World Model · podcast knowledge graph

Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon

2026-01-11 · 86 min · 61 entities

episode page audio

Asserted relationships

  • → references Citations concept
    0.77
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://scholar.google.com/citations?hl=en&user=I1EvjZsAAAAJ
  • → references Three Body Problem Cixin Liu book
    0.77
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032
  • → references Fire Upon Deep Zones Thought book
    0.77
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285
  • 0.77
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://amazon.com/When-Breath-Becomes-Paul-Kalanithi/dp/081298840X
  • → references booking.com place
    0.77
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://booking.com/
  • 0.77
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://en.wikipedia.org/wiki/The_unexamined_life_is_not_worth_living
  • → references Awesome Generative Ai Guide product
    0.77
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://github.com/aishwaryanr/awesome-generative-ai-guide
  • → references Aish Reganti person
    0.77
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://x.com/aish_reganti
  • → references Sai Kiriti Badam person
    0.77
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://linkedin.com/in/sai-kiriti-badam
  • → hosted by Lenny Rachitsky person
    0.55
    evidence rules-v4
    Feed author/publisher: Lenny Rachitsky
  • → recommended Three Body Problem Cixin Liu book
    0.50
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032
  • → recommended Three Body Problem Cixin Liu book
    0.50
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032
  • → recommended Fire Upon Deep Zones Thought book
    0.50
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285
  • → recommended Fire Upon Deep Zones Thought book
    0.50
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285
  • → recommended When Breath Becomes Paul Kalanithi book
    0.50
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://amazon.com/When-Breath-Becomes-Paul-Kalanithi/dp/081298840X
  • → recommended When Breath Becomes Paul Kalanithi book
    0.50
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://amazon.com/When-Breath-Becomes-Paul-Kalanithi/dp/081298840X
  • → works at Every company
    0.50
    evidence rules-v4
    CEO of Every
  • → works at Every company
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    evidence rules-v4
    CEO of Every
  • → discusses Technology company
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    evidence rules-v4
    Feed category: Technology
  • → discusses Business concept
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    evidence rules-v4
    Feed category: Business
  • → discusses Entrepreneurship concept
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    Feed category: Entrepreneurship
  • → references penname.co website
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    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://penname.co/
  • → references wisprflow.ai website
    0.38
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://wisprflow.ai/
  • → references noahpinion.blog website
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    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://noahpinion.blog/
  • → references raycast.com website
    0.38
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://raycast.com/
  • → references Business Account person
    0.38
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://brex.com/product/business-account?ref_code=bmk_dp_brand1H25_ln_new_fs
  • → references lmarena.ai website
    0.38
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://lmarena.ai/
  • → references B4583939 E39f 4b5c 822d 5b6cc186172d website
    0.38
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://hbomax.com/shows/silicon-valley/b4583939-e39f-4b5c-822d-5b6cc186172d
  • → references levelup-labs.ai company
    0.38
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://levelup-labs.ai/
  • → references rackspace.com website
    0.38
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://rackspace.com/
  • → references SemanticDiffusion website
    0.38
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://martinfowler.com/bliki/SemanticDiffusion.html
  • → references Leaderboards website
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    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://artificialanalysis.ai/leaderboards/providers
  • 0.38
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://bbc.com/travel/article/20240222-air-canada-chatbot-misinformation-what-travellers-should-know
  • → references Clair Obscur Expedition 33 website
    0.38
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://store.steampowered.com/app/1903340/Clair_Obscur_Expedition_33

