How to Use Incongruity to Keep Your Customers Interested

Incongruity-Resolution Theory

HELLO! Boy howdy, your face is fantastic.

Today we’re gonna be talking more about how that big ol’ brain of yours processes humor.

(This is Part 2 in an extremely slow-going but worth-the-wait series entitled Why Your Brand’s Gotta Be Funny. Read Part 1 here.)

Specifically: today we’ll look at how the brain processes “incongruity,” and what a teensy moment of disconnect has to do with making you snort-laugh.

This is my all-time favorite “Wait, what??” GIF. You will see it in all of my slide decks.

First: What’s incongruity?

Incongruity is a mismatch between what we see or understand to be true and what we (consciously or unconsciously) expected.

We realize that something doesn’t match up. We struggle to understand why. And then we experience a sudden, shocking shift in perspective as our brains adjust to the new reality.

That’s the moment where funny happens — where we “solve the problem” and “get the joke”.

There are a few different incongruity theories and approaches (the rabbit hole goes pretty deep) and at least a dozen full books! To get into all of the various theories here would require me to be a heartless supercomputer, which *beep boop* I am definitely not.

For now, let’s focus on incongruity-resolution.

These theories suggest that humor arises as a result of that problem-solving process. So how does the problem-solving process actually work?

I love this Incongruity-Resolution Model by Jerry Suls (1972), adapted by Rod A. Martin:

Jerry Suls Incongruity-Resolution Model, adapted by Martin

As you can see, our brains predict the outcome of a story or setup.

If we’re right, we’re not surprised, and we don’t laugh.

If our predictions are wrong, we’re surprised. We examine the story or setup for a “rule” that would allow the incongruity to make sense.

If we don’t find that rule, we’re confused. But when we do find the rule, we “get” the joke and laugh!

This double-entendre one-liner is a great example of having to think for a second to find the “rule” or interpretation that makes the joke funny:

“Remains to be seen if glass coffins become popular.”

(where I found this)


Imagine taking a sip of a delicious, creamy red smoothie.

Your mouth and brain are expecting strawberry. So it’s pretty jarring when your tongue registers “OH SHIT, THIS IS KETCHUP.”

Womp womp.

Now, that experience might not be ha-ha funny (at least not to you, or not at the time) but it’s a perfect illustration of how it feels to expect one thing and get something different.

Tons of standup comedy is built on laying expectations, and then flipping or changing the joke’s resolution to something the audience doesn’t expect.

For example, consider this joke from Emo Phillips:

“I learned about sex the hard way — from books!”

One of my favorite, most meta examples of incongruity-resolution is from the brilliant Dan Gilbert. While explaining the brain’s tendency to always be “nexting” (predicting the future), Gilbert tosses out this perfect sentence:

“As long as your brain’s guess about the next word turns out to be right, you cruise along happily, left to right, left to right, turning black squiggles into ideas, scenes, characters, and concepts, blissfully unaware that your nexting brain is predicting the future of the sentence at a fantastic rate. It is only when your brain predicts badly that you suddenly feel avocado.”

Reader, I cackled.

Incongruity by itself isn’t necessarily funny

It’s important to remember that while incongruity is a vital ingredient of humor most of the time, incongruity by itself isn’t automatically funny.

If you were walking on the sidewalk and you got hit by a car, that’d be incongruous. But I bet you wouldn’t think it was funny! This example borrowed from Rod A. Martin’s The Psychology of Humor, a textbook with which I am straight obsessed.

Why did the monkey fall from the tree? Because it was dead.

(where I found this)

Where to use incongruity in your marketing

Like other approaches to humor, incongruity can fit neatly into lots of different spots in your marketing strategy.

But one place it’s super-effective? The top of the funnel, where you need to snag attention FAST.

Spot #1: Use incongruity at the top of your funnel to get attention

PPC ads, videos, and email opt-in popups are all fair game for grabbing someone’s attention, making them say “Wait, what?” and then flipping the script on them.

Here’s an opt-in I screenshotted from Paris fashion designer (and Punchline subscriber!) Striiiipes. This opt-in is hidden behind a tiny footer link that says “Don’t click here”:

via Striiipes

This introduces incongruity. Why wouldn’t you want me to click around your site??

When you do click that little link, you’re treated to the resolution:

via striiipes


One of my favorite parts of my own top-of-funnel setup is a lil ol’ page on called “Secret Cat”.

Users click a link in one of my first few onboarding emails to tell me more about themselves — and as a reward, they’re whisked straight to a page featuring a photo of my ridiculous cat lying upside-down.

sg upside down

This is not the same photo. He’s just usually upside-down.

Presumably, Secret Cat is not what my readers were expecting. But the experience of “finding” him is generally beloved.

(Or so I assume. 😬 Hey, people stay on the list.)

Viral video ads tend to use an incongruous or unbelievable setup as a hook to keep viewers watching, and then flip the script on their expectation.

Harmon Brothers is especially great at this. Just watch the opening of this Poo-Pourri spot, which they made:

You see a perfectly groomed, fancily dressed, beautiful woman (with a British accent — which is automatically more authoritative to American ears). Then you hear her declare, “You would not believe the motherlode I just dropped.”

That prooooobably wasn’t what you were expecting.

And you probably snickered a little bit. Boom: incongruity accomplished. You’ll keep watching. (This is just one of tons of successful, viral ads Harmon Brothers has created along the same lines.)

I’d include an example of a PPC ad that uses incongruity, but I haven’t seen one because PPC ad copy is UNIVERSALLY SO FUCKING BORING.

Spot #2: Use incongruity throughout retention, too

The better you get to know your customers, and the better they get to know you, the more opportunities you’ll have to surprise them.

Also, getting to know your people is just good marketing practice. You make more relevant offers, they feel like you’re actually helpful, everybody wins!

/gingerly steps off soapbox to avoid spraining my ankle… again

One place to avoid incongruity? Pricing & transactions

While incongruity-based humor can be totally innocuous, you still don’t want to introduce potential confusion or distraction anywhere you need a reader to trust you.

