Hello friends,

I recorded a handful of conversations with some of my favorite writers earlier this year and excited to share them with you.

We’re calling this little experiment Rough Draft and our goal is to provide listeners with a mix of inspiration, motivation, and guidance.

Our first episode is with the one and only Doomberg, the #1 Finance publication on Substack.

You should begin with what you love to do that doesn't feel like work and then eliminate everything else from your life and wonderful things just magically happen.

Doomberg stands out for its intentional approach to their newsletter, with deep thought given to their audience, branding, marketing, editorial, pricing, paywalling, and every other aspect of building a successful paid newsletter.

The conversation is full of valuable insights and lessons from Doomberg’s journey. Below are a few of the major topics and takeaways I’ve continued to chew on after our conversation.

Check out the full episode on Apple Podcasts, Spotify, and YouTube.

Ideal customer profile

Before launch, the Doomberg team invested a lot of energy into nailing their ideal customer profile (“ICP”) — the types of people that would ultimately pay for Doomberg. They wrote a handful of character sketches, which were detailed descriptions of fictional people answering questions like:

• Where do they work?

• How much are they worth?

• How many cars do they have?

• What’s a hypothetical day they go through?

Equipped with a better understanding of their specific target customers, they were able to make important decisions including:

• Charging a premium price for Doomberg and avoiding discounts.

• Focusing on paid subscriptions and avoiding sponsorships. 

• Keeping a high-quality bar for each newsletter post.

A pattern we’ve seen with many writers is that it can be helpful to have worked in the space that you’re going to cover. Doomberg’s experience working with writers that targeted Wall St. and high-net-worth individuals gave them a strong intuition for their ICP.

Usually, there’s an interplay between what you publish and your ICP, both evolving relative to each other over time (within reason). But in Doomberg’s case, aided by their previous experience, their ICPs have remained mostly unchanged.

The bin of great writing never read

Like other large publications, Doomberg took a systematic approach to building its audience. Starting from scratch, they developed a large following on Twitter and were able to build a large email list. 

Since the team worked on growth for other writers before launching Doomberg, they knew the importance of marketing and being self-promotional. They also knew a lot of people were uncomfortable promoting their work, and how that often condemns their writing to the “bin of great writing never read.”

Often, the people who are the most successful on YouTube, social networks, or Substack are the best marketers, not necessarily the best writers, artists, or creative talent. Marketing and selling is a crucial skill (or function if you want to outsource it) for anyone pursuing this type of professional pathway. 

The concept of “enough”

We love when the numbers go up and we celebrate it, but it doesn't consume us.

When things are going well, there can be a temptation to push for more: more followers, more subscribers, more revenue. There’s a delicate line between pushing for growth and staying true to your worldview, your moral compass, or what initially motivated you to pursue your craft.

I have yet to speak to a writer that doesn’t enjoy “watching the numbers go up”. The writers and creators we see with a healthy relationship to growth seem to view it with some level of detachment: a puzzle they enjoy working on, or a game they enjoy playing. 

One of the big questions Doomberg is exploring this year is whether they can find ways to profitably invest in paid marketing. But they will only grow their audience within self-imposed limitations — ways that don’t harm the brand or come off as inauthentic. If they can’t find ways to invest in growth within those limitations, that’s totally okay.

The team behind Doomberg has found “the work of our lives” and feels as though they’ve “caught lightning in a bottle”. They have a deep appreciation for being in that position and won’t put it at risk for the pursuit of growth.

A huge thank you to Doomberg for being gracious enough to spend a few hours with us. We hope you enjoy the conversation — let us know what you think!

And if you’re one of those angels walking on earth, please leave us a review on your favorite podcast player.

As always, thank you for your support,
Reid

Chapters

Below are timestamps for each topic we discussed:

00:00 Introduction and Background
00:42 Doomberg's Origin Story
08:33 Consulting for Finance Writers and Newsletters
11:25 Launching Doomberg
16:48 Character Sketch of Ideal Customer
21:10 Pricing Strategy
24:25 Never Want To Succumb to the Disease of More
28:58 The Doomberg Brand and Defensive Pessimism
36:38 Launching Paid Subscriptions
44:36 Throw-up Moment After Turning on Paid
52:15 Systematic Approach to Building a Media Business (The 5 Pillars)
55:50 Diving into Demand Generation
01:03:57 Guest Appearances on Podcasts to Grow Audience
01:05:12 Exploring Other Social Platforms
01:06:57 Using Social Platforms to Grow Audience
01:09:42 Searching for Profitable Growth Investments
01:18:18 Barrier to Entry is Zero, Barrier to Success is High
01:22:06 Surfing the Sea of Abundance