How I AI

Claire breaks down the biggest announcements from Anthropic’s “Code with Claude” event and what they actually mean for builders shipping AI products today. From scheduled AI routines to outcome-based agents, multi-agent orchestration, and new memory systems, Claire walks through the features she’s most excited to use immediately—and how they could reshape the future of agentic software.

What you’ll learn:
How Claude Code routines let you automate recurring workflows on schedules or webhooks
What “Outcomes” are and how rubric-based agent grading works
How multi-agent orchestration enables specialized AI teams with different roles and tools
Why Anthropic’s new “Dreams” memory system matters for long-term agent behavior
Why increased Claude Code usage limits are a bigger deal than they sound
How Claire thinks about building practical agentic products today
—
Resources:
• Code with Claude: https://claude.com/code-with-claude
• Claude Code Routines Docs: https://code.claude.com/docs/en/routines
• Define Outcomes Docs: https://platform.claude.com/docs/en/managed-agents/define-outcomes
• Dreams Docs: https://platform.claude.com/docs/en/managed-agents/dreams
• Multi-Agent Docs: https://platform.claude.com/docs/en/managed-agents/multi-agent
• Managed Agent Webhooks Docs: https://platform.claude.com/docs/en/managed-agents/webhooks#supported-event-types
• Codex (OpenAI): https://openai.com/codex
• GitHub: https://github.com
—
Where to find Claire Vo:
ChatPRD: https://www.chatprd.ai/
Website: https://clairevo.com/
LinkedIn: https://www.linkedin.com/in/clairevo/
X: https://x.com/clairevo
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

John Kim is the co-founder and CEO of Delight.ai, a customer experience platform that’s transforming how companies deploy AI. But what makes John’s story fascinating isn’t just his product; it’s how he’s turned his entire company into an AI-native organization. His marketing team built a fully functional e-commerce swag store with Stripe integration in days. His sales team built their own CRM tools. His recruiting team automated their entire workflow. And it’s all tracked, measured, and celebrated through an internal platform called Automators.

What you’ll learn:
How Sendbird’s marketing team built a fully functional swag store with Stripe integration in a day (with no engineering support)
How the Automators platform works—an internal marketplace where anyone can request AI tools and engineers (or AI agents) can build them
How to create secure, compliant templates so non-technical teams can ship to production safely
How Sendbird built a token usage dashboard with five tiers (beginner through AI God) and why tracking the smoothness of the curve matters more than the total
Why visible leadership usage is the most powerful adoption signal
Why Sendbird rewrote job descriptions to prioritize curiosity, agency, and energy over years of experience
How John uses AI for his own learning
—
Brought to you by:
WorkOS—Make your app enterprise-ready today
ThoughtSpot—Build AI-powered analytics into your product
—
In this episode, we cover:
(00:00) Introduction to John Kim
(02:45) The Delight.ai swag store built by marketing in two days
(05:51) The before times: when fun had to earn its place on the roadmap
(07:55) Demo: The Automators platform and quest system
(13:47) The AI Engineer for Internal Operations role
(16:06) Demo: The company-wide skills marketplace
(17:19) Treating AI adoption as a product
(18:43) Real wins: team-level and campaign examples
(21:51) Why SaaS isn’t dead—it’s being rebuilt internally
(23:46) Demo: The token tracking dashboard
(26:32) Measuring without fear: setting expectations, not punishments
(28:54) Quick recap
(30:51) Personal AI use cases: endless knowledge at your fingertips
(36:15) Lightning round and final thoughts
—
Tools referenced:
• Claude Code: https://claude.ai/code
• Codex (OpenAI): https://openai.com/codex
• Obsidian: https://obsidian.md
• GitHub: https://github.com
• Stripe: https://stripe.com
—
Other references:
• Jason Levin (CEO of Memelord) on How I AI: https://www.lennysnewsletter.com/p/from-a-690-newsletter-to-3m-api-how
• Konami Code: https://en.wikipedia.org/wiki/Konami_Code
• Andrew Huberman’s podcast: https://hubermanlab.com/
• Y Combinator: https://www.ycombinator.com/
—
Where to find John Kim:
X: https://x.com/doshkim
Instagram: https://instagram.com/dosh
LinkedIn: https://www.linkedin.com/in/doshkim/
Company: https://delight.ai
Delight.ai Spark Conference (May 7, SF): https://delight.ai/spark
—
Where to find Claire Vo:
ChatPRD: https://www.chatprd.ai/
Website: https://clairevo.com/
LinkedIn: https://www.linkedin.com/in/clairevo/
X: https://x.com/clairevo
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

Owen Williams is a design manager at Stripe who built Protodash, an internal AI-powered prototyping platform that lets designers and PMs create high-quality Stripe dashboard prototypes without writing code. What started as a bundle of Cursor rules and React components evolved into a full web-based prototyping studio that runs in dev boxes, complete with design review modes, variant testing, and AI-powered iteration. Surprisingly, PMs now use Protodash just as much as designers, fundamentally changing how Stripe approaches prototyping, design reviews, and engineering handoffs.

