One Hundred Thousand

Friends,

The Generalist has reached 100,000 subscribers. That’s not a sentence I expected to write. Had you asked me in 2020, I would have told you the only place those words would be penned would be in Mario’s Secret Little Book of Big Dreams.

Benchmarks are always arbitrary, but this one feels more meaningful than most. One hundred thousand. Six figures. Roughly double the capacity of New York City’s Yankee Stadium. The population of a moderate Midwestern town – Dearborn, Michigan, for example, or Wisconsin’s Green Bay. It is a number that feels real, and that makes The Generalist feel more real, too. Sturdier and stronger, less like a side hobby and more like the emergent media business it is.

There is only one response to a moment like this: immense gratitude. Thank you. Thank you to friends old and new, to long-time readers and first-time subscribers, to the one hundred thousand (and twenty-eight!) of you who have decided to receive our writing every week. Building The Generalist is a joy, a gift, and a privilege I do not take lightly. It remains mesmerizing to me that I get to write about the most interesting technologies and businesses on earth – as a job! And that doing so allows me to connect with so many of you. I have learned so much from you over the past three years, and I hope I have managed to offer the same.

As well as making me even more excited about the road ahead, this moment encouraged me to contemplate how we’ve gotten here. What worked? What failed? What mistakes have I made, and what have I learned? How does this sum of experience influence where The Generalist is heading next? In today’s piece, I reflect on the road to 100,000, sharing the advice I wished I’d known when I was starting out. My hope is that these lessons illustrate our journey, invite you to understand how we think of building this publication, and provide useful guidance for writers and company-builders who are just beginning.

P.S. – Something big is coming. Next week, we’re taking the wraps off of The Generalist’s biggest upgrade since we first started. It’s an evolution we’ve been thinking about for more than a year and actively working on for many months. I think you’ll really like it, and I can’t wait to share more.

Against permanence

“The more a thing tends to be permanent, the more it tends to be lifeless,” the philosopher Alan Watts intoned. Though Watts usually directed his formidable wisdom towards existential matters, his observation applies to the narrower corporate world. A company that does not change, dies. Allow it to stay still for too long, and its blood will run cold. Staving off extinction and the pre-death of “permanence” requires continual work and, more importantly, continual risk. You must venture again. You must try something new. You must scrap something that works well in favor of something that may, possibly, work better. You must do this while trying to hold fast to focus.

The “exploration-exploitation” framework has been a helpful way of understanding these competing drives. This dilemma, found across industries, articulates the tension between applying the optimal known strategy (exploitation) and searching for a better unknown one (exploration). Increasingly, I’ve come to think of The Generalist’s journey in phases defined by one or the other. In the early days, we operated in exploration mode. We tried different types of pieces, various distribution methods, and even different mediums. In The Generalist’s inaugural pitch deck, which long-time readers may remember me sharing publicly, I outlined the vision to run six concurrent newsletters and, for a time, we did.

This period of trial and error taught me a great deal. I discovered that The Generalist really shone when tackling case studies of private market companies. There were relatively few publications that did this kind of evergreen analysis backed by deep research, and we were one of them. This focus appealed to a senior audience of tech and investing professionals, whom I felt excited to write for and be in conversation with. All of these aspects now feel core to The Generalist’s identity, but they were not a given.

Over the next two years, The Generalist entered “exploitation mode.” We wrote a lot of case studies. We got better at writing them, and we got better at sharing them, and our audience grew. That’s not to say that we didn’t experiment during this time. We changed our business model, revamped our reading experience, and analyzed companies from disparate sectors. But this core, this central scaffolding, remained stable. We strengthened it week after week, month after month.

Toward the end of 2022, Ali and I started thinking about pushing The Generalist back into an exploratory phase. We didn’t think of it that way at the time or use that language, but in hindsight, it’s what we were doing. We recognized the publication was doing well, but reaching the next level would require us to rethink our fundamental assumptions and build new muscles.

Throughout this year, readers saw the results of these conversations. We moved back to Substack after dedicating real resources to building our own site. We also meaningfully increased our content variety. Though we still regularly publish case studies, we’ve expanded the types of businesses we profile (see: A24) and introduced or expanded new series. The What to Watch and Modern Meditations mini-franchises have resonated with the audience and expanded it. Both feel very much in line with The Generalist’s DNA but also add something fresh to it. In the months to come, we plan to try more of these experiments.

Next week, we’ll unveil the most significant evolution of The Generalist since it started. I can’t wait to share more. Suffice to say that optimizing its impact will require us to embrace this age of experimentation and allow for the vibrancy, the life, of impermanence.

