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Lenny's Podcast: Product | Career | Growth

Lenny's Podcast: Product | Career | Growth

By: Lenny Rachitsky
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 Interviews with world-class product leaders and growth experts to uncover concrete, actionable, and tactical advice to help you build, launch, and grow your own product.Lenny Rachitsky Economics Leadership Management & Leadership
Episodes
  • The coming AI security crisis (and what to do about it) | Sander Schulhoff

    The coming AI security crisis (and what to do about it) | Sander Schulhoff
    Dec 21 2025
    Sander Schulhoff is an AI researcher specializing in AI security, prompt injection, and red teaming. He wrote the first comprehensive guide on prompt engineering and ran the first-ever prompt injection competition, working with top AI labs and companies. His dataset is now used by Fortune 500 companies to benchmark their AI systems security, he’s spent more time than anyone alive studying how attackers break AI systems, and what he’s found isn’t reassuring: the guardrails companies are buying don’t actually work, and we’ve been lucky we haven’t seen more harm so far, only because AI agents aren’t capable enough yet to do real damage.We discuss:1. The difference between jailbreaking and prompt injection attacks on AI systems2. Why AI guardrails don’t work3. Why we haven’t seen major AI security incidents yet (but soon will)4. Why AI browser agents are vulnerable to hidden attacks embedded in webpages5. The practical steps organizations should take instead of buying ineffective security tools6. Why solving this requires merging classical cybersecurity expertise with AI knowledge—Brought to you by:Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lennyMetronome—Monetization infrastructure for modern software companies: https://metronome.com/GoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny—Transcript: https://www.lennysnewsletter.com/p/the-coming-ai-security-crisis—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181089452/my-biggest-takeaways-from-this-conversation—Where to find Sander Schulhoff:• X: https://x.com/sanderschulhoff• LinkedIn: https://www.linkedin.com/in/sander-schulhoff• Website: https://sanderschulhoff.com• AI Red Teaming and AI Security Masterclass on Maven: https://bit.ly/44lLSbC—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 Sander Schulhoff and AI security(05:14) Understanding AI vulnerabilities(11:42) Real-world examples of AI security breaches(17:55) The impact of intelligent agents(19:44) The rise of AI security solutions(21:09) Red teaming and guardrails(23:44) Adversarial robustness(27:52) Why guardrails fail(38:22) The lack of resources addressing this problem(44:44) Practical advice for addressing AI security(55:49) Why you shouldn’t spend your time on guardrails(59:06) Prompt injection and agentic systems(01:09:15) Education and awareness in AI security(01:11:47) Challenges and future directions in AI security(01:17:52) Companies that are doing this well(01:21:57) Final thoughts and recommendations—Referenced:• AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt): https://www.lennysnewsletter.com/p/ai-prompt-engineering-in-2025-sander-schulhoff• The AI Security Industry is Bullshit: https://sanderschulhoff.substack.com/p/the-ai-security-industry-is-bullshit• The Prompt Report: Insights from the Most Comprehensive Study of Prompting Ever Done: https://learnprompting.org/blog/the_prompt_report?srsltid=AfmBOoo7CRNNCtavzhyLbCMxc0LDmkSUakJ4P8XBaITbE6GXL1i2SvA0• OpenAI: https://openai.com• Scale: https://scale.com• Hugging Face: https://huggingface.co• Ignore This Title and HackAPrompt: Exposing Systemic Vulnerabilities of LLMs through a Global Scale Prompt Hacking Competition: https://www.semanticscholar.org/paper/Ignore-This-Title-and-HackAPrompt%3A-Exposing-of-LLMs-Schulhoff-Pinto/f3de6ea08e2464190673c0ec8f78e5ec1cd08642• Simon Willison’s Weblog: https://simonwillison.net• ServiceNow: https://www.servicenow.com• ServiceNow AI Agents Can Be Tricked Into Acting Against Each Other via Second-Order Prompts: https://thehackernews.com/2025/11/servicenow-ai-agents-can-be-tricked.html• Alex Komoroske on X: https://x.com/komorama• Twitter pranksters derail GPT-3 bot with newly discovered “prompt injection” hack: https://arstechnica.com/information-technology/2022/09/twitter-pranksters-derail-gpt-3-bot-with-newly-discovered-prompt-injection-hack• MathGPT: https://math-gpt.org• 2025 Las Vegas Cybertruck explosion: https://en.wikipedia.org/wiki/2025_Las_Vegas_Cybertruck_explosion• Disrupting the first reported AI-orchestrated cyber espionage campaign: https://www.anthropic.com/news/disrupting-AI-espionage• Thinking like a gardener not a builder, organizing teams like slime mold, the adjacent possible, and other unconventional product advice | Alex Komoroske (Stripe, Google): https://www.lennysnewsletter.com/p/unconventional-product-advice-alex-komoroske• Prompt Optimization and Evaluation for LLM Automated Red Teaming: https://arxiv.org/abs/2507.22133• MATS Research: https://substack.com/@matsresearch• CBRN: https://en.wikipedia.org/wiki/CBRN_defense• ...
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    1 hr and 33 mins
  • The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth)

