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August 17, 2020

Going All-In on The Generalist

Why I decided to leave my job in venture capital, and make writing online my life's work.

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Friends,

Time takes on funny shapes sometimes. Perfectly straight at times, symmetrical at others.

As I write this article, I am cognizant of a strange loop. One year ago, I published the first article of The Generalist. I wrote the piece in San Francisco — a city in which I do not live — sitting at the dining room table of my partner's family home. Twelve months later, to the day, I am back at the same table, in the same city.

It's been quite a year.

One year

Here's how it began.

Every six months, venture capitalists from around the world make a pilgrimage to Silicon Valley for Y Combinator's Demo Day. I was no exception. It was my second visit to the party, and though I was grateful to have been invited, I was concerned about the manufactured urgency of the accelerator and how that led to suboptimal partnerships. So I wrote about it.

I didn’t expect it to lead to anything. I was surprised when over the next few days and weeks, investors reached out, founders followed up, and readers shared stories of their own. A few people even signed up for a newsletter I wasn't sure what to do with: The Generalist.

It was the start of something. In the year since, I've written and published a further 70+ pieces and a newsletter that began with a few high school friends, some generous colleagues, and my mother, has grown into a 5,500+ community of thinkers, founders, writers, investors, skeptics, and supporters. In the scheme of things, these are small numbers, but I have felt a big change. In sharing my writing every week, in getting to know you all, in exchanging ideas, I have felt a sense of self I have not felt in adult life.

So with that, I'm leaning in. I’m excited to share with that I’ve decided to go all-in on The Generalist.

With gratitude to my colleagues at Charge and the singular Brett Martin, in particular, I'll remain involved as a Venture Partner at the fund, albeit in a minor key.

On its face, it may sound faintly ludicrous to step back from a job as a VC to build a newsletter. To write. But the growth and vibrancy of this community have given me the belief that we can build something great together. I'm excited to try and make it my life's work.​

What is The Generalist?

The Generalist is a media company and community dissecting tech from idea to IPO.

The pace of technological advancement is making generalists of us all. To keep up, we will all need to craft a fluid intelligence, a supple intellect. My hope is that The Generalist will be a publication for this new era and those that wish to define it.

No one succeeds alone, not even the solitary newsletter writer. My goal is for this to be a collective experiment, an extended collaboration of which we are all a part. To that end, I'm sharing my full business plan, including metrics-to-date, my plan for the future, the fears that keep me up at night, and growth strategies.

Check out the business plan

How will I make money? What will a community look like? How do RFS 100 and S-1 Club fit in? You can check it all out above. You'll notice I dedicate a slide to the values I hope come to define The Generalist. First among them is the commitment to "Build in Public." Which is to say, to operate with transparency in everything. Consider this the beginning of more sharing.

I'm eager to hear what you think and hope you'll be a part of this next chapter.​

I didn't sign up for a 61-page deck. Can I have a summary?

Very fair. Here are the highlights.

  • Why would you do this? Writing is my purest pleasure. Technology is my fascination. This is a perfect combination.
  • What's the opportunity? We're all consuming more media, and there's an increasing willingness to pay for high-quality content. The last year has also seen an explosion of great writers and analysts in the space — I believe we're at the start of a creator breakout. The rise of robust infrastructure makes scaling increasingly possible.
  • What is The Generalist? A media company and community focused on tech from idea to IPO. It spans a series of newsletters, including RFS 100, In Flight (coming soon), The Prologue, The Miss, The Weekly Briefing, and The S-1 Club.
  • What's happened so far? We've grown to 5,500+ members while maintaining strong open rates. I've also gotten to interview and collaborate with some of the people I admire most in the industry.
  • How will you make money? Subscriptions. Premium content will be available for $20/month, but existing members will get an early discount. I'm also going to experiment with courses and books.
  • How will you grow? Create high-quality content consistently. If I can't do that, I'll fail. I also wouldn't be proud of myself. Beyond that, I'll experiment with different platforms and mediums and republish pieces to meet readers where they are.
  • Who's behind this? Me. I've also built a "Braintrust" — a Board of Directors proxy — composed of founders, investors, and writers. These folks have generously agreed to advise me and push me to be better.
  • How might this fail? So many ways. I'm most worried about creating an overly broad offering and, as a result, not delivering as much quality as I'd like. I think I'm being clear-headed about my capabilities here, for the time being.
  • What are your goals for Year 1? Have fun, grow fast, make rent. (More details in the deck.)
  • How can I help? Thank you. That means a lot. The biggest thing is to help me grow. If you can send the email to friends, that would be huge, as would sharing on social media. Beyond that, I always really value hearing from you. Lastly, when we launch a premium plan, becoming a member would mean the world. More tangibly, it would help me survive.

Check out the business plan

Gratitude

“Let us be grateful to the people who make us happy; they are the charming gardeners who make our souls blossom.”

So said Marcel Proust. These days, I find I am grateful to a great many people.

First, my colleagues at Charge, and Brett Martin, in particular. Not only was he the person that gave me my first full-time job in venture, he was also one of the first people to encourage me to start sharing my writing online. I feel lucky I get to keep working with him and the team.

Second, the many lovely people who have supported, advised, and encouraged me. That includes my family and friends, of course, in addition to the names you'll find in the deck. Particular gratitude to those that have agreed to serve in the Braintrust including Zach Reitano, Courtney Buie-Lipkin, Blake Robbins, Nikhil Basu-Trivedi, Dave Ambrose, Turner Novak, Dan Shipper, Nathan Barry, Alex Lieberman, Packy McCormick, MW Floyd, Tina He, Aashay Sanghvi, Jonathan Libov, Leif Abraham, Brett Martin, Jimmy Shah, Meera Clark, and Nick deWilde.

Finally, you.

There is no way I can express my appreciation without sounding trite, but I can promise you this: it is truly felt. Thank you for being here.