How I Leveraged My Twitter Audience And Launched A $420K/Year Finance Newsletter

Published: June 13th, 2022
Jack Kerouac (pseudonym)
Founder, Alpha Letter
Alpha Letter
started January 2021
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Hello! Who are you and what business did you start?

Thanks for having me on Starter Story. I can’t disclose who I am for professional reasons, but I started, run, and operate Alpha Letter and a few other financial media publications. Some people know me as Jack Kerouac. Others call me Anon. And then others call me by the dozen or so Twitter accounts that I have run in the past or currently running.

My flagship product that I run is Alpha Letter. Alpha Letter is an investment newsletter that is focused on finding small out of favored value stocks that typical Wall Street hedge funds can’t or won’t touch.

I use a bottoms-up approach to investing and focus 70% of my time on balance sheet analysis and the remaining 30% of my time trying to forecast what free cash flows could be in the future for any given investment I am interested in. The companies I write and talk about are not sexy tech stocks and most of the time have never been covered by sell-side firms. They are small companies that are out of favor and unloved.

Alpha Letter is my main product and 90% of my revenues but I also run and operate other financial media websites such as The Free Press Report, The Stonk Market, and a handful or so social media pages for myself and clients.

Today, all my properties collectively are bringing in around $30,000-35,000 in revenue per month.


What's your backstory and how did you come up with the idea?

During the dark days of 2020, I had the idea to make The Onion of finance and investing. I know the investing space well and toyed around with FinTwit (the finance portion of Twitter) in the past. While bored from working at home and had nothing else to do, I launched The Stonk Market and a few parody Twitter accounts.

The website got pretty popular and at its peak, I had over 50 different people writing for me. The website got great views, but I couldn’t figure out a way to monetize it. At the best, I was doing maybe $300 per month in revenue and writing 3-4 satire articles per day.

Views depended on my tweets going viral, so I spent a lot of time figuring out how to make content go viral on Twitter. I guarantee that if you can get a lot of people to see whatever you are doing on the internet, you can create a high six to seven-figure business with enough creativity.

Fast forward to early 2021 and the whole GameStop and AMC fiasco happened. For those who don’t know, retail investors were short squeezing hedge funds by purchasing heavily shorted stocks like AMC and GameStop up in droves. To capitalize on this, I created a Twitter account called @redditinvestors that went from zero followers to over 150,000 followers in a couple of weeks.

The account went viral because I tweeted that I was going to track stocks that WallStreetBets was going to attempt to short squeeze. I then used the viral nature of this account to feed into what is now called Alpha Letter. In a week’s worth of time, I gained 150,000 Twitter followers and funneled 20,000 of these new followers into a brand-new email list that is now called Alpha Letter. That is when I became a newsletter writer.


I knew email lists were valuable, so I wanted to funnel as much traffic as possible to my newly created newsletter. I didn’t realize how much value they had until I started writing one consistently. At first, I was writing just a free version 2-3x per week. I was selling ads for $250 per issue and making decent money doing it. Writing didn’t take up much of my time and I was spending maybe 5 hours per week on it. Then I decided to turn on the paid version and see if I could monetize the list that way as well.

The paid version was an instant success. Annual recurring revenues went to $30,000 per year the first day I turned it on. Having that recurring revenue source made me realize that a paid newsletter is a great business and something I wanted to spend more time on.

Pricing of Alpha Letter was determined on other successful Substack publications. I searched on Substack and saw that most publications were selling their paid version for $10-20 bucks per month. I initially started with $10 per month to see if I could get a large number of free subscribers to bite. Once I got 500 paid subscribers I doubled pricing to $20 per month.

My pitch for the paid version was that paid readers would get all my stock picks that Wall Street wasn’t looking at. I would write research reports on these stock ideas 2-3x per month and have my actual money invested in these stocks. Readers can then choose what they do with the information in the paid version. This isn’t financial advice, but more high-level research on small stocks you won’t find anywhere else.

Building this newsletter has been game-changing for me as an entrepreneur. The newsletter business is different from any other business in the past I have tried to build. There is unlimited upside as you can leverage the power of the internet to create viral content. This viral content can then be used to funnel directly into your newsletter and build your list however big you want it to be. I’m pretty good at making content go viral on social media and I now have a way to monetize these views.

Alpha Letter has now been running for 12 months and has a free subscriber base of 82,000 individuals

Take us through the process of designing your newsletter and monetizing it.

