Welcome to The Newsletter Operator!

In today’s email:

• One ad that drove 300-600k+ subscribers and why it worked

• How one newsletter grew to 250k subscribers in 3 years

• A welcome email hack to get 20X more replies

• And much more…

Let’s get started.

Deep Dive

The Greatest Newsletter Ads of All Time

When I started working at The Hustle in 2020, one of the first things I did was dive into their facebook ad account.

I wanted to see what worked now and historically, and how I could improve it.

After looking through years of ad account data (they had been running FB since before 2017) I was shocked to find one ad had driven the vast majority of all results.

This was an ad account with millions of dollars in spend, and one ad drove 80% or more of all historic conversion. Wild!

They called it the “cold man”.

It’s so simple:

• A testimonial

• A stock image

• A headline

This ad ran and worked for ~4 years and the only thing that changed was the subscriber number in the headline.

It went from:

• “500k professionals”

• “600k professionals”

• “700k professionals”

• “1M professionals”

• “1.5M professionals”

Most of these “professionals” (our subscribers) were coming from this one ad!

It’s crazy. I’ve seen in 50+ FB ad accounts and never seen one ad so dominant.

So naturally I wanted to understand:

1. Why it worked so damn well

2. What are the other greatest newsletter ads of “all time”

Let’s start with number one…

Why The “Cold Man” Is One Of The Most Successful Ads Ever

There are 3 main elements to the cold man.

1/ The primary text

"My boss thinks I'm smart (I'm not). It's because I read The Hustle (and he has no idea it exists)." -- A Reader of The Hustle

Here’s why this works:

- It’s a “testimonial” and therefore more believable than normal copy (Turns out, the “Reader of The Hustle” also worked at The Hustle, so this is only technically true.)

- It reveals a secret. Everybody wants to know things that others don’t.

- It promises what we truly desire — to sound smarter and be superior to our boss, friends, and co-workers.

This is what people actually want, but rarely admit.

So many newsletter ads focus on “learning”, “news”, and “insights” about a topic. Not the core desire behind those interests.

2/ The image

- It grabs attention with big eyes and a face that takes up most of the image

(Eyes, faces, and hands grab attention. Always have at least one in your ads).

- It looks like it could be the person who said the “testimonial” above

- The “cold man” looks to be in the primary demographic of The Hustle’s readers: Men 25-45

3/ The headline

The email 700k professionals choose to start their day

- Shows consensus - If 700k professionals read this email, maybe I should too… Or I should at least check this out.

- Creates curiosity - There’s an email 700k people read every day? What is it? What am I missing out on?

What are the other greatest newsletter ads of all time?

After helping 20+ newsletters with paid marketing, I’ve seen a ton of extremely successful ads. IMO, these are some of the best:

1/ More from The Hustle

This one worked amazing because at the time FB cut off the part of the copy that said: “A Hustle reader”. It just looked like a testimonial from Mark Cuban.

2/ Videos based on “the cold man”

At The Hustle I made a ton of video ads based on the copy from the “cold man”. These worked great and ran for years. Here’s the link to watch them.

3/ The Milk Road

The same type of copy worked for The Milk Road, but in the format of memes and short TikTok style videos.

3/ TLDR Newsletter

Love these. They have been running for over a year. Link to video here.

4/ DTC Newsletter

Link to video here.

5/ Web3 Daily

So good. They have been running variations of this ad for 1+ year.

6/ 1440

Testimonials work. Even long copy like this.

3 Examples You Can Steal

1/ A welcome email tactic to get more replies

By asking for a short and simple reply to his welcome email, Justin is getting 20 times more replies.

2/ Grit Capital landing page

I love this landing page copy and logo.

It lists 3 reasons why you should trust this newsletter:

• Written by a $100MM portfolio manager

• The #1 finance newsletter on Substack

• Read by 100k+ hedge funds, billionaires, investment advisors and regular investors

Plus, the logo adds personality by showing an illustration of the writer.

3/ How Nathan Baugh added $1.5k+ profit per week to his newsletter

Nathan breaks down how to create and sell a simple digital product.

The 5 Best Links

1/ Bill Bishop (the 1st Substack creator) on building a solo newsletter business

This is one of the best interviews I’ve heard on building an indie media business. For those who don’t know: Bill is the cofounder of MarketWatch and the creator of Sinocism.

2/ How Codie Sanchez Grew her newsletter to 250k+ subscribers in 3 years

Awesome breakdown from Chenell of Growth In Reverse.

3/ A 2-step framework to increase your open rates

Every newsletter needs to understand this.

4/ How WorkWeek added 120k+ subscribers in January

I love this breakdown from Adam Ryan. He shares WorkWeek's open rate, CTR, and growth channels from January.

5/ StackedMarketer’s journey from 0 to 50,000 subscribers and $685k/year in revenue

Emanuel explains how he got there and what he would do if starting again from scratch today.