How Edwin Dorsey Built a $900k Newsletter Business: The Bear Cave

Can you imagine being 25 years old and making over $900k from your own business?

And that business lets you explore all of your natural curiosities but people paid you for them?

That’s exactly where Edwin Dorsey is at today, and there is a lot we can learn from his journey.

Edwin writes The Bear Cave, a newsletter geared toward “investors, short-sellers, journalists, and skeptics,” where he uncovers fraud and bad actors within organizations.

He writes really in-depth articles uncovering bad actors in finance and business, which in turn help people make better decisions in the stock market.

And his research is much more valuable than just helping people short-sell stocks. His articles have led to CEOs stepping down, stock prices crashing, and businesses being publicly exposed for their wrongdoings.

Can you imagine a 25-year-old having that much of an impact on an industry?

How Edwin Makes Money

There is only one method Edwin is making money from his newsletter business, and that’s through paid subscriptions.

He doesn’t even buy or short-sell the stocks he talks about because he feels it would be a conflict of interest.

The Bear Cave Newsletter

Edwin makes money via paid subscriptions to his Bear Cave newsletter.

At the moment, he charges $64 per month, or $640 for the year.

This is one of the most expensive paid newsletters we’ve seen thus far.

But, he is putting together deep dive research that could end up making you a lot of money in the stock market. When you’re making people money, they’re much more willing (and able) to pay for it.

In a recent tweet, Edwin said that he had around 1,232 paying subscribers.

If we take a conservative approach and say that every one of those people purchased the cheaper annual plan, here’s where we end up:

1,232 subscribers x $640 =
$788,480 per year

But wait, there’s more.

Sunday’s Idea Brunch Newsletter

In September 2021, Edwin launched a second newsletter called “Sunday’s Idea Brunch” where he publishes interviews with really smart investors.

He asks them things like how they do their research, what they’re currently watching, and what they’re investing in.

This newsletter is also paid, at $17 per month or $170 for the year. Much cheaper, but also really simple for him to execute.

These are text-based interviews, so he could really just send the list of questions to potential interviewees. Once they reply, he might do a little formatting cleanup but then he can just hit publish.

What an interesting way to leverage the relationships he’s built and pretty much get some free content that people are paying for.

The overall newsletter has 9,000 subscribers, and in March he had 739 paid subscribers.

At $170/year (again using this cheaper rate to give a conservative estimate) that’s an extra $125k per year in gross revenue.

That brings the total revenue for Edwin to over $900k per year.

As a solopreneur. Writing about the stuff he loves to research.

And this is why I love newsletters. Well freaking done, Edwin Dorsey.

His First Deep Dive

Edwin wrote his first deep dive back in June of 2018, almost 2 years before he had ever considered starting a newsletter. A friend told him something fishy was going on at Care.com, and he couldn’t resist the urge to dig in.

Turns out, that friend was right.

Edwin wrote a deep dive about everything he found (including how he was able to sign up a fake account under the name Harvey Weinstein at the height of his own scandal.)

It got a little traction on Medium.com, but he knew this needed more press. He ended up cold-emailing 150 journalists, and the Wall Street Journal ended up doing a full investigation.

Care.com was eventually disbanded as a company.

It wasn’t until 2 years later that he really leaned into this idea and started publishing regular deep dives to uncover the bad actors in the business and finance world.

The Growth Timeline of Edwin Dorsey

While he had done some in-depth research before starting the newsletter, he officially launched his Substack in late February 2020, right before the whole world shut down.

In the beginning, he was more focused on trying some growth tactics and trying to grow the newsletter. But in October 2020, he started publishing deep dives more regularly and the growth really took off.

The 5 Growth Levers

So we know that this 25-year-old is making a killing, but how did he grow this newsletter in the first place?

Here are the growth levers I found:

🥋 1. Hand-to-hand combat. Edwin wasn’t going to just wait around for subscribers to find him – he went out and made it happen.

🧪 2. Be willing to take risks. The newsletter he writes today is not the same as it once was. And changing it up is what led to his explosive growth.

🕵️‍♀️ 3. Create content others won’t. People are inherently lazy, it’s just a fact. But Edwin does seriously deep research that others aren’t willing to spend the time on – and it’s led to some great opportunities.

🪄 4. Creating serendipity. While some might call it luck, the act of creating consistently can lead to incredible results. Edwin uses this concept as fuel to keep going.

🥊 5. Be persistent. The level of grit and persistence that Edwin displays in his work is unmatched. We all can learn from the way he approaches life.

Let’s take a look at each one and how it helped Edwin build such an incredible business.

