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Chapter 2 - Technology

The document is a comprehensive guide on building a successful newsletter business, focusing on the technology needed to operate effectively. It outlines key components of the newsletter tech stack, including website management, registration software, payment processing, email services, and analytics. The guide emphasizes the importance of adapting your tech stack as your newsletter grows and provides insights from industry experts on best practices and tool recommendations.
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0% found this document useful (0 votes)
24 views47 pages

Chapter 2 - Technology

The document is a comprehensive guide on building a successful newsletter business, focusing on the technology needed to operate effectively. It outlines key components of the newsletter tech stack, including website management, registration software, payment processing, email services, and analytics. The guide emphasizes the importance of adapting your tech stack as your newsletter grows and provides insights from industry experts on best practices and tool recommendations.
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd
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The Ultimate Guide to

7-Figure Newsletters
PART TWO: TECHNOLOGY.
So you want to build a newsletter biz?
Great. You’ve come to the right place.

We’ve spent thousands of hours untangling the newsletter business like no


one else.

This report is packed with lessons we’ve learned from growing our own email
list to 2m+ readers and millions of dollars in annual revenue.

It’s also filled with the wisdom of dozens of other successful newsletter
publishers -- from Morning Brew to Axios to AppSumo and more.

The media landscape is more important (and more competitive) than ever
before – 14k+ new email marketers join Mailchimp every weekday. And for the
first time in history, individual creators wield more influence (and have larger
audiences) than entire news organizations.

This guide will show you how to be one of them. How to stand out, grow, profit,
and influence like never before.
Millions read our newsletters each week
You’re about to learn from ..the industry’s best ..
We spent ~2+ years interviewing the most successful founders and operators in the newsletter space, like:

Jordan DiPietro, who spent 12 years building


Ryan Deiss, founder of DigitalMarketer. Shark
products at Motley Fool, and previously led
Tank star Daymond John says that Ryan’s
HubSpot’s media team.
companies “practically own the internet.”

Codie Sanchez, the VC who grew her newsletter Tyler Denk, employee No. 2 at Morning Brew, who
following to 10k readers in 30 days, and has used led their growth and product efforts from 100k to
it to generate millions in investment funds. 1.5m subscribers.

Noah Kagan, founder of AppSumo, which Alejandra Matos, senior director for audience
generates nine figures a year from its development at Hearst (and before that,
newsletter. Wirecutter)

Hamish McKenzie, co-founder of Substack (and Dan Oshinsky, who led the newsletter teams at
previously the lead writer at Tesla). BuzzFeed and the New Yorker.
We distilled their knowledge into a universal model
We call it “The Newsletter Engine,” and it’s the key to building a
profitable media business (in any industry).

Want to know a secret?

You don’t need a big audience to build a big newsletter


business…

And having a big audience won’t guarantee success either.

Instead, you NEED to know how the business model works; How
all the pieces fit together.

What are the options for monetizing an audience? And how do


you decide which to take? How much is a reader worth? And
how do you create something people love to read?

The newsletter engine answers all these and more. And it works
for every newsletter. Other types of media businesses too. Over
the next several chapters we’ll explore every piece… The Newsletter Engine
In this section…
…we’re gonna talk about the technology that powers newsletter
businesses.

We’ve talked to technical leads across the industry, including deep


dives with our team here at The Hustle, early technical hires at
Morning Brew, and the teams behind third-party products like
Substack, Pico, Sparkloop, and more.

We’ve distilled their advice into a few simple frameworks – things to


guide your decision making. We’ll unpack them here, including:

● The 5 key parts of the newsletter tech stack


● How your stack will change over time
● Where to start, and how to know when it’s time to upgrade
● Our recommendations for each layer of the tech stack
● And much more…

When you finish here, you should be able to decide what stage your
newsletter is at, what types of tools you actually need now, and
what you can safely ignore.

We’ll be looking at this


Table of Contents
O1 | The Technology You Need To Run Your Newsletter…….. 7
First, A Promise: We’re Going To Keep This Simple……… 9
The Most Important Thing You Need To Know…………….. 10
How Your Stack Will Evolve Over Time………………………….. 11
Key Considerations For Any Tool……………………………………. 12
All-In-One Solutions………………………………………………………….. 13
Custom Builds…………………………………………………………………… 16

O2 | The Newsletter Tech Stack……………………………………………… 18


Website………………………………………………………………………………. 19
Registration Software………………………………………………………. 23
Payment Processor………………………………………………………….. 29
Email Service Provider (ESP)........................................... 32
Analytics…………………………………………………………………………….. 41
Example Stacks………………………………………………………………… 46
01. The Technology You Need to Run Your
Newsletter
The first question most people have when thinking about newsletter tech
is: Which email service provider should I use?

