The Generalist - The Generalist Turns 1

Good morning friends,

Today's email is a special one for me.

Last week marked the anniversary of my decision to go full-time on The Generalist. It has been an incredible, absurdly fulfilling 12 months, and has gone better than I could have hoped.

That is almost entirely down to people like you that read and support my work. To each and every one of you: thank you. I am so grateful to have you here every week. It has been a genuine privilege and pleasure.

To mark the occasion, I've turned The Generalist's gaze inwards — today's piece is The Generalist covering...The Generalist. Meta.

I've shared every number I can think of, highlighted the good times, been honest about my failures, and outlined how I'm thinking about the future. You're a big part of that. To that end, if there's just one thing you have a chance to do today for The Generalist, the most impactful would be to click the link below and complete this super-easy 2-3 minute survey:

> Survey (please fill out 🙏)

It would mean a lot to me, and will give me the invaluable feedback needed to make this next year even better than the last.

I can't wait for it. For now, let's dig in to how Year 1 has gone.

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.


All guesses welcome and clues given to anyone that would like one. Just respond to this email for a hint.

What four-letter word can be written forward, backward, or upside down, and can still be read from left to right? (Disclaimer: capital letters only.)

Last time around, I asked readers to share their favorite pieces of trivia. You all did not disappoint, with a lovely collection coming together. These were my favorites:

Area codes were assigned in the era of the rotary dial — the most populous cities got the shorter “throw.” Hence 212 for NYC.
The northernmost point in Brazil is closer to Canada than the southernmost point in Brazil.
The northernmost state in the continental US is Minnesota.
The unicorn is the national animal of Scotland.
Everest is actually, not the highest point on Earth when measured from the center of the earth (or another way to think about it, the point on earth that is closest to the Sun). Everest is the tallest mountain when measured from sea-level to peak, but Chimborazo, in Ecuador, is the highest point on Earth from Core-to-peak. That's in large part due to the equatorial bulge.

Thank you to all who participated, including Doug R, Jim W, Robert H, Keshav J, Diego P, Anna H, Taylor P, and RTT.

Wishing all of you a Sunday full of reflection. Please imagine me in my Brooklyn study, raising a tiny cup of espresso in appreciation for you all. You are the best.

With much gratitude,


PS - The Generalist will be observing Labor Day next weekend. We'll be back in your inboxes the week after, ready for a fiery fall.

PPS - If you haven't had a chance, I'd love to hear from you in this fast survey. It would mean a lot!

Key phrases

Older messages

FTX: The Everything Exchange

Sunday, August 15, 2021

​ Hey friends, I hope everyone's having a great weekend. This edition marks the finale of the FTX Trilogy, an investigation into crypto's wildest and fastest-growing exchange. If you're

FTX's speedrun

Sunday, August 8, 2021

​ Welcome to the 39797 kind and curious readers of The Generalist. It's so great to have you here! Today's piece is coming to you from Las Vegas, where I have been stealing away from a bachelor

The Prince of Risk

Sunday, August 1, 2021

​ Friends, A very happy Sunday to you all. I am so excited to be sharing this newest edition of The Generalist. When I started this week, I planned to do a traditional deep dive into FTX. As many of

Robinhood: Serious Fun

Sunday, July 18, 2021

​ The day has finally arrived. It's time for Robinhood. With an IPO around the corner, The Generalist pulled together one of our finest ever teams to cover the controversial brokerage firm. This

What to Watch in Crypto

Sunday, June 27, 2021

​ Good morning everyone, This week's piece is a little different. I've always been a fan of Bloomberg's series "Where to Invest." It asks great allocators where they would invest

Postdrips, Niirly, FirstDapp, Incept, and

Saturday, October 23, 2021

Simple one page LinkedIn scheduling tool BetaList BetaList Daily Postdrips Simple one page LinkedIn scheduling tool FirstDapp Easiest place to get access to DeFi indices Niirly Create connections - in

What's 🔥 in Enterprise IT/VC #260

Saturday, October 23, 2021

🙏🏼 5 years of What's 🔥!!! IT Spending 💰 forecasted to grow 📈 at fastest rate in over 10 years! ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌

🗞 What's New: Bitcoin hits a record $67K

Saturday, October 23, 2021

Also: Harness the power of "flow state" with these tips! ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌

Wealth, twitter fights, and gen-z

Saturday, October 23, 2021

​ Howdy! ​ Here's a few things I found lately that I think you'll enjoy: 💰 Thoughts on wealth, from Logic: Jordan Harbinger interviewed Logic (the rapper) on his podcast. Logic grew up poor,

The Trump SPAC frenzy, Tesla rides to a new high, and how new surveillance technology is reshaping U.S. neighborhoods

Saturday, October 23, 2021

View in browser October 22, 2021 Hello! As promised, we finally have an event site for our get-together next month with the full agenda and all the other deets you'll need. (Better late than never,

10words: Top picks from this week

Friday, October 22, 2021 Discover new apps and startups in 10 words or less Zuitte: Your Business, In One App™ To The Moon+: Making E-Commerce Apps work as play Mindleap: Mindleap brings advanced mental health

Bootstrapped Founder #107: Too Little, Too Much: Advice and How to Take It

Friday, October 22, 2021

​ The Bootstrapped Founder Logo ​ ​ Dear founder, "For even the very wise cannot see all ends." ― Gandalf, JRR Tolkien, The Fellowship of the Ring Whenever people talk about advice, they

Creating a successful podcast with Jane Portman

Friday, October 22, 2021

This week's episode of the Bootstrapped podcast is ready for you. Hi Bootstrappers, Today's episode of Bootstrapped continues the mini-season of interviews, while my co-host recovers from a

Small Business, Big Lessons: A new podcast by Buffer 🎧

Friday, October 22, 2021

Go behind the scenes with inspirational small businesses who are truly driving innovation and redefining how work happens. ‌ ‌ ‌ Image Happy Friday 👋 Yesterday, we launched a new podcast Small Business

Snap slips, Adam Neumann resurfaces. and how many users does Facebook have? The company isn't so sure

Friday, October 22, 2021

View in browser October 21, 2021 Hello! One quick mention before we finally put together an actual event website: We are *thrilled* about two more guests who are joining us Thursday evening, November