Going Pro: A Recap of 2021.
I'm excited and terrified and I'll tell you why.
2021 is a wrap. I don’t know about you, but I’m ready for a new year. I spent the past couple of weeks in Germany with my family. Long walks, conversations, sauna, and journaling helped me clear my head and leave this year behind. I also spent time hunched over my laptop in a dinky airbnb room that doubled as my wework. Back from my foggy and grey-skied hometown, I feel both excited and terrified. Let me explain.
I sent my first substack email in August 2020 and “went pro” (started the premium tier) in May 2021. I’ve since sent 55 emails (and 87 in total). Frankly, I cringe more than a bit looking at much of my early writing. I suppose that’s a good thing, a sign of learning and growth. The implication is (hopefully?) that in a year I will smirk and shake my head at much of what I’m writing now.
Total (free) subscribers stand at 6,689. A big thank you to Tegus for being the first sponsor of my free emails.🙏
I have 392 paid subscribers for annualized revenue of ~$45,700.
I’ve pondered whether to put these graphs online. They trigger a lot of feelings: happiness and gratitude. But also anxiety and envy.
I feel very grateful to all of you (and doubly so to my amazing founding members). I am happy that, for the first time in my life, I am following a path of deep resonance. Learning and sharing ideas and stories through writing truly feels like my mission.
But I also worry that it’s just not enough. That I haven’t found enough “creator-market fit” and that I’m in denial about it. It’s not yet a sustainable income. And I know a bunch of writers, analysts, and creators who achieved more growth (and reached comfortable if not highly attractive incomes) over the same time period. Not surprisingly, this tendency to look at my life in relative terms is one of my least favorite habits.
“Envy is a really stupid sin because it’s the only one you could never possibly have any fun at. There’s a lot of pain and no fun. Why would you want to get on that trolley?” Charlie Munger
How very true. It’s painful and poisons the feelings of gratitude and appreciation. Even so, right now it’s a feeling that’s present.
Something that became very clear to me over the past few weeks is that I share things in writing that I still find uncomfortable to discuss in person. Writing helps me take an honest look at myself, warts and all. Sharing with the world feels like an act of acceptance: “This too is true. I don’t like it. I hope I can change it. But right now it is true and I accept myself with this flaw.”
I’ve found that trying to hide or deny what I don’t like about myself doesn’t make it go away. It just leaves me feeling ashamed and the undesirable feeling bottled up, lying in wait. I feel some pride when writing about these moments of weakness, like my post-divorce mental doom-loop, because it feels honest, timeless, and may help me and my readers avoid repeating the same mistakes.
This then is one of the few things I can truly promise a reader. That I will not shy away from looking at an uncomfortable truth, to the best of my ability.
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“All successful newsletters are alike, but every unsuccessful one is unsuccessful in its own way.” Leo Tolstoy, probably, if he was a substack writer
I’ve been asked multiple times about advice on writing a newsletter. I’m going to offer a few observations with the caveats that I haven’t applied most of them and that I wouldn’t call my own substack successful until I can make a living with it.
Start by studying people who successfully and recently (that is, in a similar competitive environment) built theirs. Some examples that I enjoy reading: The Generalist, MBI Deep Dives, Bear Cave, Liberty’s Highlights, Fabricated Knowledge, Doomberg, TSOH, Net Interest, Investment Talk, The Diff, and, to a lesser extent since it’s long-established, Stratechery. They’ve all found fit between the author’s skills and interests, an audience with the willingness to pay, and at least one distribution channel (mostly Twitter). While there’s something to learn from all of them, the challenge is to find your own unique combination.
Some patterns I’ve noticed:
Clear value proposition: Tell your audience concisely what you’re doing, why it’s interesting and relevant, and what they can expect if they pay you.
Growth is unpredictable: I still have no good handle on whether a particular piece will do well. As a rule of thumb, the more flow I found when writing (the less it felt like work), the better. Name recognition also helps (not a coincidence that a piece about Buffett did best). But much depends on whether others share your work which leads to step-function growth.
Consistency and frequency are good, all else equal. All else is of course not equal. Publishing on a consistent schedule, same day and time every week, seems to work. Writing shorter and more frequent pieces offers you more shots on goal. But I struggled with both.
Some markets are better than others. If you have a choice, perhaps go for a new or unique angle on a large market with an abundance mindset (such as tech and crypto readers happy and flush with cash; or former zerohedge readers with a sense of humor). Or pick a deep, emotional market (politics and culture seem to have some of the biggest overall substacks). Or cover a niche in which a smaller audience is willing and able to pay up for your insights (like markets and exchanges). However, I’m not sure you can choose what you’re interested in. And if you’re not passionate about the subject, someone else will do a better job.
Timing matters. Early 2020, when much of the world was in lockdown, was a great time for online content. The summer of 2021 was dead by comparison. Keep this in mind when benchmarking your own growth.
Don’t forget to market. My newsletter stalled when I neglected my ‘growth engine’ (Twitter threads) in favor of researching and writing more. Unless your product is so valuable that the right people will inevitably hear about it (looking at you, Mike), you have to keep competing for attention until your email list is at scale. I will have to do a lot better at this kind of parallel processing in 2022.
Ultimately, you want to figure out what you’re uniquely good at, what feels like play to you (Naval), and use your combination of interests and skills to “make something people want” (Paul Graham). Then you just have to keep at it and tell everyone about it.
To date, my writing revolved around two threads: learning from great investors and operators as well as my own journey. Sometimes they intersect, such as when I find someone like William Green. It’s all part of the same newsletter which makes it harder to define the value proposition and find the natural audience. Sometimes it feels like I want to have my cake and eat it too: write about what I want, how I want, when I want, and yet make enough money to live in an expensive city (where my friends are and where I’ve found the complicated and unavailable women that I tend to fall for…).
I know that I’m a bit stubborn about this. Because of the element of self expression, I haven’t treated the newsletter like a job or a business. I have not implemented much of the advice I would give another writer. Interestingly, the personal pieces often found the most readers and resonance. But they’re also all outside the paywall.
Still, I don’t see why learning about investing and the inner game would not be relevant to an audience ten times as large. But I might be biased. As it stands, much work remains to make this self-sustaining. I’m excited for more deep dives, more conversations and Q&As, and generally a year full of learning, exploration, and the continued journey to more self-awareness.
Right now, I can’t see further ahead than a few months. Much like a walk near the foggy Neckar river this past week, the path reveals itself with every step. My task is to keep moving and trust that I’m going in the right direction.
A special thank you
A final shoutout to the people whose advice, ideas, support, feedback, and friendship enriched my life this year. Thank you also to everyone who commented or emailed after reading one of my pieces. You make it all worthwhile. And thank you to everyone I forgot (don’t be mad, please)!
In no particular order: Alix Pasquet, Jim O’Shaughnessy, Dan McMurtrie, Tom Morgan, Liberty, Andrew Walker, Jonathan Tepper, Levon, Tilman Versch, Mike, Tren Griffin, Linda, Kevin G, William Green, Eric Shahinian, Lyle McKeany, Matt Reustle, Michael Mauboussin, Modest Proposal, Brandon Beylo, Josh Wolfe, Gavin Baker, Lawrence Hamtil, Andrew Rosenblum, Alex Danco, Bill Brewster, Marc Rubinstein, Liz, Michael Batnick, Edwin Dorsey, Peter Morken, Ti, Post Market, Hide Not Slide, ShitFund, Ramneek, and the team and community at Foster.
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