We’re actually going to go a little deeper than that — touching on the five
key areas that technology serves inside your business:

● Your Website: For posting articles to the web and building


landing pages.
● Registration: For adding new subscribers to your list.
● Payment Processor: For billing subscribers or advertisers.
● Email Production: For designing and sending your
newsletter.
● Analytics: For monitoring your newsletter, marketing, and
website performance.

After showing you how each of these pieces work together, we’ll
explore some tool recommendations, and examine how the tools
you use will evolve over time as your business grows.
The combination of tools you use is called your “technical stack,”
and it can range from very simple to very complex.

On the simple side, some newsletters use a single all-purpose


platform (like Substack) that handles all five functions with little or
no modification. At the other end of the spectrum, publications like
The New York Times have built custom software to serve their
unique needs, with a team of technical gurus to maintain it.

Some layers of the stack matter more than others depending on


how your newsletter makes money.

For example, if your newsletter is strictly ad-supported, then the


most important thing is finding an ESP that can deliver your email
while avoiding the SPAM folder.

On the other hand, if you run a paid newsletter, then your


registration software actually matters more, since that’s how
people sign up and give you their billing info.

We’ll offer recommendations on both soon…

8
First, A Promise: We’re Going To Keep
This Simple
Other publications, like Motley Fool’s Ascent (formerly
Blueprint), do a fantastic job of breaking down the
nitty-gritty differences between software. That’s not our
goal here.

Our goal is to give you the best recommendation, based


on what successful newsletters are using, so you can
take action now.

If you’re technical enough to understand the nitty-gritty


stuff, you don’t need us for this.

And if you’re not… Well, nothing will make you want to


scream quite like a 10k-word treatise on the finer points
of newsletter tech.
The Most Important Thing You Need To Know…

… is that your tech stack is always a work in progress. As you build your
newsletter, you should expect to outgrow your software a couple of times. This
can happen for several reasons, including:

● Limited Functionality: Basic platforms like Mailchimp or Substack might


not offer features you’ll want as you grow.

● Pricing Inefficiencies: As your list grows, you may find you’re spending
more money with smaller software providers that aren’t built to serve
large newsletter companies.

● Lost Income: The limitations of your early tools will start to noticeably
undermine the amount of money you could be making if you had a more
robust technical system.
How Your Stack Will Evolve Over Time
After talking with key technical leaders at Morning Brew, The Hustle,
Axios, and others, we found that one question has a major impact on
your technical decisions: “How many people are you emailing each
day?”

The more emails you send each day, the better your tools need to be.
We’ll get into the specifics shortly, but for now just know that
newsletter companies go through three main phases:

● Early Phase: 0 - 100k emails per day


● Growth Phase: 100k - 1m emails per day
● Mature Phase: 1m+ emails per day

Early on, it’s more important to get started than to pick the perfect
tools, and you can have a very simple technical stack (bestselling
author Ryan Holiday literally started with Gmail).

As you grow, you’ll need more powerful tools. Before we get into the
specifics for each stage/tool, let’s talk about general considerations
any time you’re adding something to your tech stack…
Key Considerations for Any Tool
At each stage, your main goal is to make sure your technology strikes a
balance between being powerful enough to grow with you, and simple
enough that it doesn’t slow you down.

Broadly speaking, you want to consider:

● Price: How will the cost of using the tool change as your list
grows?
● Compatibility: Will a new tool work well with the rest of your
existing tech stack?
● Flexibility: Can you modify it to suit all of your particular needs?
● Popularity: More popular tools typically have more robust
documentation/support.
● Longevity: Is the maker of the tool well-established? Will they be Pro tip: Nontechnical people on your team
here in the long term? should be able to do as much as possible
without needing help from developers.
Last, you’ll always want to consider how a tool helps you move toward
the business that you’re trying to build. An all-in-one platform might be
convenient, but it’s only a good choice if it helps you monetize and grow
the way you want to.
All-In-One Solutions
These days, more and more platforms (like Substack, Mailchimp, and Revue) offer an all-in-one suite of tools that can serve all
the basic needs of a newsletter company.

