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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 *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 *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 *Episode transcript:* https://www.lennysnewsletter.com/p/what-openai-and-google-engineers-learned *Archive of all Lenny's Podcast transcripts:* https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=4jmgl11w&dl=0 *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/183007822/referenced *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 AI’s biggest bottleneck (and what’s coming in 2026) | Alexander Embiricos (OpenAI Codex Product Lead): https://www.lennysnewsletter.com/p/why-humans-are-ais-biggest-bottleneck • Airline held liable for its chatbot giving passenger bad advice—what this means for travellers: https://www.bbc.com/travel/article/20240222-air-canada-chatbot-misinformation-what-travellers-should-know • Demis Hassabis on LinkedIn: https://www.linkedin.com/in/demishassabis ...References continued at: https://www.lennysnewsletter.com/p/what-openai-and-google-engineers-learned _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.
Molly Graham has worked for some of tech’s most effective leaders, including Mark Zuckerberg, Sheryl Sandberg, Chamath Palihapitiya, and Bret Taylor. Today she leads Glue Club, a community...
Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion.
Sander Schulhoff is an AI researcher specializing in AI security, prompt injection, and red teaming. He wrote the first comprehensive guide on prompt engineering.
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.
Tomer Cohen is the longtime chief product officer at LinkedIn, where he’s pioneering the Full Stack Builder program, a radical new approach to product development that fully embraces what...
Rachel Lockett is a sought-after executive coach and former HR leader at Stripe and Pinterest who now works with CEOs, founders, and tech leaders on emotional intelligence, resilience, and leadership skills. In this episode, Rachel shares powerful frameworks for coaching reports, having difficult conversations, avoiding burnout, and strengthening co-founder relationships. She also demonstrates these techniques through a live coaching session with me. *We discuss:* 1. When to coach and when to just tell people what to do 2. The GROW technique for helping people figure out a solution for themselves 3. Techniques for making difficult conversations less difficult 4. Avoiding burnout and designing a more energizing career 5. Building and sustaining a healthy co-founder relationship 6. Creating a one-page plan that aligns your entire company 7. Practical ways AI is transforming executive coaching and leadership development 8. Why you should ask, “Would I enthusiastically rehire this person?” to clarify talent decisions *Brought to you by:* Stripe—Helping companies of all sizes grow revenue: https://stripe.com/ Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Persona—A global leader in digital identity verification: https://withpersona.com/lenny *Transcript:* https://www.lennysnewsletter.com/p/a-guide-to-difficult-conversations *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/178940830/my-biggest-takeaways-from-this-conversation *Where to find Rachel Lockett:* • LinkedIn: https://www.linkedin.com/in/rhlockett/ • Website: https://www.lockettcoaching.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 Rachel Lockett (04:58) The human side of business building (09:00) Coaching vs. advising (13:09) Skill 1: Active listening (18:37) Skill 2: Powerful questions (24:49) Real-life coaching example (27:36) Live coaching example with Lenny (41:55) Addressing burnout in tech (51:03) Spending more time working toward your goals (53:09) Discovering her passion for executive coaching (57:36) It's your job to navigate your career (58:44) Why Rachel says to start small (01:00:49) Building strong co-founder relationships (01:06:50) Handling co-founder conflicts (01:12:35) Improving interpersonal skills with team members (01:20:28) Reframing difficult conversations as growth opportunities (01:31:47) The one-page plan for company alignment (01:36:50) Leveraging AI in coaching and personal development (01:42:04) Lightning round and final thoughts *Referenced:* • One-page plan template: https://www.lockettcoaching.com/#resources • Lockett Coaching Leadership Toolkit: https://www.dropbox.com/scl/fi/s74a9cn1ka1ebz6pglypf/Leadership-Toolkit_-Coaching-Rachel-Lockett.pdf?rlkey=yg2m9df2ziwy0fa6p0dt4gcfu&st=dgzvnf76&dl=0 • Renew Your Co-Founder Vows—and Other Tactics for Strengthening the Most Important Relationship in Your Startup: https://review.firstround.com/five-practices-to-strengthen-your-co-founder-relationship/ • First Round Guide to Co-Founder Check-Ins: https://docs.google.com/document/d/1yUosmfMuE-8-sAwPrEPDcGqkJLVLWg5dC2_8lcXm7U4/edit?tab=t.0 • Coinbase: https://www.coinbase.com • Management Time: Who’s Got the Monkey?: https://hbr.org/1999/11/management-time-whos-got-the-monkey • Chuck Palahniuk’s quote from Fight Club: https://www.goodreads.com/quotes/1338270-people-don-t-listen-they-just-wait-for-their-turn-to • Patrick Collison on X: https://x.com/patrickc • Stripe: https://stripe.com • Remind: https://www.remind.com • Zach Abrams on LinkedIn: https://www.linkedin.com/in/zacharyabrams • Brex: https://www.brex.com • Bridge: https://www.bridge.xyz • Superhuman’s secret to success: Ignoring most customer feedback, manually onboarding every new user, obsessing over every detail, and positioning around a single attribute: speed | Rahul Vohra (CEO): https://www.lennysnewsletter.com/p/superhumans-secret-to-success-rahul-vohra • Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building • The Enneagram Institute: https://www.enneagraminstitute.com • How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin • How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC): https://www.lennysnewsletter.com/p/jerry-colonna ...References continued at: https://www.lennysnewsletter.com/p/a-guide-to-difficult-conversations _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.
