How Mario Gabriele Revolutionized the Newsletter Business

Founded by Mario Gabriele, former Venture Investor at Charge Ventures, The Generalist dives deep into one technology related topic a week and features original reporting from world-renowned experts.

While certain newsletters focus on brevity, The Generalist is as it sounds - general. Pieces routinely clock in at 10,000 words and only a year old, The Generalist has more than 41,000 subscribers. Last year the business made $300,000 in revenue through sponsorships, subscriptions, and NFTs.

I had a chance to speak with Mario about "compounder-gate", quitting his job to work on The Generalist full-time, and his writing process. Simply put, The Generalist is anything but a typical newsletter.

This interview has been edited for clarity.

Life Before The Generalist

Mario: My first job after college was at a law firm. It was incredibly boring. Once I realized this, I decided to attend night classes at NYU in fiction writing and fell into a workshop with senior writers. It ended up being the best experience of my life.

Each week we’d bring in seven pages from our novel and this got me into a cadence of waking up an hour early before work to focus on my writing. That's still how I start a lot of my days, working on fiction.

At a certain point, colleagues of mine encouraged me to write about technology. It quickly turned into an obsession of mine and since then I've written a post for The Generalist every week. In August of 2020 I went full-time, so I’ve been properly working on it for a year.

Going From 5,000 to 40,000 Subscribers

Mario: There've been little spikes along the way. I made an announcement about going full time last year and put out a deck that outlined where I hoped to take The Generalist. That gave me a little bump. Then I launched on Product Hunt, and that was another little bump. I also wrote a piece on Red Bull and the thread I wrote about it on Twitter went viral which drove a bunch of signups. But that one was weird, also, because it was paywalled.

The final spike was when this hedge fund threatened to sue me in October of last year. I had written a piece with a collaborator about compounders, which are just companies that grow repeatedly year after year.

For some reason, this hedge fund got it in their head that the notion of compounders and phrases, like “good to great”, to describe these compounding companies was proprietary information. It was very strange and confusing, but also pretty scary.

There was a $6 billion hedge fund coming at me and I was earning zero money at that point. I tried to resolve it amicably several times with them and they still couldn't articulate what was the matter with whatever I'd written in any sort of logical way. I was lucky to be able to get a lawyer who worked pro bono in media law to help me with the situation. It was super stressful, but it ended up having a happy ending.

Moving Off Substack

Mario: The Generalist started on Substack. In January of this year, however, I stopped using Substack to post my articles. I now use a site built on Webflow which was more work to build, but it’s nice to no longer lose 10% to Substack.

I’m also using ConvertKit which allows me to cast a slightly different vision of my brand than Substack permits. While Substack is great for starting out, it is still pretty narrow in the way that you can present your work.

In the beginning I had a personal website as coming from the VC world, you're aware of the need to start building a brand early. My personal website was a way for me to build up the courage to do that.

The First 100 Readers

Early on I reached out to several collegiate VC Clubs since I thought MBA students would enjoy it.

One time I messaged the the Head of the VC Club at Wharton and said, “Hey, some of your members have signed up for The Generalist, just wanting to share it with you and see if it might be something you'd be down to share with your cohort.”

A lot of the time people would say, “yeah, great. This seems awesome." Sometimes people didn't respond - that was fine too - but I never got pushback about my outreach. It probably helped that I was working at a VC, too.

Initial Marketing Strategies

Mario: If you go back through the archive of The Generalist on Substack, there was one format where I was rounding out the top tweets of the week. Those carried on, and the guiding principle I landed on was trying to figure out where I could generate value over replacement. The first Generalist was really a link round up, but it didn't lean heavily on the place where I have strength - which is my writing ability.

Back then, The Generalist was less compelling to sign up for because there were lots of similar products. People could also sign up for Morning Brew or The Hustle or The Download, or anyone else who curates links.

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.

