the internet, but bigger.”

* “You can continue doing what you’re doing, the way you’re doing it, but you better be bloody good because you’re going to become an artisan.”

* “You don’t pay the plumber for banging on the pipes, you pay him for knowing where to bang.”

* “Cartoonists die at the drawing board.”

* “AI is coming like the printing press came for monks and illuminated manuscripts. Do you think the monks were pissed off or do you think they were relieved?”

Today’s Draw Me Anything featured the return of the brilliant Alex Hallatt, creator of the syndicated strip Arctic Circle and the Substack Cartooning in the Age of AI.

Alex joined us from Dorset, UK, where the weather is currently “not very lovely,” which is British for “apocalyptic.”

We dove straight into the giant robotic goblin in the room: Artificial Intelligence. Alex approaches this topic with a “scientist brain” (she used to work in clinical research), which makes her perspective refreshingly pragmatic. Instead of just panicking, she’s looking at how to survive. She compared the current AI panic to the early days of digital photography, when old-school photographers insisted it wasn’t “real” photography. Now, shooting on film is an “artisan” pursuit. The lesson? If we want to keep drawing by hand, we’d better be bloody good at it, because we are all becoming artisans now.

One of the funniest moments came when Alex described how she uses AI to handle the “tedious” stuff, like finding the secret service menu on her storage heaters, so she didn’t have to pay an engineer £200 to push three buttons. It’s the “plumber analogy”: you’re not paying for the button pressing; you’re paying for knowing which button to press. And right now, AI knows where the buttons are.

We also talked about the “enshittification” of platforms like Amazon, where search results are now buried under AI-generated guidebooks and sponsored slop. It’s getting harder for independent creators to be found, which is why building a direct relationship with readers (like on Substack) is the only real lifeboat. As Alex put it, “I want to have a chat... human connection has real value in an AI world.”