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There’s a legend that’s told among content marketers about an email sent over 20 years ago.

Back in the 90s, when the internet was new and was little more than paper taped to the wall, a man named Derek Sivers started a website. He was an amateur musician who began selling his CDs on a site he built called CDBaby.

With every CD shipment an automated confirmation email was sent out to the customer. It was generic; it was dull; and neither of those were in line with the experience he wanted for CD Baby’s customers. So he changed it. Instead of the boring, typical “Your CD has shipped. Let us know if it doesn’t arrive”; Sivers sat down and wrote what is perhaps the most famous email ever written. It goes like this:

“Your CD has been gently taken from our CD Baby shelves with sterilized contamination-free gloves and placed onto a satin pillow.

A team of 50 employees inspected your CD and polished it to make sure it was in the best possible condition before mailing.

Our packing specialist from Japan lit a candle and a hush fell over the crowd as he put your CD into the finest gold-lined box that money can buy.

We all had a wonderful celebration afterwards and the whole party marched down the street to the post office where the entire town of Portland waved “Bon voyage!” to your package, on its way to you, in our private CD Baby jet, on this day, Friday, June 6th.

I hope you had a wonderful time shopping at CD baby. We sure did. Your picture is on our wall as “Customer of the Year.” We’re all exhausted but can’t wait for you to come back to!”

What started as a hobby in 1997 sold just over a decade later for more than $20 million. At the heart of his business was this 160 word message.

Shape your own legendary business by following these strategies when you craft content.

Is Your Content Compelling?

Did you want to keep reading the confirmation email? How did you feel when you finished? I felt like ordering another CD just so I could get it all over again.

Compelling content makes you want to keep goingwhether it’s reading, watching or sharing. Content produced for metrics is generally not compelling. But approach it with the audience in mind and it’s much easier to make good content.


When you’re struggling to imagine your audience, craft the content to yourself. Most of the time, the stuff you find interesting, fun, or boring, the audience will find interesting, fun, or boring too.   

Try This:

Years ago, Google translated its Terms of Service from the unofficial US language Legalese to just plain English. Few things are less read than Terms & Conditions and making them short and clear felt like a grand gesture of transparency to its millions of users.  

What Story Are You Telling?

Since the very first spark of fire, humans have been telling stories. It’s practically in our DNA.

A confirmation email’s sole obligation is to make a confirmation. When you order from Amazon, do you read the confirmation email? Or just check that it’s there so you know your order went through?

That’s all you have to do. But, craft content that tells a story and you open the door to connection with your audience. This works on two levels:

1. On a microlevel, each post presents an opportunity for storytelling. Infuse each tweet and Instagram post with personality and you’ll probably see an uptick in engagement.

2. On a macrolevel, all the posts together with your branding, copy, design, and what you choose to share and not share each dayit all adds up to a story about your company. What story are you telling your audience? Is the same story your audience is telling about you?


Imagine your company as the story’s main character. Give it attributes: witty, sharp, whimsical, collaborative, funny. Create all your content in the voice of that character.

Try This:

In its early days, Twitter was a fast-growing website with some rickety engineering that caused it to crash. A lot.

In 2008, its co-founder Biz Stone famously debuted the now-famous (if retired) “fail whale” (created by Yiing Lu). The image was his strategy to defuse the anger of frustrated Twitter users.

Fail Whale

Fail Whale image credit: Todd Barnard, CC BY 2.0, cropped from original

It didn’t completely resolve users’ frustration, but it did create a fan club. Years later, Twitter has outgrown the whale strategy, but it only takes a Google image search to unearth years of related riffs and memes.

Is It Human?

The most engaging content is that which feels most human. It has personality, and it demonstrates values.

CD Baby’s email makes us laugh, wonder, andultimatelywant to support CD baby! It’s clear that not only are there humans behind the company, but that they see that I’m human, too, and they value it.

In addition to being a paying customer, I am also a person who appreciates a good sense of humor.


Derek Sivers, founder of CDBaby and writer of this legendary email, puts it like this:

When you’re thinking of how to make your business bigger, it’s tempting to try to think all the big thoughts, the world-changing massive-action plans.

But please know that it’s often the tiny details that really thrill someone enough to make them tell all their friends about you.

Thrill your audience.

Try This:

Last year, Netflix made headlines for a cease-and-desist letter it sent to the owners of a Stranger Things-themed bar in Chicago. Unlike virtually every other cease-and-desist letter ever sent, the one from Netflix was, well, cool.  

They had a legal basis for lawyering up and stamping out the bar. Insteadundoubtedly aware of the attention they would receive for shutting down a popular barthey treated the owners as people: their people.

Instead of sowing negative press, they reaped praise.

You’re human. Your audience are your people.

Remember that, and in twenty years, the internet might just remember your business too.

Anna Ray Headshot
Anna Ray
Content Writer at

Anna Ray is a wordsmith and freelance writer based in Houston, TX. The internet's a noisy place. Want to be heard? Whisper.