The Ultimate Guide To Starting A Newsletter

Dickie Bush and Nicolas Cole

Ultimate Guide Table of Contents

In this week's Digital Writing Compass Deep Dive, we want to talk about newsletters.

Specifically: if you want to start a newsletter, which type of newsletter you should start (and the pros and cons of each).

The Benefits Of Starting A Newsletter

At some point in every Digital Writer’s journey, the subject of “starting a newsletter” comes up.

  • You have built you daily writing habit, and gotten in a cadence of Practicing In Public…
  • You’ve started building an audience…
  • You’ve begun gathering data of “what works” for that audience (topics, formats, etc.)…
  • Your library of content is growing…
  • You are accumulating attention on your work on social platforms…

Now, you decide, it’s time to launch a newsletter!

For a few big reasons:

  1. A newsletter will help you shift from a “rented” audience on social platforms to an “owned” audience (by capturing people’s emails and being able to communicate with them directly).
  2. A newsletter will deepen the relationship you have with your readers, giving your loyal subscribers “more” value than you might otherwise share on social media.
  3. A newsletter is the natural progression from shorter-form content (Tweets, Threads, LinkedIn posts, even Medium articles and Quora answers) to longer-form content.

Hence why nearly every Digital Writer & Creator, at some point along their journey, feels the need to start a newsletter.

The question is: what kind?

The Myths Of Starting A Newsletter

The unfortunate truth is that most newsletters fail.

Anyone can “start” a newsletter, but how many newsletters do you subscribe to and then unsubscribe from a few weeks (or days, or hours) later?

How many newsletters do you actually read on a daily or weekly basis?

How many newsletters add true value to your life versus just being longer versions of the same things you already read on social media?

Here are some myths to keep in mind:

  • “If you have a newsletter, people will subscribe.” Wrong. Just because you have a newsletter doesn’t automatically mean people are going to subscribe to it (regardless of how big your social media following is). What matters is the offer (the promise) you are making to subscribers—hence why big companies that say, “Subscribe to our newsletter!” on their websites but have no real “offer” for readers have such terrible opt-in and retention rates.
  • “A newsletter can just be repurposed content.” Yes, but mostly no. If your daily, weekly, or monthly newsletters is just a copy/paste of the same content you share on social media, your most loyal readers aren’t going to open your newsletters and say, “Wow! This is amazing!” They’re going to open your first few newsletters, say, “Wow, you cheap scumbag,” and then immediately unsubscribe. Your newsletter can repurpose content, but it should not be 100% repurposed content.
  • “People don’t read newsletters unless…”. Fill in the blank with whatever you want: unless they’re short. Unless they’re long. Unless they have pictures. Unless they get sent at 2:47 p.m. on Tuesdays. People have been saying newsletters (and more specifically: certain types of newsletters) have been saturated and “no longer popular” for 20 years. Seriously. And yet, every single day, newsletters continue to prove themselves to be a perfectly viable (and still growing) category.

So, how do you make yours stand out?

More importantly, how do you make your newsletter worth reading?

The Newsletter Fork In The Road: Which Direction Do You Want To Go?

To cut to the chase: there are only 2 types of newsletters that “work.”

  • Short & Curated: Newsletters in a fast-moving category that compress a ton of information on a specific subject into a quick read.
  • Long & Original Thinking: Newsletters in a dense, thoughtful category that provide in-depth insight, analysis, and unique information on a specific subject.

Everything else falls into “Hey! Subscribe to my fun newsletter where I share my learnings along the way!” territory.

And, to be blunt: nobody reads these.

(If your newsletter is you just “sharing your journey,” shut it down.)

The best newsletters, the ones that accumulate tens or hundreds of thousands of subscribers, are not “newsletters.” Don’t think of them like that. Think of them as niche news stations. Prime-time TV channels. Books. Even an entire course—with the information slowly explained week after week, opposed to all at once. The best newsletters either save you 1,000 hours of annoying work “finding” everything you’re looking for, or save you 1,000 hours of trial and error by accelerating your knowledge in a particular category. Everything else, you give your attention to for a few weeks and then hit unsubscribe.

Because what it’s offering you isn’t “worth it.”

So that you can consciously choose which direction is best for you, let’s breakdown each one:

Short & Curated Newsletters

Short, curated newsletters have 1 core benefit: to save you time.

Here are some examples:

  • Morning Brew: “Become smarter in just 5 minutes.”
  • The Hustle: “Get the 5-minute newsletter keeping 2M+ innovators in the loop.”
  • Robinhood Snacks: “The 3-minute newsletter with fresh takes on the financial news you need to start your day.”

Notice anything in common?

All of these newsletters (and thousands more just like them) make the same exact promise: “In exchange for your email, we’ll go out and spend hours finding all the relevant information you need to know about [topic] and compress it down for you into a 5 minute-or-less read.” Which means, what you’re “buying” with your attention is “time saved.” (You could spend 2 hours reading The Wall Street Journal every morning—or you could just subscribe to Robinhood Snacks and skim the important stuff in 3 minutes.)

