How Mario Gabriele Disrupted Tech Analysis with The Generalist
With pieces that have read times in the hundreds of minutes, The Generalist is like if Wikipedia were written by a fiction writer who worked in Venture Capital. It turns out, it kind of is that.
Mario Gabriele has managed to forge one of the most unique media brands in the technology landscape. His deep dives into a topic aspire to be “essential reading.”
Looking back at The Generalist’s last year, it is hard not to think about all the pieces that were produced and passed around like hot potatoes on tech Twitter:
The VC firm playing it differently: Tiger Global
Ethereum’s hottest competitor: Terra
The $100B private payments giant: Stripe
So, it seems, for many, they have become essential reading.
The numbers back it up. The Generalist has crossed over 53,000 subscribers as of publishing. When I wrote Packy McCormick and Not Boring three months ago, Packy was at 80K. Now he has crossed 100K. When you read this, Mario and The Generalist will be at some higher level.
The combination of consistency, depth, and continual iteration make Mario’s newsletter stand out as one that is disrupting the space. Newsletters from Mine to Top of the Lyne, Net Interest, and Li’s Newsletter have pieces with companies as the unit of analysis, but Mario has taken the continued focus and length of pieces to the next level. Most pieces are on a disruptive new company or trend.
So, it was a pleasure to spend the past few weeks digging into the existing interviews and great pieces on Mario. I then capped that off with a chat with the writer himself, to bring you exclusive insight into:
The Makings of a Newsletter Writer
The Evolution of a Newsletter
Lessons from The Generalist
If I have accomplished my goal, this too will become essential reading on Mario’s ascent.
The Makings of a Newsletter Writer
Chapter 1 - Early Writer
To be such a prolific writer, it is no wonder that Mario grew up in and around the world of books and reading. As a child, Mario was inspired by books like Roald Dahl’s Fantastic Mr. Fox. The book is a 96-page children’s classic in the UK, reflecting Mario’s upbringing in England.
https://youtu.be/jfZMI_P9H_0?t=136
As Mario aged in school, he began writing more and more. It was one of his favorite ways to go deep. As Mario told Nathan Barry:
From a very young age, I’ve always really enjoyed writing. So, I did a lot of that in school.
2008
His household was an international one. His father is an Italian and his mother an American. So, perhaps it was no wonder that, at age 18, Mario moved to the United States.
The writing would help Mario craft essays that helped him gain admission to Columbia University.
At school, Mario was interested in public policy. “A Tiger,” as he described himself at school, Mario poured himself into the essays required to make it through the Ivy League Political Science curriculum.
As you might expect given his writing talents, he graduated Summa Cum Laude. With the world his oyster, interested in public policy, Mario found himself headed to a law firm.
Chapter 2 - Legal Misstep
2012
Have you ever worked at a law firm? I did an internship for one the summer after my sophomore year of high school. The striking thing about working at a law firm is that nearly everyone working there does not like what they are doing. Sure, folks are happy and animated at the water cooler. But, at work, they are dry and out of energy.
Mario felt the same way when he found himself at a law firm. Without a law degree, he was not doing intellectually stimulating work. It was nothing like writing dramatic political science essays, almost the opposite of discussing legal topics at Columbia.
One of the great benefits of being in New York City is that opportunity abounds. Bored with his day job, Mario enrolled in a night class for fiction writing. Another perk of being in NYC, Mario was able to do so at the other prestigious university in town, NYU.
It was the classic, “bored in the day, happy at night,” situation for our young hero. He began work on a novel and reconnected himself to the writing roots of his youth.
Entrenching himself in the writing world got Mario connected to people far more excited about their work than the law firm. It was a natural fit.
Before long, Mario found himself in a workshop with other writers. Each week, they brought 7 pages of their novel to share. Mario had found a group that did not enjoy chatting at the water cooler, but actually doing the work itself.
This got Mario into the cadence of waking up early to write for an hour. It was a habit that would help drive many reps of practice. Mario continued to progress down the path of 10,000 hours.
2013
Chapter 3 - Life Experiments
A Period of Wilderness
That’s how Mario characterized the post-Law school period to the Foster writing community in an interview. Mario eventually realized he was not interested in becoming a law partner.
Like many polymaths before him, Mario decided to pursue an entirely different field from both his first job as a lawyer and his Ivy League degree: cooking. Mario enrolled in culinary school. In a way, Mario was shifting his work from that of a legal peon to a more creative field, the culinary arts.
Throughout this time, Mario continued writing for an hour in the morning. Determined to finish his novel, he continued to work his writing muscles.
2014-2015
While the creative work was for Mario, the cooking wasn’t the same as writing. Mario still yearned to make an impact on public policy.
Using his writing skills, Mario penned essays that earned him another crack at the public policy world. He went back to Columbia to pursue his Masters's in International Development.
