Cassidy Williams is a software engineer and developer advocate by profession who loves teaching people coding skills (and making them laugh with dumb jokes)! She's currently the CTO of a small AI startup called Contenda, and has worked at a bunch of other companies, large and small — almost always focusing on how to make developers build better.

Cassidy's been a true Buttondown O.G. — she's been sending newsletters for almost five years through the platform, and we caught up with her to learn more about her process and how she uses Buttondown.

It's a joy to write and I love it when people say that they've learned something from it!

Tell me a little bit about your newsletter! What do you write about?

My newsletter is a little bit of tech news, a little bit of what I'm up to, a little bit of technical interview practice, and a little bit of fun non-tech things too, every week. It's a joy to write and I love it when people say that they've learned something from it!

Where do you find all the content for every week's newsletter? Especially with technical interview questions — I imagine it's kind of hard to just randomly stumble upon dynamic programming problems on Twitter or wherever!

I am very online, heh. I'm in a bunch of Discord groups where folks promote articles they write, plus I subscribe to a bunch of different blogs (both tech-related and not) that I pull content from, plus I "harvest" links from Reddit, Hacker News, Twitter, and a few other spots where things pop up. As for the interview question... that really varies. I try to pull those from actual technical interviews (I'm in some groups where people share their interview experiences), and try to do variations of questions you see on sites like LeetCode and HackerRank! :

You've been rendezvous-ing (is that a word?) for over five years now. How has your process changed over time?

Oh man, I am just a lot more focused on my workflows now, more than anything! I now have templates that I use to populate the newsletter, I have scripts that I run that renders all of the people answering interview questions, I have a dedicated bookmark tool for the newsletter... all of that has made a big difference over time!

When did you start building out these automations? At what point did it make more sense to lean on scripting vs. doing it manually every time?

I started building some of my automations once I had enough responses to my newsletter that I couldn't keep up manually. The interview question of the week in particular was tough to keep track of after a while (because people send in their answers on Twitter, by responding to the email, on Discord, and a few other spots), where in the first year or so I'd only get a couple responses here and there, but now I consistently get between 10 and 30 responses each week!

Where did you first learn of Buttondown, and what made you decide to give it a try?

I first learned about it from a friend, Iheanyi Ekechukwu! He recommended it so highly when I mentioned that I was starting to outgrow TinyLetter. Once I tried it, the fact that I could keep writing markdown and import all of my subscribers sold me right away, and the service has only gotten better since then!

It's one of those services that "disappears" because it works so smoothly, I don't have to think about it!

What are some ways Buttondown has helped you run/manage RwC?

First of all, the customer service has been awesome. Justin is always so quick to fix issues and answer questions, I know I'd not get better service anywhere else! And secondly, I love that I can easily check on deliverability for individual subscribers, and check out analytics at a quick glance. I really don't have any complaints. It's one of those services that "disappears" because it works so smoothly, I don't have to think about it!

What are some things you’d be excited to see Buttondown build in the next few months?

I genuinely can't think of anything (I looked through the roadmap and it all looks good), maybe a referral system? That'd be sick.

If you were restarting your newsletter now, from zero subscribers, but knowing everything you've learned over the past five years — what would you do differently?

I'd build out more automations early for populating and authoring quickly, and maybe make things a little shorter. There's some parts of my newsletter that are still fairly manual because I established it that way very early on, and I don't mind that, but if I were starting again, I'd definitely plan that better.