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August 29, 2021

The Generalist Turns 1

Reviewing The Generalist's first 12 months.

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Last week, The Generalist turned 1.

As with many strokes of good fortune, it feels both as if it has been much longer and much shorter — like I might have started on a whim this afternoon, otherwise, a decade ago. Regardless of Time’s weight, in both cases, there is a familiar feeling that The Generalist is — I hope — just beginning. 

This has, without exaggeration, been the best 12 months of my life. I’m really not sure what I’ve done to deserve it. That’s been true both personally and professionally, in ways big and small. Some highlights:  

  • The Generalist surpassed 40,000 readers
  • Revenue outstrips my wildest goal for the year and the business is sustainable
  • I get to write every day and can feel myself getting better
  • I’ve gotten to deeply study some of the most fascinating companies and trends in the world
  • I’ve met and collaborated with people I respect and admire
  • Our community is full of some of the smartest, most thoughtful people I’ve ever met and that I want to be friends with IRL

I think I have had an extremely lucky start to life as an entrepreneur and public writer, but it has not been without incidence or adversity. I have worked harder on The Generalist than any other professional project. Growth has alternated between ahhhhh, sweet dopamine! to why, newsletter gods, why? A befuddled hedge fund threatened to sue me. 

But even those moments have brought a kind of joy; of putting one’s full effort forward, working on a worthwhile problem, pushing past friction. And, above all, of trying to build something bigger than one’s self. 

That is what gives me the greatest excitement when I think about The Generalist today. It has become much more than the brainchild of a single person, and my hope is that this will become increasingly the case in the years ahead. 

This piece is, in many respects, a (re)articulation of our shared vision and a reflection on what has brought us to this point. I’ll highlight both the good and bad of the last year, triumphs and failures. In particular, we’ll discuss:

  • Prologue. What came before The Generalist. 
  • Growing. Slot machines and structural hacks. 
  • Business model. Tentative moves and protecting trust. 
  • Writing process. How I write solo pieces and manage multiplayer. 
  • Community. Scaling belief. 
  • Future. What does the next year hold? 

Let’s begin. 

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Prologue: How we got here

I’ve always found the trickiest part of a piece to write is the first sentence. Where should the story begin? The author has not only to commit to a time, a chronology, but an altitude. How high up should the reader be to see the shape you're drawing? How much detail should you show?

I feel the same tension here. What I really want to ask is: what do you want to know? Where do you want to start? 

I've chosen to begin where I might if someone close to me were to ask, “Why did you start The Generalist? What made you want to do that?” Forgive the biographizing such an origin entails. 

The truth is that I have always loved writing. I think everyone has a passion like this — something that you not only enjoy but confirms your sense of self. Sometimes we need time to find it but I am lucky to have discovered that activity early. Because I did, a not insignificant part of my childhood and adolescence was spent scrawling away at something. That continued through college, and beyond. One of the first things I did after leaving undergrad was register for night school classes in fiction writing, which led to joining a workshop.

Therein began a habit: for the next seven years, I would get up an hour early and go to a coffee shop to work on my novel, before beginning the day’s activities. I did that while failing at a lobotomizing law firm, moonlighting as a line cook, making time as a graduate student, and finally, building a career in tech.

This is still how I start most mornings: sitting at my computer, trying to move the novel forward, one sentence at a time. One day, I hope the book I have been writing since 2012 — it’s a near-future Künstlerroman set in Kathmandu, thank you for asking — feels finished, and worthy of soliciting a publisher. But even if that were to never happen, the book gave me a great gift; it was a project compelling enough to provoke practice. 

It made a difference. I reached a sufficient level to attain entrance to a few well-respected MFA fiction programs, and even though I did not attend, that gave me the confidence that I was not a total charlatan. Perhaps more importantly, writing became something I did, without much thinking. I got used to writing well on some days, badly on others, and bringing whatever I had cooked up to the workshop to accept critique. 

It was during my stint as a venture capitalist that I got up the courage to start sharing my work in public. By that point, I had developed a fascination with the tech sector that I’d exercised in different forms: “founding” a payments startup during my Master’s program, working at an incubator in Bogotá, running a sketchy ghost kitchen. 

An old boss of mine, Leif Abraham, encouraged me to use my passion for the written word to talk about tech. If I liked writing so much, why didn’t I write about the sector in which I was spending my days? When I didn’t pay much attention, he brought it up again a few months later, and again after that. Others encouraged me, too. 

In August of 2019, I decided to give it a shot. On a flight to San Francisco, I wrote the first draft of the first Generalist article. A few days later, I published 30 Minutes or Less: The Manufactured Urgency of YC Demo Day on Substack. 

The piece didn’t go viral or prompt a backlash. It was not hotly discussed nor worthy of much mention. But small things did happen: a few messages of appreciation, a question, a trickle of subscribers. Even tiny numbers seemed crazy, meaningful to me. Ten people had signed up? Ten people wanted to read what I had to say? 

In writing that first post, I had no intention to commit to a regular cadence. The Generalist would be akin to a Medium blog — somewhere to post musings when I got the chance. But I had so much fun that I didn’t want to stop. What if I wrote every day?.

I tried for exactly two days — but I am not Fred Wilson. I settled for a weekly cadence.

Now, as you may have noticed, that first salvo occurred two years ago. But for the twelve months that followed, The Generalist was a side-project, a hobby that bears only a passing resemblance to its current form. For one thing, the product was called “The Brunch Briefing" and was just a round-up of different links. I would sometimes write a longer introduction, and always tried to add a little razzle-dazzle, some strangeness, to the curation, but it had a weaker center of gravity.

Last summer I began to think of going full-time. It is a decision that makes very little sense, except in hindsight. The Generalist had earned $0 in revenue. It had attracted about 1,500 subscribers. It was, as I said, mostly a collection of links. 

But I couldn’t ignore how much fun I was having. 

At night, when I was trying to fall asleep, ideas for new stories, or formats filled my head. I experimented with many: trying out interviews, S-1 breakdowns, and Twitter digests. I loved hearing from readers and finding others with shared interests around the world. Surely, something worthwhile could be made. And what was the worst-case scenario? I was lucky to be able to go without a salary for a period of time, and I figured someone might still hire me if I flopped. 

On August 16 of last year, I announced my intention to go all-in. By then, The Generalist had reached 5,500 subscribers. As part of a larger presentation, I set out my goals for the next 12 months. I felt a little sheepish outlining such preposterous figures: 

Let’s see how we did. 

Growing: Lawsuits and lotteries

At the time of writing, these are The Generalist’s audience metrics: 

  • 40,606 subscribers
  • 49.93% open rate
  • 9.26% click rate

That represents 2x the subscriber count I set for myself last year, and roughly a 630% growth rate year over year. That’s been managed while keeping open rates largely stable, down from 51.53%. 

So, how did that happen? It’s required a mix of consistency, experimentation, and serendipity. 

Consistency

Whenever someone asks me how I’ve grown The Generalist, I’m always reluctant to share. Not because I have some closely-guarded secret but because my advice is so banal. The best way to build an audience is to create something people want, consistently. If you do that and share your work, you will grow. It really is that simple, and that difficult. It might not be as fast as you’d like, and there are certain techniques that can steepen the slope, but without nailing these basics, you’re fighting an uphill battle. 

Each component matters: 

  • Creating something people want. Not everything needs to be created with an audience in mind. Some of the great works of art could likely not have been constructed had the creator thought too closely about the viewer’s response. But if you seek to make creating your job, this is necessary. That doesn’t mean you have to take an obsequious stance towards the reader, or chase engagement above all else. But you need to find your people. My goal with The Generalist has been to write things that feel true to myself that also provide value and attract interest from others. 
  • Do it consistently. It’s very tempting not to create. Sure, sometimes the spirit moves you so strongly that you can’t help but write. But writing is effortful work, requiring a high cognitive load. (I read once that it’s roughly equivalent to playing elite chess, which I am skeptical of, but very much enjoy believing.) There are so many more pleasurable things you could do in your free time instead — eat peanut butter on toast, watch Love Island, nap. How can we stave off such glorious sloth? A commitment to consistency. Setting a cadence forces practice, improving your work. It also helps readers perceive your writing as a product, and one that can be relied upon.
  • Share your work. It’s hard to know what people want. The best way to figure it out is to share what you’ve created and get feedback. Use that to iterate and improve. Of course, without sharing your work, you also can’t hope to attract an audience. This is tricky to start with — it feels self-promotional because it quite literally is. Bit by bit, it becomes easier. Reframing sharing one’s work as beginning a conversation rather than asking for attention helps, too. 

So, the biggest reason The Generalist has grown is that I write something that some people like, reliably. That has meant that The Generalist’s largest source of growth, by some distance, is direct. Happy readers tell their friends, who tell their friends. 

Similarweb

While I’d love to be more proactive in encouraging explicit referrals, and up my SEO game, I hope that direct traffic will remain The Generalist’s largest traffic source in the years ahead. 

Experimentation

You may have noticed The Generalist has streamlined. Look, for example, at this slide from last year’s launch deck: 

At the time, The Generalist was experimenting with six different newsletters. Why so many? Why not try and nail one first? 

The most truthful answer is that I find it easy to get excited by new ideas and can let that get the best of me. But it also reflected my mindset: I wanted to build a creator business like a software company, testing out different products, and iterating quickly. 

By and large, I think that approach has served me well. Though The Generalist has since slimmed down, each of these products taught me something valuable that informs how I approach the weekly briefing. Interviews like The Miss or The Prologue encouraged me to take a closer look at management teams, treating my analysis like a psychological profile. Organizing S-1 Clubs sparked my thinking around multiplayer media, a key part of The Generalist’s model. 

In trying to find product-market fit, I’ve found it helpful to experiment with the explicit goal of increasing The Generalist’s “value over replacement.” In the age of endless content, more than ever, there’s a need to differentiate your writing from others, ideally in a manner that cannot easily be replicated. 

The Generalist (or The Brunch Briefing in those days) began with a product that had low value over replacement: a link roundup. Yes, I added commentary and curated differently than another creator might. But anyone that found such topics interesting could choose from a multitude of similar properties, many with more established reputations. Why not choose Morning Brew? How about The Hustle or The Download? 

Over time, I honed The Generalist’s value over replacement, finding ways I could separate myself from other creators and publications. I’ve found three primary differentiators: 

  1. Writing style and storytelling. Though there’s plenty of business coverage, a lot of it is perfunctorily written. I strive to create separation by focusing on storytelling and putting great care into the crafting of sentences. Reading The Generalist’s analysis of a company should feel exciting and absorbing. I also often look to frame these narratives in larger historical, philosophical, or psychological contexts. The result is hopefully a piece that feels intellectually rich, is worthy of your attention, and will shape your thinking. 
  2. Depth and thoroughness. We have plenty of places to read fundraising news, but fewer publishers dig deeply into a company or trend, explaining how it operates, from multiple angles. Those that do, often are conducting highly-priced equity research. The Generalist is hopefully of equivalent or better quality than these alternatives at 1/1000th of the price. 
  3. Creating conversation and connection. The writing can be just the beginning, if you let it. As often as possible, I bring kindred spirits into a conversation either through multiplayer pieces, community discussions, or events. That’s not unique, but also not typical. 