1. Hand-to-Hand Combat 🥋

Edwin started the newsletter in February 2020. At the time, he had around 3,000 Twitter followers and 0 subscribers.

He decided he was going to get his subscribers from that Twitter following.

When he launched the newsletter, he tweeted to his followers, but quickly realized he was going to need more than a few people to get traction.

So, he did what any recent college grad with a lot of time on their hands would do: he DMed all of his followers and asked them to subscribe.

Not only was he messaging each of his Twitter followers, but he also cold-emailed all of the investment clubs at Stanford University (the college he went to) trying to drum up more subscribers.

“I spent three days. My eyes started to hurt. Just DMing every Twitter follower, being like sign up for this newsletter, please!”

“That’s what built the early momentum. I clawed my way to 3,000 free subscribers by October.”

Edwin Dorsey

It might have hurt a little bit, but he got up to 3,000 subscribers by doing so.

2. Being Willing to Pivot & Take Risks 🧪

The Bear Cave newsletter started as Edwin sending out a curated list of interesting insights for people around public companies and their potential problems.

He used this format for 33 weeks, with one or two deep dives sprinkled in. The newsletter was growing, but I think he knew there was a better way to do things.

Plus, he was hoping this could be his full-time job. He decided to lean into the longer format and decided he would publish 2 every month for premium subscribers.

And while he liked this concept, he wasn’t exactly sure how people would react to this new format and cost.

Turning on Premium Subscriptions

In late September, he turned on premium subscriptions. Here was the announcement:

On the first day, only 10 people signed up.

He told Andrea Koppel that he called his parents and said, “I screwed up so big, I’m going to be earning nothing, and unemployed.”

But he didn’t back down, he just kept moving forward with the new model.

If you’ve been paying attention so far, you’ll know that it turns out okay. Within a few months, he said “it had taken off and tons of people were paying for it.”

By February 2021, he had over 500 paying subscribers, which was more than $150k in annual revenue.

3. Unique, Deep Dive Content 🕵️‍♀️

To put together such insightful deep dives, Edwin compiles data from a variety of sources that most people never take the time to look at. He scours the internet, government websites, public documents, legal filings, etc. to find any potential red flags about the companies he’s investigating.

He spends more time than most on one specific company and publishes everything for his readers to see.

He’s saving people a ton of time by doing all of this research and sharing the findings for a small monthly fee compared to the value.

You need to be intellectually honest and highlight stuff that people don’t know about and isn’t well publicized, and that’s stuff people will pay for.”

– Edwin Dorsey, Institutional Investor

Because of this, his content gets shared all over the place.

Leads to Amazing Backlinks

Not only does he get shared by individual people, but his work ends up in articles for large media companies like:

  • Rolling Stone
  • Seeking Alpha
  • Benzinga

People would pay money to be featured in some of these publications, so the fact that he’s getting backlinks from them (as far as I know) based purely on the quality of his content is huge.

If you’re not familiar, having links from websites like this can help you show up higher in search engines.

And from some estimates I found, it looks like he is getting around 16% of his overall traffic from Google – not too shabby!

4. Creating Serendipity 🪄

Edwin is a big believer that writing online is one of the best things you can do. You quite literally never know who is on the other end of the computer screen reading your work.

David Perell is another creator who is adamant that writing online builds a serendipity that you can’t recreate elsewhere.

When Edwin got started, he said he was thinking: “I’m going to write online, show people I’m good at this digging, and they’re going to want to hire me.”

Little did he know that writing online would become the actual job, and he’d have thousands of people “hiring” him to write deep dives.

Writing Online

His secret to connecting with people is writing online. You quite literally never know who is on the other side reading what you’re putting out.

But there is also something to be said about proving yourself through consistency that is very underrated.

A lot of people who start writing online quit after they don’t find traction early on. That’s why a lot of established writers, ones who have been doing it for years, might be skeptical of the newbies out there.

They don’t know who is going to still be doing this in a few months.

But as you continue to write/podcast/create week in and week out, people notice that you’re still there.

You’re putting in the work and proving that you’re going to stick around for a while.

And those more established people start to take you seriously. They might jump on a call, offer advice, or connect you with others who can help you grow.

The snowball starts slow but can speed up very fast.

Podcast Interviews

Edwin has been on a number of podcasts, and he feels strongly about saying “yes” to every invitation you get.

Not only are you building connections with other creators, but it’s a great way to get in front of another audience who might enjoy your work.

Whether you’re writing online, or having conversations on podcasts there is a level of “magic” that can come from content.

