How I AI

Ryan Carson is a five-time founder who has spent the past 20 years building, scaling, and selling startups. In this episode, he shares his playbook for using AI to build products, turning “vibe coding” into a structured and scalable approach that can replace full engineering teams.

What you’ll learn:

1. A simple three-file system that transforms chaotic AI coding into a structured, reliable process

2. How to create AI-generated PRDs and task lists that actually work

3. A step-by-step workflow using Cursor to build features systematically

4. Why slowing down to provide proper context is the secret to speeding up your AI development

5. How to use model context protocols (MCPs) to extend your AI’s capabilities beyond just coding

6. Why founders can now build entire companies with minimal engineering teams and how Ryan is doing it himself

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Brought to you by:

ChatPRD—An AI copilot for PMs and their teams

Notion—The best AI tools for work

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Where to find Ryan Carson:

Website: https://www.ryancarson.com/about

LinkedIn: https://www.linkedin.com/in/ryancarson/

X: https://x.com/ryancarson

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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

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In this episode, we cover:

(00:00) Introduction and Ryan’s recent AI projects

(03:25) Demo: Creating a PRD with Cursor

(05:00) Ryan’s open source links: https://github.com/snarktank/ai-dev-tasks

(09:23) Repo Prompt: https://repoprompt.com/

(09:53) Quick recap and common mistakes to avoid

(11:00) Demo: Generating a task list from the PRD

(15:31) The importance of context when working with LLMs

(18:07) Demo: Working through tasks systematically using Cursor

(18:56) Change management

(20:00) How task lists save time for product managers

(21:50) Demo: Using MCPs for front-end testing

(24:50) Specific MCPs and what to use them for

(26:45) Demo: Using Repo Prompt to gain precise control over context

(31:23) Music’s role in Ryan’s development stack

(32:10) Lightning round and final thoughts

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Tools referenced:

• ChatGPT: https://chat.openai.com/

• Claude: https://claude.ai/

• Gemini 2.5 Pro: https://deepmind.google/models/gemini/pro/.

• Repo Prompt: https://repoprompt.com/

• Taskmaster: https://github.com/nooqta/taskmaster

• Browserbase: https://browserbase.com/

• Stagehand: https://docs.stagehand.dev/integrations/mcp-server

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Other references:

• PostgreSQL: https://www.postgresql.org/

• Prisma: https://www.prisma.io/

• SQL: https://www.sql.org/

• MCP: https://www.anthropic.com/news/model-context-protocol

• VS Code: https://code.visualstudio.com/

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email jordan@penname.co.

Hilary Gridley, Head of Core Product at Whoop, shares how she uses dozens of custom GPTs for her team that think and give feedback like her, allowing her to scale herself up and create time for higher-value work.

What you’ll learn:

1. A step-by-step process for creating GPTs that “think like you” by reverse engineering your own decision criteria

2. How to turn your management expertise into clear evaluation rubrics that AI can consistently apply

3. Practical techniques for improving team writing and presentations with AI-powered feedback

4. Why GPTs are the perfect tool for scaling good management practices without requiring prompt engineering skills

5. How to use AI to get invited to more strategic meetings by improving your written point of view

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Brought to you by:

Orkes—The enterprise platform for reliable applications and agentic workflows

Vanta—Automate compliance and simplify security

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Where to find Hilary Gridley:

Newsletter: https://hils.substack.com/

LinkedIn: https://www.linkedin.com/in/hilarygridley/

X: https://x.com/yourgirlhils

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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

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In this episode, we cover:

(00:00) Intro

(02:52) Creating GPTs that think like you

(04:23) Demo: Reverse engineering a recommendation algorithm

(13:06) The value of articulating taste

(15:33) Demo: Creating a slide deck evaluator GPT

(19:19) Testing your new GPT

(21:32) Scaling GPTs across your team

(23:52) Demo: Using AI to improve your writing

(30:32) Lightning round and final thoughts

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Tools referenced:

• GPTs: https://chat.openai.com/gpts

• ChatGPT: https://chat.openai.com/

• Claude: https://claude.ai/

• Bolt: https://bolt.new/

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Other references:

• Whoop: https://www.whoop.com/

• Norwegian School of Economics: https://www.nhh.no/en/

• Researchers at NHH have uncovered significant gender disparities in the adoption of generative AI tools like ChatGPT: https://www.nhh.no/en/nhh-bulletin/article-archive/2024/september/study-reveals-gender-gap-in-ai-tool-usage-among-students/

• How to Become a Supermanager with AI: https://maven.com/hilary-gridley/ai-powered-people-management

• Girls in the Loop: https://grrlsintheloop.ai/

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email jordan@penname.co.

