My Story

I’m not your average 20-something.

I have an ability that few my age – aside from the occasional wunderkind founder/CEO – have ever had: I can move markets.

I graduated from Stanford in 2020 and run a newsletter on Substack called The Bear Cave, which boasts more than 50,000 subscribers. Of those, about 1,300 are paid subscribers.

The newsletter is focused on corporate misconduct – specifically I write about $1-billion-to-$10-billion, U.S.-listed public companies that I feel are misleading investors or harming customers.

Between that revenue and the money I make from a second, smaller newsletter dubbed “Sunday’s Idea Brunch,” in which I sit down to interview great investors, I have annual recurring revenue, or ARR, of about $500,000 after costs.

And I do it all while getting in 15,000 steps a day and sometimes working as little as four hours per week.

The Start of My Newsletter Empire

I’m a bit of a finance wonk. As an economics major at Stanford, I worked ahead to graduate a few months early (in the portentous month of March 2020). Then I set to work on The Bear Cave newsletter.

Having interned for a hedge fund all four years of college, I didn’t spin up my newsletter to strike it rich.

I thought, ‘Hey, I need to get a job. One way that I can get noticed is to start this newsletter,’ So The Bear Cave was not originally started as a moneymaking thing, it was more as a way to keep busy during the pandemic, and hopefully get someone to notice my writing and give me a job.

I did it, in short, to get noticed by hedge funds.

From Free to Paid: The Evolution

But that soon changed. Things got off to a good start, and later that year I made a decision. In September 2020 I started charging for my newsletter.

Subscribers to the free version of The Bear Cave get a weekly summary of news in the world of activist investing and a slew of interesting tweets from across the investing world, while paid subscribers also get two deep-dive investigations per month on public companies I view as problematic.

When I first made the leap to the paid route, I made a bold choice, pricing my service at $34 per month or $340 per year. It worked. Within a month and a half it was doing about $100,000 in annual recurring revenue, and I knew it would be my full-time job.

I became one of the fastest authors in Substack history to reach $100,000 in ARR. There’s a reason my newsletter could quickly command such a price, which is more than three times the cheapest non-ad-supported Netflix Inc. (ticker: NFLX) plan: Correctly wagering against overvalued public companies can make you a lot of money on Wall Street, and investors are always looking for ideas.

My own policy, in contrast to many famous short sellers who put out bearish research of their own, is to never wager against the companies I write up, making money from subscriptions alone.

Track Record of Success

That said, The Bear Cave’s success as a business is directly tied to my impressive track record of sniffing out losers. Here are just a few of my notable bearish write-ups:

Since my Dec. 3, 2020 exposé on insurer Root Inc. (ROOT), shares have plunged about 98%.
Two weeks later, on Dec. 17, the market took notice of The Bear Cave report on blockchain-enabled trade finance platform Triterras Inc. (TRIT). Shares took a 31% one-day beating on heavy volume following my published investigation. In less than 15 months, shares were delisted from the Nasdaq. Triterras is now a penny stock on over-the-counter markets.
Oct. 7, 2021: The Bear Cave publishes “Problems at The Joint Corp (JYNT).” Shares fall 11.3% that day on elevated volume. From there, it’s down another 80% and change as of early May.
On Dec. 1, 2022, in one of the more timely calls in The Bear Cave’s brief history, I devoted my paid newsletter to investigating Silvergate Capital Corp. (SI), the crypto-focused lender that would, months later, be one of the first dominos to fall in the still-evolving regional banking crisis. Less than 100 days after my report, Silvergate announced it would be liquidating its operations.

The Path to $500,000: Newsletter Economics

Yes, on a lax week – one where I’m not doing one of my famed twice-monthly deep-dives on companies I’m sour on – I can work as little as four hours. And yes, The Bear Cave was able to quickly pick up paid subscribers. But there’s a lot of behind-the-scenes work that had to happen to build the newsletter business I enjoy today. “The tough thing was getting it jumpstarted a little in the beginning,” I admit.

“I used Twitter, but some things I did that put things in my favor were I individually DM’d all 5,000 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.”

As for how I got the contact information of the college investment clubs: “You make a list of the 200 biggest colleges and you start Googling each college investment club and you cold email the person you see in charge.”

The Business Today

Even today, I admit that as a finance nerd, the “line between work and personal gets very blurred … but in a week in which I’m obsessing over something [the work week] could be closer to 100 hours.”

In order to give my subscribers their money’s worth, I still do the type of grunt work you might expect from a hedge fund employee, filing Freedom of Information Act requests, digesting footnotes in Securities and Exchange Commission documents and parsing statements from management for red flags.

Here’s how the economics of my two newsletters break down:

The Bear Cave has around 1,300 paid readers bringing in about $550,000 in ARR. When the newsletter first started charging, it cost $34 per month or $340 per year. In January 2021, I raised prices to $44 per month or $440 per year. The average subscriber pays somewhere around $35 per month at the newsletter’s current run rate. (Shortly before this article was published, I raised prices for the second time ever to $64 per month or $640 per year. “Every time I raise prices I grandfather in existing readers at the lower rate.”) Sunday’s Idea Brunch has around 700 paid readers bringing in about $50,000 in ARR.

That’s a gross of around $600,000 between my two newsletters, but then there are some modest costs to doing business that add up: Substack takes a 10% cut; credit card fees and Stripe, the payment platform, eat up around 3.5%; and then refund requests total about 0.5%. Those costs add up to about 14%, or $84,000 per year, meaning my current take-home run rate is roughly $516,000, give or take, before taxes.

Recommendations for Others

When asked what I’d recommend to other aspiring paid newsletter entrepreneurs, I break it down into a sort of formula.

“Find a niche, get very knowledgeable about it, get very excited about it and build a Twitter following in that domain,” I say.

If you can do that, then start a free newsletter geared toward your passionate followers. “After a few months, if it’s growing well, you can create paid content in that area.”

Looking to the Future

I started The Bear Cave in an effort to get on Wall Street’s radar. That strategy has worked; many of the hedge funders I might’ve worked alongside are now Bear Cave subscribers. But I no longer aspire to work for a hedge fund.

“My goals tend to be rather personal,” I say. I’m mainly focused on doing good work, getting in great shape and having fun. “I spend three hours every day walking in New York City. I try to get 15,000 steps a day walking outside if it’s sunny out.”

“If I had a financial target, I’d like to get to $1 million in ARR by the end of the year … I think I can do it, it’s growing fast.”

So, beyond financial milestones, what’s next for me professionally? I’ve done well on Substack, but I’d like to try my hand at another digital media platform as well.

“If anything, I want to get into YouTube,” I say. “The goal is to keep killing it with the newsletters, and then eventually invest in making YouTube content focused on exposing corporate misconduct.”

Corporate wrongdoers, take note. I’m watching – and I’ve got quite a following.

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The End

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