Welcome back to The Jungle Gym – a newsletter that shows you how to build a more fulfilling career by integrating your work and life.
Every other issue of this newsletter uses a format called: 🗝 The Keyring. It features interviews with domain experts about the tools, methods, and frameworks they use to make progress in their careers.
For more context on what The Jungle Gym is all about, check out this introductory post.
And, if you're not a subscriber yet, and want to sign up for future issues, enter your email here:
I’m usually good at avoiding professional jealousy.
Fortunately, Mario is also one of the kindest people I’ve had the pleasure of meeting. In an industry where many give off the impression that they are the most impressive person you’ve ever met, Mario makes you feel like you might just be the most impressive person he’s ever met.
Given Mario’s busy writing schedule, I feel fortunate that he offered to share the routines, tools, and frameworks he uses to make progress in his career.
The Day to Day
Explain your job to me, like I’m five.
I write about things that change really fast.
Walk me through a normal day. How do you spend your time?
I typically get up between 6 am - 7 am, depending on how much sleep I’ve gotten recently. I try and give myself leeway, especially now that I don’t have to head to an office.
As often as I can (i.e., when I’m not slacking), I’ll workout. For the past year, I’ve been using Future, which provides me the accountability to get in a run or HIIT session. I’ve also been experimenting with the WHOOP band, which has been a fun way to chart the intensity of that exertion.
After that, I’ll take a cold shower, which I’m a bit self-conscious to note on the chance it portrays me as the type of tiresome, self-congratulating ascetic tech person whom we have all met. I have no answers or nifty “hacks” that will “10x” your mental horsepower. But I do enjoy cold showers, mostly because of the test they provide — starting the day with an act of discipline helps me.
Before I start work, I write fiction, usually for about an hour. Since late 2012, I’ve been working on a novel. Before I went into tech and venture capital, I very nearly matriculated to an MFA program. The novel is (very) loosely based on the time I spent living in Kathmandu, as an undergraduate, though transported to the near-future. I must have finished writing it five times, but still, I think I can improve it, which stops me from soliciting a publisher. At some point, I hope I will have the conviction to share it.
This hour has a strong impact on my mood for the rest of the morning. If I feel as if I am in form, fluid, thinking interestingly, and writing decently, then I feel as if the day has not been wasted; at the very least, I will have tapped into the original parts of my brain. I can carry that into whatever comes next.
Typically this involves a mix of research, writing, email, Telegram, meetings, and social media. In a way, I find each of these activities very fun. There is nothing I would rather do than build The Generalist — that clarity, that conviction is something I have not had previously.
What does a typical week look like?
When viewed on the timescale of a week, a certain shape emerges.
Monday is a gentler day, coming as it does after I send my weekly essay. It is, much of the time, the closest thing to a weekend (I do not mean this self-pityingly; it is fun for me to work), which means I will spend the morning responding to readers, taking a look at metrics (growth, open rates, unsubscriptions), and sharing my work on social media.
If I remember rightly, James Clear suggests spending as much time promoting a piece as you spent working on it; 1:1. That’s something I’ve been trying to be better at. I’m probably closer to 4:1 at this point, but a year ago, it would have looked closer to 20:1. In the afternoon, I’ll usually try to get a draft of RFS cued up, giving contributors a chance to review their idea a final time.
Tuesday is a great day to work on secondary projects. The stress of the upcoming essay has yet to start in earnest, so I feel the freedom to dream a bit. I’ll often spend a good part of the day meeting readers, other writers, venture capitalists, and founders. Increasingly, I’m trying to concentrate on meetings in the afternoon, just a few days of the week. This isn’t because I don’t enjoy these discussions — they are almost always enjoyable and informative. But writing has high switching costs, at least for me. I need time to get into the flow. Once interrupted, it takes just as long to regain it. So for the sake of efficiency, long stretches of unbroken time are desirable.
Wednesday, I write. My calendar says, unflinchingly, “The Big Write.” I try to do nothing but research and put something on the page. At some point during this day, I will decide I hate whatever idea I have been considering, and believe I have nothing novel to say, ever. It’s the same feeling I have had writing virtually every essay or term paper, ever. This means I am used to it and don’t listen (much).
