Evolution of a Newsletter Journey

Mario Gabriele is the founder of The Generalist. His mission? To bring the most interesting tech writing to your inbox, every week. And he’s not doing it alone, either: Mario works with a team of contributors to deliver new ideas from some of the most original minds in venture capital and tech.

In this episode, Mario talks about how and why he left a career in venture investing to build The Generalist, and his lifelong obsessions with writing and technology. The Generalist is not only a really successful newsletter, it’s a thriving business, too! Tune in to hear how Mario did it.

You’ll learn about approaching and collaborating with the people you only dream of working with. Mario talks about how he went from merely admiring certain writers’ work to joining their “club” in 18 months!

Mario also shares the most reliable way to advance your career, and the safest ways to accelerate it. There’s a lot of good stuff in this conversation!

Links & Resources

• Stratechery by Ben Thompson – On the business, strategy, and impact of technology.
• Exponential View by Azeem Azhar
• The Nathan Barry Show 028: Packy McCormick – How Much Are 30,000 Subscribers Worth?
• Acquired Podcast
• Atonement by Ian McEwan
• Norwegian Wood by Haruki Murakami
• All-In with Chamath, Jason, Sacks & Friedberg
• Webflow: The no code platform for web design and development
• Pico - Signup and payment tools for the internet’s most passionate communities
• alexdanco.com – subscribe weekly at danco.substack.com

Mario Gabriele’s Links

• Personal site: The Generalist
• Twitter: @mariodgabriele

Episode Transcript

Mario: [00:00:00]
I just really love writing very, very much. And so, as soon as I got the width that like, maybe I could make this a real thing, then suddenly like a flip switched in me where I was like, all right, I have to go as hard as possible and feel like the value was accruing directly to me. As soon as I was like fully on my own thing, I suddenly felt like, Oh man, I’m unchanged to go after this. 

Nathan: [00:00:30]
In this episode, I talked to Mario Gabriele. Now Mario runs an email newsletter called The Generalist, which is focused on tech venture capital and investing. He comes from the venture capital world himself, and then he really brings forward all of that into the newsletter. A couple of things really impressed me about Mario. One, he really collaborates, well, he’s got something called the S–1 Club, which is where they do tear downs of filings that companies make before they go public. And he really brings in other creators and they write them together. He also has something called RFS, which is Request for Startups and he brings in other venture capitalists and operators and everyone else to share startup ideas.

So he’s got this interesting mix of his own Content, Community Content, and he’s built it not only into a really successful newsletter, but also a thriving business. So it’s a lot of good stuff. Let’s dive in.

Mario. Thanks for coming on the show.

Mario: [00:01:25]
Thanks for having me, Nathan.

Nathan: [00:01:26]
Okay, so you have this line. I think you said it on Twitter and a few other places that I just want to start with. You said, it sounds ridiculous to announce your dream is to build a great newsletter and then you go into like, you know, but that’s what I’m doing, you know, my love of technology and writing and everything else. So maybe just start with why, like, why did you want to start a newsletter?

Mario: [00:01:52]
Yeah. I mean, honestly it wasn’t, something that was necessarily in the back of my mind for a long time, it really sort of happened organically. and I think work is often like this where for a long time, you’re not really sure exactly what you’re doing. And then. When you sort of find something that actually feels incredibly right, you can sort of trace back all the little things along the way that brought you there.

And so for me, that was really two main, explorations. One was that, you know, from a very young age, I’ve always really enjoyed writing. and so I did a lot of that in school. and then after I’d left university, I started to take night school classes and fiction writing at NYU. Starting in 2012, I started to like write a novel every morning, getting up early, you know, spending an hour before work, just sort of like practicing, practicing, practicing.

And it was just sort of this hobby I had. And then simultaneously where I was really building a career was in technology. so. You know, on the operating side, at a few companies and then on the investing side in sort of a few venture firms and, starting The Generalist really was just a way to.

You know, I express that hobby in a slightly different way. I had folks be like, all right, cool. You’re spending all this time writing. Like what, why don’t you write a thing or two about, about your actual work? and so just started as sort of a side project on the weekends and then bit by bit, it just was absorbing more of my thought.

More of my excitement, more of my energy. And it started to really feel like it was pulling me in this direction. And, once I felt like it might be possible for writing to become. My life’s work and be a viable career, which had always been sort of the reason I hadn’t tried to go full-time as a novelist.

You know, even though, you know, unless you’re JK rallying, it’s pretty impossible. newsletters felt like a way I could do that and really write the stuff I wanted to write, and make, make a living out of it. Hopefully.

Nathan: [00:04:09]
Yeah. So, it’s, we’re recording this in February, 2021. When was it that you started The Generalist?

Mario: [00:04:16]
So I start, I wrote the first ever post in August of 2019. And honestly was sort of an accident that I started it as a newsletter. I had just been seen seeing people like switch over to Substack over Medium. This is before I had heard the gospel of ConvertKit. So, yeah, I was just like, cool.

I’ll do this instead of Medium, like whatever. and then. That first post, even though it was very small circulation just led to so many interesting conversations and people started to sign up. And so it suddenly became like very clear why you should make it a newsletter versus a blog. and then I would say the other sort of critical point was in August of the following year. I went full-time on it. And the growth since, since then has been like significantly different, I would say, just like being able to put more time into it.

Nathan: [00:05:15]
Yeah. So, there’s a few things that I want to dig into there, but, I think there’s all these creators that we look up to and admire, right? The newsletters that we read, that YouTube chann...