How I AI, hosted by Claire Vo, is for anyone wondering how to actually use these magical new tools to improve the quality and efficiency of their work. In each episode, guests will share a specific, practical, and impactful way they’ve learned to use AI in their work or life. Expect 30-minute episodes, live screen sharing, and tips/tricks/workflows you can copy immediately. If you want to demystify AI and learn the skills you need to thrive in this new world, this podcast is for you.
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Gumroad CEO's playbook to 40x his team's productivity with v0, Cursor, and Devin | Sahil Lavingia
Tuesday, April 22, 2025 • Duration 45:13
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:
The exact AI workflow Sahil uses to build features 40x faster—from prototyping in v0 to implementation with Devin
How Gumroad incentivizes AI adoption across the organization with $33,000 bounties for engineers who outperform the CEO
How to use component libraries like shadcn/ui for effective AI development
How AI is shifting engineering roles toward architecture and tech-debt removal while enabling designers and PMs to ship features directly
Why spending more time on UX iteration becomes possible (and necessary) when implementation costs drop dramatically
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
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email jordan@penname.co.
Introducing How I AI
Sunday, April 20, 2025 • Duration 02:03
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.
How this former NYT columnist uses ChatGPT to brainstorm ideas, do research, and find the perfect metaphor | Farhad Manjoo
Monday, April 28, 2025 • Duration 25:45
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
Vibe coding a 3D multiplayer game in 15 minutes—with no game dev experience | Cody De Arkland (Senior Director of Developer Experience at Sentry)
Monday, May 5, 2025 • Duration 31:32
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:
A designer's guide to AI: Why designing in Cursor lets you prototype 10x faster, simplifies collaboration, and accelerates getting ideas out of your head | Joel Unger
Monday, May 12, 2025 • Duration 20:55
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:
How to prototype complex UI interactions using AI
A workflow for re-creating animated brand assets without motion design tools
How to leverage image generation tools like Midjourney to explore design directions and create mood boards
How to use Cursor to re-create animated SVG assets
Why AI frees designers to operate at a higher level of creativity
How AI improves designer-developer collaboration by showcasing interactive intent
Why embracing AI is key to staying ahead in the evolving design landscape
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
How custom GPTs can make you a better manager | Hilary Gridley (Head of Core Product at Whoop)
Monday, May 19, 2025 • Duration 36:08
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
The exact AI playbook (using MCPs, custom GPTs, Granola) that saved ElevenLabs $100k+ and helps them ship daily | Luke Harries (Head of Growth)
Monday, June 2, 2025 • Duration 44:24
Luke Harries, Head of Growth at ElevenLabs, the leading AI voice technology company, shares how he’s automating marketing workflows with AI—from case studies to translations to WhatsApp integrations—saving his company over $140,000 while making everything a launch.
What you’ll learn:
1. How to create polished case studies in minutes using AI transcription and a custom GPT
2. How ElevenLabs built a custom AI translation system that saved them $140,000 annually and eliminated agency headaches
3. How to use Model Context Protocols (MCPs) to connect AI assistants to your WhatsApp messages
4. The “everything is a launch” philosophy that helps ElevenLabs maintain consistent marketing momentum
5. Why marketers should learn to code with AI tools like Cursor
6. How to create effective custom GPTs by focusing on prompt engineering rather than output editing
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Brought to you by:
Orkes—The enterprise platform for reliable applications and agentic workflows
Retool—AI that’s designed for developers, and built for the enterprise
A 3-step AI coding workflow for solo founders | Ryan Carson (5x founder)
Monday, May 26, 2025 • Duration 34:44
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
Gamma’s head of design shares how his small team uses AI to synthesize feedback, generate on-brand imagery, and maintain design quality while serving users in 60+ countries | Zach Leach
Monday, June 9, 2025 • Duration 36:20
Zach Leach, head of design at Gamma, reveals how his small team uses AI to analyze global feedback, create on-brand imagery, and maintain design quality while serving users in more than 60 countries.
What you’ll learn:
How Gamma analyzes feedback from their 60% international user base using ChatGPT’s deep research capabilities
How to transform hundreds of multilingual feedback items into actionable design insights
A simple workflow for creating on-brand imagery using Midjourney-style references
How to use AI to maintain brand consistency across a globally distributed product
The secret to removing image backgrounds instantly using Replicate
How to create consistent, high-quality job descriptions in minutes using AI templates
A designer's guide to Cursor: How to build interactive prototypes with sound, explore visual styles, and transform data visualizations | Elizabeth Lin
Monday, June 16, 2025 • Duration 35:07
Elizabeth Lin is an independent design educator who has crafted learning experiences for Khan Academy, Primer, and Lambda School. She currently runs design is a party, an alternative online design school where she teaches courses like The Art of Visual Design and Prototyping with Cursor. In this episode, she shares how designers can leverage Cursor to create interactive prototypes with sound, explore different visual aesthetics, and transform basic designs into polished interfaces—all without deep coding knowledge.
What you'll learn:
How to use Cursor to explore different design aesthetics—from brutalist to Y2K to cyberpunk
A simple workflow for creating interactive sound elements in prototypes that would be difficult with traditional design tools
A step-by-step process for transforming an ugly dashboard into a polished design using strategic prompting
Why broadening your inspiration sources helps Cursor generate more unique and creative design
Techniques for teaching AI tools to understand your design preferences and taste
A practical approach to creating data-driven prototypes by connecting Cursor with Notion databases
How to use Cursor Rules to streamline your prototyping workflow and avoid repetitive setup tasks
(02:42) Building the Gamma AI image editing feature
(05:25) Using ChatGPT’s deep research for feedback analysis
(09:10) How feedback was analyzed before AI tools
(10:10) Benefits of deep research vs. basic scripting
(12:40) Insights from ChatGPT's deep research
(16:41) Demo of Midjourney workflow for creating on-brand art
(23:54) Using Replicate for background removal
(25:40) Style references (SREF) and brand consistency in Midjourney
(29:19) An AI workflow for creating consistent job descriptions
(32:27) Conclusion and final thoughts
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ChatGPT feedback prompt
“This is some feedback we’ve received about our AI image editing feature. I want you to analyze the feedback and find where we are doing poorly and where we are doing well. Break down for our product team what kinds of things we are doing well and why, and what kinds of things we are doing poorly and why. What do people love? What do people hate? Where can we improve?”
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email jordan@penname.co.
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