How not to write a terrible cold email

I have blocked over 1,000 people from ever ending up in my inbox again.

Today, we dive into what makes a cold email work—and what makes people want to immediately mark you as spam.

– Neal

Insight from us.‍

Cold emails and DMs are getting damn near constant.

Our brains are INCREDIBLY good at quickly identifying it as spam and:

Ignoring
Archiving
Reporting

So here’s a bunch of tactical ways to not be ignored (and at the end, I’ll share some of the most over-used tactics that people still recommend):

Trick #1: Make it warm

If you got a personalized message from your favorite founder, author, influencer, or celebrity, you would welcome it, read it, and happily respond.

And you’d be extremely forgiving.

Here’s how to make it warm:

Produce a lot of free content on LinkedIn, Twitter, newsletter, YouTube, podcast, etc.
Then engage with people who engage with you. Engage with others, writing and commenting on relevant posts in your niche.
Eventually, DM them a personalized message to get to know them, give them a free resource, or pitch an offer (that you know they’ve likely had some exposure to).

Your response and success rates will be WAY higher, and you’ll be burning far fewer bridges.

Trick #2: Short and simple

I can immediately tell it’s a cold email when I see 100+ words, and it's all perfectly formatted.

The cold emails I’ve actually responded to?

Short
Simple
Casual
To the point

Here’s a cold email we received from Sponsy that led to us (and several other newsletter operator friends I know) becoming a customer:

Here’s what it does well:

It’s three short sentences and gets to the point quickly.
It doesn’t try so damn hard to fake a connection.
It’s focused on my problems and how they can solve them—not about how great they are.
It’s well-targeted. They knew we had newsletter sponsors, and I likely had those problems before sending it.

Trick #3: Put in the work

Our top-performing cold outreach campaign for a client was directly a result of putting in the work before emailing people.

Our client allowed WordPress sites to create "members only" content (like Substack does now).

The most likely person to want this? Someone already using a competitor to run a membership program on their WordPress site.

What we did:

Paid for scrapers and VAs to go through lists of WordPress sites that sold memberships and label them based on the competitor they were using.
Researched people's top objections about each competitor.
In our emails, we highlighted those headaches and how our client's tool would relieve them.
We offered a free migration (because no creator wants to deal with the headache of migrating tools).

Our response rate was nearly 80%. And we booked tons of sales demos.

Trick #4: No links

Here’s an email I just got that has several problems:

It doesn’t know my name, so it just put it blank. So the opener of “Hi ,” makes it very clear it’s templated.
It’s from outreach@ and is from the Outreach Team… talk about personal
It’s all about them them them them—it provides zero value
It’s sent from their actual domain—meaning if I mark it as spam it can ruin the reputation of their entire domain.
Lastly, it has not one but two links

Why are the links an issue?

Well, for three reasons:

The first link is not something we use for anything—so it's a red flag.
Email providers (Google, Microsoft, Yahoo) are savvy that cold emailers add links. Adding links can ding your email reputation—especially when you’re sending a ton of them
It’s immediately obvious that it’s cold outreach spam.

Quick tips

Write like you would to your friend or partner.
Make it about them and their problem.
Personalize with variables that matter—like the tools they use or the problems they're experiencing.
Don't just spray and pray. Fewer, better-targeted emails.
Show it to a friend, partner, or family member for their honest feedback on whether it "smells" like a cold email.
Send using a different domain—so you don't accidentally destroy the reputation of your real domain.

Tired cold outreach tactics

Here are some of the top cold outreach tactics I see constantly that will make people ignore you or mark you as spam.

#1. The cringe/forced personalization

The opener to Kevin about his new role at DC is so forced, given the subject:

Another classic is the fake restaurant recommendation in the recipient's town, which is just one of the top restaurants on TripAdvisor.

It's very strange to get someone in Ann Arbor, Michigan, recommending a restaurant to visit in Victoria, BC.

#2. The "reply" or "forward" subject line

You've probably seen someone recommend writing a subject line with a "Re: " or "Fwd: "

I imagine this greatly increases the odds you open the email.

But at what cost?

Having them realize your first interaction with them was a lie?

#3. The horribly targeted

This email was quite frustrating:

Here are two reasons it's terrible:

Its subject line is horribly clickbaity and deceiving.
We very clearly have a website, yet he's claiming we don't. It would not take much effort to realize we have a Webflow website.

#4. The fake personalized loom video

Here, the person records one Loom video pitching their product.

But to make it look personalized, they cut it so that they're looking at the homepage of your website—maybe even fake scrolling through it.

The best was when I got a video like this from someone I've met before.

He could have just sent me a WhatsApp message, but instead, I got a cold email from him that was clearly fake, which made me instantly lose respect for them.

Be useful and real.

Most of this advice comes down to this:

Don't deceive people. Be real with them.
Don't do forced personalization. Only do it if it makes sense.
Don't spam people. Try only to contact people who need your product.
Don't just talk about how great you are. Focus on their problem.
Don't spray and pray. Be more targeted and build relationships.
Don't write an essay. Short, simple, to the point.

Something fun

BRAINS ARE WEIRD YO

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How not to write a terrible cold email