These efforts inevitably bleed into Thursday, by which time I am beginning to feel the heat. Thursday also seems to be a day in which meetings and other bits and pieces cluster — work on the website, podcast planning — so I usually don’t get as much done as I’d like to. I dream of getting Sunday’s piece done on Thursday.
Friday is a day of wrapping-up, but mostly out of habit. RFS will go out in the morning, and I will spend a good chunk of the day sharing it, facilitating connections that arise through the newsletter, and responding to readers. I will also work on Sunday’s piece, which is hopefully at least half done by now. In the evening, I relax with my girlfriend. This is my favorite night of the week.
Saturday I am a bundle of nerves. I wake early, walk to get a coffee and an almond croissant, which is my way of coaxing myself to perform. Then I lock myself in my little study and batter a path to the end. It is usually about 7 pm by the time I finish. At this point, I typically feel good but wary. The bottom could still fall out, and whatever draft I have is hazy and illustration-less.
Sunday, I wake at 5 am, or a little after, and go straight to the study, which is now a bunker. I exit to get more coffee, eat peanut butter on toast, or pace. Around 11 am, I will feel as if the piece is ready and the illustrations are good, and then I will spend another hour on it, somehow. Then I send. Sunday afternoon, I relax, or try to, as I’m usually in a muddy headspace. Namely, over-caffeinated, and very anxious as to what reception the piece will get. Perhaps I should be somewhat more stoic, but I really want readers to receive value and enjoyment from reading.
Then, it all begins again.
Now, if The S-1 Club is in full swing, even this rough outline of a week goes out the window. Chaos, lots of Pomodoro timers, and lo-fi music.
What tools do you use for work on a weekly basis?
I write fiction in the Ulysses Mac App. It feels like a more peaceful, disconnected environment to do that kind of thinking.
I write in Google Docs before pasting over to ConvertKit. Any graphics I make in Canva, though I recently got an iPad so that I might do more drawing. Procreate has been really fun to experiment with. If I need to spin up a website for a new project, I’ll always begin with Carrd. It’s the quickest way of shipping something.
What's a problem that's specific to your line of work that you want a better solution for?
A Creator CRM. In Audience and Wealth, Part II, I described the opportunity as follows.
I can imagine a platform that aggregates interactions across platforms (pulling data from ConvertKit, Substack, Twitter, Stream, Linkedin, Medium, and Telegram) and extracts actionable insights. Which readers respond every week with a thoughtful comment? Which riddler has gotten the right answer five weeks in a row? Who is the IPO-aficionado that's attended every S-1 Club event?
For these scenarios and many others, I would love to recognize and reward the individuals in question. That might take the form of sharing extra content I think they'd like, organizing a private event, helping them with a writing project, or gifting a badge or award visible within the community, a sign of appreciation.
Again, this is an opportunity. While existing platforms track audience members as paying or non-paying entities, there's no system (that I've found, at least) that classifies members based on effort and engagement. That could prove a valuable tool that recalibrates the creator-audience relationship.
I hope someone builds this.
How did you learn to get good at writing?
The greatest aid is, of course, Time. Practice. I spent the better part of a decade writing every morning before beginning The Generalist.
That, and observation, both of the world and the craft of others. Active reading, paying attention to how an author manages to pull off whatever magic trick they’re attempting, is a skill I am increasingly trying to build.
Structured learning is a great way to begin, I think. Whether that be a class at Catapult, or a local college.
What sources of information do you consistently get inspiration or valuable ideas from?
Most of my ideas seem to originate by happenstance, which is to say that I’ll be having a coffee or taking a walk, and some sliver of something will come to mind — a person, a phrase, a question. Usually, those emissions are the product of something I read about a long time ago and found intriguing, or some theme I’ve been mining, consciously or not. All of us have these things, I think; essentially conversations your mind has with itself while you’re not paying attention.
