Announcing PWV Fund I 22 Oct 2025 - Bay Area, CA New achievement! Preston-Werner Ventures (through which I did my angel investing) has become PWV ™ and I’m raising a venture fund targeting $100M to lead pre-seed and seed rounds in today’s most exciting software- and AI-driven companies. Over the past thirteen years, I’ve invested in over 175 amazing startups, including some of the earliest checks…
RedwoodJS’ Next Epoch: All In on React Server Components 30 May 2023 - Bay Area, CA RedwoodJS is the full-stack JS/TS web framework designed to help you grow from side project to startup. For the last year, the RedwoodJS team has been prototyping solutions to the framework’s lack of a proper server-side rendering (SSR) feature. Today, I’m happy to announce that we have chosen to implement a modern…
Major Version Numbers are Not Sacred 23 May 2022 - Positano, Italy Ten years ago, I sat down and wrote the first version of what became the Semantic Versioning (SemVer) spec. I was tired of everyone using version numbers in whatever way they wanted and knew we could do better if we all agreed on what each part of a version number meant and how those numbers should change as the project’s code…
Introducing the Redwood Startup Fund 7 Apr 2022 - Bay Area, CA Today I’m pleased to announce the Redwood Startup Fund: a $1M fund that will invest $25k–$50k in startups that use RedwoodJS as a primary component in their stack. I have several goals in mind with this fund: Help more startups explore more territory, more quickly. This is our mission at RedwoodJS. Until now we’ve provided software,…
Announcing RedwoodJS 1.0 and $1M Funding 4 Apr 2022 - Bay Area, CA Three years ago, I had an idea for a new web app framework. Two years ago, we released RedwoodJS v0.1 to the world. Today, more than 300 talented individuals have lent their ideas and time in crafting our documentation, design, community, marketing, and code. During the journey, we found our mission: to help more startups explore…
Committing $250k this Year to Racial Justice Efforts 15 June 2020 - San Francisco On February 23rd, Ahmaud Arbery was murdered by armed white men while jogging near Brunswick, Georgia. On March 13th, Breonna Taylor was murdered by Louisville Metro Police in her own home. On May 25th, George Floyd was murdered by Minneapolis Police officers. These are just three of the names on the list of…
We Are Giving $1M Toward San Francisco COVID-19 Response 23 Mar 2020 - San Francisco COVID-19 represents an unprecedented threat to the health and livelihood of people everywhere, and as we wait for the the US government to act on this emergency, my wife, Theresa, and I have decided to put one million dollars toward our local community’s efforts to prepare for and mitigate the effects of the…
Joining the Netlify Board to Help Shape the Future of the JAMstack 4 Mar 2020 - Cordon, France In late September, 2015, I got an email out of the blue from Mathias Biilmann . He told me about his brand new 2-person startup called Netlify and asked if I’d fancy getting together to chat about it. You see, they were making it really easy to deploy static sites like Jekyll and thought I might be…
Snyk - Automatically Scan and Fix Ruby and Nodejs Vulnerabilities 10 Nov 2016 - San Francisco This is a story about a company called Snyk (pronounced “sneak”), their founder Guy Podjarny, my decision to become one of their advisors, and how they are going to help save you from malevolent agents trying to steal your digital stuff. If you’re anything like me, you’re simultaneously terrified and in…
Replicated - An Easier Path from SaaS to Enterprise 19 Jun 2015 - San Francisco Over the last year I’ve had a chance to learn a lot more about early stage funding and made angel investments in a handful of startups. So far I’ve restricted my involvement to companies with ideas in which I have significant domain knowledge. I also insist on founders with relentless product focus, a fierce desire to…
Farewell GitHub, Hello Immersive Computing 21 Apr 2014 - New York City Today is my last day at GitHub. Recent events have given me a lot of time to reflect on what’s important to me, and I’ve decided to switch gears and focus on building something from scratch again. Since visiting the Oculus VR team at their office three months ago, I’ve come to believe that immersive computing (aka virtual…
Open Source (Almost) Everything 22 Nov 2011 - San Francisco When Chris and I first started working on GitHub in late 2007, we split the work into two parts. Chris worked on the Rails app and I worked on Grit, the first ever Git bindings for Ruby. After six months of development, Grit had become complete enough to power GitHub during our public launch of the site and we were faced with an…
