A Quick Guide To Starting A Newsletter And Getting Your First 1,000 Subscribers (In 3 Simple Steps)

Dickie Bush & Nicolas Cole

Ultimate Guide Table of Contents

This Deep Dive is all about how to start a newsletter:

  • Choosing the right newsletter platform (there are a lot of options out there these days!)
  • Deciding whether you should build a free newsletter or try to go paid
  • And the best platforms to drive traffic & get your first 1,000 subscribers

“I want to start a newsletter. What should I do?”

This is one of the most-common questions we get asked.

So, we want to give you a crash-course on how newsletters work—as well as help you filter through some of the noise so you can get started quickly.


Before we dive in, we want to point something “meta” out to you.

As a subscriber to our own newsletter here, what you are expecting is information that helps you move forward as a digital writer & creator. Which means our job is to work HARD to figure out:

  • What questions you have
  • What topics you’re most interested in
  • What walkthrough guides you would find most valuable
  • What problems you are struggling to find non-obvious solutions to
  • And what outcomes you want to unlock (for yourself and your business)

This guide on how to start a newsletter is a great example of us listening to what questions readers (like you) are asking, and then creating content that answers those questions.

This is the big secret to building a successful newsletter.

You don’t have to be “brilliant.”

You just have to be clear about who your target reader is, and then listen to what questions that person has—and answer them.

And with that...

Let’s dive in!

Step 1: Choosing the right newsletter platform:

There are 3 options you have to choose from.

  • Substack: For casual creators
  • Beehiiv: For advanced/marketing-minded creators
  • ConvertKit: For expert-level business-minded creators

Here's a quick rundown of each one:

Substack: If all you want to do is write & publish, Substack is your best bet.

  • Easy setup
  • Simple interface
  • No complicated features

The pros of Substack are that you can get setup & publishing quickly.

The cons are that you don't have much visibility into analytics.

Beehiiv: If you want a bit more visibility into analytics & control over how you engage with readers, you'll need something more advanced. On Beehiiv you can:

  • Integrate a referral program
  • Gather audience data
  • Segment audiences
  • And more

ConvertKit: Finally, if you want to be very entrepreneurial as a creator (and turn your writing into a business), ConvertKit is the most robust newsletter platform.

  • Full audience segmentation control
  • Flexible workflows & automations
  • Create landing pages & forms
  • Etc.

While there are tons of other email/newsletter platforms—Revue, Mailchimp, etc.—the above 3 are the ones that are most creator friendly and also the ones pushing innovation the most right now (which means they are likely going to continue to attract more and more creators, and be around for a long time). So, if all you want is a tool to “hit publish,” go Substack. If you want more flexibility and tools to play with, go Beehiiv. And if you want to use email to build an entire business, go ConvertKit.

Step 2: Free vs Paid

Depending on how "entrepreneurial" you want to be (choosing your platform), you then need to decide if this is a free newsletter or a paid newsletter.

  • Free = value first, monetize later
  • Paid = value is clear first & readers are willing to pay

The whole purpose of a free newsletter is to engage your social readers further, expand "what works" into more valuable content, and sell digital products to them (later). For example: you are subscribed to our Ship 30 for 30 free newsletter right now! To keep you “engaged,” our job is to deliver so much valuable content (that we could have, or should have charged for, but decided to give to you “for free” instead) that when we pitch you on joining Ship 30 for 30 later, you’re excited to hop aboard. As a result, we don’t “make money” from readers being on this email list. We make money when a percentage of readers go from being free readers to paying students inside our Ship 30 for 30 course.

The purpose of a paid newsletter is sort of the opposite, and is better suited for writers who already have existing, engaged audiences elsewhere and want to “upsell” those readers on even more valuable content (for example: Captain Cole has a paid newsletter called Category Pirates ($20/month or $200 per year). Think of your paid newsletter as an evergreen eBook. It’s your entry-level product. Which means in order for people to want to buy access to your “evergreen eBook”/newsletter, you need to a) already know what content your readers find most valuable and would be willing to pay for, b) and have a distribution flywheel (Twitter/LinkedIn/etc.) introducing new readers to your work. If you don’t have these two things, running a paid newsletter is likely not going to be worth the effort.

Of all the ways to make money as a writer, monetizing via a paid newsletter is one of the hardest (and longest) paths to success.

It’s much easier to build a free email list and then make money selling digital products like eBooks, books, courses, and even services to your engaged readers.

Step 3: Leveraging social platforms to drive your first 1,000 subscribers.

Newsletters themselves have no viral loops.

We don’t consider Substack or Beehiiv or ConvertKit as “digital writing” platforms because there isn’t any way for your content to spread into other ecosystems in any sort of reliable way (yet). Which means, in addition to building a newsletter, you need to actively write & publish in social environments—introducing new readers to your newsletter.

The 2 best platforms to drive traffic to your newsletter and/or suite of digital products today are:

  • Twitter
  • LinkedIn

Here's why these 2 are the best:

Twitter does an amazing job at recommending the right content to the right people. If you can build a small, engaged audience on Twitter, there's no reason why all those same people shouldn't be on your email list.

  • Tweet
  • Link to newsletter
  • Repeat

The other best social engine right now is LinkedIn. It's like Corporate TikTok.

  • People are bored at work & want to read
  • People want to stay "in the know" on valuable content
  • There's a shortage of smart content on LinkedIn
  • And hundreds of millions of users

The key to driving newsletter subscribers is to think of your newsletter as the expanded, more valuable version of all your social content.

  • If you write a thread about how to create high-converting landing pages, how can you write an email that is The Ultimate Guide To Creating High-Converting Landing Pages.
  • If you write an Atomic Essay about 7 things you need to have in your morning routine, how can you write an email that is 7 Things You Need In Your Morning routine—expanded with stories, examples, and actionable frameworks.
  • If you write a LinkedIn post about business books you should read, how can you write an email that gives even more resources for readers to dig into: podcasts to listen to, YouTube interviews to watch, etc.

Your newsletter (free or paid) doesn’t need to be 100% net-new content.

It can be the same content/ideas but expanded and with more depth, stories, examples, action steps, and templates.

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