Substack, for instance, gives every creator a website where they can publish articles and capture new signups. It handles
subscriber registration, content paywalling and billing, offers tools for building and sending emails, and analyzes key
engagement metrics.
An all-in-one platform simplifies your technical
stack…

…but there’s a price for the convenience, and it comes


in the form of:

● Cost: Substack makes money by charging a


10% fee on all subscription revenue. As the
chart to the left shows, those costs add up as
your list grows.

● Customizability: Want a custom feature? It’s


not always possible. All-in-one platforms are
designed to suit the needs of the many.

● Platform dependence: Finally, there’s a risk to


relying on a single company for too much.

14
When Jacob Donnelly of A Media Operator moved his newsletter
off Substack, it was because his business was maturing. He
realized leaving would help him:

Segment his lists better — He found he needed better tools


for offering different things to different subscribers.

Add features to his website — He wanted to create new


resources, like product guides, a contact page, and a
consulting page, but didn’t have enough control over his
website to do it the way he wanted.

Add new revenue streams — Companies wanted to buy


bulk subscriptions, but Substack didn’t offer the
functionality he wanted. Changing to his own platform
opened up new revenue streams, and allowed him to create
a better experience for clients.

Still, all-in-one platforms can be a great place to start because they


get you up and running quickly.
Custom Build

At the other end of the spectrum are tools that you build
yourself, or that you have custom-built for you.

This could range from something small, like a custom


spreadsheet for tracking your advertisers, to something
more complex, like a full-featured app or web platform
you build to manage some aspect of your business.

The New York Times, for example, built its own custom
email service provider (ESP), which powers its
newsletters, drip campaigns, and automated breaking
news alerts, sending nearly 4B emails per year.

Morning Brew’s world-class referral system is a custom


build, as is the tool they use to manage ads in their
newsletters.
Tyler Denk the first technical hire at Morning Brew told us that when
given the choice, he always preferred to build custom, since it gave them
the flexibility to design for their team’s specific needs. It also allowed them
to not be dependent on another company to add features they wanted.

But building custom tools comes with its own trade-offs and demands:

● Expertise: Building custom tools requires technical knowledge. If


you don’t have that, it means you need to hire and manage
engineers.

● Money: Building an email platform from scratch can cost more


than several years’ subscription to an all-in-one service.

● Time: A custom tool needs to be maintained over time, with fixes


and updates to match your evolving needs. This can detract from
other projects.

Click To Hear More From Tyler

17
02. The Newsletter Tech Stack

Regardless of whether you start with an all-in-one


platform or some other tool, as your company
grows, you will inevitably incorporate several
different tools into your processes.

Let’s take a look at some of the best options for


each individual layer of the typical newsletter stack.
Website
Your website has two key functions. It serves as:

● A place for people to find and sign up for your


newsletter.

● A place to store past content (free or


paywalled), which helps convince people to
subscribe to your newsletter.

The easiest way to build a publication online is to use


something called a content management system
(CMS). These are tools that allow you to build a
website and publish articles without needing to know
how to code.

There are lots of CMSes on the market, and the major


trade-offs between them come in the form of cost,
customizability (simpler tools offer less), and the level
of technical skill needed to create a finished product.
Tech Recommendation

Sitting neatly in the middle of the spectrum with a


nice balance of simplicity and power is a tool
called WordPress. WordPress is the most popular
CMS on the internet, and currently powers ~43%
of all the websites in the world.

It’s one of the best tools for publishing, and is


used by huge companies like The New York
Times as well as small upstarts like A Media
Operator.

What’s more, HubSpot’s WordPress plugin is free


to use and lets you take advantage of HubSpot’s
tools right within the functionality of your
WordPress installation. With the plugin, you can
capture, organize and engage web visitors with
free forms, live chat, CRM, email marketing, and
analytics.

20
Wordpress Benefits

You can build an entire website, publish articles, and even sell products all without knowing any code. And yet, the platform is
extremely developer-friendly, which means that if you ever need/want to, you can code custom features. With just a few minutes’
Simple Yet Powerful training, your writers will easily be able to upload articles to the website on their own, and when it’s time, your growth team will be able
to make and test landing pages with no technical help.