Entities found in this episode

websites 22

  • mentioned penname.co website
    0.45
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://penname.co/
  • mentioned wisprflow.ai website
    0.45
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://wisprflow.ai/
  • mentioned noahpinion.blog website
    0.45
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://noahpinion.blog/
  • mentioned raycast.com website
    0.45
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://raycast.com/
  • mentioned lmarena.ai website
    0.45
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://lmarena.ai/
  • 0.45
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://hbomax.com/shows/silicon-valley/b4583939-e39f-4b5c-822d-5b6cc186172d
  • mentioned rackspace.com website
    0.45
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://rackspace.com/
  • mentioned SemanticDiffusion website
    0.45
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://martinfowler.com/bliki/SemanticDiffusion.html
  • mentioned Leaderboards website
    0.45
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://artificialanalysis.ai/leaderboards/providers
  • 0.45
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://bbc.com/travel/article/20240222-air-canada-chatbot-misinformation-what-travellers-should-know
  • mentioned Clair Obscur Expedition 33 website
    0.45
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://store.steampowered.com/app/1903340/Clair_Obscur_Expedition_33
  • references penname.co website
    0.38
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://penname.co/
  • references wisprflow.ai website
    0.38
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://wisprflow.ai/
  • references noahpinion.blog website
    0.38
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://noahpinion.blog/
  • references raycast.com website
    0.38
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://raycast.com/
  • references lmarena.ai website
    0.38
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://lmarena.ai/
  • 0.38
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://hbomax.com/shows/silicon-valley/b4583939-e39f-4b5c-822d-5b6cc186172d
  • references rackspace.com website
    0.38
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://rackspace.com/
  • references SemanticDiffusion website
    0.38
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://martinfowler.com/bliki/SemanticDiffusion.html
  • references Leaderboards website
    0.38
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://artificialanalysis.ai/leaderboards/providers
  • 0.38
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://bbc.com/travel/article/20240222-air-canada-chatbot-misinformation-what-travellers-should-know
  • references Clair Obscur Expedition 33 website
    0.38
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://store.steampowered.com/app/1903340/Clair_Obscur_Expedition_33

books 12

  • 0.90
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032
  • 0.90
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285
  • 0.90
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://amazon.com/When-Breath-Becomes-Paul-Kalanithi/dp/081298840X
  • 0.77
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032
  • 0.77
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285
  • 0.77
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://amazon.com/When-Breath-Becomes-Paul-Kalanithi/dp/081298840X
  • recommended Three Body Problem Cixin Liu book
    0.50
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032
  • recommended Three Body Problem Cixin Liu book
    0.50
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032
  • recommended Fire Upon Deep Zones Thought book
    0.50
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285
  • recommended Fire Upon Deep Zones Thought book
    0.50
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285
  • 0.50
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://amazon.com/When-Breath-Becomes-Paul-Kalanithi/dp/081298840X
  • 0.50
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://amazon.com/When-Breath-Becomes-Paul-Kalanithi/dp/081298840X

concepts 8

  • mentioned Citations concept
    0.90
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://scholar.google.com/citations?hl=en&user=I1EvjZsAAAAJ
  • 0.90
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://en.wikipedia.org/wiki/The_unexamined_life_is_not_worth_living
  • references Citations concept
    0.77
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://scholar.google.com/citations?hl=en&user=I1EvjZsAAAAJ
  • 0.77
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://en.wikipedia.org/wiki/The_unexamined_life_is_not_worth_living
  • mentioned Business concept
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    Feed category: Business
  • mentioned Entrepreneurship concept
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    evidence rules-v4
    Feed category: Entrepreneurship
  • discusses Business concept
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    evidence rules-v4
    Feed category: Business
  • discusses Entrepreneurship concept
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    evidence rules-v4
    Feed category: Entrepreneurship

persons 8

  • mentioned Aish Reganti person
    0.90
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://x.com/aish_reganti
  • mentioned Sai Kiriti Badam person
    0.90
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://linkedin.com/in/sai-kiriti-badam
  • references Aish Reganti person
    0.77
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://x.com/aish_reganti
  • references Sai Kiriti Badam person
    0.77
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://linkedin.com/in/sai-kiriti-badam
  • mentioned Lenny Rachitsky person
    0.70
    evidence rules-v4
    Feed author/publisher: Lenny Rachitsky
  • hosted by Lenny Rachitsky person
    0.55
    evidence rules-v4
    Feed author/publisher: Lenny Rachitsky
  • mentioned Business Account person
    0.45
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://brex.com/product/business-account?ref_code=bmk_dp_brand1H25_ln_new_fs
  • references Business Account person
    0.38
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://brex.com/product/business-account?ref_code=bmk_dp_brand1H25_ln_new_fs

companys 7

  • mentioned Every company
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    evidence rules-v4
    CEO of Every
  • mentioned Technology company
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    Feed category: Technology
  • works at Every company
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    evidence rules-v4
    CEO of Every
  • works at Every company
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    evidence rules-v4
    CEO of Every
  • mentioned levelup-labs.ai company
    0.45
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://levelup-labs.ai/
  • discusses Technology company
    0.40
    evidence rules-v4
    Feed category: Technology
  • references levelup-labs.ai company
    0.38
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://levelup-labs.ai/

