Gumroad CEO's playbook to 40x his team's...

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.