031: Mario Gabriele – From Lifelong Obsession to Thriving Business

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 channels that we follow, all of that, and there’s sort of this. Feeling of maybe otherness, we’re the person watching it.

And they’re the, you know, the famous person creating the content, whether it’s the Casey Neistat or the Ben Thompson or, or whoever. And I’m curious who were a few of those first, like newsletters that you were reading where you’re like, Oh, maybe, maybe I want to be like that.

Mario: [00:05:48]
Yeah, definitely. Ben Thompson was like the first person I saw doing this in where I was like, is this, this guy’s job? Like he’s obscenely smart. And it seems like he’s doing well. but I didn’t realize you could do that. so, so he was really one of the first and then. Azeem Azhar writes something called Exponential View.

I don’t actually know if it’s his full-time job. Cause I think he’s also a venture investor, but, it’s certainly a business. and so that was another one where I was like, yeah, this is a brilliant tech commentator who seems to have it as part of his career stack. And it just felt like, you know, the very least it was going to be a massive advantage to any traditional career I wanted to do.

And, you know, hopefully the, the way to build a career.

Nathan: [00:06:41]
Was there any feeling of moving from? So from my perspective, you’ve moved from that, like the consumer, who’s just, you know, reading these tech news letters to someone who’s. Part of the clubs, right. if you’ve got all these other newsletter creators who are sharing your work as a great example, you come up in conversation like, Oh, talking PARA who I was talking to.

It was Jason from Pico and I, and a few other people chatting. And there’s like, everyone’s just like, Oh, we love Mario’s stuff. Right. Has, has that been a shift for you? Or like, is there anything pricing in that shift of going from the consumer to like part of the creator clubs?

Mario: [00:07:20]
For sure. Yeah. I always, it always feels like a little bit of a trip. Like for example, last night, on Twitter spaces, me Packy McCormick, and of Not Boring and the two hosts of Acquired, David Rosenthal and Ben Gilbert. I’ve been listened to Acquired for a long time. I think it’s an amazing podcast and Packy and I sort of have come up at a similar time.

And I remember talking with Packy about it offline. And I was like, man, isn’t this a trip that like, we get to jam with these two guys that a year ago or 18 months ago, we were just like really admiring their work. and I think that the real takeaways for me are just that like, One, the Content can really speak for itself as long as you are putting in a ton of work and, being really, really, really consistent about it.

And that just like can accelerate you way faster than you might’ve imagined. I think, I constantly underestimated what I might be able to achieve alone as a solo creator. Both in terms of like, you know, traditional growth and just in terms of like being a part of these conversations.

Nathan: [00:08:33]
Yeah. I mean, that was exactly it for me, you know, and this is back in probably 20, 2012, 2013 of you just go from all the people that you read in mire. And then, you know, at some point you realize like, Oh, I’m, I’m part of the group. How did that happen? And it really, it, I mean, it just comes from that. There’s not this huge gap between the person consuming the content, the person creating it.

It’s not like the creators, this legend or anything like that. It’s just like, Hey, just showed up and, and made stuff. And it works really well. Yeah. something else that I was thinking about is you mentioned like your career, you know, so working in, in tech and then getting into venture, and then as you start the newsletter, right?

There’s a couple of different paths. There’s a lot of venture capitalists who have newsletters and, you know, drive incredible deal flow. So like that’s one path. It doesn’t sound like that was your primary path. You’re like looking to. You know, leave venture and, you know, be a full-time, newsletter creator.

But one thing that I, that I was thinking about is there’s probably no faster way to accelerate your career than to go create an online presence. Go create a newsletter and teach and everything, because maybe you could just speak to this, like the amount of time it would take to move up through venture versus like, short-cutting that entire process by building your own audience.

Mario: [00:10:05]
A hundred percent and it’s sort of frustrating because it’s a piece of advice. I think a lot of people will give you early on in venture, which is like, Hey, you should really start blogging and like building an audience. And even for someone like me who was like writing every day, regardless, I still always discounted it as like, yeah, but I mean, what do I know I’m new to this industry?

You know, there’s so many other people writing about this. Like there’s no way I’m going to generate an audience. I have to wait until I know a lot more. and I’m already a partner for anyone to care. And the truth is like, it’s the opposite. It’s the, you know, obviously a partner can generate that interest maybe off the back, but they kind of don’t need to, and there’s way fewer impediments to you, gaining that audience than you think.

So. Yes. I think one, if I was starting my venture career, earlier on, I would’ve just like started a regular newsletter off the bat and recognize that like the quality curve would be hopefully, you know, a little steep. and the first, you know, it would take a little bit of time to get up and running, but yeah, I think if you wanted to start a fund today, I would probably start with audience and Content first.

And I think writing is. Probably the best thing, for, for tech, I mean, definitely there’s some great audio formats as well, but, I think for some of the complexities of tech, writing is particularly good for it.