I’ve done a poor job capturing data, but triangulating between sign-up spikes, social shares, and anecdotal evidence seems to suggest that the most popular pieces have hit at least two of these dimensions, and often all three: 

  • Stripe: Thinking Like a Civilization. This was one of my most deeply-researched pieces, coming in above 12,000 words. I conducted about ten interviews and reviewed private transcripts to form my opinion. I framed my analysis with a story that, though a little grand, captured part of what makes Stripe special. 
  • Tech in Africa. This was a multiplayer piece and benefitted from the expertise and insights of ten other collaborators including fund managers and founders. Those people brought context on what it’s like to build and invest across the African continent with a rigor I could not have achieved through solitary research. We went deep and sparked a conversation online. 
  • The Mythology of Red Bull. Crazily, this piece was originally paywalled, but it still took off. I’ll share more on that below. It was really the storytelling around how the company harnesses “mythology” and differentiates itself from other beverage brands that captured most attention. 
  • Coupang: The Art of Obsession. This was another multiplayer piece, with seven other collaborators. The team really brought the heat when it came to analysis, especially in dissecting Coupang’s logistical infrastructure. We also hosted an event after publishing. 
  • FTX Trilogy. Though more recent, all three editions of the FTX Trilogy have done well so far. Much of this was due to the unparalleled amount of information I was able to access. Sam Bankman-Fried, FTX’s CEO, shared a well-stocked data room that I used to shed light on the business. By covering it across three pieces, I was also able to give the company the depth and nuance it merited. I’d like to do more series like this one. 

Going forward, these are the pieces I intend to use as models, with the goal of maximizing “value over replacement” along the three stated dimensions. 

(Of course, I’m not alone in trying to manifest compelling, deeply-researched, connective stories. Some of my favorites creators include Packy McCormick of Not Boring and David Rosenthal and Ben Gilbert of Acquired, who are masters of this.)

Ultimately, I could not have landed on these differentiators without experimenting with product lines and content formats. 

Serendipity

The final growth hack is, of course, luck. Not much of a hack. Every once in a while, something you do attracts sufficient attention to spike your growth. 

So, what drove The Generalist’s jumps? 

Going full-time 

As mentioned, last year I announced that I was going all-in on building The Generalist. I shared the news on social with a deck outlining my plans and goals. People responded positively and new readers flooded in.

Compoundergate

In October, I worked with a collaborator to write a piece on “compounders”: companies that grow reliably over time. The use of that word, and phrases like “good to great” angered a partner of Durable Capital, a $6 billion hedge fund. That partner alleged the piece relied on proprietary information (it did not), and threatened to sue my $0 in revenue newsletter. After trying and failing to find an amicable solution, I told the story in The Six Billion Dollar Stare and on Twitter. It led to an outpouring of support from fintwit, as Durable was meme’d into a hasty retreat.  Investing legend Dan Loeb even tweeted his support. (Thank you again to everyone that helped.)

The S-1 Club lists on Product Hunt

In November, we took The S-1 Club to Product Hunt, and managed to rack up more than 1,000 upvotes. We finished as the #4 launch that week, ensuring further circulation in Product Hunt’s newsletter. 

Launching the new Generalist

We unveiled The Generalist's new home in January of this year, moving off of Substack. As part of that shift, we launched a private community and premium subscription product. This was the first time The Generalist began to earn revenue. 

As with my full-time announcement, I shared the news on social channels. A lot of amazing friends, collaborators, and supporters helped get the word out.  

Red Bull thread goes viral

After publishing my piece on Red Bull, I wrote a thread unpacking how the beverage company manufactures nothing, focusing on marketing instead. 

Was it the cover image? The copy? Whatever did the trick, the tweets went viral, receiving more than 8,000 likes and 2,400 retweets. From there, it attracted attention on Reddit and Hacker News.

Can we extract any wisdom from these episodes? It feels foolish to look for sense amidst randomness, but there are three lessons that have stayed with me. 

First: social media is a slot machine. It’s worth recognizing that going in, because if you try too hard to “game” one of these platforms, you can drive yourself crazy. Posting on Twitter and LinkedIn has proven a solid way to attract new subscribers, but it’s hard to know what will take off. I remember debating whether I should post my Red Bull thread for example — I wasn’t convinced anyone would want to read it. Conversely, there have been dozens of threads I’ve thought were interesting but were met with a shrug. I’ve learned to keep playing the game without letting it consume me. (For the most part.) 

Second: try and take advantage of launch moments. These are opportunities to tell your story and capture a reader’s imagination. One of the best decisions I made early on was to create an engaging deck for The Generalist ​​— it showed I was taking creating seriously, and gave me the space to cast a wider vision. Some of The Generalist’s fiercest supporters and believers were convinced by that initial presentation. 

Finally: social media can redress power imbalances. Durable Capital had far greater resources than I did. But because I was able to articulate the reasonableness of my position online, The Generalist successfully fended off spurious allegations. I don’t recommend picking fights, but it’s worth knowing that you may have more power than you think if you’re backed into a corner. 

With growth covered, it’s time to see how attention has translated into revenue. 

Business model: Half-baked

At the beginning of this piece, I promised to assess The Generalist with a sober gaze. With that in mind, I have to admit that I have yet to find the perfect business model. 

This seems like a rather ludicrous thing to admit in a piece that I hope will convince more of you to either subscribe or become a member. Why would you join something that is only partially baked? 

While it might sound strange, The Generalist actually seems to be doing a solid job creating value, but a bad job capturing it. People continue to share, sign up, and open the newsletter. I gratefully receive messages of support and enjoyment every week. The community NPS is very high. But on a number of metrics, The Generalist is doing a sub-par job. 

Revenue

So far, The Generalist has made money in three ways: subscriptions, sponsorships, and NFT sales. Before fees, that totals roughly $308,000. 

Subscriptions are the largest source of revenue. 

Since launching in late January, The Generalist has brought aboard 947 members — still short of the “1,000 true fans” metric. Of those, 433 are on the annual plan, 380 are on the monthly plan, and 134 are Believers, which is a five-year plan. 

That has resulted in bookings of $232,000 before fees. After fees, that comes in at $206,000. 

Of course, revenue is lower, given that it is recognized over the period paid for. The Generalist’s ARR currently stands at $176,000, with MRR at $14,700. Growth has slowed significantly over the last two months. 

Churn has been low, and currently sits at 3.86%. This has been helped by discontinuing monthly plans, which ran counter to my goal of building a long-term community. I personally reach out to every single person that churns to understand why they left.

So, are these numbers good? 

From one vantage: holy sh*t! The Generalist has outstripped the optimistic revenue goal I set last year. If I choose to, I could pay myself a great salary — better than I’ve received in the past. That is, frankly, amazing. 

But being ruthless, it’s clear there’s a lot to be improved upon. With 947 members and roughly 40,600 subscribers, The Generalist’s conversion from free to paid is just 2.3%. Some media experts I’ve spoken to have said that’s not bad, while others noted that similar subscription products can crest 10% conversion. From my vantage, it's clear I am doing a sub-standard job explaining to readers why they should become members.

I think that’s down to three reasons: 

  1. I’ve taken a light touch. I’ve only sent one dedicated email encouraging readers to become members, and haven’t introduced any kind of FOMO functionality (“buy in the next 24 hours for $5 off!”), or drip campaign. Your trust is The Generalist’s most vital asset, and I haven’t wanted to risk that.
  2. I’ve been trying to sell too many benefits at once. When I first kicked off The Generalist’s paid tier, I was still publishing startup ideas, interviews, and more frequent S-1s. It was tricky to sell all of those things — ideas! investments! trends! — coherently. As I’ve dialed in on The Generalist’s true value, this has become easier. 
  3. The Generalist is...general. Subscription products tend to work best for niche audiences with a high willingness to pay. Lenny Rachitsky’s excellent newsletter, for example, targets product managers and serves them perfectly. Since you know you’re going to receive insights that make you better at your job, subscribing becomes a no-brainer; you may even be able to expense it. While The Generalist provides that benefit for lots of people some of the time, it doesn’t do it for one group, all of the time. One week you might hear about a Kazak super-app, the next about a mesmerizing crypto project, and the one after that you’ll hear my musings on power in venture capital. 

Can these weaknesses be improved upon? Undoubtedly. I’m confident we can be more direct in expressing The Generalist’s value without losing trust, aided by increased clarity. But I don’t want to tighten the scope too much or lose the multidisciplinary approach. That’s what makes The Generalist what it is. 

One way to increase revenue without niching down is through sponsorships. To date, The Generalist has worked with a handful of partners, bringing in roughly $60,000 in revenue. It should be noted that each partnership has featured slightly different arrangements and payment structures.

It’s clear that there’s a lot more that could be done here. Again, my reticence has been driven by a desire to guard reader trust, but in surveying dedicated audience members, I’ve learned that most would support more sponsors if it allowed content to be shared openly, or put The Generalist onto stronger footing as a business. 

Packy has done an exceptional job in this respect, keeping all of his content free and monetizing through sponsorships and sponsored deep dives that are authentic to his brand. Could The Generalist try something similar? 

There may be an opportunity to work with aligned companies to tell their story, with integrity, while bringing in more resources to the business. By my own calculations, The Generalist could add 10x the revenue through such advertisements as it would through subscriptions over the next twelve months. What could we do with greater resources? 

Our final source of revenue to date prompts intriguing ideation: NFT sales. In March of this year, The Generalist raised 20 ETH to fund the creation of a report on Coinbase’s IPO. In exchange, contributors received $GENERALIST tokens. The goal was to experiment at the intersection of writing, NFTs, and community.

That resonated. 

We crowdsourced the funds quickly, splitting them between existing Generalist members, contributing writers, and illustrator Jack Butcher of Visualize Value. This process, in and of itself, was spellbinding to me, providing a mechanism to reward disparate stakeholders. 

But it was what happened after publication that was most thrilling. We sold three NFTs that corresponded to the piece we had written and featured Jack’s elegant artwork. Together, those sold for 28 ETH. In three weeks, holders of $GENERALIST had empowered communal creation and secured a ~30% return. 

The Generalist earned roughly 5 ETH from this experiment, about $16,000 at the time of writing. While that might have been more easily earned in other ways, this was a particularly satisfying experiment: everyone won together. 

Expenses

The proliferation of creator infrastructure has made it inexpensive to spin up a company like The Generalist. So, how have I ended up spending a total of $57,000 this year? Where has that money gone? 

As you might expect, merchant fees are the biggest line item: Stripe takes a cut for processing subscription payments. Pico does too, though that’s not reflected here. Not much to be done here for now. 

Second after merchant fees are contractor expenses. I’d like to protect the privacy of other parties here, so I won’t be too specific on costs, but here is the rough breakdown: 

  • Virtual assistant. I have an amazing VA who helps me with administrative items and customer support. This has unequivocally been a good investment in my view, giving me back time. That’s allowed me to focus on writing and researching, improving the quality of pieces. Added support also ensures The Generalist is able to respond to issues or questions faster. 
  • New website. Though I could have remained on a platform like Substack, I decided it was worth investing in a beautiful home for The Generalist. Was this money well-spent? I think so. It helps position The Generalist as something different, with a broader vision than being “a media company” or “newsletter.” I would like to think outside these lines. 
  • Building backend systems. I worked with a friend to build better underlying orchestration. Think Zapier and other no-code hookups. This was definitely helpful and should continue to save me time going forward. 
  • Miscellaneous projects. There have been a couple of projects that I once considered essential that have since been shelved. For example, I initially wanted to create a searchable, upvotable database for The Generalist’s startup ideas. I’ve since come to feel this is a distraction from refining the core product. This is no reflection on the people I worked with, just a change of strategy. In hindsight, I wish I had not commissioned these. 

