I’m really torn here.

I got an awesome email forwarded to me by an up-and-coming copywriter named Bailey Rogg. The email was from The Black Swan Group.

In case you’re not familiar, this is Chris Voss’s company.

In case you don’t know Chris Voss… he’s the guy who wrote Never Split The Difference.

And if you haven’t read that book then you might be a little stupid.


The email had a LOT of awesome things going on. It showed so much promise… and my gut reaction was THIS IS A GREAT EMAIL!!!!

But by my third and fourth read through it, I found a few huge missed opportunities.

Overall, I think it was strong and super effective. But I might have a few tricks up my sleeve to take this thing to the next level.

If this email were an emoji, it’d be:

???? Woozy Face

A yellow face with a crumpled mouth and a cockeyed expression, as if tired and emotional from inebriation or smitten with love. Depicted with raised or furrowed eyebrows and at least one eye half-open. WhatsApp’s design features a tongue hanging out.

Meaning widely varies, but commonly conveys intoxication or infatuation. Its dazed expression may also represent such feelings or states as bewilderment, irritation, disgust, exhaustion, wackiness, or complete satisfaction.

Courtesy of: https://emojipedia.org/woozy-face/

Lots of things to smile about with a couple of wonky bits we can straight out pretty easily.

Of course, we never poo-poo people on Email of the Week. We only build up people and shine a spotlight on companies, like The Black Swan Group, who are doing a lot of things well.


Without further ado…

Let’s dive into this week’s Email of the Week!

This is the 23rd installment of my Email of the Week series. (Catch up on previous episodes here.)

And in case you’re new around here, here’s how this all works…

The Rules For Email Of The Week

Each week, I go out into the wild to find a super-effective e-commerce marketing email… and I break down what made it work. My goal is for you to tune in each week, so I can teach you strategies and best practices YOU can use to make your own emails better.

I find these emails in my inbox, but I also accept suggestions from readers who have a remarkable email they’d like to share.

If you recently received an email that was so awesome it made your jaw drop, I wanna see it.

Forward it to me (chris at theemailcopywriter dot com) with a brief message about what you liked about it. If I choose to do a breakdown of the email you sent, I’ll give you a shout out and link to your site.

The only rule is… you can’t pick yourself.

Now then, without further ado, let’s check out the Email of the Week!

Hello… is it me you’re looking for?

Every company should have some kind of reactivation email campaign.

My personal favorite is Dean Jackson’s 9-word email.

As far as I’m concerned, that’s the gold standard.

Of course, there are many different strategies you can use to “re-engage” email subscribers. Sometimes it’s reaching back out to get them to make a purchase. Other times it’s just to get them to consume some content so they come “back into the fold.”

I don’t know what to recommend to YOU, because I don’t really know much about your business.

But this email Bailey Rogg sent me from The Black Swan Group does a pretty awesome job of doing the latter… getting their readers to consume content so they get interested in their products and services again.

Let’s take a look at how they did it…

Subject line: Are you still there?


Take a moment and look at that subject line.

That’s pretty damn good.

Know why?

Because it’s subtle.

It’s straightforward.

It looks, feels, and smells personal.

And it raises a question that’s a little difficult to ignore.

You don’t have to pack 14 words into a subject line to make it “sexy.”

You must ALWAYS write to achieve your objective. And I think this subject line does a great job with that.

One other cool thing about this subject line is that the line: “Are you still there” is a phrase you might hear on a phone call if you’ve been silent.

If someone’s been droning on for 20 minutes and they haven’t heard a peep… they might ask that question.

So this question is kind of crossing communication mediums, from phone to email. I thought that was pretty interesting. And I actually like the technique here.

Ok, let’s dive into the body…

Can I ask a question?

Why the fuck do companies put these big-ass pictures in their emails before the copy?

I could be wrong… but this looks like a stock photo.

What does this stock photo add to the email?


If you can defend the use of stock photos like this in emails, I want you to leave a comment and this blog post and explain it to me because I cannot, for the life of me, figure out why companies love doing this in their emails.

It buries the copy.

It adds nothing.

It does nothing to move you closer to achieving your objective.

And if you have to “remind” me who you are by including a picture and a logo… maybe you’re not staying in touch enough, or maybe you haven’t done a great job of building a bond with me with your emails.

That’s my opinion on the matter.

I’d say this is messed opportunity #1.

This email could have been a PERFECT “suspiciously personal” email. If you get rid of the border and dumb stock picture and formatting and button… it would actually look like a REAL email from a REAL person.

And real emails from real people get read and acted upon way more than emails that look like ads.

The reason I’m so pissed is because I think they have a great hook.

They took a really awesome angle, but they buried it with this picture.


Let’s look at that copy.

The salutation and opening line are actually pretty good… because they look and feel personal.

Only thing I would change is “keeping up with our content lately.”

That sounds like I’m being reprimanded a bit.

Also… what does keeping up with our content actually mean? That’s marketer speak.

You have to think like the fish, not the fisherman.

I, as a prospect, don’t really give two shits about keeping up with ANYONE’s content except for my own.

An alternative angle:

“Hey Chris. It looks like you didn’t get a chance to read our latest article. I think YOU would love it! (Tip #5 will probably make closing sales a lot less nerve-racking.)”

