4 comedy secrets that'll improve your messaging

What do stand-up comedy and messaging have in common? 

More than you might think! Both are about creating connections, making things memorable, and getting a reaction from your audience. 

While I might not be quitting my day job as a Director of Product Marketing anytime soon, I’ve spent 17 years doing improv, hitting open mics, and performing stand-up for fun. I’ve also been in a Netflix comedy special – admittedly, I was in the audience, but it still counts for something!

In this article, I want to share four key principles from stand-up comedy that can help elevate your messaging. Whether you’re pitching to your boss, crafting a campaign, or just trying to get your point across, these principles can make all the difference.

Let’s dive in.

Essential #1: Structure is critical

We already know that how we say something matters. That’s just as true in comedy as it is in messaging.

Let’s start simple. Think about a kid you know that’s around five to seven years old. It could be your daughter, your nephew, your godchild. Ever heard them tell a knock-knock joke? I’m guessing yes. 

Even if the joke makes no sense or the punchline falls flat, they get the structure. They understand there’s a setup and a payoff. That’s because we’re pattern-seeking machines. We love patterns, and that structure is the foundation of any good joke. It’s also the foundation of great messaging.

Take this Mitch Hedberg joke:

“I used to do drugs. I still do, but I used to, too.”

It's simple, but genius. The first line sets a premise. You, as the audience, immediately make an assumption: “Oh, he doesn’t do drugs anymore.” Then the punchline comes in and flips the framing – “I still do.” It surprises you. That’s the payoff.

Now, let’s look at a longer form of the same principle. John Mulaney tells this story about his lawyer parents. Here’s the short version:

“My parents are both lawyers, they are BOTH lawyers, and sometimes they would be like lawyers with us when we were kids. I remember one time I was in bed, and my dad came in and he said, ‘Goodnight, John! Did you brush your teeth?’ and I said ‘Yes,’ but here’s the thing – I hadn’t.

“He says, ‘John is this your toothbrush?’ and I said ‘Yes,’ and he said, ‘So we agree that this is your toothbrush? John, this toothbrush is bone dry. You lied to me!’

“I did not lie. I said that I brushed my teeth; I never specified that I brushed my teeth tonight! And if the court reporter reads back my remarks, you will see that I did not perjure myself.” 

It’s courtroom logic as comedy – and it works because the story builds tension, has structure, and ends with a satisfying resolution.

How to structure your messaging like a joke

You apply this structure to your marketing. Here’s a line I wrote for some web copy:

Double your campaigns, not your workload. Stop guessing which campaigns to prioritize.

That’s the setup. You’re likely already filling in the blanks. Then comes the payoff:

Build twice the campaigns in half the time – freeing you to focus on building the personalized experiences your customers demand.

It’s not a joke, obviously, but it follows the same rhythm. Set the premise, then deliver the value.

Hot tip: Swap “and then” for “so then”

You know those people who tell stories that just ramble on forever? “I went to the airport, and then I went through security, and then I got to the gate, and then I had to pee, and then…” There’s no movement. Just a list of events.

Now contrast that with “I went to the airport, and they opened my bag – so then I knew I was in trouble.”

See the difference? “So then” moves the story forward. It creates momentum, not just a string of facts.

Trey Parker and Matt Stone, the creators of South Park, swear by this rule. They crank out a brand-new episode in just seven days – written, animated, delivered. Every single week. It’s timely, funny, and sharp because they refuse to sit on a traditional nine-month production cycle. Why? Because by the time it’s out, it wouldn’t be relevant anymore.

So, how do they structure their stories? With this golden rule:

Something happens – and something else, but there’s a conflict. Therefore, here’s the outcome.

That structure gives every episode – and every message – shape and momentum. It creates tension, introduces stakes, and delivers a resolution.

And that’s the key. Messaging shouldn’t try to solve everything in one paragraph. I’ve done that before – written messaging that tried to solve the entire world in the first line. Guess what? It sucked.

Your job is to move the reader forward, one beat at a time. Once you’ve done that, then you’ve earned the right to say more.

