How Mario Gabriele Disrupted Tech Analysis with The Generalist
Exclusive Interview and Product Growth Tactics of the 50K+ Newsletter
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.
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:
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.
To get the rest of the story, as well as the product growth takeaways, check out the rest of the piece. It was too long to fit in e-mail:
Just answered the puzzler for the latest solo capitalists issue. I'm enjoying the collaborations, profiles, and "the making of" theme developing with the pieces!