2016-2017
Chapter 4 - The Context to Share
After graduating with his Master's, Mario entered the tech world. He joined the seed stage Venture Capital firm Red Sea Ventures. It was a great place to learn. The firm invested in east coast startups up now public like Allbirds and sweetgreen.
Then, Mario jumped over to AND CO, a freelancer software service. Learning the world of B2B SaaS after working on consumer at Red Sea helped Mario round out his knowledge of all sorts of technology companies.
2018
After AND CO, Mario returned to Venture Capital to work at Charge Ventures. There, Mario also got to work under the, “fascinating, electric thinker,” Brett Martin. Mario felt passionate about his work, all the while continuing to work on his writing habit.
Working under Brett was energizing, but as time went on Mario found himself wanting to dedicate more time than he was able to writing. He tried out creating another written series called The Prologue. But, that did not fit.
Luckily, in the world of Venture Capital in 2019, writing was an edge. Not only were the established, older players like Fred Wilson blogging, younger VCs like Aviral Bhatnagar were as well. Mario’s colleagues did not bristle at his interest in writing. They encouraged it.
2019
Chapter 5 - The Courage to Write
In August of 2019, Mario used a flight to draft his first article. A few days later, on August 16, he published his first article, on Y Combinator. Titled, “30 Minutes or Less: The Manufactured Urgency of YC Demo Day,” it was a deep commentary on one of the biggest events in tech.The piece did well, and it opened Mario’s eyes about what it is like to share ideas publicly.
As Mario said about his time in Venture Capital:
It was during my stint as a venture capitalist that I got up the courage to start sharing my work in public.
This is a crucial moment for any future newsletter writer. They have to crossover from writing at work and in school to sharing in public. With Mario’s YC piece, he got that courage.
The Evolution of a Newsletter
2020
Chapter 1 - Becoming a Newsletter
After the Y Combinator piece, Mario kept writing. Initially, he thought it could be a daily habit. That lasted all of two days.
So sharing writing became a weekly habit for Mario. And, bit by bit, The Generalist was born.
But, it wasn’t always called The Generalist. The newsletter began as Brunch Briefing. Early versions included tweet and link roundups. As Mario explained, “the value over replacement was low.” People could sign up for any other link curator.
Eventually, Mario found a niche. As Mario said to Indie Hackers:
I was able to separate myself by going deep in a way that few were doing… Ultimately, I'm telling a story in as narratively compelling a way as possible that is different from a lot of more perfunctory business writing.
Mario started writing in his signature style: deeply, and with narrative half. He succeeded by doing something different (lesson 1).
Chapter 2 - Early Growth
To get early subscribers, Mario did “things that don’t scale.” This included activities like reaching out to the VC club president at Harvard or Yale. He’d offer them his free newsletter, “maybe you want to read it or want to send it out to your group.” Many would.
In April 2020, Mario would launch the RFS 100. This was, remarkably, the same month Packy McCormick merged his social club Not Boring into his newsletter. Both began towards the start of the Covid-19 pandemic, and have continued stratospheric ascents since.
At the time, Mario had the strategy to build out several different newsletters:
In May, he launched the S-1 club. That would catch on in particular. This led to two important insights that shaped the future of the Generalist: multiplayer pieces and companies as a unit of analysis.
Multiplayer pieces are a tactic the Generalist relied heavily on during its growth in future phases. Mario developed a unique model to manage large groups of contributors, like the 10 additional contributors to The Generalist’s piece on Tech in Africa.
Mario would pick a topic and tweet about it. This would enable him to bring together a team of experts. The team would have a call to discuss the piece, assemble, and split up an outline. Then, Mario would go in to make sure afterward to fill in gaps for people who got busy, and to write it from a single, unified voice, instead of sounding like disparate writers.
It worked wonders for both piece quality and distribution. Often, if the contributors were proud of the piece, they would promote it in their own channels as well.
Some collaborations were just one on one. For the now-famous Ant Group piece, Mario collaborated with Lillian Li of Chinese Characteristics. Mario was taking a piece out of the YouTuber's playbook: growing through collaboration.
Using companies as a unit of analysis was the other foundational learning for Mario from the S-1 club. He realized there “is a massive TAM,” for analysis of companies compared to other think pieces.
He had a string of pieces that performed extraordinarily well:
They attracted an audience. So, Mario framed the problem to himself as, “how do I turn towards what people really like, without losing the parts of myself that make me enjoy writing?” He really liked the origin stories of companies.
Fast forward to today, and Mario expects, “at least 75% of The Generalist will remain company pieces for the foreseeable future.” That is a massive insight, all dating back to Mario’s strategy to start wide at first, and then double down on what works (lesson 2).
