#5 — September 2025
- Planted:
Interviewing people for my book has been so much fun.
One startup COO I interviewed took two <24 hour round-trip flights to Italy during peak COVID to persuade a Swedish company to sell their domain for six figures, only to have the money go missing for a couple months after the seller sent the wrong banking wire instructions. That story and interview will likely end up in an email newsletter, which you can sign up for at dotcom.press.
Writing
I started doing some work for Val Town, helping out with their docs and blog. I published my first blog post yesterday: In, Val, Out
Earlier this week I wrote about how to find a domain for your startup, which is essentially the blog post version of a talk I’m giving next week at a local startup conference.
A couple weeks ago I wrote about Google’s confusing involvement in the domains world while working out of the NYC Google office. The more I research the more I realize how many books could be written on single subtopics within the wider world of domains. There’s an amusing contrast when people ask what my book is about, depending on who’s asking. Most people say (or at least think) something like, “...a whole book?” Domains experts—brokers, investors, registrars, ICANN, etc.—say something like, “you need to narrow your scope.”
I also wrote about the et al of dot com et al, that is to say the 1,591 top-level domains other than .com. That number will continue to explode with a new round of domain extensions coming next year. You can even apply for your own .whatever if you have $227k lying around.
Conferences
On Monday the 6th I’ll be demo’ing some of the Dot Com Press tech stack at StartupCincy Week’s “Best of Demo Night.” Then on Wednesday I’m giving a talk on how to find the right domain for your startup. Whether or not you really do need a dot com has been at the top of my list of burning questions while writing the book (and it’ll continue to burn because it’s subjective, of course). Reply if you have anecdotes or opinions to share from your experience.
From October 25th to 30th I’ll be in Dublin, Ireland for ICANN84, the first of my back-to-back capital J Journalism trips. I’m reading Milton Mueller’s book, Declaring Independence in Cyberspace right now to prepare. I’m quite excited to build a holistic impression of ICANN by attending the six-day annual meeting IRL. I don’t think I’d be able to replicate that just by reading, attending webinars, and talking to current and former ICANN employees (although I am doing those things, too!).
My second research trip (I have actual “media passes” for these events) will be in Miami on November 5th and 6th for NamesCon. The conference has an investing angle, but the crowd will include registries, registrars, brokers, ICANN, ISPs, and IP lawyers. There’s even a live domain auction and literal server throwing competition.
Reading, watching
I finished reading The Anxious Generation by Jonathan Haidt. Like I wrote in August, it’s a book I plan to pick back up down the road as a parent with young kids.
I read Tabula Rasa by John McPhee. I really like the form factor of the book, which roughly matches what I think I want for my own: paperback, ~250 pages, simple but tasteful cover art. I like McPhee so far. I’m sort of studying his writing to learn about great nonfiction, but it’s also just pleasant. I checked out The Control of Nature and Draft No. 4 from the library.
I read Mr. Penumbra’s 24-Hour Bookstore by Robin Sloan. I get why people who work in tech read him. It’s page turning like a fantasy novel but you feel like something of an insider with all the startup references.
I read The Byline Bible by Susan Shapiro. The point is that you can be somewhat formulaic about submitting short nonfiction to publications, and eventually it’ll work. It’s something I’ve considered while working toward a full book.
We’ve been watching Hacks on HBO Max, and I’m surprised I haven’t heard more people talk about it. I also watched the first few episodes of The Paper (successor to The Office), and it’s pretty funny.
On New York City
I was in New York City for a week in September. I like to ask people who’ve lived in New York whether they feel like a New Yorker, which I think generally equates to being proud of the city and feeling confident you can live well in it, tradeoffs and all. I started to feel like a New Yorker in my second stint there (the first one interrupted by a Really Good year and change living with my brother Martin in Richmond), and I’ve held onto some residual New Yorker identity over the past couple years with Sloane in Cincinnati (which also qualify as Really Good, I’d say). We’re starting to think about moving back to NYC, which I bet would resurrect and deepen whatever latent New Yorker pride I have left (in an I-chose-this-so-I-must-like-it sort of way).