Also, and hopefully this doesn’t really need to be said, but don’t intentionally set your readers up with an expectation and then disappoint them.

E.g. if you send an email that says something like, “What’s hot, starts with the letter S, and ends with the letters A-L-E?” Your readers will expect a sale.

So for the love of Blob, don’t then link them to a picture of bread with the caption “StALE TOAST!”

oh god

^^^ This was the worst example I’ve ever written. But you get it.

Be aware when your audience’s predictions become expectations, and try to exceed those expectations.

What are your favorite incongruity-resolution jokes or marketing moments? Hit me with ‘em in the comments!

“What does laughter mean? The greatest of thinkers, from Aristotle downwards, have tackled this little problem which has a knack of baffling every effort, of slipping away and escaping only to bob up again, a pert challenge flung at philosophical speculation.”

 – Henri Bergson, 1911

How to Write Funnier Copy with the Rule of 3

How to Write Funnier Copy with the Rule of 3

The Rule of 3 (also called the “triple”) is a copywriting and comedy commandment.

Think about it.

Everything is just punchier, more memorable, and more enticing in threes — whether you’re creating a bullet-point list, ordering scoops at the ice cream shop, or juggling multiple lovers… none of whom know about the others’ existence. 😬

mesmerizing, isn't it?

This GIF is only tangentially related to that last thing, but honestly, how could I not use it

Schoolhouse Rock even did a song about the rule of 3, which is, like, Jesus, so incredibly creepy:

(Scroll down for an even creepier video on the rule of three. Oh my god, who rubber-stamps this stuff??)

So why does the rule of 3 have such power over us?

Psychological secrets behind the rule of 3

Secret #1: We like things with a beginning, middle, and end

Recently, I saw a newbie try his hand at a local standup comedy open mic.

He grabbed the microphone and started telling a story about his roommate walking in on him while he was masturbating.

Aaaand… that was the end of the story.

Highly dissatisfying. (Probably for everyone involved.)


Actual video of the audience reaction

Why? Because this turdburger didn’t tell a story with a beginning, middle, and end! He left off the end and expected the audience to laugh anyway.

But no one was ready to laugh, because we were still waiting for the story to end (and for this dude to get offstage).

There’s a reason that plays often have three acts… a reason that the trilogy is a popular book and film format…

And that shitty, three-word, period-punctuated headlines like “Cutting-Edge. Superior. Amazing” still appear all over the Internet.

Also in the real world:

Hat tip to Digiday

Secret #2: Three is the minimum number required to create a pattern or “streak”

Remember 10th grade geometry, when your teacher pointed out that it takes a minimum of two points to create a line?

Well, it takes a minimum of three things to create a discernible pattern. That’s why, given a brain-teaser like “Find the 4th number in the sequence: 3, 6, 9, ___,” we can figure out the next number.

Having just “3, 6” wouldn’t tell us what to do next.

Interestingly, one study found that “the third repeat event in a sequence is pivotal to the subjective belief that a streak is occurring.”

Put another way, you need to see your boyfriend do the dishes at least three times before you believe he might actually be worth keeping around.


Lol, gender roles, amirite

Secret #3 (ooooh!): A series of 3 offers a concrete “middle” choice

We also like things in threes because offering three items can help anchor the “middle” choice as the best or most popular. This is a useful pricing tactic, and one you’ll see all over SaaS and other service-provider websites.

Secret #4: Three has a naturally satisfying cadence

Listen to any NPR broadcaster read a series of three items. Their voice will lift or lower on the second one.

It’s just a natural inclination to indicate the difference between one, two, and three.

How to use the rule of 3 in funny copy

In general, if you’re writing copy with a series of three, save the funny word or phrase for the last item in the series. That ensures it’ll have the maximum punch.

What’s funny?

Usually it’s something surprising or shocking. Or something that’s the opposite of what you were led to expect (this is called a reversal).

“I celebrated Thanksgiving in an old-fashioned way. I invited everyone in my neighborhood to my house, we had an enormous feast, and then I killed them and took their land.”

– Jon Stewart

You can also “heighten” throughout a series.

I could do an entire post on heightening (and I probably will… soon).


My next blog is just over that ice floe

But for now, think of heightening as moving in a clear direction. You can start small and make something bigger and more bombastic, or the opposite — start “normally” and get ridiculously small or insignificant.

You might go from “safety pin” to “knife” to “harpoon cannon”.

Or you might go the opposite direction, from “President of the Galactic Republic” to “2-term Congressperson” to “night janitor at the local high school”.

It’s the relationship between these items that’s funny, not any single item on its own (though I did titter a little when I came up with “harpoon cannon” just now, ‘cause it sounds good. More on funny words and sounds later… ).

I like how improviser Will Hines defines heightening as “hit[ting] a comedic idea several times in a way that obviously gets more absurd as you go.”

(Side note: buy Will’s book, How to Be the Greatest Improviser on Earth. It rules.)

Where should you use the rule of 3?

Aim to lighten the mood with humor in any of these spots in your copy:

Series of examples  — Item 1, Item 2, Unexpected/Absurd Item 3


ComparisonsWriting this post is like having my teeth pulled, only I’m both the dentist and the victim.


Exaggerations This chair is so old, it probably has grandchildren. It probably uses an AARP discount card. It’s so old, it needs its own goddamn chair to sit down and take a load off.

In intros or lead-ins You know, like I did with this post


Remember that 3 is the minimum number required to form a pattern. You don’t have to stop at three.

If you want to hammer home the humor and venture into absurdity, you can continue adding to the pattern, like SNL does in this sketch:

The basketball players in the background are what’s funny in this sketch. They get called out by the director three times, and then we see a series of quick cuts where the background players get more and more ridiculous.

(And did you notice the reversal at the end of the sketch?)

Quick caveat here: if you add more to your series of three items, make sure you don’t let your joke outstay its welcome.

PS. The world’s creepiest video on the rule of 3

Told you I’d give it to you.

How do you usually use the Rule of 3?