Essential #2: Kill your darlings

We all have ideas, lines, or jokes that we’re attached to. It could be a line we’ve spent hours crafting or a concept we’re convinced will work. But just because we love something doesn’t mean it will land with the audience. The challenge often comes from our ego or that inner voice (or our boss’s voice) telling us to stick with it, even when we know it’s not working.

The "kill your darlings" rule in writing tells us that sometimes the things we’re most attached to need to be cut. It’s not easy, but letting go of what doesn’t serve the message often results in something stronger and more impactful. In the end, it’s about putting the audience first, not holding onto ideas out of pride or attachment.

Less is more: The art of simplifying

If your messaging isn’t landing, step back and look at it. Are there words in there that don’t really add to the meaning? 

We all know the culprits: “revolutionary,” “game-changing,” and the like. If you scroll through LinkedIn for long enough, you’ll see them everywhere. These words clutter the message, make it harder to go from point A to point B, and diminish your credibility.

Let me give you an example from the world of comedy. Jerry Seinfeld spent two years perfecting a pop-tart joke, and here’s how it started:

"It was the 1960s, and I was a little kid watching television commercials."

That was the first draft. He eventually rewrote it to:

“I was seven watching TV.”

By trimming the unnecessary details – like the year – Seinfeld made the joke shorter and sharper. You don’t need to know it was the 1960s to understand the context. And “I was seven” (rather than “I was a little kid”) gives you a clearer mental picture.

It’s a perfect example of how cutting unnecessary words can improve your messaging. You don’t have to explain everything upfront. Sometimes, less is more.

I ran into the wordiness problem with a headline I was working on. Here’s the original draft:

Transform your business objectives into high-performing segments, letting marketers focus on strategy while our agents handle the data science.

That was a mouthful, right? The second draft?

Build better audiences.

The second line is the real point. It’s all I need to convey upfront. The first version tries to do too much at once, while the second version gets to the heart of the message. I don’t need to explain everything right away; I just need to make them want to keep reading.

Essential #3: Specificity is originality

In comedy and messaging, specificity is key. The more specific you are, the more original your message becomes. Think about what you – as an individual or as an organization – are most qualified to speak about. The more specific you get, the more you’ll resonate with your audience.

When we’re telling stories, especially in marketing, we tend to go too broad. Here’s an equation to keep in mind:

In other words, “I” and “you” statements work better than “us” statements, and way better than broad, organizational-type “they” statements. Why? Because we’re selfish beings, and we relate better when we see ourselves in the story.

Take a look at these examples:

"Your data, your AI, your future." – Databricks

This is a solid start. The repetition of “your” makes it feel personal, but “your AI” still feels somewhat broad. It suggests empowerment, but doesn’t specify what action or outcome the audience can expect. It’s a good message, but it could use a bit more detail to make it feel more tangible and personal.

"Europe builds AI infrastructure with NVIDIA." – Nvidia

Here, the message is more about the region than the individual. If I’m in Europe, I might connect with it, but I still wonder what this means for me. It’s a “they” statement that doesn’t immediately draw me in as an individual. 

"AI for the rest of us. 

"Built into your iPhone, iPad, Mac, and Apple Vision Pro to help you write, express yourself, and get things done effortlessly." – Apple

Apple hits the mark here. The phrase “AI for the rest of us” speaks to accessibility, and the specifics – iPhone, iPad, Mac, and Apple Vision Pro – give a clear picture of how the technology fits into the user's daily life. It’s personal, tangible, and specific, which makes it more engaging.

Of these three examples, Apple stands out. By making the message feel accessible with “for the rest of us” and tying it directly to personal devices, it balances both broad appeal and specific relevance. This is the type of messaging that resonates – it’s both specific and original.

Making it personal

Now, let’s look at how this plays out in comedy. Everyone’s been to the airport and gone through security, right? That’s what we call a “relatable truth.” We’ve all been there, so when comics tell a story about it, we can see ourselves in the situation.

