I’m not a phone person. So on the rare occasion I have a good phone call I remember it. Three years ago my friend Michael Williams called me to say his newsletter was live and it was going well. He suggested I start one too. Michael is smart about things like that and I listened carefully. In a fervor of inspiration after I hung up I started writing and sent one out right away. It was a Friday afternoon in August, probably the least opportune time to announce a new endeavor. But I knew if I analyzed things over the weekend I would lose my nerve.
I’m glad I didn’t wait. To my surprise, this newsletter has been a revelation—professionally and personally. I don’t know what I thought it would become, but it definitely became something else. About 280 newsletters later and 120-something podcasts, here we are. One of the good things about modern media is that the writer-reader relationship can be immediate. That’s particularly true in the back and forth of the question and answer sessions we do here. I started answer your questions the very first week of The Contender—were we ever so young?
So I want thank all of you. And of course Michael—I’m glad I listened to you, though I always am! Here are some other things I’ve learned about newsletters, the readers and myself over the last three years.
Personal is Better. A newsletter is not a magazine article. People subscribe to a magazine for many reasons, but in a newsletter they want a connection to the author. What you write shows up in their inbox, which is inherently intimate. At first I wrote longer essays that were more involved. Over time I made the stories shorter, breezier and more conversational. That seems to make sense for the medium. Readers generally like authority—they want your opinions. But they also want to admit when something is hard or when you’re wrong or this story about when I was losing focus and reading too little.
A Few Good Chinos. When we started doing Q&A sessions there were so many questions about chinos it became a running joke. Also: Oxford cloth shirts. What does this tell us? Well, people wear a lot of chinos and Oxfords, but also that they don’t love their choices. The bargain option feels imperfect and the most rarefied are too expensive. That speaks to a general life approach. RRL chinos are a crucial 10% better than others. But others are $80 and RRL are $225. So you have to ask yourself just how much is that last 10% worth? That’s an eternal question that only you can answer, whether it’s about chinos, a bottle of whisky, a fly rod, a camera or anything else.
Rules are Powerful. So are lists. Writers complain that web editors are always pushing 10 places to go and the rest of the deadly click baiters. We want to write meaningful essays from the heart! Well, at a newsletter you are the editor, the writer and the analytics guru. You see what people are reading and responding to. This story, What Every Man Should Own, changed the trajectory of this site more than anything else. It moved the newsletter from a hobby to how to make a living. So whatever else we say about lists, sometimes they land.
Idiosyncrasy Still Matters. But life is more than lists. And I think, for those of you considering starting a newsletter, variation is a good thing. Don’t be afraid of your weird obsessions. I know that my dad generally likes my more eccentric stories. I think of him when I write certain things. Here’s one on my love of ice, another on cologne and one on the rarely seen Full Cleveland. People connected to these more than I expected and I was glad to see that.
People Love Paris. I’m constantly surprised by endless Paris curiosity, particularly where to eat. I get asked about Paris restaurants so often I finally wrote this list just to end the discussion. But I’ll add this: we’re in an age of the recommendations. And there’s an art to asking for one. If I ask a friend who lives in Tokyo where to eat I don’t say: Where should I eat in Tokyo? There are places that cost $5 on a train platform and $500 in a hushed tatami room. How does he know what I’m looking for? So I ask as specifically as possible for a small traditional izakaya or a serene tempura place to break the bank.
The Internet Can Still Be Nice. One of the most rewarding parts of the newsletter is the evolution of the Q&A sessions. I love seeing readers give other readers well-meaning and genuinely helpful advice. This isn’t the comment section dogfight or the dreaded online discourse. It’s great to see people connecting and engaging in a big-hearted way, the way this was supposed to be!
Substack Keeps Getting Better. Just a word of praise for the host here. Substack has made things so much easier—being able to search archives, better design, recommendations between newsletters, the app, the notes—it’s really impressive. I think it’s a good place to host a website/newsletter, whether you’re going to charge or not.
Let the Thing Breathe. This is advice for anybody starting anything editorial. Of course you want to analyze what your site or magazine is going to be about. I used to make huge lists about what I was going to write about. And, if you go way back, I wrote newsletters almost every day when I began. Then you get real. You can’t plan everything out (or I can’t anyway). Some ideas succeed and become regular features. But more often than I would have expected I respond to something that happens to me—I go on a road trip, visit an Italian bar with a funny rule, my Vikings flame out of the playoffs—and I try to respond to that in, what I hope is, a meaningful way.
Advocate Some Principles. Any publication can be thematically wide-ranging, and probably should be. But there should remain some foundational premise. Over time that becomes more clear. One thing I wanted to make sure was that this never became a selling tool—you don’t need me telling you more things to buy. On the contrary, the idea is that you have fewer, better possessions that you carefully maintain. More than that, if I can say so, there are some ideas revisited in these pages, that you should: start traditions, tip well, don’t tell your entire life story on Instagram, don’t live in fear of dressing up, make your own way when you travel, write things down, remember that the most expensive option isn’t always the best and, crucially, pack light. Ask more of the things you buy and the places you patronize, but in the end ask the most of yourself.
Well, three years is not a bad run. I never thought I would be a newsletter evangelist. But sometimes certain things align. I’ve always loved editing and coming up with story ideas. And of course I love writing, though I didn’t realize how much I enjoyed the regular process of writing weekly stories. With the newsletter that came together with a third thing which was every bit as crucial: An audience of engaged, smart and I’d like to think dashing readers, who make this all work.
So I raise my glass to you. Here’s to another year of good knit ties, bad beer, brown trout, canvas bags, Argentinian grills, and who knows, maybe even Vikings success. After all, a man can dream, can’t he?
Salut!
David
Cheers, this newsletter was a delight in the covid doldrums, and it still stops me from doing whatever I should be doing when a new missive arrives in the inbox. Looking forward to many more.
I dare say that you deserve to cash in, and my suggestion is a "The Contender x J. Crew" chino pant, which can be billed as the first pant designed via Substack comments.
Congrats, David. I should have asked for 10% in perpetuity. Damn it.