Take It From the Experts: HBO’s “Talking Funny”

Takeaways from HBO's Talking Funny

Talking Funny is a 49-minute HBO special featuring Ricky Gervais, Jerry Seinfeld, Chris Rock, and Louis C.K. sitting around and talking about comedy.

They chat about the moments they first felt like real comedians and what they like and dislike about each other’s work.

Also, they do impressions of each other, which rules.

And while I’d have loved to see *literally any* female or nonbinary comic included, the video is absolutely worth a watch for comedy nerds!

NOTE: Yep, Louis C.K. was part of this discussion. This was filmed before we all knew he was/is a big ol’ creep.

SECOND NOTE: There’s a part of the discussion that includes the N-word around minute 16. The discussion moves to curse words in general at minute 17.

So what can you learn from 4 masters of the comedic craft?

Here are my takeaways. Yours might be different, but that’s why this is my blog + not yours

Different comedians build their acts in different ways — While C.K. and Chris Rock both write a new hourlong act every year, Seinfeld tosses 10-20% of his act each year and replaces it with new jokes


Wanna get better? Build on the best material you have — Louis C.K. regularly makes himself use his former closing bit as a new opening bit, “just to fuck myself”


Jerry Seinfeld sure likes to talk over people (though we knew this from Comedians in Cars Getting Coffee)


You can have a great joke, but if you don’t set it up right, it won’t hit because the audience doesn’t understand the premise. Context is everything.


To Ricky Gervais, truly great comedy isn’t about being funny, because some things are always funny (ex. personifying animals). It’s about “going out and doing something no one else can do.”


In that same vein, jokes that depend purely on profanity aren’t good enough


Chris Rock’s take on racist jokes: “Talk about what [people] do, not what they are


Have you watched this special? It’s been on my list forever.

Interested to know what you got from it! Leave a comment and let me know. I promise I’ll actually check the draft comments this time. ????

(Side note: I feel like Seinfeld wakes up in the morning and looks in the mirror and growls, “You’re Jerry Fucking Seinfeld, you glorious bastard.”)

Why Your Brand’s Gotta Be Funny

Why Your Brand's Gotta Be Funny

(Pssst, I’m hoping to turn this into a series of posts about the psychology and functions of humor! Let me know in the comments what other topics you want me to cover.)


Why should businesses use humor in their marketing?

Well… let’s look at what the research says.

it's a stampede!

cue everyone leaving

Psychologist Michael Apter suggests that there are two social contexts, or states, that humans switch between:

The telic, or goal-oriented state — AKA when we’re focused on gettin sh** done

And the paratelic, or play-oriented state — AKA when we’re goofing off and making jokes

We switch between these modes all the time throughout the day. (Just think of the last meeting you went to, when someone cracked a joke. Everybody laughed… and then y’all all went back to work.)

Now, these moments might just seem like quick breaks, but this kind of playtime actually serves some super-important social, emotional, and cognitive functions.

For example, research has shown that humor is linked to overall improvements in outlook and attitude. It’s a coping mechanism when times are tough. And it helps people bond together as a group.

All of this seems pretty self-evident from, um, being a human in the world, right?

But for some reason, the idea of being funny just FLIES OUT of most people’s brains when they’re putting their marketing campaigns together.

Which is crazy, because marketing is all about forming a real connection with your customers. So why would you just leave one of your best tools in your arsenal?

Humor helps you…

 Build genuine relationships with your readers or users — you know, like the relationships you have in real life (if you don’t, well, that’s a different issue)

Address potential objections in a lighthearted way, and paint a realistic picture of what people COULD be doing instead

dealforma screenshot

This benefits copy I wrote for DealForma helps readers better picture their life with clean data

Save face in awkward situations — like when you need to ‘fess up to a mistake, or roll out sensitive new pricing or plan updates

Alleviate anxiety in key moments — for instance, when your user might be worried about whether they need to provide a credit card for a free trial CTA

Fun little click-trigger copy I wrote for (check it out. It rules)

AND a whole lot more.

Now, there’s obviously way more to all of this — in fact, there are multiple books about the psychology and function of humor in the brain.

I’m barely scratching the surface here… but scratching sure does feel good.

happy lil sloth scratching

Live video from the Punchline office.

Wanna learn more about how humor works in the brain, and how you can leverage it to improve your marketing?

I’m building a course! Sign up below to hear when I launch it:

Blue Ribbon Ecommerce Mastermind

blue ribbon ecommerce mastermind denver

Hey you! Look at your face. It’s a great one. I’m glad it’s reading this blog.

Soooo. Earlier this month, I had the wild honor of speaking at the Blue  Ribbon Ecommerce Mastermind in Denver!

What’s Blue Ribbon?

The Blue Ribbon Ecommerce Mastermind, run by Smart Marketer, is a group of the most successful ecommerce business owners in the world, plus a sprinkling of tip-top agency owners and marketers.

And they’re somehow ALL shockingly talented Ping-Pong players. Like, shocking.

I mostly drank and watched.

Blue Ribbon members sell their own original products (like Panda Planner and Groove Rings), cool shit they discovered in China, auto parts, supplements, you name it.

If it’s genuinely valuable to customers, if there’s a niche for it, someone at Blue Ribbon is probably selling it or about to sell it. They’re prescient AF like that.

Ezra Firestone is the marketing genius and ecommerce biz owner behind Blue Ribbon. * insert beardy man-bun emoji *

He kicked off the 2-day meeting with a rundown of the biggest challenges facing online store owners.

Ezra’s kickoff session was followed by talks from luminary geniuses like Brett Curry, Drew Sanocki, Moiz Ali, Todd Kriney, Molly Pittman, and more.

patrick eckstein, william painter

Please enjoy this totally gratuitous photo of me and William Painter co-founder Patrick Eckstein, wearing WP’s killer shades.

Oh, I spoke too!

I was super-honored to share my talk on humor in marketing (which boils down to why, how, and where in your marketing funnel it pays to be funny).

Check out the killer live sketchnotes the Smart Marketer team was kind enough to arrange for all the speakers — and then send to us after the event!

blue ribbon ecommerce mastermind sketchnotes

Featuring two extremely hairy Vanna Whites!

