Funny Cold Email Copywriting

In this post, I’m going to talk about my approach to cold email copywriting.

It’s not just my approach to writing cold emails, it’s my approach to writing any form of sales copy that’s directed at a cold audience.

The primary reason people use cold email is to generate sales meetings.

There are 4 critical variables to this.

If you don’t get responses, it’s generally for one of these 4 reasons.

Data – Are you targeting the right people? Is what you’re offering relevant to who you are targeting? Are the email addresses you’re contacting accurate and up to date?

Copy – Does your copy stand out and get attention? Or does it blend in and look like everyone else’s?

Offer – Do you have a good offer that those you are targeting would likely be interested in?

Technology – If sending lots of emails, are you using software to send your emails and automate follow-ups?

Let’s look at the copy element in particular.

If you Google “best cold email template”, you’ll be presented with short, functional templates that make the assumption all prospects have the attention span of an underachieving goldfish. It would appear empirical that this is the approach one should take with cold email. This is why major reason people struggle to get responses to their cold email. If everyone is writing the same functional and formal style, everyone blends in. If everyone blends in, nobody gets attention.

To persuade someone to take a call with you, you need to get attention first.

So many cold approaches fail because they go straight to persuasion.

The very first line starts with something like … “We’re the best people in the world at X… We’ve worked with X client and our groundbreaking X technology is a world’s first…”

YUCK! Of course, that gets deleted!

Your job is to sell the idea that a call or meeting with you is not a bad idea.

Not to give every little detail – or to sell your entire offering in one go. Those steps come later…

Dave Trott talks about this when talking about effective advertising.

He brings it down to a level anyone can understand.

Imagine for a moment that you wanted your other half to make you a cup of tea or coffee.

You need first make an impact.


That gets her attention.The communication is next…

“Cath, will you make me a cup of tea?​”

However, that’s not very persuasive.

“If you make me a cup of tea, I’ll take the bins out.​”

The same rule applies to direct mail or cold email or any form of effective marketing or advertising.

You need to make an impact first.

Then communicate.

Then persuade.

You need to stand out.

Your prospect likely gets a ton of other letters and emails (and cold calls) – and they all look and read the same.

You need to get attention.

Without that, it doesn’t matter how good your communication is. It doesn’t matter how persuasive you are. It doesn’t matter how good your product or service is.

You need to get a reaction. An ‘ahhh’.

A nod. A smirk. A smile. A belly-laugh.

You need people to actually see and read and listen before you can communicate and persuade.

And being able to get cut-through – especially if it’s done in a unique or clever way – is somewhat persuasive in itself.​

I’ll give some specific examples of ‘cut-through’ copy.

I won’t read these out line by line, but I’ll read a few of the more important lines out, such as the opener:

“Greetings Helen,

You’ve never heard of me. (Hi, I’m Jon). I got your details from a list. gasp. But hey, at least you’re list-worthy, that’s gotta be worth something right?!”

Who says that?

Who opens, firstly, with “Greetings?”

And then states they are a stranger…… and then not only mentions that you got the prospects details from some list…. but further, compliments them on this, by suggesting by being on such a list, they’ve somehow ‘made it’, and they should be proud of such an accomplishment.

That last line, by the way, is what is known as a ‘reverse’ and it is my favourite kind of joke.

You see, I never studied copywriting. So I didn’t learn what I was supposed to do. I interrupted the pattern by default. Upon being surprised at the success of this approach, I took a look at the copy and that’s when I realised what I was doing​

I’ve been obsessed with stand up comedy, sitcoms, funny movies, satire and anything else that involves ending sentences in an enjoyable way. For a long time.​

I remember fondly watching comedy until 4 am all through my teenage years. I guess that was my 10,000 hours experience. If I’d known at the time I was working, I probably would have tried to procrastinate.

People say you should never use humour in business, and I understand why, but I’m here to tell you, that those people are wrong.

Well, they’re not wrong. They’re just less right than me.

Conventional wisdom would have you open with, and let me put on my most awful infomercial voice, to further discredit the approach:

“Dear Helen, Do you have problems navigating the ever-changing world of digital marketing?​”

People don’t talk like that, at least nobody I hang out with does, but everyone is writing emails this way.

If they even open your email, many people stop reading as their ‘Ah fuck. I’m being sold to’ alarm bells go off.

Not only are they being sold to, it’s worse than that, they’re being sold to in the most boring, lazy and robotic way.

I’ll go through a few other lines of copy from my original drunk email/letter.

My call to action:

“If you let me have a chat with you about your digital marketing, spectacular content creation or bedroom tidying needs, I will take you for coffee, lunch or tequila shots and promise to be somewhat entertaining. If you’re lucky, I may even wear a top hat. First off, I’d love to provide you with some ideas you’re free to steal.

I’ve included a sticker containing a picture of a ferret that has been dressed up. According to the Internet, his name is Colin. I trust this will charm you into submission.

I await your profanity-filled response.”

This is the type of copy that makes many ‘etiquette’ following people feel unwell.

Yes, I did include a picture of a ferret in bunny ears.

People often ask me, “Aren’t you worried some people won’t want to work with you with such an absurd approach?”

I tell them that is not a painful side effect, rather a useful and deliberate feature.

The stern and the self-important immediately disqualify themselves.

When I say the stern and the self-important, you might ask, who am I talking about?

You’ve probably come across one of them….You know… the type of person who would type … or even… god forbid… say out loud, “You should be more professional” without a hint of parody.

The type of person that believes blandness is a quality deserving of reverence.

There’s nothing wrong with the bland, the stern or the self-important, I just think they work with their own kind. 🙂

They probably think the same of me. And that’s fine.

I have standards too, they’re just different standards to those of my detractors.

When writing cold emails, the biggest single factor is getting attention. Humour is a great way of doing this. It’s also a great ‘qualifier’. You can feel safely inoculated from every working with self-important “professional” people who you know would make the absolute worst kind of client.

While at the same time, generating gushing, positive responses from prospects who are enthusiastic about speaking to you.

For example:

Positive Response To Charming B2B Cold Sales Email Template: Dear Jon, Firstly let me congratulate you on the most entertaining cold call/email that I have received recently, or possibly ever. And I get a lot. It's so rare to get a truly creative communication from an agency that purports to be creative, so thank you. I'm going to build a Wall of Fame for examples of good marketing, on the basic of your letter. It might be quite a small wall though, or perhaps just a few tiles. Let's talk? We can probably use some help with value propositions, or just our general thinking. You don't need to wear the top hat, but if it helps, don't let us stop you.

I hope you found this useful – and you give my weird ways a go.



Free Cold Email Template Download

Want to get a copy of my original drunk cold email copy that generated responses like the one below?

B2B Cold Email Template - Positive Response From Prospective Client From Charming Cold Pitch: Jon, Apologies for the delay in responding. I receive a lot of unsolicited mail and read virtually none of it - so sending me something which I actually read and remembered is a real achievement. On the basis of that (and because the author John Buchan may be the most famous person to have come from my home town of Perth) why don't we get together for a coffee and we can see whether there's something you can do for us or whether indeed I ought to be pointing you to someone else. My PA will be in touch to set something up - probably a few weeks off as the first half of March is pretty hectic

Well, you can.

Enter your email address in the box below and hit the magenta button with all of your might.

(You’ll also get a copy of my magic email cheat sheet, which runs through some of the key principles behind my successful cold email. BONUS! 🙂

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