Building my product was pretty easy for me as I enjoy writing and I can write fast. For content, I write a free newsletter at least once or twice per week, depending on if I can sell ads, and then write a paid version for paying subscribers 2-4x per month. The free version is 1,500-2,000 words and typically goes over my philosophical thoughts on value investing, macroeconomic themes, personal finance, etc. The paid version is research on small value type companies with my opinion and analysis on what I think those companies are worth.

For the free version, I sell one advertisement placement for $1,200-2,000. These placements first started at $250 per placement when I had only 20,000 subscribers and have rapidly expanded as my subscriber base has increased. To source advertisers, I would use a third-party ad seller who would find ads to fill my newsletter with every month.

The third-party ad seller would take a percentage of the gross revenue off the top and I would keep the rest. Also, back when I had multiple large Twitter accounts advertisers would come to me. I don’t get as many inbound ads directly anymore, which shows the power of having a large social media following. As for the paid version, subscribers pay $20 per month to get access to all my research.

Startup costs for my business were minimal. I went through Legal Zoom to set up the LLC and may be paid $700 all in. I run my business through Substack which makes writing a newsletter seamless. I was up and running and taking payments on Substack in less than an hour. Substack takes 10% of my gross revenue from my paid revenue stream, which seems reasonable to me as I don’t have to build out my website or deal with the tech headaches of accepting payments and refunds.

Describe the process of launching the business.

I launched Alpha Letter in less than an hour. When my Reddit Investor Twitter account went viral, I immediately opened a Substack account and started funneling people into my email list. I used fear of censorship to create a sense of urgency. For example. I would tweet about how the “Suits” were trying to take down GameStop and AMC and then I would tweet how big tech was going to censor me.

If people wanted to keep in touch when they banned my account, they would follow my newsletter ASAP. This fear of censorship is huge today on social media because big accounts get banned for really anything these days without an explanation and is a great way to drive followers to a newsletter. The viralness of the Reddit Investor Twitter account allowed me to launch a large newsletter in less than an hour and within a week I had thousands of free subscribers I would write to.

After the @redditinvestors account calmed down, I launched two other accounts @NancyTracker and @TrialTracker, and created that same viral nature to funnel emails. I used @NancyTracker to track stock picks from Nancy Pelosi and other politicians. The account instantly blew up with over 200,000 followers in a few weeks. I used the same viral principles to drive people to Alpha Letter.

I would tweet how the big wigs in the White House and tech overlords were going to ban me for exposing how politicians make money using valuable insider information. My newsletter subscribers exploded during this period growing from 20,000 to over 50,000. Since I had my paid version on during this time my paid revenues went from $30,000 per year to over $200,000 per year.

The big jump in March was from the @redditinvestors Twitter account. The jump from September to October was from @NancyTracker

Finally, I created the @TrialTracker account to track the Ghislaine Maxwell and Jeffrey Epstein trial. The media was not allowed to film the trial and there seemed to be public outrage at this. The account was my biggest social media success going from zero followers to over 525,000 followers in a couple of weeks. This account was the largest known source of the Ghislaine Maxwell trial and got an insane amount of engagement.

I would suggest connecting with every big influence that follows you and networking. Social media is a powerful tool for connecting with people. If you make an account and go viral you will eventually have big named people following you.

During the Ghislaine Maxwell trial, I launched The Free Press Report and used the fear of censorship to drive subscribers to a new email list. This email list went from zero to over 50,000 subscribers in a few weeks.


By this time, I was generating over $30,000 per month in revenue across all of my platforms and rapidly growing my newsletter base.

If you want to build a media company or brand the biggest lessons I took away was to build a large social media following. There are hundreds of other writers who are way better than me at putting out finance content but no one ever reads their stuff. They don’t know how to market their product and get eyeballs to see what they are writing. If you want to get in the media business learn how to get eyeballs on your product then worry about creating quality long-form content.

Since launch, what has worked to attract and retain customers?

Create great content that provides value to your customers, and they will come back. My goal with the newsletter is to write about finance and investing topics no one else is talking about. There are thousands of people writing about Tesla, Google, and Facebook. There are very few people writing about coal mines trading under book value in the Appalachian Mountains. The goal of my newsletter is to write about these off-the-beaten-path investment ideas that you will not find anywhere else on the internet. If I can do this in a high-quality fashion, my customers are likely going to be repeated.

If you are in the media business, I would learn how to make content go viral. You can create the best long-form content in the world but if you don’t have a distribution channel, no one will ever read it. I know a ton of writers who are way better than me, but I get 100x the views because I know how to make things go viral. Focus first on the marketing and then focus on the quality content. Once you get your large base of readers the quality of your long-form content.

