Let's start from the basics: can you introduce yourself?

I’m founder and CEO of Buttondown, the easiest way for you to start and grow a newsletter. My friends and I also purchase small software companies over at Third South Capital.

Beyond the work side of things: I live in Richmond, VA (having come back home to roost and live a few miles away from my parents, after spending the past decade in Seattle) and have a wife and corgi that, amongst other things, prevent me from working too much.

What's the story behind your blog?

I registered jmduke.com 15 years ago: it began as the stereotypical tech blog that undergraduate students are advised to create to bolster what might otherwise be an underwhelming resume. I realized that I actually really enjoyed the process: not just the writing, and trying to communicate otherwise anodyne concepts like How to use itertools in Python! in a voice that was friendly and interesting and crisp, but also the dopamine effect of hearing folks write in and say that they found my writing useful.

It’s gone on a series of reinventions since then: my ability to consistently write has waxed and waned, but I keep coming back to this notion — particularly lately — that building artifacts under my own domain’s auspices is more durable and valuable than throwing them out into the algorithmic ether.

What does your creative process look like when it comes to blogging?

My writing is pretty bimodal at this point: either short posts more akin to microblogging that feel akin to journaling or longer essays that take a month or more to really pull out and shape.

This is probably bad advice, or at least bad praxis, but for the former I intentionally eschew process — I’ve found that if I’m trying to communicate something at the object-level (“this is how I handled this problem”, “this is what I thought about this book”) the more time I spend on it, the worse it is.

Do you have an ideal creative environment? Also do you believe the physical space influences your creativity?

I don’t think I have an ideal environment, so much as I have non-ideal environments. I am super heavily influenced by the mental and emotional context of a place: to quote my wife, I can never take a day off inside my own house because everywhere I look I’m reminded of something to do.

When I need to really get into flow and write something — not just jot down a quick post or get some thoughts out of my head, but engage with writing as a form of problem-solving and digestion — I have to leave the house.

A question for the techie readers: can you run us through your tech stack?

This has changed a lot over the years, but right now I’m really happy with 11ty. It’s being hosted on Netlify (but that’s more of an implementation detail than anything; I could use any other service, I just already had a Netlify account) and is as painless as can be.

Given your experience, if you were to start a blog today, would you do anything differently?

A couple fairly trite answers here that are true despite their triteness:

• Consistency. I’m sure everyone says this, but: writing to me is sort of like exercise. It’s very easy to say “ah, I don’t have time to do this” and give it up, and then discover that there is some sort of gap in your soul, a bit of a spiritual unease and languor that comes from lack of creation and reflection.
• Portability. This is now largely a non-issue, but I spent my first few years using various platforms (Tumblr, Wordpress, Ghost) and not really trying to hold onto the backlog of posts. This meant shifting providers or changing my blog was extremely onerous, because I had to think about if it was worth porting content over.
• Earnestness. A few years into my career, I remember deleting a lot of older posts because I was embarrassed at how amateurish they were — “oh my god, I can’t have people thinking I was just writing about learning for loops!” I’d do anything to have those back.

Financial question since the Web is obsessed with money: how much does it cost to run your blog? Is it just a cost, or does it generate some revenue? And what's your position on people monetising personal blogs?

$0 cost (well, I guess $12/year for the domain), $0 revenue. Or to perhaps be a little more oblique: the blog itself is not literally monetized, but it is probably responsible for >80% of my net worth at this point.

I feel pretty confident that without blogging, I would have never broken into the industry the way that I did; and then, without blogging, I would have never made the social connections requisite to start Buttondown and have it be as successful as it is.

Time for some recommendations: any blog you think is worth checking out? And also, who do you think I should be interviewing next?

• I can think of few blogs that have influenced me personally more than Mandy Brown’s A Working Library. The combination of form, function, and a timeless design — plus the incorporation of rich media — remains a bit of a lodestar for me.
• A Collection of Mitigated Pedantry is to history as Matt Levine’s Money Stuff is to finance: a sheer delight, not just in the reading but in the learning.
• I came across Books & Boots six months ago when I was looking for discussion about Len Deighton’s work, and fell into an absolute wormhole of glorious literary criticism & analysis.

Final question: is there anything you want to share with us?

One of the things about this corner of the internet that I’m deeply grateful for is the humanity of it all: in a world that seems increasingly dominated by slop (generative AI, mass cold emails, SEO-optimized empty-calories content) it is both rarer and more valuable than ever to be able to forge a meaningful connection online. If there’s ever anything I can help the person reading this with, I’m at me@jmduke.com.