What you’ll learn:
How Stripe built an internal AI prototyping tool using Cursor rules, MCPs, and their design system
Why “blurple slop” happens when designers use generic AI tools—and how to fix it
The architecture behind Protodash: React router, design system components, and MCP integrations
How Stripe prototypes in dev boxes so designers never have to worry about local setup
Why “demos, not memos” transformed Stripe’s design review culture
How Stripe built design review modes, variant testing, and AI annotation directly into your prototyping tool
Why internal tools don’t need to be production-grade to be transformative
—
Brought to you by:
Celigo—Intelligent automation built for AI
Cursor—The best way to code with AI
—
In this episode, we cover:
(00:00) Welcome and intro to Owen Williams
(02:19) The “blurple slop” problem with AI design tools
(03:50) Protodash: an internal vibe-coding tool for Stripe prototypes
(05:26) Why an engineering background helped Owen lower the bar for designers
(07:55) The Cursor rules that taught the Stripe design system
(09:04) Running prototypes on dev boxes vs. locally
(10:30) “Demos, not memos” and rewiring design reviews at Stripe
(14:50) Building Protodash Studio: a browser-based wrapper for prototyping
(19:04) Live demo: variants, line charts, and remixing prototypes in browser
(21:02) Self-testing prototypes that take screenshots and check their work
(23:20) Multiple variant features
(26:08) The annotate-for-AI button for in-canvas feedback
(27:21) Design review mode: comments, summaries, and AI follow-up
(29:39) Why building internal tools beats buying off-the-shelf
(32:50) PMs as the surprise power users of Protodash
(35:20) Live demo: a Black Friday/Cyber Monday pet store dashboard
(42:03) Lo-fi modes, monospace fonts, and “Comic Sans for WIP” at Shopify
(44:45) Quick recap
(45:35) The Radar prototype that changed engineering handoff
(49:08) Lightning round and final thoughts
—
Blog & detailed workflow walkthroughs from this episode:
Stripe’s Owen Williams on Killing ‘Blurple Slop’ with an Internal Prototyping Studio: http://chatprd.ai/how-i-ai/stripe-owen-williams-on-buildling-internal-prototyping-studio
↳ How To Connect a Design System to an AI Code Editor for High Fidelity Prototypes: https://www.chatprd.ai/how-i-ai/workflows/how-to-connect-a-design-system-to-an-ai-code-editor-for-high-fidelity-prototypes
↳ Streamline Design Reviews with an AI-Powered Prototyping Studio: https://www.chatprd.ai/how-i-ai/workflows/streamline-design-reviews-with-an-ai-powered-prototyping-studio
↳ Build a Personal AI App to Track Purchases and User Manuals: https://www.chatprd.ai/how-i-ai/workflows/build-a-personal-ai-app-to-track-purchases-and-user-manuals
—
Tools referenced:
• v0: https://v0.app/
• Cursor: https://cursor.com/
• Claude Code: https://www.claude.com/product/claude-code
• Claude Design: https://www.anthropic.com/news/claude-design-anthropic-labs
• Figma: https://www.figma.com/
• Stripe Radar: https://stripe.com/radar
• Balsamiq: https://balsamiq.com/
—
Where to find Owen Williams:
X: https://x.com/ow
Website: https://owenwillia.ms/
LinkedIn: https://www.linkedin.com/in/owenpwilliams
—
Where to find Claire Vo:
ChatPRD: https://www.chatprd.ai/
Website: https://clairevo.com/
X: https://x.com/clairevo
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

Jason Levin is the CEO and founder of Memelord, an AI-powered meme creation platform that helps brands and individuals create contextual, trending memes. He started Memelord as a $6.90-per-month newsletter sending subscribers to a Google Slides deck, grew it to $100K ARR on Bubble without hiring engineers, then raised $3M to build it into an API-first product.