What makes people love company pieces so very much?
People like to read stuff that they might be able to act on. That could be investing, joining the company, or applying a lesson to their current roles.
Doing it as a side hustle for a year, Mario extraordinarily got 5,000 subscribers.
Chapter 3 - Going Full time
Exactly one year from the day Mario published his piece on YC, he announced he was going full time - August 16, 2020:
https://twitter.com/mariogabriele/status/1295031676989345792
Mario detailed many of the reasons behind his decision in the 62-page deck he includes in the thread. One of the most interesting is his breakdown of the potential for creators. His comparison set included podcasts, YouTube, and streaming.
In August 2020, newsletters weren’t quite as established as they are in February 2022. So Mario didn’t include Pomp, Lenny, Polina, or some of the myriad of other highly successful newsletter writers these days.
He wandered into the scary new world and dove in headfirst. Each week, Mario scheduled calls with experts for his piece for the next week. Then, the week of, he used Monday and Tuesday for research, Wednesday for scaffolding, and progressively work to publish on Sunday. It was a 7 day a week, 80+ hour grind.
As Mario says:
It’s hard to turn off as a solopreneur, as the work relies solely on me.
When you’re playing a game where each measurable increase in quality and dedication pays off in your growth, the incentives are perfectly aligned. Mario kept working hard and growing fast.
Chapter 4 - The 6 Billion Dollar Stare
In late 2020, Mario worked with a collaborator who formerly worked with the $6 billion dollar hedge fund, Durable Capital.
The collaborator, proud of the piece, shared it with a former partner at the fund. Also a Columbia Business School professor, this partner did not take a liking to the use of compounders in the piece Mario and the collaborator had written. They felt ownership over the idea.
Quickly, everything escalated. Mario, a solopreneur working his butt off and earning zero money, was getting threatening messages from the General Counsel of a giant firm. It would be an anxiety-inducing, scary experience for anyone.
But, as Mario says:
The Internet is undefeated.
Mario was able to connect with a media pro bono lawyer. They helped him through, and he didn’t cost him.
It was likely a case of the Streisand effect. The firm wanted to reduce attention on Mario’s piece, but their lawsuit actually generate much more attention for The Generalist. By November 3, 2020, The Generalist had hit 13K subscribers.
2021
In early 2021, Mario continued to hit his stride. The Generalist launched a large site redesign. Subscribers and traffic continued to grow briskly.
One of the items that helped growth takeoff was Mario’s best tweet ever even to this date. In April, Mario shared the launch of his piece on Red Bull with a thread that went massively viral:
https://twitter.com/mariogabriele/status/1378787515969253376
Chapter 5 - The First Slowdown
In the summer of 2021, The Generalist hit its first slowdown. The newsletter saw 4% month-over-month growth vs 15% historically.
Mario had to have the endurance to get through. One big change he made was to finesse his content strategy. This is the same evolution Packy at Not Boring made later in his arc: he started writing about topics that were even hotter and of the current zeitgeist.
In the summer of 2021, that was crypto. Mario used the interest to spur a series of strong pieces on Crypto:
June 27: What to watch in crypto
July 18: Robinhood
August 1-15: FTX Trilogy
September 12: Sushiswap
October 10: OpenSea
The final one, on October 10th, was shared by Tim Ferriss, the original content creating writer himself. Mario exited the doldrums of the summer and continues on the exponential growth path.
In September, Mario also published The Generalist Turns 1, a piece I have cited many times already in this history. One of the most interesting things Mario shared was the revenue breakdown for The Generalist:
Fully three quarters of the business relied on subscriptions for revenue. As a writer of this piece, for my first draft, the story ended here. Mario represented the archetype of a premium newsletter.
But, in The Generalist’s world, nothing stays constant for too long.
Chapter 6 - NFTs
The first big change for The Generalist was NFTs. Mario became one of the few creators to experiment with NFTs during the general craze for the things in October.
The timing was perfect. A week after his piece on Opensea, the #1 NFT marketplace, Mario published the piece, NFTs that Think.
I remember getting the piece to this day. I thought I would log on to Opensea after work. But what started as 0.1 ETH a fox rose to 4.5.
The data is all available on Opensea. The primary sale netted the project $150K, and secondary sales have netted well over $35K. It was a massive success that may continue. Mario noted that he plans to aggressively reinvest in building the project and community around it, with aspirations to make it one of the most valuable in web3.
Most importantly, for Mario:
It was one of my favorite things I’ve ever done.
2022
Chapter 7 - Changing the Business Model
The second big change for The Generalist from the days of 75% subscription revenue occurred at the turn of the year. The Generalist’s content went totally free. It was an incredibly bold move for a site which gained many of its subscribers by paywalling content.
This was the topic I couldn’t wait most to dig into with Mario. What was the rationale? It turns out, there are four main reasons.