Nathan: [00:11:39]
Yeah. What’s interesting. Is as people dive into this, well, I speak for myself when I start something new, I’m always like, Oh, what if it fails?

And so I always like kind of map out what, what does failure look like? One, the, the true failure would be that you write like three essays or something, and then you just stop. But let’s say that I write an essay a week or even an essay a month for, a year. Like my worst version of failure in that is that I’m going to have some number of people paying attention to me.

And then the next time I apply for a job that they’re scrolling through and they’ll click to my website. And instead of seeing like something that was updated in 2016, they’ll be like, Oh, He can write, he can communicate these they’re interesting ideas. He seems proactive, right? That’s one like actual worst case scenario.

If you show up is that it will make you more employable. And then the second is like, it would meaningfully accelerate your career. And then the third, you know, the third option is like, you could actually have a path forward as a creator. And that’s where I just, I mean, I encourage everyone to write.

Mario: [00:12:48]
Hundred percent. Yeah. I mean, as you said, at the very least, it’s an extremely valuable skill to have and will make you better at your job and, and more attractive to others. And, you know, on the outside or, you know, frankly, probably more accessible than, than many of us realize, like it can really be a career in and of itself.

Nathan: [00:13:08]
Yeah. What, what advice would you have for someone who maybe is in tech is consuming all of this content, and doesn’t have that writing background, you know, and it’s like, Oh, but I’m not a good writer. How, how should I practice? What should I do? Yeah.

Mario: [00:13:23]
I mean, unfortunately I think there’s sort of no huge shortcuts. I think it’s all just like putting the work into, to keep getting better. and for writing specifically, I think. No, you got to just like show up and do an hour, or at least, you know, some amount every day or at least a few times a week, I think, to get really good.

And I’m still very much on the path where I feel like I have a lot more to learn. I hope to keep improving and like honing this muscle over the course of my life. and then, you know, you have to read really widely, I think. and in particular, my, Evangelism is I think people should read much, much more fiction.

Then is common in business circles. and in tech circles in particular, for a few different reasons. One, I think like a great deal of nonsense section is essentially a Podcast of an app power that has been, you know, bloated to eight hours. and that you can really get most of the meat in a short amount of time.

This is not always the case, but I think it’s a good amount of time, the case. And second, like. The cadence and imagination and insight of fiction is like, has a less expressible ROI, but it doesn’t mean it doesn’t exist. It’s just because it’s like more ineffable. and so that is the other thing that I think like hugely helps.

My writing is like, because I very, very rarely read nonfiction and has been obsessed with fiction for years. I think that at least helps me stand out from a storytelling perspective.

Nathan: [00:15:06]
Right. Is there, if you’re trying to hook someone into the world of reading fiction, what are like one or two, series that you would start with?

Mario: [00:15:15]
I would say my favorite writers are, Ian McEwan, an English author, most famous book is called Atonement. Like I, I think that’s a pretty accessible book and really awesome. He has a very, very short book called, On Chesil Beach, which is like a beautiful small novel. I think like Murakami has a great book called Norwegian Wood, which is weird, but not like full-bent, Murakami weird.

So I think it’s like a good intro book as well. but yeah, I think all of those things like. When you’re writing about tech or anything else, having a story to frame this may be more wonkish world and makes it so much more accessible and interesting. And I think helps build an audience.

Nathan: [00:16:00]
Yeah, that makes sense. Something that you’ve done with The Generalist that I think is really interesting is you’ve brought in, like fellow writers. You’ve made these clubs to try to, get a lot of different people’s takes, but it’s also play this role of, Getting more friends and advocates for The Generalist and, and participants it’s it reminds me of the advice that YouTube would always give to YouTubers of saying like, go and do collaborations.

That’s the best way to grow your channel. And you’ve like, systematized it. where did that come from to do it? The S–1 Clubs.

Mario: [00:16:38]
Yeah, so I think initially it was like pure happenstance that. Things were constructed in such a way as to be so collaborative. I think it was probably ultimately came out of, you know, a strength than a weakness. Like maybe the strength is that I really do enjoy, meeting with other people. I really enjoy learning from other people.

I try as much as possible to like, listen less than I. And I sort of speak. and then I would say the weaknesses, you know, from a perspective of insecurity, you know, especially as you’re starting as a creator, for me as a VC, what about like a large public company? I was like, Oh, I’m not the guy who did two years of investment banking or, you know, work that a hedge fund, like my really going to be able to break down this business.

Well, but I clearly want to like talk about it. So, how do I like make this amazing? and what I think I learned after sort of the early version of all of this and also RFS, which is like also a collaborative, sort of, project. Is that just like. Yeah. So RFS is, basically my Friday email, every Friday, you get five startup ideas that are curated from some of the best and brightest VCs and founders from leading firms around the world.

