Kris Puckett - Becoming an AI-native designer

2026-03-19 - 53 min - source - Read full transcript

Rid (host)Kris Puckett

Key insights

The phrase 'I don't know' is the most productive way to start with Claude Code, and momentum comes from small, visible wins rather than up-front planning.

Kris says he used to self-limit his creative work waiting for permission or a fully fleshed-out plan. Saying 'I don't know how to do this, you literally just need to connect this service somehow' prompted Claude to walk him step by step through his first-ever API integration (Google Books, for Epilogue's covers), and seeing it show up on screen ('I'm doing stuff') became his main source of momentum.

permissionless-building

Claude Code works best as a co-creator, not just an executor of pixel-perfect specs.

Kris says Claude would sometimes produce UI he wouldn't have designed himself on a canvas, but he liked the initial direction and reshaped it until it matched his vision. He never used a canvas tool for Epilogue's layouts - he gave hierarchy and feedback until the result felt authentically his.

claude-code-as-creative-partner

You can teach Claude Code an unfamiliar technical domain by compiling scattered source material into a custom skill.

To build Metal-shader effects for Epilogue's book covers, Kris fed a YouTube intro-to-shaders video and content from The Book of Shaders into a research agent that summarized the material into a skill, effectively teaching Claude Code a subject neither of them started out understanding.

skills-and-personal-automation

LLM output should be actively distrusted and checked, not accepted at face value.

Kris says LLMs 'are going to hallucinate like crazy' and routinely asks Claude to grade its own plan and confirm whether it pulled from accurate sources, treating verification as a constant habit rather than a one-time step.

claude-code-as-creative-partner

Skills are just markdown instruction files, and Claude Code's built-in skill-creator removes the need to know how to write one.

Kris explains that telling Claude Code 'I want to make a skill' triggers a guided flow: it asks what you want the skill to do, drafts a plan, produces the skill, and can even grade its own output and revise it to a higher standard - all without the user writing markdown by hand.

skills-and-personal-automation

The best onboarding for someone with no AI workflow is Claude Code's ask-question mode, not a canvas tool like Lovable.

In a role-play with Rid, Kris recommends telling Claude Code who you are and what you do and asking it to figure out where it can help - it will surface a few ideas that 'switch something on your brain,' which changes how you work with the tool faster than jumping straight to a visual builder.

skills-and-personal-automation

LLMs don't do spontaneous creative divergence well, but they can be explicitly taught structured ideation exercises.

Kris says the classic design-sprint 'crazy eights' technique (rapid sketched variations from one idea) isn't something LLMs do natively, but you can teach a model to perform that divergent-thinking pattern if you communicate the intent clearly.

claude-code-as-creative-partner

Personal AI automation is expanding beyond the desktop terminal into ambient, always-available assistants.

Kris built an iOS app in two hours to sync Apple Health data between separated iCloud accounts to his home Mac mini, and uses a remote assistant he calls 'Shadowfax' via iMessage/Telegram to capture ideas on walks and turn them into Linear tickets worked on by a separate local Claude instance.

skills-and-personal-automation

A generic portfolio template is now a red flag to hiring managers, given how little time they spend per review.

Kris says reviewers may look at a portfolio for only 6-10 seconds, and a basic Squarespace or Webflow template signals a candidate isn't using tools like Claude Code, ChatGPT, or Gemini to build something more custom - even if the underlying work is strong.

ai-in-hiring-and-portfolios

Demonstrating curiosity in hiring now means showing evidence of actually building with AI, not just claiming to be curious.

Rid notes hiring managers repeatedly cite 'curiosity' as the top trait they look for but struggle to define what it looks like in practice; Kris argues showing a self-built project, skill, or process - even something only tangentially related to design - is what actually demonstrates it.

ai-in-hiring-and-portfolios

As AI commoditizes technical craft, personal authenticity becomes the real differentiator.

Kris predicts 'soul' will become the word of the year because craft and quality are increasingly table stakes; he compares the moment to the MySpace era, where a fully custom personal page was a genuine expression of identity, and argues portfolios should feel like the person, not a template.

authenticity-and-soul-in-ai-design

Autonomous, permission-skipping agent use conflicts with wanting output to feel authentically yours.

Kris says he dislikes letting agents run unsupervised for hours ('dangerously skip permissions') because it produces a mentality of just accepting whatever output comes back, similar to how AI-written Twitter articles start to sound the same; he prefers staying in the loop and giving feedback until work feels like his own.

authenticity-and-soul-in-ai-design

Books referenced

The Odyssey - Homer - used as Kris's example when explaining how Epilogue's book-search filters through Google Books API results to find a specific cover

Media referenced

The Book of Shaders - other - online reference Kris fed to Claude Code, alongside a YouTube intro-to-Metal-shaders video, to build a custom skill teaching Claude how Metal shaders work

