The Contender Turns Six

I admire people who start things. Many of my friends are natural at opening restaurants or publishing magazines or designing clothes. I’m given to overthinking and never quite get going. That’s why I wouldn’t have started this newsletter if Michael (who’s famously proactive) hadn’t convinced me to do it on a Friday afternoon in August. I got off the phone with him and before better judgment kicked in I fired off a newsletter. Over the next week I sent one almost every day. Then came a Q&A, then we started a podcast, much later a newspaper.

Substack was different back then. There were far fewer people on it, for one thing. No app, no feed, no leaderboards. Now you don’t have to explain to anybody what Substack is, but I miss that intimate connection. Michael makes fun of me for celebrating these anniversaries, but it feels like the right day to thank you for being part of a newsletter with a dress code, as I called it back then. There would be no Contender without engaged, insightful and, dare I say, dashing readers.

We’ve covered a lot of ground—granular analysis of chinos and Oxford shirts, slowing down and paying closer attention. And, as travel changes, escaping the algorithm and the Hot List Mentality. In the last six years I’ve met many of you at signings and events, which is always great.

A newsletter has to have a theme and it has to evolve. Sometimes you answer questions you’re asked a lot (where to eat in Paris, how to buy a suit, what books to read), sometimes your topics are more eccentric (ice, rice cookers, 80s cologne). One thing I've learned is never to limit your scope of interest. If you’re obsessed with something off your beat don’t be afraid to cover that too, whether it’s spy novels, sad sports teams or the Westminster dog show.

A few other memorable posts: Rules for Modern Life is the most widely read piece I published. People like rules, what can I say! And here’s what I learned when I turned half a century old: Fifty at Fifty. What Every Man Should Own is when the newsletter became a way to make a living.

It sounds sentimental, but it’s true to say that this newsletter changed my life. Thanks for reading, for asking questions and for ignoring me about roller bags. But more than anything, thank you for holding The Contender to a standard I never imagined it could reach.