It’s worth noting that in the period listed above, I had yet to pull a salary. In early August, I took my first dividend from The Generalist to pay for things like rent and food, which I enjoy. I intend to run as lean as possible and reinvest aggressively, but I will have to take money out intermittently. 

I am spending more than I would like to on software. This is an area I will keep an eye on, cutting unused services, and minimizing creep. Again, I don’t think it would be fair to comment on exact pricing here, but every so often writers will contact me asking me to share The Generalist’s stack. With that in mind, these are the tools I use at the moment ​​— some may change:  

The remaining categories from the “top 10 expenses” image above are relatively small and probably won’t change too much. I hope to keep having healthcare, find it necessary to pay for different publications to access information, and will occasionally need to consult lawyers and other professional service providers. 

One exception is events: I hope this increases in the year ahead. I hosted a small “1st birthday” party last week, which was a ton of fun. I want to meet and jam with many more of you, around the world, more often. 

Process: Solo and multiplayer

In the lead-up to this piece, I asked Twitter and The Generalist community what subjects they most wanted me to cover. I was surprised to see so many interested in digging into my writing process. I’m worried there isn’t a ton to say here, but I’ll do my best to talk through how things come together on both solo and multiplayer pieces. 

Solo 

It begins with ideation. I don’t have a formal content calendar, but I try to have pieces in mind a couple of weeks in advance. Sometimes, I’ll feel super organized and plan a month or more ahead but inevitably veer off and change tack. 

Ideas for pieces come from different places: Twitter, research papers, other newsletters, podcasts, and readers, to name a few. There’s no dedicated process I use to decide what's worth writing about. More than not, I’m just leaning into something I find intriguing, and want to learn more about myself and think readers would enjoy.

Sometimes I’ll try and gauge interest in those topics on social. For example, a few weeks before writing about Kaspi, I tweeted this:

Despite Kaspi being a company little-discussed beyond Central Asia, the response — though not effusive — suggested a degree of intrigue.

Once it’s time to turn that idea into a piece, I move into research mode. Sometimes, if I’m lucky, I’ll start researching the week before I need to write, but that’s a rarity. (I think it’s happened twice.) Usually, I’m starting on Monday or Tuesday, and continuing throughout the writing process. Increasingly, that research entails calls with sectoral or functional experts — as The Generalist has grown, I’ve found it easier to reach people with relevant experience.

The usual cadence goes something like this: 

  • Monday. Keep things relatively chill. Respond to messages, read, think. Spend some time outside. Take the day off, if feasible. (Has been in the last month!)
  • Tuesday. Get back up to speed as quickly as possible. Research by reading and talking to experts. Set up more calls. Respond to messages. Hang in the community and talk to friends. 
  • Wednesday. Start to feel a little pressure. Research more, talk to more people, begin to put an outline in place. Spend time in the community. 
  • Thursday. Begin writing. Get frustrated. Commit to writing at least a third of the piece. Fail. Commit to writing at least the introduction. Do an ok job. Drink some coffee. Try again. Have a good idea. Keep researching in the background. More community time and calls. 
  • Friday. Write. Coffee. Respond only to burning issues. 
  • Saturday. Get up early. Write. Respond to nothing. Try and complete a draft by end of the day. Maybe eat an almond croissant if I am feeling benevolent. Focus is narrow as a pinprick. 
  • Sunday. Get up at a silly hour, make an unsatisfying iced coffee, eat toast with peanut butter, read over the piece. Ask my fiancée Ali to give me her feedback. Edit. Frantically worry about illustrations after suddenly remembering I am a terrible artist. Scrawl and scrape to the finish line. Press send. Feel terrible about what I’ve written, to varying degrees. Emails. Sit in a chair and fall asleep. 

It’s worth saying: I really, really like doing this. This all might sound a bit intense and probably more emotional than it needs to be. But I’ve learned that I’m not the kind of writer that can produce work dispassionately — virtually everything I publish feels tied to my selfhood in a way that is not altogether healthy. If you’re of the same ilk, know that you have some company.

When it comes to writing, I don’t have any tricks, though I do have a kind of process. While I’m researching, I’m not just paying attention to the information collected. Indeed, more than any particular figure or fact, I’m trying to figure out the shape of something; the contours of what I’m writing about. What is it about this company or trend that animates it? What separates it from others? What is the source of its personality? And what does that tell us? 

You might call this the “hook” or “framing,” but that feels a little reductive. The point is not to land on something that catches attention (though it should do that too) but to uncover something true about a topic that can be articulated such that it reveals meaning

What does this look like? Many of the pieces I’m proudest of can be boiled down to just this central concept, and still make sense. For example: 

  • FTX is a speedrun. The crypto exchange is characterized both by velocity, and by what it chooses to leave behind in its pursuit of growth. 
  • Robinhood doesn’t know what party it’s throwing. The neobroker wants to be a social app with an economic agenda and a bank with a sense of humor. That identity crisis explains the tension between business model and product. 
  • Rocket Internet has no shame. Weirdly, that is actually the strength of the German incubator and investor. By deviating from entrepreneurial norms, it’s had an incredible impact on ecosystems around the world. 
  • Red Bull manufactures mythology. It doesn’t make its beverages, because it’s focused on producing something grander: history. By associating itself with sports teams and athletes, Red Bull imbricates itself into our cultural fabric. 

Finding the rationalizing force gives the piece a center of gravity, a weight, that often sticks with readers longer than the specific details of a company.

Once that’s settled, the rest of the piece is comparatively straightforward, though not quick or easy. Always, I want to write compellingly, elegantly, and with some flair.

After publishing, the final phase of work begins: sharing. I have no magic here. I post the piece on Twitter and LinkedIn and occasionally on Hacker News. Over the course of the next week, I post snippets, pulling out interesting graphs or statistics. Every once in a while, these missives take off. 

Multiplayer

At each stage, multiplayer pieces differ from solo affairs. As a refresher, these collaborations typically bring together 5-15 sectoral experts to work on a single briefing, like Tech in Africa.

First off, ideation has to occur far in advance of publication. Usually, you need at least 3 weeks to recruit contributors, host a discussion, and edit the piece. 

I’ll typically start pulling together a team by sending DMs to potential collaborators and putting out an ask on Twitter. Both have been helped by scale. For example, this tweet served as the starting point for a number of conversations with experts in African tech and venture capital. 

In my conversations with these experts, I emphasize that these collaborations are (i) a chance to share their knowledge with a large, influential audience, (ii) an opportunity to craft and contribute to a narrative that hopefully has enduring value in their industry, (iii) a fruitful structure to meet other relevant leaders, and (iv) an active way to learn and sharpen their thinking. 

This doesn’t appeal to everyone, but increasingly, I think leaders recognize the power that well-told stories can have. Being a part of one that might hold some sway in their sphere is often compelling. I also share a timeline upfront. 

Once the team has been set, I schedule a meeting for us all. That’s a chance for contributors to introduce themselves and begin brainstorming potential angles. While I prepare for these discussions, I try and speak as little as possible while maintaining conversational flow — I want to hear what these much more intelligent, knowledgeable people have to say about the subject matter. Inevitably, they highlight points I hadn’t considered and surface valuable resources. By doing so, we start to mould the shape of the piece together, removing unnecessary sections and adding more fruitful lines of inquiry. 

We end the call by dividing up the work. One person might commit to covering competition within an industry, while someone else wants to talk about the market. I do my best to divide up sections evenly, and always take one or two myself. Often, I’ll ask contributors to work together on a section — this adds a layer of accountability, while giving people a chance to get to know their co-authors better. 

With this set, everyone begins to research and write. Some will work straight in the shared Google Doc. This can be especially cool as it gives other participants a chance to weigh in and share their thoughts. It also prevents redundancies. Others reasonably prefer to operate independently, only sharing their section once complete. 

Getting contributors to finish their work is one of the hardest parts. Though everyone enters a collaboration with the best of intentions, life has a way of distracting and overwhelming at inopportune moments. That’s exacerbated by the fact that the typical contributor is in a senior position, balancing other major responsibilities. 

To try and avoid reaching the deadline to submit with the document half-bare, I overcommunicate with members of the team, checking in frequently. I reiterate that if they think they’ll have trouble hitting the deadline, that’s ok, but it’s helpful for me to know in advance.

Once I’ve received the different sections — or think I won’t receive any more — I jump in. While the team always shares incredible insights I could never have come up with myself, the different parts don’t mesh without editing. That’s natural, of course: folks have been working in relative isolation. 

This is where I try to add value. After reading everyone’s writing, I look for the piece’s organizing principle, just as I do when working solo. Often, this is harder to find with a multiplayer piece but it’s there, somewhere. Once I figure this part out, I move through the rest. I’ll shift some pieces around, combine sections, add whatever is missing. I’ll also edit for style to create a coherent, consistent voice — though it should feel like you’re accessing the brainpower of ten people, you don’t want to hear ten voices talking over each other. 

After publishing comes the (extra)fun part. If sharing solo work feels self-promotional, launching a multiplayer piece can feel like a celebration. You get to commend the work of the incredible people you’ve been getting to know, and can redirect the attention from yourself. By definition, these briefings feel larger than one’s self, because they are. 

This is also where one of the structural benefits of multiplayer pieces comes to the fore. Since numerous parties have contributed, you usually have multiple vectors for distribution. People are excited to share the work, resulting in its pollination of new audiences. 

Though often more effortful, multiplayer pieces can be particularly rewarding and uniquely powerful. Not only do you improve the calibre of analysis by harnessing collective intelligence, you create social capital between parties, make new friends, and bake in distribution advantages. 

Community: Inchoate magic

The Generalist community has caught me off guard. 

When I opened up access in January of this year, I hoped to build a place for thoughtful people to connect. I expected to find some new friends, and host some interesting conversations. But in the calibre of members, substance of interactions, and fearlessly creative ethos, I’ve been blown away. 

Yes, many of the members are exceptionally impressive people on paper. It has been crazy to see the GPs and CIOs of the world’s most influential funds, founders of notable startups, and C-Suite of some of my favorite public companies take the time to not only fill out an application thoughtfully, but contribute, meaningfully. 

More than the CVs of members though, it’s the uncommon thoughtfulness and openness that stand out. I feel confident saying this partially because earlier this week, a member shared their experience of the community. They’ve kindly allowed me to publish part of their message: 

(Brb, going to go cry.)

What’s amazing to me about this passage is (i) how clearly it articulates a feeling I’ve been having, (ii) how much room there is for improvement. 

Over the past eight months, it’s been incredible to see the community develop from a small cadre, kept interested by frequent prompting, into something increasingly engaged and self-governing. A few of the initiatives that are underway: 

  • Annika runs an investing book club
  • Colin hosts bi-weekly crypto chats. 
  • Luca hosts regular no-code chats. 
  • David is experimenting with AI meetups.
  • Alex is pulling together a communal fund to buy a small company. 
  • Adam manages a channel for media enthusiasts. 
  • Eli is pulling together a team to create “Generalist Guides” on finding your first job, investing in crypto, and other topics. 
  • Greg hosts a group that shares investment opportunities. 
  • Jim is hosting a club to talk about great longform reads in tech. 
  • Adam runs a discussion board for media enthusiasts. 
  • David runs a similar board for public market investors.  