So you’ll get like a GP of Andreessen Horowitz sharing a startup. They hope it gets made, or. You know, the CEO of like a unicorn company being like, if I wasn’t building this, maybe I would like, think about building this. and so I think it’s, you know, helpful, hopefully for folks that are just sort of going down the idea maze.

I think like, you know, at the times when I’ve considered maybe starting a software business, and I think flick anyone in tech has vaguely, entertain those thoughts. I was always like keen for vetted ideas. and so that sort of this, the premise of this, but again, it’s like fundamentally collaborative there I’ll share some ideas of my own, but really they’re everyone else’s and I’m just sort of playing the role as curator.

Anyway, all to say that. It sort of came about by accident, but I think to your point, like very quickly early on looking at folks, that, that use YouTube and even audio, it was just like very obvious that collabs help you drive growth in a very different way. And I think they also. Create a very different product, that feels differentiated.

So, you know, increasingly the way I think about The Generalist is like a multi pelt, a multiplayer experience that you’re tapping into. so I, I need to do more work on that, but, that’s like informing a lot more of my strategy at the moment.

Nathan: [00:19:37]
Yeah. I’m just realizing so many creators do it as a, as a fully solo activity, which could work really well. And a lot of people, you know, grow quickly, or like they have the brand of the newsletter as, as their name.

But. Like the thing that I noticed about The Generalist is how many people are like in your corner rooting for you and, and for the amount of time that you’ve been doing it, right.

We’re two years into this, not even 18 months, basically. Right. and so, and I think that this, as you described it, the multiplayer experience is a big part of it where you’ve built in these two systems where it’s not just like. Hey, we’re fellow creators. We’re all in it together. Like, I’m commenting on your story and saying, Hey, I particularly love this one.

Or that kind of thing. Cause we’re friends are interested in similar things. It’s, you’ve actually built in these two systems of the S–1 Clubs and the requests for startups that are every, you know, every week, sometimes we’ve asked one club four or five times a week because it’s been wild. And I’m just thinking about how other people could do that.

Like, say if you were writing your newsletter every Monday at Monday and Wednesday, and that was the thing that you were writing, but every Friday, you know, you’re going out and you’re saying I’m. Doing like, and you just make sure your readers know this, I’m doing a cross-post from one of my favorite writers.

And so it forces you to do two things, one, go out and meet new people. And then like, to the people who you follow it and admire, like you actually send them the email and be like, Hey, do you want to collaborate? Because I need, I need someone to fill the slot. And I think it really accelerates growth.

Mario: [00:21:31]
I totally agree. Yeah. I mean, again, Packy I think did a really great job with this, with his Thursday post. Like he writes a Monday post and a Thursday post, and sometimes he writes the Thursday post, but a lot of the time, it’s someone else who, you know, is an expert in something. So. he had, I think one of the founders of managed by Q talking about sort of like the, the new sort of food ecosystem and logistics, and like, this is someone who’s clearly thought about the future of cities, the future of spaces very deeply.

And you know, maybe that Dan isn’t running a newsletter, but still takes a lot of value in sharing his thoughts. with an in-built audience and Packy derives the benefits of, you know, his audience in turn. So I definitely think there’s many, many ways to do it.

Nathan: [00:22:20]
Yeah. Are there other examples that come to mind of, creators who sort of have that collaboration built in?

Mario: [00:22:27]
The, the one that comes to mind beyond that is not newsletter newsletter related. I would say the, have you ever listened to the All-In podcast?

Nathan: [00:22:36]
Yes. Yes.

Mario: [00:22:38]
Yeah. So like that sort of now has just become sort of another Podcast. But I think at the beginning, like really sort of emerged from that same spirit of like, cool, we all have these, these separate audiences, like let’s come together and see what happens.

And you know, now it’s a piece of content in and of itself, but, I think it sort of emerged from that same feeling. but yeah, I don’t, I don’t know a ton

Nathan: [00:23:02]
so for anyone who doesn’t know that all in Podcast that’s, Jason Calacanis and and, who else. David Sacks.

Mario: [00:23:09]
Freeburg and David Sacks.

Nathan: [00:23:11]
Yeah. Yeah. And I feel like it just started as them. They had like, they want to talk about specs maybe. I don’t know.

Mario: [00:23:19]
I think so. Just like kind of shooting the shit. Like I don’t, I think it was, just Jason and Chamath to begin with. And then they sort of just like brought in the Davids initially as sort of guests that sort of morphed into full-time, you know, co-hosts but I think, you know, there’s lots of ways to do that with, with newsletters.

One of the things that like, I really want to try out soon is. a debate in newsletter format. So take another writer who writes about tech, find a topic where we have a genuine disagreement and, you know, sort of interrogate the two different sides in writing in a newsletter that we both shared with our audiences.