WordPress has a suite of plugins that easily connect your site to other tools (like your email platform, billing service, or analytics
software), allowing you to do more. For instance, if you use HubSpot to manage your list, WordPress has a plugin that connects your
website to your HubSpot account so you can easily add sign-up forms to different parts of your site. Some that we use include:

Highly Extensible ● Elementor for building landing pages quickly


● CookieYes GDPR Cookie Consent for managing privacy among European readers
● Hotjar for traffic analytics
● Yoast SEO for crucial SEO insights on pages and posts

If you decide you want technical help (now or in the future), it’s easy to find developers who have worked on lots of WordPress
Extremely Popular projects in the past.

WordPress comes in two varieties: WordPress.org, and WordPress.com. The difference between them is that:

WordPress.org is free — you download the WordPress files, upload them on your site, and never have to pay for the CMS. This requires
a little technical know-how, since you will need to install WordPress on your site yourself. WordPress.com charges a monthly fee and
Free handles the setup and hosting for you.

Of the two, we recommend using the WordPress.org option, since it offers far more functionality at no cost aside from whatever you
pay for hosting.

21
Drawback — Speed:

WordPress sites load a little slower than other


websites.

However, it’s not enough to counter the benefits the


framework provides, and with a little work, you can
mitigate any harm to your search engine rankings or
user experience.

22
Registration Software
If you run a paid newsletter, registration software is one
of the most important parts of your business. It serves as
your paywall, letting subscribers see your content while
keeping the rest of the world out.

You only need a registration platform if you’re planning to


charge for content, so free newsletters can skip this.

Your registration system ties into your email platform,


keeping your lists up to date; it also lets your subscribers
manage their billing information or cancel their
subscription.

Some platforms like Substack come with registration


software built in. But there are also stand-alone options
available, like Piano, Pico, and WooCommerce.
Tech Recommendation
Second, people are always trying to get around
paywalls — the more popular the registration software
Recommending registration software is tricky.
is, the more likely it is that hackers have found (and
To begin with, the concept of a paid newsletter is still published) a way around it.
relatively new, and there aren’t many registration platforms
that have been specifically designed for this purpose yet. For example, one of the most popular registration
software programs is called Piano. It’s used by media
giants like CNBC, The Wall Street Journal, TechCrunch,
and others.

A lot of people would obviously like to read those


websites for free.

This browser plugin was designed to circumvent


Piano, along with two other popular paywalls, so that
users could do so. It’s a great example of why paywalls
can sometimes fail you.
If you have the resources to build your own custom paywall…
… then we recommend doing that, especially if you’ve
outgrown a service like Substack.

Creating custom paywalls is rare and shouldn’t be your go-to


if you’re just starting out. But if your business is big enough,
and you really care about locking your content down, then
seriously consider having your own paywall built from
scratch.

The New York Times’ paywall, for example, handles 30m+


user requests every day, so they built their own. Here’s a
story from their lead software engineer on how they
relaunched their paywall without interrupting service.
Otherwise, look at Pico…

Pico is a relatively new registration software used by


local newsrooms all over the US, as well as
newsletters like Wait But Why and A Media Operator.

It was designed specifically for content creators, can


be installed easily, and offers a suite of tools that
make it possible to add and bill subscribers directly
on your site.

26
Benefit No. 1 — Flexible Business Models

As your newsletter grows, you may want to add more


products, like e-books or consulting packages. Pico
makes this possible.

Benefit No. 2 — Easy Integration

Pico is easy to install on WordPress, Wix, and


Squarespace CMSes. There’s also a custom API, so
you can install it on your website even if you’re not
using a CMS.

Benefit No. 3 — Keeps Users Logged In

Pico is able to keep subscribers logged in to your site


so that they have easy access to content when they
visit. It also offers a login compatible with social
networks, so people can stay connected via their
Facebook or Google accounts.

27
Tips Regardless of Your Choice:

Heed the advice of CX: Remember that the people who will
interact most with your registration software will probably be
your CX team. Have them help pick the software, and choose a
system that ties into their workflow.

Consider group subscriptions: If you write a business newsletter,


companies may want to buy subscriptions for groups of
employees. It helps if you pick registration software that makes
this easy.