(Aside: there are some amazing women in the community, but in these early months it has undeniably skewed male. This is something I’m actively thinking about and working to address going forward. I’d love to hear anyone’s thoughts on how to build online homes as inclusively as possible.)

These “Generalist GMs” are, increasingly, leaders of the community. Alongside these folks, there are dozens of others that take the time to spark conversation around things like longevity, solar power, NFTs, and much more. 

While these developments can quite literally keep me awake at night with excitement, we’re really just getting started. If I can provide the right support and infrastructure, what might this community look like in a year?

Alex might be running a company, partially owned by Generalist members. Eli could have published a series of guides, used by thousands to get up to speed on emergent topics. Greg might be organizing syndicates for members to fund companies alongside each other. Luca could be creating no-code tutorials for founders, or building infrastructure that makes the community better. Annika could be helming a podcast, interviewing some of the most experienced investors already in the community. Colin could be helping to launch our newest NFT game. 

This is just me dreaming aloud — of course, none of these things may happen. That’s ok. It's clear the Generalist community has some inchoate magic and plenty of potential. If I can protect this early flame, and give it oxygen, amazing things will happen. 

Future: Winning together

I always enjoy hearing what others think The Generalist will look like in five years. The range and nuance from community members and readers is striking. One will talk about it becoming a full-stack media company with podcasts, videos, and different newsletter products. Another thinks it will morph into a fund or syndicate, writing about the companies the group chooses to back. A third refers to the community, outlining the path to become a niche social network, a modern membership club, a DAO.

(And plenty of others probably think: it will be a newsletter. Duh.)

These conversations remind me of the parable of the blind men and the elephant, in which a group of sightless men try to explain to each other the beast on which they have placed their hands. One touches the trunk and declares that elephants are like snakes. The second marvels at a thick leg, suggesting the creature is like a tree. Another tests the sharpness of a tusk, believing that elephants are small and biting. The men argue, each believing he is the one to have correctly assessed what an elephant is and that his peers are fools. It’s only once a seeing man arrives that the group learns that an elephant is all of these things, but not just these things. 

I am not the seeing man. 

The reason I love hearing what others think The Generalist should become is because I don’t know. Rather than being some extra-dimensional visionary, I am as blind (and perhaps more so) as everyone else. 

I think that’s ok. It may even be desirable. The way companies and communities are being built is fundamentally changing. Yes, we still see great businesses forged by a dogged individual but increasingly entrepreneurial genius is collective (*gestures toward crypto*). Why can’t The Generalist be built this way?

One of my truest drives is the desire to win together. There’s something irresistible in not just triumphing, but doing so as a team, a squad, a community. The blind men may not have been able to see what was in front of them, but they could speak, couldn’t they? What would the parable tell us if it had ended not with the injection of a gifted interloper but with dialogue, proclamations of correctness giving way to questions? What if the blind men discovered what an elephant was together?

Though I have no answers of where The Generalist will go in the years ahead, this is the animating principle for the road ahead: discover and win, as a team. That opens up some fascinating possibilities, discussed below. Note, that none should be taken as a definitive statement of intent but rather a reflection of my current thinking. (Aside: you can help me figure out which of these to prioritize by completing this easy, 2-3 minute survey. It would mean a lot to hear your thoughts.)

DAO

One of my favorite questions from the Twitter post this week was this one: 

So, when DAO? 

Though a departure in some respects, this is an addition I think could make sense for The Generalist. Already, we have a strong community in place, have dabbled in crypto with the Coinbase piece, and have made multiplayer collaborations a central part of the product. All of those suggest a certain kinship with DAOs.

I’m just at the beginning of my thinking, but here’s how such a move might support and improve our work: 

  • Multiplayer contributors could be rewarded for their writing
  • Community leaders could be rewarded for facilitating online discussions
  • Local leaders could be rewarded for hosting meetups in their home city
  • Developers could be rewarded for building internal tooling
  • Investors could pool funds and organize investments
  • Members could vote on what topics to write about

In Multiplayer Media, I talked about my hope that, in the future, great works of art will be built with the help of thousands of contributors, similar to an open-source software product. Could The Generalist facilitate that? What would it look like if our Tech in Africa piece had not ten collaborators, but 1,000, with different parties being rewarded for their help researching, writing, editing, designing, and distributing? 

This is a speculative, far-reaching vision. It would take extraordinary coordination and luck. But I think even at a small scale it could create remarkable alignment. At the very least, contributors and members could be rewarded for their effort, building equity in the community in which they are spending their time. 

Funds and syndicates

Crypto is not the solution to everything. Indeed, many of the potential improvements listed above could be managed without drifting into DAOland. 

Investments are one such example. The Generalist deeply researches private companies and develops relationships with entrepreneurial leaders. I think that positions us well to assess high-potential startups and secure allocation in competitive rounds. Other creators have executed this playbook effectively, including Packy with Not Boring Capital, Harry Stebbings at 20VC, and Li Jin with Atelier

Vitally, I also think we’re able to offer a concrete value-add in a venture market that often looks homogenous. Startup founders that work with The Generalist could be assured distribution, access to an engaged and influential community, and assistance crafting a durable narrative. 

This can be powerful. In Whose Story Wins? I unpacked how only a handful of tech companies and venture funds have leveraged soft power effectively. Few things create a sense of destiny and magnetism around a business as powerfully as a good story, distributed widely. This should be something we can provide. It would be especially fun if community members were able to invest in these opportunities alongside The Generalist. 

There’s reason to tread carefully here, though. As I mentioned earlier, I can get easily energized by new ideas and opportunities. It’s tempting to spin-up something new, but each addition creates its own responsibilities. I wouldn’t want to bolt on such a significant business line without feeling that The Generalist’s model was firmly settled, the existing product would not suffer, and I (or someone else) could do justice to the investing game. 

For now, I think The Generalist is best served if I focus my time on writing and community. 

New products

There are a number of other products I would love to experiment with at some point. Many I outlined in this Disney-inspired drawing: 

Again, until I have nailed the basics I don’t think it’s smart to add too much. A few I’ve thought about beyond the image above: 

  • Playable case studies. Instead of reading a business case study, what if you could play it? I’d love to create text adventure games that ask the player to step into the role of an executive facing a tough problem and learn by venturing down different paths. I have made a basic version of this which I might share at some point. 
  • Video breakdowns. I think almost all of The Generalist’s deep dives could be turned into persuasive videos. Many might prefer to watch a 10 minute video that pulls out salient points than read a 30 minute article.  
  • Writing and storytelling course. While there are exceptions to the rule, I find most online writing advice uncreative. I think there’s room for more intellectually stimulating and multidisciplinary approaches.

Global hang

Though tentative, my hope is to spend much of the next few years outside the United States. Ali and I are both, amazingly, able to work remotely and it has been a dream of ours to spend a month or more in several global cities.

I think it could make for a particularly fulfilling endeavor for The Generalist. It remains astonishing to me that we have supporters, readers, and community members around the world — some of whom have already taken to arranging local meetups. I would love to get to know readers around the world, collaborate with folks in different ecosystems, and cover stories I might not have otherwise. A few (of the many) places we’d love to live: 

  • Shanghai
  • Nairobi
  • Lisbon
  • Cape Town
  • Hong Kong
  • Accra
  • Bombay
  • Taipei
  • Buenos Aires
  • Berlin
  • Tokyo
  • Singapore

How cool would it be if in twelve months time The Generalist has written about some of these ecosystems and the companies that define them, alongside local collaborators? How awesome would it be if we’ve interviewed or invested in founders from these countries? What new friendships and connections could be made hosting meetups and hangouts and all sorts of other social activities? 

That is something that would make me very happy. Let's put the events’ budget to good use.  

Gratitude

I don’t know where we will be in a year’s time, but I know that I am absurdly grateful for the year just past. I can’t miss the opportunity to say thank you to everyone that has helped The Generalist reach this point. 

Thank you to all of you, for spending your time with me, each week.

Thank you to both the readers and partners that support this work through their membership and sponsorships. 

Thank you to Ali, for improving everything I write. 

Thank you to my mother and sister, for making it seem totally reasonable to work on a newsletter full-time.

Thank you to Flavia, Renard, Michael, and Matteo for giving me a home on the other side of the country and being some of the earliest Generalist fans. 

Thank you to Annika and David for being the definition of true believers.

Thank you to Kashi for his care and wisdom

Thank you to the collaborators that shared their insight and effort so generously to create something worthwhile. May I have the fortune to multiplay many more games with Myles Danielsen, Richard Kim, Monica Desai Weiss, David Fauchier, Kyle Samani, Maria Shen, John O’Connell, Megan Kelly, Howard Lindzon, George Pearkes, Louis d'Origny, Meera Clark, Julie VerHage-Greenberg, Michael Sidgmore, Jake Gibson, Yoni Rechtman, Sid Jha, Tyler Tringas, Greg Isenberg, Nichole Yembra, Peter Kisadha, Iyinoluwa Aboyeji, Hayden Simmons, Steven Grin, Lewam Kefela, Dauda Barry, Abdul Ly, Aaron Fu, Chris Muscarella, Jamin Ball, Adrien Cipel, Nashilu Mouen-Makoua, David Wei, , Jeremy Diamond, Sumon Sadhu, Aashay Sanghvi, Jill Carlson, Ryan Todd, Katherine Wu, Lex Sokolin, Ellie Frost, Max Heald, Marc Rubinstein, Adam Draper, Ian Kar, Dave Ambrose, Courtney Buie-Lipkin, Kevin LaBuz, Nathan Baschez, Brian Schechter, Lucy Mort, Austin Rief, Adam Keesling, Justine Moore, Olivia Moore, Rex Woodbury, Jordan Banafsheha, Chris Brown, Austin Hankwitz, Eric Seufert, Chauncey TK Hamilton, Chris Kurdziel, Alice Lloyd George, Growf, Derek Urben, Brett Bivens, Bryant Jefferson, Nic Dardenne, Jake Singer, Sayshu Medicherla, Cristina Berta Jones, Avery Klemmer, Nandu Anilal, Michael Bloch, Ranjan Roy, Matt Newberg, Daniel McCarthy, Kevin LaBuz, Stew Bradley, Paul Barnes, Alex Lieberman, Tanay Jaipuria, Pranavi Cheemakurti, Karine Hsu, Jon Hale, Laurel Touby, Tanay Jaipuria, Byrne Hobart, Tina He, Justin Gage, Patrick O’Shaughnessy, Post Market, and Avery Klemmer

Thank you to my partners-in-crime, David, Ben, and Packy for being the best of fellow idea diners. 

Thank you to the braintrust, and many others that have offered advice and support along the way. With special thanks to Leif, Adam, Lenny, Dan, Li, Jack, Tom, Lillian, Brett, and Z

Thank you to the community members that have chosen to help me turn a patch of pixels into our own virtual city. With special gratitude to its most ardent leaders Greg, Courtney, Alex, the Davids, Colin, Erez, the Jims, Varun, Brian, Tina, Nick, Vic, Cy, Luca, Sajith, Sander, Clint, and many others. 

Thank you to anyone that has read even a single word of The Generalist, and to those that read all 400,000.

I could never have imagined how The Generalist would grow over the past year. I cannot wait to see what the next twelve months bring.

Help me chart the road ahead by completing this super-easy, 3 minute survey. Not only will it give me invaluable feedback, but it ensures The Generalist is built with you, the reader, at its heart. 

