I’m opening up the mailbox and answering YOUR questions!

Knock, knock…

Who’s there?

A salesman…


Have you ever tried to be funny as part of a sales message?

How did it work for you?

Or maybe you’ve heard you’re not supposed to use humor in copy…  And so you’ve stifled every one-liner, pun, or humorous quip that’s tried to make its way onto the page.

All the while wondering — could you be funny and still sell?

It’s Monday, which means it’s time to open up the ol’ mailbox and answer YOUR questions.

To have your question — about copywriting, marketing, entrepreneurship, humor, and more — answered in an upcoming Mailbox Monday issue of Breakthrough Marketing Secrets, click here.

Here’s today’s question…

Dear Roy,

Does writing funny copy (emails + web copy) actually work or not?



FIRST: A Warning!

There is a reason this is a rule.  First off, most people aren’t as funny as they think they are.

The people who make a living from comedy work 40 hours a week — or a lot more — thinking about how to be funny.  And even then, they often fail to be funny.

When you see a comedy special that’s taped and distributed on TV or Netflix or wherever, that special is often the result of 10 years or more of work.  Not that the writing of the special took 10 years.  But it took the comic 10 years to really hone their act before they could even think about having a special.

And even then, the special probably came together over the prior year (or longer), testing new material here and there, in front of live audiences.  One joke would bomb, and then another.  Then one would work, and they’d keep it.

In fact, in that way comedy is a lot like direct response marketing.  You test a bunch to find the few things that really work well.  And you never really know what those things will be until you’ve put them in front of an audience and measured the response.


Let’s say you really are funny.

Let’s say that in a group of perfect strangers, you’re often able to work the room and get a lot of people laughing.

If you try to translate that into a sales message — and especially, across media — you’ll often find your humor just doesn’t work.

Have you ever tried to make a joke in an email, and someone took you literally?  That’s the default.  That’s what you should assume.  Because when people read, the default is to take things literally.  In the case of a humor writer, it’s often the reputation of the writer or the cover blurbs that actually sets the expectation and frame of the situation that the person will be funny — and only when the expectations are right, the default reading of the text is looking for humor.

It’s incredibly hard for even really funny people to translate their humor into other media.

HOWEVER: There are success stories…

Not the least of which is Dan Kennedy, copywriter, platform seller, and lover of humor.  Dan actually wrote what I believe is the definitive book on the subject of humor in selling, Make ‘Em Laugh & Take Their Money.

Before you even try to be funny in a sales message, read that book.

57 times.

No more, no less.

Then you can make you first attempt at humor.

(Did you take that literally?  If you actually think you need to read it 57 times, that’s proof that it doesn’t matter if I think it’s funny when writing it, it doesn’t always come across that way.)

Here’s the big thing about humor and persuasion…

Selling FEELS serious.  Buying FEELS serious.

And things that feel serious increase our resistance.

If you can make persuasion feel LESS serious with humor — and you actually pull it off — it can reduce resistance.

You take the logical prefrontal cortex out of the picture.  And you get down into the emotional limbic brain, where there’s feeling.

But not just any feeling — humor is a GOOD feeling.

And ultimately, people buy based on good feelings.

If you can make people feel good, they want more of you.

They’ll do what you want them to do.  They’ll buy into your persuasion.  Believing, on some level, that it will lead to more good feelings.

The KLT secret, and humor in selling…

Remember the classic sales lesson, that “people buy from people they know, like, and trust.”

Here’s how humor helps all of that…


Humor is interesting, because it actually signals intelligence.  What you find funny tells someone a lot about your perspective on the world.  And so through humor, you’re revealing a bit of yourself.


Again, this goes back to the good feelings.  If you and I share a laugh, we will probably like each other more at the end of it.


There’s something about humor that diffuses mistrust.  If someone just made us laugh, it’s incredibly hard to mistrust them at that point.

In this sense, humor can be a quick way to rack up the KLT points with prospect — but again, only if you’re doing it RIGHT…

Self-effacing humor is almost always best…

Have you ever told a story about something really dumb you once did?  A big mistake you made, that now you can look back and laugh about?

That is powerful humor for selling.

As long as it doesn’t make your product or service look bad.  As long as it maintains your prospect’s trust in your ability to solve their problem or get them the desired outcome.

Making jokes about other people or groups is a minefield — you’re one poorly-landed punchline away from destroying any positive reputation you might gain.

Making jokes about your prospect is sales suicide — not very many people will do things for people who’ve just made fun of them.

But if you make a joke about yourself, or tell a funny story about you, your prospect can feel comfortable laughing at it because they’re laughing with you, at you.

You are being vulnerable.  That feels trustworthy.

You’re showing perspective.  The ability to laugh at yourself requires maturity.

And you’re showing growth.  Because you have to grow to have been embarrassed by something before, but find it funny now.

These are all endearing qualities.  These all score you points.  These will help with persuasion in the end.

Remember though, mostly we’re talking humor, not jokes…

Most good comedians today don’t even tell jokes.

They tell stories full of humor.

They make observations full of humor.

They may even slip some humor into an otherwise serious discussion.

But they don’t tell jokes.

That should be doubly true of using humor in persuasion.

The good news is, if your job is to persuade, you’re not EXPECTED to be funny.  A comedian is expected to be funny, so pretty much everything they do is supposed to fulfill that expectation.  You can actually get away with a little bit of humor as a salesperson or persuader, and it will FEEL especially funny because it’s better than what’s expected of you.

You don’t have to — and shouldn’t — keep a joke book nearby.  But if you have a humorous story that’s RELEVANT to the sales message, you can slip it in and see what response you get.

Don’t forget — your ultimate job is to sell…

You can go a lot deeper into developing your skill of humor.  You can buy Dan Kennedy’s book on humor and selling.  It wouldn’t hurt to take improv or comedy writing classes.

You could even hone your chops at open mic nights — if you’re ready to get absolutely eviscerated as you learn.

There’s nothing wrong with learning to be more humorous.

Frankly, you’ll probably lead a better life because of it.

AND you’ll probably sell better.  Not because you’re using humor more in your selling messages.  But just because you’re not taking life quite as seriously.  Because you’re approaching everything — including your persuasion — with less pressure and more lightheartedness.

And perhaps, you can try slipping in some humor.

You might even find it especially useful in places like email and content, where often it’s framing a selling message and not trying to close the sale as directly.

But don’t forget that ultimately your job is to sell.

The first purpose of the copy is to sell.

Any other purpose — such as getting a laugh — should be secondary and ONLY fulfilled when it carries that first purpose forward.

Most can’t pull it off.

Some can.

If you can, great.

If not, there are other ways to resonate with your market and create breakthroughs.

Yours for bigger breakthroughs,

Roy Furr