Rejected Bio from The Setup 03 May 2011 - San Francisco Yesterday, the autobiographical post I wrote for The Setup went live. I wrote that post over a year ago and then entered into an epic battle with @waferbaby about the length of my “Who are you, and what do you do?” section. He said it was too long. I said it could not be shortened. And so the post sat for a year, collecting dust, neither of…
Ten Lessons from GitHub’s First Year 29 Mar 2011 / 29 Dec 2008 - San Francisco This post was written in late December of 2008, more than two years ago. It has stayed in my drafts folder since then, waiting for the last 2% to be written. Why I never published it is beyond my reckoning, but it serves as a great reminder of how I perceived the world back then. In the time since I wrote this we've…
Designer, Architect, Developer 11 Dec 2010 - San Francisco Over the last six years I’ve bootstrapped three successful enterprises (Cube6 Media, Gravatar, and GitHub) and failed to gain traction with a handful of others. After a lot of thought and reflections on these experiences, I’ve identified three major skills that should be present in order to best build a successful web application. These…
Optimize for Happiness 18 October 2010 - San Francisco Two days ago I had the pleasure of speaking at Startup School, a yearly conference on entrepreneurism put on by the great folks at Y Combinator. Never before have I see such a high concentration of smart ambitious people in one place. You can watch the recording of my thirty minute slot on Youtube: Since I only had about 25 minutes for the…
Readme Driven Development 23 August 2010 - San Francisco I hear a lot of talk these days about TDD and BDD and Extreme Programming and SCRUM and stand up meetings and all kinds of methodologies and techniques for developing better software, but it’s all irrelevant unless the software we’re building meets the needs of those that are using it. Let me put that another way. A perfect implementation of…
TomDoc - Reasonable Ruby Documentation 11 May 2016 - San Francisco RDoc is an abomination. It’s ugly to read in plain text, requires the use of the inane :nodoc: tag to prevent private method documentation from showing up in final rendering, and does nothing to encourage complete or unambiguous documentation of classes, methods, or parameters. YARD is much better but goes too far in the other…
The Git Parable 19 May 2009 - San Francisco Git is a simple, but extremely powerful system. Most people try to teach Git by demonstrating a few dozen commands and then yelling “tadaaaaa.” I believe this method is flawed. Such a treatment may leave you with the ability to use Git to perform simple tasks, but the Git commands will still feel like magical incantations. Doing anything out of the…
Blogging Like a Hacker 17 Nov 2008 - San Francisco Back in 2000, when I thought I was going to be a professional writer, I spent hours a day on LiveJournal doing writing practice with other aspiring poets and authors. Since then I’ve blogged at three different domains about web standards, print design, photography, Flash, illustration, information architecture, ColdFusion, package management, PHP,…
How to Meet Your Next Cofounder 3 Nov 2008 - San Francisco Over the last few months I’ve seen a number of people looking for cofounders on Hacker News or via their own personal blogs. I think this is, at best, a highly inefficient way to find a cofounder and, at worst, a way to fool yourself into finding the wrong cofounder. In any case, it’s a naive approach to finding the person that will need…
Looking back on Selling Gravatar to Automattic 23 Oct 2008 - San Francisco For an entrepreneur, the line between horrible mistake and runaway success can be so thin that even Kate Moss would be envious. I lived with Gravatar for nearly four years before that line even became thick enough to measure. As it’s become one of my favorite parables, I’ll save the details of how I came up with the idea…
How I Turned Down $300,000 from Microsoft to go Full-Time on GitHub 18 Oct 2008 - San Francisco 2008 is a leap year. That means that three hundred and sixty six days ago, almost to the minute, I was sitting alone in a booth at Zeke’s Sports Bar and Grill on 3rd Street in San Francisco. I wouldn’t normally hang out at a sports bar, let alone a sports bar in SOMA, but back then Thursday was “I Can…