Popularity versus influence

Popularity and influence seem like siblings. Indeed, they’re often confused with each other. We call the Instagrammer or Twitterer with a few million followers an “influencer” rather than simply a celebrity, on the premise that they are capable of nudging your actions one way or another. A few outstanding figures may succeed in this measure, but for the most part, those with large followings don’t tend to move the world. It’s not often an Instagram Story stays with you or a Tweet thread reframes your perspective. This is, by design, fast, ephemeral content. On the scale of true influence, the impact of this work is often relatively minor – the battle for hearts and minds occurs elsewhere.

Useful questions to ask yourself as a novice writer: would you rather attract a small, targeted audience or a larger, broader one? Would you like to speak to a few who care about your subject deeply or many who consider it only moderately interesting? In short, if forced to choose, would you prefer your work to be influential or popular?

This is not a rhetorical question. It is a viable strategy to try and broaden your audience as aggressively as possible. In many cases, it’s the default strategy; more usually feels better. When you see numbers tick upwards, when the graph slopes alluringly, you have a sense that all is going right, ticking along, building momentum.

Equally, it is legitimate to go in the opposite direction – to niche down and focus on overserving a smaller audience. That will mean the numbers will not tick up so quickly, and the line will draw a sleepier trajectory, but by less quantifiable measures – by the measures that matter to you – you can succeed greatly.

Though The Generalist has focused on a niche group since the beginning, I think we’ve grown more comfortable and confident in this approach as the years have passed. I no longer think about aggressively expanding the audience but instead focus on how we can more deeply serve the incredible group we’ve assembled. While I believe there are still many more people within our target audience who have yet to discover The Generalist’s work, I also recognize that there are probably not millions of people keen to read 10,000-word analyses on semiconductor companies or fintech giants. Those who do want to read this kind of work – like you, reader – are exactly the people I’m excited to have conversations with every week.  

Tech as a lens, not a category

The Generalist writes about technology. But what does that really mean? As “tech” has succeeded in insinuating itself into every business and aspect of our lives, creating demarcations has become more difficult. Is Netflix a tech company or a media business? Is Flexport a logistics firm or software company?

As these lines blur, The Generalist has increasingly decided to view “tech” as a lens rather than a category. That’s another way of saying we’re interested in innovation – albeit the modern strain popularized by tech giants. We’ve stumbled into some of our most popular pieces by looking for companies applying a “tech” playbook to less obvious sectors: A24 demonstrated how social media acquisition could fundamentally alter film distribution; Starbucks used its habit-forming product to create a secret neobank; Red Bull devised an asset-light beverage brand with the help of viral marketing; and F.C. Barcelona dabbled with crypto as part of its plan to reverse financial decline. Applying these lessons in a new context not only makes the playbooks themselves easier to grasp but also reveals something new about organizations we may think we understand. Readers seem to particularly enjoy the opportunity to learn about these businesses, tracking how tech is influencing familiar brands and franchises.

Giving ourselves permission to tackle these theoretically off-piste topics has been incredibly fun, valuable, and fulfilling.

Efficiency myths

You know this story: Picasso, sitting in a cafe, sketches on a napkin. An admiring patron spots the famous artist and asks to purchase his doodle. Picasso names a price of 1 million francs, to which the patron expresses her astonishment, arguing that something that took five minutes to make shouldn’t cost so much. Picasso replies, “My dear, it took a lifetime.”

One lesson you might take from this (probably apocryphal) anecdote is that practice breeds efficiency. The better you become at a given task, the more quickly you can create something of value. Eventually, you might – if touched by genius – arrive at a Picasso-level of mastery, churning out million franc vignettes over a frothy cappuccino. Perhaps this dynamic holds in the business of serviette scribbles, but I have found it much less so in the rather humbler world of newsletter writing.

If you had asked me when starting The Generalist if I thought it would take me less time to write a case study each week, I would have found it a silly question. Of course it would! The more case studies I wrote, the more efficient a case-study machine I would become. I could not become infinitely quick, naturally, but I could expect to see significant improvements in my research, analysis, and writing, which would translate into a faster process.

What I did not account for was how my expectations would scale alongside my experience. As I got better at writing weekly pieces, I began to demand more of myself. I did not want to write as good a piece as I had written the week or month before but a considerably better one. In the quest to do that, I expanded the scope of my work. I found new research sources. I started interviewing people. I pushed myself to write in fresh, interesting ways and to incorporate greater depth. I asked myself, with greater stringency, to come up with more original ideas and sharper analysis.

