Copywriting Wisdom: Halbert, Bukowski, Vonnegut & Fladlien

Jason Fladlien:

My favorite copywriting resource is still The Gary Halbert Letter. It taught me how to move people, not just inform them. But over time, I realized something important: if all I did was study copywriters, I’d end up sounding like everyone else—and no one remembers ‘everyone else.’

So I started channeling other voices. I studied Bukowski to strip away the fluff and write with brutal honesty. I read Vonnegut to understand how to explain complex truths with disarming humor. And I kept Gary in my corner for his ruthless clarity and persuasion. It’s a weird trio, sure—but it gave me a voice people could trust. A voice that sells because it feels human.

This roundtable is my dream conversation—Gary Halbert for structure, Bukowski for grit, Vonnegut for heart. I invited them here not just to talk about copywriting, but to show you what happens when sales meets soul. Not everyone will agree on everything. But that’s the point. You don’t find your voice by copying others. You find it by listening deeply… and then writing your truth.

(Note: This is an imaginary conversation, a creative exploration of an idea, and not a real speech or event.) 

Voice vs. Formula: Can Copy Be Too Perfect to Convert?

Moderator: Jason Fladlien
Guests: Gary Halbert, Charles Bukowski, Kurt Vonnegut

Jason Fladlien leans forward in his chair, a grin spreading across his face as the mic warms to life.
"Gentlemen," he begins, "we’re living in the golden age of templates. You can buy swipe files the size of a dictionary. Plug and play. Drag and drop. But let me ask you this—can copy be too perfect to convert? Does clinical precision kill connection?"

A pause. A spark. Gary Halbert is the first to respond, lacing his fingers together like he’s about to share a secret.

Gary: “Look, I’ll tell you something. Most people write like they’re scared. Scared of breaking the rules, scared of sounding stupid, scared of being different. That’s why they cling to formulas like they’re life vests. But formulas don’t sell—feelings do.

Don’t get me wrong. I love a good structure. Hell, I built some of the best in the biz. But if your copy feels like it’s assembled from a kit, people will treat it like Ikea furniture—functional, forgettable, and replaceable.”

Charles Bukowski snorts, pulling a cigarette from a crushed soft pack that seems to have time-traveled with him.

Bukowski: “Too perfect? Christ, life’s a mess. And writing should be too. When a man writes with no dirt under his nails, no broken heart, no bar fight behind his words, then what the hell is he even doing?

I never gave a damn about your templates. What I gave a damn about was bleeding truth on the page. That’s what makes people stop. Not ‘proven headline structure #7’. But raw voice. Unfiltered. Undiluted.”

Jason chuckles, sensing the electricity crackling between the speakers.
"Kurt, what about you? Can structure kill soul?"

Kurt Vonnegut smiles, leaning back in a worn leather chair, legs crossed in academic ease.

Vonnegut: “Structure is not the enemy, Jason. Bad structure is. And slavish obedience to it. I always told my students: Use the time of a total stranger in such a way that he or she will not feel the time was wasted.

The trouble with perfection in copy is that it becomes predictable. And predictability is death. You must dance with the reader. Surprise them. Seduce them. Make them laugh. Make them cry. Then ask them to buy something, and they just might say yes.”

Jason: “So you're saying voice—the writer’s you-ness—must lead, not the formula?”

Gary leans forward, eyes sharp.

Gary: “Exactly. A good formula is like a spine. It holds things up. But what fills it out—the flesh, the soul—that’s the writer. If you’re just regurgitating what worked for someone else without any of your own flavor, your copy's dead on arrival.

Here’s the test: if your best friend read your ad, would they know you wrote it? If not, go back and try again.”

Bukowski grumbles approval, tapping ash into a coffee mug.

Bukowski: “When I write, I want it to feel like a punch to the gut. Even if it’s about toilet paper. People are too numb to feel safe, polished words. You want them to feel alive.

If you write like everyone else, you’ll be forgotten like everyone else.”

Jason: “But isn’t that a risky move? Raw voice, unfiltered emotion—can that alienate prospects?”