    The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth)
    Dec 18 2025
    Elena Verna is the head of growth at Lovable, the leading AI-powered app builder that hit $200 million in annual recurring revenue in under a year with just 100 employees. In this record fourth appearance on the podcast, Elena shares how the traditional growth playbook has been completely rewritten for AI companies. She explains why Lovable focuses on innovation over optimization, how they’ve shifted from activation to building new features, and why giving away their product for free has become their most powerful growth strategy.We discuss:1. Why 60% to 70% of traditional growth tactics no longer apply in AI2. Why you have to re-find product-market fit every 3 months3. The specific growth tactics driving Lovable’s unprecedented growth4. Why giving away product is a growth strategy that beats paid ads5. “Minimum lovable product” as the new standard (not minimum viable product)6. Why activation now belongs to product teams, not growth teams7. Whether you should join an AI startup (honest tradeoffs)—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUsVercel—Your collaborative AI assistant to design, iterate, and scale full-stack applications for the webPersona—A global leader in digital identity verification—Transcript: ⁠https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna⁠—My biggest takeaways (for paid newsletter subscribers): ⁠https://www.lennysnewsletter.com/i/181207556/my-biggest-takeaways-from-this-conversation⁠—Where to find Elena Verna:• X: https://x.com/elenaverna• LinkedIn: https://www.linkedin.com/in/elenaverna• Newsletter: https://www.elenaverna.com—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 Elena Verna(05:19) The scale and growth of Lovable(08:55) Confidence in Lovable as a business(12:17) Retention at Lovable(15:02) Lovable’s unique growth levers(28:13) The role of marketing in Lovable’s success(38:09) Launching new features(40:59) Hiring and team dynamics(43:17) The value of vibe coding(49:46) The importance of community(51:47) Giving away your product for free(56:26) Tripling their company size(01:00:23) Product-market-fit challenges(01:08:50) Advice for joining AI companies(01:12:00) Work-life balance(01:15:20) What it’s like to work at Lovable(01:19:45) Women in tech(01:25:29) Final thoughts and lightning round—Referenced:• Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company• The ultimate guide to product-led sales | Elena Verna: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-product-led• 10 growth tactics that never work | Elena Verna (Amplitude, Miro, Dropbox, SurveyMonkey): https://www.lennysnewsletter.com/p/10-growth-tactics-that-never-work-elena-verna• Lovable: https://lovable.dev• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika• Stripe: https://stripe.com• What differentiates the highest-performing product teams | John Cutler (Amplitude, The Beautiful Mess): https://www.lennysnewsletter.com/p/what-differentiates-the-highest-performing• How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can’t copy | Gaurav Misra (CEO and co-founder of Captions): https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra• “Dumbest idea I’ve heard” to $100M ARR: Inside the rise of Gamma | Grant Lee (CEO): https://www.lennysnewsletter.com/p/how-50-people-built-a-profitable-ai-unicorn• Eric Ries on LinkedIn: https://www.linkedin.com/in/eries• Elena’s post on LinkedIn about Lovable Missions: https://www.linkedin.com/posts/elenaverna_everythingispossible-lovableway-activity-7401627519646474242-hn6e• SheBuilds: https://shebuilds.lovable.app• Shopify + Lovable: https://lovable.dev/shopify• The Product-Market Fit Treadmill: Why every AI company is sprinting just to stay in place: https://www.elenaverna.com/p/the-product-market-fit-treadmill• 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• Unorthodox frameworks for growing your product, career, and impact | Bangaly Kaba (YouTube, Instagram, Facebook, Instacart): https://www.lennysnewsletter.com/p/frameworks-for-growing-your-career-bangaly-kaba• The adjacent user: https://brianbalfour.com/quick-takes/the-adjacent-user• Granola: https://www.granola.ai• Wispr Flow: https://wisprflow.ai• I...
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    1 hr and 32 mins
  • Why humans are AI’s biggest bottleneck (and what’s coming in 2026) | Alexander Embiricos (OpenAI Codex Product Lead)