And so finding conversation in writing I think is, it’s something I’ve found really, really useful.

Nathan: [00:24:14]
Would that makes me think about, is like all of you think about collaborations as one plus one equals two, right? Where you have your audience, I’ve got 20,000 readers, you’ve got 20,000 readers and we’ll we’ll cross promote, and we’ll both get this bump and that’d be great. The debate that you’re talking about.

Goes and make something that’s bigger than the combination of the two things. Right? You have multiplicative effects because now it’s like, Oh, did you see Mario? And whoever debate that, like, it was so good. And it, because, you know, we both have big enough platforms to get some level of attention, you know, then the fact that the debate is happening turns into a larger thing and it is its own event.

And then we might get way more attention.

Mario: [00:24:59]
Yeah, I think that it adds a fun, fun element in general. I would say that like my, practice for collaborations now is always about pulling someone in to make a piece of content together rather than I think it can be fine to cross-post to, and I bet that like works really well, but I especially enjoy it when I can say to someone like Greg Eisenberg, who, you know, is the founder of late, late.

Check-out really thoughtful about community. Has written and shared a lot of public’s thinking about Reddit, where I can sort of like tap him and be like, Hey, I want to do a deep dive on Reddit and why it’s this crazy undervalued company? Why don’t we do it together? and so, you know, that’s something we released over the weekend, but I think it was a good example of like, I don’t think alone either one of us would have made it as good as it became.

And, you know, it was, it was valuable for both of our audiences and still achieve the same growth bump.

Nathan: [00:26:00]
That is interesting. I feel like I have these topics that I riff on with friends. Like for example, I wrote a post called the ladders of wealth creation, which is an idea that I started with and then got input from, from friends, but like probably a third of the ideas in the post or more are from James clear and like him and I riffing on it.

And so that would be the same sort of thing of like, I guess finding those topics that you, you know, you and that particular friend are talking about, you’re both obsessed with and just say, let’s go make this together. Cause then the other thing that we’ll do is then the two of you, like, you have to promote it more because you wrote your friend into writing it, you know, you can’t be like, Oh, that’s just the Thursday post.

I got it out. Cool. What’s onto the next week. You’re like, I pulled my friend into helping write this. Like now we’re both going to actually promote it and share it and make it worth while, which is of course better for everybody.

Mario: [00:26:53]
Yeah. And it also just like leads itself to Content extensions more easily, right? Like you can then have a conversation around it in a clubhouse room if you wanted or something else. And like, you already have this other person who is like deeply invested in it with you. and like, you know, you get that conversational aspect to it.

Nathan: [00:27:14]
Yeah. Do you have like a list of people? that back when I did a lot of sales, I for ConvertKit, I would have like, sort of this dream 100 list of people that I wanted to have on ConvertKit or like, do you have that for collaborating?

Or you’re like, okay. Here’s who I want to reach out to, but I’m a little nervous to send the email or something like that.

Mario: [00:27:33]
Yeah, I have, I have a list like that where I would say it’s not so much that I’m nervous. I’m just like, I have to know. Exactly what the right project is. so for example, a person whose newsletter I love and I’ve collaborated with him on an S one club, is just engage, who writes technically great newsletter.

And like, I know I want to do a collaborator with him, but I didn’t have a clear idea until recently where I was just like, okay, this is it. And so we’re going to, we’re going to do something that’ll come out soon. and so I think that’s the, that’s the pitch. And then sometimes, obviously like I’ll pitch someone an idea and they’re like, eh, I I’m too busy or but that’s okay too.

Nathan: [00:28:18]
Yeah. Well, that’s good. I think having the list written down like potential ideas and then people you want to collaborate with and just keep adding to those. And then sometimes they overlap and you’re like, you know, or you’re like, I really want to work with this person, but I don’t have the right idea yet.

And then when the idea comes, then it’s like, Oh, I got the perfect thing.

Mario: [00:28:37]
Exactly. Yeah, I think it, I, I definitely like having the list because it also just like, even just writing that list, it gives you so many ideas.

Nathan: [00:28:44]
Another thing about the lists is sometimes I like anything that will be a snapshot of like your current, a worldview of what’s possible.

So for example, early on for ConvertKit. That list had people like Tim Ferriss, Gretchen Rubin, other people as like who to get as customers. And so when you write that, when you’re like, Oh, it would be insane to collaborate with this level of person. And then like a couple of years later when it happens, you’re just like, Oh yeah, well like their peers, you know, of course we know I have like 10 friends in common, so we just finally made it happen.

But by writing it down, you get to have the snapshot of like, Past me thought this would be incredible, you know? And so just like you’re talking about with, you know, wrestling with the guys on the, on the Twitter spaces the other day.