Kurt nods thoughtfully.

Vonnegut: “Of course it can. But so can blending in. The reader isn’t a machine. They’re a bundle of nerves, memories, regrets, and dreams. Talk to them like that.

The risk is in being real. But that’s also the reward.”

Gary: “The best copywriters aren’t just writers—they’re performers. We’re on stage every time we hit publish. And if you’re not willing to show your face, your soul, your rhythm—why should anyone buy from you?”

Jason pauses, letting the weight of the words sink in. Then he turns to the audience.

Jason: “So what I’m hearing is this: templates are fine to start, but if your voice gets buried, your conversions will too. The perfect copy isn’t flawless—it’s fearless.

Gary says: Let the formula hold your ideas, not replace them.

Bukowski says: Strip it down. Write like you’ve got nothing left to lose.

Vonnegut says: Lead with humanity. Honor the reader’s time with surprise, wit, and warmth.

Gentlemen—final thoughts?”

Gary: “Use the formula to get unstuck. Then set it on fire.”

Bukowski: “Write like the rent's due and your soul’s on the line.”

Vonnegut: “Write for one person who needs it. Then trust they’ll tell others.”

Jason closes with a slow nod and a smirk.

Jason: “Copy isn't just about what works. It's about what moves. And if you can move them, you can make them click, buy, believe, or even become someone new. So don’t aim for perfect. Aim for unforgettable.”

The Role of Suffering and Humor in Writing That Sells

Moderator: Jason Fladlien
Guests: Gary Halbert, Charles Bukowski, Kurt Vonnegut

Jason Fladlien wastes no time today. With a spark in his eye, he opens:
“Alright guys, let’s talk about something we all feel but rarely dissect—pain and humor. These two forces—raw suffering and unexpected laughter—seem to move people more than any sales technique ever could. So the question is: how do pain and humor play into writing that sells?”

Charles Bukowski lights up, not just the cigarette, but the mood too.

Bukowski: “That’s the only thing worth writing about. Pain. Not the drama-queen kind. Not the Hollywood script kind. I’m talking about the ordinary hell of being alive. Loneliness. Rejection. Hopeless jobs. Cheap coffee.

You give me a man in a room wondering if he matters, and I’ll show you a reader who can’t look away. That’s where the sale happens. Not on some landing page. But in the mirror you hold up.”

Jason: “So pain creates connection?”

Bukowski: “Pain is the original language. Everyone speaks it, even if they deny it.”

Jason turns to Gary Halbert, who’s nodding with a smirk.

Gary: “You know what sells? It’s not the product. It’s relief. Relief from pain. Every offer worth a damn is a bridge out of some kind of suffering.

Think about it: Weight loss? That’s relief from shame. Financial freedom? That’s relief from fear. Even the humor in an ad? That’s relief from boredom or tension.

If your copy doesn’t acknowledge what your reader’s going through, then why should they trust you to help them out of it?”

Jason: “So do you consciously write from pain?”

Gary: “I write from understanding it. Pain isn’t just a trigger—it’s a mirror. If your reader sees themselves in your words, they’ll believe you understand them. And if they believe you understand them, they’ll follow you anywhere.”

Kurt Vonnegut chimes in, voice gentle but firm.

Vonnegut: “And that’s where humor comes in. Not to distract, but to defuse. Humor is the spoonful of sugar, sure—but it’s also the scalpel.

I’ve always said, Laughter and tears are both responses to frustration and exhaustion. I prefer to laugh, because there is less cleaning up to do afterward.”

Bukowski chuckles, taking a long drag.
“Yeah, humor’s what keeps you from going mad. And keeps the reader close, too.”

Jason: “So, is humor just a trick to keep attention? Or something deeper?”

Vonnegut:

“It’s empathy in disguise. When you laugh with someone, you momentarily share a truth. That’s sacred. Even in sales.

And when you disarm someone with laughter, you lower their shield. That’s when you tell them what matters. That’s when they hear it.”

