Using Docker for local development on macOS is like putting a shipping container in your garden instead of buying a cupboard from IKEA.
Using Docker for local development on macOS is like putting a shipping container in your garden instead of buying a cupboard from IKEA.
18 December 2025
I’ve been following what Justin Searls has been doing with his blog for some time. He’s been leaning into the “POSSE” (Publish on your Own Site, Syndicate Elsewhere) philosophy more and more. In practice, this looks like building your own version of a single-serving social network on your own site and exposing RSS/Atom feeds to other services to consume. Justin recently released POSSE Party which makes this easier by cross-posting to various social networks. I’ve complained for a while about (anti)social networking so I’m always up for new ways to use social networking less.
I’ve added “thoughts” to my website. If these work correctly, they will be cross-posted to various social networks. Thanks to Justin Searls’ POSSE Party for enabling this.
09 December 2025
The process of software estimation is frustrating for software engineers and those who consume their estimates. Consumers often ask “why can these software engineers not just tell me when it will be done?”.
24 October 2025
In tech, 3 years is often considered a “long tenure”. We maintain open-source projects for 2 years, then burn out. We start habits, lose momentum and quit.
21 October 2025
Interviewed by Software Engineering Daily17 October 2025
Interviewed by Breaking Change - Hotfix podcastAlso available in swear-free/bleeped version on The Changelog and Friends podcast There will be bleeps.
09 October 2025
gem.coop was announced on Monday. As part of that announcement it was mentioned that I was helping gem.coop set up a governance process, continuing the work I’d first started helping with on RubyGems.
07 October 2025
Interviewed by GitHub Podcast29 September 2025
Interviewed by Emanuel Maiberg on 404 Media26 September 2025
When I first joined GitHub in 2013, there was no engineering management. They had people in engineering leadership roles (some with titles, some without) but no dedicated managers to check in with regularly. Initially I thought this was great. Over time, I realised it was actually pretty terrible. As a result, when I started my own company and was a manager for the first time, I wanted to ensure we provided “minimum viable engineering management”. What this meant was providing the necessary support and monitoring infrastructure to ensure great performance while letting managers, present (me) and future, spend most of their time on individual contributions.
24 September 2025
There’s ongoing discussion about recent changes to access in the RubyGems GitHub organisation. If you need context, first read Open Source Turmoil: RubyGems Maintainers Kicked Off GitHub. My goal is to share contribution data to help inform the conversation.
20 August 2025
Interviewed by Noah Bovenizer on The Stack03 June 2025
At the time of writing (June 2025), the prevailing view in the software industry is that LLM-powered AI is either completely useless or will imminently destroy all software engineering jobs. As you might expect, the reality is somewhere in between. In this post, I’ll share my journey with LLM tooling, from reviewing an early, internal alpha of GitHub Copilot to my current daily usage of Cursor, ChatGPT, and the latest Copilot offerings. My perspective is that of a startup founder (of Workbrew) and long-time open source software maintainer (of Homebrew)
22 May 2025
Interviewed by Sage Lazzaro on LeadDev22 May 2025
Interviewed by Open Source Ready Podcast20 May 2025
Interviewed by Open Source Initiative15 April 2025
In the last two years building Workbrew (a remote-first, enterprise Homebrew startup) I’ve hired 5 engineers (and a hybrid PM/EM). This has been my first time being a “hiring manager”. This post explains how I interview and why I do it how I do.
07 April 2025
I left GitHub after 10 years to cofound Raise.dev. After an early failed experiment building IoT developer tools, we pivoted and built Workbrew: an enterprise-friendly layer over Homebrew, a project I’ve maintained since 2009 and led since 2019. Two years in, we’ve raised VC funding, built a remote team, and have happy, paying customers. Here’s what I learned so far.
29 January 2025
Interviewed by Mac Admins Podcast19 November 2024
Interviewed by TechCrunch31 October 2024
Interviewed by Scaling DevToolsAvailable as YouTube video or podcast.
24 October 2024
I've worked on a few Ruby apps in my career at varying scales (Homebrew, AllTrails, GitHub, Workbrew) and there's been a consistent theme: Ruby is great for moving fast (and breaking things).
17 October 2024
Interviewed by The Tech Lounge Podcast