Building a Better Tool: Justin Duke's Journey with Buttondown

Building a Better Tool: Justin Duke's Journey with Buttondown
Justin Duke is the founder of Buttondown - a small, elegant tool for producing newsletters.

Tell us about your product and what inspired you to start it?

I was using Tinyletter (a similar tool, still around, owned by Mailchimp) for a long time and was fed up with how it worked. I had the worst possible thought any programmer can have — "can I build a better version of this myself?" — and what started out as a project for a long weekend turned into, well, six years and counting.
(Ironically, when I first started Buttondown my plan was to have it be self-hosted software; I wasn't planning on even shipping the concept of users because I just wanted something I could use and maybe open-source. I didn't convert it into a SaaS until I started tweeting about it and a few friends convinced me!)
Buttondown's now a bit more than what Tinyletter is/was, but the core value proposition of the product is the same — a tool for collecting email addresses and sending emails to those addresses. It also does _way_ more than that — webhooks, Markdown support, a REST API, integrations, tags and metadata, and so on. But the goal was to make a very minimalist tool expressly designed for people like me.

How long did it take you to acquire your first 50 customers, and what was your growth strategy?

It'd be hard to put an exact point and time on it, but certainly longer than I think most people would suspect — probably around eighteen months. There was no overnight success; Buttondown got a decent slew of new users when I launched on Product Hunt and Hacker News but it was definitely a slow burn over time.
My growth strategy was simple: patience is a virtue. I didn't have much marketing spend, in terms of money or energy; I relied on the fact that Buttondown is an inherently social product (every email goes out with a little "powered by Buttondown" footer) and hoped that word-of-mouth would be sufficient. It was! Focusing aggressively on not marketing and hoping that the product's quality would speak for itself worked as I hoped; 5-10% month over month growth in near-perpetuity.

Which technology stack are you using and what challenges and limitations does it pose?

I started Buttondown in 2016 with one piece of technology I was very familiar with (Django deployed on Heroku) and one that I wasn't (Vue). It works....fine, but if I were to start Buttondown from scratch today I would probably have the entire thing be in NextJS. Writing your backend in something that you're really comfortable with is great, and I don't think my reasoning was incorrect, but I have a lot of nits to pick with my current stack:
  • I've had to write a lot of code to keep the frontend and backend in sync. This is a problem that pretty much goes away with more isomorphic approaches like Next.
  • I bet on Vue because I already had a decent amount of experience with React and wanted to try something new. While Vue has grown and matured a lot over the past six years, I straight up do not like it as much as I like React, and at this point it's too late to switch!

What are some of the most essential tools that you use for your business?

I use a lot of the same tools everyone else does, but three I wanted to shout out in particular as being relatively great bang for their buck:
1. DNSHelper , which helps Buttondown's customers sync their DNS settings with Buttondown to send or host on custom domains. Almost every SaaS founder I've talked to who deals with DNS has listed this as a huge pain point and source of operational toil!
2. Logtail for charting + log-spelunking. There are a lot of apps in this space (I've tried almost all of them!), and none seem to have as strong of a value proposition as Logtail.
3. Helpscout is a perfect piece of helpdesk software for folks at my level of traffic + volume, where you've outgrown just having a Gmail inbox but you're not quite at the point where you're managing entire support teams.

What have been some of the biggest insights you've gained since starting your entrepreneurial journey?

The unit economics of "success" and "failure" are drastically different depending on your goals! If you're not spending money on salary, you have a massive advantage over any competitor that does: all you have to do is _survive_ because your burn rate is near-infinite.
Similarly, if your endgame is not a billion-dollar valuation, you can make very surgical and precise decisions to curtail the size of your target audience; these limit the upside of your business, but strengthen your value proposition to the niche that you find.
Lastly, from a product development standpoint, it took me some time to understand how important investing in my own developer experience was. I think there's often a meme in the indie hacker space about "don't write unit tests", "don't use CI" — all this stuff that boils down to "just ship features and build your product base as soon as possible." I think that is true to go from 0 to 1 — there's no point in investing in your codebase if you don't think the codebase actually solves a problem — but as soon as you get to that point where you're confident in the product's longevity you should bias towards spending up-front time to improve your own development cycles.
I would in general recommend aspiring founders to take the vast majority of their time they spend consuming (non-fiction) books, podcasts, and newsletters and instead spend that time in praxis: talking with users, developing and testing software, and thinking critically about what they like and don't like about the products they use.

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