Fifteen years at Apple, demos to Steve Jobs, and a rule for coding with AI: write the spec first. Episode 242 of LinearB's Dev Interrupted podcast, hosted by Andrew Zigler, produced by Free Agent Media for LinearB.
Ken Kocienda spent fifteen years at Apple. He worked on Safari and WebKit, then on the original iPhone, where he built the touchscreen keyboard and autocorrect. Before that he studied history at Yale, taught in Japan, and made fine art photographs. Host Andrew Zigler, who also studied history and taught in Japan, opens with that shared path, and the episode's argument follows from it: the best technology carries the liberal arts into the machine, and the job of the people building it is to make technical literacy not matter.
The middle of the conversation is about building with AI. Kocienda uses AI to code all day and refuses to call it vibe coding. He writes paragraphs of specification, monitors every step, and describes ending the day tired from keeping the model on the narrow path of his intent. Zigler describes the same practice and the two land on a shared conclusion: the specification and exploration documents produced alongside AI-written code are a new kind of artifact that belongs in version control.
Then the Apple years. Kocienda argues that people fixate on the hardware while the magic sits in the software, and tells the story of bringing Steve Jobs mock-ups for a new iPhone system font and being told, in colorful terms, that all of them were junk, followed immediately by the question that mattered: what are we going to do? From that he draws the lesson he carried into everything since: everything is provisional, so plan for change and treat each piece of work as the stepping stone to the next. That is the evolutionary design of Creative Selection, one concrete artifact at a time, keep the good, cut the bad.
The last third is Infactory, the company Kocienda co-founded after Humane. Its premise is extractive rather than generative AI: find the structure hidden in an enterprise's data, surface it with citations back to the source, and let non-specialists build on it. Free Agent Media produced the episode for LinearB's Dev Interrupted, recorded on site at the Engineering Leadership Conference in San Francisco.
“I use AI to code all day, every day. But I don't vibe code. I write very, very detailed specifications. I write paragraphs and paragraphs to the AI, and I monitor everything that it does.”
“People have this real focus on the gadget, but that's not really where the magic is. The magic is in the software.”
“Everything is provisional. Things change very, very quickly, and so we need to plan and account for that kind of change and use the work that we do as the stepping stone for the thing that we do next.”
“It's not about technology. It's very much more about psychology.”
“It has to not matter. There are people out in the world who are experts in what they do. How do we make AI available so they can continue what they're doing, only better? That's the challenge. That's the opportunity.”
“I'll turn around a project in a day and throw it up on a website in an afternoon. But what I'm always most proud of is that spec document that I worked on at the very beginning.”
Podcast production
Free Agent Media produced 1 video for LinearB. Formats: Podcast episode.
Free Agent Media, a video production company for technology companies based in San Francisco, Seattle, and New York, produced episode 242 for LinearB, which publishes the Dev Interrupted podcast. It was released on YouTube and podcast platforms on September 24, 2025.
Dev Interrupted is LinearB's podcast for software engineering leaders, hosted by Andrew Zigler, Ben Lloyd Pearson, and Dan Lines. This episode is hosted by Andrew Zigler.
Ken Kocienda is co-founder and CTO of Infactory and the author of Creative Selection. He spent fifteen years at Apple as a Principal Engineer, where he worked on Safari and WebKit and created the iPhone's touchscreen keyboard and autocorrect.
On site at the Engineering Leadership Conference in San Francisco, in the Dev Interrupted recording set the show brings to conferences.
Kocienda's path from a history degree to Apple, why the liberal arts belong in technology, his spec-driven approach to coding with AI, demoing to Steve Jobs and the lesson that everything is provisional, evolutionary design from Creative Selection, what autocorrect taught him about intent and remediation, and Infactory's extractive AI approach to enterprise data.
The full-length video episode, 31 minutes and 28 seconds, published on the Dev Interrupted YouTube channel.