Companies

Stripe - Kris's current employer, where he leads design
Dropbox - past design role for Kris
Mercury - past design role for Kris
Perplexity - tool Kris used pre-Claude Code to create per-book 'spaces' for reading notes, which sparked the idea for Epilogue
Anthropic - maker of Claude Code and the Skills format Kris builds his personal automations on
Cursor - Kris's first attempt at building his book app; he hit walls because it wasn't built for iOS development at the time
Google Books API - data source Kris connected Epilogue to for pulling book covers and metadata
Apple - source of the Foundation Models framework (on-device LLMs) and iOS 26 liquid glass patterns Kris built Epilogue's UI around
Linear - project-tracking tool Kris has Claude Code populate with auto-generated tickets from his brain dumps, then works through each morning
Jitter - sponsor; image-to-video tool mentioned in the episode's ad read
Paper - sponsor; connected canvas tool Rid describes using alongside Claude Code for exploring design variations
Inflight - sponsor; Rid's own feedback tool for sharing prototypes and collecting structured feedback
Vercel - hosting option Kris says Claude Code can spin up a free site on in about an hour
Squarespace - cited as the kind of generic template that now signals a candidate isn't using AI tools to differentiate their portfolio
Webflow - cited alongside Squarespace as a generic template choice hiring managers now read as a red flag
Framer - part of Rid's closing product stack list, used for building websites
Granola - part of Rid's closing product stack list, used for note-taking during design crit
Lovable - cited as the role-play designer's starting point (a pattern generator) and part of Rid's closing product stack, used for building ideas in code
Mobbin - part of Rid's closing product stack list, used for design inspiration
Raycast - part of Rid's closing product stack list, described as Kris's shortcut every step of the way

Techniques and frameworks

Permissionless building - Kris's core theme: you don't need a fleshed-out plan or approval to start building with Claude Code, just start typing 'I don't know'
Claude Code Skills - markdown instruction files that teach Claude repeatable patterns (e.g. a liquid-glass skill, a Metal-shader skill); Claude Code has a built-in skill-creator that drafts, self-grades, and refines skills
Claude Code loops (/loop) - recurring prompts run on an interval, e.g. Kris's morning prompt reviewing his HRV and health metrics
Parametric design via Metal shaders - Kris extracts book-cover colors with Color Cube, generates a mesh gradient, applies a Metal shader on top, and tunes exposed parameters (color temperature, origin) before hard-coding final values
Ask-me-questions onboarding - Claude Code's built-in ask-question tool interviews the user about who they are and what they do, then surfaces personalized ways it could help - Kris's recommended first step for anyone with no AI workflow yet
Crazy eights taught to an LLM - the classic design-sprint divergent-thinking exercise (quick sketched variations), which Kris says LLMs don't do natively but can be explicitly taught to perform
Self-grading / hallucination checks - Kris routinely asks Claude to grade its own plan and confirm whether it hallucinated or pulled from accurate sources before trusting output

Summary

Kris Puckett, who has led design at Dropbox and Mercury and now leads design at Stripe, joins Dive Club host Rid to walk through how building a personal iOS app, Epilogue, changed his relationship with AI tools and his day-job practice. Epilogue started as a long-deferred dream: Kris wanted to make his own software since getting his first iBook G4 in 2005 but never got past the coding barrier, despite repeated attempts with Treehouse and Swift courses. The breakthrough came when Claude Code let him build a private reading-notes app - solving a problem Perplexity's "spaces" feature almost but didn't solve - without him needing to become a traditional engineer first.

The through-line of the conversation is what Kris calls permissionless building: the realization that "I don't know" is a superpower rather than a stopping point. He describes getting Epilogue's Google Books API integration working, having Claude Code walk him through creating and securing an API key, and how that visible progress fueled momentum. He extends this into building a custom Metal-shader skill by feeding Claude a shader tutorial video and content from The Book of Shaders, teaching it a subject he himself didn't understand, then iterating on exposed parameters until the mesh-gradient shader effect on Epilogue's book covers looked right.

Kris is explicit that he doesn't trust LLM output blindly - he regularly asks Claude to grade its own plans and check for hallucinations - and that Claude Code functions best as a co-creator he stays deeply in the loop with, rather than an autonomous executor. He contrasts this with "dangerously skip permissions" agent workflows he avoids, arguing that letting agents run unsupervised for hours produces generic, un-authored output, the same failure mode he sees in interchangeable AI-written Twitter articles.

The conversation broadens into Kris's personal automation stack: Claude Code Skills (markdown instruction files with a built-in skill-creator that drafts and self-grades its own work), the /loop feature for recurring prompts like a morning health-metrics review, and an ambient assistant he calls "Shadowfax" that he talks to via iMessage and Telegram to capture ideas on walks and convert them into Linear tickets. He also built a small iOS app in two hours to bridge Apple Health data between separated iCloud accounts to his home Mac mini, illustrating how far "I don't know, can you fix it?" can take someone with no prior engineering background.

Closing on hiring, Kris argues the bar for designers has risen: a portfolio built on a generic Squarespace or Webflow template now signals a candidate isn't using AI tools to differentiate themselves, given how little time (6-10 seconds, he estimates) reviewers spend per portfolio. He pushes back gently on "curiosity" as hiring-manager shorthand, arguing what actually demonstrates it is visible evidence of having built and iterated with these tools. He closes by predicting "soul" will become the design word of the year - as craft and quality get commoditized by AI, personal authenticity, the same instinct that made MySpace pages feel handmade, becomes what differentiates a designer's work.

Notable Quotes

"I don't know is actually a superpower." - Kris Puckett

"Soul is going to be one of those things that is like the word of the year, this year and next year." - Kris Puckett

"Beware the barrenness of a busy life." - Kris Puckett, quoting Plato

"That blinking carrot is this invitation for you to just tell it: I don't know. I don't have any idea how you work. Here's how I work. What can we do together?" - Kris Puckett