> Take The Generalist Survey

Help me chart the road ahead by completing this super-easy, 2-3 minute survey. Not only will it give me invaluable feedback, but it ensures The Generalist is built with you, the reader, at its heart. 

> Take The Generalist Survey

Last week, The Generalist turned 1.

As with many strokes of good fortune, it feels both as if it has been much longer and much shorter — like I might have started on a whim this afternoon, otherwise, a decade ago. Regardless of Time’s weight, in both cases, there is a familiar feeling that The Generalist is — I hope — just beginning. 

This has, without exaggeration, been the best 12 months of my life. I’m really not sure what I’ve done to deserve it. That’s been true both personally and professionally, in ways big and small. Some highlights:  

  • The Generalist surpassed 40,000 readers
  • Revenue outstrips my wildest goal for the year and the business is sustainable
  • I get to write every day and can feel myself getting better
  • I’ve gotten to deeply study some of the most fascinating companies and trends in the world
  • I’ve met and collaborated with people I respect and admire
  • Our community is full of some of the smartest, most thoughtful people I’ve ever met and that I want to be friends with IRL

I think I have had an extremely lucky start to life as an entrepreneur and public writer, but it has not been without incidence or adversity. I have worked harder on The Generalist than any other professional project. Growth has alternated between ahhhhh, sweet dopamine! to why, newsletter gods, why? A befuddled hedge fund threatened to sue me. 

But even those moments have brought a kind of joy; of putting one’s full effort forward, working on a worthwhile problem, pushing past friction. And, above all, of trying to build something bigger than one’s self. 

That is what gives me the greatest excitement when I think about The Generalist today. It has become much more than the brainchild of a single person, and my hope is that this will become increasingly the case in the years ahead. 

This piece is, in many respects, a (re)articulation of our shared vision and a reflection on what has brought us to this point. I’ll highlight both the good and bad of the last year, triumphs and failures. In particular, we’ll discuss:

  • Prologue. What came before The Generalist. 
  • Growing. Slot machines and structural hacks. 
  • Business model. Tentative moves and protecting trust. 
  • Writing process. How I write solo pieces and manage multiplayer. 
  • Community. Scaling belief. 
  • Future. What does the next year hold? 

Let’s begin. 

Prologue: How we got here

I’ve always found the trickiest part of a piece to write is the first sentence. Where should the story begin? The author has not only to commit to a time, a chronology, but an altitude. How high up should the reader be to see the shape you're drawing? How much detail should you show?

I feel the same tension here. What I really want to ask is: what do you want to know? Where do you want to start? 

I've chosen to begin where I might if someone close to me were to ask, “Why did you start The Generalist? What made you want to do that?” Forgive the biographizing such an origin entails. 

The truth is that I have always loved writing. I think everyone has a passion like this — something that you not only enjoy but confirms your sense of self. Sometimes we need time to find it but I am lucky to have discovered that activity early. Because I did, a not insignificant part of my childhood and adolescence was spent scrawling away at something. That continued through college, and beyond. One of the first things I did after leaving undergrad was register for night school classes in fiction writing, which led to joining a workshop.

Therein began a habit: for the next seven years, I would get up an hour early and go to a coffee shop to work on my novel, before beginning the day’s activities. I did that while failing at a lobotomizing law firm, moonlighting as a line cook, making time as a graduate student, and finally, building a career in tech.

This is still how I start most mornings: sitting at my computer, trying to move the novel forward, one sentence at a time. One day, I hope the book I have been writing since 2012 — it’s a near-future Künstlerroman set in Kathmandu, thank you for asking — feels finished, and worthy of soliciting a publisher. But even if that were to never happen, the book gave me a great gift; it was a project compelling enough to provoke practice. 

It made a difference. I reached a sufficient level to attain entrance to a few well-respected MFA fiction programs, and even though I did not attend, that gave me the confidence that I was not a total charlatan. Perhaps more importantly, writing became something I did, without much thinking. I got used to writing well on some days, badly on others, and bringing whatever I had cooked up to the workshop to accept critique. 

It was during my stint as a venture capitalist that I got up the courage to start sharing my work in public. By that point, I had developed a fascination with the tech sector that I’d exercised in different forms: “founding” a payments startup during my Master’s program, working at an incubator in Bogotá, running a sketchy ghost kitchen. 

An old boss of mine, Leif Abraham, encouraged me to use my passion for the written word to talk about tech. If I liked writing so much, why didn’t I write about the sector in which I was spending my days? When I didn’t pay much attention, he brought it up again a few months later, and again after that. Others encouraged me, too. 

In August of 2019, I decided to give it a shot. On a flight to San Francisco, I wrote the first draft of the first Generalist article. A few days later, I published 30 Minutes or Less: The Manufactured Urgency of YC Demo Day on Substack. 

The piece didn’t go viral or prompt a backlash. It was not hotly discussed nor worthy of much mention. But small things did happen: a few messages of appreciation, a question, a trickle of subscribers. Even tiny numbers seemed crazy, meaningful to me. Ten people had signed up? Ten people wanted to read what I had to say? 

In writing that first post, I had no intention to commit to a regular cadence. The Generalist would be akin to a Medium blog — somewhere to post musings when I got the chance. But I had so much fun that I didn’t want to stop. What if I wrote every day?.

I tried for exactly two days — but I am not Fred Wilson. I settled for a weekly cadence.

Now, as you may have noticed, that first salvo occurred two years ago. But for the twelve months that followed, The Generalist was a side-project, a hobby that bears only a passing resemblance to its current form. For one thing, the product was called “The Brunch Briefing" and was just a round-up of different links. I would sometimes write a longer introduction, and always tried to add a little razzle-dazzle, some strangeness, to the curation, but it had a weaker center of gravity.

Last summer I began to think of going full-time. It is a decision that makes very little sense, except in hindsight. The Generalist had earned $0 in revenue. It had attracted about 1,500 subscribers. It was, as I said, mostly a collection of links. 

But I couldn’t ignore how much fun I was having. 

At night, when I was trying to fall asleep, ideas for new stories, or formats filled my head. I experimented with many: trying out interviews, S-1 breakdowns, and Twitter digests. I loved hearing from readers and finding others with shared interests around the world. Surely, something worthwhile could be made. And what was the worst-case scenario? I was lucky to be able to go without a salary for a period of time, and I figured someone might still hire me if I flopped. 

On August 16 of last year, I announced my intention to go all-in. By then, The Generalist had reached 5,500 subscribers. As part of a larger presentation, I set out my goals for the next 12 months. I felt a little sheepish outlining such preposterous figures: 

Let’s see how we did. 

Growing: Lawsuits and lotteries

At the time of writing, these are The Generalist’s audience metrics: 

  • 40,606 subscribers
  • 49.93% open rate
  • 9.26% click rate

That represents 2x the subscriber count I set for myself last year, and roughly a 630% growth rate year over year. That’s been managed while keeping open rates largely stable, down from 51.53%. 

So, how did that happen? It’s required a mix of consistency, experimentation, and serendipity. 

Consistency

Whenever someone asks me how I’ve grown The Generalist, I’m always reluctant to share. Not because I have some closely-guarded secret but because my advice is so banal. The best way to build an audience is to create something people want, consistently. If you do that and share your work, you will grow. It really is that simple, and that difficult. It might not be as fast as you’d like, and there are certain techniques that can steepen the slope, but without nailing these basics, you’re fighting an uphill battle. 

Each component matters: 

  • Creating something people want. Not everything needs to be created with an audience in mind. Some of the great works of art could likely not have been constructed had the creator thought too closely about the viewer’s response. But if you seek to make creating your job, this is necessary. That doesn’t mean you have to take an obsequious stance towards the reader, or chase engagement above all else. But you need to find your people. My goal with The Generalist has been to write things that feel true to myself that also provide value and attract interest from others. 
  • Do it consistently. It’s very tempting not to create. Sure, sometimes the spirit moves you so strongly that you can’t help but write. But writing is effortful work, requiring a high cognitive load. (I read once that it’s roughly equivalent to playing elite chess, which I am skeptical of, but very much enjoy believing.) There are so many more pleasurable things you could do in your free time instead — eat peanut butter on toast, watch Love Island, nap. How can we stave off such glorious sloth? A commitment to consistency. Setting a cadence forces practice, improving your work. It also helps readers perceive your writing as a product, and one that can be relied upon.
  • Share your work. It’s hard to know what people want. The best way to figure it out is to share what you’ve created and get feedback. Use that to iterate and improve. Of course, without sharing your work, you also can’t hope to attract an audience. This is tricky to start with — it feels self-promotional because it quite literally is. Bit by bit, it becomes easier. Reframing sharing one’s work as beginning a conversation rather than asking for attention helps, too. 

So, the biggest reason The Generalist has grown is that I write something that some people like, reliably. That has meant that The Generalist’s largest source of growth, by some distance, is direct. Happy readers tell their friends, who tell their friends. 

Similarweb

While I’d love to be more proactive in encouraging explicit referrals, and up my SEO game, I hope that direct traffic will remain The Generalist’s largest traffic source in the years ahead. 

Experimentation

You may have noticed The Generalist has streamlined. Look, for example, at this slide from last year’s launch deck: 

At the time, The Generalist was experimenting with six different newsletters. Why so many? Why not try and nail one first? 

The most truthful answer is that I find it easy to get excited by new ideas and can let that get the best of me. But it also reflected my mindset: I wanted to build a creator business like a software company, testing out different products, and iterating quickly. 

By and large, I think that approach has served me well. Though The Generalist has since slimmed down, each of these products taught me something valuable that informs how I approach the weekly briefing. Interviews like The Miss or The Prologue encouraged me to take a closer look at management teams, treating my analysis like a psychological profile. Organizing S-1 Clubs sparked my thinking around multiplayer media, a key part of The Generalist’s model. 

In trying to find product-market fit, I’ve found it helpful to experiment with the explicit goal of increasing The Generalist’s “value over replacement.” In the age of endless content, more than ever, there’s a need to differentiate your writing from others, ideally in a manner that cannot easily be replicated. 

The Generalist (or The Brunch Briefing in those days) began with a product that had low value over replacement: a link roundup. Yes, I added commentary and curated differently than another creator might. But anyone that found such topics interesting could choose from a multitude of similar properties, many with more established reputations. Why not choose Morning Brew? How about The Hustle or The Download? 

Over time, I honed The Generalist’s value over replacement, finding ways I could separate myself from other creators and publications. I’ve found three primary differentiators: 

  1. Writing style and storytelling. Though there’s plenty of business coverage, a lot of it is perfunctorily written. I strive to create separation by focusing on storytelling and putting great care into the crafting of sentences. Reading The Generalist’s analysis of a company should feel exciting and absorbing. I also often look to frame these narratives in larger historical, philosophical, or psychological contexts. The result is hopefully a piece that feels intellectually rich, is worthy of your attention, and will shape your thinking. 
  2. Depth and thoroughness. We have plenty of places to read fundraising news, but fewer publishers dig deeply into a company or trend, explaining how it operates, from multiple angles. Those that do, often are conducting highly-priced equity research. The Generalist is hopefully of equivalent or better quality than these alternatives at 1/1000th of the price. 
  3. Creating conversation and connection. The writing can be just the beginning, if you let it. As often as possible, I bring kindred spirits into a conversation either through multiplayer pieces, community discussions, or events. That’s not unique, but also not typical. 