A couple of book recs for the road

Here are the two books I added to my list after speakers recommended them:

Baby Bathwater Island Recap

Baby Bathwater Island Recap

If you follow me on Instagram (which you don’t, because you have better things to do), you might know that I was in Croatia earlier this month.

More specifically, I was on a private island named Obonjan for an event called Baby Bathwater Island.

The best way I can describe this event is “Boozy Entrepreneur Sleepaway Camp”.

It was exactly as awesome as it sounds.

literally MADE for instagramming

The whole place was infinitely ‘grammable.

My fellow attendees? A group of 150 people whose personal and professional accomplishments make me want to crawl into a dark hole and binge Lucky Charms until I puke.

You name it, they were there: hugely successful ecommerce store owners, agency founders, inventors, philosophers, influencers… all the cool titles you get to choose from if you hang out on the Internet these days.

INCREDIBLY, not only did I get to hang out with these goshdang luminaries, I also got to deliver my all-time favorite talk: How to Be Funny (Even If You’re Not): Comedy-Inspired Copywriting Tips.

How to Be Funny: Improv Inspired Copywriting Tips

(Did I eat shit on the gravel pathway down to my talk 3 minutes before delivering it, you ask?

Yes, yes I did. It was less “slapstick” and more “Fuuuuuuuhhhhhh I’m glad no one saw that. Oh look, I’m bleeding”)


Spending 5 days at Baby Bathwater, listening to talks on things like “hedonic engineering” (by Jamie Wheal), microdosing (by Jack Allocca), crowdfunding (by Roy Morejon), and hanging out with some of the most incredible people I’ve ever met gave me a new perspective on work… and life.

I wish there were a non-cheesy way to say that, but there isn’t.

And that’s coming from me, a noted skeptic who figured hey, this event might well be a huge waste of cash.

I left inspired to work harder, give myself permission to be awesome, and focus on doing more of what I love.

So how did the magic happen?

Well, the setting (a breathtaking private island in the middle of the Adriatic Sea) didn’t hurt.

NBD just fuckin paradise u kno

   Oh fucking stop it already, sailboat.

And neither did the included wine and cocktails (which, as a native New Orleanian, really made me feel at home. Also drunk.)

But honestly, because BBW is a “no-pitch” zone, the pressure was off — and that’s where I shine.

Ask me to give you the hard sell on what I do, and I can… but it’s not my favorite conversation to have.

HOWEVER. Sit me next to someone I admire, and let me make food puns and nerd out about the psychology and marketing applications of humor… and I will be there ALL. NIGHT.

Here’s what I took away:

I’m raising my rates. Starting with my day rate, which will be going up by 1K for new clients starting September 1. (Want to snag me at my current rate? Book your day now.)

I want to be around these people more. People who don’t cut themselves off from a new idea because it seems hard or even impossible. People who say “Hey, cool, let’s do that thing,” and then DO IT.

I’m finally making a course. One thing I heard over and over (especially from folks who were too hungover to come to my 10am talk, or who rightly wanted to see my new pal Tom Breeze’s excellent YouTube ads talk at the same time) was: “Do you have a course? I’d buy it!”

Up until this year, I’ve felt that it wasn’t time for me to build a course yet — that there was more for me to learn, and hone, and who was I to be teaching a course anyway?

And yeah, there’s still more for me to learn… but there’s also a LOT that I want to share.

There are people who I can’t work with one-on-one, whether it’s because of money or time constraints or the fact that they’ve been dead for 80 years (shoutout to my dawg, Claude Hopkins).

A course is the best way to share what I love, what I’m just so deeply into and excited about — humor in marketing — with more people who are interested.

So keep your eyes peeled, because it’s coming.

And if I have my way (which I will, cause like, it’s my course)… it’s gonna be fun as hell, y’all.

Sign up to hear when I launch the course:

You've already subscribed to Just The Tips, you sly dog! Why not follow me on Twitter instead?

GDPR Emails: The Good, The Bad + the Come On Now, Y’all

GDPR Email Marketing, Ranked

Oh hey there!

Just in case you’re one of the 12 people who doesn’t have an email address, you may have missed a Big Thing in the world of online marketing recently.

The European Union passed some laws about how businesses can communicate with their customers and subscribers and use their data.

TL;DR: it’s called GDPR, and it made people freak the f*** out about their email lists.

oprah cat freakout

Any excuse to use this GIF, honestly.

(A non-marketer friend of mine, when I told him about this, said: “Is THAT why I’ve been getting all those ‘We updated our privacy policy’ emails?” What a sweet, sweet baby.)

Funnily enough, you might not have even needed to send a compliance email, if your regular list includes an “unsubscribe button”:

Anyhoo, my inbox was just as inundated with panicked GDPR emails as yours was…

But unlike you, I am a BIG OL’ EMAIL NERD.

So today I’m holding an impromptu awards ceremony for the email copywriters at these companies. Some of whom are doing really honestly fabulous work! And others… others who might not exist.

We’ll start with the BAD, move to the GOOD, and end with the “Come On Now, Y’all”. ????

Because who doesn’t love a good old-fashioned ribbing?

(As always, click the images to open the full-size screenshot in a new tab!)


The Bad includes literally every email that looked like this:indiegogo gdpr, gdpr emails, email marketing

HARDCORE SNORE. Sorry, Indiegogo. Not picking on you for any particular reason.

You could play Cliche Bingo with the phrases in these emails.

Mark one X per square every time you see the following phrases:

– “We care about your privacy”
– “Your privacy is important to us”
– “Our commitment to your privacy hasn’t changed”
– “There is no action required on your part”
– “We know you place your trust in us, and we don’t take it lightly”
– Subject line: “We’ve updated our privacy policy” OMG REALLY? YOU AND THE REST OF THE WORLD

Special shoutout to Against Malaria, to whom I donated once and promptly unsubscribed one million years ago. They sent me the same email everyone else got:

against malaria gdpr email


Guys. GUYS. Why did you not segment your list to make sure that you were sending a version to unsubscribers that said something like,

“Hey, you haven’t heard from us in a while, but here’s why.” <– ???!!!