Using Twitter as a Testing Ground

Edwin spends around 2-3 hours a day on Twitter looking for information and getting insights into what’s happening around the space.

But he also uses Twitter to test out content by sharing a little bit about what he’s thinking about. If it gets a good reception and people are interested, he’ll continue with the project.

If not, he might shelve that idea for an article or thread for a later date.

We saw this with Dickie Bush and Sahil Bloom as well. Test your content before you spend a few hours writing a thread about it.

One example of this was his ARK Invest piece, which he talked about on the Creator Habits podcast:

“I tweeted about it once or twice and it would get 1,000 likes, 50 retweets and tons of replies, and I thought, there’s a big demand for somebody to come in here, do some real research.”

He said that because his tweets were getting such great engagement and feedback, he spent 10 hours putting together a well-researched article on it.

And it turned out to be his most-read article at the time.

5. Be Persistent 🥊

Edwin is the kind of guy that just doesn’t give up when he wants something. If he gets knocked down, he just gets right back up with another plan.

I came across a few stories to show you the level of persistence we’re talking about, but this one is my favorite.

Cold Pitching a Hedge Fund

There’s another story of epic persistence he told on the Pomp Podcast. Here’s the timestamp of this exact story if you want to listen for yourself.

There was a well-known hedge fund in San Francisco that everyone said he should talk to. So he cold emailed them a bunch but they wouldn’t answer his emails.

After not getting a response, he got on the train and went to their offices.

The guard wouldn’t let him upstairs because he didn’t have an appointment.

📝 Taking a step back, most people would have stopped after they didn’t get a reply from the cold emails. And of the people who decided to show up, most would have quit after the guard told them no.

But not Edwin.

He sat in the lobby and found everyone who worked there and started messaging them on LinkedIn, saying something to the effect of:

I’m in your lobby, I’m a freshman in college and, I really like stocks. Can I pitch you something?

One person finally responded and came down to the lobby to let him up.

The meeting ended up going well, and leading to new connections, along with probably a ton of lessons on what hedge fund managers are interested in, and a taste of what meetings like this feel like.

There was another story about him calling an old hedge-fund investor out of the blue, and the guy ended up becoming his mentor.

When he told this story on the Chartcast podcast, the host TC says:

“I have to say, when Mark tells the story, there was a lot more pestering on your side.”

I find these hilarious and great examples of just how persistent this guy is, but how it all seems to lead to something positive.

How You Can Replicate Some of Edwin’s Success 🗺️

While he’s struck upon a seemingly perfect mixture of market, audience, and content, there are a few ways you can replicate some of Edwin’s success.

Do the Things Other’s Aren’t Willing To

If you’ve been reading Growth In Reverse for a while, you probably know I’m a huge proponent of the deep dive format.

Most people aren’t willing to put in the time or effort to create content in that format because, well, it’s hard.

Because it’s rare, you’ll have a better chance of standing out from the crowd. You’re creating a level of content people aren’t used to seeing.

I also think there is some level of reciprocity going on here.

People can feel and see the effort you’re putting into your work, and they feel obligated to share it with others. People sharing these deep dives have led to a good chunk of the growth I’ve been able to see with the newsletter.

Edwin is seeing the same thing. People are willing to pay hundreds of dollars for the research he’s done, and they also share it around, building a self-perpetuating marketing tool for him.

How can you create content that is:

  • More in-depth than anyone else
  • Saves your readers time
  • Provides value
  • Is unique

If you can combine all of these, you’re onto something big.

Use Serendipity as a Motivator

If you see other creators showing up everywhere and getting “lucky”, chances are they are simply just doing more.

  • Saying yes to more podcast interviews.
  • Creating content whenever they can.
  • Writing every day.
  • Going to events.

You quite literally never know who you’re going to meet or how they could change everything for you. You might find a new business partner or meet someone who knows that person you’ve been wanting to interview.

The more you show up and say yes, the more chances you have to create serendipity for yourself, and the more likely you are to have these encounters.

Be Persistent

One of my big takeaways from this deep dive is to be way more persistent in going after the things I want.

If there is something you really want, you have to go after it. We know that.

But how many of us are willing to find the third door when we get knocked down the first or second time?

You want 3,000 email subscribers, have you DMed everyone on Twitter asking them to subscribe? Have you exhausted all of the avenues you have available?

chenell basilio

Chenell Basilio

Chenell is the head writer and reverse engineer at Growth In Reverse. She spends her days researching newsletters, audience growth, and generally figuring out how to help others create better content.

She has an almost useless Bachelor's Degree in Geography, enjoys running, listening to podcasts, and eating guacamole. 🥑

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