Top 6 Substack Newsletter Success Stories in 2025

Substack is an emerging platform that is growing rapidly and newsletters have been around for a while now, and while they might seem like a relic of the past, they have evolved over the years and remain an effective marketing tool. In this article, we will discuss successful substack newsletter success stories that you probably haven’t heard of before. These success stories are meant to inspire you to create your own successful newsletter.

Substack Newsletter Success Stories

Below are a few examples of actual success stories from individuals who started a Substack newsletter:

1. Grit Alpha ($420K/year)

Grit Alpha was started by Jack Kerouac (pseudonym) more than 2 years ago.

Founder	Jack Kerouac
Revenue	$35K/month or $420K/year

As a background on myself, I spent many years on the buyside focused on fundamental analysis on potential investment ideas that could generate high alpha. I spent an additional five years as a private investor where I generated consistent returns. I recommended dozens of high quality investment ideas to the fund I worked for that, delivering alpha for our investors. [READ FULL HERE]

2. Yolo Intel ($240K/year)

Yolo Intel was founded more than 4 years ago by Yolanda Edwards, who is from Brooklyn.

Founder	Yolanda Edwards
Revenue	$20K/month or $240K/year

Hi there. I’m Yolanda Edwards. a longtime magazine editor based in New York. For years I’ve worked in travel editorial—in my 20s as a photo editor at Condé Nast Traveler, then as the travel & lifestyle editor at Cookie (RIP) and later as the creative director of Condé Nast Traveler. I’ve always gotten the best advice from people who travel a lot, and have great taste—not necessarily writers. I first decided to start my quarterly print magazine, Yolo Journal, because I’m passionate about photography, travel, and collecting great ideas, and a forever lover of the printed page. [READ FULL HERE]

3. Cup of Coffee by Craig Calcaterra ($221K/year)

Craig Calcaterra, who is from New Albany, OH, started Cup of Coffee by Craig Calcaterra more than 2 years ago.

Founder	Craig Calcaterra
Revenue	$18.4K/month or $221K/year

You love baseball, but you also have a life and a family and a job and stuff. You don’t have all day to scroll social media and go to a half dozen ad and video-filled websites in an attempt to stay up to date. Wouldn’t it be way better to have a quick, entertaining, and informative one-stop daily baseball briefing, delivered directly to your inbox before you have your first cup of coffee each morning? That’s what Cup of Coffee is for. [READ FULL HERE]

4. TSOH Investment Research Service ($192K/year)

About two years ago, Alex Morris founded TSOH Investment Research Service, and he is from Davie, FL, USA.

Founder	Alex Morris
Revenue	$16K/month or $192K/year

Through the TSOH Investment Research service, I provide complete access to my investment research process and all portfolio decision-making. The portfolio disclosed to subscribers includes all of my investable assets (everything outside of a small checking account). My promise to subscribers is 100% transparency.

In a nutshell, I share all research and portfolio activity with subscribers. [READ FULL HERE]

5. Chief in the North Newsletter ($48K/year)

11 months ago, Seth Keysor started the Chief in the North Newsletter.

Founder	Seth Keysor
Revenue	$4K/month or $48K/year

This is the Chief in the North Newsletter, a dream a decade in the making.

I’m Seth Keysor (or MNchiefsfan if you’ve been around a while), and I’ve been writing about the Chiefs for over 10 years. What started as a hobby to fight “hot takes” became something much more, and I’ve been privileged to write for both SB Nation and The Athletic analyzing what is really happening on the football field and what it all means.

For years, I’ve wanted to try out a direct link between Chiefs Kingdom and myself. No editors, no deadlines, no assignments. Just me and you, talking about football. That’s what this is. [READ FULL HERE]

6. WiFi Money ($36K/year)

Opossum(Anonymous) started BowTied Opossum almost 2 years ago.

Founder	Opossum(Anonymous)
Revenue	$3K/month or $36K/year

I started learning digital businesses on and off when I was younger but never took it seriously as a business. Once I did, I realized how much knowledge I had accumulated over the years. Through teaching interns and analysts, I realized that the biggest barrier to starting your own side hustle is the initial learning curve.

My first ~10 posts are about the *basics* of getting started.

Why?

There is an absolute dearth of actionable information all in one place for how to start. This is the biggest barrier to WiFi money. [READ FULL HERE]

Revenue source: StarterStory

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