I’ve done a poor job capturing data, but triangulating between sign-up spikes, social shares, and anecdotal evidence seems to suggest that the most popular pieces have hit at least two of these dimensions, and often all three: 

  • Stripe: Thinking Like a Civilization. This was one of my most deeply-researched pieces, coming in above 12,000 words. I conducted about ten interviews and reviewed private transcripts to form my opinion. I framed my analysis with a story that, though a little grand, captured part of what makes Stripe special. 
  • Tech in Africa. This was a multiplayer piece and benefitted from the expertise and insights of ten other collaborators including fund managers and founders. Those people brought context on what it’s like to build and invest across the African continent with a rigor I could not have achieved through solitary research. We went deep and sparked a conversation online. 
  • The Mythology of Red Bull. Crazily, this piece was originally paywalled, but it still took off. I’ll share more on that below. It was really the storytelling around how the company harnesses “mythology” and differentiates itself from other beverage brands that captured most attention. 
  • Coupang: The Art of Obsession. This was another multiplayer piece, with seven other collaborators. The team really brought the heat when it came to analysis, especially in dissecting Coupang’s logistical infrastructure. We also hosted an event after publishing. 
  • FTX Trilogy. Though more recent, all three editions of the FTX Trilogy have done well so far. Much of this was due to the unparalleled amount of information I was able to access. Sam Bankman-Fried, FTX’s CEO, shared a well-stocked data room that I used to shed light on the business. By covering it across three pieces, I was also able to give the company the depth and nuance it merited. I’d like to do more series like this one. 

Going forward, these are the pieces I intend to use as models, with the goal of maximizing “value over replacement” along the three stated dimensions. 

(Of course, I’m not alone in trying to manifest compelling, deeply-researched, connective stories. Some of my favorites creators include Packy McCormick of Not Boring and David Rosenthal and Ben Gilbert of Acquired, who are masters of this.)

Ultimately, I could not have landed on these differentiators without experimenting with product lines and content formats. 

Serendipity

The final growth hack is, of course, luck. Not much of a hack. Every once in a while, something you do attracts sufficient attention to spike your growth. 

So, what drove The Generalist’s jumps? 

Going full-time 

As mentioned, last year I announced that I was going all-in on building The Generalist. I shared the news on social with a deck outlining my plans and goals. People responded positively and new readers flooded in.

Compoundergate

In October, I worked with a collaborator to write a piece on “compounders”: companies that grow reliably over time. The use of that word, and phrases like “good to great” angered a partner of Durable Capital, a $6 billion hedge fund. That partner alleged the piece relied on proprietary information (it did not), and threatened to sue my $0 in revenue newsletter. After trying and failing to find an amicable solution, I told the story in The Six Billion Dollar Stare and on Twitter. It led to an outpouring of support from fintwit, as Durable was meme’d into a hasty retreat.  Investing legend Dan Loeb even tweeted his support. (Thank you again to everyone that helped.)

The S-1 Club lists on Product Hunt

In November, we took The S-1 Club to Product Hunt, and managed to rack up more than 1,000 upvotes. We finished as the #4 launch that week, ensuring further circulation in Product Hunt’s newsletter. 

Launching the new Generalist

We unveiled The Generalist's new home in January of this year, moving off of Substack. As part of that shift, we launched a private community and premium subscription product. This was the first time The Generalist began to earn revenue. 

As with my full-time announcement, I shared the news on social channels. A lot of amazing friends, collaborators, and supporters helped get the word out.  

Red Bull thread goes viral

After publishing my piece on Red Bull, I wrote a thread unpacking how the beverage company manufactures nothing, focusing on marketing instead. 

Was it the cover image? The copy? Whatever did the trick, the tweets went viral, receiving more than 8,000 likes and 2,400 retweets. From there, it attracted attention on Reddit and Hacker News.

Can we extract any wisdom from these episodes? It feels foolish to look for sense amidst randomness, but there are three lessons that have stayed with me. 

First: social media is a slot machine. It’s worth recognizing that going in, because if you try too hard to “game” one of these platforms, you can drive yourself crazy. Posting on Twitter and LinkedIn has proven a solid way to attract new subscribers, but it’s hard to know what will take off. I remember debating whether I should post my Red Bull thread for example — I wasn’t convinced anyone would want to read it. Conversely, there have been dozens of threads I’ve thought were interesting but were met with a shrug. I’ve learned to keep playing the game without letting it consume me. (For the most part.) 

Second: try and take advantage of launch moments. These are opportunities to tell your story and capture a reader’s imagination. One of the best decisions I made early on was to create an engaging deck for The Generalist ​​— it showed I was taking creating seriously, and gave me the space to cast a wider vision. Some of The Generalist’s fiercest supporters and believers were convinced by that initial presentation. 

Finally: social media can redress power imbalances. Durable Capital had far greater resources than I did. But because I was able to articulate the reasonableness of my position online, The Generalist successfully fended off spurious allegations. I don’t recommend picking fights, but it’s worth knowing that you may have more power than you think if you’re backed into a corner. 

With growth covered, it’s time to see how attention has translated into revenue. 

Business model: Half-baked

At the beginning of this piece, I promised to assess The Generalist with a sober gaze. With that in mind, I have to admit that I have yet to find the perfect business model. 

This seems like a rather ludicrous thing to admit in a piece that I hope will convince more of you to either subscribe or become a member. Why would you join something that is only partially baked? 

While it might sound strange, The Generalist actually seems to be doing a solid job creating value, but a bad job capturing it. People continue to share, sign up, and open the newsletter. I gratefully receive messages of support and enjoyment every week. The community NPS is very high. But on a number of metrics, The Generalist is doing a sub-par job. 

Revenue

So far, The Generalist has made money in three ways: subscriptions, sponsorships, and NFT sales. Before fees, that totals roughly $308,000. 

Subscriptions are the largest source of revenue. 

Since launching in late January, The Generalist has brought aboard 947 members — still short of the “1,000 true fans” metric. Of those, 433 are on the annual plan, 380 are on the monthly plan, and 134 are Believers, which is a five-year plan. 

That has resulted in bookings of $232,000 before fees. After fees, that comes in at $206,000. 

Of course, revenue is lower, given that it is recognized over the period paid for. The Generalist’s ARR currently stands at $176,000, with MRR at $14,700. Growth has slowed significantly over the last two months. 

Churn has been low, and currently sits at 3.86%. This has been helped by discontinuing monthly plans, which ran counter to my goal of building a long-term community. I personally reach out to every single person that churns to understand why they left.

So, are these numbers good? 

From one vantage: holy sh*t! The Generalist has outstripped the optimistic revenue goal I set last year. If I choose to, I could pay myself a great salary — better than I’ve received in the past. That is, frankly, amazing. 

But being ruthless, it’s clear there’s a lot to be improved upon. With 947 members and roughly 40,600 subscribers, The Generalist’s conversion from free to paid is just 2.3%. Some media experts I’ve spoken to have said that’s not bad, while others noted that similar subscription products can crest 10% conversion. From my vantage, it's clear I am doing a sub-standard job explaining to readers why they should become members.

I think that’s down to three reasons: 

  1. I’ve taken a light touch. I’ve only sent one dedicated email encouraging readers to become members, and haven’t introduced any kind of FOMO functionality (“buy in the next 24 hours for $5 off!”), or drip campaign. Your trust is The Generalist’s most vital asset, and I haven’t wanted to risk that.
  2. I’ve been trying to sell too many benefits at once. When I first kicked off The Generalist’s paid tier, I was still publishing startup ideas, interviews, and more frequent S-1s. It was tricky to sell all of those things — ideas! investments! trends! — coherently. As I’ve dialed in on The Generalist’s true value, this has become easier. 
  3. The Generalist is...general. Subscription products tend to work best for niche audiences with a high willingness to pay. Lenny Rachitsky’s excellent newsletter, for example, targets product managers and serves them perfectly. Since you know you’re going to receive insights that make you better at your job, subscribing becomes a no-brainer; you may even be able to expense it. While The Generalist provides that benefit for lots of people some of the time, it doesn’t do it for one group, all of the time. One week you might hear about a Kazak super-app, the next about a mesmerizing crypto project, and the one after that you’ll hear my musings on power in venture capital. 

Can these weaknesses be improved upon? Undoubtedly. I’m confident we can be more direct in expressing The Generalist’s value without losing trust, aided by increased clarity. But I don’t want to tighten the scope too much or lose the multidisciplinary approach. That’s what makes The Generalist what it is. 

One way to increase revenue without niching down is through sponsorships. To date, The Generalist has worked with a handful of partners, bringing in roughly $60,000 in revenue. It should be noted that each partnership has featured slightly different arrangements and payment structures.

It’s clear that there’s a lot more that could be done here. Again, my reticence has been driven by a desire to guard reader trust, but in surveying dedicated audience members, I’ve learned that most would support more sponsors if it allowed content to be shared openly, or put The Generalist onto stronger footing as a business. 

Packy has done an exceptional job in this respect, keeping all of his content free and monetizing through sponsorships and sponsored deep dives that are authentic to his brand. Could The Generalist try something similar? 

There may be an opportunity to work with aligned companies to tell their story, with integrity, while bringing in more resources to the business. By my own calculations, The Generalist could add 10x the revenue through such advertisements as it would through subscriptions over the next twelve months. What could we do with greater resources? 

Our final source of revenue to date prompts intriguing ideation: NFT sales. In March of this year, The Generalist raised 20 ETH to fund the creation of a report on Coinbase’s IPO. In exchange, contributors received $GENERALIST tokens. The goal was to experiment at the intersection of writing, NFTs, and community.

That resonated. 

We crowdsourced the funds quickly, splitting them between existing Generalist members, contributing writers, and illustrator Jack Butcher of Visualize Value. This process, in and of itself, was spellbinding to me, providing a mechanism to reward disparate stakeholders. 

But it was what happened after publication that was most thrilling. We sold three NFTs that corresponded to the piece we had written and featured Jack’s elegant artwork. Together, those sold for 28 ETH. In three weeks, holders of $GENERALIST had empowered communal creation and secured a ~30% return. 

The Generalist earned roughly 5 ETH from this experiment, about $16,000 at the time of writing. While that might have been more easily earned in other ways, this was a particularly satisfying experiment: everyone won together. 

Expenses

The proliferation of creator infrastructure has made it inexpensive to spin up a company like The Generalist. So, how have I ended up spending a total of $57,000 this year? Where has that money gone? 

As you might expect, merchant fees are the biggest line item: Stripe takes a cut for processing subscription payments. Pico does too, though that’s not reflected here. Not much to be done here for now. 

Second after merchant fees are contractor expenses. I’d like to protect the privacy of other parties here, so I won’t be too specific on costs, but here is the rough breakdown: 

  • Virtual assistant. I have an amazing VA who helps me with administrative items and customer support. This has unequivocally been a good investment in my view, giving me back time. That’s allowed me to focus on writing and researching, improving the quality of pieces. Added support also ensures The Generalist is able to respond to issues or questions faster. 
  • New website. Though I could have remained on a platform like Substack, I decided it was worth investing in a beautiful home for The Generalist. Was this money well-spent? I think so. It helps position The Generalist as something different, with a broader vision than being “a media company” or “newsletter.” I would like to think outside these lines. 
  • Building backend systems. I worked with a friend to build better underlying orchestration. Think Zapier and other no-code hookups. This was definitely helpful and should continue to save me time going forward. 
  • Miscellaneous projects. There have been a couple of projects that I once considered essential that have since been shelved. For example, I initially wanted to create a searchable, upvotable database for The Generalist’s startup ideas. I’ve since come to feel this is a distraction from refining the core product. This is no reflection on the people I worked with, just a change of strategy. In hindsight, I wish I had not commissioned these. 

