Dr. Spamlove: How I learned to Write Enjoyable Cold Email

I hope this email finds you well.

(Eye roll.)

With the proliferation of “cold email,” the garbage that comes to my inbox is beyond ridiculous.

When I first started using “cold email” back in 2010, it was a relatively simple proposition. I would see a product I liked, I’d write the CEO a simple email about it. I’d explain how I thought they had a cool product, how I ran an advertising agency, how we’d love an opportunity to earn their business, would they be willing to take a call.

About every fourth time I did it, I’d get a positive reply. It was laborious, and I didn’t do it consistently, and I didn’t follow up consistently, so I got mediocre results. I did get a couple of clients out of it.

Enter late 2010s, a colleague of mine shows me a program called Mailshake, and she says to me “Hey, it does those emails you used to write, but it will follow up and stuff automatically.”

I started looking at it. Yeah, it does. Cool beans.

Then pow, 2020, COVID hits.

DUN DUN DUNNNNN.

So in 2020, I started in earnest marketing for our agency using cold email.

I generated a fair amount of business this way. It was ridiculously time-consuming. I would look at prospects, attempt to deduce what motivated them, what problems they might be having, and so forth. I would study their LinkedIn profiles, I would study anything I could find about them. I would review Facebook information about them.

I would then, essentially, write an ad just for them.

The process I would develop, I nicknamed, craft batch email.

Just like Maker’s Mark isn’t Jack Daniels, my emails weren’t “cold email.” Each one was hand crafted and hand tested.

Now, “back in the day” (four years ago), oddly enough the biggest hurdle to deal with was the remark line – the “re:” line. In terms of cold email, your challenges to overcome are in the following order:

Deliver the email (largely a technical problem to overcome); open the email (a function of the remark headline); read the body copy (a copywriting problem); act on the call to action (also a copywriting problem). So, once you overcome deliverability problems, your next challenge is to get them to open the email.

Well, we (people) tend to open three types of emails: emails from people we know and want to hear from, emails from people we don’t know but have topics we care about, and emails from people we don’t know, but have topics that trigger our automatic responses to inquire, help, or react.

The phrase “quick question” was, until about 2022, one of the best performing re lines of all time.

But, like everything in marketing, once something like that “gets known” and people (mostly content marketing plebes of idiocy trying to pass themselves off as experts in social media) start sharing that fact, it totally goes to hell in a handcart in a hurry.

By the end of 2022, every cold email in America suddenly had the “re:” line “quick question.” ?Without question, the “re:” line “quick question” is probably now one of the worst-performing lines you could choose.

There are other lines that also perform very well, but I’m not about to share them, for the same reason that “quick question” demise – I have no intention of helping any of you destroy cold email any further than it has been destroyed already.

So here we are in 2024, and cold emails are just awful.

My favorite is, “I hope this email finds you well.”

I’m not sure why artificial intelligence feels that’s something it needs to say. But it is something it thinks it needs to say.

I find it amusing.

I get about 100 or so of these a week.

That said, I continue to book calls with prospects using my “craft batch email” technique, thus, cold email is not dead, it’s just hard.

Here’s why, and how, and what to do.

Why it’s hard.

Cold email is not about blast, or numbers, or volume. When I run my campaigns, they’re small, 20-30 people at a time.

Yes, you read that right.

Why?

Because I can’t write 20,000 ads.

I’m really good – but I’m not a machine.

I can, however, write a series of ads for 20 people, and test them, and watch them.

So I write for 20 people at a time, and test, and watch them.

That’s why it’s hard.

I test subject lines.

I test approaches.

I test calls to action

I test the number of follow-ups (which is more than 2)

I test how I follow up.

I test how we ask them to contact us.

I test everything.

If you’re wondering about technology I use – I’ve been using Lemlist for the longest time now, but lots of people use it now. When I started, few people were using Lemlist. Now I think Lemlist is one of the most popular platforms for cold email outreach. What I like about Lemlist is their approach is similar in many ways to my own. Their information on their website is quite good, especially for beginners. (www.lemlist.com)

You don’t need massive numbers.

That’s why it’s hard.

You have to get inside the prospect’s head and write a really good ad.

As for how?

You’re writing a good ad.

Most of you are not copywriters.

Most of you cannot write a sentence.

Now when I say that, I’m not trying to be a dick. I’m just being factual. Not everyone is a copywriter.

I’ve been trading words and ideas for money for thirty plus years. For me, writing is a habit. Writing comes naturally.

For many of you, you put things down in bullets. You can’t form sentences. You don’t know how to express a cogent thought. You can’t form an articulate sentence.

That is going to present a challenge in using cold email as a marketing tool.

So I get the whole “OOOH! ChatGPT!”

And the result is, “I hope this email finds you well!”

Yeah, bite me.