Post Production Process

Mario: It varies every week, but a post will usually take between 50 and 60 hours. It's rare that I have a plan, but it's nice to go into the week with an idea. Monday and Tuesday are often research heavy. The week before we'll set up calls with experts, so I'm not having to frantically email people or DM people to steal an hour of their time. I don't take days off at this point.

On Wednesday I'll start outlining the piece and putting a bit of scaffolding in place. Then I just work progressively until I publish on Sunday. The thing I'm usually looking for is not quite a hook, but a concept that is able to explain a topic in an unusual way that reveals the truth about it. The tough part is I usually only have a few days of really thinking heavily about an idea.

Being A Reporter

Mario: I never think of myself as a reporter. Sure, I talk to experts and quote them but there is a key difference between me and general reporters, which is that I default to anonymity with my sources. This aspect of my reporting has helped me earn the trust of my sources and convince them to share information they might not otherwise.

My content is more similar to equity research. It's about granularly diving into the financials of certain companies, it wouldn't give me pleasure to pump out a 200 word piece that broke some news about tech. I care more about writing something that is definitive on a subject.

I'm confident now that if anyone wants to learn about FTX in their short reading list, the trilogy will be in there. Maybe it won't be number one, maybe someone else will write something better, but my work will have its place.

That, to me, strikes me as a very different cadence than most news, which is designed to serve a very urgent purpose.

Leveraging Twitter

Mario: Last summer I had about 500 followers, so I set out on a mini-quest to post a thread every day. Most of them got no attention, but it gave me a degree of comfort with posting. Social media is such a crap shoot that it's hard to put too much faith in it as a creator.

The Inflection Point

The first year of doing it as a side hustle, I got about 5,000 subscribers. Then in the last year, it went from 5,000 to 41,000 subscribers. Being able to put out increasingly better pieces every week, I think made a huge, huge difference.
I didn't monetize The Generalist until January of this year.

It was like a leap across the Rubicon, and so far 2.3% of the free audience has converted to paid. I've heard of newsletters being able to get to eight to 10%, to a certain degree, though The Generalist is fighting against best practices. Usually niche products tend to do well on a subscription side for media and my work is...general. So, I think it's less of a direct sell.

Multiplayer Pieces

Mario: One of the hacks I've developed are pieces I call "multiplayer pieces". First, I pick the subject, for example, tech in Africa. I don't know enough about that ecosystem, but I'm really interested in it. It would be almost impossible for me to get up to speed on it to any degree of authority in a week's time so instead of trying to do that, I bring in 10 other collaborators, people who are building companies in Africa, or building funds in Africa and say, “let's work on this together and then we'll share it.”

We all come together on a call, talk about it, and divide the piece into different sections. Then once everyone had finished their sections, I come in and tell the story around it. So, in the end, you get a piece that hopefully has the brain power and depth of real experts, but still reads coherently. It's also an especially powerful approach because you have 10 vectors of distribution rather than just one.

As long as you do a good job, people are excited to share it.

Challenges So Far

Mario: The two that come most to mind are 1) endurance and 2) consistency.

You have to have a lot of endurance to write every week, 10,000 words. That is like writing a thesis once a week, so you definitely have days where words are coming out ugly. The only solution is to just power through and recognize you have to get something out by Sunday.

The second piece is consistency, both in quality and in growth. The past summer for The Generalist was a big slow down - I went from 15% growth a month to 4% - and it was the first time I had to experience what a slump felt like. The only thing I could do, though, was power through.

Content Strategy

Mario: One of the things that has been valuable for me is changing the content up based on current trends. If anything has been super hot this summer, it is crypto, and people have more appetite to learn about right now than a piece on a traditional tech company. So, I’ve been able to reflect that in my subject choices.

Also, the deeper I go into a topic the better response I get. I did a trilogy on one company called FTX and got the CEO to open up their data room and bring out a ton of information that had not been shared publicly. Unsurprisingly, that has been one of my best performing pieces in the last six months. However, the thing that I have not done is shift away from direct and social traffic. If I had a better SEO game, it would help during quieter months.