Joel Unger, design director at Atlassian, shares how AI is transforming the way he designs Trello and other products. He walks through real-world workflows using tools like Midjourney and Cursor to prototype complex interactions, re-create brand assets, and explore creative directions faster than ever. You’ll hear how AI is helping designers focus on higher-level thinking, communicate better with developers, and push creative boundaries—all without replacing the human touch.

What you’ll learn:

1. How to prototype complex UI interactions using AI
2. A workflow for re-creating animated brand assets without motion design tools
3. How to leverage image generation tools like Midjourney to explore design directions and create mood boards
4. How to use Cursor to re-create animated SVG assets
5. Why AI frees designers to operate at a higher level of creativity
6. How AI improves designer-developer collaboration by showcasing interactive intent
7. Why embracing AI is key to staying ahead in the evolving design landscape
8. The limitations of current AI tools and where they still fall short

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Brought to you by:

• ⁠Paragon⁠—Ship every SaaS integration your customers want

⁠• WorkOS⁠—Make your app enterprise-ready today

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Where to find Joel Unger:

Website: https://joelunger.com/

LinkedIn: https://www.linkedin.com/in/joelunger/

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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

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In this episode, we cover:

(00:00) Intro and Joel's background

(02:46) Trello's new productivity features

(04:24) Traditional design process limitations in Figma

(05:22) Using Cursor to prototype interactive panel systems

(07:39) From prototype to production: collaborating with developers

(08:52) How Joel used AI to prepare for the podcast

(10:50) How AI saves designer time for deeper thinking

(11:23) Last-minute logo animation using Cursor

(13:50) Using Midjourney for character design exploration

(14:56) Creating a mood board for Taco: the Trello husky mascot

(16:49) How AI is changing design thinking and workflows

(18:18) Lightning round and closing thoughts

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Tools referenced:

• Confluence: https://www.atlassian.com/software/confluence

• Bitbucket: https://bitbucket.org/product/

• Trello: https://trello.com/home

• Figma: https://www.figma.com

• Cursor: https://www.cursor.com/

• ChatGPT: https://chatgpt.com/

• Midjourney: https://www.midjourney.com/

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Other reference:

• Atlassian: https://www.atlassian.com/

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email jordan@penname.co.

Cody De Arkland is the senior director of developer experience at Sentry, leading a team that empowers developers to build and ship software with greater safety and efficiency. Watch him speed-run the creation of a 3D multiplayer flight simulator—from scratch—in just 15 minutes, demonstrating the power (and creativity) that vibe coding enables.

What you’ll learn:

• How to approach building complex applications with AI by starting broad and iterating on specific features

• The process of using multiple AI coding assistants simultaneously to build different components

• Techniques for learning new technologies and frameworks through AI-assisted exploration

• How to troubleshoot and fix issues when AI implementations don’t work as expected

• The parallels between building fun projects and enterprise software with AI assistance

• Strategies for keeping AI tools focused when they go off track or add unwanted features

• The incredible velocity and productivity gains possible with modern AI coding tools

• How anyone can now build sophisticated applications with minimal prior experience

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Brought to you by:

⁠Enterpret⁠—Customer superintelligence platform for product and CX teams

⁠WorkOS⁠—Make your app enterprise-ready today with WorkOS

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Where to find Cody De Arkland:

Website: https://codyde.io/

LinkedIn: https://www.linkedin.com/in/codydearkland/

X: https://x.com/Codydearkland

GitHub: https://github.com/codyde

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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

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In this episode, we cover:

(00:00) Introduction to Cody

(02:45) AI tools he’s using

(04:38) How Cody vibe coded a multiplayer game: Spaceflight

(09:37) Demo: Starting a new flight simulator project from scratch

(13:49) How to learn about libraries and technologies for projects

(17:06) First run of the new flight simulator game

(19:26) Using multiple AI coding assistants simultaneously

(20:43) Unexpected features and visual improvements

(21:26) Testing the multiplayer functionality

(22:31) Reflecting on the development process and iteration

(26:47) Lightning round and final thoughts

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Tools referenced:

• Cursor: https://www.cursor.com/

• Windsurf: https://windsurf.com/

• Claude: https://claude.ai/new

• Bolt: https://bolt.new/

• React: https://react.dev/

• v0: https://v0.dev/

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Other references:

• Sentry: https://sentry.io/

• MCP: https://www.anthropic.com/news/model-context-protocol

• Spaceflight: http://spaceflight.gg/

• Three.js: https://threejs.org/

• Socket.io: https://socket.io/

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email jordan@penname.co

Farhad Manjoo, a former New York Times and Wall Street Journal columnist, reveals his AI-enhanced writing workflow, from research to finding the perfect metaphor, and how these tools have transformed his creative process without replacing his unique voice.