places 2

  • mentioned booking.com place
    0.90
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://booking.com/
  • references booking.com place
    0.77
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://booking.com/

products 2

  • mentioned Awesome Generative Ai Guide product
    0.90
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://github.com/aishwaryanr/awesome-generative-ai-guide
  • references Awesome Generative Ai Guide product
    0.77
    evidence rules-v4
    Link in episode "Why most AI products fail: Lessons from 50+ AI deployments at OpenAI, Google, and Amazon": https://github.com/aishwaryanr/awesome-generative-ai-guide
Episode description as stored
Aishwarya Naresh Reganti and Kiriti Badam have helped build and launch more than 50 enterprise AI products across companies like OpenAI, Google, Amazon, and Databricks. Based on these experiences, they’ve developed a small set of best practices for building and scaling successful AI products. The goal of this conversation is to save you and your team a lot of pain and suffering. We discuss: 1. Two key ways AI products differ from traditional software, and why that fundamentally changes how they should be built 2. Common patterns and anti-patterns in companies that build strong AI products versus those that struggle 3. A framework they developed from real-world experience to iteratively build AI products that create a flywheel of improvement 4. Why obsessing about customer trust and reliability is an underrated driver of successful AI products 5. Why evals aren’t a cure-all, and the most common misconceptions people have about them 6. The skills that matter most for builders in the AI era — Brought to you by: Merge —The fastest way to ship 220+ integrations: https://merge.dev/lenny Strella —The AI-powered customer research platform: https://strella.io/lenny Brex —The banking solution for startups: https://www.brex.com/product/business-account?ref_code=bmk_dp_brand1H25_ln_new_fs — Transcript: https://www.lennysnewsletter.com/p/what-openai-and-google-engineers-learned — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/183007822/referenced — Get 15% off Aishwarya and Kiriti’s Maven course, Building Agentic AI Applications with a Problem-First Approach , using this link: https://bit.ly/3V5XJFp — Where to find Aishwarya Naresh Reganti: • LinkedIn: https://www.linkedin.com/in/areganti • GitHub: https://github.com/aishwaryanr/awesome-generative-ai-guide • X: https://x.com/aish_reganti — Where to find Kiriti Badam: • LinkedIn: https://www.linkedin.com/in/sai-kiriti-badam • X: https://x.com/kiritibadam — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Aishwarya and Kiriti (05:03) Challenges in AI product development (07:36) Key differences between AI and traditional software (13:19) Building AI products: start small and scale (15:23) The importance of human control in AI systems (22:38) Avoiding prompt injection and jailbreaking (25:18) Patterns for successful AI product development (33:20) The debate on evals and production monitoring (41:27) Codex team’s approach to evals and customer feedback (45:41) Continuous calibration, continuous development (CC/CD) framework (58:07) Emerging patterns and calibration (01:01:24) Overhyped and under-hyped AI concepts (01:05:17) The future of AI (01:08:41) Skills and best practices for building AI products (01:14:04) Lightning round and final thoughts — Referenced: • LevelUp Labs: https://levelup-labs.ai/ • Why your AI product needs a different development lifecycle: https://www.lennysnewsletter.com/p/why-your-ai-product-needs-a-different • Booking.com : https://www.booking.com • Research paper on agents in production (by Matei Zaharia’s lab): https://arxiv.org/pdf/2512.04123 • Matei Zaharia’s research on Google Scholar: https://scholar.google.com/citations?user=I1EvjZsAAAAJ&hl=en • The coming AI security crisis (and what to do about it) | Sander Schulhoff: https://www.lennysnewsletter.com/p/the-coming-ai-security-crisis • Gajen Kandiah on LinkedIn: https://www.linkedin.com/in/gajenkandiah • Rackspace: https://www.rackspace.com • The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper • Semantic Diffusion: https://martinfowler.com/bliki/SemanticDiffusion.html • LMArena: https://lmarena.ai • Artificial Analysis: https://artificialanalysis.ai/leaderboards/providers • Why humans are