Even some of the other folks in this category managed that.

(OK, sorry for ragging on a nonprofit that probably doesn’t have the resources to know stuff like this. If you want, you can donate to them here.)


This is the part where I give medals, because YES, TERRENCE, EVERYTHING NEEDS TO BE A COMPETITION.


airstory gdpr email

What’s good here:

This was the only GDPR email to use a literary/nonfiction quote, and I’m here for it. Airstory uses Arndt’s words to remind people what their software actually does — helps people write — then segues into the boring stuff.

They acknowledge that people aren’t going to read their policy, and tell them what’ll happen anyway. Loving the honesty.


sumo gdpr email

What’s good here:

“Because we don’t want to bore you, we’re going to make this fun.”

AND they’re giving away a swag bundle! Is that legal? Who cares, they did it. Look at Sumo go.


bidsketch gdpr email

What’s good here:

It’s personal, short, AND includes a CTA that helps Bidsketch make lemonade (new trial users!) from lemons (having to bother people).

Zapier – Bronze Medal

zapier gdpr email

What’s good here:

Instead of taking the Eeyore approach of “We have to do this, bah humbug,” Zapier flips this mandatory email into a boon for subscribers.

They also helpfully remind people of the lists they’re already subscribed to (though mine don’t show, interestingly), and tell them what’ll happen if they don’t click the big orange button.

Fomo – Silver Medal

fomo gdpr email

What’s good here:

This might be the chillest email I have ever seen. Ryan comes across as an animate bottle of CBD oil, he’s so chill.

It’s funny, it’s calm, and it ends on a sweet and upbeat note: “happy selling”. What’s not to love?

Endcrawl – Gold Medal

endcrawl gdpr email

What’s good here:

Who’s NOT going to open an email titled “Please help us stay out of jail”? No one. Except maybe Trump.

But you, dear stranger, are better than he is.

And Endcrawl is better than all of us. Just look at this lively email, with its casual tone, front-and-center bullet-point benefits, funny and varying CTAs, and — just like Bidsketch  — its tantalizing offer, which could turn inactive or clueless subscribers into brand-new users.

Bravo, Endcrawl! U single?

(Hat tip to Alan for bringing this email to my attention!)

Honorable mention goes to Josh Kaufman, whose “New Post + GDPRmageddon” subject line made me smile, and who smoothly rolled a real intriguing lede right into his own policy updates:josh kaufman gdpr email


This category is reserved for businesses from whom I just… expected more.

GDPR emails in this category are basically the same as those in “The Bad,” but I had higher hopes for these companies. And they let me down.

Maybe that’s my fault? … Did I just gaslight myself?


Moo absolutely KNOWS how to write and send funny, piquant emails. I loved this one in particular:

moo email

Image thanks to Really Good Emails. Click through and tap “View the Live Email”. It’s worth it.

So their GDPR email, while friendly and succinct, felt a little flat to me.

There was an opportunity here, and Moo missed it:

moo gdpr email


mailchimp gdpr email

Come on, MailChimp! You were one of the first brands to stand out in the email marketing space.

Why hand over the reins to the legal team and let them send this snoozefest? This makes you look more like MailChump.

What happened to your lovable zaniness? Where is your zest and zip? Wherefore art thy zazz???


appsumo gdpr email

Only the subject line here (“Ch-ch-ch-ch-changes (to our privacy policy)”) and the subheader (“laws are a-changin'”) are good. The rest of it is, well, boring.

And that concludes the GDPR Email Olympics! Conceived, hosted, produced, and attended by… pretty much only me. #lonelyolympics

Was this fun for you to read?

I’ll give you a minute to think about it and add a sweet comment.

In the meantime, here’s some #GDPR easy listening for you:

The Software I Can’t Live Without

BRUH. You ready for me to blow your damn mind?

I say this all the time to people who don’t spend 16 hours a day staring deeply into the butthole of the Internet:

I believe that software can save the world.

And even if it doesn’t, at the very least, it’ll save us all some damn time and hassle.

So here’s a short list of my top favorite software-as-a-service tools.

I’ve left out a few things like my email service provider (ConvertKit, for the record), and my video call software (Zoom), since people tend to be able to pick these things for themselves depending on their needs.

Most of the below recommendations don’t have referral/affiliate links, but a couple do. I’m lazy like that. 😉

I hope this introduces you to at least one killer new tool that saves you time and makes you feel like a total badass!

1. Boomerang for Gmail

I don’t really use a CRM (customer relationship management) platform. That’s because, with Boomerang and Trello combined, I don’t really need one.

For me, Boomerang does 2 things:

  • Keeps me from ever forgetting to follow up on an email, with its “Return to inbox if no one replies” function
  • Transforms “I’m a nutjob who writes emails at 11pm” into “I’m a bright and capable early riser,” with its “Schedule email to send later” function

Sometimes, all I need to stand out from the faceless pack of rabid copywriters is the simple reassurance that I’ll answer emails and stay on the ball. I can’t believe the bar is that low, but sometimes it really is.

Speaking of low bars

How I use it: Following up on project proposals, review deadlines, collaborations, cold emails, you name it.

Anytime I think someone *might* not get back to me, I click a lil checkbox and sit back on my haunches, reassured that I won’t forget to follow up.

—> Looking for something similar but more powerful? Something that can automatically send one-on-one emails in a sequence to multiple people, cue up draft emails for you, and remind you to follow up when no one’s answered? Look no further than

(Full disclosure: I wrote the Bluetick site copy and am speaking at the founder’s conference this month. Fuller disclosure: That doesn’t matter, because the tool is fucking rad.)

2. TextExpander

Telling you about TextExpander is my gift to you for reading this far.

You know all those things you’re constantly having to dig up, copy/paste, or type from scratch? Like…

  • Canned responses to the kinds of emails you get all the time
  • Links to your calendar or video call locations
  • Reminders to send or do something
  • Links to your past content, favorite posts, or products/services
  • Short phrases like “How are you?” or “Thanks so much”

TextExpander takes the tedium of typing or copying/pasting your canned responses or links, and replaces it with a short abbreviation.