What you’ll learn:
How Jason grew Memelord from a $6.90/month newsletter to $100K ARR without writing a single line of code
Why “no UX is the best UX” and how agents are becoming Memelord’s primary users
The mandatory vibe-coding rule for his marketing team and how it unlocks unprecedented creativity
Why free tools are the new PDF downloads and how they’ve generated hundreds of thousands of emails
Jason’s hardware hacking projects, including a bedside keyboard that creates Linear tickets without waking his wife
Why AI can be funny (but humans are still funnier) and which model is the funniest
The philosophy of building hyper-personalized software just for yourself
—
Brought to you by:
WorkOS—Make your app enterprise-ready today
Persona—Trusted identity verification for any use case
—
In this episode, we cover:
(00:00) Introduction to Jason Levin and Memelord
(04:28) Demo: Agentic meme creation with OpenClaw
(06:55) “No UX is the best UX”—building for an agent-first future
(08:35) How Memelord started as a $6.90 newsletter with Google Slides
(12:35) Building to $100K ARR on Bubble with 395 workflows
(15:20) Demo: Free tools section that generates hundreds of thousands of emails
(17:59) Why Cursor is perfect for non-technical founders
(20:20) Let your marketers cook—or watch them leave
(24:19) Commit graph that shows the vibe-coding inflection point
(25:25) Tools: Claude, Gemini, Linear, PostHog
(28:19) Build weird stuff in the real world
(33:24) Creative AI use cases
(39:56) Using OpenClaw for calendar analysis
(43:37) Can AI be funny? Which model is funniest?
(45:26) Memes are not slop
(46:45) What Jason doesn’t use AI for
(48:12) Final thoughts
—
Blog & detailed workflow walkthroughs from this episode:
How I AI: Jason Levin’s Workflows for Agentic Memes, Vibe Coding, and Hardware Hacking: https://www.chatprd.ai/how-i-ai/jason-levins-workflows-for-agentic-memes-vibe-coding-and-hardware-hacking
↳ Build a Custom Bedside Keyboard for Idea Capture with Raspberry Pi and ChatGPT: https://www.chatprd.ai/how-i-ai/workflows/build-a-custom-bedside-keyboard-for-idea-capture-with-raspberry-pi-and-chatgpt
↳ Build Free Marketing Tools as Lead Magnets Using AI Code Assistants: https://www.chatprd.ai/how-i-ai/workflows/build-free-marketing-tools-as-lead-magnets-using-ai-code-assistants
↳ Automate Meme Marketing with an AI Agent and OpenClaw: https://www.chatprd.ai/how-i-ai/workflows/automate-meme-marketing-with-an-ai-agent-and-openclaw
—
Tools referenced:
• Memelord API: https://memelord.com/api
• Cursor: https://cursor.com/
• Bubble: https://bubble.io/
• OpenClaw: https://openclaw.ai
• Claude: https://claude.ai/
• ChatGPT: https://chat.openai.com/
• Gemini: https://gemini.google.com/
• Grok: https://grok.x.ai/
• Linear: https://linear.app/
• PostHog: https://posthog.com/
• Zapier: https://zapier.com/
—
Other references:
• Diego Zaks—“The best UX is no UX”: https://x.com/diegozaks/status/1966526522136649980
• Sam Lessin: https://wlessin.com/
• “Stop giving me advice”: https://stopgivingmeadvice.com
• Memelord free tools: https://memelord.com/tools
—
Where to find Jason Levin:
Twitter: https://twitter.com/iamjasonlevin
Instagram: https://instagram.com/iamjasonlevin
LinkedIn: https://www.linkedin.com/in/iamjasonlevin/
Memelord: https://memelord.com
—
Where to find Claire Vo:
ChatPRD: https://www.chatprd.ai/
Website: https://clairevo.com/
LinkedIn: https://www.linkedin.com/in/clairevo/
X: https://x.com/clairevo
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

In this mini episode, I break down OpenAI’s new GPT 5.5 and GPT 5.5 Pro after weeks of early testing. I walk through three real jobs I threw at the model:  building an app for me to teach my second grader more advanced subtraction concepts, tackling a tech debt problem in the ChatPRD codebase, and hacking into a proprietary Bluetooth pixel display that every other model had failed me on. My verdict: higher intelligence, better efficiency, and genuinely autonomous long-running loops that change what I think is worth tackling.

What you’ll learn:
How I think about GPT 5.5 Pro’s pricing vs engineering time, and when I believe the “intelligence tax” is worth paying
Why I treat GPT 5.5 as a developer model first, and why I couldn’t find a consumer use case that justified its intelligence
The exact prompt pattern I use to unlock a long-running autonomous subagent loop
How I got a near-six-hour autonomous run to one-shot 98% of edge cases in a migration over millions of chat threads and drop my Sentry error rate to the floor
Why I’m now throwing GPT 5.5 at tech debt, flaky tests, and security backlogs first
How I combined a Bluetooth packet sniffer and GPT 5.5 to reverse-engineer a proprietary pixel speaker after Claude Code and GPT 5.4 both gave up
How I use the /personality command inside Codex to swap the default “baked potato” tone for something I actually enjoy working with
—
In this episode, I cover:
(00:00) Introduction to GPT 5.5 testing
(00:40) What is GPT 5.5 and how much does it cost?
(03:23) Testing GPT 5.5 in ChatGPT: the intelligence overhang problem
(07:12) Moving to Codex: where GPT 5.5 really shines
(16:01) Hacking a Chinese Bluetooth speaker
(21:47) Final thoughts on GPT 5.5’s intelligence and efficiency
—
Tools referenced:
• GPT 5.5 and GPT 5.5 Pro: https://openai.com/index/introducing-gpt-5-5/
• Codex: https://openai.com/codex/
• ChatGPT: https://chat.openai.com/
• Claude Code: https://claude.ai/code
• Sentry: https://sentry.io/
• Divoom MiniToo: https://divoom.com/products/minitoo
—
Other references:
• OpenAI Codex Security: https://openai.com/index/codex-security-now-in-research-preview/
—
Where to find Claire Vo:
ChatPRD: https://www.chatprd.ai/
Website: https://clairevo.com/
LinkedIn: https://www.linkedin.com/in/clairevo/
X: https://x.com/clairevo
—
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].