Get clear on pricing: Registration software often charges a


recurring subscription fee and/or a percentage of monthly
revenue. Some (like WooCommerce) require paid add-ons in
order to work. Get a clear idea of what your costs will be based
on your list size before you sign up.

28
Payment Processor
Credit card info is like toxic waste — you really don’t want to be the
one responsible for touching it.

Most small businesses simply don’t have enough security to handle


credit card data well, and if you take someone’s info, and that info
gets stolen, you can be on the hook for negligence.

That’s why you use a payment processor.

Payment processors build tools that integrate into your website,


allowing you to charge customers without ever actually storing their
credit card info.

They act as a middleman, taking payment info from subscribers


and sending money to you in exchange for a small fee.

All of the data is handled by the payment processor, while


customers get a nice, simple checkout and can pay with their
preferred method.
The two big players are Stripe and Braintree Tech Recommendation

The biggest difference between them: Braintree is the only Competition is so fierce between Stripe and Braintree that
one that offers PayPal as a checkout method (because they most of their features are almost indistinguishable. At the
own it). time of writing, they were both easy to set up and had the
same pricing structure.

So, it really comes down to two things:

1. Do your readers want to use PayPal?


We found that a good chunk of our readers like using
PayPal (~20%). If the same is true for you, then consider
Braintree. It’s possible to use both side by side, but if you’re
just starting out, you’re likely better off picking one or the
other.

2. Will Braintree play well with the rest of your tech stack?
Some tools, like Pico, only work with Stripe for now, so that
can make the decision easier.
Tips Regardless of Your Choice:

Payment processors typically charge a flat fee per transaction,


plus a percent of each transaction. For example, at the time of
writing, Braintree and Stripe both charged:

$ $0.30 cents per transaction + 2.9%


$
$

$
$
Most billing platforms tack on extra fees for things like:

● International transactions with overseas customers


$ $
● Currency conversions
● Chargebacks or rejected transactions

So when making your choice, think about your audience, where


they’re located, and whether the price you’re charging is high
enough to handle the extra fees.

31
Email Service Provider (ESP)
Your email service provider (ESP) is the tool you use
to package and ship your emails.

You will switch ESPs a few times as you grow your


business.

In order to understand why, you need to understand


a crucial concept: deliverability.
A Primer on Deliverability ISPs are always on the lookout for spam

Deliverability is the percentage of the emails you send that Anything that even seems like spam is sent to the spam folder
actually make it to the inbox of your intended recipients. rather than being delivered, and your “deliverability” goes down.

One of the biggest factors behind whether your email gets


When you send an email, it’s not like handing someone a
delivered is something called your “sender reputation,” which is
note — it doesn’t just go straight from you to them.
impacted by things like:

There are lots of computers in between that collect, check, ● The number of emails you send
and route your message so that it gets to the right place. ● How many are opened
● How many are reported as spam
It’s more like sending a letter: you write it, pack it, then bring ● … and more
it to a post office where they organize your letter along with
many others and coordinate shipping them around the
world.

When it comes to email, internet service providers (ISPs)


like Google or Comcast are like the postal service. There’s
one major difference though: the post office will deliver
anything, as long as it’s paid for — ISPs will not.
Early on, you won’t need to worry much about deliverability.

But as your email list grows, you’ll need better and better tools in
order to manage your sender reputation and avoid the spam trap.

For example:

● Dedicated IP Address — Your IP address is like the house


you ship your letters from. If you’re using something like
Substack or Mailchimp, you’re likely sharing an IP address
with many other senders. If any of them are malicious, it
can affect your sender score.

● SPF, DMARC, DKIM — These are security protocols that


help ISPs prove an email came from you, and isn’t a
phishing attack or other malicious message. They’re
complicated to set up, and you don’t need to worry about
them early on, but they’re a must-have as your list grows.
A more powerful ESP will also help you manage ‘list hygiene’...

… which is the process of removing or “scrubbing” inactive readers


from your list.

List hygiene is a crucial part of your success as a newsletter business.


Inactive readers damage your sender score by lowering your open rate.
They also may not want to hear from you.

“I think the most difficult thing to accomplish at scale is maintaining a


super clean email list of engaged subscribers,” Morning Brew’s Tyler
Denk told Campaign Monitor in a 2018 interview.