Mario: [00:29:33]
Yeah, a hundred percent, I think. well, there’s, there’s some, I think it’s Aristotle, or one of the, the old philosophers, which is like, you know, the, I can’t remember the exact quote, but they just have, it is essentially like, don’t forget that you have things that you once desired greatly. and like, I think that’s often the case where you sort of, treat happiness or pride in your work as a moving target that is really fleeting.

And those lists, I think, help remind you that like, yeah, it wasn’t that long ago that the idea of collaborating with this person or having this person send a nice note about your work would have like blown your mind. and now it’s like, cool. Yep. That’s awesome. Next.

Nathan: [00:30:28]
Yeah. Yeah. For sure. One of the things that’s really impressed me about how you’ve grown The Generalist is you’ve taken it really seriously. I don’t know if it was from the beginning, but from the point that you and I met, which was probably what maybe April or may of last year, June, somewhere in there.

Yeah, that sounds right. And to the point that you, talk to, did you recruit a formal, like board of advisors or informal advisors?

Yeah. But you, you had a pitch deck for it. You outlined the business model. like what made you take it so seriously rather than, you know, kind of be like, Oh, Write every week and see what happens.

Mario: [00:31:11]
Probably a mixture of like personality defects and, excitement. I think like, 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 honestly, like I would say that switch had not. Been flipped in me since college, like as a student, I was an absolute animal. Like, that’s not a very cool thing to say, but I was just an absolute nerd. I was a relentless studier. Loved it. And, I think it was because. You know, I felt very empowered to study whatever it is.

I wanted like go as deep as possible and feel like the value was accruing directly to me. and I think the struggle for me as an employee was always like, I’ll give you 90%, but I don’t want to give you a hundred percent because like, I kind of need the 10% to do something of my own or, you know, because I sort of resent it.

And so. As soon as I was like fully on my own thing, I suddenly felt like, Oh man, I’m unchanged to go after this. and then I think the second piece of it was just that, I wanted to convince myself to a certain extent, that this could be real. And so making a business plan, bringing on people who I felt like could support and advise me and like make me better.

All of those things started to convince me that. Okay. And maybe you’re not crazy. Like maybe other people seem to see something interesting here. and your math adds up more or less that like, maybe you can make this work.

Nathan: [00:33:08]
Yeah. Yeah. I think that, well, one, if you’re looking for advice from anyone showing that you’re already in motion and that you’re going to make it happen, like the number of people who reach out and say like, could I pick your brain or whatever else?

And they don’t have any track record that they’re going to implement it. You know, is, there’s just, there’s so many. And so when someone comes along, who is like, Hey, I need advice on this specific thing. And you’re like, yeah, there you go. And they take action. And then they come back like a month later and be like, that works really well.

Hey, could you help with this? It’s sort of addicting to help those people. And that’s what I found early on for ConvertKit where people like Amy Hoy and Heaton Shaw and Patrick McKenzie, and so many others would come and help. Because I would like immediately turn around and try out the

Mario: [00:33:55]
Do it.

Nathan: [00:33:56]
That they said. And I see you doing the same thing.

Mario: [00:33:59]
Thanks, man. Yeah, I definitely try to, I think it’s, you know, early days you just got to keep a pretty high velocity as much as you can.

Nathan: [00:34:07]
Yeah. So let’s talk about growth. if you’re up for it, I’d love for you to share some numbers of where The Generalist is at now. And then we can dive into, how we got there on the growth side.

Mario: [00:34:19]
For sure. Let me actually pull up the, the live, the live look so I can be exact, ConvertKit tells me I have 27,147 subscribers. So thank you to every single one of them. And opens are 53.52,

Nathan: [00:34:43]
That is a very impressive open rate.

Mario: [00:34:45]
Thank you. Thank you. it’s weird. It went up as I’ve grown, which I did not expect. Now it’s more or less stabilized, but I think when I went full time, it was at like, I dunno, I have to look at the deck, but somewhere around 49 to 50. And it’s now con consistently above 53. I mean, it’s a small improvement, but like, I like to see it.

Nathan: [00:35:09]
Well, I mean, especially when you multiply it out over a larger, you know, a growing number, right. When you multiply gets 10,000 versus 20,000, It’s a lot more. and I always encourage people to track engaged subscribers as like their metric, you know? So total subscribers times open rate, because then when something comes along, like if you have hung your whole like, self-worth on, total subscribers, you know, and then it comes along and you’re like, Oh, I got these 10,000 who are just dead weight and don’t open anything.

And you’re like, I can’t cut that because like having a newsletter of a hundred thousand people is like, Part of my identity or something, you know, but if you’ve been focused on engaged subscribers, then you’re like, I don’t lose anything if I cut those people.

Mario: [00:35:53]
That’s really? Yeah, that’s a, that’s a great point about just like tying it to your identity. I love the engagement score you guys have, by the way. I don’t know if I’ve told you that, but ah, so nice to see that.