For example, here are three different comics talking about airports:

George Carlin focuses on the absurdity of airline language, Brian Regan talks about lost luggage, and John Mulaney touches on airline anxiety.

Even though these comics are talking about a similar experience – air travel – they each give a unique perspective. The humor lands because it’s personal to them, and we can see ourselves in their stories.

John Mulaney, in particular, isn't just talking about the mundane reality of flying. His joke is, at its core, about anxiety. The setting – the airport – is just the backdrop for his experience of nervousness. He frames his experience in a way that we can relate to, which is what makes it so effective.

That’s the magic of humor – it makes a personal experience feel universal.

Essential #4: Work it out

Messaging doesn’t happen in a vacuum – it can’t happen in a Zoom chat, or on Slack, or in the comfort of your own office. Messaging needs to be tested in the real world, just like stand-up comedy.

Let’s take a page from Mike Birbiglia’s book. He’s a brilliant storytelling comic, and his approach to comedy is something we can all learn from. He has a podcast dedicated entirely to working out comedy bits before they’re ready for the stage. 

His most recent special is a result of two years of writing, touring, and perfecting. After all that work, he took it to the Beacon Theater in New York for filming. That’s a serious commitment to refining your material before going public.

And take Steve Martin and Martin Short – even these comedy legends don’t rest on their laurels. I saw them testing new material at the Comedy Cellar in New York before using it for the SNL 50th anniversary special. 

It’s not uncommon for top comics to hit small venues like this to work out their bits. I even saw Trevor Noah pop in just two days after returning from a Costa Rica vacation. That’s dedication.

Test your messaging in the real world

Now, let’s apply the comic’s mindset to messaging. Messaging doesn’t get perfected in internal meetings; it’s perfected when you test it in front of an audience. That’s the only way to see if it truly resonates.

Your boss may love your messaging, but unless they’re your target customer, that doesn’t matter. We might think we know our customers inside and out because we’ve been in the industry for so long, but until you test your messaging with them, you won’t know if it resonates,

If we were as diligent as comics are, getting out there to test our messaging, we wouldn’t find ourselves using overused buzzwords like “game-changing.” We’d know better. 

(Honestly, I think the term “game-changing” is one of those words marketers cling to because we were the last ones picked in gym class – it’s our way of making up our own rules to feel better. But I digress.)

The point is: test your messaging in the real world. Be willing to adjust and accept that some words or phrases just don’t land. Even if you're attached to an idea, it might not be the right fit. Don’t be afraid to cut what’s not working.

Bonus secrets to take your messaging further

We’ve covered the four essentials, but before we wrap up, I want to leave you with a few bonus secrets for crafting effective messaging.

Tip #1: Explore a new world

Stop reading your competitors’ websites. Not forever, but take a break and go find a completely different industry. Learn how they talk about their products, what matters to them. 

And don’t just look at something tangential to your industry. For example, if you're in martech, don’t go check out marketing automation. Instead, go learn about something completely different, like healthcare or Labubu dolls. 

Step outside your comfort zone. Explore new industries. It’ll broaden your perspective and ultimately strengthen your messaging.

Tip #2: Stay curious

Curiosity is key. It’s not just about writing what interests you, but also observing others – seeing how they’ve mastered something. 

One person who embodied this was Anthony Bourdain. If you watched him interact with people in a small sandwich shop halfway across the world, you’d see an intense curiosity. Despite being a rock star chef, he never stopped learning. He didn’t let his fame or expertise get in the way of constantly seeking new knowledge.

That kind of curiosity is essential for marketers, too. Stay curious and keep notes on everything – whether it's about your own work or about something you’ve observed in others.

Tip #3: Try these writing prompts

Let me share some fun prompts to get your creative juices flowing. These will push you to think differently about your messaging and force you out of your comfort zone.

I especially love Prompt 3 because it forces you to think outside the box. Take something simple, like “we keep your data secure” – it’s boring, right? Now, rewrite it into something absurd but still emotionally true. How about, "We keep your data secure so you don’t end up in a Ukrainian prison." It’s preposterous, but memorable.