FOR EXAMPLE. When I wanted to send someone to my Calendly scheduling link in the past, I’d open a new tab, type “cal” into the omnibox, and wait for my oft-visited Calendly link to come up.

If I’d cleared my cache recently, I’d have to go as far as logging into Calendly to grab the right link.


Now all I have to do is type “x30cal”. Voila: the right link, prefaced by the sentence “Any times that work for you here?” loads automatically.


Relax and enjoy.

(The “x” prefix is so I don’t accidentally TextExpand anything I don’t mean to. You can add any prefixes you want. Plus, TextExpander sends a series of helpful emails showing you how to use the tool to its full potential. Love that about them.)

I’ve got whole canned emails preloaded as “snippets” under short labels.

No more copy/pasting. No more just writing new versions of them every time.

TextExpander works across all of your devices and if you haven’t signed up already, Jesus Christ what are you waiting for?

3. Zapier

I’ll be the first to admit that I’m not using Zapier to its full potential. It’s the glue that holds the whole Internet together, in my eyes.

But still: having the ability to connect basically any tool I want to any other tool I want? AMAZING. WE ARE IN THE FUTURE.

(I know this isn’t exactly news. If you were looking for a hot take, you may want to look elsewhere.)

You, searching for a hotter take

How I use it: To connect Typeform to GoogleDocs, so new client intake forms are automatically in a Call Notes document before I ever get on Zoom. And in my other business, SNAP Copy, we use it to connect WooCommerce to ActiveCampaign so we can auto-send new clients the right emails.

There are many, many cool ways to use Zapier, and I plan to have my brand-new VA set those up for me (I am more excited about finally having a VA than I will ever be about the birth of any baby, even mine).

4. Trello

Another “Duh” moment for a lot of y’all here.

Trello is a “card”-based tool that works for a ton of different use cases. Most folks I know use it as a project tracker, and take advantage of the ability to add labels, due dates, and checklists to cards to keep themselves organized.

My actual Trello “CRM” at the moment

How I use it:

  • As a “light” CRM to track clients, from prospect to proposal to project to post-prandial pinot noir
  • As an actual project tracker to make sure I check off every project’s component parts
  • As an accountability tool to make sure my good buddy Amy Harrison and I get the things done that we said we would


Fun fact about The Zone: it’s impossible to get in if there’s someone near you at the coffee shop chewing like a wild animal.

This is the worst sound in the world.

Or someone yakking on the phone to their girlfriend. Or someone with a baby that just CAN’T GET ITS SHIT TOGETHER.

Or… you get the point.

Now, you could pop your headphones in and listen to music. But what music? And what if the music distracts you even more than the chewing noises?

Enter This handy little player offers three modes of music: Focus, Meditate, and Relax.

The “Focus” mode treats your ears to a thrumming background of music-ish noise that ebbs and flows according to ~*~* science *~*~. Apparently it messes with your brainwaves in some way? I don’t know. I haven’t read the website.

This is what it looks like:

How do I describe the music? It’s kinda trancey, but sometimes there’s piano. Honestly, I don’t know what to call it — because the point is that it works so well you’re not really listening.

Now, anytime I need to enter The Zone, I can pop in my earbuds and get to work, regardless of whether I’m surrounded by noisy chewers, phone talkers, aggravating babies… or some monstrous combination of all 3. That is my nightmare.

Honorable Mentions

Google Apps. All of ‘em.

Google is life. That’s it, y’all. If you’re still using Microsoft Office and exporting files and dealing with “markups,” you’re probably also still driving the same car you had in 1989 and shouting at birds, and I can’t help you.

Yep, Google has all my data. It knows things about me that not even my therapist knows, and I’m cool with that because I have to be.

If you’re not, well, it’s probably time to stop reading this and start building your off-grid survival yurt.

Why I use it: Shareability, free space on my hard drive ‘cause everything’s stored in the cloud, minimal fear of losing everything I’ve been working on… unless Google decides to steal it.


Typeform is a form builder. You probably know of it or already use it.

I use it for my prospect intake forms, customer surveys, and various other formy things. It’s easy to build a pretty-looking form that has a more visually engaging customer experience than other forms. (As an aside, if you’re in search of an insanely informative monsterpost about creating better customer experiences, head to Hotjar to read this piece I contributed to.)

Pro tip: Make your prospects choose between kitties and puppies, and only work with the kitty people

Typeform also presents questions one at a time, helping cut down on information overwhelm that could keep your forms from being completed.

How I use it: The “Logic Jump” functionality (only available for Pro and higher-level accounts) makes it easy for me to weed out prospects who won’t be a fit, and send them to the right place for whatever service they need.

One thing it’s NOT great for? Creating quizzes. You’re better off coughing up the $30/month for Interact or a similar tool. 🙁


Digit is a sneaky little pal that you connect to your checking account. Whenever you spend money, it swipes a little bit more from you and stashes it away in a savings account.

Every now and then, you’ll remember you have a Digit account and discover that all of a sudden, you actually have like $500 more than you thought you did.

Well would you look at that. COLD HARD CASH.

It’s like free money!!!

I mean, it’s still your money, but admit it: you wouldn’t have saved it on your own.

How I use it: Travel piggy bank. Helllooooo, Croatia.

Please please tell me about your favorite tools in the comments! I can never have enough subscriptions.

Steal My Secrets: How I Do “Uppercuts”

How I Do Landing Page Copywriting Uppercuts - Punchline Conversion Copywriting

Hello and welcome back to the latest edition of Steal All My Secrets (I’m Literally Banking on the Fact That You Won’t)!

ohhhh shit

Ohhhhh shit

Today, I’m gonna show you exactly how I perform the black-magic combination of rewriting and editing that I call an Uppercut.

What’s an Uppercut?

Uppercuts are my most popular productized service.

They’re custom-written improvements to existing landing or sales pages that need some love — both on the overall optimization side (think structure, layout, and design) and on the copy side (think tone, messaging, and personality).

They’ve been called “copy wizardry” by happy clients, and “black magic fuckery” by impressed/jealous copywriting peers.

