Entrepreneur: Edwin Dorsey

Biz: The Bear Cave

Tilt: Exposing corporate misconduct

Scene: Newsletter on Substack (64K), X (100.7K), Sunday’s Idea Brunch newsletter (9K), Dorsey College Stock Pick Competition

Snack Bites: 

  • Edwin launched The Bear Cave newsletter to market his knowledge to prospective Wall Street employers.
  • Less than a year later, he became a full-time entrepreneur, grossing six figures with his weekly summary of news in activist investing.
  • In launching the newsletter, he sent direct messages to all 5K of his Twitter followers. He also emailed college investment clubs, thinking the students would talk about and share his newsletter.
  • Edwin has increased his monthly rates from $34 in 2020 to $64 in 2023.

Why We Stan: Edwin follows the content entrepreneur model – finding mentors, limiting expenses, and building an audience before launching a paid product.

The Story of Edwin Dorsey

Edwin Dorsey didn’t start out to become a content entrepreneur.

He launched a newsletter to market himself to prospective employers. Edwin explains to Morning Brew, “So in February 2020, I just started my Substack (The Bear Cave) mainly as a way to get attention with the hope that, ‘Hey, if I put out smart content, people will find it interesting, and maybe someone will want to hire me.’”

The Bear Cave is a weekly summary of news in activist investing – a topic he’s long been interested in and motivated by his mentors. “I’ve been passionate about stocks since second grade,” Edwin tells Morning Brew. “Then freshman year of college, I got really lucky by getting introduced to two really big short sellers—people who bet against companies professionally—and they kind of became my mentors.”

By the fall of 2020, Edwin launched a paid newsletter and earned more than $100K six weeks later. That version includes two investigations on public companies per month.

Edwin Dorsey (@StockJabber) launched The Bear Cave #newsletter to get a job. He turned it into a full-time, six-figure creator business. #Stan #CreatorEconomy Click To Tweet

That’s when he turned from job hunter to a committed entrepreneur.

In May, he had 47K subscribers – 1.3K pay for The Bear Cave, according to an interview with US News, which led to $500K in revenue. (This month, he has 64K subscribers.)

He also added a second newsletter, Sunday’s Idea Brunch, featuring an interview with a great investor. That, he tells US News, has about 700 paid readers. 

Edwin broke down the revenue for Morning Brew. For every subscriber dollar, he earns 86 cents, Substack gets 10 cents, and the credit card companies receive 3.5 cents.

In 2020, he charged $34 a month or $340 a year for The Bear Cave newsletter. He raised his monthly rates in January 2021 to $44 or $440 a year. That rate remained until mid-2023, when they increased to $64 a month or $640 a year. 

Edwin tells US News when he increases the rates, he keeps the original rate for existing readers.

As an entrepreneur, he keeps his business expenses low – accounting, legal services, and taxes are his most significant bills.

Though success came quickly, he worked hard to build his initial audience. In this US News interview, he explains: “I individually DM’d all 5K of my Twitter followers, and that took like three days. And then I also made a list of every single college investment club in the country, and I cold-emailed all of them, with the logic being that college students will share and talk and forward – that’s how I got a bunch of signups in the beginning. That’s when you needed to really hustle.”

Edwin Dorsey (@StockJabber) sent direct messages to his 5K Twitter followers asking them to subscribe to his #Substack newsletter before it launched via @USNews. #Stan #ContentEntrepreneur Click To Tweet

Edwin also has some more great advice for newsletter creators: “If you are even thinking about cutting something, then cut it. Your readers will thank you.

Photo Illustration: Francis Scialabba, Source: Edwin Dorsey

About the author

Ann regularly combines words and strategy for B2B, B2C, and nonprofits, continuing to live up to her high school nickname, Editor Ann. An IABC Communicator of the Year and founder of G Force Communication, Ann coaches and trains professionals in all things content. Connect with her on LinkedIn and Twitter.