The result is that it now takes me much more time to write a case study than it used to, not less. When I was just starting out, I would pick a company to write about and then sprint for a week until publication day. I conducted research as thoroughly as I could, but it was not exhaustive. Now, it can take weeks or sometimes months to put together a case study. I’m often interviewing more than a dozen people, reviewing considerable collateral, and sifting through a much broader range of sources. While the final product is undoubtedly better, I no longer expect efficiency gains and welcome the opposite.

Substack and loss-aversion

The single best decision The Generalist made this year was returning to Substack. The sharp uptick you see in the graph above is a direct result of returning to the platform and benefitting from the network it has built. Though we saw our steepest growth in the wake of our immediate return, the months since have affirmed our choice and made me wonder why we left in the first place.

I know the “real” reasons, of course. We wanted to create a more customized brand. We wanted to control the user experience. We didn’t want to give up 10% of our revenue. All of these are true, but are they the true base-layer rationale?

The more I’ve considered the matter, the more I attribute our choice to leave Substack as an example of loss aversion. The notion of “losing” 10% of subscription revenue felt more painful than the pleasure of the potential gains we might have logged by staying aboard. I overstated the importance of holding onto as close to 100% of our subscription revenue and underweighted the incremental value Substack could deliver. (I also fundamentally misunderstood their network ambitions.) Today, I never think about what we “lose” by being on Substack, only the extraordinary amount we gain.

Quiet quitting Twitter

Simple advice for my former self: spend as little time as possible on Twitter. Although the platform was helpful in building distribution in The Generalist’s early days and a valuable source of serendipity, I increasingly find it an empty, aggravating pursuit.

In last year’s annual review, I shared my plan to spend much less time on social media; ten months of mostly abstaining has proven an unadulterated positive. Though I’ll still share Generalist articles via my account and occasionally post something else, I no longer visit the site to browse or interact. On a weekly basis, I’ve cut down my time on site from several hours to less than an hour. Most weeks, time on site could be measured in seconds.

It’s always difficult to measure the absence of something. How many annoyances have I avoided by staying off social media? How much posturing have I side-stepped? How much snark? I can’t quantify these things, but I have noticed improved focus and emotional equanimity.

I no longer find myself typing in “tw” by default when I open my browser, or hungering to check my notifications. While writing a piece, I don’t duck out for a brief dopamine boost, which can quickly turn into a prolonged dopamine wallow. Walking in a park with sighing trees and a squirrel scrabbling amongst the branches, I don’t find myself returning to some snippy remark from a random account. In subtle ways, I think I’ve managed to rewire my brain for the better.

At a foundational level, staying off Twitter has taught me something about how I see the world and generate original ideas. At various points in the last crypto cycle and the current AI boom, Twitter has served as the place to watch the revolution unfold. It has hosted remarkable new demos, conversations, and breakthroughs in close to real time. What I’ve realized is that I am not particularly good or very interested in following progress at this altitude. I’m not skilled enough to quickly assess which revelations are real and which aren’t, which is about to remake an industry, and which is little more than a mirage. To be clear, I think some people genuinely are good at this. But there are others of us who come up with our best thoughts after reflection, by looking at the past, by trying to trace the shape of things. For that group, being “plugged in” offers less value – you invite much greater noise and little signal.

If this resonates with you and you’re considering a similar step, I strongly recommend it. Though Twitter and other social media platforms have their uses, fundamentally, they are tools that want to be our masters. They will take as much time as they can from you and leave you somehow miserable yet ravenous for more. If you can’t avoid these platforms completely, I’d suggest trying out a tool like News Feed Eradicator, which strips out a major source of noise.

Extracting weird surpluses

So much of the world’s most valuable knowledge is held in the heads of people who will, at some point, die. In doing so, much of this information dies with them, unexpressed.

I’ve come to think of this wisdom as a strange sort of surplus – valuable excess intelligence waiting to be extracted. Often, it doesn’t require much work to bring to light. If you were able to have a pointed 15-minute conversation with Geoffrey Hinton, Patrick Collison, Jensen Huang, or Mary Meeker, it’s likely that you could learn something profoundly valuable – or at least interesting – with the right questions. With relatively little effort on their part, they could impart some of the superabundance of knowledge they’ve accumulated.