Gary: “People don’t buy when they’re defensive. They buy when they feel understood—and safe. Humor does that. It lowers the guard. Then you slip in the pitch like a friend.”

Jason: “But is there a line? When does humor get in the way?”

Bukowski:

“When it’s used to hide instead of reveal. Humor should point to the wound, not avoid it. You want to sell? Show me you’ve suffered like me. Then make me laugh in spite of it. That’s what builds trust.”

Vonnegut:

“Exactly. The best humor is honest. Not clever for the sake of clever. But humane.

Think of the human brain like a clenched fist. Suffering makes it tighten. Humor opens it just long enough to accept a new idea—or product.”

Jason leans forward, energized now.
“I love that. Humor opens the fist. Pain shows the wound. Copy that converts does both. It exposes and soothes. Stings and heals. That’s art.”

Gary:

“And it’s why some of the best copywriters weren’t born in marketing—they were born in the fire. Single moms. Broke artists. Divorced six times.

They write like their life depends on it. Because it does.”

Jason: “So what does that mean for today’s copywriters who grew up on marketing courses instead of life bruises?”

Bukowski, grinning:

“Then go get bruised. Or at least listen to those who have. If you’ve never been desperate, it’s hard to sell to someone who is.”

Vonnegut:

“And if you can’t suffer it, at least witness it. That’s what writers do. We hold our breath long enough to hear what others are choking on.”

Jason Fladlien leans back, his voice quieter now.

“So here’s what I’m hearing:

• Bukowski says pain is the only real connection point. If you can’t write from the wound, don’t bother.

• Gary reminds us that the buyer’s pain is the bridge we must build. Offer relief, not features.

• Vonnegut tells us humor is the scalpel that gets past the reader’s defenses and delivers the medicine.

Final thoughts?”

Gary: “You’re not just a copywriter. You’re a healer with a headline.”

Bukowski: “Make ‘em cry. Then laugh. Then buy.”

Vonnegut: “Make the reader feel seen. Then give them a way forward.”

Jason: “And that, my friends, is how you write words that heal, entertain, and sell.”

Selling to Humans — How to Make People Feel, Not Just Buy

Moderator: Jason Fladlien
Guests: Gary Halbert, Charles Bukowski, Kurt Vonnegut

Jason Fladlien opens with a calm but piercing tone.

“Let’s cut through it. In a world obsessed with conversions and click-through rates, here’s the simple question: How do you write copy that makes people feel—and not just buy? Because if all we’re doing is tricking folks into clicking, we’re not building anything that lasts. So... how do we get to the heart of it?”

Gary Halbert is the first to lean in, his voice laced with certainty.

Gary: “Let me tell you something most copywriters don’t want to hear: People don’t want to be sold.

They want to be seen. They want to feel like you get them.

That means before you even pitch a solution, you better describe their problem in a way that makes them say, ‘How the hell did he know that?’

You win not when they buy, but when they nod.”

Jason: “So how do you reach that moment of nodding?”

Gary: “Empathy, man. And specificity. Don’t say, ‘You’re struggling.’ Say, ‘You’re up at 2AM, scrolling, wondering if you’re too late to fix your life.’ Make it real. Make it them. Then you have them.”

Charles Bukowski speaks up next, raw and unfiltered as always.

Bukowski: “Most people write copy like it’s a speech. But it’s not. It’s a conversation. One-on-one. Whispered at 3AM when everything else is quiet.

If I feel like you’re talking to the crowd, I’ll walk away. But if you talk to me, like I matter, like you’re telling the truth...

Now you’ve got me.”

Jason: “And how do you do that—write to just one?”

Bukowski: “Easy. Pick someone. A friend. A lover. Hell, your landlord. Write only to them. Bleed it on the page. Then cut away everything that doesn’t make them feel something.”

Kurt Vonnegut joins in, his voice measured, wise.

Vonnegut: “We are not in the business of moving wallets—we are in the business of moving hearts.

And people’s hearts don’t respond to logic. They respond to stories.

Tell the truth. Wrap it in narrative. Make it human. That’s how you make them feel.”

Jason: “So is storytelling the key?”