Here’s what my most recent Uppercut client had to say:

Hi L, great job — the more I read it the more I like it! Def got my money’s worth. I really did get a lot of value from this. Specifically, it is a solid balance between humor and professionalism, nice job of cutting the fluff, loved a lot of the rewording as it helped clarity.” 

Steal my process! Here’s how I do Uppercuts

Step 1: Structure

The very very first thing I do when starting an Uppercut is enjoy a 15-minute roll on a bed of crisp 100-dollar bills, cackling to myself.

money is so great

“They paid me! I’m a real boy now!” I crow to my mother, who is confused about how I turned out this way

The next first thing I do is  look at the structure of the page.

I ask:

  • Does the page meet prospects where they are, and speak to their exact stage of awareness?
  • Are the messages on the page in a logical order? Do they mirror the progression of thoughts the reader is likely to have?

If the answer to any of those questions is “Lol nah,” the structure needs fixing.

At this stage, I’m doing quick-and-dirty restructuring — cutting and pasting messages where they need to be, and adding placeholder headlines and subheaders. Like so:

This is so meta

If this is too meta to follow, I am very sorry and I did it on purpose.

HOT TIP: If you’re using both headers and subheaders, you’ve probably accidentally hidden the REAL benefits in the subheader. Try swapping them.

Once I’ve got the basic section structure down, I apply the same process to the body copy.

Because people write how they think — and we frequently forget things and remember them later— there tends to be also be some disorganization and repetition in the body copy.

Like I do with sections, I’ll cut body sentences and paste them where they need to be to improve the logical flow of the copy.

Then, I insert placeholders and/or highlight spots where I know I’ll need more information or transitions between sections. Voila:

You’re getting a sneak peek at a blog I haven’t finished yet! Lucky you.

Sometimes, people overlook structure in favor of focusing just on smaller line edits. That’s a mistake. Restructuring can help you take advantage of HUGE opportunities to clarify your offer.

Here’s what another client had to say after she saw the radical restructuring I did to her page:


Oh my. You slayed right through the copy and it looks so different but still using the copy and adding your tweaks to it. I had to noodle it over for a day. The first day, I was in shock (in a good way). The second day when I read over it I understood what you did with the structure. Soooooo, a BIG “THANK YOU” for your feedback and your help with restructuring the copy!

Step 2: Hone Messaging + Fill Holes with Swiped Copy

Once I’ve got the structure of the page all fixed up, it’s time to make sure the copy matches what the prospect is thinking.

Before I start working, I ask my fabulous clients to share me on any qualitative customer research they’ve got — things like survey responses, interview answers, customer service logs, etc.

These sources are a G-D goldmine of insight into the words that prospects need to read in order to identify and trust the copy.

Plus, they’re chock-full of descriptive, “sticky” phrases that can go straight into the copy verbatim.

For example,from research for a mattress manufacturer:

“After a year of playing Goldilocks and trying out beds at every mattress store in the Salt Lake Valley we stumbled on [CLIENT NAME]…” 

And from research for a veterinary pharmacy:

I wish you guys were my primary care and not just for my dogs ☺” 


^^^^ These tasty morsels are pre-written copy.

Insert them into the spaces you’ve left open to assuage fears, explain specific benefits, and persuade prospects.

Step 3: Punch That Sh** Up

This is the fun part! After the restructuring and message-honing, it’s time to make the page copy stand out from competitors.

stand out

There are many ways to stand out from the crowd. Laser eyes are two of those ways


I punch up copy in two ways: by making sure it has its own voice, and by adding humor where appropriate.

First, give the copy its own voice

“I hate to admit it, Lianna,” you say, glancing furtively around the coffee shop. “The truth is that ‘voice’ is one of those things I always reference, but I couldn’t really define it even if you held a NERF gun to my head.”

I’ll save my darts for the next guy, ‘cause I got you, fam!

In her excellent guide on writing voice, Abbey Woodcock defines voice as made up of three parts:

– Tone — The copy’s emotional background or inflection, AKA where the copy is coming from. Tone can be excited, gloomy, sarcastic, angry, you name it.

– Cadence — The rhythm created by the copy’s sentence length and variety

– Vocabulary — The words your copy uses to convey meaning

So, when I’m punching up copy line by line, I’m essentially:

– Matching the copy’s emotion and inflection to the way the client wants to come off, and/or the way they’d like the reader to feel

– Varying sentence length so the copy doesn’t feel endlessly monotonous or — on the other end of the spectrum — choppy and interrupted

– Using casual and accessible language wherever possible, so the copy is easy to read

Then, add humor where it matters

As you might expect from a company named “Punchline,” I’ve got a loooot to say on the topic of humor.

One face-palmingly easy way to inject your page with humor? Add a GIF. Here’s how to identify where you should use GIFs, and how to pick the right one.

If you want to know even more about being funny on paper, read my post for Autopilot: 10 Easy-As-Pie Punchups for Warmer, Funnier, More Personable Copy.

Finally, I explain with a video walkthrough

I rarely send *just* a GoogleDoc to clients, even if I’ve worked with them before.

Instead, I’ll make a 5-10 minute video walkthrough to explain how and why I’ve reworked the page. THEN, I’ll link ‘em to the GoogleDoc — so they’ve always got context for changes that might not be immediately intuitive at first glance.

Nope, my face is not featured in the videos. Which is fine, because by this point it’s wan, puffy, and haggard, like 95% of the GOP.

Uppercut delivery video still

Actual still from an Uppercut delivery video, with client name obscured because I am an international spy

Clients love not having to figure things out for themselves. Here’s what the client above said:

“I just watched the video and quickly scrolled through the notes. I’m definitely going to start implementing these starting this afternoon. Great idea with the video response. Thanks for that.”

Congrats! Now you know all my secrets and you don’t have to pay me. Wait… what did I just do??

As for me, after a long day doing Uppercuts for all sorts of businesses, from motivational speakers to sugar-dating profile writers, it’s time to slink back to my bed of Ben Franklins (which is much less comfortable than a real mattress, but gratifying in other ways).