    Why humans are AI’s biggest bottleneck (and what’s coming in 2026) | Alexander Embiricos (OpenAI Codex Product Lead)
    Dec 14 2025
    Alexander Embiricos leads product on Codex, OpenAI’s powerful coding agent, which has grown 20x since August and now serves trillions of tokens weekly. Before joining OpenAI, Alexander spent five years building a pair programming product for engineers. He now works at the frontier of AI-led software development, building what he describes as a software engineering teammate—an AI agent designed to participate across the entire development lifecycle.We discuss:1. Why Codex has grown 20x since launch and what product decisions unlocked this growth2. How OpenAI built the Sora Android app in just 18 days using Codex3. Why the real bottleneck to AGI-level productivity isn’t model capability—it’s human typing speed4. The vision of AI as a proactive teammate, not just a tool you prompt5. The bottleneck shifting from building to reviewing AI-generated work6. Why coding will be a core competency for every AI agent—because writing code is how agents use computers best—Brought to you by:WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lennyFin—The #1 AI agent for customer service: https://fin.ai/lennyJira Product Discovery—Confidence to build the right thing: https://atlassian.com/lenny/?utm_source=lennypodcast&utm_medium=paid-audio&utm_campaign=fy24q1-jpd-imc—Transcript: https://www.lennysnewsletter.com/p/why-humans-are-ais-biggest-bottleneck—My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/180365355/my-biggest-takeaways-from-this-conversation—Where to find Alexander Embiricos:• X: https://x.com/embirico• LinkedIn: https://www.linkedin.com/in/embirico—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 Alexander Embiricos (05:13) The speed and ambition at OpenAI(11:34) Codex: OpenAI’s coding agent(15:43) Codex’s explosive growth(24:59) The future of AI and coding agents(33:11) The impact of AI on engineering(44:08) How Codex has impacted the way PMs operate(45:40) Throwaway code and ubiquitous coding(47:10) Shipping the Sora Android app(49:01) Building the Atlas browser(53:34) Codex’s impact on productivity(55:35) Measuring progress on Codex(58:09) Why they are building a web browser(01:01:58) Non-engineering use cases for Codex(01:02:53) Codex’s capabilities(01:04:49) Tips for getting started with Codex(01:05:37) Skills to lean into in the AI age(01:10:36) How far are we from a human version of AI?(01:13:31) Hiring and team growth at Codex(01:15:47) Lightning round and final thoughts—Referenced:• OpenAI: https://openai.com• Codex: https://openai.com/codex• Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley• Dropbox: http://dropbox.com• Datadog: https://www.datadoghq.com• Andrej Karpathy on X: https://x.com/karpathy• 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• Atlas: https://openai.com/index/introducing-chatgpt-atlas• How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna: https://www.lennysnewsletter.com/p/how-block-is-becoming-the-most-ai-native• Goose: https://block.xyz/inside/block-open-source-introduces-codename-goose• Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennysnewsletter.com/p/lessons-on-building-product-sense• Sora Android app: https://play.google.com/store/apps/details?id=com.openai.sora&hl=en_US&pli=1• The OpenAI Podcast—ChatGPT Atlas and the next era of web browsing: https://www.youtube.com/watch?v=WdbgNC80PMw&list=PLOXw6I10VTv9GAOCZjUAAkSVyW2cDXs4u&index=2• How to measure AI developer productivity in 2025 | Nicole Forsgren: https://www.lennysnewsletter.com/p/how-to-measure-ai-developer-productivity• Compiling: https://3d.xkcd.com/303• Jujutsu Kaisen on Netflix: https://www.netflix.com/title/81278456• Tesla: https://www.tesla.com• Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice• Andreas Embirikos: https://en.wikipedia.org/wiki/Andreas_Embirikos• George Embiricos: https://en.wikipedia.org/wiki/George_Embiricos: https://en.wikipedia.org/wiki/George_Embiricos—Recommended books:• Culture series: https://www.amazon.com/dp/B07WLZZ9WV• The Lord of the Rings: https://www.amazon.com/Lord-Rings-J-R-R-Tolkien/dp/0544003411• A Fire Upon the Deep (Zones of Thought series Book 1): https://www.amazon.com/Fire-Upon-Deep-Zones-Thought/dp/1250237750• Radical Candor: Be a Kick-Ass Boss Without Losing ...
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    1 hr and 25 mins
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