Portfolio

Projects & Passions

A collection of software, products, and creative work. From open-source tools to companies that taught thousands to code.

Rethink Everything
Writing Launched Featured

Rethink Everything

Ten essays on what I've changed my mind about since agents started writing my code

Almost every best practice I taught was an optimization for the human programmer. The human isn't the one writing the code anymore, so I'm rethinking all of it: DRY, the testing pyramid, rewrites, microservices, types, native apps, and who we optimize code for.

2026 View Project →
Clever Cat Prep
App Live Featured

Clever Cat Prep

CCAT practice with an AI coach

A CCAT practice app I built for my nephew in less than a day. Timed drills, a skip map, an AI coach that reads your own attempts, and a voice mode for practicing in the car.

Cloudflare Workers D1 React Router Hono +2
2026 View Project →
Climbing Movies
Website Launched Featured

Climbing Movies

My favorite rock climbing movies

Climbing Movies is a hand-curated library of climbing films that are legitimately free to watch online. Every film is embedded from the channel that made it, whether that is Reel Rock, Patagonia, Mellow, Louder Than Eleven, or a climber's own upload, and every page links back to the source. There are no accounts, no fees and no ads. Browse by discipline, climber, country, crag, filmmaker, or start with a curated list. Each film has a short writeup that says what it actually is, so you know whether you are getting a 6 minute ascent film or an hour long documentary before you press play.

2026 View Project →
PromptEngine
Code Launched Featured

PromptEngine

Manage AI prompts at scale

Open-source Rails engine for managing AI prompts at scale. Version control, A/B testing, and composable workflows built in.

Rails Ruby PostgreSQL Hotwire +1
2024 View Project →
Homebaum
Chrome Extension Launched Featured

Homebaum

Every new tab is a trap. Take back your browser time

A chrome extension that replaces your new tab with a Zen focus tab with your top priorities for the day.

2025 View Project →
VCMatch.ai
App Launching Featured

VCMatch.ai

AI-powered investor matching

Upload a pitch deck, get matched with VCs whose thesis aligns with your startup in 30 seconds.

Rails OpenAI Pinecone PostgreSQL +1
2026 View Project →
ActionVersionPreview
Rails Engine Launched Featured

ActionVersionPreview

Preview design iterations in Rails

Preview multiple versions of your Rails views simultaneously. No feature flags, no database, no configuration. Just file names and URLs.

2025 View Project →
Railspress
Rails Engine Beta Featured

Railspress

Content management the Rails way.

A Rails engine for blogging and content. Rich text editing, SEO metadata, categories, and tags out of the box. Plus an Entity System to manage any model with a simple DSL.

2025 View Project →
Socratic Tutor
Code Launched Featured

Socratic Tutor

AI that teaches through questions

AI that teaches through questions, never gives answers. Adapts to frustration levels and learning styles in real-time.

Rails Claude Hotwire PostgreSQL +1
2024 View Project →
Slaps.video
App Launched Featured

Slaps.video

Find the video that slaps

A parlor game for finding the best video.

2024 View Project →
shadcn-rails
Rails Engine Launched Featured

shadcn-rails

A port off shadcn/ui to rails

Beautifully designed components based on shadcn/ui that you can copy and paste into your apps. Accessible. Customizable. Open Source. Now for Rails

2023 View Project →
MatchMaker.chat
Prototype Live Featured

MatchMaker.chat

Online dating in an AI age.

No profile. No chat. Just dates.

2025 View Project →
JustFuckingStopAlready
Site Launched Featured

JustFuckingStopAlready

Just fucking stop telling devs what to use.

A meme site.

2025 View Project →
Kode With Klossy
Non Profit Launched Featured

Kode With Klossy

Free coding camps for young women

Co-founded with Karlie Kloss to provide free coding education to young women and underrepresented groups.

Education Web Development Community Curriculum Design
2015 View Project →
Miki Beach
Community Launched

Miki Beach

My burning camp and family.

From the second I dropped into my first burn in 2016 I knew Miki Beach was home.

View Project →
Faraday Ventures
Investments Live

Faraday Ventures

Angel investing to make connections.

I occasionally invest in founders I believe in.

2019 View Project →
Designer Pages
Company Exited

Designer Pages

My first startup.

A search engine and product management suite for architects and interior designers. The standard spec'ing tool of the industry.

2007 View Project →
JobBoard App
App Live

JobBoard App

A job board app in rails

A standalone rails app for hosting your own job board.

2023 View Project →
Tech Event Bingo
Game Launched

Tech Event Bingo

Your bingo card for everything tech is about to do.

Twenty-four things that might happen this year. Half will. The other half really shouldn't. Add your handle and the card is yours to post.

2026 View Project →
Learn.co
App Launched

Learn.co

Online learning that worked.

Built the learning management system that pioneered browser-based coding environments, later inspiring GitHub Codespaces.

Rails React Docker PostgreSQL +2
2014-2020 View Project →
Flatiron School
Creative Launched

Flatiron School

Learn to code. Change your life.

Founded and built one of the first coding bootcamps, teaching 10,000+ students to become software developers.

Education Curriculum Design EdTech Ruby on Rails
2012-2020 View Project →
Poker Outs
App Launched

Poker Outs

Know when to get out.

A PWA for calculating your outs in poker.

2025 View Project →