The next evolution of the Internet Newsletter: with Mario Gabriele of The Generalist

This week I’ve got a special guest with me: Mario Gabriele from The Generalist. 

The Generalist is really interesting. It’s an internet newsletter / publication, like mine or others I’m sure you read, primarily written and curated by Mario. But it’s not just him; it also features a lot of really high-quality guest writers across a variety of recurring segments. There’s a good chance you know The Generalist already from The S-1 Club, where investors and operators help break down and make sense of recent tech company filings to go public. 

This is really interesting to me, as someone who knows how much work it is to write a newsletter (almost) every week. There are a lot of people out there who’d love to write something for a captive audience, you know, occasionally. I have this exact problem with podcasts. I love going on podcasts. But I don’t want to have a podcast. 

There’s a really important job to do here, that I think the newsletter community has yet to figure out correctly, which isn’t how to write a newsletter; it’s how to host a newsletter. That includes writing a lot, for sure, but it’s also like the job of showrunning, and having lots of great guests, and creating recurring delight for everyone involved. The Generalist is the first great example of this I’ve seen. 

I would not be surprised if this turns out to be just as interesting a model, long-term, as the “everyone has their own Substack” setup. The trend these days is so far towards everyone having to own their own distribution to an absolute degree; and I get it, I’m certainly capitalizing on that trend. But it comes at a cost; it’s a lot of work.

I’ve seen a lot of thinking about the economics of “re-bundling the subscription newsletter”, but what The Generalist gets right (which no one else really has, that I’ve seen) is that being a guest writer on a newsletter is more like being a guest on a late-night TV show than it is like being a staff writer for a publication bundle, or even being a guest editorial writer for that matter. The guests make each episode unique, and the host makes it all fit together, every week.

So this week, here’s Mario telling us all about it. 

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Q: First question, we’ll go right to the hardest one. You have two sentences to tell my readers why they should subscribe to The Generalist and pay you money. (I do!) What’s the two-sentence pitch?

It’s a scam, don’t do it! 

Just kidding, I really hope you will. Building this company — and writing in general — is what I aspire to be my life’s work. I’m very grateful folks like Alex help me make that a reality. 

The Generalist covers tech from idea to IPO, through a series of newsletters and a curated community. It’s worth your time (and money) if you’re looking to start a company, make smart investments in private and public companies, and otherwise better understand the changes defining the future. 

Was that two sentences? 

Q: For readers that aren’t familiar, what makes The Generalist really interesting is that it isn’t just one person writing it; it’s a community of people writing and sharing high-quality business commentary under a shared masthead. The S-1 club is a great example of this in practice – for readers that don’t know it, can you explain how the S-1 club works? 

Absolutely. 

While the weekly briefings are written by me, I realized there were lots of subjects I wanted to cover that would be made better through collaboration. Who doesn’t want to hear Patrick O’Shaughnessy’s take on Unity or Howard Lindzon’s Airbnb thoughts? And what if you could bring other brilliant thinkers into the mix? 

Markets are ultimately a kind of conversation. And yet, our analysis of what happens in them is often less dialogue and more broadcast. That’s the fundamental idea behind The S-1 Club. 

Practically, that means that every time a new S-1 drops, we assemble a crew of “analysts,” including investors (venture capital, hedge funds, private equity), writers, founders, and operators to dig in. The goal is to create a uniquely qualified group. For example, our DoorDash teardown included: 

• Cristina Berta Jones, a former COO of Naspers with deep experience in food and grocery delivery. She now helps run Picnic, a large European player in the space. 
• Michael Bloch, the founder of Pillar Life. Before starting that company, he was GM of DoorDash’s New York operations, and one of the first 50 employees. 
• Ranjan Roy, writer of Margins. He wrote this unbelievable piece called “Doordash and Pizza Arbitrage,” which essentially dissected the way DoorDash was burning cash on a per-order basis. 
• Dave Ambrose is an early-stage investor with experience in the food delivery space, having backed (and worked closely with) Chownow. 
• Matt Newberg is the founder of HNGRY, a new media company focused on the intersection of food and technology. He broke the news of DoorDash’s dark store moves. 
• Daniel McCarthy is a professor of marketing at Emory and holds a PhD in Statistics from Wharton. He’s known for his incredibly detailed, granular cohort analyses of companies like Blue Apron. 

This is just a selection. But I think it speaks to the level of discourse I aspire to curate. 