“When you only have a few subscribers, it’s relatively easy to manage
them,” he said. “However, as you grow, you constantly have to assess
who’s engaged, who’s not, and which email addresses belong to real
people.”

The key to list hygiene is:

● Identifying inactive readers


● Nudging them to see if you can reactivate them
● Removing them from the list if they remain inactive
Here are a few list hygiene best practices, straight from The Hustle’s
former general manager and head of growth, Scott Nixon:

1. Segment your list by who opens and who doesn’t. Can an 2. Identify the people who used to open, then stopped.
automated (but well-timed and well-written) nudge win the Maybe they need a different message to bring them back.
non-openers back?

3. Be careful with your nudges. Some email clients will 4. Know exactly how your readers consume your
block the tracking pixel that tells your email service provider newsletter. Related to the previous point: If 3% of your
whether a reader is opening your newsletter. You might readers use a platform that blocks tracking pixels (the email
think a reader isn’t opening, but they are — you just can’t see service Hey promotes pixel-blocking as a selling point),
it. That’s a good reason to keep a close eye on any you’ll need to think through how you serve them.
reengagement campaigns.
Another reason list hygiene is crucial is that it affects
your audience data and your understanding of where
you find high-quality readers.

If you find that you’re acquiring really inexpensive


subscribers from some source, but they all go
inactive after a month and end up getting removed,
then it doesn’t really matter how little you paid for
them — it was wasted money.

By keeping your list clean, you’re left with an


engaged audience and high-quality growth data,
which helps you now and into the future.

With that in mind, let’s take a look at how your ESP


needs will evolve over time, and discuss some of the
key considerations you should be making at each
stage.

37
Historically, many people have gone with Mailchimp,
Early Phase (~0-100k emails per day)
because it’s easy to use and free to get started. But if you’re
serious about turning your newsletter into a business
At this stage, the most important thing is to find early
(rather than just a hobby), you should consider starting with
product-audience fit and to send consistently. You don’t need
HubSpot. Here’s why:
to optimize your tech stack, almost anything will work.

Pick whatever all-in-one newsletter tool looks cheapest and First, it’s got many of the same features that make
easiest to use… Mailchimp great for beginners, including:

… and focus all of your energy on writing. At this early stage, ● A free starter plan
the most important thing is finding your audience, not your ● An easy-to-use drag-and-drop newsletter builder
ESP. Pick one, and get started. ● Seamless integration into your WordPress site and
other business apps

But beyond that, because our email platform ties into our
other sales, service, and operations products, HubSpot will
grow with your newsletter business in ways that other ESPs
simply can’t.

Bonus: HubSpot’s payments tool makes it easy to manage


subscriptions, with lower fees than most alternatives.
Growth Phase (~100k-1m emails per day) Over the following few months, Denk was able to help them
drive improvement in several key metrics:
When you reach this point, it’s typically time to make your
first technical hire and focus on improving your deliverability. ● Open rates jumped from 20% to 47% within eight
At this scale, even small decreases in deliverability will months
translate to significant loss of revenue. Two important steps ● Click-through rates of 15% for their daily newsletters
to consider at this stage: ● Their deliverability rate climbed to 99% (up from ~60%
with Mailchimp)
● Get your own dedicated IP address, which helps ● Gmail moved their newsletters from the “promotional”
protect your sender score. tab to subscribers’ inboxes
● Set up your SPF, DKIM, and DMARC, which help
authenticate your email. “In order to get these results, we ran re-engagement
You can get help with both of these from your ESPs customer campaigns to identify unengaged users and churned around
service team. Because your ESP is so important to the 100k of them in order to increase [our] aggregate open rates
success of your business at this stage and beyond, be sure and improve mailbox rankings,” Denk told Campaign Monitor.
to pick one with excellent customer service.
“We also migrated to a new sending domain and moved from
As an example, Morning Brew made their first technical hire, a shared IP to a dedicated IP to improve our domain
Tyler Denk, at this stage. They also switched ESPs from reputation and deliverability. Additionally, in our Welcome
Mailchimp to Campaign Monitor. Series, we asked subscribers to add Morning Brew to their
personal contacts to increase visibility in the inbox.”
Mature Phase (~1m+ emails per day)

By the time you’re sending ~1m+ emails per day, you’re


running a comprehensive business, and likely have several
employees. The main purpose, and challenge, of tech at this
stage is making sure all your teams are able to work
cohesively.