Vonnegut: “Story is the soul of humanity. A bullet list never changed a life. But a story about someone like me? That stays.

And when it stays, it sells.”

Gary: “I’ll back that up. A list of benefits is forgettable. A story is unforgettable. The best copywriters are damn good storytellers. They just do it fast, and with purpose.”

Jason: “And how do you avoid the trap of emotional manipulation?”

Bukowski answers first, a rare seriousness in his tone.

Bukowski: “Manipulation is when you fake it. When you exploit pain you’ve never felt. But if you write from something real—some moment you lived—it ain’t manipulation. It’s connection.

You can tell when a writer’s just guessing at your pain. It reeks. But when they’ve been there? You feel it in your bones.”

Vonnegut: “Exactly. It’s the difference between writing at someone and writing with them.

When your words say, ‘Me too,’ you create a bridge. And across that bridge, trust walks in.”

Jason nods, then raises a key challenge.

Jason: “But what about urgency? Scarcity? Fear of missing out? These are pillars of high-converting copy. Can we really focus on emotion without losing the sale?”

Gary grins.

Gary: “Hell yes. Those tools still matter. But here’s the thing—urgency works best when you care.

If I believe you’re truly trying to help me, and the deadline is real, I’ll act.

But if your entire pitch is built on a fake timer, with no heart? I’ll bounce. And I won’t come back.”

Bukowski, nodding:

“Deadlines don’t move people. Desperation does. Truth does. Soul does.”

Vonnegut: “And let’s not forget: Emotions aren’t always heavy. Sometimes, a smile sells better than a warning.

Humor, wonder, hope—these are also currencies. And they’re often overlooked.”

Jason turns to the audience, leaning forward slightly.

“Let’s tie this up.

• Gary says: Speak to their truth with precision, and use structure to amplify—not replace—emotion.

• Bukowski says: Write to one soul, not a demographic. Say what hurts. Say what heals.

• Vonnegut says: Emotions are the real sale. Story, empathy, and authenticity are your scalpel.

Final words?”

Gary: “Make them feel, and you won’t need to convince them. They’ll convince themselves.”

Bukowski: “The sale is just the side effect. The connection is what matters.”

Vonnegut: “Don’t aim to sell. Aim to matter. If you matter, the money will follow.”

Jason closes:
“Selling to humans means writing like one. If your words carry warmth, honesty, and intention—they’ll do more than convert.
They’ll stay.”

Literary Theft or Alchemy? Blending Art into Commerce

Moderator: Jason Fladlien
Guests: Gary Halbert, Charles Bukowski, Kurt Vonnegut

Jason Fladlien looks around the roundtable with a sly grin.
“Let’s get real about something every copywriter does but few talk about... borrowing.
From Gary’s famous headlines to Bukowski’s grit to Vonnegut’s wit—at what point does borrowing from artists cross into theft? Or is it all just alchemy—taking raw ideas and turning them into gold?”

Charles Bukowski barks out a laugh and flicks an imaginary ash from the corner of his mouth.

Bukowski: “Everyone steals. The trick is stealing with soul.

If you’re just ripping lines to sound cool or smart or poetic, you’re a thief and a poser.

But if you take what someone else said and run it through your bloodstream, twist it through your misery and truth until it’s unrecognizable—now you’ve made it yours.”

Gary Halbert leans back, nodding slowly.

Gary: “Damn right. I’ve said it before—swipe files are training wheels, not printing presses.

Look, we all start by copying the greats. But the greats didn’t become legends by copying each other. They absorbed principles. They refined tone. They played jazz with proven chords.

The difference between theft and alchemy is this: one regurgitates, the other transforms.”

Jason: “So when does transformation actually happen?”

Vonnegut clears his throat gently, his voice as poetic as it is practical.

Vonnegut: “When you understand the why behind the words.

You can borrow my metaphors, my humor, my cadence—but unless you understand the worldview that birthed them, you’re just a parrot with a pen.

True alchemy is empathy. You step into another writer’s shoes, not to wear them, but to walk a mile in their mind. Then you come back changed.”