Once the team is assembled, we meet for a call, share thoughts, and divide up sections. Then we all write our thoughts in the same Google Doc, commenting, and adding bits and pieces along the way. Then, we share it and talk about our findings over a public call. 

The final product is invariably much stronger and richer than I could have pulled off alone. 

Q: The Generalist is really a new kind of publication model; that’s what’s so fascinating about it. But if you had to model yourself (or look up to) any other publication or role model, who would it be?

One reader described it as combining “the wit, snark, and metaphors of The New Yorker with the tech-insight of The Information.” 

It’s a good summation of what I’m aiming for: high-quality prose applied to tech.

Q: The New Yorker is an interesting comparison in that it isn’t just news and critique, it’s also really zeitgeist-y. The tech ecosystem doesn’t quite have that captured anywhere; maybe the closest it gets is Hacker News. People really have a deep need to feel like they’re a part of something; and by reading it you take on that identity. The New Yorker absolutely gives you that. Is that a fair summary of the goal here?

I definitely think that’s part of the goal. But maybe I could put a slightly finer point on the analogy. 

What I think the New Yorker does absurdly well, beyond the quality of the writing, is serve as a contemporary historian. To your point, that often has a zeitgeisty feel, but often, I think their pieces feel a layer removed from the buzziest stories. They sort of tap your shoulder and say, gently, hey, this is important. This is interesting. 

Maybe more than relevance, that’s the sense I aspire to. That by reading you might see the time we’re moving through, just a little bit more clearly.

Q: I’m always curious what have been people’s online influences; I really think that you can learn a lot about a person by asking, what was the first place they ever posted. So: what was the first place you ever posted? And where on the internet do you really feel at home, and why?

A bit of a confession: I do not have the bonafides that I think many in tech do; of spending teenage years building websites, slipping past firewalls, and generally engaging in digital hijinks. I was not particularly early to any social network or forum.

I spent most of my childhood with my nose in a book. I would still say that is the medium in which I feel most at home. Over the past year, I’ve begun to feel at home on Twitter. I’m not sure why, but at some point the flip switched and I suddenly understood it, understood how to use and enjoy it. 

Q: What was the moment when you realized this is what you wanted to do? 

One of the first things I did when I left college and got a real job at a law firm was sign up for night school classes in fiction at NYU. 

I’d always loved to write, and as a kid, I was usually working on a story, but that class really sent me down a rabbithole. From there, I joined a workshop with some more established authors, and started writing every day. It was probably the single most-impactful professional decision I’ve ever made. Before I wrote a word of The Generalist, I spent 8 years waking up an hour early, hammering away at a novel. 

In tandem with this, I started to build a career in the tech sector, first as an operator at a SaaS company, then as a VC. I really liked both of these jobs. It was during the second that I was encouraged to start writing about technology. At first, it was just a way to build dealflow (I know, I know) but quickly it felt like it could be a lot more. 

I never thought there was a viable career in writing (at least, the kind of writing I wanted to do ), but as I saw others begin to build businesses through their online analysis, I thought it was worth a shot. In August of last year, I went full-time and things really started to take off. 

Though it’s still early days, I’m optimistic. And I feel incredibly lucky that this is what I get to do. 

Q: One of the most interesting paradoxes of the internet, and especially Twitter I think, is how it upsets the conventional wisdom on its head: it used to be that if someone offered you investing advice, you should never take it. (If it were any good, you couldn’t afford it.) But now that just absolutely isn’t true; I talked about this a bunch in my chat recently with Jim O’Shaughnessy, how now some of the very best advice is free, and the very best content comes in people’s free tiers, not paid tiers. 

The Generalist isn’t free, but it certainly seems like part of the “incredibly value and practically free” tier of the world’s internet knowledge. But how do you get people over the hump from paying nothing to paying something, if the expectation now is trending towards everything being out in the open? 

Aha! We have a disagreement! Excellent. 

First, the argument on the general level: I very much doubt I have access to the most valuable information in the world, for free. What is the most valuable “newsletter” in the world? I would argue it’s the morning Presidential Briefing, received by current and ex-Presidents. The apparatus of a nation convenes to bring a handful of people bleeding edge analysis. And there is no possible way to purchase it, no price I could offer. 

There are many venues like this. An example close that might be close to home for you: on the All-In podcast, Chamath, Jason, and the Davids often reference the group chat. How valuable would it be to have read-access on that conversation? (I could sell the Chamath nudes for six figures alone.) 

