Justin Duke built buttondown for himself, but you can use it, too

The Stripe engineer who created a bespoke newsletter platform in his free time talks about the paradox at the heart of the passion economy.

A song to read by: “Small Town Talk,” by Bobby Charles

What I’m reading: “Conflict Is Not Abuse,” by Sarah Schulman


The newsletter platforms runneth over

While researching a story about newsletters for Business Insider the other week, I discovered that there is a truly gobsmacking number of newsletter platforms on the market. Most of them are fighting for a scrap of the email-marketing ecosystem, which is such a cherry pie that even a tiny slice is worth the effort.

You have probably heard of MailChimp, but what about Benchmark, Moosend, SendinBlue, GetResponse, Mailjet, Pabbly, Constant Contact, MailUp, Zoho, AWeber, Campaigner, Drip, Postcards, Campaign Monitor, or BEE Pro?

Those are just the names from one list; there are at least a dozen more newsletter platforms out there, vying for supremacy of one of the oldest spaces on the net: your inbox.

Of course there are other, more artful platforms engaged in a variation of the same contest. Substack, we all know and love. There is Revue, a Dutch version of Substack, more or less. And somewhere, on life support, lies TinyLetter.

But the one that caught my eye was a bespoke little site called buttondown. Its minimalist aesthetic and decidedly human copy drew me in, and soon I had stumbled down a rabbit hole.

The site was built by a software engineer named Justin Duke, whose personal website mirrors many of the design choices I loved on buttondown: simple, elegant, friendly, unassuming.

Duke works for Stripe, but he has spun off a number of exciting standalone products in his free time, the latest of which is buttondown.

I wanted to know more about why someone would create a niche newsletter platform when so many other alternatives exist, and I was pleasantly surprised to find that my conversation with Duke was one of the most interesting interviews I’ve done for Medialyte.

Duke comes from a writing background — he majored in English, dabbled in journalism, and writes a newsletter himself — but he works full-time in tech.

I have found that people with liberal arts backgrounds who work in tech are often some of the most insightful thinkers, because they bring a flavor of critical theory to their work that often goes untaught in engineering programs. This is no shade on computer engineers — I’m actually parroting what a lot of software designers have told me.

(For a fuller accounting of this phenomenon, check out one of my favorite books of 2020, “Uncanny Valley,” by Anna Wiener.)

Duke had a lot to say about the burgeoning newsletter economy, the paradoxes of the passion economy, and the shortcomings of the Substack revolution. Enjoy the edited interview below, and if you like it make sure to check out buttondown and follow Duke on Twitter.


Name: Justin Duke

Title: Software engineer at Stripe, founder of buttondown

Twitter: @justinmduke

Website: buttondown.email

Personal website: jmduke.com

Could you explain what buttondown is?

Buttondown is a small software tool that lets folks build up a list of email addresses or subscribers and send out emails to them either for free or with a paid component.

It takes away a lot of the burden around creating a newsletter in terms of formatting content, filtering out spammy subscribers, and dealing with a lot of the day-to-day annoyance of curating a large newsletter. 

What motivated you to create it?

I came from using TinyLetter, which — back in 2014, 2015 — you basically chose between TinyLetter and MailChimp, and they had vastly different appeals.

MailChimp was unapologetically a marketing software, used for e-commerce and blasting out enterprise-centric campaigns. TinyLetter was its acoustic alternative, and in the early 2010s it was acquired by MailChimp.

After MailChimp acquired TinyLetter, they basically put it on the back-burner and abandoned it. So if you wanted to write a newsletter and reach a few hundred or thousand subscribers, you really had no good option.

It’s a cliché in the tech world, but one day I said to myself, “I could build a better version of this in a weekend.”

So I tried and it took longer than a weekend, but I got to the point where I was happier using what I built than what was available.

So you were just an OG newsletter fan who felt like the publicly available software sucked. You never thought to yourself, “The newsletter space is the next big thing, I should get in on it”? Because now everyone is talking about newsletters, and buttondown is in the hunt.

I would love to claim that this was all part of some grand strategy, that I could sense where the winds were blowing, but I was neither that wise nor that clever. I just wanted something that I would enjoy using and that I felt could work well for my use-cases. 

You’ve created some other products in the past — Spoonbill, Barback — and now buttondown, but you’re not raising seed money and trying to turn these ideas into businesses or any of that. So what do you get out of it?

For context, I work full-time at Stripe, a payment technology company. I love it very much. I have no real intention of doing the whole startup thing of raising a seed round, burning a bunch of cash to get an audience, securing a Series A, et cetera.