What you’ll learn:

• How AI evolved from a simple tool to an essential writing companion

• Using ChatGPT as a research assistant with web search capabilities

• The “super-thesaurus” technique for finding the perfect words and idioms

• How AI helps brainstorm ideas and refine arguments

• The benefits of having an “always-on” writing partner in a remote work world

• Using AI as a first reader to evaluate drafts in progress

• Why AI enhances rather than replaces a writer’s unique voice

• Practical tips for getting unstuck when AI doesn’t deliver

• How AI speeds up the writing process while improving quality

• The future improvements that would make AI even more valuable for writers

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Brought to you by:

• Enterpret—Customer SuperIntelligence Platform for Product and CX teams

• Vanta—Automate compliance and simplify security with Vanta

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Where to find Farhad Manjoo:

• LinkedIn: https://www.linkedin.com/in/farhad-manjoo-161229/

• X: https://x.com/fmanjoo

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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

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In this episode, we cover:

(00:00) Intro

(02:40) Farhad’s journey from skepticism to adoption of AI tools

(04:20) Brainstorming with ChatGPT

(06:54) Assessing the quality of AI-sourced information

(08:34) How ChatGPT helps identify new angles and perspectives

(10:52) Using ChatGPT to find alternatives to clichéd expressions

(16:44) The “super-thesaurus” technique for finding perfect words and idioms

(20:12) Using AI as a first reader for draft evaluation

(22:15) Lightning round

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Tools referenced:

• ChatGPT: https://openai.com/chatgpt/overview/

• Cursor: https://www.cursor.com

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Other references:

• New York Times: https://www.nytimes.com/

• The Wall Street Journal: https://www.wsj.com/

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email jordan@penname.co.

Sahil Lavingia is the founder and CEO of Gumroad, where AI agents are already writing 41% of all code commits, and he’s targeting 80% by year’s end. Sahil demonstrates how this approach allows him to transform what would typically be two-week projects into two-hour implementations—a 40x productivity increase.

What you’ll learn:

1. The exact AI workflow Sahil uses to build features 40x faster—from prototyping in v0 to implementation with Devin
2. How Gumroad incentivizes AI adoption across the organization with $33,000 bounties for engineers who outperform the CEO
3. How to use component libraries like shadcn/ui for effective AI development
4. How AI is shifting engineering roles toward architecture and tech-debt removal while enabling designers and PMs to ship features directly
5. Why spending more time on UX iteration becomes possible (and necessary) when implementation costs drop dramatically
6. Which organizational functions will be transformed by AI next

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Brought to you by:

Enterpret—Customer SuperIntelligence Platform for Product and CX teams

Vanta—Automate compliance and simplify security with Vanta

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Where to find Sahil Lavingia:

Gumroad: https://gumroad.com/

Website: https://sahillavingia.com/

LinkedIn: https://www.linkedin.com/in/sahillavingia

X: https://x.com/shl

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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

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In this episode, we cover:

(⁠00:00⁠) Sahil’s background

(⁠02:31⁠) How soon will AI do most engineering?

(⁠04:08⁠) Live demo: redesigning with v0, Devin, and Cursor

(⁠09:30⁠) Using the right tools

(⁠11:03⁠) Prototyping and iteration with AI

(⁠19:45⁠) Incentivizing AI adoption in teams

(⁠24:50⁠) “Magical” date-picker component development

(⁠31:47⁠) AI’s impact on marketing, sales, and support

(⁠36:50⁠) Deciding what to build when AI builds everything

(⁠40:02⁠) Conclusion and final thoughts

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Referenced:

• Devin: https://devin.ai/

• Cursor: https://www.cursor.so/

• v0: https://v0.dev/

• Tobi Lütke’s tweet on how AI usage is now a baseline expectation at Shopify: https://x.com/tobi/status/1909231499448401946

• Flexile: https://app.flexile.com/

• shadcn: https://github.com/shadcn/ui

• Gusto: https://gusto.com/

• GitHub: https://github.com/

• Figma: https://www.figma.com/

• Slack: https://slack.com/

• Vercel: https://vercel.com/

• Next.js: https://nextjs.org/

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email jordan@penname.co.

How I AI, hosted by Claire Vo, is for anyone struggling to keep up with the latest AI advancements, and wondering how to actually use these magical new tools to improve the quality and efficiency of their work. In each episode, guests will demonstrate a specific, practical, and impactful way they’ve learned to use AI in their life. Forget theoretical debates—this podcast is about real, concrete suggestions. Expect 30-minute episodes, live demos, and tips/tricks/workflows you can implement immediately. Whether you’re building products, leading teams, or just want to level up your AI game, this show helps demystify AI and give you the skills you need to thrive in this new world.