Now, Mario, I hear you saying, this isn’t reasonable. You’ve picked content that can’t be bought! That’s not the same as Free versus Paid writing! Fair point. But, there are paid approximations of these things. For example, I have, by chance, rather nifty backdoor access to executive publication that I have been reliably told costs $50K a year. Is it worth that price? Perhaps not; it is hard to gauge since I am not the profile buyer. But is it significantly more valuable than much of the free information I consume? Undoubtedly, yes. 

Now, to the particular: I don’t think my free pieces are more valuable than the paid pieces. Now, reader, you will recognize that it is in my interest to believe that. After all, I hope not only that you’ll sign up for The Generalist, but consider joining as a member. 

So, isn’t this all a bit of a soft-shoe shuffle to make my sell? (A sibilant sentence). 

I cop to a bias. With that out of the way, here’s my case. Free is not better. Free is bigger. You (Alex) articulate this elegantly in the interview with Jim — free is top of the funnel. Just as with Twitter. 

But does that mean it’s more valuable? I don’t think so. 

Increasingly, I think of the Free and Paid newsletters as different events. Free is the stump speech, hoping to attract a crowd. Paid is the fireside chat, where questions are asked and answered, and secrets are revealed. 

The way I am manifesting that at the moment is by making the Paid newsletter a collective conversation. I’ll talk through different potential topics with the community, understanding interest, fielding questions, getting feedback, and refining the scope of discussion. The result is something more intimate, more personal. But not less valuable. 

Q: How do you think about pricing your newsletter? You’re currently charging $19/month. What are the arguments for pricing above publications like the NYT and Economist?

When was the last time The Economist introduced you to a new colleague? When did the New York Times help you make an awesome investment? Or give you a startup idea? 

Ultimately, I want members of The Generalist to feel as if they’ve ripped me off. That the value I’ve delivered far outstrips what they’ve paid. The ways I think I can do that are by: 

• Giving them the information and insight to make a good investment. 
• Giving them the inspiration to start a business. 
• Introducing them to a co-founder or new colleague. 
• Helping them make their next hire. 

The community is also a huge part of this. I’m taking a hilariously unscalable approach to it — asking for thoughtful applications that require a lengthy review from me, meeting new members individually, and making detailed one-on-one connections for each person that joins. 

Q:I feel like this has been a year of fresh takes about Substack creating this entirely new employment category, and in some sense that’s not far from what you’re doing here. But you’re also marrying elements of some pretty established ideas: investment newsletters, for one, are an established business idea. And also trade publications – I still feel that people under-appreciate how big, and how important, these vertical, industry-specific news organizations can be. Do you feel like the Generalist is fundamentally something new, or something old, or what?

I hope I am filling an old need in a new way. 

To your point, trade publications can be good businesses. But fundamentally, I don’t think I would find much pleasure if I felt I was following that playbook. The writing is drab, there’s little community ethos, and perhaps even less creativity. 

I think we can do so much more, while fulfilling the same desires. I hope The Generalist will be a place people learn, make new connections and friends, build businesses, and explore genuinely novel ideas, together. 

Q: I honestly feel lucky to have this explosion of high-quality newsletters (including yours) streaming into my inbox all the time. But I do not have time to read them all; or at least, I feel like I don’t. I’m sure I’m far from your only reader who feels this way. How do you think about competition, whether it’s against other newsletters or in terms of competing for your reader’s time in general? 

Me neither. There’s always at least one piece that I want to read but inevitably forget about.

The question that I think sits beneath the stated one is this: is it worth signing up and paying for a newsletter that I might not read every week? Is there value to be gained? It makes total sense that readers worry about this — we all hate paying for something we don’t use and that doesn’t deliver value. 

I think a lot of this concern comes from the mismatched schedules with which consumers pay for value, and publications or communities deliver value. As a reader, you pay for value each month (or year) in the expectation that you’re going to get something in return. It’s a steady, linear arrangement. 

But the schedule with which you recognize that value is lumpy, and differs from person-to-person. One piece might be uninteresting to you meaning you get $0 of value from it, another might be kind of interesting, delivering $20 of value. But maybe the third piece (or the sixth piece, tenth piece etc.) is the one that really resonates, giving you an idea for your next startup. That alone might be worth $1,000. Better yet, imagine you’re in the community and make a connection to someone that gets you into a fantastic investment. How much is that worth? $5,000? $10,000? (It depends, of course.)