Nathan: [00:36:03]
Yeah, it’s a fun, a fun little feature. And then on the, so you went, you went full-time in August about six months ago. how’s it been on the revenue side?

Mario: [00:36:16]
So I didn’t, monetize until. One month ago, almost exactly. It was January 24th. so that was the day I opened up memberships and was also, shortly after I started to like circle back to a few folks that have been interested in advertising and sponsoring in the past and was like, Hey,

Nathan: [00:36:37]
There, there was no way to pay you or for you to make money from it up until that point?

Mario: [00:36:41]
No, it was all free. and honestly it was like, There wasn’t probably a good reason for that. I think it was partially because I wanted to build a little bit more of my own stack with Webflow and Pico. And of course you guys, and I didn’t want to start it on sub stack. I was already switched over at this point for a long time.

And so I wanted to have like a really awesome site and home for the Content before I switched on memberships. And it felt a little bit strange to accept sponsorships before that point, just because it wasn’t really the way I expected to make the majority of revenue longterm. so yeah, flipped it on, on January 24th and, it’s gone really well so far.

Nathan: [00:37:33]
Nice, nice. You were mentioning like how it compares? This is before we were talking, how it compares to, you know, past salaries, Do you track that? I guess like percentage of salary?

Mario: [00:37:47]
Yeah, I think that’s like a nice way for, for me to look at it. and this definitely validating. So in the first month, I have to check, but it’s something it’s around 85 to 90% of my best ever salary. In the first month. So that was like, I know it’s not always going to be like that. I think there was a huge, like initial bump and because of the types of memberships I did, like, I have a believer membership where someone buys five years effectively upfront.

There’s a bunch of like essentially bookings pull forward, but still the growth has remained really good throughout the month. There’s still a good base of people who are on this sort of monthly or annual plan. And it really feels very much like it can be a business. So, you know, it’s now really up to me to make sure I don’t blow it. And you know, just keep executing as well as I can.

Nathan: [00:38:48]
Yeah. I mean, that’s exciting to have that much traction, like the moment you turn it on now, like, as you said, you waited awhile to, to monetize right.

Of having, you know, well over 20,000 subscribers, by the time that you turned that on, but it means that you can come out and have this big splash, which is great.

Mario: [00:39:04]
Yeah, it feels, it feels good to like get, get a, sort of a nice bump to it. But I think there’s plenty of other people who start much earlier on and then, you know, that can work wonderfully as well. And you probably get a lot of interesting learnings. From, you know, monetizing early, finding out what people actually are willing to pay for.

Like, those are all things that I’m now just learning, which is like, cool, what should be in front and behind the paywall? You know, what’s the sort of messaging even that converts people, because I really haven’t spent time thinking about that today.

Nathan: [00:39:37]
Yeah. How did you structure what’s in front of him behind the paywall? cause that’s something that I think a lot of people run into of I’m putting out this content and it’s really good. So it should be behind the paywall, but I want it in front of you in front of the paywall so that it can help me attract more readers.

Mario: [00:39:55]
Yeah, the tricky thing I would say is that because of the, like multi-player elements of The Generalist, it’s not that easy to put a lot of the content behind the paywall, because the people who contribute on an S–1 Club, like a lot of them are. The GPS of a venture firm or a CEO or an expert, like they’re doing it because they’re really interested in this subject and genuinely want to share their thoughts and trade ideas with other smart people, to limit the view of it feels like probably against their interests, even if I’m not sure they would necessarily.

Express an issue with it, but it kind of doesn’t feel totally right to me. so those things I think are easy to put in front of the paywall and those are things also that are easy to monetize with sponsorships. So that’s great. then there’s, I would say like a lot of more intimate or deep content that goes behind it.

So every Sunday folks get a briefing from me, which dives deep into some. Area of tech or the financial markets often it’s, you know, sort of unpacking an investment that I think might be interesting or a technical trend that I think is worth keeping in. and you know, or free members, free subscribers get one of those a month and paying subscribers, get four of them.

And then the other piece of it, I would say is, you know, there’s a bunch of other parts, but the, the core. Element, is this community, so I now have a, a community which is only for, for paid members. it’s ended up being like very senior impressive group of folks. and so it has more of a feel of like a private conversation.

That’s ongoing with people that it would be probably like hard to get access to otherwise. that I think has also proven like a really. Useful conversion tool and also a, something proves the content itself because often before I write something, I’ll post about it in the community and then five or 10 people will say, Hey, have you thought about this?

Have you thought about that? And so it sort of has a nice, nice effect in that, in that regard too.

Nathan: [00:42:22]
Yeah. And is that a community that you’re hosting on circle or Slack or somewhere else?

Mario: [00:42:27]
Yeah, circle. I thought a lot about, you know, where to host it. Ultimately I felt like circle was going to be the best call and, and so far I really like it.