Are you gonna try my Uppercut process? Leave a comment and let me know how it works for you!


5 Post-Purchase Sales Emails Your Ecommerce Store NEEDS to Be Sending

5 Post-Purchase Sales Emails

Call it whatever you wanna call it — retention, post-purchase, lifecycle.

The fact is that for virtually every online store, revenue growth depends on getting more repeat customers. The work ain’t over just because you got the sale!

And while sending newsletters and new product updates is all well and dandy, there are LOTS of other types of emails stores can send — SHOULD BE sending — to encourage repeat purchases.

I’ve collected 5 recent, real-life example emails from my own inbox, and organized them from most common (the types of emails I see all the time) to super rare (AKA the types I WISH I saw more often).

Take a look.

Then emulate the sh** out of them, because that’s how you up your game, brah.

5. Most Common: The Related Products Sales Email

(Click the image to open it full-size in a new tab.)

FROM: Best Buy Weekly Ad

SUBJECT LINE: Your LG – 43″ Class (42.5″… <— missing parenthesis theirs; it’s either sloppy proofing or sly genius to get people to open the email

best buy personalized recommended products

Why I Love This Email:

This is one of the most common types of post-purchase emails online stores send–and for good reason. It leverages data about the customer (in this case, a recent purchase) to suggest related items.

This email is personalized to me and my recent order from Best Buy (a TV to replace the one my ex took when he moved out. I’M FINE, DON’T WORRY ABOUT ME).

Notice the encouraging, specific social proof: “Customers who bought your TV also bought…”. Best Buy follows that line with “For your new TV, we recommend…”

4. Common: The Birthday/Anniversary Coupon Sales Email

(Click the image to open it full-size in a new tab.)

FROM: Nisolo

SUBJECT LINE: A birthday treat.

nisolo birthday email

Why I Love This Email:

Honestly, who doesn’t need an excuse to buy more shoes?

Stores can capitalize on customers’ goodwill by sending a coupon on any or all of these occasions:

  • The customer’s purchase/membership anniversary
  • The customer’s birthday
  • The store’s own “birthday”/founding date

Here, Nisolo uses its own store anniversary as an excuse to hold a two-day sale.

I love that this email focuses on the founders and their picks instead of highlighting products by themselves. It keeps the focus on the ostensible “celebration,” and directs readers to a cherry-picked selection instead of tossing them onto a generic product category page.

3. Less Common: The Limited Stock Sales Email

(Click the image to open it full-size in a new tab.)

FROM: Rothy’s

SUBJECT LINE: Retiring Soon: Shale Ribbon Stripe

Why I Love This Email:

Another win for personalization here! Rothy’s (either lovingly or creepily, depending on how you feel about data) knows I’ve added the Shale Ribbon Stripe flats to my cart in the past.

And then walked away, because how many pairs of $125 flats does a girl need? Please don’t answer that.

But this ISN’T an abandoned cart email. Though Rothy’s also sends those.

This is a bald-faced appeal to my FOMO, and I’m lovin’ it. Do I want Rothy’s to retire these cute-ass shoes? I sure don’t!

Am I gonna snag a pair before they get “retired,” a la the Mafia? I SURE MIGHT!

Rothy’s knows I wanted these flats. And they know that the flats might sell out before I see this email*, so they helpfully included two other links to shoes I’ve ALSO expressed interest in.

Touche’, Rothy’s. You might get me to buy another pair sooner rather than later…

* They did. They sold out. God damn it.

2. Rare: The Post-Return or Cancellation Sales Email

(Click the image to open it full-size in a new tab.)

FROM: Dropps

SUBJECT LINE: Just checking in.

dropps cancel subscriptionWhy I Love This Email:

Look, I could write a book about Dropps’ marketing copy. It’s so hit-or-miss! Some of the auto-emails are so great, and some are so meh! Some are still set to their marketing/shipping platform’s default copy!

But for now, let’s zoom in on this email. Which I love.

How often do you see a sales email from a subscription company AFTER you cancel your subscription? Answer: Not often enough.

Dropps didn’t take my cancellation personally. They acknowledged that maybe it wasn’t the best fit for me. And they sent me a cute cocker spaniel with specific alternative product suggestions, then locked it in with a 20% off coupon code.

Remember–if a customer cancels their product subscription but doesn’t unsubscribe from your list, you can still email them! And it’ll be easier and cheaper than getting an all-new customer.

Same goes for non-subscription-model businesses. If a customer returns an item to your store, why not send her an email that says something like,

“Hey, Lianna! Saw that you needed to return that Extra Large Tyrannosaurus Rex Head because it didn’t fit–bummer! In case you’re still looking for something similar, here are a few products you might like.”

In fact… I got a very similar email recently.

It’s the rarest of all ecommerce sales emails: The Post-Return Personal Shopper Sales Email.

And though it’s got a terrible subject line, its intentions are pure gold.

1. Literally Never Saw It Before This: The Post-Return Personal Shopper Sales Email

(Click the image to open it full-size in a new tab.)

FROM: Mott & Bow

SUBJECT LINE: Mott & Bow/Styling Team/Request Inquiry <— yuck, come on, y’all

mott and bow feedback email

Why I Love This Email:

First of all, it’s plaintext. It might well have been sent through a platform like Zendesk, but it doesn’t matter, because it LOOKS like a bona fide email.

Second, it’s short and to the point: “I want to help you find the perfect pair of jeans.”

Mott & Bow knows that just because I returned my first pair, all’s not lost. I might be ready to try again–so they sicced Liz on me to personally find a better fit.

Third, it helps Mott & Bow build a stronger relationship with their customers. Not only are they helping me satisfy my #RealNeed for good jeans, they’re collecting valuable customer research while they do it.

If you’re not sending emails like this to your customers who return products, you’re missing out on a HUGE opportunity to turn what was once a loss on both sides to a seriously satisfying win-win.

Hey, you know what I’d LOVE to do?

I’d love to write emails like this for your store. Let’s transform your one-time customers into repeat buyers! All through lil ol’ words! Click the button below to make it happen: