The Hallway Track: Why AI Rewards People Who Already Have Taste
I joined Chris on The Hallway Track to talk about running Box Out Sports, Fireside, and Flipper while still maintaining open source projects like HTTParty.
We covered a lot of ground in 50 minutes: why I gave up trying to focus, the production problem that led to Flipper, how feature flags change the way teams build software, and why taste might be the real advantage in the AI era.
Some of the highlights:
Giving Up on Focus. I spent years feeling like I was broken because I couldn’t focus on one thing. Everyone tells you focus is how you do something big and great, but I like having a lot of things going. If I get jammed on one project, I can switch to the next most important thing on another instead of dropping to zero. I don’t push one thing forward as far or as fast, but I push a lot of things forward regularly. I finally gave up trying to be someone else about three years ago.
What AI Changed at Box Out. The biggest change is amplification. We have shipped so much in the last six months. But we’re also doing things we would have just said no to before. For years Box Out was built for speed, not customization. Recreating Photoshop in the browser was way outside our niche and not worth the time. Now we’re building a Figma or Photoshop-style template editor because, well, what if we did both?
The Scaling Crisis That Led to Flipper. While working on Words With Friends, we were having scaling problems because a bunch of celebrities started playing and traffic went nuts. I kept rolling out a new caching system and taking down the site because the cache was cold. Then we tried a percentage rollout. I went from 1% to 5% until the cache was warm enough and then let it rip. Feature flags were amazing, but the library we used only supported Redis. I built Flipper so your flags could live in Active Record, environment variables, a file on disk, or whatever made sense for your application.
Feature Flags Change How You Build. Technically a flag is just a quick check to see if something is on or off. But once people start using them, you have to pry them out of their cold dead fingers. You can get unfinished work into production, let the right people try it, and turn it off without another deploy. Everything gets easier, less stressful, and less scary. Chris shared an old newspaper phrase I loved: “demos over memos.” Just get something on a screen that people can react to. If it’s behind a flag, who cares? Nobody sees it. You didn’t break anything. It’s fine.
Maintaining Open Source With AI. I get much better pull requests for HTTParty now. They show up with tests and are often pretty close to ready to ship. AI also helps me research what to work on next and triage security reports. Half the time I read one of those reports and think, bro, I don’t even know what language this is. Now I can understand it, figure out if it’s real, and release CVE fixes faster. That makes a huge difference for a project I maintain in my spare time.
Taste Is the Advantage. Everyone I see exploding with AI already had taste and ideas. They were good without it. They were just constrained by time, brainstorming, research, and all the other stuff around creating a product. AI amplifies that by a different multiplier. It also amplifies bad taste and lets dysfunctional teams make a mess ten times faster. The building was never the hard part. Figuring out what to build was.
Building Games With My Son. We started with AI-generated coloring pages and bedtime stories. Then we made Chickens vs. Zombies, where chickens shoot eggs out of their butts to kill zombies. Obviously. From there we built a Minecraft-ish game with 3D worlds, chat, portals, and Cloudflare Durable Objects. Neither of us had ever made a game. Now he can build what’s in his imagination, play it with his friends, and learn the same things I do when I build software: ask questions, prove that it works, and keep making it better. He used to say he wanted to be an inventor. Now he says he’s going to be a programmer.
We also got into turning open source into a business, the future of runtime controls in Flipper, why AI exposes dysfunction inside engineering teams, and what programming may look like for the next generation.
Watch the full conversation on YouTube. I hope you enjoy it.