Embracing Play and Experimentation in AI Integration

Howie Liu is the co-founder and CEO of Airtable, the no-code platform valued at around $12 billion. After a viral tweet declared “Airtable is dead” based on incorrect data, Howie led a radical transformation: reorganizing the entire company around AI, becoming an “IC CEO” who codes daily, and achieving over $100 million in free cash flow.

What you’ll learn:

1. The “fast thinking” vs. “slow thinking” team structure that lets Airtable ship AI features weekly (inspired by Daniel Kahneman)

2. Why Howie uses AI hourly (not daily) and is Airtable’s #1 inference-cost user globally

3. Why CEOs must become ICs again in the AI era (and how to restructure your calendar to make it possible)

4. Why “playing” with AI tools should be mandatory—Howie tells employees to cancel all meetings for a week to experiment

5. The specific skills product managers, engineers, and designers need to develop to succeed in the AI era

6. Why evals can kill innovation (and when to use “vibes” instead)

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Brought to you by:

LucidLink—Real-time cloud storage for teams

DX—The developer intelligence platform designed by leading researchers

Claude.ai—The AI for problem solvers and enterprise

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Where to find Howie Liu

• X: https://x.com/howietl

• LinkedIn: https://www.linkedin.com/in/howieliu/

• Email: howie@airtable.com

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Introduction to Howie Liu and Airtable

(04:05) The “Airtable is dead” viral tweet controversy

(08:07) The rise of IC CEOs

(10:57) AI’s paradigm shift in product development

(16:27) Specific changes Airtable has made

(21:38) Fast- and slow-thinking teams

(32:57) The emergence of new form factors in AI models

(34:48) Airtable’s vision and philosophy

(40:20) Empowering teams with AI tools

(46:50) Encouraging experimentation and play

(50:55) Cross-functional skills in product teams

(01:03:35) The importance of evals and open-ended testing

(01:08:06) Key strategies for AI-driven success

(01:12:43) Counterintuitive startup wisdom

(01:22:21) Don't step away from the details that you love

(01:25:50) Advice for aspiring engineers and designers

(01:30:00) Lightning round and final thoughts

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Referenced:

• Airtable: https://www.airtable.com/

• All In podcast: https://allin.com/

• Nikita Bier on X: https://x.com/nikitabier

• Figma: https://www.figma.com/

• The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder and CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper

• Every: https://every.to/

• Cursor: https://cursor.com/

• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell

• Windsurf: https://windsurf.com/

• Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan

• Rippling: https://www.rippling.com/

• Omni: https://www.airtable.com/lp/ai-psu-plp

• How ChatGPT accidentally became the fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley

• Palantir: https://www.palantir.com/

• Harvey: https://www.harvey.ai/

• v0: https://v0.dev/

• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch

• Replit: https://replit.com/

• Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad

• Lovable: https://lovable.dev/

• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika

• Runway Game Worlds: https://play.runwayml.com/login

• Sesame: https://www.sesame.com

• NotebookLM: https://notebooklm.google

• Salesforce: https://www.salesforce.com

• Andrew Ofstad on LinkedIn: https://www.linkedin.com/in/aofstad/

• Stripe: https://stripe.com/

• Eames chair: https://en.wikipedia.org/wiki/Eames_Lounge_Chair

• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai

• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next

• IDEO design thinking: https://designthinking.ideo.com/

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• The Studio on AppleTV+: https://tv.apple.com/us/show/the-studio/umc.cmc.7518algxc4lsoobtsx30dqb52

• Silicon Valley on HBOMax: https://www.hbomax.com/shows/silicon-valley/b4583939-e39f-4b5c-822d-5b6cc186172d

• Self Edge: https://www.selfedge.com/

• Studio D’Artisan: https://www.selfedge.com/studio-dartisan

• Whitesville T-shirt: https://store.toyo-enterprise.co.jp/shopbrand/ct48/

• Guest Series | Dr. Paul Conti: How to Understand & Assess Your Mental Health: https://www.hubermanlab.com/episode/guest-series-dr-paul-conti-how-to-understand-and-assess-your-mental-health

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Recommended books:

• Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555

• The Three-Body Problem: https://www.amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032

• Trauma: The Invisible Epidemic: How Trauma Works and How We Can Heal From It: https://us.amazon.com/Trauma-Invisible-Epidemic-Works-Heal/dp/1683647351/

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

Lenny may be an investor in the companies discussed.