It’s not always like this. Sometimes I go looking for ideas. Usually, I’m not trying to pin down a precise topic, so much as I’m searching for something that surprises me. Then, I file it away and let it percolate. Often, I’ll do this by fumbling through research papers, particularly from journals concerned with the morality of technology. I’m not sure why, exactly that does it for me, but something about that collision makes me excited to think.
For example, here’s one I’ve been thinking about for a while: is it ever ethical for robots to lie to humans? I don’t know what I’d like to say about this paper, but I know there’s something there.
Finally, I’d say that the most reliable source of inspiration beyond this passive processing is fiction. I usually feel a bit let down when a friend or colleague reveals they don’t see the value of literature. While a novel might have a rather less explicit ROI than a book on habit-formation or self-improvement, that’s a reflection of the difficulty in measurement, not of lesser value. Many of the greatest minds of all time — Tolstoy, Orwell, Woolf, Kafka, Baldwin, Achebe, Eliot, Proust — spent years observing and articulating the intricacies of human experience, cognition, emotion then pressed it onto the page.
I think we often confuse the accumulation of information with wisdom. Any good ideas I have usually come from the feeling that somehow I have found an uncommon understanding of something, earned a little wisdom.
What are some mental models or frameworks that you often turn to when confronted with a challenging problem?
Hell yes, or no.
Often ambiguity or equivocation are answers in and of themselves. If you’re not incredibly enthusiastic (hell yes) about a new project, a new job, or writing about a specific topic, then you have your answer (no).
Following the Path
How does your profession impact your worldview?
There are many similarities between the early-stage investor and the “internet writer.” Both seek to interpret the future to their benefit — the first to place an investment, the second to grow an audience.
The primary difference between investor and writer, in my view, is that it is more important for the writer to be interesting than correct. The reverse corollary holds — an investor that makes unimaginative but lucrative bets is a rainmaker; a writer that articulates those stale (if valid) calls is a dullard.
I think my job is to say something new, or something old in a new way. I am, of course, concerned with the veracity of the sources that gird any arguments I make, but when prognosticating, I don’t have to worry that a certain prediction might fail. Instead, I have to worry about whether it was worth articulating in the first place.
This makes every day especially fun. When reading a news story, or observing a piece of new technology out in the wild, I get to wonder what if? without immediately tabulating the impediments.
What advice would you give to someone who thinks they might want your job?
Start writing. Set a cadence: weekly, monthly, quarterly. Share it with a few folks. Increase the cadence. Increase the number of people you share it with.
By increasing the cadence, you shorten the feedback cycle and accelerate your learning.
By increasing the sharing, you strengthen your courage, increase the volume of feedback, and add accountability.
Then, the magic begins to happen.
Who are three people in your field whose work you admire, and why?
The podcaster I most admire is Sam Harris.
If I can slip between these categories, finding my own path (while achieving a fraction of the success of some of these names), I would consider myself very lucky.
What are three books that have made you better at your job?
I don’t think I’ve read a book that made me a better newsletter writer, specifically. But the books that have made me a better writer writ-large are:
Invisible Cities – every sentence can be the key to a dream, a thought, a different world.
Autobiography of Red – it is possible to play with form while retaining emotional sincerity.
Lolita – I don’t know what to say about Lolita, except that it’s the best writing I’ve ever read and illustrates the heights that can be, theoretically, achieved.
Whether you’ve got a newsletter of your own, or just want to improve as a writer, here are five insights you can take from Mario to make progress in your own career.
Starting your day with an act of discipline can set the tone for the rest of the day.
Spend as much time promoting your work as you spent creating it.
Writing has high switching costs. It takes time to get into the flow.
If you’re not incredibly enthusiastic (hell yes) about starting a new project, a new job, or writing about a specific topic, then you have your answer (no).
By increasing the cadence of your publishing, you can shorten your feedback cycle and accelerate your learning.
A big thanks to Mario Gabriele for sharing his insight.
Thanks for reading! If you found this issue of the newsletter valuable, I'd really appreciate it if you could forward it to a friend, family member, or colleague who you think might enjoy it.
Or, if you'd like to share it on one of your social networks, that would be great as well.