Introducing My Super Secret Diary

This newsletter exists so I can stop feeling like a hypocrite.

I recently started a new job as the Program Director for the On Deck Writer Fellowship, which is sort of like a startup accelerator for bloggers and newsletter authors.

But my dirty little secret is that I myself haven’t been writing publicly for years. I’ve long ago fallen off the wagon of my Medium essays. The last time I “wrote publicly” was when I won the New Yorker cartoon caption contest in February 2019—and that was only one sentence.

I was starting to feel like a huge fraud running a program to help people do something I wasn’t even doing myself. Hence, this newsletter.

Hi. It’s good to be here.

So what’s this newsletter about? It’s about whatever I want it to be about.

I would advise anyone trying to grow a significant audience to define their subject matter a little more precisely than “whatever I want.” But I’m not trying to grow a significant audience. All I care about is reaching what I call “Minimum Viable Audience”: just enough people reading this that I don’t feel like I’m shouting into the void—and that I feel obligated to keep writing it each week.

But if pressed—and since Substack requires a one-line description of what you’re writing about—I’d say this newsletter will be about startups, literature, philosophy, American history, sex & drugs, and how to be alive. (Sorry, mom.)

Along those lines, here are some of things you can expect to read about in the coming weeks (or not—I make no promises):

  • Why JFK was a bad President

  • My experience at a ten-day silent meditation retreat

  • Why I donate 10% of my income to charity (and why I find talking about that publicly embarrassing)

  • How Trump ruined acid

  • In defense of half-assing most things

Updates will come once a week, probably on weekends, hopefully on schedule. Thanks for coming along for this ride with me. It’s going to be entertaining, intellectually stimulating, and probably a little embarrassing.

Anxiously yours,


Read of the week: I really enjoyed this Smithsonian Magazine piece re-examining the Roman emperor Nero’s reputation, especially this bit positing that even if the story about him fiddling while Rome burned is true, we’ve been interpreting it the wrong way. It’s not the Roman version of George W. Bush continuing to read My Pet Goat after finding out about 9/11—it’s an emotional response to tragedy, coming from someone with an artist’s soul:

“We have a contemporaneous account by a witness to the Great Chicago Fire of 1871 who speaks of its ‘great beauty,’” says Anthony Barrett, professor emeritus at the University of British Columbia at Vancouver. “J. Robert Oppenheimer recited the Bhagavad Gita after witnessing the first explosion of the atom bomb. Scipio Africanus quoted Homer on seeing the destruction of Carthage. These are very human reactions to tragedy. Only in Nero is it seen as evil.”