Nathan: [00:42:37]
Yeah. It’s been interesting of, of seeing communities become such a core part of a lot of newsletters. have you found, like, are there any downsides to it? Is it a pain to manage? Is there anything else or has it just been all upside?

Mario: [00:42:53]
I don’t think anything SaaS, upside, I think like, you know, everything, everything has downside. the downside of community is time. I think. it’s just, I don’t think it works if you just sort of flip it on and expect it to take off. And actually I think like that’s potentially a trade-off versus. live chat platforms like discord or Slack or telegram versus something that’s asynchronous like circle.

If you start a Slack group with 50 people, it very quickly feels busy and lively. once you hit 500 people, it very quickly feels noisy and chaotic. Whereas I think circle is sort of the other way around, which is, you know, 50 and maybe feels a little sleepy. and so you have people sort of like. Maybe looking for how to get the conversation going.

But my hope is that really, as you scale, it leads to more focused, thoughtful discussions rather than just sort of like incessant back and forth and people like self-promoting stuff in this channel all the time. and those sort of things. So the, the trade off is time.

Nathan: [00:44:05]
Yeah. Yeah. That makes sense. And so I could see circle being something that you have to grow into. Whereas Slack being something that you would probably grow out of. And so that’s a good thing to think about, of like, what’s the long-term play for this community. And are we going to get into that, you know, 500 members and beyond, and if so, like go for a platform that’s a good fit for that.

Mario: [00:44:29]
Yeah. I ran a bunch of like Telegram groups on the side that weren’t like formally part of The Generalist, but I would, as part of the Friday startup ideas newsletter, like allow people to join this group if they applied, And it was great. I really liked it. but at a hundred people, it was already occasionally like quite noisy.

And I didn’t think it like created a compendium of knowledge in the same way as something like circle can where you can suddenly search like, you know, RPA. And there will be a really interesting thread that someone wrote and bunch of smart people commented on that, like is now this living document, in a really scannable way.

Nathan: [00:45:11]
Yeah. That makes sense. What about pricing? how did you come to the pricing that you chose?

Mario: [00:45:16]
Yeah, I actually, I want to write about this. probably not in the newsletter, but, maybe on Twitter or something, to explain it because I think people it’s either two reactions. Either someone thinks it’s a total no-brainer at 19 bucks a month. and you know, sometimes even folks will be like, I think you could push this higher off the record.

Or you get folks that are like, why is this 19 bucks when Netflix is 12? and The Economist is 12 or whatever it is they are at. and the answer really is like a few different things. But one is that I think I’ve engineered as much as possible. The Generalist to be able to return your value like 10 or 20, or, you know, maybe even a hundred fold.

In a few different ways, like the ways that I think someone gets to the point where they are really like ripping me off, let’s say, is if I can get them into a company that they think is really interesting and investment that they think is really interesting either in the public or private markets, that I helped them find a co-founder or a key hire for their existing company.

That I give them a startup idea that they then are able to use to build their next company. or I introduced them to just like an amazing colleague, whether that’s another investor or, you know, a fellow founder, whatever it is. And so in each of the pieces of content and the community, I think there’s the potential for that.

So you have the Friday newsletter, which has five startup ideas. If one of the, you know, 150 that I think we have right now from these great theses and founders, like resonates with you or gets you closer. I think it’s a total no-brainer it was obviously worth 20 bucks a month or 19 bucks a month. if the S one club helps you make a smarter decision about whether to invest in a stock or not.

No brainer. If the weekly briefing gives you either, again, a stock that you’re interested in or a private investment that you might want to make as a VC again, no brainer. and then the community, hopefully like stitches a lot of those pieces together where it’s like, cool. I know that you were interested in this startup idea because you told me about it.

Now it’s time for you to meet this engineer who like also said they were interested in it and like, maybe you guys should jam on that. and so this is something that I sort of tried to outline in an interview. I did with Alex Danko who writes one of my favorite newsletters. And it’s just like one of the smartest people in tech, in my opinion.

I think there’s a real. sort of almost mismatch in how consumers pay for a newsletter and how they receive value. Like consumers pay on this really linear timescale. It’s like 19 bucks a month, 19 bucks a month, 19 bucks a month. Realistically, you probably won’t read every piece. I write if you’re a subscriber.

And you probably won’t see like every comment in the community, but as long as each individual piece of content has the ability to be worth like. 500 bucks or a thousand bucks to you. Like, I can take it my time. Hopefully if you’re willing to be patient as a reader and you might not read one, two or three, you might find four boring, but then five might give you your startup idea or, you know, in the six week you might meet your cofaq.

So I think there’s like a linear line on the consumer side and a super lumpy one on the value realization. so that was a very. Inside baseball, look at how I think about the pricing, but, that’s sort of where my head’s at at the moment.

