Generalist updates
Jan 24, 2021

A Big Announcement

The revamped, reimagined Generalist is finally here. This is what it all means.

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What is a city, but the people; true the people are the city.

On Friday afternoon, I visited a friend. I took a cab to his place in Queens, watching out of the open window at the sunbleached streets of Dumbo and Greenpoint and finally, Long Island City. A cold day — sharp wind cutting across a tree-lined road — but beautiful in the fragility all bright winter days have.

From the top of a set of stone stairs, my friend waved. It was the first time I'd seen him in real life. Over an hour or so, we sat — six feet apart in a lovely living room — and talked. About tech and venture capital certainly, but other things, too. Books, writing, a stretch of land upstate, he hoped to one day build upon.

It was only on the way home that I realized, remembered how we had met. Something I'd written in the early days of The Generalist had resonated, and through a friend, we were introduced and hit it off. Over the better part of the year that followed, we talked over Zoom calls and text, worked on pieces together. In short, we became friends.

On the ride home, I thought about what had just happened. What struck me most was how normal it seemed, how unremarkable it is, now, to have a friendship forged without in-person socialization. All of us, in some capacity or another, have adapted our congeniality to the digital world.

And while we find some things missing from such encounters — a realness perhaps, a fidelity — other aspects are amplified. In predicting what the new year would bring, Chris Paik, a co-founder and partner of Pace Capital, noted:

The next big thing in 2021 is people realizing that serendipity happens more in our digital worlds...than in the analog one.

Though the last year has forced us to abandon the places in which we once met, to leave our offices and cities, it has — for many, at least — provided more opportunities to interact than ever. We may have retreated from our respective metropolises for the time being, but we have found and built digital cities brimming with energy, vitality, and real connection.

That is what we come to cities for, after all. The people, and what the people bring with them. The opportunity of a new or better job, the wisdom of others, the asset of a network, the attraction and amusement of shared endeavor.

This year has taught me that we can find each of these things online. And not only can we find them, we can access them readily and scalably. Pulling together a group of experts to dissect an S-1 filing can be managed with a few emails, Twitter posts, and Telegram messages. Some of the great investors and founders can be compelled to share startup ideas, or consent to an interview, without pre-emptive coffees or lunches. Social grease and goodwill can be built, sustainably, on digital ground.

And all of these things, these experiments, can extend and move and modulate far beyond their original purpose. An S-1 collaboration might morph into an investing club. A set of startup ideas might hatch a group chat. When you make a city out of software, this is what is unlocked. Yes, there are things you lose. But what you receive instead, the entity with which you are left, is fundamentally different from the territories to which we are accustomed; fluid, changeable, responsive to our needs and desires.

As I think about what I hope The Generalist becomes — what I believe it is already becoming — this is it. A streetless capital, a burg without buildings, a polis of pixels. In short, an invisible city.

(Re)introducing The Generalist

Welcome to the new Generalist. It looks a little different than you're used to.

In late August of last year, I decided to build a new website for The Generalist. In mid-September, I sent my first email to The Braintrust — the group of generous investors and operators I inveigled into advising this little venture. Dated September 18th, you can see my proposed goals.

I failed at all four. By October 1st, I'd reached just over 12K members. I was pleased with that (the 15K had been a stretch), but I also had no website, no premium plan, no formal community.

You'll see, too, that my mind was already spinning with the idea of membership. How could I make it feel special? How do you build intimacy online?

Four months later, I know I am just at the beginning of answering that question. But I believe I have found the right place to start. A patch of land we can build upon.

Why did it take so long?

Sometimes two truths compete.

Why did it take me four months longer than I'd planned to launch this site?

The truth: I can be particularly finicky, a perfectionist in the worst sense of the word. While I know the new Generalist isn't perfect, of course, I did agonize over each piece of it.

The greater truth: I was, and am, nervous.