Some of our most valuable concepts have come from thinking about The Generalist’s work through this lens. How can we allow the world to capitalize on these surpluses? Series like The Wisdom List and Modern Meditations are explicit attempts to do this, as were earlier projects like The S-1 Club and RFS 100. The Wisdom List asks founders to share their hard-earned lessons, Modern Meditations encourages tech luminaries to divulge net-new thoughts, The S-1 Club asked sectoral experts and investors to weigh in on upcoming IPOs, and RFS 100 curated startup ideas from founders, operators, and VCs. All were designed to surface latent value.

As you might expect, accessing these surpluses has become easier as we’ve grown.

Increasingly, some of the world’s best investors, founders, and operators are willing to sit down and share their knowledge with this audience. In the coming months, you’ll see us continue experimenting with this concept and finding more ways to bring these weird surpluses into the light.

The “flip-switch” theory of burnout

I have a theory. There are two types of professionals: “dimmer switches” and “flip switches.” Dimmer switch professionals have the gift of gradation. They are capable of adjusting their effort, turning the dial up or down to meet the task at hand or accommodate their abilities on a given day. Flip-switch professionals do not operate by degree; they are either off or on. When off, they are more or less useless – at least by their standard. But when they are on, they beam with hard, bright light.

Running The Generalist has taught me many things about myself, including that I am a flip-switch person. Either the switch is off, and I am mostly coasting, or it is on, and I am burning with obscene, inefficient effort. Reflecting on my previous jobs, I realize I was off most of the time. Occasionally, I might flip the switch to get something across the line or because I found some project particularly interesting. But for the most part, I allowed the better part of my mind to sit in vacant, unobtrusive darkness.

The entirety of building The Generalist has been done amidst wild phosphorescence. I am grateful for this. I do not think I could have made this a viable business if I wasn’t willing to work seven days a week for several years, nor would I have improved as quickly as an analyst if I hadn’t committed to shipping 5,000 to 10,000 words nearly every week.

But earlier this year, the bulb went out. I had felt tired for the better part of eighteen months, but this was the first time it felt actively painful to sit in front of my computer and write. Writing is rarely easy, but when it's hard, it's hard in the way that running or solving a difficult puzzle is hard. There is strain and effort but also a sense of something valuable being worked. This felt different: a stubbed toe, a sliver of wood under a fingernail, lemon juice squeezed onto the frontal lobe. A varietal of unpleasantness with no bloom and no fruit.

Can you write when you feel this way? As it turns out, yes. I pushed through this feeling for several months. Though I enjoyed myself less, I could still deliver equally strong pieces.

The last quarter has been about climbing out of this sensation. First, I took a long break. For nearly three weeks, I shut my computer and read and walked around New York and puttered around on fiction projects and went to a movie on a Wednesday afternoon. For the first time since I started The Generalist, I felt a separation between myself and the company.

Second, we began to make changes to the volume and cadence of my output. We switched our publication date to Thursday – a shift I hoped might allow me to take weekends off. It has mostly worked. I also began to vary the types of pieces I write, including some that require less, or at least, different effort.

In short, I am rewiring myself to become – at least conditionally – a dimmer switch. I would like to learn the ability to modulate my effort and manage my energy more cleverly. To be clear, I do not want to lose my flip-switch capabilities; there are times when anything less than maximum energy is insufficient. But it is increasingly important that I find another way to operate. I should have started sooner.

Flavors of wrongness

It is painful to be wrong. It is excruciating to be wrong publicly, on the record, in front of thousands. But if you are to write about the future, regularly, you must make wrongness your friend.

How do you do that? It helps to distinguish between the different flavors of wrongness. Not all are equal. There is the Goddamnit You Brainless Dolt kind of wrong. There is the You Can Do Better type, too. A writer who reflects back on their catalog will find a collection of others: the HmmHmm I’m a Little Off But Not By Much varietal, the Ok I Was Mistaken But My Idea is Still Interesting specimen, and its cousin, the I’m Wrong…For Now breed. There are good ways to be wrong and bad ways to be wrong, intriguing ones and stupid ones, boneheaded blunders, and unavoidable errors.

As an overambitious, grade-addled student, I viewed wrongness more or less like the body receives pain – a sign to move, flee, or change tact. When you are wrong in school, it is usually swiftly and definitively delivered. There is little shading. Writing about technology’s frontier is not like that. Most of what you are doing is peering over the horizon, where the shapes begin to get fuzzy. You say what you see. It may take a long time for your views to be validated or disproven, and at various points in that journey, you will look foolish or brilliant. To make peace with this, without letting yourself off the hook, is at the heart of this work in a way I hadn’t expected.