I’ve tried to engineer The Generalist to provide exactly these spikes, these moments of crazy value realization. 

• RFS 100 delivers curated startup ideas from the investors and GPs of some of the biggest funds in the world. 
• The S-1 Club brings together sectoral experts to dissect a company heading to IPO. 
• Weekly briefings analyze a critical trend in the tech sector, often focused around a potential investment. 
• The community brings the most thoughtful, impactful readers into conversation, allowing for new connections to form. 

I share this because it informs how I think of The Generalist in the landscape of other newsletters and communities. I know members won’t open every single piece every single time, or jump into every community discussion. But as long as I engineer my work to have 10-100x return potential for members, I hope I’m worth being a part of their information diet. 

Q: What is The Generalist, the business? Like, what, fundamentally, are you going after? This seems so much bigger than a newsletter. And, of course, it is. But I feel like we haven’t yet seen the real contours of what you’re trying to do. 

This is such a generous question. 

Fundamentally, I think the media’s coverage of tech is broken. Many mainstream outlets chase the same rage-baiting stories or fawn over the latest fundraise. There’s plenty of noise and buzz but often, it feels a little uninspired.

Outside of Stratechery and a few others blogs, we haven’t traditionally had a lot of tech-literate, high-quality analysis. And we certainly don’t have many places for those that love that kind of work to commune, discuss, and build together. 

So, here’s the ten year goal: build the most thoughtful tech community on the planet. 

Really, I hope it will be something like an open, virtual city. 

To work toward that, I have to create high-quality analysis on a consistent basis. Conversation starts more easily when there is a jumping off point. And deep analysis is magnetic to a certain type of person. Those are the people I want to build the city for, and around. This is very much the phase I’m in now; finding the believers and doing everything I can to make something amazing for them and with them. 

Then comes the next phase. 

Once you amass these people, magical things begin to happen. I’ve seen early signs of this with the S-1 Club, which unites operators, investors, and founders to dissect an IPO filing. I’ll watch as a founder trades views with a writer, goes back and forth with a VC, pushes on a hedge funder. There are moments in which you can feel new connections made through conversation. I’m also starting to see it on a permanent basis in the new community. 

Where do you take it from there? 

There are a hundred different directions you might pursue, of course. I envision new types of content (video series, podcasts), products (a dedicated startup ideas leaderboard a la Product Hunt, a clean, collaborative SEC filing reader), and organizations (syndicates, accelerators) emerging over time. A few experiments I’d like to run: 

• Build a business together. I’ve been really intrigued by the Micro PE movement, and expect to see it become an increasingly normal wealth-creation strategy. Instead of investing in real estate, someone might buy and renovate a small SaaS app. But there’s a huge education gap. I’d like to buy a small business and have the community run it together, in an open-sourced manner. You could accept applications for different positions, and eventually hand over the reins to a “founder.” 
• Pre-IPO investment syndicates. Platforms like Forge allow you to buy secondary shares in mature, private companies. Still, minimums are often as much as $1 million. Almost every time I write an S-1 teardown, folks reach out asking if I have access to any shares before the company lists (I don’t). I’d love to front-run this issue by creating SPVs that let members to invest as little as $5K into the Plaids, Stripes, and Publics of the world. 
• White-labeled Substack alternative. Building the new Generalist site was surprisingly effortful and required some relatively convoluted plumbing between products. I’d love to make it easier for other writers to move platforms, if they’d like. 

For now though, I think I have my hands full. I’m staying laser-focused on trying to write the best technology analysis online (second only to AD, the goat) and make insanely valuable connections between members. If I do those two things, I think I’ll be in good shape. 

Q: Final question for you: what’s a great book you’ve read recently? Can be fiction or nonfiction, any topic. 

I’m currently reading Pale Fire by Vladimir Nabokov. I’ve been on a bit of a kick recently — first Lolita, then Pnin, and now Pale Fire. I don’t think there’s ever been a better writer than Nabokov; every sentence is a game, a trick, a gift, something singular. 

When I let my imagination go wild (and my self-confidence reach dangerous, entirely unearned levels), I dream of, one day, building something, being something between him and Walt Mossberg. But I will save the rest of that vision for Egomaniacs Anonymous. 

Thank you so much to Mario for taking the time to come on the newsletter – hopefully at some point you’ll see me poking my head out on The Generalist too. I certainly hope you subscribe; I get a lot out of it and I’m sure you will as well. 

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