Jason: “And yet, some would say that marketing should be formulaic. That creativity might hurt clarity.”

Gary: “Clarity doesn’t mean soulless. I’ll take a raw, imperfect voice over sterile perfection any day. Hell, some of my best-selling letters had spelling mistakes. Why? Because they sounded human.

I’d rather swipe a style than a sentence. Style is eternal. Sentences expire.”

Bukowski:

“You wanna sell something? Good.

But don’t just dress your pitch in my jacket and think that’s style. My style was born in dive bars, on napkins soaked in gin and blood. You want that edge? Earn it. Live it.

Otherwise, stop name-dropping and start truth-dropping.”

Jason laughs, then asks:

“So is it fair to say all great writing is inspired by what came before, but the best of it leaves fingerprints?”

Vonnegut:

“That’s lovely. Yes.

And remember: readers don’t care if you’re original—they care if you’re relevant. If what you write helps them feel, think, or act differently, then you’ve succeeded—even if your words echo someone else’s rhythm.”

Gary:

“And besides, every great copywriter is a literary thief. But the smart ones steal structure, not soul. They steal emotion, not words.”

Jason: “So how do you practice this kind of ethical theft?”

Bukowski:

“You read until their voice rattles in your bones. Then you write until it’s replaced by your own.

The process is imitation, then rebellion.”

Vonnegut:

“You read widely. Not just copywriting books, but novels. Biographies. Comics. Science journals. You mix the unexpected. You blend poetry with persuasion. That’s where alchemy lives—in the margins.”

Gary:

“You don’t look for lines to copy—you look for truths to translate.”

Jason wraps it up:

“So here’s the distillation:

• Bukowski says: If you steal, make it bleed. Don’t just copy—live what you borrow.

• Vonnegut says: Step inside the author’s shoes to learn, then write from the new landscape of your mind.

• Gary says: Templates train. But transformation—that’s the sale.

Final takeaways?”

Gary: “Swipe to understand. Not to avoid the work.”

Bukowski: “Don’t fake what you haven’t felt. Or the page will spit you out.”

Vonnegut: “Be a librarian of inspiration, not a pirate. The world already has enough of those.”

Jason smiles, closing:
“Every word we write carries a fingerprint. If we borrow, let it be with reverence, transformation, and purpose. Because true copywriting isn’t theft—it’s translation. From the soul of one to the heart of another.”

Beyond the Swipe File – How to Absorb Cadence, Worldview, and Soul

Moderator: Jason Fladlien
Guests: Gary Halbert, Charles Bukowski, Kurt Vonnegut

Jason Fladlien begins with a quiet but pointed question.
“We’ve all talked about swipe files, templates, and formulas. They’re useful—but they’re not enough. Today, I want to ask: How do you go beyond the swipe file? How do you absorb not just someone’s words, but their rhythm, their worldview, their soul—and still write something entirely your own?”

Gary Halbert doesn’t hesitate.

Gary: “Listen, I built one of the most famous swipe files in history. But if that’s all you use, you’re stuck sounding like 1994 forever.

Great copy isn’t about copying—it’s about tuning in. You’ve got to tune in to how a person sees the world. How they speak when they’re not being clever. That’s where the music is.

You want to write like Halbert? Don’t just read me—study what I saw. Understand what I cared about. That’s how you write something that punches.”

Jason: “So how do you tune into someone’s worldview?”

Gary:

“Start by asking this: What was this writer afraid of? What pissed them off? What made them come alive?

Don’t just copy their email. Copy their heartbeat.”

Charles Bukowski lights an imaginary cigarette and leans back.

Bukowski: “You don’t learn cadence from a line. You learn it from living with a writer.

You want to write like me? Then sit with me when I’m broke. When I’m drunk. When I’m writing something I’ll burn tomorrow.

My rhythm wasn’t taught. It was bled out. So don’t mimic the beat. Find your own by walking in my hell for a while.”

Jason: “So you’re saying imitation without immersion is hollow?”

Bukowski: “Exactly. Otherwise, you’re a puppet.