I have no moral judgment against that process, it’s just not what I'm interested in as an engineer. I want to build nice products that I enjoy and maintain them and grow them slowly over time. For me, there's more satisfaction that comes with that approach. 

Frankly, I get much more fulfillment than I imagined from having this weeknights and weekends project become something that thousands of people use every day to send emails.

For instance, my second or third paying customer was a Wisconsin library system that was just trying to send out updates on new, incoming books. A weird part of me gets the warm fuzzies thinking about this hyper-specific use-case and the fact that these people I’ve never met find my product useful.

How does buttondown compare to competitors like Substack? What does it offer that they don’t?

More than focus on competitors, I’m really trying to perfect the writing experience and the technical experience. But I can say that our niche-ness can be an advantage.

One of the advantages of not being a VC-backed operation is that I can limit my market size to just the folks who are interested in a really nice product. When you have a $100 million valuation, part of that mandate involves creating a product that justifies that number.

You have to focus on, “How do I bring in as many people as possible? How do I create a lowest-common-denominator product?” I don’t mean that to sound negative — accessibility is a useful design constraint — but I can do things that focus on highly technical users with a certain subscriber range and really tailor the product to them.

For a guy who built a newsletter platform from scratch, you have tweeted some critiques of email and the newsletter economy. Explain this heresy.

I think it’s very interesting that the newsletter economy has merged with the passion economy, because they’re very disjointed.

If you look at what Substack, Medium, or Patreon are doing, email is almost like an implementation detail. It's not the core focus. The core focus is the patronage-based system, right? You collect a group of followers, convince some of that group to pay you at a regular cadence, and that’s your income. 

The fact that email is involved, as both the delivery mechanism and the identity graph, is actually not that important.

I think a lot of people don't really love emails. If you gave them the choice of subscribing to a dozen newsletters or having an RSS feed on an app that lets you read them all, I think a lot of people would prefer the latter.

I think this new version of the economy, where people strike out on their own and make a living off of their loyal fan base, is here to stay. But I’m not convinced that email is the perfect solution to distribute this content.

So you’re saying that people don’t love newsletters. They just love being able to select the content they want to receive and then not have an algorithm get in the way.

Email is just sort of shitty in a lot of ways. I know this because I've spent so much time working with email and its constraints as a platform over the last few years. A lot of the things that you want from a really rich content or publishing platform, things like the ability to make edits or have discussions or dynamic media, you a priori can't do in email because it's an old and limited platform.

If you look at Patreon or Substack, a lot of the traffic is happening outside the realm of email itself. Like when articles go viral, it's not a 1990s chain email situation; people are spreading it on Twitter or on Reddit or other aggregators.

We haven't quite solved that problem of how to make email either obsolete as a way we distribute and collect information, or how to just make it much, much better. 

Okay weird question: You’re the first Medialyte interview who’s not technically in the media business proper, but you have a writing background, design newsletters, and clearly know a bit about the industry. What are your thoughts on its sorry state of existence?

Two things.

First, these patronage-based companies, whether it's Patreon or Substack or whomever, as they grow larger and larger their interests are going to shift from “How do we get someone from zero patrons to 100 patrons?” to “How do keep the person with 10,000 patrons on the platform?” That could change who they design for and how they construct their business model.

Second, the patronage model allows for one person writing a weekly opinion column to make a good living, but it’s not a meaningful substitute for journalists. What kind of patronage model subsidizes someone doing a months-long investigation?

There’s a reason the industry has developed the way that it has. You have an editing desk because that's how you produce the most rewarding, rich reporting possible.

So you can strike off on your own, write great content, and make tens of thousands of dollars a month, but who is making sure that your arguments are sound? That your data is accurate?

The way we’re heading, jobs that don’t directly have a profit motive will disappear, but they are integral to the quality of journalism.

Rapid Fire

What’s a project of yours that you’re especially proud of?

Buttondown. But also Spoonbill.

What’re you watching right now?

My partner and I always try to watch one gripping show and one smooth-brain show. Right now we’re watching “Watchmen” on HBO and “Degrassi.”

What’re you listening to right now?

It’s embarrassing, but mostly lofi hip-hop beats.

What’re you reading right now?

The Decline and Fall of Practically Everybody,” by Will Cuppy.

What has been your summer highlight?

In a week, my partner and I are adopting a corgi! We’ve been trying to puppy-proof the house for the last week, but I’m sure it’ll still pee on whatever it feels like.


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