I just farted that out.

I could probably make it even a little tighter, but whatever.

See the difference tho?

It’s subtle, but I think it can be a bit more “human.”

The next line is a great angle to take…

While you’ve been too busy to check out our articles, your counterpart might be educating themselves on new techniques to bring to your next discussion.

I love this angle, but I hate the execution.

Letting people know their competition is doing something they are not is a good way to get people to move their ass and do the thing you want them to do.

So I will award points for that.

But I take issue with the way this is worded.

“While you’ve been too busy…” sounds a tad bit needy.

Counterpart – sounds like corporate speak.

next discussion – I could be wrong, but is this the best way to describe why we need this info? How about deal, sale, negotiation, etc…?

Again… it’s an incredibly effective copy angle in this context… but the wording is just a little too stiff for my taste.

The next line is pure gold though:

“Don’t worry. We’re still rooting for you.”


Simply flawless.

You’re off the hook. We’re on your side. We got your back. Us vs them.

There’s a lot of persuasion power packed into those 7 words.

That final line of copy seems a little too passive.

I’d say something like:

“Check out the new articles we just posted: I’d be SHOCKED if you didn’t double your closing percentage…”

See how that just packs a stronger punch?

Or, how about this…

“Check out the new articles we just posted: your boss’s jaw is going to drop when he sees you command the room in your next quarterly meeting.”

Or, whatever.

See what I’m saying, though?


Visual persuasion.

Make it HUMAN.

Ok, one more thing…

I don’t really love the button here.

If it were my email, I’d make this completely plain text.

I’d make this look like I just dashed this off in Gmail.

I’d strip out every design element except for the text, including the button. I’d just hyperlink some text instead.

People know what links are and how they work.

The internet has been around for a little bit now.

Ok, let’s wrap this puppy up…

I am OK with the sign off.

I love how it’s signed from a person, not from the ___ team like a lot of companies do.

Now, after that, you’ll notice ANOTHER big picture.

Is this one a stock image, too?


I’m not sure.

Maybe not?

Either way… what does this do for you?

Does this image being in the email make you want to read and/or buy from this company?

Personaly, I think it’s wasted real estate.

I also think it draws your eyes away from the copy… which is the most important part of the email because of the awesome hook they used for this automation.


Total Woozy Face emoji.

I loved this email. There were parts that chapped my ass a little bit.

But overall, I think this is probably an effective email.

I learned a lot breaking it down.

Hats off to The Black Swan Group Team.

I love your work, I love your book, and I hope you guys continue to kick ass and take names.

Special Shout Out to Bailey Rogg

I gotta say…

I really like Bailey Rogg.

Bailey and I met a few months ago at Copy Chief Live. He’s a great dude, and he’s quickly becoming a lethal email copywriter.

Case in point:

He hired me for a consulting session to help him strategize an email sequence he was writing for a client. I’m pretty sure he paid out of pocket (which I’m super impressed with, because it shows the kids got balls AND brains… unlike a lot of ther copywriters who “say” how dedicated they are.)


We do our all, we map out the campaign.

He goes and writes the thing… and it does more sales In four days than his company has done in the previous four months, all from email.

Pretty incredible, right?

I give Bailey all the credit.

Like I said… he’s going places.

The dude has got some chops.

Oh yeah… AND he’s an Email Copy Academy student. You know what they say: success leaves clues.

Anyway, anyway…

Here’s what Bailey had to say about this email:

Hey Chris,
This email made me immediately go to their website and check out the resources. (Resources behind a squeeze page…)

Short and to the point. But great use of authority, personal communication, and just a little competition.

A little longer than the 9-word email, but same general idea.

Thought you might enjoy.
Bailey Rogg
I agree with everything in Bailey’s analysis.
Couldn’t have said it better meself.
I think you should get on Bailey’s list email list. Go to: https://www.thecopyoperator.com/ and get on his list right now. And if you’re looking for a proven email copywriter, hire Bailey to help you with your emails.

Big Takeaways from The Black Swan Group’s Reactivation Email

  1. Make your subject lines look like something an actual person would say/write.
  2. Stock photos are dumb and do literally nothing except take up space and distract people.
  3. Big images bury great copy.
  4. Write in a “suspiciously personal” tone.
  5. Plant a seed of doubt in your reader’s mind.
  6. Automate emails to encourage prospects to perform specific behaviors (like re-engaging after going cold).
  7. Never be needy.
  8. Let people off the hook and forgive them for their misdeeds.
  9. Throw rocks at their enemies.
  10. Plain text emails work better.
  11. Don’t use buttons when the message should look and feel personal.
  12. Sign off with your name, not from the ____ team.

What You Should Do Now

  1. Subscribe to my email list so you can get ALL of the Emails of the Week delivered straight to your inbox, automatically.
  2. Leave a comment for me below and let me know what you liked about this email.
  3. Send this breakdown to someone you know who has a physical product business. You might help them write an awesome reactivation email.
  4. Invest in one of Chris Voss’s programs. If his other products and services are as good as his book was, you’re definitely making a smart decision. That guy is a BOSS and he knows his stuff.

2 thoughts on “[Email of the Week #23]: The Black Swan Group”

  1. “I just farted that out.” I know! I seem to do that all the time, but I still can’t convince people to pay me big money.

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