Since these types of newsletters leverage curation (and are constantly looking for the “next thing” to find & present to you to be “worth it”), they tend to work best in fast-moving “newsy” categories:

  • Stocks
  • Politics
  • Sports
  • Music
  • Pop Culture
  • Trending Topics
  • Etc.

As a result, most of these types of newsletters are free (because all they’re really doing is organizing content that already exists elsewhere), meaning they can only monetize in one way: ads.

They are playing a volume game.

So, when should you start a Short & Curated newsletter?

  1. You are writing in a fast-moving, “newsy” category (where there is no shortage of new things to curate).
  2. You are writing in a giant, non-niche category (personal development, money, politics, pop culture, etc.).
  3. You are not ready to start sharing your own original thinking yet (and curation is an easier place to start).

Long & Original Thinking Newsletters

Long, original newsletters have 1 core benefit: to accelerate your expertise.

Here are some examples:

  • Category Pirates: “The authority on Category Creation and Category Design.”
  • Stratechery: “Stratechery provides analysis of the strategy and business side of technology and media, and the impact of technology on society.”
  • The Generalist: “Every Sunday, we send you a free email unpacking one of the most important companies in tech and crypto. You’ll understand how these businesses work, why they matter, and what it means for you.”

Notice anything in common?

All of these newsletters (and many more just like them) take one specific category, niche, or vertical, and promise readers to go “in depth.” These newsletters are not about “staying in-the-know” in 5 minutes or less. These newsletters are smart. They ask readers to pay attention, stay engaged, and think. You don’t skim these newsletters. When they hit your inbox, you pour yourself a cup of coffee (or a bourbon on the rocks), dim the lights, and read—with the goal of finishing the piece and knowing exponentially more about a subject than when you began.

Since these types of newsletters leverage original thinking, they tend to work best in slow-moving niches through a lens of:

  • Analysis
  • Strategy
  • History
  • Psychology

As a result, these types of newsletters are less “popular” than their Shorter, Curated counterparts, and typically grow slower—but are immensely more valuable. These are the types of newsletters readers build their weekly schedule around (making sure they have time to read every single issue). These are the types of newsletters that can easily become paid newsletters (because readers find them so specific, and so valuable). And these types of newsletters have exponentially lower churn.

Because they are playing a quality game, not a quantity game.

So, when should you start a Long & Original Thinking newsletter?

  1. You are writing in a slower-moving category (writing is a great example—not a lot “changes” in the writing world on a day-to-day basis, making it difficult to have a compelling Short & Curated “newsy” writing newsletter).
  2. You are writing in an oddly specific niche (like teaching first-time homeowners how to save money by fixing doors, windows, sinks, bathtubs, and more, all on their own).
  3. You have deep domain expertise (making your opinions, insights, and perspectives incredibly valuable to the right kind of reader).

The Digital Writing Compass: Case Study

Can you tell which one we are?

Not a lot happens in the “writing world” on a day-to-day basis. It’s not like writing styles change with the speed of stock tickers. Similarly, if you truly want to become a better writer, which is more helpful? A bunch of curated links every week with captions like: “You’ll love this!” Or deep walkthrough guides that help you improve at individual skills, week after week?

Our newsletter, The Digital Writing Compass, is a Long & Original Thinking newsletter.

  • We are writing in a slower-moving category (writing advice).
  • We are writing in an oddly specific niche (Digital Writing, writing on Twitter, writing on LinkedIn, writing a newsletter, etc.)
  • We have deep domain expertise in the Digital Writing world.

As a result, we have grown our newsletter from 0 to over 35,000 subscribers in less than a year.

And we have minimal churn.

Now, is our newsletter smaller than other more “popular” Short & Curated newsletters? Of course. But that’s fine—because we don’t need 2 million subscribers. We just need to keep attracting readers who read each newsletter and think, “Wow, if this is how valuable their free newsletter is, then their course must be insane”—prompting them to eventually join a cohort of Ship 30 for 30.

Launching A Newsletter Of Your Own

So, here’s where you need to be brutally honest with yourself.

If you want to start a newsletter, the first big question is: Do you have deep domain expertise in a niche?

  • If Yes, you should start a Long & Original Thinking newsletter. And, you should work hard to make every issue of your newsletter feel like readers are getting a chapter from a book, or a free module from your most expensive course, for free. Get deep.
  • If No, you should start a Short & Curated newsletter. And, realize that you are playing a volume game—which means your “measure for success” is how much time you can save your readers. Don’t just slap 3 links into a newsletter and call it a day. The only reason anyone is going to subscribe to your Short & Curated newsletter is if what you’re curating is truly “worth it.”

And if neither of the above feel like what you want to do, then here’s our recommendation:

Don’t start a newsletter.

Because writing, growing, and maintaining a newsletter & an active newsletter list takes work. And unless you know exactly what value you are providing readers, your time is better off spent elsewhere.

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