Stewart Butterfield is the co-founder of Slack and Flickr, two of the most influential products in internet history. After selling Slack to Salesforce in one of tech’s biggest acquisitions,...
Melanie Perkins is CEO and co-founder of Canva, currently valued at over $42 billion, generating over $3 billion in annual revenue, with more than 240 million monthly active users and, incredibly,...
Dhanji R. Prasanna is the chief technology officer at Block (formerly Square), where he’s managed more than 4,000 engineers over the past two years. Under his leadership, Block has become...
Chip Huyen is a core developer on Nvidia’s Nemo platform, a former AI researcher at Netflix, and taught machine learning at Stanford. She’s a two-time founder and the author of two widely...
Nicole Forsgren created the most widely used frameworks for measuring developer productivity—DORA and SPACE. She wrote the foundational book Accelerate and is about to release her newest...
Robby Stein is VP of Product at Google, where he oversees the core products of Google Search—including the new AI Overviews, AI Mode, search ranking, Google Lens, and more. Previously, he...
Albert Cheng has led growth at three of the world’s most successful consumer subscription companies: Duolingo, Grammarly, and Chess.com. A former Google product manager (and serious pianist!),...
Julie Zhuo is the former VP and Head of Design at Facebook (now Meta), author of the bestselling book The Making of a Manager, and co-founder of Sundial, an AI-powered data analysis company....
Brendan Foody is the CEO and co-founder of Mercor, the fastest-growing company in history to go from $1M to $500M in revenue (in just 17 months!). At 22, he is also the youngest American unicorn...
Ben Horowitz is the co-founder of Andreessen Horowitz, Silicon Valley’s largest and most influential venture capital firm, with over $46B in committed capital across multiple funds. He took...
Asha Sharma leads AI product strategy at Microsoft, where she works with thousands of companies building AI products and has unique visibility into what’s working (and what’s not) across...
Brian Balfour is the founder of Reforge, the former VP of Growth at HubSpot, and a student (and teacher) of product growth. Brian has studied every major platform shift—from Facebook to Apple...
Matt LeMay spent 13 years as a music critic at Pitchfork before becoming one of product management’s most influential voices. He’s consulted with companies from startups to Fortune 500s...
Nick Turley is Head of ChatGPT, the fastest-growing product in history, with 700 million weekly active users (10% of the world's population). He was part of the original hackathon team that built ChatGPT.
Chip Conley is the founder of Joie de Vivre hotels, the second-largest boutique hotel brand in the world. At age 52, he joined Airbnb as Head of Global Hospitality and Strategy, reporting to CEO Brian Chesky, who was 21 years younger. He earned the title of Airbnb's "Modern Elder" by guiding young founders on leadership and culture while learning Silicon Valley's tech mindset himself. Today, Chip leads the Modern Elder Academy, the world's first midlife wisdom school.
Bret Taylor’s legendary career includes being CTO of Meta, co-CEO of Salesforce, chairman of the board at OpenAI (yes, during that drama), co-creating both Google Maps and the Like button,...
Madhavan Ramanujam is the world’s foremost expert on pricing and monetization strategy. As managing partner at Simon-Kucher, he helped over 250 companies, including 30 unicorns, architect...