But if you soak in a writer long enough, something shifts. You don’t copy their style—you get infected by their honesty.”

Kurt Vonnegut enters softly, his tone like warm light in a quiet room.

Vonnegut: “Cadence is the signature of the soul.

It’s not just how you write—it’s how you think. How you pause. How you care.

If you want to absorb a worldview, you must read slowly. Reverently. Not just what they say, but what they leave unsaid.

You’ll find their soul in the spaces between their words.”

Jason: “But in the world of marketing, where time is short and content is king—how do you balance that depth with speed?”

Gary:

“Practice. You spend enough time absorbing real voices, you’ll be able to write with one of your own on demand.

I could crank out a killer sales letter in a night—but only because I spent years studying humanity, not just headlines.

Once you internalize rhythm and emotion, you stop thinking and start channeling. That’s the secret.”

Jason: “And how do you know when you’ve found your voice?”

Bukowski:

“When it pisses someone off.

Or makes someone cry.

Or gets a drunk man to sit up and listen.

That’s when you know you’re not pretending anymore.”

Vonnegut:

“When a stranger tells you, ‘I felt like you were writing just to me.’ That’s when your voice has arrived. Not when it’s loud. But when it’s true.”

Jason nods, then leans in.

“So here’s what I’m hearing:

• Gary says: Don’t just read copy—feel what drives it. Study emotion, not execution.

• Bukowski says: Live in a writer’s world before borrowing their words. Cadence is a wound, not a technique.

• Vonnegut says: To absorb a writer’s soul, honor their silences, not just their sentences.

Final thoughts?”

Gary: “Swipe files are the map. But if you want treasure, you have to walk the land.”

Bukowski: “Read the dead. Drink with their ghosts. Then write like hell with your own blood.”

Vonnegut: “Be gentle with the craft. The more humanity you bring to it, the more the world will listen.”

Jason closes, his voice steady and clear.
“If you want to write copy that doesn’t just sell—but echoes—you must stop chasing formulas and start chasing truth. Let the greats teach you. But let you speak.”

Final Thoughts by Jason Fladlien

If there’s one thing I’ve learned from Gary Halbert, Charles Bukowski, and Kurt Vonnegut, it’s that great writing doesn’t come from trying to be perfect. It comes from being real.

We talked structure. We talked suffering. We talked humanity. And the deeper we went, the clearer it became: templates may get you started, but voice is what makes people stay. That’s why I blend Gary’s persuasive spine, Bukowski’s gut-punch honesty, and Vonnegut’s disarming wisdom into every piece I write.

You don’t find that in a swipe file. You find it by living. By listening. By writing like the sale doesn’t matter as much as the moment of connection.

So write something only you could write. That’s the real magic. That’s what sells. And more importantly… that’s what lasts.

Short Bios:

Jason Fladlien – Conversion Strategist & Master Moderator

Known as one of the most effective marketers in the world, Jason Fladlien combines psychology, strategy, and sales mastery. Often called the “$100 Million Webinar Man,” he’s obsessed with unlocking the deeper layers of what makes people buy—and how to make sure it’s built on connection, not just conversion.

Gary Halbert – The Godfather of Direct Response Copywriting

A legendary figure in marketing history, Gary Halbert was known for his razor-sharp sales letters and no-fluff advice. His Gary Halbert Letter remains a goldmine for anyone wanting to learn how to write persuasively, with clarity, speed, and uncanny emotional insight.

Charles Bukowski – Poet of Grit and Raw Honesty

An underground literary icon, Bukowski wrote about the human condition in its rawest form—loneliness, labor, love, and madness. His voice stripped writing of pretense, reminding us that sometimes the most compelling message is the one that hurts a little to tell.

Kurt Vonnegut – Satirist, Humanist, and Storytelling Craftsman

Best known for Slaughterhouse-Five and his sharp, humorous prose, Vonnegut used storytelling to explore chaos, morality, and the absurdity of modern life. He taught writers to blend truth with tenderness and to respect the reader’s time with every sentence.