It’s worth noting that in the period listed above, I had yet to pull a salary. In early August, I took my first dividend from The Generalist to pay for things like rent and food, which I enjoy. I intend to run as lean as possible and reinvest aggressively, but I will have to take money out intermittently. 

I am spending more than I would like to on software. This is an area I will keep an eye on, cutting unused services, and minimizing creep. Again, I don’t think it would be fair to comment on exact pricing here, but every so often writers will contact me asking me to share The Generalist’s stack. With that in mind, these are the tools I use at the moment ​​— some may change:  

The remaining categories from the “top 10 expenses” image above are relatively small and probably won’t change too much. I hope to keep having healthcare, find it necessary to pay for different publications to access information, and will occasionally need to consult lawyers and other professional service providers. 

One exception is events: I hope this increases in the year ahead. I hosted a small “1st birthday” party last week, which was a ton of fun. I want to meet and jam with many more of you, around the world, more often. 

Process: Solo and multiplayer

In the lead-up to this piece, I asked Twitter and The Generalist community what subjects they most wanted me to cover. I was surprised to see so many interested in digging into my writing process. I’m worried there isn’t a ton to say here, but I’ll do my best to talk through how things come together on both solo and multiplayer pieces. 

Solo 

It begins with ideation. I don’t have a formal content calendar, but I try to have pieces in mind a couple of weeks in advance. Sometimes, I’ll feel super organized and plan a month or more ahead but inevitably veer off and change tack. 

Ideas for pieces come from different places: Twitter, research papers, other newsletters, podcasts, and readers, to name a few. There’s no dedicated process I use to decide what's worth writing about. More than not, I’m just leaning into something I find intriguing, and want to learn more about myself and think readers would enjoy.

Sometimes I’ll try and gauge interest in those topics on social. For example, a few weeks before writing about Kaspi, I tweeted this:

Despite Kaspi being a company little-discussed beyond Central Asia, the response — though not effusive — suggested a degree of intrigue.

Once it’s time to turn that idea into a piece, I move into research mode. Sometimes, if I’m lucky, I’ll start researching the week before I need to write, but that’s a rarity. (I think it’s happened twice.) Usually, I’m starting on Monday or Tuesday, and continuing throughout the writing process. Increasingly, that research entails calls with sectoral or functional experts — as The Generalist has grown, I’ve found it easier to reach people with relevant experience.

The usual cadence goes something like this: 

  • Monday. Keep things relatively chill. Respond to messages, read, think. Spend some time outside. Take the day off, if feasible. (Has been in the last month!)
  • Tuesday. Get back up to speed as quickly as possible. Research by reading and talking to experts. Set up more calls. Respond to messages. Hang in the community and talk to friends. 
  • Wednesday. Start to feel a little pressure. Research more, talk to more people, begin to put an outline in place. Spend time in the community. 
  • Thursday. Begin writing. Get frustrated. Commit to writing at least a third of the piece. Fail. Commit to writing at least the introduction. Do an ok job. Drink some coffee. Try again. Have a good idea. Keep researching in the background. More community time and calls. 
  • Friday. Write. Coffee. Respond only to burning issues. 
  • Saturday. Get up early. Write. Respond to nothing. Try and complete a draft by end of the day. Maybe eat an almond croissant if I am feeling benevolent. Focus is narrow as a pinprick. 
  • Sunday. Get up at a silly hour, make an unsatisfying iced coffee, eat toast with peanut butter, read over the piece. Ask my fiancée Ali to give me her feedback. Edit. Frantically worry about illustrations after suddenly remembering I am a terrible artist. Scrawl and scrape to the finish line. Press send. Feel terrible about what I’ve written, to varying degrees. Emails. Sit in a chair and fall asleep. 

It’s worth saying: I really, really like doing this. This all might sound a bit intense and probably more emotional than it needs to be. But I’ve learned that I’m not the kind of writer that can produce work dispassionately — virtually everything I publish feels tied to my selfhood in a way that is not altogether healthy. If you’re of the same ilk, know that you have some company.

When it comes to writing, I don’t have any tricks, though I do have a kind of process. While I’m researching, I’m not just paying attention to the information collected. Indeed, more than any particular figure or fact, I’m trying to figure out the shape of something; the contours of what I’m writing about. What is it about this company or trend that animates it? What separates it from others? What is the source of its personality? And what does that tell us? 

You might call this the “hook” or “framing,” but that feels a little reductive. The point is not to land on something that catches attention (though it should do that too) but to uncover something true about a topic that can be articulated such that it reveals meaning

What does this look like? Many of the pieces I’m proudest of can be boiled down to just this central concept, and still make sense. For example: 

  • FTX is a speedrun. The crypto exchange is characterized both by velocity, and by what it chooses to leave behind in its pursuit of growth. 
  • Robinhood doesn’t know what party it’s throwing. The neobroker wants to be a social app with an economic agenda and a bank with a sense of humor. That identity crisis explains the tension between business model and product. 
  • Rocket Internet has no shame. Weirdly, that is actually the strength of the German incubator and investor. By deviating from entrepreneurial norms, it’s had an incredible impact on ecosystems around the world. 
  • Red Bull manufactures mythology. It doesn’t make its beverages, because it’s focused on producing something grander: history. By associating itself with sports teams and athletes, Red Bull imbricates itself into our cultural fabric. 

Finding the rationalizing force gives the piece a center of gravity, a weight, that often sticks with readers longer than the specific details of a company.

Once that’s settled, the rest of the piece is comparatively straightforward, though not quick or easy. Always, I want to write compellingly, elegantly, and with some flair.

After publishing, the final phase of work begins: sharing. I have no magic here. I post the piece on Twitter and LinkedIn and occasionally on Hacker News. Over the course of the next week, I post snippets, pulling out interesting graphs or statistics. Every once in a while, these missives take off. 

Multiplayer

At each stage, multiplayer pieces differ from solo affairs. As a refresher, these collaborations typically bring together 5-15 sectoral experts to work on a single briefing, like Tech in Africa.

First off, ideation has to occur far in advance of publication. Usually, you need at least 3 weeks to recruit contributors, host a discussion, and edit the piece. 

I’ll typically start pulling together a team by sending DMs to potential collaborators and putting out an ask on Twitter. Both have been helped by scale. For example, this tweet served as the starting point for a number of conversations with experts in African tech and venture capital. 

In my conversations with these experts, I emphasize that these collaborations are (i) a chance to share their knowledge with a large, influential audience, (ii) an opportunity to craft and contribute to a narrative that hopefully has enduring value in their industry, (iii) a fruitful structure to meet other relevant leaders, and (iv) an active way to learn and sharpen their thinking. 

This doesn’t appeal to everyone, but increasingly, I think leaders recognize the power that well-told stories can have. Being a part of one that might hold some sway in their sphere is often compelling. I also share a timeline upfront. 

Once the team has been set, I schedule a meeting for us all. That’s a chance for contributors to introduce themselves and begin brainstorming potential angles. While I prepare for these discussions, I try and speak as little as possible while maintaining conversational flow — I want to hear what these much more intelligent, knowledgeable people have to say about the subject matter. Inevitably, they highlight points I hadn’t considered and surface valuable resources. By doing so, we start to mould the shape of the piece together, removing unnecessary sections and adding more fruitful lines of inquiry. 

We end the call by dividing up the work. One person might commit to covering competition within an industry, while someone else wants to talk about the market. I do my best to divide up sections evenly, and always take one or two myself. Often, I’ll ask contributors to work together on a section — this adds a layer of accountability, while giving people a chance to get to know their co-authors better. 

With this set, everyone begins to research and write. Some will work straight in the shared Google Doc. This can be especially cool as it gives other participants a chance to weigh in and share their thoughts. It also prevents redundancies. Others reasonably prefer to operate independently, only sharing their section once complete. 

Getting contributors to finish their work is one of the hardest parts. Though everyone enters a collaboration with the best of intentions, life has a way of distracting and overwhelming at inopportune moments. That’s exacerbated by the fact that the typical contributor is in a senior position, balancing other major responsibilities. 

To try and avoid reaching the deadline to submit with the document half-bare, I overcommunicate with members of the team, checking in frequently. I reiterate that if they think they’ll have trouble hitting the deadline, that’s ok, but it’s helpful for me to know in advance.

Once I’ve received the different sections — or think I won’t receive any more — I jump in. While the team always shares incredible insights I could never have come up with myself, the different parts don’t mesh without editing. That’s natural, of course: folks have been working in relative isolation. 

This is where I try to add value. After reading everyone’s writing, I look for the piece’s organizing principle, just as I do when working solo. Often, this is harder to find with a multiplayer piece but it’s there, somewhere. Once I figure this part out, I move through the rest. I’ll shift some pieces around, combine sections, add whatever is missing. I’ll also edit for style to create a coherent, consistent voice — though it should feel like you’re accessing the brainpower of ten people, you don’t want to hear ten voices talking over each other. 

After publishing comes the (extra)fun part. If sharing solo work feels self-promotional, launching a multiplayer piece can feel like a celebration. You get to commend the work of the incredible people you’ve been getting to know, and can redirect the attention from yourself. By definition, these briefings feel larger than one’s self, because they are. 

This is also where one of the structural benefits of multiplayer pieces comes to the fore. Since numerous parties have contributed, you usually have multiple vectors for distribution. People are excited to share the work, resulting in its pollination of new audiences. 

Though often more effortful, multiplayer pieces can be particularly rewarding and uniquely powerful. Not only do you improve the calibre of analysis by harnessing collective intelligence, you create social capital between parties, make new friends, and bake in distribution advantages. 

Community: Inchoate magic

The Generalist community has caught me off guard. 

When I opened up access in January of this year, I hoped to build a place for thoughtful people to connect. I expected to find some new friends, and host some interesting conversations. But in the calibre of members, substance of interactions, and fearlessly creative ethos, I’ve been blown away. 

Yes, many of the members are exceptionally impressive people on paper. It has been crazy to see the GPs and CIOs of the world’s most influential funds, founders of notable startups, and C-Suite of some of my favorite public companies take the time to not only fill out an application thoughtfully, but contribute, meaningfully. 

More than the CVs of members though, it’s the uncommon thoughtfulness and openness that stand out. I feel confident saying this partially because earlier this week, a member shared their experience of the community. They’ve kindly allowed me to publish part of their message: 

(Brb, going to go cry.)

What’s amazing to me about this passage is (i) how clearly it articulates a feeling I’ve been having, (ii) how much room there is for improvement. 

Over the past eight months, it’s been incredible to see the community develop from a small cadre, kept interested by frequent prompting, into something increasingly engaged and self-governing. A few of the initiatives that are underway: 

  • Annika runs an investing book club
  • Colin hosts bi-weekly crypto chats. 
  • Luca hosts regular no-code chats. 
  • David is experimenting with AI meetups.
  • Alex is pulling together a communal fund to buy a small company. 
  • Adam manages a channel for media enthusiasts. 
  • Eli is pulling together a team to create “Generalist Guides” on finding your first job, investing in crypto, and other topics. 
  • Greg hosts a group that shares investment opportunities. 
  • Jim is hosting a club to talk about great longform reads in tech. 
  • Adam runs a discussion board for media enthusiasts. 
  • David runs a similar board for public market investors.  

