Chapter 2 - Technology
Chapter 2 - Technology
7-Figure Newsletters
PART TWO: TECHNOLOGY.
So you want to build a newsletter biz?
Great. You’ve come to the right place.
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:
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).
Instead, you NEED to know how the business model works; How
all the pieces fit together.
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.
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’re actually going to go a little deeper than that — touching on the five
key areas that technology serves inside your business:
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.
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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.
… 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:
● 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 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.
● 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…
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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:
At the other end of the spectrum are tools that you build
yourself, or that you have custom-built for you.
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.
But building custom tools comes with its own trade-offs and demands:
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02. The Newsletter Tech Stack
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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:
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.
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Drawback — Speed:
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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.
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Benefit No. 1 — Flexible Business Models
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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.
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Payment Processor
Credit card info is like toxic waste — you really don’t want to be the
one responsible for touching it.
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.
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:
$
$
Most billing platforms tack on extra fees for things like:
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Email Service Provider (ESP)
Your email service provider (ESP) is the tool you use
to package and ship your emails.
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.
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.
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:
“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.”
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.
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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.
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.
Your North Star needs to be a single metric that gets at the heart of two
things:
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For ad-supported newsletters…
Most ESPs will tell you what your unique open rate is.
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.
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:
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)
Here’s a sneak peek of our weekly newsletter 👀
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