Nathan: [00:49:12]
Yeah, that makes sense. if you know some of this other stuff you had, what was some of the split between like monthly and annual and of course you probably launched your biggest fans.

And so it’s probably going to be a higher split annual. Upfront,

Mario: [00:49:25]
I don’t, I don’t know what it is actually. I think when I looked last, and this was a few weeks ago, so it’s like a little bit out of date. I think I would make 5% of my best salary per month. So it wouldn’t get me there on a yearly basis, but like, you know, would get me part of the way there. And then plus the annuals I’m yeah.

I’m not sure what the split is. There was a good amount. I want to say maybe 10 or 15%, maybe as high as 20, that were believers. people who bought the five years upfront and, that is like amazing for me. One, because like, It’s very nice that people like are excited to be a part of this for five years.

And to also, because I think it hopefully allows me to like, reinvest that money in, in continuing growth.

Nathan: [00:50:29]
Yup. Well, I love that you gave people that option, you know, like I think someone who would launch just with monthly and say it’s 20 bucks a month and then go like, okay, I guess I should have an annual version. People say that churn is better, so sure. I’ll do that. And you’ve added this, this third tier of saying like no pay, is it $600?

Something like that.

Mario: [00:50:50]
Yeah, it’s a $642.

Nathan: [00:50:53]
$642, you know, just say like, Hey, all of this upfront and the way you message it around, like, you know, the believer tier, I think is really good. Cause for a lot of people. Especially in your audience, right. You’re going to have the whole range, someone who’s going to be like, Oh, 20 bucks a month. Yeah, no, it’s worth it.

Like, I’m going to go for that. And you’re going to have other people who are like $600. It’s it’s going on the company credit card. Like, it just doesn’t even, it just doesn’t even register. And so, but that person would have given you $20, if that was the only option you’ve given them. And so

Mario: [00:51:25]
A hundred percent.

Nathan: [00:51:26]
Always give them the other options.

When I was selling eBooks, I would do, like. Books into courses and do tiers and your $39 $99 and then $249. And like a quarter of the people bought the $249 options, but it represented like 55% of all revenue.

Mario: [00:51:46]
There you go. There you go. Yeah, that makes sense. yeah, people have asked like, Oh, are you going to get rid of the believer tier soon? And I’m kinda like, I don’t really think so. I think I’ll just like, you know, maybe as prices change, maybe I’ll adjust it or something like that. But like, if someone is excited to sign up for five years, like,

Nathan: [00:52:05]
Right. I might even play with it of decreasing the, like, if I think if I were flying with this, I wouldn’t do five years.

I would do two years or something like that. And maybe there’s some other perks in there. but it is this high price that renews, like what if, what if the believers here was a thousand dollars a year? And maybe it has some extra things in it, but it really is like the believer tier. And I don’t know if they would go for it, but I’m curious if they would, and if I were doing it or maybe it’s $400 or $500 a year. And I would just be curious if people would sign up for it, my guess. Is that, that some way

Mario: [00:52:49]
I think you’re probably right. I’d love to get to the point where I can like more explicitly message. What are the things I’m doing for those people right now? I’m like, cool. You get fast-tracked into the community. You are going to have some like extra events and channels within the community. So like, you’ll have these moments of intimacy that like you are sort of getting, because you are so, such a believer in this, but I think you’re totally right.

Like, it probably is, is something I should think about of like, how do I build that extra two 50 or 300 bucks of value for someone on an annual basis that, that makes it worthwhile.

Nathan: [00:53:31]
Right? Yeah. I would even, you know, put a badge on their profile in the community, you know.

Mario: [00:53:37]
It happens.

Nathan: [00:53:38]
Oh, good.

Mario: [00:53:39]
Yeah. I’m a big believer in badging.

Nathan: [00:53:44]
At all.

Mario: [00:53:47]
I think people like it and I think it’s fun and, you know…

Nathan: [00:53:50]
Yeah, good stuff. Well, thanks for coming on. This has been really fun to dive in and talk through all the details of The Generalist. Where should people go to subscribe and then to follow you around the web?

Mario: [00:54:00]
Awesome. Yeah. you can sign up, ReadTheGeneralist.com, and, I’m mostly active on Twitter. So, if you look up @mariodgabriele, on Twitter, That is me.

Nathan: [00:54:15]
Sounds good.

Mario: [00:54:16]
Know, still free to shoot me a DM or an email sometime.

Nathan: [00:54:19]
Perfect. Well, we’ll link to both those in the show notes and we’ll chat soon. I’m excited to keep watching, watching the newsletter grow.

Mario: [00:54:26]
Thanks man. Well, fingers crossed. I can, I can continue to deliver and that, you know, I have to thank you. And, and the team so much for one making a dope project, a product, and, to helping so much along the way with your advice and support. So I appreciate it a lot.

Nathan: [00:54:43]
My pleasure.