Here’s to conversational copywriting.

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While I didn’t know it at the time, my first run-in with conversational copywriting happened while doing some freelance ink-slinging for The Hustle, a media empire lead by a wildly ambitious founder named Sam Parr.

I was immediately awestruck with their brand after finding myself on their email opt-in page that was unlike anything I had ever seen before.

It had a witty, clever, edgy, laissez-faire tone to it that felt more like a conversation with a friend over a cold beer versus an actual sales pitch.

And, ironically, after leaving the page without feeling like I had been sold… I was sold.

I, like so many others, coughed up my email. Hell, coughed isn’t the right word… I practically threw at them.

Why? Well, the short answer is that The Hustle is the best in the world at a style of communication called conversational copywriting.

For the long answer, you’ll have to keep reading…

What is conversational copywriting?

Conversational copywriting is exactly how it reads — it’s copywriting that is conversational — it’s the simple (or perhaps not so simple) act of writing how you speak.

The vast majority of copywriting you come across today falls into two categories… sales copywriting and advertising copywriting.

Both are effective in their own ways.

Sales copywriting originated from direct response copywriters who made a living sending long sales letters directly to people’s mailboxes marketing shit like vacuums and Tupperware.

While it certainly drives sales, brands must be careful of becoming overly bullish on sales copy.

You know the saying… too much of a good thing.

Too much sales copy (and too pushy of sales copy) leaves folks feeling like they’re trapped in between two mall kiosks with Benjamins taped to their foreheads.

While there is a time and a place for sales copywriting, it’s like balsamic vinaigrette or soy sauce or whatever other kind of condiment you can think of that’s really fucking strong if you use too much…

It’s better in small doses; a lot can ruin the meal.

Advertising copywriting, on the other hand, is something a little bit different. This style of copywriting was used by brilliant admen like Albert Lasker and later David Ogilvy.

If you’ve ever felt yourself go weak in the knees because of a slogan or a tagline, that’s advertising copywriting.

It’s the pretty shit you see on billboards (the good ones) and street posters and magazines, as well as the clever word-smithery you hear on the radio, television and in the openings of YouTube videos and podcast episodes.

(If you’d like to see an example of advertising copywriting, take a look at this wonderful ad done by a copywriting legend named David Abbott or this deep exploration of M&M’s slogan).

Now, somewhere in the middle of advertising copywriting and sales copywriting sits something magical… conversational copywriting.

Conversational copywriting and the craft of writing how you talk.

I would almost describe conversational copywriting as a thoughtful meshing between advertising copywriting and sales copywriting.

Or, more simply, writing how you talk.

I’m know for having a more conversational tone to my writing, something I help entrepreneurs, marketers and other writers achieve in my copywriting course.

It was something I learned whilst writing a few ads for The Hustle early on. They have a tremendously talented team of writers and editors that take an interesting approach to their copywriting and marketing as a whole… they’re almost anti-advertising in a way.

Their marketing doesn’t feel like marketing, their advertising doesn’t feel like advertising and their copywriting doesn’t feel like copywriting.

It’s just, more or less, a conversation between them and the reader. Sort of like how this article feels like a conversation between the two of us.

( Basecamp, a project management and team communications software based in Chicago, is also incredible at conversational copywriting).

An example of where I’ve used conversational copywriting in my own work is on the “thank you” page I send people to after they’ve subscribed to Sticky Notes, my weekly email list.

Folks seem to really appreciate the conversational tone rather than the stale cookie-cutter “thank you for subscribing” email they get everywhere else.

But, enough about Honey Copy and The Hustle. Let’s talk about how you can begin applying conversational copywriting to your own marketing.

A few pointers on writing conversationally.

Firstly, start recording yourself pretending to sell something aloud. Then, replay the recording. Cut out the bits that sound like you’re a used car salesman and write down the lines that feel like you’re talking to a friend.

Secondly, before running with the copy you’ve written, read out it out loud to yourself. Hearing what we’re reading allows us to turn on our bullshit detectors and determine whether or not it sounds like “us” or “our brand”. If we’re not believing what we’re reading… how can we expect the reader to?

Thirdly, consider investing in a damn good copywriting course… here are my five favorites.

And, finally, read writers outside of marketing and advertising like Ernest Hemingway, Charles Bukowski, Anne Lamott, Anthony Bourdain.

The novelists really are the only ones that actually know what the fuck they’re doing.

By Cole Schafer.

Sticky Notes is my email list reserved for entrepreneurs, creatives, marketers, writers and freelancers looking to sell like hell (without losing their soul).

Originally published at on April 18, 2020.

Written by

I write pretty words and sometimes sell things.

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