Prompt 5 is another fun one. Think about what Geico did with their caveman campaign. The concept was simple – “so easy a caveman could do it” – but the caveman became a character, and that character was used in multiple scenarios to drive home the point.

You don’t have to make your character a literal caveman, but the principle still stands. Think about how you can create a phrase, character, or concept for your company that’s fun, memorable, and can be used in different ways across your messaging.

Tip #4: Get personal with your messaging

Now, let's take it up a notch – we need to get super personal. The best messaging comes from those personal moments. 

During a talk I gave at the Product Marketing Summit in Chicago, I mentioned being an introvert and how, though I love being on stage, after it’s over, I’m going to my hotel room, scrolling through TikTok, and eating some chocolate. I have ADHD, and it’s my way of resetting my serotonin and dopamine levels. 

It was a throwaway comment, but guess what happened? Everybody who connected with me on LinkedIn mentioned it. The next time I met the people who’d been at that talk, they all said something like, “Hope you brought your chocolate!” That little personal touch was what stuck with people the most.

Now, as an organization, it’s harder to be that personal, but you can still find ways to get a bit personal. For example, maybe you’re having a one-on-one conversation with a client – he’s how you can add a personal touch while still tying it to your messaging:

“My company does this. We help you do this. I’ve been in that boat myself. Let me tell you a story about that…”

When you do this, your messaging stops being just about what you want to say. It becomes about what your customers need to hear. And that’s where the magic happens.

Tip #5: Messaging is about what your audience needs to hear

That brings us nicely to my fifth bonus tip. If you remember nothing else from this article, remember this: 

Messaging is not about what you need to say. It’s about what your audience wants to hear.

It’s like a comedian in a dingy club. They’re not up there talking about what’s important to them for their benefit. They’re up there to entertain the audience.

Take Nikki Glaser, a comic whose partner is a TV producer. He was once asked about her making fun of him on stage, and he said something that stuck with me: as long as the joke is funny, anything in their life is fair game. However, if she were up there using the audience as a sounding board for her frustrations, that would be crossing the line.

What he’s really saying is that as long as the comedy connects with the audience, it’s fair. If it’s just self-indulgent or for her own benefit, it’s not.

This is a perfect way to look at your messaging. If what you’re saying connects with your audience, that’s what matters. That’s what makes it work. But if you’re just ranting, if you’re putting something out there just because your sales team thinks it’s the next big thing, like, “We’re AI-powered!” Maybe not. Be sure your messaging actually serves your audience.

Tip #6: Cut through the fluff with Drunk Claude

Speaking of AI and cutting through the fluff, here’s my favorite AI prompt to get straight to the truth. I call it Drunk Claude. It’s a fun way to use AI to get brutally honest feedback on your messaging.

I use this for copywriting, idea generation, and just general brainstorming. It’s amazing because one of two things will happen:

1. You’ll have a good laugh.
2. You’ll see where your messaging needs some work before you take it back to your team.

It’s an easy way to cut through the fluff and get real, raw feedback. I recommend using Claude for this – it’s the best at this kind of unfiltered honesty. ChatGPT 4.5 does a pretty good job, too. If you’re using ChatGPT o3, just know that it might freak out at the “drunk” part. 

Key takeaways

I hope you’ve had as much fun as I did exploring how stand-up comedy can shape your messaging. Here’s a quick recap of the essentials to keep in mind:

• Structure is key: Your message needs a clear beginning, middle, and end to keep it impactful.
• Cut the fluff: If it doesn’t serve your point, let it go. Less is often more.
• Get specific: Speak directly to your audience with clear, relatable examples.
• Test your messaging: See how your audience reacts before settling on your final version.
• Be personal: Authenticity comes through when you share your own stories and experiences.
• Stay creative: Keep using prompts and testing new ideas to find fresh ways to communicate.

This article is based on Zack Wenthe’s brilliant talk at the Seattle Product Marketing Summit.

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