(Aside: there are some amazing women in the community, but in these early months it has undeniably skewed male. This is something I’m actively thinking about and working to address going forward. I’d love to hear anyone’s thoughts on how to build online homes as inclusively as possible.)

These “Generalist GMs” are, increasingly, leaders of the community. Alongside these folks, there are dozens of others that take the time to spark conversation around things like longevity, solar power, NFTs, and much more. 

While these developments can quite literally keep me awake at night with excitement, we’re really just getting started. If I can provide the right support and infrastructure, what might this community look like in a year?

Alex might be running a company, partially owned by Generalist members. Eli could have published a series of guides, used by thousands to get up to speed on emergent topics. Greg might be organizing syndicates for members to fund companies alongside each other. Luca could be creating no-code tutorials for founders, or building infrastructure that makes the community better. Annika could be helming a podcast, interviewing some of the most experienced investors already in the community. Colin could be helping to launch our newest NFT game. 

This is just me dreaming aloud — of course, none of these things may happen. That’s ok. It's clear the Generalist community has some inchoate magic and plenty of potential. If I can protect this early flame, and give it oxygen, amazing things will happen. 

Future: Winning together

I always enjoy hearing what others think The Generalist will look like in five years. The range and nuance from community members and readers is striking. One will talk about it becoming a full-stack media company with podcasts, videos, and different newsletter products. Another thinks it will morph into a fund or syndicate, writing about the companies the group chooses to back. A third refers to the community, outlining the path to become a niche social network, a modern membership club, a DAO.

(And plenty of others probably think: it will be a newsletter. Duh.)

These conversations remind me of the parable of the blind men and the elephant, in which a group of sightless men try to explain to each other the beast on which they have placed their hands. One touches the trunk and declares that elephants are like snakes. The second marvels at a thick leg, suggesting the creature is like a tree. Another tests the sharpness of a tusk, believing that elephants are small and biting. The men argue, each believing he is the one to have correctly assessed what an elephant is and that his peers are fools. It’s only once a seeing man arrives that the group learns that an elephant is all of these things, but not just these things. 

I am not the seeing man. 

The reason I love hearing what others think The Generalist should become is because I don’t know. Rather than being some extra-dimensional visionary, I am as blind (and perhaps more so) as everyone else. 

I think that’s ok. It may even be desirable. The way companies and communities are being built is fundamentally changing. Yes, we still see great businesses forged by a dogged individual but increasingly entrepreneurial genius is collective (*gestures toward crypto*). Why can’t The Generalist be built this way?

One of my truest drives is the desire to win together. There’s something irresistible in not just triumphing, but doing so as a team, a squad, a community. The blind men may not have been able to see what was in front of them, but they could speak, couldn’t they? What would the parable tell us if it had ended not with the injection of a gifted interloper but with dialogue, proclamations of correctness giving way to questions? What if the blind men discovered what an elephant was together?

Though I have no answers of where The Generalist will go in the years ahead, this is the animating principle for the road ahead: discover and win, as a team. That opens up some fascinating possibilities, discussed below. Note, that none should be taken as a definitive statement of intent but rather a reflection of my current thinking. (Aside: you can help me figure out which of these to prioritize by completing this easy, 2-3 minute survey. It would mean a lot to hear your thoughts.)

DAO

One of my favorite questions from the Twitter post this week was this one: 

So, when DAO? 

Though a departure in some respects, this is an addition I think could make sense for The Generalist. Already, we have a strong community in place, have dabbled in crypto with the Coinbase piece, and have made multiplayer collaborations a central part of the product. All of those suggest a certain kinship with DAOs.

I’m just at the beginning of my thinking, but here’s how such a move might support and improve our work: 

  • Multiplayer contributors could be rewarded for their writing
  • Community leaders could be rewarded for facilitating online discussions
  • Local leaders could be rewarded for hosting meetups in their home city
  • Developers could be rewarded for building internal tooling
  • Investors could pool funds and organize investments
  • Members could vote on what topics to write about

In Multiplayer Media, I talked about my hope that, in the future, great works of art will be built with the help of thousands of contributors, similar to an open-source software product. Could The Generalist facilitate that? What would it look like if our Tech in Africa piece had not ten collaborators, but 1,000, with different parties being rewarded for their help researching, writing, editing, designing, and distributing? 

This is a speculative, far-reaching vision. It would take extraordinary coordination and luck. But I think even at a small scale it could create remarkable alignment. At the very least, contributors and members could be rewarded for their effort, building equity in the community in which they are spending their time. 

Funds and syndicates

Crypto is not the solution to everything. Indeed, many of the potential improvements listed above could be managed without drifting into DAOland. 

Investments are one such example. The Generalist deeply researches private companies and develops relationships with entrepreneurial leaders. I think that positions us well to assess high-potential startups and secure allocation in competitive rounds. Other creators have executed this playbook effectively, including Packy with Not Boring Capital, Harry Stebbings at 20VC, and Li Jin with Atelier

Vitally, I also think we’re able to offer a concrete value-add in a venture market that often looks homogenous. Startup founders that work with The Generalist could be assured distribution, access to an engaged and influential community, and assistance crafting a durable narrative. 

This can be powerful. In Whose Story Wins? I unpacked how only a handful of tech companies and venture funds have leveraged soft power effectively. Few things create a sense of destiny and magnetism around a business as powerfully as a good story, distributed widely. This should be something we can provide. It would be especially fun if community members were able to invest in these opportunities alongside The Generalist. 

There’s reason to tread carefully here, though. As I mentioned earlier, I can get easily energized by new ideas and opportunities. It’s tempting to spin-up something new, but each addition creates its own responsibilities. I wouldn’t want to bolt on such a significant business line without feeling that The Generalist’s model was firmly settled, the existing product would not suffer, and I (or someone else) could do justice to the investing game. 

For now, I think The Generalist is best served if I focus my time on writing and community. 

New products

There are a number of other products I would love to experiment with at some point. Many I outlined in this Disney-inspired drawing: 

Again, until I have nailed the basics I don’t think it’s smart to add too much. A few I’ve thought about beyond the image above: 

  • Playable case studies. Instead of reading a business case study, what if you could play it? I’d love to create text adventure games that ask the player to step into the role of an executive facing a tough problem and learn by venturing down different paths. I have made a basic version of this which I might share at some point. 
  • Video breakdowns. I think almost all of The Generalist’s deep dives could be turned into persuasive videos. Many might prefer to watch a 10 minute video that pulls out salient points than read a 30 minute article.  
  • Writing and storytelling course. While there are exceptions to the rule, I find most online writing advice uncreative. I think there’s room for more intellectually stimulating and multidisciplinary approaches.

Global hang

Though tentative, my hope is to spend much of the next few years outside the United States. Ali and I are both, amazingly, able to work remotely and it has been a dream of ours to spend a month or more in several global cities.

I think it could make for a particularly fulfilling endeavor for The Generalist. It remains astonishing to me that we have supporters, readers, and community members around the world — some of whom have already taken to arranging local meetups. I would love to get to know readers around the world, collaborate with folks in different ecosystems, and cover stories I might not have otherwise. A few (of the many) places we’d love to live: 

  • Shanghai
  • Nairobi
  • Lisbon
  • Cape Town
  • Hong Kong
  • Accra
  • Bombay
  • Taipei
  • Buenos Aires
  • Berlin
  • Tokyo
  • Singapore

How cool would it be if in twelve months time The Generalist has written about some of these ecosystems and the companies that define them, alongside local collaborators? How awesome would it be if we’ve interviewed or invested in founders from these countries? What new friendships and connections could be made hosting meetups and hangouts and all sorts of other social activities? 

That is something that would make me very happy. Let's put the events’ budget to good use.  

Gratitude

I don’t know where we will be in a year’s time, but I know that I am absurdly grateful for the year just past. I can’t miss the opportunity to say thank you to everyone that has helped The Generalist reach this point. 

Thank you to all of you, for spending your time with me, each week.

Thank you to both the readers and partners that support this work through their membership and sponsorships. 

Thank you to Ali, for improving everything I write. 

Thank you to my mother and sister, for making it seem totally reasonable to work on a newsletter full-time.

Thank you to Flavia, Renard, Michael, and Matteo for giving me a home on the other side of the country and being some of the earliest Generalist fans. 

Thank you to Annika and David for being the definition of true believers.

Thank you to Kashi for his care and wisdom

Thank you to the collaborators that shared their insight and effort so generously to create something worthwhile. May I have the fortune to multiplay many more games with Myles Danielsen, Richard Kim, Monica Desai Weiss, David Fauchier, Kyle Samani, Maria Shen, John O’Connell, Megan Kelly, Howard Lindzon, George Pearkes, Louis d'Origny, Meera Clark, Julie VerHage-Greenberg, Michael Sidgmore, Jake Gibson, Yoni Rechtman, Sid Jha, Tyler Tringas, Greg Isenberg, Nichole Yembra, Peter Kisadha, Iyinoluwa Aboyeji, Hayden Simmons, Steven Grin, Lewam Kefela, Dauda Barry, Abdul Ly, Aaron Fu, Chris Muscarella, Jamin Ball, Adrien Cipel, Nashilu Mouen-Makoua, David Wei, , Jeremy Diamond, Sumon Sadhu, Aashay Sanghvi, Jill Carlson, Ryan Todd, Katherine Wu, Lex Sokolin, Ellie Frost, Max Heald, Marc Rubinstein, Adam Draper, Ian Kar, Dave Ambrose, Courtney Buie-Lipkin, Kevin LaBuz, Nathan Baschez, Brian Schechter, Lucy Mort, Austin Rief, Adam Keesling, Justine Moore, Olivia Moore, Rex Woodbury, Jordan Banafsheha, Chris Brown, Austin Hankwitz, Eric Seufert, Chauncey TK Hamilton, Chris Kurdziel, Alice Lloyd George, Growf, Derek Urben, Brett Bivens, Bryant Jefferson, Nic Dardenne, Jake Singer, Sayshu Medicherla, Cristina Berta Jones, Avery Klemmer, Nandu Anilal, Michael Bloch, Ranjan Roy, Matt Newberg, Daniel McCarthy, Kevin LaBuz, Stew Bradley, Paul Barnes, Alex Lieberman, Tanay Jaipuria, Pranavi Cheemakurti, Karine Hsu, Jon Hale, Laurel Touby, Tanay Jaipuria, Byrne Hobart, Tina He, Justin Gage, Patrick O’Shaughnessy, Post Market, and Avery Klemmer

Thank you to my partners-in-crime, David, Ben, and Packy for being the best of fellow idea diners. 

Thank you to the braintrust, and many others that have offered advice and support along the way. With special thanks to Leif, Adam, Lenny, Dan, Li, Jack, Tom, Lillian, Brett, and Z

Thank you to the community members that have chosen to help me turn a patch of pixels into our own virtual city. With special gratitude to its most ardent leaders Greg, Courtney, Alex, the Davids, Colin, Erez, the Jims, Varun, Brian, Tina, Nick, Vic, Cy, Luca, Sajith, Sander, Clint, and many others. 

Thank you to anyone that has read even a single word of The Generalist, and to those that read all 400,000.

I could never have imagined how The Generalist would grow over the past year. I cannot wait to see what the next twelve months bring.

Help me chart the road ahead by completing this super-easy, 3 minute survey. Not only will it give me invaluable feedback, but it ensures The Generalist is built with you, the reader, at its heart. 

> Take The Generalist Survey

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