?You have to be able to talk to me in a manner that will move me.

Let me give you an example.

For one client, here’s what I wrote – got the client to call me in roughly 15 minutes after the email landed in his inbox. The email said something to the effect of this: “Dear ____, I see your products every time I fly, but I’ll bet nobody knows your company’s name. Would you like to change that? If so, I’d love the opportunity to show you how we’ve made company’s like _____ the best known leaders in their industry. When would be a good time to have a chat?”

Not kidding, my phone rang 15 minutes after the email was sent.

Client remains a client to this day.

Now, that was a guess on my part. An analytical bet on my part about their pain and their motivations. But it was a reasoned guess on my part, having studied them.

I got another client, a GSE manufacturer, using exactly the same technique. That client responded about a week later; however, they started making inquiries about me shortly after getting my email. I prompted them to act almost immediately.

I got another client, using exactly the same technique, who was a multi-billion dollar company. That client's boss directed her to call me the same day because the “boss” received my email and said to her, “If this guy has that much insight into our operations as an outsider looking in, then we need to hire him to help us.”

There are other stories like that – but the “trick,” if there was one, was actually taking the time to figure out what the prospect’s pain was and empathizing with it in a way that communicated to the prospect that I was in a position to do something about it.

ChatGPT cannot write that email. Full stop.

If you don’t know how to copywrite that email – you might have problems.

You cannot write 20,000 versions of that email unless you type like that Kermit the Frog meme.

Hence, why I do only 20-30 at a time. It takes me an entire day to do a series. It’s well worth it.

Finally, if you take all this time, and you provide value, it’s rare you’re going to get blasted.

I think I’ve written something like 15,000 emails over the roughly seven years I’ve been doing this (according to the stats I’ve looked up to write this article.)

I literally have received only one email where the guy said I should go fornicate myself.

So what kind of percentage is that - .000005 in decimal? So that’s .00005%?

That’s effectively zero.

I have had people, however, call me and ask me how I write emails like that. I had one marketing manager for an FBO ask if I’d teach him how to write cold emails like me. It never worked out, but I’ve considered a course. We even tried to make one.

There are two challenges to overcome: empathy and the writing.

Empathy is the bigger of the two challenges. If you don’t take the time to understand where the customer is coming from, you’re sunk.

The writing is actually the easier challenge to solve.

Now, I will admit this – I do use AI. I will also admit that my copywriters have also used AI. Those of us who are professional writers will use AI. We’ll throw our own writing into the AI engine and see what it spits out, and read it, and tweak, and throw it in again, and tweak, and remix, and tweak, and maybe use it, and maybe not.

What engines like ChatGPT and others do, is they’re essentially optimizing writing given the input they receive against the data they’ve been programmed against. I’ve been playing with AI engines that are being programmed against my own writing as well as some of the best advertising copywriting and copywriters ever. The stuff that has popped out as a result, has been quite extraordinary.

That said, it requires considerable skill to review to ensure that it actually produces “original” work and doesn’t plagiarize.

I see that a fair amount with AI work as well.

More and more I see the same AI text coming across in cold emails – which makes me think that essentially these AI bots are degenerating down to the same AI text because the people trying to write these cold emails have no idea what to say, so the regression model is just collapsing down ultimately to “Lorem ipsum dolor sit amet.”

It winds up being utter nonsense.

I suspect that as AI proliferates, it will only get worse. I’m working on something right now that I can’t reveal where I’m exploring the contours of AI and email outreach. When my experiment is done, I’ll give my readers the full details of what I was up to. Suffice it to say, I’m engaged in a “John Henry v. The Steam Engine” type test, putting my skills to the test against AI and with AI to see if there are ways to improve cold email outreach.

For now, I’ll continue trying to make craft batch emails that people like versus sending “quick questions” and “I hope this email finds you well.”

You should too. It’s well worth the effort.

PS: Well, we'll keep our fingers crossed, Dimitri, and remember, there's just one thing, we are all in this together. We're right behind you, Dimitri. We're with you all the way.

(Cue Vera Lynn "We'll Meet Again" music)

https://www.youtube.com/watch?v=RkpOSzcy0Vk

As an aside and off-topic, it's absolutely criminal that George C. Scott did not receive an Academy Award nomination for his role in Dr. Strangelove. While his performance in Patton was undoubtedly Oscar-worthy (and he received the Academy Award for his role in that film), his performance as Gen. 'Buck' Turgidson, a comedy role, is hysterical in this film, demonstrating just how amazing of an actor he truly was. He makes the film. That scene when he exclaims there's no fighting in the war room. Epic. Playing the funny man at times to Sellers. It's comedy gold that only Kubrick could imagine (a well-known "dramatic actor" as the comedy relief, and Sellers as the "straight man" on set every scene.)