There's something immensely comforting about writing for free. Like a mechanic that looks at a spluttering engine gratis and somehow adds a broken tail light to the mix, free offers a certain shield.

Didn't enjoy this week's piece? Well, at least, it was free.

Sometimes free is great. It makes it easier to start, to learn with less pressure. It gives people the chance to try out whatever it is you're building or creating without making a financial commitment. It also offers a capaciousness of ambition, an unwrittenness useful for a company just getting started.

For as long as The Generalist stayed free, it was easy for me to ignore the reality that, despite the momentum, for all my sense that something was really working, I had not built a business. Free is the creator version of quantum superposition: your project is both working and not working, headed skyward at the same time that it bleeds to death.

Again, something is comforting about this. A word I love: nikhedonia or the joy of anticipated success. Free is a knuckle of nikhedonia, potential energy, waiting to move.

At a certain point, though, that state stops serving you. To progress, you have to move. As one tech legend said this past year: it's time to build.

What does this mean?

There are now three tiers of membership to The Generalist.

Free members will receive 1 monthly briefing, IPO reports, startup ideas, and summarized interviews. For many, this plan might be perfect. Not every city will be for everyone. Maybe The Generalist is a place you want to visit every so often, rather than make a digital home and frequent conversational partner. That is totally ok, and I am very grateful for anyone that chooses to spend time with me through my work.

Premium members unlock in-depth analysis, new ideas, and open up a network. By joining, you'll receive 4 briefings a month, annotated S-1 filings in addition to IPO reports, extra startup ideas, and full interviews. You'll also earn access to the new Generalist community, via application.

This will be the home for The Generalist's most thoughtful, curious members. It's the place we'll unpack product ideas, talk through potential investments, respectfully exchange opinions, and sharpen our intellect through conversation. I'd love for you to be a part of it.

Believers are the crazy ones. Those for whom this vision resonates most clearly, and want to have a leading role in shaping what is to come. By joining as a Believer, you purchase five years of membership to The Generalist at a significant discount. You'll receive all the benefits of Premium, along with access to select community channels, events, and other surprises along the way.

If you’d like to become a member, you can do so by following the link, below.

> Become a member

Right now, the Premium tier is offered at a discounted price for those excited to jump aboard. Within the coming weeks, I will be raising it to $25 per month. If you have any questions, don't hesitate to shoot me an email.

Can you help?

Yes. Thank you.

The most helpful thing you could do right now is join. Become a paying member and help build this new city with me. Though creator-businesses are exciting partially because they can thrive with low costs, there are not no costs. By joining, you allow me to support myself, cover the cost of necessary tools, and keep improving and adding to the product. (I have a lot of ideas here). Just as importantly, you buy into this community; making it yours as much as mine.

Beyond joining, please tell others. Launch days are good moments to share, to get someone new excited about something. If you feel able to send an email to a few people, share on social media, or text a friend, I'd really appreciate it. I try not to make these asks often — only when they matter. Today is such a day.


I could not have done this without help. I am lucky to have gotten to work with two amazing designers JP and Ariana, who built this site. Abbas created some fantastic icons. And Jason, the CEO of Pico, responded to every email and Twitter DM to make sure the membership integration works as seamlessly as possible, even late on Friday night and all through Saturday.

I feel incredibly lucky to have gotten to work with such fantastic, generous people.

Lastly, there is, of course, only one place to end. Thank you to all of you, that make this possible. By spending time here each week, learning and thinking together, you allow me to make building The Generalist my life's work. I cannot wait for all the good we will do together — the companies that will arise from a shared startup idea, the investments that will come from our discussion, and the friendships that will be born, even if it might take some time for us to meet in person.

Because though we may be tied to earthly metropolises, in other realms, we may choose our cities. For what is a city, but the people.

The Generalist’s work is provided for informational purposes only and should not be construed as legal, business, investment, or tax advice. You should always do your own research and consult advisors on these subjects. Our work may feature entities in which Generalist Capital, LLC or the author has invested.