If you don’t know how to make content go viral I would suggest becoming friends with individuals who do know how to make content go viral. I have a list of a bunch of high-profile meme accounts on Twitter that I pay to subtweet content that I write. For example, if they have a viral tweet, I will throw them a few bucks to tweet about my newsletter under it. Both parties win as they get to sell ad space and I get to use the viral nature of their tweets to collect more newsletter subscribers.

How are you doing today and what does the future look like?

The future for my business looks promising. I have had a few setbacks like Twitter banning all my accounts out of nowhere. The only explanation that I have on that is that I was getting so much engagement on the @TrialTracker account that my account was surpassing that of any reputable news source. I could tweet anything and the tweet would do 15,000 likes and thousands of retweets.

I woke up one day and saw an email that said Twitter banned my account for “artificially” amplifying information (which I still don’t know what that means) and banned every account that I ran at the time. This sucked at first, but it got me a ton of media coverage and drove even more traffic to my websites. Big named media companies like Fox News, Zero Hedge, and even The Joe Rogan Podcast covered it and linked my newsletter.

So far Twitter banning my major accounts and marketing arm has been my only setback. This sucked at first, but it taught me an important lesson if your entire business relies on social media that is likely not a great business. I was very thankful I built two large newsletters out of those Twitter accounts as I own and control my list and the direction I take it.

Despite this small setback, I am back on Twitter and starting to create viral content again. One of my new projects is to build a newsletter publication on “Dirty Businesses”. My goal is to build up a bunch of Twitter accounts that highlight dirty businesses such as prison owners, strip club operators, tobacco manufacturers, drug dealers, arms dealers, etc., and drive their virality into a newsletter that highlights these businesses. I have only launched one account so far, but it has taken off and I think I might be onto something here.


In terms of Alpha Letter and the current media properties I currently own, my short-term goal is to get them to $50,000 per revenue each month. Right now, it is just me writing and operating these properties and I may look to hire someone to help create content in the future.

Through starting the business, have you learned anything particularly helpful or advantageous?

The best thing that I have learned through starting my business is that there is a lot of money to be made online in small niche markets. I guarantee that if you can get a lot of people to see whatever you are doing on the internet, you can create a high six to seven-figure business with enough creativity. Personal branding is huge. If you are an entrepreneur, it pays to create a personal brand of yourself on social media. I have seen hundreds of entrepreneurs talk about life lessons and business wins/mistakes and build a huge personal media brand that not only creates their ancillary revenue but also creates significant value for their main business.

Also, when you are first starting on social media, the grind is slow. It took me many months to build a following up to 5,000 followers. The next 5,000 was quicker. And the next 10,000 was even quicker. Instant virality takes a lot of time, creativity, luck, and getting the formula right. If you want to be in this business just wake up every day and create great content that people like. Eventually, you will hit a home run and that homerun will pay off.

What platform/tools do you use for your business?

Around 5-10% of my day-to-day time is spent using Substack and Twitter. Twitter is used to create viral content with the goal of feeding readers into my Substack for more long-form content. Other than those tools, I don’t use anything else. In all honesty, I spend most of my workday using Microsoft Excel and the SEC website to create financial models for small companies that I am researching to make an educated and intelligent investment.

What have been the most influential books, podcasts, or other resources?

The most influential book for me has been Trust Me, I’m Lying: Confessions of a Media Manipulator by Ryan Holiday. This book blew my mind away. After I read it, I learned how media businesses really work and that views are all that matter if you want to generate money for your investors. That book was a game-changer and taught me good principles of ongoing viral and how to emulate the tactics that big media does to drive views.

Advice for other entrepreneurs who want to get started or are just starting out?

The number one best tip that I have is to look at what other successful people are doing on the internet and replicate it either in the same niche or in a different niche. When I first started in the Twitter game, I mostly looked at @RampCapitalLLC as the formula meme account that I needed to replicate. Meme Twitter was not as big back when I first started, and he was the main one so I did what he did – made funny content that went viral.

In addition, I would suggest connecting with every big influence that follows you and networking. Social media is a powerful tool for connecting with people. If you make an account and go viral you will eventually have big named people following you. Use this to your advantage and shoot them a note. A conversation out of nowhere can lead to a business deal down the road.

Are you looking to hire for certain positions right now?

I am looking for someone to sell ads for my free version on Alpha Letter and The Free Press Report. If you are great at sales and are connected to finance, investing and political brands I would love to chat. My goal would be to sell an ad 5x per week across both Alpha Letter and The Free Press Report. Feel free to reach out to me at [email protected].

Where can we go to learn more?

You can follow me at the following links, happy to chat anytime.