Growth is capped behind the paywall
There’s something awesome about making this work for free
Better revenue model
Community surprised Mario in the first year
The first is perhaps the one most on the outside would jump to as obvious. Growth is capped behind the paywall. Mario saw a slight slowdown in the summer of 2021 despite the quality of pieces continuing to increase. One potential conclusion could be that he didn’t see the growth of other similar newsletters because some of the content was paywalled.
That might have been one part of the story. Another was that predicting which piece would be best for new audience growth beforehand was a fool’s errand. When we chatted, The Generalist’s piece on Tiger Global was its biggest yet. Newspapers rewrote shortened versions of it, the research was so thorough and well presented.
But The Generalist would have missed out on all the growth of the Tiger piece if it had been a paywall. This insight pushed Mario to keep everything open.
The second reason Mario decided to go free was, as he said, “there’s something awesome,” about making this work for free. Availability is sexy. Suddenly, HBR-level case studies are available to anyone who is curious and on the internet.
The third reason is that free represents, from Mario’s vantage point, a better revenue model. Because The Generalist is, well, general, it has a much harder job tapping into the same share of wallet that an industry-specific newsletter can. There are few people expensing it, or getting group accounts fo business.
Sponsorship, on the other hand, is something that grows with the audience. Mario can charge based on the expected opens of the message he intends to send.
Finally, Mario made the dramatic shift to free with confidence because the community surprised Mario in the first year. As I know as a member, people make friends. The events are high quality and intimate.
So, unbundling the community from a more nebulous membership will help The Generalist go all-in on community. There are a few pillars to the community: curated intros, conversations in Circle, literal events, and investments. This represents a complete package to keep the subscription business going.
Overall, with these four reasons in mind, Mario made the dramatic pivot (lesson 3). And, it worked. Cancellations have been in the low single-digits, even though Mario is happy to refund anyone. On the other hand, Mario has been able to grow The Generalist readership faster than ever, and subscriptions have grown as people join specifically for the community.
Present - The Generalist Today
Today, The Generalist is amongst the foremost newsletters. It has been acknowledged as a thought leader in several publications. Cited by prominent news outlets, it has gone from an interesting side project to an enviable brand.
Mario was even verified on Twitter.
https://twitter.com/mariogabriele/status/1479461920499511305
The Foxes NFT also had its second big drop last week. Things seem to be humming for Mario on all fronts. When I asked about revenue now that all writing was free, Mario was confident 2022 would exceed 2021. Mario has managed one more pivot, and we can expect more to come.
Future - The Generalist of Tomorrow
The plan for The Generalist is more or less public. Mario has shared it:
Of course, things change. RFS and the S-1 club have collapsed into Briefings. But the next step seems clear: a fund. Will Mario make the leap that Lenny, Packy, and so many other tech creators have done?
We will have to wait and see.
Takeaways from The Generalist
Lesson 1 - Succeed by Doing Something Different
Mario’s work is a deft mix of equity research, origin stories, fiction-level writing playfulness, and the encyclopedic depth of Wikipedia. There’s nothing quite like it. It’s not reporting because he defaults to anonymity for sources.
It’s also different from the other newsletters. Packy McCormick tends to write with more of a personal voice. Lenny Rachitsky tends to write more from the angle of product or growth. Benedict Evans tends to comment on most news. Ben Thompson focuses on the strategic frameworks and breakdowns. Mario, amongst long-form business writers, is unique.
These days, what’s more common is to see shorter form narrative storytellers. Prolific writers like Shreyans, Jesse, Sahil, and Trung may even heavily cite a Mario piece to create their pithier, small versions.
Mario, on the other hand, is playing a different game. As he says:
The goal is to become essential reading on a topic.
Lesson 2 - Double Down on What Works
Mario’s story is one of doubling down. First, he doubled down on his side hobby and went full-time. Then, he doubled down on companies as a unit of analysis by focusing pieces on them.
After experimenting with several different newsletter types - from RFS to the S-1 club - Mario saw success with briefings and went all-in on them.
Now, more recently, he has doubled down on crypto with NFTs.
Mario runs his newsletter like a true product. He is constantly doing little product growth experiments. Then, when he finds a growth lever that works, he doubles down on it. This is the essence of product growth optimization.
Lesson 3 - It’s Never Too Late to Pivot
It’s hard to understate how bold Mario’s various pivots have been, none more dramatic than moving The Generalist from a premium newsletter subscription to a premium community at the turn of the year.
Even at 50K+ subscribers, Mario is learning and trying new things. Pivoting has been at the center of the success of many of the great businesses we have studied in this blog. It is no surprise it is at the heart of one of the great newsletter products we have studied.
The internet really rewards the more “you,” you give.