You will likely have a technical person helping you choose


your tools, so we won’t go deep here. But it’s worth noting
that by this stage you’ll probably be using a blend of custom
in-house tools and third-party software.

Tips Regardless of Your Choice:

Make sure your ESP has great customer service and is


willing to walk you through the setup live.

If you switch from one ESP to another, do it gradually. Move


your list over bit by bit until you’re sure everything is working
in the new ESP before finally getting rid of the old one.
Analytics

We’ll talk about specific things you should be


tracking in later sections of this guide. For now,
let’s talk about analytics in a broad sense.

In the newsletter business, there are three main


things you want to be collecting data on:

● The performance of your marketing


channels and website
● How readers interact with the newsletter
once it hits their inbox (opens, clicks, etc)
● The company’s financial performance

Within each of these broad categories, there are


different key performance indicators (KPIs) that
can tell you important things about your business.
Most of the tools in your stack will offer built-in analytics These days, the biggest challenge isn’t getting data but
of some kind: filtering it — choosing what to pay attention to, and what to
ignore.
● Most website platforms spit out basic analytics.
● Your ESP tracks who interacts with your email. You need a “North Star”
● Your billing software offer data on revenue, churn,
or failed payments. A North Star is the single most important metric that you
pay attention to above all else.

You will track many things as a newsletter business, but


your biggest decisions should revolve around your North
Star.

You can use any analytics platform you choose as long as it


allows you to easily and accurately keep track of your North
Star.
Tech Recommendation

Pick your North Star wisely. Your team will be incentivized to grow that
number, and if you have them focused on the wrong thing, it can end up
causing problems.

For example, some people incorrectly set their list size as the North Star,
focusing all of their efforts on growing it without paying attention to
whether they’re adding quality subscribers.

This is crucial because, as we’ll discuss in the monetization chapter, it


doesn’t matter whether you’ve got a free or paid newsletter — you only
make money from engaged readers who like your stuff.

Your North Star needs to be a single metric that gets at the heart of two
things:

● How happy and engaged readers are


● Whether or not revenue is growing

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For ad-supported newsletters…

… the North Star should be unique open rate (UOR) — the


percentage of unique recipients on your list who opened your
email once.

Most ESPs will tell you what your unique open rate is.

UOR is directly tied to the satisfaction of your readers and the


health of your business, since ad-supported newsletters typically
charge based on opens.

If you have a high unique open rate, it means people like your
content, and you can charge advertisers more. Conversely, if you
have a huge list but a low unique open rate, your list is full of
people who don’t look forward to reading your stuff.

For paid subscriptions…

… your North Star is renewal rates — the percentage of people who


keep their subscription.
Remember, more is not necessarily better: Data is only useful if it helps you
make good decisions. Use tools that give you what you need without
overwhelming you with too much information.

Data literacy: It’s important that anyone on your team who’s using data has at
least a basic understanding of how it works, and how it can and can’t be
used. Some great, easy-to-read books to improve your data literacy include:

1. Bad Science: By dissecting misleading headlines and 2. How Not to Be Wrong: If you don’t consider yourself a
“scientific” reports, Goldacre shows you how to think more “math person,” this is a great, wide-ranging introduction to
clearly about data and avoid being misled by statistics. the ways math has been used to solve real-world problems
with less-than-obvious causes.

3. Fooled by Randomness: One of the greatest challenges 4. Reforge: Reforge is an online education platform focused
people run into with data is confusing correlation and on helping growth and product managers build better
causation. In this book, Taleb shows you how to avoid being startups. Its courses are full of case studies that will show
fooled by seemingly related events that are, in fact, you firsthand how to understand users, build growth loops,
completely random. and analyze what your data is really telling you. (Cannot
recommend highly enough.)
There’s no single answer for how to build a newsletter company. As the stacks below show, the tools you use will be unique to
your needs. But some combinations are more popular than others:

Newsletter Website Registration Billing ESP Analytics

The New York Times

N/A N/A
Morning Brew (Free Newsletter) (Free Newsletter)

N/A N/A
The Newsette (Free Newsletter) (Free Newsletter)

A Media Operator

Petition

N/A N/A
The Hustle (Free Newsletter) (Free Newsletter)
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